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Extract of Passion Fruit (Passiflora edulis) Seed Containing High Amounts of Piceatannol Inhibits Melanogenesis and Promotes Collagen Synthesis

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Abstract

The effect of passion fruit, the fruit of Passiflora edulis , on melanin inhibition and collagen synthesis was studied using cultured human melanoma and fibroblast cells. Passion fruit was divided into three parts, rind (PF-R), pulp (PF-P), and seed (PF-S), and each part was extracted using 80% ethanol. The concentration of polyphenols was higher in PF-S than in PF-R or PF-P. Treatment of melanoma cells with PF-S led to inhibition of melanogenesis. In addition, the production of total soluble collagen was elevated in dermal fibroblast cells cultured in the presence of PF-S. PF-R and PF-P did not yield these effects. Furthermore, the removal of polyphenols from PF-S led to the abolishment of the effects described above. We discovered that piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is present in passion fruit seeds in large amounts and that this compound is the major component responsible for the PF-S effects observed on melanogenesis and collagen synthesis.

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... This fruit is rich in minerals, vitamins B, C and E, fatty acids (the most important being linoleic acid (C18:2; ω-6), oleic acid (C18:1) and palmitic acid (C16:0); linolenic acid (C18:3; ω-3) and miristic acid (C14:0) are found in smaller amounts), carotenoids, phytosterols, tocopherols, tocotrienol and phenolics compounds (phenolics acids, flavonoids, stilbenes), being highly appreciated for the quality of its juice, its pleasant aroma and flavor [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Pan [16,[23][24][25] identified the main phenolic component of passion fruit seeds as being piceatannol stilbene. Passion fruit seed extract and isolated compounds were reported to have biological activities, such as inhibition of melanogenesis and collagen synthesis [24], antioxidant activity and vasorelaxant effect [26] and cytotoxic/antitumor activity [27]. ...
... Pan [16,[23][24][25] identified the main phenolic component of passion fruit seeds as being piceatannol stilbene. Passion fruit seed extract and isolated compounds were reported to have biological activities, such as inhibition of melanogenesis and collagen synthesis [24], antioxidant activity and vasorelaxant effect [26] and cytotoxic/antitumor activity [27]. ...
... Piceatannol was identified in this work as the majority phenolic compound in passion fruit seed extracts, corroborating the studies by Krambeck et al. [70], Matsui et al. [24] and Viganó et al. [67], not being possible to quantify due to the method of analysis used. ...
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This study optimized the extraction process of yellow passion fruit seed waste, using dynamic maceration (DME) and ultrasound-assisted extraction (UAE) methods. Hydroethanolic solvent, time and temperature were studied. The extracts were evaluated for antioxidant activity by DPPH method and Fe (II) ion chelating ability. In terms of solvent optimization, experiments performed by DME, and ethanol: water with the ratio of 80:20 (v/v) indicated the best antioxidant responses. A central composite rotatable design was used to optimize the DME parameters (time and temperature). The experimental condition that provided the extract with the highest antioxidant potential was 41 min and /45 °C. The best condition for the UAE was 15 min and 45 °C. The results of antioxidant activity and yield obtained by UAE were superior to those of DME. The methods used for antioxidant activity estimation were ABTS+ radical scavenging, Fe (II) Ion Chelating Ability, DPPH free radical scavenging, phenolic and flavonoid compounds. Mass spectrometry was used to characterize the extracts. Fatty acids, were identified by the full scan method and phenolic acids, flavonoids and stilbenes by the multiple reaction monitoring method. The photoprotective activity of the optimized extracts was analyzed by determining the sun protection factor (SPF). The extracts obtained by DME and UAE had the SPF of 18.22 and 11.68, respectively, suggesting their incorporation in dermo-cosmetic formulations. The extract obtained by UAE demonstrated an antiproliferative effect on the SIHA cell line and cell division stimulating effect on the HuH7.5 cell line. The results showed that the extract from passion fruit seeds which are considered waste has high antioxidant potential and compounds of biological interest, which are necessary for further studies aiming at its pharmacological application. Graphical Abstract
... Passion fruit (Passiflora edulis Sims) is a tropical plant belonging to the Passifloraceae family, whose fruits are commonly consumed across the world because of its attractive aroma, flavor, and taste (He et al., 2020). Passion fruit seed extract (PFSE) has a potential to become a functional food because of being a rich source of stilbenes, especially piceatannol (3,3′,4′,5-trans-tetrahydroxy-stilben e) (Matsui et al., 2010). Piceatannol is a naturally occurring stilbene derivative and a structurally related polyphenol analog of resveratrol (3,4′,5-trans-trihydroxy-stilbene). ...
... In this study, we have focused on the bioactivities of piceatannol and piceatannol-rich PFSE as a functional food in both healthcare and preventive care. We previously reported that piceatannol and/or PFSE showed a variety of biological activities such as skin protection (Maruki-Uchida et al., 2013;Matsui et al., 2010), vasodilatation (Kinoshita et al., 2013), chronic diseases' prevention (Kawakami et al., 2014), and metabolic improvement (Kitada et al., 2017;Uchida-Maruki et al., 2015;Yamamoto et al., 2017). Interestingly, in our previous study, we indicated that PFSE has suppressed cancer cell proliferation more intensely than piceatannol in both NCI-H522 human non-small-cell lung cancer cells and HCT116 human colorectal cancer cells (Yamamoto et al., 2019). ...
... In this study, we focused on the biological effects of piceatannolrich PFSE and piceatannol in order to be evaluated as a functional food in healthcare, preventive care, and diverse chronic disease treatment. It was previously suggested that PFSE powder has the potential to be used as a functional food, being a rich source of stilbenes, especially piceatannol (Matsui et al., 2010). In the present study, we showed that both piceatannol and piceatannol-rich PFSE were able to prevent Aβ-induced neurite fragmentation and neuronal cell death in an AD cell model using neuron-like differentiated human SH-SY5Y Several previous studies demonstrated that piceatannol exhibited neuroprotective effects on Aβ-induced neurotoxicity in both rat pheochromocytoma PC12 cells and rat primary cortex neurons (Fu et al., 2016;Kim et al., 2007;Wen et al., 2018). ...
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Alzheimer's disease (AD) is a progressive neurodegenerative disease with accompanying perceptive disorder. We previously reported that decreasing levels of brain‐derived neurotrophic factor (BDNF) promoted beta‐amyloid (Aβ)‐induced neuronal cell death in neuron‐like differentiated SH‐SY5Y (ndSH‐SY5Y) human neuroblastoma cells in an AD mimic cell model. We investigated the neuroprotective effects of passion fruit seed extract (PFSE) and one of the main stilbene compounds, piceatannol, in an AD cell model using ndSH‐SY5Y cells. Both PFSE and piceatannol were found to protect Aβ‐induced neurite fragmentation in the cell model (protection efficacy; 34% in PFSE and 36% in piceatannol). In addition, both PFSE and piceatannol suppress Aβ‐induced neuronal cell death in the cell model (inhibitory effect; 27% in PFSE and 32% in piceatannol). Our study is the first to report that piceatannol‐rich PFSE can repress Aβ‐induced neuronal cell death by protecting against neurite fragmentation in the AD human cell model. These findings suggest that piceatannol‐rich PFSE can be considered a potentially neuroprotective functional food for both prevention and treatment of AD. We investigated the neuroprotective effect of piceatannol and passion fruit seed extract (PFSE) rich in this compound in an Alzheimer's disease (AD) mimic cell model. Both piceatannol and PFSE were found to protect beta‐amyloid‐induced neurite fragmentation in the AD cell model. Both piceatannol and PFSE were proven to suppress beta‐amyloid‐induced neuronal cell death in the AD cell model.
... Analysis of total polyphenol contents in P. edulis peel, pulp, and seeds showed that 88% of the total polyphenols were found in the seeds [39]. Various polyphenols (including stilbenes) have been isolated and identified from seeds, and the reported polyphenol components are shown in Table 3. P. edulis f. edulis 97% ethanol [49] There are many reports on the isolation of stilbenes from P. edulis seeds, especially piceatannol (3,3 ,4,5 -tetrahydroxy-trans-stilbene), which is considered to be one of the main components of P. edulis seeds. ...
... Piceatannol has been reported to be present in some plants, and the piceatannol content in the edible part of the grape berry is reported to be 0.78 µg/g [53]. According to studies on the amount of piceatannol contained in P. edulis seeds determined by ethanol extraction, concentrations of 4.8 [39], 5.7 [46], 13.97 [43], and 36.8 mg [29] per gram of dry seed were reported. Therefore, compared to other plants, the edible portion of P. edulis seeds is rich in piceatannol. ...
... In vitro experiments have shown that ethanol extract of P. edulis seeds increases collagen production when applied to dermal fibroblasts [39]. In addition, ethanol extracts of P. edulis seeds exhibit inhibitory activity against collagenase and elastase [58,64,65]. ...
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The genus Passiflora L. is widely cultivated in tropical and subtropical regions. The major species, Passiflora edulis Sims, is known as ‘passion fruit’ and is widely used in processed foods as well as eaten raw. P. edulis fruits are eaten for their pulp together with the seeds; however, the seeds are often discarded when used in processed foods. P. edulis seeds contain a variety of nutrients and functional components, and their industrial use is desirable from the perspective of waste reduction. Previous studies have analyzed the constituents of P. edulis and their physiological functions. P. edulis seeds contain various types of polyphenols, especially those rich in stilbenes (e.g., piceatannol). P. edulis seed extracts and isolated compounds from seeds have been reported to exhibit various physiological functions, such as antioxidant effects, improvement of skin condition, fat-burning promotion effects, and hypoglycemic effects. This review summarizes the nutritional characteristics, polyphenol content, and physiological functions of P. edulis seeds.
... Phytoalexins are secondary metabolites with antimicrobial activity that accumulate at the site of infection, are generally undetectable in the plant body before infection, and are rapidly synthesized when the plant is attacked by microorganisms. Resveratrol is found in red wine, grapes, mulberries, passion fruits [12], and peanuts [13]. Biological activities of resveratrol against CVD include anti-inflammation [10,14], suppression of the ICAM-1 gene expression [15], antioxidation [16,17], inhibition of vascular smooth muscle cell proliferation [18,19], enhancement of endothelial nitric oxide synthase (eNOS) activity [20,21], inhibition of platelet aggregation [22], suppression of postprandial hyperglycemia [23], and promotion of vasodilation [20,24]. ...
... Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene), which is an analog of resveratrol (3,4,5-trihydroxy-trans-stilbene) ( Fig. 1), has been reported to have the following effects: antioxidation [25,26], anti-inflammation [14,[27][28][29], inhibition of smooth muscle cell proliferation [30], anti-arrhythmia [31], anticancer [32,33], anti-melanin generation [12,25], stimulation of collagen synthesis [12], inhibition of a-amylase activity in mouse plasma [34], enhanced expression of eNOS as manifested by increased levels of eNOS mRNA and protein [35], suppression of postprandial hyperglycemia [23], increased fat oxidation [36], inhibition of androgen synthesis and androgen receptor activation [37], and alleviation of endoplasmic reticulum stress [38]. In addition, piceatannol has been reported to have beneficial effects on many pathological conditions including behavioral disorders and brain injury in an aging mouse model [39], Streptococcus suis infection [40], cytomegalovirus infection [41], ischemic heart disease [42], arrhythmias, neurodegenerative diseases, diabetes [43][44][45], liver fibrosis [46], benign prostatic hypertrophy [38], obesity [47], obesity-related early-stage nephropathy [48], angiogenesis-related disease [49], and dry skin [50]. ...
... Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene), which is an analog of resveratrol (3,4,5-trihydroxy-trans-stilbene) ( Fig. 1), has been reported to have the following effects: antioxidation [25,26], anti-inflammation [14,[27][28][29], inhibition of smooth muscle cell proliferation [30], anti-arrhythmia [31], anticancer [32,33], anti-melanin generation [12,25], stimulation of collagen synthesis [12], inhibition of a-amylase activity in mouse plasma [34], enhanced expression of eNOS as manifested by increased levels of eNOS mRNA and protein [35], suppression of postprandial hyperglycemia [23], increased fat oxidation [36], inhibition of androgen synthesis and androgen receptor activation [37], and alleviation of endoplasmic reticulum stress [38]. In addition, piceatannol has been reported to have beneficial effects on many pathological conditions including behavioral disorders and brain injury in an aging mouse model [39], Streptococcus suis infection [40], cytomegalovirus infection [41], ischemic heart disease [42], arrhythmias, neurodegenerative diseases, diabetes [43][44][45], liver fibrosis [46], benign prostatic hypertrophy [38], obesity [47], obesity-related early-stage nephropathy [48], angiogenesis-related disease [49], and dry skin [50]. ...
Article
Cardiovascular disease is a global health problem. According to the World Health Organization, ischemic heart disease was the leading cause of death globally in 2019, followed by stroke. The French paradox, which has been known since the early 1990s, describes the lower incidence of ischemic heart disease in French people despite the consumption of a diet rich in saturated fatty acids. This phenomenon has been attributed to the high intake of red wine, which is rich in polyphenols, namely, resveratrol and piceatannol. It is becoming clear that scirpusin B, a dimer of piceatannol, has anti-atherosclerotic properties such as vasodilation, antioxidant effects, and suppression of postprandial hyperglycemia; nonetheless, the effects of scirpusin B on the cardiovascular system have not been fully elucidated. This review aimed to describe the cardiovascular effects of piceatannol and scirpusin B on aortic and coronary artery dilation and cardiac function and to outline the cardiovascular effects of prostacyclin and nitric oxide, as these substances are involved in the vasodilatory effects exerted by these polyphenols.
... Piceatannol, a hydroxylated resveratrol analog, is the most abundant polyphenol detected in the passion fruit seed (Matsui et al., 2010). ...
... In vitro properties of piceatannol-rich extracts obtained from passion fruit bagasse and seeds include intense antioxidant capacity (Rotta et al., 2020;Viganó, Aguiar, et al., 2016), which is related to antiaging effects on dermal cells (Matsui et al., 2010) and keratinocytes (Maruki-Uchida et al., 2013), as well as strongly antiproliferative properties only in tumor cells (Yamamoto et al., 2019). Moreover, the in vivo antioxidant properties are still poorly understood. ...
... Through the sequential application of two environmentally friendly techniques for extraction, we obtained a piceatannol-rich extract from passion fruit bagasse, with compound concentration 25% and 49% higher than Matsui et al. (2010) and Rotta et al. (2020), that used conventional techniques. Other bioactive compounds were identified in PFBE, as the scirpusin-B, (+)-catechin, citric acid, and dicaffeoylquinic acid. ...
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We evaluated the impact of yellow passion fruit (Passiflora edulis sp.) bagasse extract (PFBE) administration in systemic oxidative and inflammatory parameters in vivo, considering prostate cancer progression in transgenic mice (TRAMP). Piceatannol, scirpusin-B, dicaffeoylquinic acid, citric acid, and (+)-catechin were identified in PFBE, and the extract showed high in vitro antioxidant capacity. Some alterations in systemic parameters were verified during prostate cancer progression, as the increase in ALT and MDA levels, and SOD and GPx activities in the plasma. In the liver, higher MDA, TNF-α, and NF-κB levels, and GR and GPx activities were verified. Compared to their respective controls, the short- and long-term PFBE administration reduced MDA levels in the liver and plasma. The long-term treatment increased the catalase activity in the plasma, while the short-term treatment increased the hepatic SOD and catalase activities. Still, a reduction in hepatic TNF-α and NF-κB levels was verified after long-term treatment. Practical applications Prostate cancer progression is associated with changes in systemic redox status and inflammation markers. Moreover, the intake of polyphenols with antioxidant properties, besides delaying prostate carcinogenesis, may improve the systemic antioxidant defenses and inflammatory response. In vitro studies pointed to a promising antioxidant and anti-inflammatory potential of yellow passion fruit bagasse. However, in vivo studies are scarce. Our results provided information about in vivo impacts of PFBE oral consumption on antioxidant defense and inflammation, indicating its potential as an adjuvant during the initial steps of prostate cancer.
... Kato et al., 2021 [276] reported on food phytochemicals including theaflavin, epigallocatechin gallate, myricetin, piceatannol, herbacetin, isothiocyanates and myricitrin inhibited SARS-CoV-2 MPro enzyme with IC50 values ranging from 0.4 to 33.3 µM against the 0.5-µM of the enzyme. Piceatannol is a resveratrol metabolite abundantly produced in Passiflora edulis fruits (Matsui et al., 2010) [277]. Piceatannol inhibits the SARS-CoV-2 MPro enzyme wherein its catechol structure was found to be critical for the interaction with the enzyme. ...
... Kato et al., 2021 [276] reported on food phytochemicals including theaflavin, epigallocatechin gallate, myricetin, piceatannol, herbacetin, isothiocyanates and myricitrin inhibited SARS-CoV-2 MPro enzyme with IC50 values ranging from 0.4 to 33.3 µM against the 0.5-µM of the enzyme. Piceatannol is a resveratrol metabolite abundantly produced in Passiflora edulis fruits (Matsui et al., 2010) [277]. Piceatannol inhibits the SARS-CoV-2 MPro enzyme wherein its catechol structure was found to be critical for the interaction with the enzyme. ...
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Abstract: The current century has witnessed infections of pandemic proportions caused by Coron�aviruses (CoV) including severe acute respiratory syndrome-related CoV (SARS-CoV), Middle East respiratory syndrome-related CoV (MERS-CoV) and the recently identified SARS-CoV2. Significantly, the SARS-CoV2 outbreak, declared a pandemic in early 2020, has wreaked devastation and imposed intense pressure on medical establishments world-wide in a short time period by spreading at a rapid pace, resulting in high morbidity and mortality. Therefore, there is a compelling need to combat and contain the CoV infections. The current review addresses the unique features of the molecular virology of major Coronaviruses that may be tractable towards antiviral targeting and design of novel preventative and therapeutic intervention strategies. Plant-derived vaccines, in particular oral vaccines, afford safer, effectual and low-cost avenues to develop antivirals and fast response vaccines, requiring minimal infrastructure and trained personnel for vaccine administration in developing countries. This review article discusses recent developments in the generation of plant-based vaccines, therapeutic/drug molecules, monoclonal antibodies and phytochemicals to preclude and combat infections caused by SARS-CoV, MERS-CoV and SARS-CoV-2 viruses. Efficacious plant-derived antivirals could contribute significantly to combating emerging and re-emerging pathogenic CoV infections and help stem the tide of any future pandemics.
... Grape stems Methanolic extracts using ultrasound-assisted extraction [4] Grapevine Vitis vinifera Dissolved in methanol [5] Lophatherum gracile stem and leaves 95% ethanol at a temperature of 80°C under reflux [6] Moscato bianco grapes Methanol extract using Ultra-Turrax [7] Passion fruit (Passiflora edulis) seeds The ground seeds were extracted with 70% acetone 3 times, with shaking [8] Passion fruit (Passiflora edulis) seeds Extraction with an organic solvent [9] Passion fruit (Passiflora edulis) seeds and seed cake Supercritical fluid extraction and ultrasound [10] The sim fruit (Rhodomyrtus tomentosa) The powdered freeze-dried fruit was mixed with acetone: water: acetic acid (50:49:1; v/v/v) and shaken for one hour at 37°C [11] 15 For this reason, there is a high demand for melanogenesis inhibitors, which allowed to reduce or prevent these hyperpigmental disorders. ...
... It was verified that there was a significant increase in melanin synthesis inhibition, as well as an increase in collagen production in the samples tested with piceatannol and resveratrol, showing that piceatannol was superior to resveratrol in both cases, possibly due to the structure of the piceatannol, which presents one more hydroxyl group than resveratrol. 8 The in vitro effect of passion fruit extract using human MNT-1 melanoma cells and human SF-TY fibroblast cells was studied for the inhibition of melanogenesis and the promotion of collagen synthesis. It was demonstrated, due to the presence of polyphenols such as piceatannol, resveratrol and sircusin B in passion fruit seed extract, that there was a strong inhibition of melanin synthesis, as well as an increased collagen synthesis. ...
Article
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The skin is the largest organ of the human body and has several functions such as barrier against external agents, the maintenance of temperature and homeostatic functions. Skin ageing is a natural process that can be influenced by environmental factors, intrinsic skin factors and lifestyle. UV light plays an important role in skin ageing and can cause spots, requiring the use of depigmenting agents. Nowadays, there is a great demand for ingredients that prevent skin ageing, with natural agents occupying a promising position. Among the natural agents, polyphenols, such as resveratrol and piceatannol, found in grapes, passion fruits and other fruits, have a huge relevance. Great benefits of piceatannol have been reported, so thus, this work focuses specifically on a review of the literature regarding the application of this polyphenol in skin care products. This polyphenol can be used in a wound-healing, or as anti-ageing, antioxidant, anti-acne and skin whitening, among other effects.
... "Piceatannol and fruits" Shruthi et al., 2020Fan et al., 2022Leal et al., 2017Wijekoon et al., 2022Cardile et al., 2005Jiang et al., 2020Piotrowska et al., 2012Yamamoto et al., 2020Potter et al., 2002Matsui et al., 2010FerrignI et al., 1984Lee et al., 2022Know et al., 2022Algandaby e Al-Sawahli, 2021Yang et al., 2020Kroplewska et al., 2019 Kido et al., Shi et al., 2020Sato et al., 2022Baseggio et al., 2022Sáez et al., 2018Arai et al., 2016Banik et al., 2020Kawakami et al., 2014Kershaw e Kim, 2017Kukreja et al., 2014Osamudiamen et al., 2020Park et al., 2021Setoguchi et al., 2014King et al., 1956Silva et al., 2021Misuzaki et al., 2017Pan et al., 2020Zomer et al., 2022Viñas et al., 2011Vinãs et al., 2009Zachová et al., 2018Avendaño-Godoy et al., 2022Lai et al., 2014Rimando et al., 2004Xie e Bolling, 2014Ersan et al., 2020Ku et al., 2005Santos et al., 2017Boue et al., 2013 Fonte: Autores. ...
... Fonte: Adaptado de Sherestha et al. (2019). E, além de ser biossintetizado pelas plantas, o piceatannol também já foi identificado no metabolismo humano como metabólito do resveratrol por hidroxilação da enzima citocromo P450 CYP1B1, que é altamente expressa em tumores humanos, convertendo resveratrol em piceatannol, conforme apresentado na Figura 3(Potter et al., 2002;Matsui et al., 2010). ...
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Piceatannol (trans-3,3,4,5-tetrahidroxiestilbeno) é um análogo estrutural relacionado ao resveratrol, pertencente ao grupo dos estilbenos. É encontrado em fontes naturais como amêndoas, amendoim, chás, berries e maracujá, mas principalmente em uvas e nas sementes de maracujá. Estudos têm mostrado que ele possui uma gama de propriedades biológicas promotoras de saúde, com destaque para o potencial antioxidante, anti-inflamatório e anticancerígeno. Embora o resveratrol tem sido o estilbeno mais conhecido e mais estudado, estudos têm mostrado que o piceatannol está presente em quantidades superiores às do resveratrol em diversas fontes vegetais naturais e, além disso, devido à presença do grupo hidroxila adicional na posição 3’ em sua estrutura tem apresentado algumas atividades biológicas superiores às do resveratrol. Em vista disso, nesse estudo foi realizada uma revisão bibliográfica sistemática, acerca das principais características químicas, fontes naturais e propriedades biológicas do piceatannol. Assim, este estudo vai contribuir e incentivar a divulgação do conhecimento e o desenvolvimento de novos estudos acerca desse composto natural potencialmente útil para a saúde humana.
... Piceatannol (3,3 , 4 5-Tetrahydroxystilbene, C 14 H 12 O 4 ) is a natural stilbene (plant polyphenol), proven to work as an excellent antioxidant and chemoprotective compound [8]. Piceatannol is found in significant amounts in Vitis vinifera (wine grapes) [9], Rhodomyrtus tomentosa (sim fruit) [10], and in P. edulis seeds [11]. Despite the similarity with resveratrol's molecule structure, piceatannol seems to exhibit improved properties, promoting health benefits that are not accounted for by resveratrol [12][13][14]. ...
... Rotta et al. [6] applied hydro-alcohol extracts from passion fruit seed in dairy beverages, decreasing their lipid oxidation. In addition to its antioxidant effect, piceatannol also promoted the reduction of vascular tension [15], anti-aging effects [5], and protection against UV rays due to its inhibition effects on the production of melanin pigments [5,11]. ...
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Passiflora edulis by-products (PFBP) are a rich source of polyphenols, of which piceatannol has gained special attention recently. However, there are few studies involving environmentally safe methods for obtaining extracts rich in piceatannol. This work aimed to concentrate piceatannol from defatted PFBP (d-PFBP) by means of pressurized liquid extraction (PLE) and conventional extraction, using the bio-based solvents selected with the Hansen solubility parameters approach. The relative energy distance (Ra) between solvent and solute was: Benzyl Alcohol (BnOH) < Ethyl Acetate (EtOAc) < Ethanol (EtOH) < EtOH:H2O. Nonetheless, EtOH presented the best selectivity for piceatannol. Multi-cycle PLE at 110 °C was able to concentrate piceatannol 2.4 times more than conventional extraction. PLE exhibited a dependence on kinetic parameters and temperature, which could be associated with hydrogen bonding forces and the dielectric constant of the solvents. The acetylcholinesterase (AChE) and lipoxygenase (LOX) IC50 were 29.420 μg/mL and 27.682 μg/mL, respectively. The results reinforce the demand for processes to concentrate natural extracts from food by-products.
... In Viet Nam, P. edulis is popularly cultivated in Tay Nguyen, Nghe An and Son La with areas of over ten thousand hectares. The P. edulis extracts were found to possess biological activities, including antioxidant [2], antifungal [3] and compounds from the seeds of P. edulis were found to inhibit melanogenesis and promote collagen synthesis [4]. Previous studies on chemical constituents of P. edulis seeds showed the presence of stilbenoids [4,5], oil and tocopherols [6]. ...
... The P. edulis extracts were found to possess biological activities, including antioxidant [2], antifungal [3] and compounds from the seeds of P. edulis were found to inhibit melanogenesis and promote collagen synthesis [4]. Previous studies on chemical constituents of P. edulis seeds showed the presence of stilbenoids [4,5], oil and tocopherols [6]. P. edulis seeds accounted for 6-12 % of fruit weight and they were used for the treatment of constipation and hemorrhoids [7]. ...
... Patient data Age: 10 years Gender: female Weight: 35kg Height: 130 cm Chief Complaint She had per rectal bleeding since last month History of Present Illness For the past month, she has had a rectal bleed that was fresh colored blood, substantial in volume, and not connected with constipation, abdominal pain, distention, vomiting, or fever. The patient was admitted to the intensive care unit (Matsui et al., 2010) and had RBCs, platelets, and FFPs transfused. Computed tomography (CT) angioembolization of the jejunal branch artery was conducted at the interventional radiology department. ...
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Medication safety is considered a core domain of quality care and can be defined as the absence of accidental injuries due to medical care or medical errors during the medication-taking process. Medication safety is the main aspect of medical therapy, which can play a key role in the choice of which medication to use in pediatrics. Since reports such as “To Error is Human” shed light on the scope and severity of medical errors, preventing medical errors has become a public health priority. Medication safety and precautions are important to prevent side effects, overdose, and death. The pediatric population is particularly vulnerable to additional risk of harm resulting from medication errors due to their physiological inability to mitigate errors.
... Piceatannol (PIC) is a natural polyphenol compound first found in grape skin and abundant in passion fruit [13]. Recently, PIC has attracted much attention from scientists because of its wide range of biological activities. ...
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Piceatannol (PIC) is a natural stilbene extracted from grape skins that exhibits biological activities such as antibacterial, antitumor, and antioxidant activities. The present study was carried out to further investigate the effect of PIC on the antibacterial activity of different antibiotics and to reveal the antibacterial mechanism of PIC. We found that PIC had an inhibitory effect against Staphylococcus aureus (S. aureus); its minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were 128 μg/mL and 256 μg/ mL, respectively. Additionally, we measured the fractional inhibitory concentration (FIC) of PIC combined with antibiotics via the checkerboard method. The results showed that when PIC and ciprofloxacin (CIP) were combined, they displayed a synergistic effect against S. aureus. Moreover, this synergistic effect was verified by time–kill assays. Further, the results of the membrane permeability assay and proton motive force assay revealed that PIC could enhance the sensitivity of S. aureus to CIP by dissipating the bacterial proton motive force (PMF), particularly the ∆ψ component, rather than increasing membrane permeability. PIC also inhibited bacterial adenosine triphosphate (ATP) synthesis and was less likely to induce bacterial resistance but exhibited slight hemolytic activity on mammalian erythrocytes. In summary, the combination of PIC and CIP is expected to become a new drug combination to combat S. aureus.
... Piceatannol is approximately nine times more accumulated in red than white grapes (red grapes: 374 ng/g; white grapes 43 ng/g) [34,35]. Passion fruit seeds are very rich in piceatannol, containing 4.8 mg/g [34,36]. The amount of piceatannol in blueberries is reported as 138-422 ng/g at dry concentration [34,37]. ...
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Stilbenoids are well-known phytoalexins in the group of polyphenolic compounds. Because of their potent bioactivities, including antioxidant, antityrosinase, photoprotective, and antibacterial activities, stilbenoids are utilized as pharmaceutical active ingredient in cosmetic products. Thus, the demand for stilbenoids in the cosmetic industry is increasing. The main sources of stilbenoids are plants. Although plants are green and sustainable source materials, some of them do not allow a regular and constant supply due to seasonal and geographic reasons. Stilbenoids typically have been extracted by conventional organic solvent extraction, and then purified by separation techniques. This method is unfriendly to the environment and may deteriorate human health. Hence, the procedures called “green technologies” are focused on novel extraction methods and sustainable stilbenoids production by using biotechnology. In this review, the chemical structures together with the biosynthesis and current plant sources of resveratrol, oxyresveratrol, and piceatannol are described. Furthermore, recent natural deep eutectic solvents (NADES) for green extraction as well as plant cell cultures for the production of those stilbene compounds are updated.
... In recent years, emerging technologies together with the increasing concern about sustainability and environmental conservation have motivated many studies that aimed to investigate possible applications for these by-products (Fierascu et al., 2020). Several fruit wastes, as a cheap source of valuable components, have been investigated for high-added value constituents (Espírito-Santo et al., 2013;Kawakami et al., 2021;Matsui et al., 2010;Pereira et al., 2019). ...
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The passion fruit juice production generates around 70% of by-products comprising rind, seeds and arils that are commonly discarded. The seeds consist of 4% of fruit weight with the potential to produce around 2,500 ton/year of high added-value oil in Brazil. In this work, passion fruit seeds from different juice manufacturers and the effect of the seed moisture were evaluated towards oil quality and extraction efficiency, using a continuous expeller press of 100 kg/h capacity. The seeds were washed and dried before pressing. The main fatty acids detected were linoleic (67% to 68%), oleic (16% to 17.4%) and palmitic (11%). The oil quality and oil recovery depended on the seed oil content, i.e., the seed moisture before pressing and the different provenances of the seeds. Significant differences were observed for oxidative stability, acidity and conjugated dienes (p < 0.05) for oils from different fruit juice manufacturers. Among them, only one met the requirements of Brazilian regulation regarding oil acidity (less than 2%), thus indicating the need for an effective waste treatment process after juice extraction. Regarding the seed moisture, the highest Oil Stability Index (OSI) (7.4 h) and lowest free fatty acid content (0.63%) were obtained for the oil from the lowest seed moisture content. The oil recovery varied from 78% to 89% and the cake oil content was lower than 8% showing the elements of the feasibility of the process to obtain good quality oil.
... As sementes do maracujá contém grandes quantidades de piceatannol (3,5,3',4'-trans-tetrahidroxistilbeno) (Uchida-Maruki et al., 2015), um fitoquímico análogo do resveratrol (Matsui et al., 2010), com potencial antioxidante e quimioprotetor (Shen et al., 2009), antienvelhecimento (Maruki-Uchida et al., 2013 e hipoglicemiante (Kitada et al., 2017). Os mecanismos hipoglicemiantes do piceatannol ainda são pouco esclarecidos (Uchida-Maruki et al., 2015), mas este composto foi capaz de promover a captação de glicose, translocação de GLUT4 e fosforilação de AMPK em miotubos L6 cultivados na ausência de insulina (Minakawa et al., 2012). ...
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O Diabetes Mellitus (DM) é uma doença crônica e progressiva, caracterizada pela hiperglicemia persistente, que pode resultar em complicações micro e macrovasculares incapacitantes e, até mesmo, fatais. A Passiflora edulis, cujo fruto é o maracujá, é uma planta abundante no Brasil e possui potencial hipoglicemiante, podendo auxiliar no tratamento do DM. O objetivo deste artigo é investigar os efeitos das partes da P. edulis no controle glicêmico de indivíduos com DM. Trata-se de uma revisão integrativa da literatura com a seguinte pergunta de pesquisa: “O maracujá (P. edulis) tem impactos sobre os parâmetros glicêmicos em indivíduos com Diabetes Mellitus?”. A busca dos dados foi realizada nas bases de dados Bireme, Cochrane Library, Scielo e Pubmed, em janeiro de 2022. Foram encontrados 14 artigos, dos quais cinco compuseram a amostra final. Três dos estudos foram ensaios clínicos randomizados, enquanto dois foram estudos experimentais. Entre as formas farmacêuticas estiveram: farinha da casca e albedo, extrato da semente e extrato etanólico das folhas de P. edulis. A maior parte dos estudos mostraram efeitos como redução da glicemia de jejum e hemoglobina glicada. É possível concluir que as partes do maracujá (P. edulis), como sementes, folhas e casca possuem substâncias que podem auxiliar no controle glicêmico de pacientes com DM, entretanto, mais estudos são necessários para assegurar seu uso.
... Previous research has already shown possible ways to reuse this waste. The bagasse has phytonutrients such as fatty acids [5], tocopherols and tocotrienols [6], carotenoids [7], essential oils [8], phytosterols [9], and phenolic compounds [10]. Among the phenolic compounds, piceatannol and scirpusin B were identified in high concentration, to which several biological activities are associated, such as antioxidant capacity and cancer-fighting activity [11,12]. ...
Article
Low-frequency ultrasound has been efficiently applied to intensify high-pressure extraction processes. However, large-scale hybridization still is challenging. This work aims to present an economic feasibility study of two different extraction processes to produce a piceatannol-rich extract from yellow passion fruit bagasse – process A (supercritical fluid extraction + pressurized liquid extraction – SFE+PLE) and process B (SFE+PLE assisted by ultrasound – SFE+PLE-US). The SuperPro Designer software was employed to estimate the manufacturing cost (COM), productivity, and economic return rates, calculated for each overall extraction curve and different scales (50, 200, and 500 L). Process A showed economically viable, while process B showed infeasible at a 20% minimum acceptable rate of return. The lowest COM and better economic return were obtained with process A at 75 °C, 500 L, and 90 min. In addition, a sensitivity study was carried out, indicating the possibility of selling the extract below the market price, representing a competitive differential to implement the extraction process at large scales. It is noteworthy that up to now, the economic feasibility of PLE-US on a large scale has not yet been performed, so this work represents a starting point for studies of PLE-US hybridization on large scales.
... The formed quinone could react with a thiol of the enzyme, resulting in the enzyme conjugation with the phytochemical ( Fig. 4 ) [31] . Piceatannol is abundantly present in the fruit of Passiflora edulis [32] and is a metabolite of resveratrol. In this study, we have discovered that piceatannol inhibits the enzyme; the catechol structure of piceatannol is presumably the critical structure for conjugation. ...
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SARS-CoV-2 main protease is a possible target for protection against viral infection. This study examined the inhibitory effect of food phytochemicals on the main protease of SARS-CoV-2 by determining a cleaved product after chromatographic separation. First, 37 phytochemicals, including glycosides and metabolites, were screened at 20 µM; epigallocatechin gallate, myricetin, theaflavin, herbacetin, piceatannol, myricitrin, and isothiocyanates inhibited the enzyme in varying degrees. The IC50 values were estimated from 0.4 to 33.3 µM against the 0.5-µM enzyme. The dose-dependent adduction of epigallocatechin gallate and myricetin was confirmed by quinone staining of protein blotted onto a membrane. The enzyme activity was decreased by increasing the concentration of the two phytochemicals, accompanied by increasing the respective adducted molecule estimated by intact mass spectrometry. Reduced glutathione canceled the formation of conjugate and the inhibitory effect of epigallocatechin gallate or myricetin on the enzyme, suggesting that the formation of the quinone moiety in the phytochemicals is critical for the inhibition. The covalent binding of epigallocatechin gallate or myricetin to the cysteine residue at the active site was confirmed by analyzing peptides from the chymotrypsin-digested main protease.
... Polyphenolic compounds have recently attracted the attention of researchers due to their pleiotropic biological activities. Piceatannol (trans-3,3 ,4 ,5-tetrahydroxystilbene, Figure 1A) is a naturally occurring polyphenol and a structural analog of resveratrol (trans-3,4 ,5-trihydroxystilbene) found in grapes, berries, passion fruit, and wine [34][35][36][37]. It has been demonstrated to exhibit a wide range of biological properties including anti-oxidative, antimicrobial, anti-inflammatory, antidiabetic, estrogenic, neuroprotective, and cardioprotective activities [38][39][40][41][42][43][44]. ...
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Acute myeloid leukemia is characterized by uncontrolled clonal proliferation of abnormal myeloid progenitor cells. Despite recent advances in the treatment of this disease, the prognosis and overall long-term survival for patients remain poor, which drives the search for new chemotherapeutics and treatment strategies. Piceatannol, a polyphenolic compound present in grapes and wine, appears to be a promising chemotherapeutic agent in the treatment of leukemia. The aim of the present study was to examine whether piceatannol induces autophagy and/or apoptosis in HL-60 human acute myeloid leukemia cells and whether HL-60 cells are able to acquire resistance to piceatannol toxicity. We found that piceatannol at the IC90 concentration of 14 µM did not induce autophagy in HL-60 cells. However, it induced caspase-dependent apoptosis characterized by phosphatidylserine externalization, disruption of the mitochondrial membrane potential, caspase-3 activation, internucleosomal DNA fragmentation, PARP1 cleavage, chromatin condensation, and fragmentation of cell nuclei. Our findings also imply that HL-60 cells are able to acquire resistance to piceatannol toxicity via mechanisms related to MRP1 activity. Our results suggest that the use of piceatannol as a potential chemotherapeutic agent may be associated with the risk of multidrug resistance, warranting its use in combination with other chemotherapeutic agents.
... Stilbenes can be also found in berries, but at much lower concentrations [43]. Apart from berries, studies have detected others dietary sources for stilbenes, such as bananas, guavas, lychees, apples, peaches, pineapples, pears and beer [44][45][46][47][48]. ...
Article
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Skin cancer represents any tumor development from the cutaneous structures within the epidermis, dermis or subcutaneous tissue, and is considered to be the most prevalent type of cancer. Compared to other types of cancer, skin cancer is proven to have a positive growth rate of prevalence and mortality. There are available various treatments, including chemotherapy, immunotherapy, radiotherapy and targeted therapy, but because of the multidrug resistance development, a low success has been registered. By this, the importance of studying naturally occurring compounds that are both safe and effective in the chemoprevention of skin cancer is emphasized. This review focuses on melanoma because it is the deadliest form of skin cancer, with a significantly increasing incidence in the last decades. As chemopreventive agents, we present polyphenols and their antioxidant activity, anti-inflammatory effect, their ability to balance the cell cycle and to induce apoptosis and their various other effects on skin melanoma. Besides chemoprevention, studies suggest that polyphenols can have treating abilities in some conditions. The limitations of using polyphenols are also pointed out, which are related to their poor bioavailability and stability, but as the technology is well developed, it is possible to augment the efficacy of polyphenols in the case of melanoma.
... Recently, piceatannol and resveratrol have been identified in the oil. These constituents have diverse biological effects, justifying most of the cosmetic claims for the oil (Matsui et al. 2010;Arai et al. 2016;Piotrowska, Kucinska, and Murias 2012;Sano et al. 2011;Maruki-Uchida et al. 2013). ...
Article
Agriculture and food science literature on waste-to-value applications that allow upcycling of by-product ingredients is increasing. However, this stream of research rarely takes an international trade and sustainability systems perspective. This focused review defines the term of waste-to-value and the sustainable development goals connected to it, and points to the tensions and questions arising when international trade is involved. Further, it exemplifies the challenges and opportunities of waste-to-value in tropical fruit trade through five cases of tropical fruit from South America: Green coconut, açaí, maracujá, cambuci, and jabuticaba. We present a model of the international supply chain that indicates where the opportunities of waste-to-value applications in international tropical fruit trade are situated, and discuss which future research questions need to be addressed to tackle the challenges of waste-to-value in global tropical fruit chains. Establishing the waste-to-value approach in the export of yet-underused tropical fruits can amongst others improve local employment, preserve natural resources, allow favorable use of side-streams in local energy production, environmentally friendly packaging material for transport, and add health functionalities to the end-consumer products, but challenges have to be solved in order to ensure these environmental and social benefits materialize.
... Piceatannol, or 3,3′,4,5′-tetrahydroxytrans-stilbene, is a natural stilbene of a hydroxylated analogue of resveratrol and is abundant in passion fruit (Passiflora edulis) seeds, grapes and blueberries. 75 Piceatannol has been detected as a resveratrol metabolite in vivo: 5 min following resveratrol administration, piceatannol was found in the plasma, skin, and liver of mice. Numerous bioactivities of piceatannol have been found, including lowered blood glucose, attenuated oxidative stress and inflammation. ...
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The internal circadian clock in mammals drives whole-body biological activity rhythms. The clock reflects changes in external signals by controlling enzyme functions and the release of hormones involved in metabolic processes. Thus, misalignments between the circadian clock and an individual's daily schedule are recognized to be related to various metabolic diseases, such as obesity and diabetes. Although evidence has shown the existence of a complex relationship between circadian clock regulation and daily food intake, the regulatory effects of phytochemicals on the circadian clock remain unclarified. To better elucidate these relationships/effects, the circadian system components in mammals, circadian misalignment-related metabolic diseases, circadian rhythm-adjusting phytochemicals (including the heterocycles, acids, flavonoids and others) and the potential mechanisms (including the regulation of clock genes/proteins, metabolites of gut microbiota and secondary metabolites) are reviewed here. The bioactive components of functional foods discussed in this review could be considered potentially effective factors for the prevention and treatment of metabolic disorders related to circadian misalignment.
... 11 In addition, passion fruit and Vaccinium berries are rich in PIC. 12,13 It was reported that PIC possesses a wide spectrum of biological activities including antidiabetic, neuroprotective, cardioprotective, anti-allergic, and anti-aging. [14][15][16] It also protects retinal pigment epithelium cells against UV-B irradiation. ...
Article
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Human exposure to radio-therapeutic doses of gamma rays can produce late effects, which negatively affect cancer patients’ quality of life, work prospects, and general health. This study was performed to explore the role of Piceatannol (PIC) in the process of “mitochondrial biogenesis” signaling pathway as possible management of disturbances induced in stressed animal model(s) either by gamma-irradiation (IR) or administration of reserpine (RES); as a mitochondrial complex-I inhibitor. PIC (10 mg/kg BW/day; orally) were given to rats for 7 days, after exposure to an acute dose of γ-radiation (6 Gy), or after a single reserpine injection (1 g/kg BW; sc). Compared to reserpine or γ-radiation, PIC has attenuated hepatic and renal mitochondrial oxidative stress denoted by the significant reduction in the content of lipid peroxides and NO with significant induction of SOD, CAT, GSH-PX, and GR activities. PIC has also significantly alleviated the increase of the inflammatory markers, TNF-α and IL-6 and apoptotic markers, cytochrome c, and caspase-3. The decrease of oxidative stress, inflammation, and apoptotic responses were linked to a significant amelioration in mitochondrial biogenesis demonstrated by the increased expression and proteins’ tissue contents of SIRT1/p38-AMPK, PGC-1α signaling pathway. The results are substantiated by the significant amelioration in mitochondrial function verified by the higher levels of ATP content, and complex I activity, besides the improvement of hepatic and renal functions. Additionally, histopathological examinations of hepatic and renal tissues showed that PIC has modulated tissue architecture after reserpine or gamma-radiation-induced tissue damage. Piceatannol improves mitochondrial functions by regulating the oxidant/antioxidant disequilibrium, the inflammatory and apoptotic responses, suggesting its possible use as adjuvant therapy in radio-therapeutic protocols to attenuate hepatic and renal injuries.
... Therefore, the doses of RSV administered during our maternal supplementation protocol correspond to the consumption of about 22 g of grapes (about thirty grape berries) per day for a pregnant woman. Similarly, taking into account the PIC content of passion fruit (2.2 mg of PIC per g of raw passion fruit seeds (Matsui et al., 2010)) and the weight of the seeds (between 5 and 10 g/fruit), a passion fruit contains about 10 to 20 mg of PIC. Therefore, the doses of PIC tested in maternal supplementation in the rat correspond to the consumption of a single passion fruit per day for a pregnant woman. ...
Thesis
L’hypoxique-ischémique (HI) néonatale est une pathologie qui touche 1-8 nourrissons sur 1000. Elle est caractérisé par une privation d'oxygène et du flux sanguin vers le cerveau au moment de la naissance. Les lésions à long terme peuvent être limitées par l'hypothermie, seule thérapie actuellement appliquée en clinique, mais de nombreux nouveau-nés n'y répondent pas. Le trans-resvératrol (RSV) joue un rôle neuroprotecteur dans diverses pathologies neurodégénératives. Notre objectif est d'étudier les effets de différents fenêtres de supplémentation maternelle en RSV sur les conséquences cérébrales d’une HI néonatale chez le rat et de décrire les différentes voies neuroprotectrices emprunter par ce polyphénol. Pour cela différents groupes de supplémentations ont été définis en fonction de la présence du RSV (0,15mg/kg) dans l’eau de boisson de la rate (préventif ou curatif). L’originalité du projet repose sur le mode d’administration qui est transgénérationnel et nutritionnel. Les ratons ont subi une HI à P7 et un suivi longitudinal des dommages a été effectué avec la mesure de la taille des lésions cérébrales par IRM (Bruker 4,7T) et divers tests comportementaux. Et pour décrypter la mécanistique du RSV, des RT-qPCR, Western Blot et analyses histologiques ont été réalisé permettant une grande complémentarité des techniques. D’une manière générale une neuroprotection a observé en présence du RSV plus particuliére pour le groupe rsvGL. En effet, le groupe rsvGL a présenté des plus petites lésions et des meilleures performances comportementales. Les analyses ont montré une augmentation de l’expression des gènes des voies de signalisations connus du RSV (SIRT1, SOD et Bcl2) et du métabolisme cérébrale (MCTs, LDHs, GLAST, GLT1, Na+/K+ATPase). En conclusion, le RSV a inévitablement des propriétés neuroprotectrices qui sont dus à l’activation de la voie des sirtuines (antioxydantes et anti apoptotiques). Néanmoins, le RSV a aussi un impact sur le métabolisme cérébrale et plus particulièrement sur la navette lactate astrocyte-neurone (ANSL) comme suggèrent les données de RT-qPCR et de western-blot qui contribuent aux effets neuroprotecteurs.
... Piceatannol (PIC) (Figure 1k) is a polyphenolic stilbene phytochemical that is found in large amounts in passion fruit seeds, berries, and grapes [278,279]. PIC is a hydroxylated analog of RES but has stronger free-radical-scavenging activity as well as greater bioavailability than RES [280,281]. Previous studies have reported that PIC has antioxidant, anti-inflammatory, and anticancer activity [282,283]. ...
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Neonatal hypoxic-ischemic (HI) brain injury is one of the major drawbacks of mortality and causes significant short/long-term neurological dysfunction in newborn infants worldwide. To date, due to multifunctional complex mechanisms of brain injury, there is no well-established effective strategy to completely provide neuroprotection. Although therapeutic hypothermia is the proven treatment for hypoxic-ischemic encephalopathy (HIE), it does not completely chang outcomes in severe forms of HIE. Therefore, there is a critical need for reviewing the effective therapeutic strategies to explore the protective agents and methods. In recent years, it is widely believed that there are neuroprotective possibilities of natural compounds extracted from plants against HIE. These natural agents with the anti-inflammatory, anti-oxidative, anti-apoptotic, and neurofunctional regulatory properties exhibit preventive or therapeutic effects against experimental neonatal HI brain damage. In this study, it was aimed to review the literature in scientific databases that investigate the neuroprotective effects of plant extracts/plant-derived compounds in experimental animal models of neonatal HI brain damage and their possible underlying molecular mechanisms of action.
... De las investigaciones más prometedoras P. edulis precede la lista por poseer en sus semillas compuestos como piceatanol capaz de inhibir la melanogénesis y promover la síntesis de colágeno. (8) La presencia de una variedad de fitoconstituyentes en el género Passiflora ha sido descrita. Sin embargo, los reportes sobre investigación farmacológica desarrollada, son limitados en Ecuador, sin embargo los estudios que existen se basan en la actividad depresora sobre el Sistema Nervioso Central (SNC) de diversas especies de Passiflora (9). ...
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La variedad climática y la ubicación territorial del Ecuador favorece la diversidad biológica en el país. Sin embargo, debido a la presencia de gran número de flora y fauna por kilómetro cuadrado, la mayor parte no se encuentra estudiada, y a pesar de no contar con argumento científico para el uso de algunas especies vegetales, la población utiliza muchas de éstas para diferentes patologías, por lo que se realizó el estudio farmacológico de seis especies del género Passiflora de la provincia de Chimborazo – Ecuador, empleadas tradicionalmente para tratar el nerviosismo. Para la identificación se llevó a cabo un perfil de cromatografía en capa fina de cada especie, de los que se pudieron determinar cantidades considerables de moléculas con agrupamiento de tipo flavónico y cuantificación de los flavonoides totales. De las especies estudiadas P. manicata se destacó por su elevado contenido de flavonoides totales usando el método de cloruro de aluminio para derivatizar los compuestos de interés y poder evaluarlos mediante espectrofotometría UV-visible. Mientras que para la actividad farmacológica se llevó a cabo in vivo mediante el modelo de laberinto en cruz elevado. De los resultados obtenidos se ha logrado determinar que al menos dos de las seis especies tienen actividad ansiolítica significativa a las dosis de 25 y 50 mg/kg de extracto hidroalcohólico, siendo P. mixta y P. edulis las especies vegetales que en su composición presentarían constituyentes bioactivos para tal efecto.
... The effect of passion fruit on melanogenesis and collagen synthesis in dermal cells and the components responsible for these effects were studied. The ethanolic seed extract contained piceatannol which exhibited antioxidative properties and melanin inhibitory activity [17]. The crude extract of passion fruit peel contains flavonoids, cyanogenic, phenolics and polysaccharides. ...
Article
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Plants belonging to the Genus Passiflora have been commonly used in traditional medicine for a variety of health conditions. The major bioactive components present in these plants are identified as flavonoids, alkaloids, glycosides and phenolic compounds. Six species belonging to the Genus Passiflora which have been well documented are P. alata, P. caerulea, P. edulis, P. foetida, P. incarnata, P. ligularis. Also, the subspecies P. edulis Sims f. Flavicarpa has been well documented for its phytochemical composition and human healthcare applications. There are well documented evidence-based scientific studies which are continuing to be reported on the medicinal value of these plants. These studies include both in vitro and in vivo studies using cell lines and animal models, respectively. The studies highlight the importance of these plant species for their therapeutic values in gastrointestinal conditions, neurological complications, cardiovascular conditions, inflammation and as anti-anxiolytic agents. We present in this review a systematic account on the phyto-constituents present in various plant parts of the six different species of this Genus along with the in vitro and in vivo experiments that highlighted their pharmacological importance.
... Consistently, piceatannol isolated in a large amount (2.2 mg/g) the fruit seeds from Passiflora edulis Sims. was concluded to be the molecule responsible for anti-melanogenic effect of the extract in MNT-1 human melanoma cells [63]. The reason why piceatannol was a stronger TYR inhibitor than RSV was explained with additional hydroxyl group on piceatannol. ...
Article
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Melanogenesis is simply defined as production of melanin in melanosomes by melanocytes through a complex process. Melanin, a pigment derived from L-tyrosine, comes into two forms, namely eumelanin (brownish to black) and pheomelanin (red to yellow). Melanin synthesis starts via the hydroxylation of L-tyrosine to L-3,4-dihydroxyphenylalanine (DOPA) catalyzed by the enzyme known as tyrosinase (TYR), which triggers further conversion reaction to DOPAquinone and then to DOPAchrome. Additionally, this process is also related to two more proteins, i.e. oxygenase TYR-related protein 1 (TYRP1), and dopachrome tautomerase TYRP2 (or DCT). However, TYR located in the melanosomal membrane still stands as the key enzyme to initiate the whole process of melanogenesis. Due to some deficits, melanogenesis may emerge as hypo- or hyperpigmentation in the skin. High production of melanin in melanocytes leads to hyperpigmentationrelated skin disorders including freckles, melasma, melanoma, etc., that may cause displeasure in personal appearance and reduction of quality of life. Consequently, several melanogenesis inhibitors of synthetic and natural origins have been developed up to date, though most of them have been reported with serious side effects. For this reason, an extensive research is still going on to find novel and more effective melanogenesis inhibitors with less side effects. In this sense, particularly flavonoids, catechins, and stilbenes from plants have been a hope to discover new inhibitors which attract a great attention from scientists. In this review, promising natural products effective in melanogenesis inhibition will be scrutinized.
... Another derivate from the hydroxylation of resveratrol is piceatannol, present in grapes, passion fruit and peanut calluses [33]. Although this compound has been less studied than resveratrol due to its lower concentration in food, it has been reported to have a higher activity [41]. Thus, piceatannol also improves hepatic glycemic control by activating adenosine monophosphate-activated protein kinase (AMPK) through phosphorylation while ameliorating serum lipid profile in mice inhibiting the lipogenic flux mediated by ACC and fatty acid synthase (FAS) expression [42] Piceatannol-mediated AMPK phosphorylation also induces autophagy, a process reported to be dysregulated in NAFLD [43]. ...
Article
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Current food tendencies, suboptimal dietary habits and a sedentary lifestyle are spreading metabolic disorders worldwide. Consequently, the prevalence of liver pathologies is increasing, as it is the main metabolic organ in the body. Chronic liver diseases, with non-alcoholic fatty liver disease (NAFLD) as the main cause, have an alarming prevalence of around 25% worldwide. Otherwise, the consumption of certain drugs leads to an acute liver failure (ALF), with drug-induced liver injury (DILI) as its main cause, or alcoholic liver disease (ALD). Although programs carried out by authorities are focused on improving dietary habits and lifestyle, the long-term compliance of the patient makes them difficult to follow. Thus, the supplementation with certain substances may represent a more easy-to-follow approach for patients. In this context, the consumption of polyphenol-rich food represents an attractive alternative as these compounds have been characterized to be effective in ameliorating liver pathologies. Despite of their structural diversity, certain similar characteristics allow to classify polyphenols in 5 groups: stilbenes, flavonoids, phenolic acids, lignans and curcuminoids. Herein, we have identified the most relevant compounds in each group and characterized their main sources. By this, authorities should encourage the consumption of polyphenol-rich products, as most of them are available in quotidian life, which might reduce the socioeconomical burden of liver diseases.
... Pic belongs to the natural polyphenolic compound family, and has been confirmed to be a naturally occurring hydroxylated analogue of resveratrol (34). due to the similarity in the molecular structure with resveratrol, Pic was hypothesized to exert similar pharmacological properties. ...
Article
Reperfusion is a critical therapeutic intervention used following acute ischemic stroke; however, it may cause cerebral ischemia/reperfusion injury (CIRI) and aggravate brain damage. Piceatannol (Pic), a hydroxylated analog of resveratrol, has been reported to exhibit anti‑inflammatory effects. However, the detailed molecular mechanisms and its effects on CIRI have not been sufficiently assessed, and, to the best of our knowledge, current methods of prevention of CIRI are limited. The aim of the present study was to investigate the effects of Pic on improving neurological function in a mouse model of CIRI. For the animal experiments, 8‑week‑old C57BL/6 mice were raised and randomly grouped, and an in vivo model of CIRI was established. Mice were administered a low (10 mg/kg/day) or high‑dose (20 mg/kg/d) of Pic 1 h after CIRI orally and once daily for the next 6 days. Neurological dysfunction was assessed using a modified neurological severity score and a rotarod test 1 week after CIRI establishment, and the cognitive status of the mice was assessed using a Morris water maze. Hematoxylin and eosin staining was used to evaluate the histopathological changes. The expression levels of sirtuin 1 (Sirt1), FoxO1, cleaved caspase‑3 (CC‑3), Bax and Bcl‑2 were measured using western blotting. Intracellular reactive oxygen species (ROS) generation, antioxidant enzymes [superoxide dismutase, glutathione (GSH) peroxidase and catalase] and non‑enzymatic antioxidants (GSH) were also detected using spectrophotometry. After inhibition of the Sirt1/FoxO1 pathway, a TUNEL assay was used for the detection of apoptotic cells in vitro and in vivo. The co‑localization of neuron‑specific nuclear protein and CC‑3 was assessing using immunofluorescent staining. Pic improved neurological functions and ameliorated hippocampal neuronal pathology following CIRI. In addition, the expression levels of CC‑3 and Bax and intracellular ROS levels were increased, while levels of antioxidant and non‑enzymatic enzymes were decreased in the mouse model of CIRI. Low and high doses of Pic significantly decreased ROS production and the expression levels of apoptosis‑related proteins, but increased antioxidant enzyme levels. However, a high‑dose of Pic did not result in increased levels of non‑enzymatic enzymes. Furthermore, low and high doses of Pic treatment significantly activated the Sirt1/FoxO1 pathway. Following inhibition of the Sirt1/FoxO1 pathway, the percentage of TUNEL‑positive cells and expression of CC‑3 were increased, and CC‑3 was enriched in neurons. The antioxidant effects of Pic were blocked by inhibition of Sirt1 in vitro and in vivo. In conclusion, these results suggested that Pic may exert a neuroprotective effect against in hippocampal neurons via the Sirt1/FoxO1 pathway.
... In this regard, they have been able to identify considerable amounts of chlorogenic and rosmarinic acids, together with quercetin, in the ethyl acetate fraction, while reasonable amounts of kojic and gallic acids were found in the aqueous seed fraction (Lourith and Kanlayavattanakul, 2013). In the same study, the presence of scirpusin B and stilbene piceatannol was reported, simply and dimerically in passion fruit seeds, and a previous study the compound was reported as the majority phenol in gulupa seeds (Matsui et al., 2010). ...
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This study aimed to assess the anti-aging potential of the ethanol extract of Passiflora edulis f. edulis Sims seeds, through in vitro determination of antioxidant activity and inhibition assays of some enzymes related to skin aging. Furthermore, using in silico methods (docking and molecular dynamics), were established the affinity of the majority compounds of the extract on the target enzymes, ending with the prediction of drug-likeness properties. The extract showed a high total phenolic content, represented mainly by flavonoids and phenolic acids, as well as a considerable antioxidant potential measured through the DPPH, FRAP and ORAC methods. In the inhibition assays of the enzymes collagenase, elastase and tyrosinase, IC50 values presented were optimal. Docking studies demonstrated marked binding ability of the extract constituients (specially, fisetin, galangin and S-eriodictyol) to the Collagenase and Tyrosinase. Molecular dynamics validated the stability and rationality of these molecular docking studies, MM/PBSA calculations provide strong evidence for both their specific heavy binding and how enzyme-ligand complex stabilized inside the catalytic domain, and drug-likeness studies showed suitable dermato-pharmacokinetics indices for most of components of extract. Findings from this study suggest that ethanol extract of P. edulis has a great potential as an anti-aging agent.
... Passion fruit seeds contain high amounts of piceatannol (3,4,3',5'-tetrahydroxytans-stilbene) in their phenolic composition. Piceatannol is a resveratrol hydroxylate which presents strong antioxidant activity (Uchida-Maruki et al., 2015;Matsui et al., 2010). According to the reported data, the high piceatannol content in passion fruit seeds exerts positive effects on cultured dermal cells with respect to melanogenesis inhibition and collagen synthesis. ...
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The wild passion fruit species Passiflora setacea, Passiflora alata, and Passiflora tenuifila are native to the Brazilian biomass. The seed waste generated from the extraction of passion fruit juice contains functional polyunsaturated fatty acids and phenolic compounds. The aims of this study were to obtain lipids and natural antioxidants from passion fruit seeds. Passion seed oils were extracted using a lab-scale continuous press and their oxidative stability was evaluated using the Rancimat® method. Higher antioxidant extract capacity was observed when using an ethanol-water solution (70:30) at 45 ºC. In these cases, the total phenolic contents expressed as gallic acid equivalents from P. setacea, P. alata, and P. tenuifila cakes were approximately 1800, 600 and 900 mg·100g−1 of extract. Induction periods increased up to two-fold when adding these extracts to their respective seed oil. Therefore, passion fruit seed extract can contribute to increasing the oxidative stability of polyunsaturated oils.
... Abnormal melanogenesis causes skin pigment disorders, such as freckles and erythema [45]. Because tyrosinase is the key enzyme in the process of melanin biosynthesis, a tyrosinase inhibitor may be a potential candidate for inhibiting or reducing melanin biosynthesis. ...
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Previous studies suggested that fucoidan with a molecular weight of 102.67 kDa, isolated from Hizikia fusiforme, possesses strong antioxidant activity. To explore the cosmeceutical potential of fucoidan, its anti-photoaging and anti-melanogenesis effects were evaluated in the present study. The anti-photoaging effect was investigated in ultraviolet (UV) B-irradiated human keratinocytes (HaCaT cells), where fucoidan effectively reduced the intracellular reactive oxygen species level and improved the viability of the UVB-irradiated cells without any cytotoxic effects. Moreover, fucoidan significantly decreased UVB-induced apoptosis in HaCaT cells by regulating the protein expression of Bax, Bcl-xL, PARP, and Caspase-3 in HaCaT cells in a concentration-dependent manner. The anti-melanogenesis effect of fucoidan was evaluated in B16F10 melanoma cells that had been stimulated with alpha-melanocyte-stimulating hormone (α-MSH), and fucoidan treatment remarkably inhibited melanin synthesis in α-MSH-stimulated B16F10 cells. Further studies indicated that fucoidan significantly suppressed the expression of tyrosinase and tyrosinase-related protein-1 and -2 (TRP-1 and-2) in B16F10 cells by down-regulating microphthalmia-associated transcription factor (MITF) through regulation of the ERK–MAPK (extracellular signal regulated kinase-mitogen activated protein kinase) pathway. Taken together, these results suggest that fucoidan isolated from H. fusiforme possesses strong anti-photoaging and anti-melanogenesis activities and can be used as an ingredient in the pharmaceutical and cosmeceutical industries.
... The literature reports that passion fruit seed present higher amounts of phenolic compounds and the main component is the PIC [22,23,29,30]. The yellow passion fruit (P. ...
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Climatic Changes and Zoonotic Diseases: Toplum sağlığı açısından yüksek risk taşıyan zoonoz hastalıklar yanında, yüksek prevalansa sahip enfeksiyöz ajanlar iklim değişikliği bağlamında tıbbi öneme sahiptir. İklim değişikliği süreci birçok patojenin bulaşmasını ve salgınların ortaya çıkma ihtimalini arttırmaktadır. Tıbbi önemi yeni anlaşılan veya yeniden dikkat çeken bazı patojenlerin, iklim değişikliklerine bağlı olarak, alışılan veya bilinenlerin dışında farklı sonuçlara neden olabilecek yeni adaptasyonlar geçirdikleri tespit edilmiştir.
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Passiflora species are widely used in folk medicine due to their sedative and anxiolytic activities; however, scientific studies also showed different biological activities (antioxidant, anti-inflammatory, antidiabetic and antimicrobial). The present study aimed to characterize the phytochemical profile of P. cincinnata hydroethanolic extract, evaluate its antioxidant and antiglycation activities and evaluate in silico molecular docking of its main flavonoids. Phytochemical characterization was performed by quantification of total polyphenols and flavonoids content, and High Performance Liquid Chromatography-Mass Spectrometry (HPLC-MS) analysis. Antioxidant activity was determined by 2,2-Diphenyl-1-picrylhydrazyl (DPPH), Ferric reducing antioxidant power (FRAP), Nitric oxide (NO) and Thiobarbituric acid reactive species (TBARS) tests. Antiglycation activity was determined by Relative Electrophoretic Mobility (REM) and free amino groups assays. P. cincinnata presented total polyphenols (62 mg gallic acid equivalent (GAE) g⁻¹ dry weight (DW)) and flavonoids (57 mg rutin equivalent (RE) g⁻¹ DW), besides HPLC-MS showed the presence of different flavonoids glucoside, mainly vitexin and orientin. The extract presented antioxidant activity by DPPH (76.60%), FRAP (276.70 μM trolox equivalent (TE) g⁻¹ DW), TBARS (80.30% inhibition) and NO (10.10 μM mL⁻¹ nitrite formed). REM demonstrated that extract presents antiglycation activity similar to Bovine serum albumin treated with Aminoguanidine; additionally, it showed 22% free amino groups. In silico assay demonstrated that orientin exhibited the highest interaction with DNA and the best docking score with elastase and collagenase. Therefore, the present study showed the protective properties of P. cincinnata hydroethanolic extract against oxidative stress and glycation. It also showed the presence of polyphenols and flavonoids, and their interaction with DNA and enzymes.
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In the present study, we explored the properties of Bacillus siamensis-fermented kelp as a raw material for the preparation of cosmetics. We found that the content of polysaccharide in the kelp fermentation broth was 343.90 ± 8.63 mg/g, the content of fucose was 127.55 ± 9.55 mg/g, and the content of alginic acid was 322.00 ± 14.14 mg/g. The scavenging rate of DPPH free radicals of the kelp fermentation broth was 95.08 ± 1.60 %, showing good antioxidant capacity. Moreover, high tyrosinase activity inhibition could suppress hyperpigmentation. Furthermore, morphological observation, CCK-8 assay, and would healing assay were used to test the anti-wrinkle and skin-repairing effects of the fermentation broth on skin cells. The results show that Bacillus siamensis fermentation broth of kelp at a dilution of 1:1000 could effectively promote the growth of skin cells HaCaT and HFF-1, showing good skin-repairing and anti-wrinkle effects. Collectively, the Bacillus siamensis fermentation broth of kelp could be used as a cosmetic raw material.
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An improved analytical strategy based on the QuEChERS extraction method combined with high-performance liquid chromatography with diode array detector (HPLC-DAD) was developed and validated for the first time for piceatannol determination in passion fruit seeds. The method showed a limit of quantification of 160 µg kg⁻¹, good linearity (r² = 0.9957), recoveries in the range of 82–102% with good precision (RSD < 9%) and low matrix effect (+17%). The new method was successfully applied for piceatannol determination in four passion fruit seeds species: Passiflora edulis Sims “Flavicarpa,” P. edulis “Sims,” Passiflora allata Curtis, and Passiflora ligularis Juss; for the last two species for the first time. Among them, the higher amounts of piceatannol were found in the seeds of P. allata Curtis and P. edulis “Sims”: 20.8 ± 0.4 and 14.6 ± 0.2 mg kg⁻¹, respectively. Antioxidant activity was also evaluated and, in general, the antioxidant potential was stronger the higher the piceatannol concentration in the passion fruit seeds extracts. The obtained results highlight that passion fruit seeds are a rich source of piceatannol, boosting new applicability for these by-products, and indicating that the QuEChERS method is a powerful analytical strategy for piceatannol determination.
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The potential role of plant-based foods in the promotion of skin health is an emerging area of nutrition research. Plant-based foods are rich in bioactive compounds, including vitamin C, vitamin E, beta-carotene, polyphenols, and phenolic acids, which can contribute to oxidant defense, lower inflammation, and promote structural support of the skin. Epidemiological studies have associated higher intakes of select fruits and vegetables with positive skin health.1,2 Beneficial effects of certain fruits, vegetables, nuts, legumes, and polyphenolic-rich beverages on the skin have been reported, with each of these providing a unique phytochemical composition. While most studies use extracts, this review will focus on data from whole foods and minimally processed products. Collectively, the evidence to date suggests a promising future for plant-based dietary interventions that promote skin barrier health and function. However, additional research is required to address issues such as the optimal quality and duration of intake as well as potential mechanisms. Studies in the above areas will help formulate specific targeted dietary recommendations.
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Background: Striae distensae is a skin disorder that causes cosmetic and psychological problems. Purple passion fruit (Passiflora edulis Sims var. Edulis) is widely cultivated, especially in North Sumatra. The seeds are abundant and unused industrial waste. Purple passion fruit seeds contain piceatannol, ascorbic acid, flavonoids, resveratrol, hydroalcohols and sterols which play a role in the repair of striae distensae through anti-inflammatory mechanisms, increase fibroblast proliferation and collagen production, increase crosslinking between collagen fibers and moisturizers. Objective: To determine the effect of 6% purple passion fruit (Passiflora edulis Sims var. Edulis) seed extract cream on striae distensae. Subjects and Methods: This study is a pre-experimental clinical trial with a pretest-posttest research design on 40 subjects with striae distensae. Diagnosis was confirmed by history and clinical evaluation using the Manchester scar scale before and after administration of 6% purple passion fruit extract cream at weeks 0, 2, 4, 6, 8. Adverse effects were recorded during the study and satisfaction levels were assessed at the end. Results: The majority of subjects' ages ranged from 29 to 39 years (72.5%). There was a significant reduction in Manchester scar scale in striae distensae, both after being given a 6% purple passion fruit extract cream or a combination of 1% tretinoin cream for 8 weeks, with a mean reduction of 25% (p = 0.000). Striae distensae after being given 6% purple passion fruit extract cream compared to 6% purple passion fruit extract cream combined with 1% tretinoin cream, there was no significant difference (p = 0.791). From a total of 40 subjects, none experienced side effects (0%). As many as 57.5% of the subjects showed a good level of satisfaction. Conclusion: The use of 6% purple passion fruit seed extract cream can improve the appearance of striae distensae without side effects and the level of satisfaction is good.
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SARS-CoV-2 main protease is a possible target for protection against viral infection. This study examined the inhibitory effect of food phytochemicals on the main protease of SARS-CoV-2 by determining a cleaved product after chromatographic separation. First, 37 phytochemicals, including glycosides and metabolites, were screened at 20 µM; epigallocatechin gallate, myricetin, theaflavin, herbacetin, piceatannol, myricitrin, and isothiocyanates inhibited the enzyme in varying degrees. The IC50 values were estimated from 0.4 to 33.3 µM against the 0.5-µM enzyme. The dose-dependent adduction of epigallocatechin gallate and myricetin was confirmed by quinone staining of protein blotted onto a membrane. The enzyme activity was decreased by increasing the concentration of the two phytochemicals, accompanied by increasing the respective adducted molecule estimated by intact mass spectrometry. Reduced glutathione canceled the formation of conjugate and the inhibitory effect of epigallocatechin gallate or myricetin on the enzyme, suggesting that the formation of the quinone moiety in the phytochemicals is critical for the inhibition. The covalent binding of epigallocatechin gallate or myricetin to the cysteine residue at the active site was confirmed by analyzing peptides from the chymotrypsin-digested main protease.
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Defense compounds generally inhibit microbial colonization of plants. In this study, we examined the presence of endophytes in Passiflora edulis seeds that accumulate resveratrol and piceatannol at extremely high levels as defense compounds. Interestingly, although no microbial colonies appeared on an agar growth medium from the cut or homogenized seeds, colonies were generated from cut seedlings derived from the seeds. A total of 19 bacterial strains were isolated, of which 15 were classified as Gram-positive. As we hypothesized that extremely high levels of piceatannol in the seeds would inhibit the growth of endophytes cultured directly from the seeds, we examined the antimicrobial activity of this compound against the isolated bacteria. Piceatannol exerted bacteriostatic rather than bactericidal effects on most of the bacteria tested. These results suggest that the bacteria remain static in the seeds due to the presence of piceatannol and are transmitted to the seedlings during the germination process, enabling colonies to be established from the seedlings on the agar medium. We also investigated the biocatalytic activity of the isolated bacteria toward resveratrol and piceatannol. One bacterium, Brevibacterium sp. PE28-2, converted resveratrol and piceatannol to their respective derivatives. This strain is the first endophyte shown to exhibit such activity.
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Apart from being food, passion fruit (Passiflora edulis Sims) offers seeds to be used as an oil source, and the residual seed cake from oil extraction contains piceatannol, a molecule that can prevent skin damages. In this work, microwave-assisted extraction (MAE) was evaluated as a technique for the preparation of piceatannol-rich seed cake extracts, and its performance was compared to the conventional Soxhlet extraction. MAE and Soxhlet exhibited different selectivities for the seed cake compounds. A sequential MAE at 87 °C, with 70% EtOH, for 30 min each cycle, provided a fine brown powder with 27.17 ± 0.9 μg of piceatannol per mg of the extract, while Soxhlet extraction for 120 min resulted in a dark lumpy extract containing 13.03 ± 0.4 μg mg⁻¹. Thus, MAE was shown to be a promising alternative to produce a passion fruit seed extract for cosmetic purposes, adding value to a residue from the passion fruit chain by providing a faster extraction and a more color friendly and easier-to-handle product with higher levels of piceatannol in comparison to the conventional method.
Chapter
Bioactive compounds have been an important subject in food science and technology because of their potential benefits to health and wellness. Given that modern lifestyles have a profound influence on public health and that these bioactive substances are widely distributed in foods of all sources, food processing is an adequate means to increase their bioavailability and prevent losses thus contributing to the control of chronic diseases. In some cases, processing can be instrumentalto make a substance bioactive, as are the cases of isoflavones, isothiocyanates and thiosulfinates, for which thermal and mechanical treatments are necessary to make them available. In this chapter the known chemical changes responsible for the generation and alterations of glucosinolates, thiosulfinates, flavonoids, stilbenes and coumarins are presented and discussed with a focus on the role of processing techniques and their impact on the health properties.
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The present research article reports the appraisal of antimicrobial and antioxidant activities of Ag, Fe and bimetallic Fe-Ag nanoparticles prepared using aqueous leaf extract of Passiflora edulis. The UV–Visible spectroscopy confirms the formation of nanoparticles by exhibiting maximal absorption peak at 436 nm. The Fourier transform infrared spectroscopy vibrational bands confirm the phytochemicals accountable for the reduction of nanoparticles. The X-ray diffraction used in the study of crystalline nature of nanoparticles. The Debye-Scherrer equation used to calculate average particle sizes of Ag, Fe and bimetallic Fe-Ag nanoparticles were found to be 34 nm, 500 nm, 60 nm respectively. The Scanning electron microscopy was (SEM) used to the study surface morphology of the Ag, Fe and bimetallic Fe-Ag nanoparticles. The Energy dispersive spectroscopy is used to analyze the elemental signal profile which is automatically done by coupled SEM. Transmission electron microscopy images depict the monoclinic, isotropic, spherical shaped particles. The characterized Ag, Fe and bimetallic Fe-Ag nanoparticles used in the investigation of antibacterial studies against harmful bacteria Escherichia coli and Bacillus subtilis. The antifungal action performed against human pathogenic fungi Aspergillus flavus, phytopathogenic fungi Sclerotium rolfsii and Rhizoctonia solani. Antioxidant activity of Ag, Fe and bimetallic Fe-Ag nanoparticles was successfully performed using DPPH and ABTS radical scavenging assays.
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Aging induces drastic changes in muscle mass and function (sarcopenia); however, the detailed mechanisms underlying sarcopenia remain poorly understood. Recent studies suggested that age-related increases in oxidative stress induce muscle atrophy. In this study, we investigated the effect of 6-month supplementation of antioxidants, specifically piceatannol (PIC) and enzymatically modified isoquercitrin (EMIQ), on age-related physiological changes, including skeletal muscle weight and quality, in 25-month-old (OLD) mice, compared to in 4-month-old (young, YNG) C57BL/6J mice. Muscle weight corrected by body weight significantly declined in OLD mice, compared to in YNG mice. The control OLD mice also showed changes in the expression of genes related to muscle fiber type, reduced locomotor activity, and increased oxidative stress markers in blood. Consistent with the muscle weight and quality changes, whole-body fat oxidation during sedentary conditions and exercise periods in control OLD mice was significantly lower than that in YNG mice. Interestingly, compared to the control OLD mice, the PIC- or EMIQ-fed OLD mice showed higher fat oxidation. Furthermore, EMIQ, but not PIC, increased locomotor activity, the expression of genes encoding antioxidant enzymes, and suppressed the carbonylated protein in the skeletal muscle of OLD mice. These results suggested that chronic antioxidant intake could alleviate aging-related muscle function changes.
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Objetivo: Avaliar o efeito do extrato das folhas da Passiflora edulis na cicatrização da pele em ratos, especificamente na área da lesão e na proliferação de fibroblastos. Materiais e método: Estudo experimental realizado com 54 ratos da linhagem Wistar, machos, adultos, divididos igualmente em três grupos. A indução das lesões em formato circular na região dorso-cervical foi realizada com o auxílio de um punch trepano de 8 mm. As lesões do grupo de controle foram higienizadas diariamente com água filtrada e sabonete vegetal glicerinado de pH neutro. Os outros dois grupos, além da higienização diária, receberam tratamento com creme contendo extrato a 20 % das folhas da Passiflora edulis, e creme-base sem extrato a 20 % das folhas da Passiflora edulis, respectivamente. No 1°, 4°, 7° e 14° dia de tratamento foram obtidas imagens para cálculo da área de lesão. No 4°, 7° e 14° dia de tratamento foram coletados espécimes para análises histológicas. Resultados: Não foram encontradas diferenças estatisticamente significativas entre os grupos experimentais com relação à comparação de médias da área de lesão e de proliferação de fibroblastos. Conclusões: O uso tópico do extrato a 20 % das folhas da Passiflora edulis não apresentou efeito na área de lesão e na proliferação de fibroblastos na cicatrização da pele em ratos.
Article
Background: Purple variant of passion fruit (Passiflora edulis Sims var. edulis) is a tropical plant commonly used in the beverage industry. The seeds have high content of linoleic acid and piceatannol which has been reported and showed antibacterial, anti-inflammatory, and antioxidant activities. However, there is no report regarding its effect on acne vulgaris. Objective: To determine the efficacy of topical use of Passiflora edulis Sims var. edulis seeds extract on acne vulgaris. Methods: In this open-label uncontrolled trial, 45 subjects with acne vulgaris were given passion fruit purple variant seeds extract 10% cream for 8 weeks. Noninflammatory, inflammatory, and total acne lesions count along with ultraviolet-induced red fluorescence (UVRF) measurement were done at weeks 0, 2, 4, 6, and 8. All reported adverse events were documented, and patient satisfaction rates were determined at week 8. Paired T-test and Wilcoxon test were done with P ≤ 0.05 indicating significance. Results: There were significant reductions in noninflammatory (80.9%), inflammatory (71.1%), and total (73%) lesion count after 8 weeks of the cream application (P < 0.001). Significant reduction in UVRF spot quantity (36%) and percentage area (45.9%) were found at week 8 (P < 0.001). Only 2.2% of subjects experienced an adverse event of mild and transient peeling. Most of the subjects (77.8%) noticed significant improvement in their acne vulgaris and expressed good satisfaction rate. Conclusion: Topical use of passion fruit purple variant seeds extract improves acne vulgaris with reduction in lesion counts and UVRF, minimal adverse events, and good satisfaction rate. Additional prospective studies are required.
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We recently demonstrated that human melanocyte proliferation and differentiation could be stimulated by endothelin (ET) derivatives via a receptor-mediated signal transduction pathway (Yada, Y., Higuchi, K., and Imokawa, G. (1991) J. Biol. Chem. 266, 18352-18357). We show here that the growth factors for human melanocytes are produced and secreted by the surrounding cells, namely human keratinocytes for ET-1 and Big-ET-1. Northern blots have revealed the presence of ET-1 gene transcripts in proliferating human keratinocytes. The ET-1 production by human keratinocytes increased after irradiation with ultraviolet B (UVB) in a dose-dependent manner, accompanied by the significant secretion of interleukin 1alpha (IL-1alpha). Among the cytokines related to UVB-induced cellular reactions and keratinocyte growth, only IL-1alpha and -1beta stimulated the secretion of ET-1 and Big-ET-1 but not of ET-3 and Big-ET-3 in a time-dependent manner. Northern blots for IL-1alpha-stimulated or UVB-exposed human keratinocytes revealed that production of ET-1 gene transcripts markedly increased (by about 300 or 1,200%) with constant levels of beta-actin gene transcripts. In a parallel study, the medium conditioned by UVB-exposed human keratinocytes elicited a significant anti-ET-1 antibody-suppressible increase in DNA synthesis by cultured human melanocytes in a UV dose-dependent manner, which was associated with a marked and rapid (80 s) increase in the intracellular calcium level upon incubation with human melanocytes. These studies suggest that ETs produced and secreted by keratinocytes play an essential role in the maintenance of melanocyte proliferation and UV hyperpigmentation in the epidermis.
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Piceatannol (trans-3,3',4,5'-tetrahydroxy-stilbene) is a natural stilbene occurring in a number of plant species, and it has been shown to have beneficial effects on human health. The compound can seldom be consumed by humans, because it occurs in non-food plants, or in non-edible or-gans. Here we show for the first time that grapes (Vitis vinifera L. cv. Cabernet Sauvignon) have significant amounts of piceatannol (0.052 mg g -1 fresh wt). The identity of piceatannol was confirmed by HPLC and LC-MS.
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Ultraviolet (UV) irradiation accelerates formation of ceramide through hydrolysis of sphingomyelin and de novo synthesis. Here, we investigated the effects of ceramide on UV-induced matrix metalloproteinase-1 (MMP-1) expression in human dermal fibroblasts. Our results showed that acidic-sphingomyelinase (aSMase) and MMP-1 mRNA expression were increased by UV irradiation. Treatment of D609 (aSMase inhibitor) decreased the level of basal and UV-induced MMP-1 expression. On the other hand, basal and UV-induced MMP-1 expression was increased through induction of intracellular ceramide by D-MAPP, a ceramidase inhibitor. Our results also showed that MMP-1 protein expression was dose-dependently increased by C(2)-ceramide or SMase treatment. The activation of ceramide pathway by C(2)-ceramide enhanced phosphorylation of signal transducer and activators of transcription-1 (STAT-1), whereas ceramide-induced MMP-1 expression was potently prevented by piceatannol; Janus kinase (JAK1) inhibtor; and WHI-P131, a specific inhibitor of JAK3; but not by AG490, JAK 2 inhbitor, in human dermal fibroblasts. We also found that UV induced the phosphorylation of STAT-1, and UV-induced MMP-1 expression was significantly decreased by JAK1 inhibitor, piceatannol. Overall, we demonstrate that induction of intracellular ceramide by UV may activate MMP-1 gene expression via JAK1/STAT-1 pathway. Therefore, we suggest that targeted modulation of the ceramide signaling pathway may offer a novel therapeutic approach for inhibiting MMP-1 expression, which is a causing gene of skin aging.
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We recently demonstrated that human melanocyte proliferation and differentiation could be stimulated by endothelin (ET) derivatives via a receptor-mediated signal transduction pathway (Yada, Y., Higuchi, K., and Imokawa, G. (1991) J. Biol. Chem. 266, 18352-18357). We show here that the growth factors for human melanocytes are produced and secreted by the surrounding cells, namely human keratinocytes for ET-1 and Big-ET-1. Northern blots have revealed the presence of ET-1 gene transcripts in proliferating human keratinocytes. The ET-1 production by human keratinocytes increased after irradiation with ultraviolet B (UVB) in a dose-dependent manner, accompanied by the significant secretion of interleukin 1 alpha (IL-1 alpha). Among the cytokines related to UVB-induced cellular reactions and keratinocyte growth, only IL-1 alpha and -1 beta stimulated the secretion of ET-1 and Big-ET-1 but not of ET-3 and Big-ET-3 in a time-dependent manner. Northern blots for IL-1 alpha-stimulated or UVB-exposed human keratinocytes revealed that production of ET-1 gene transcripts markedly increased (by about 300 or 1,200%) with constant levels of beta-actin gene transcripts. In a parallel study, the medium conditioned by UVB-exposed human keratinocytes elicited a significant anti-ET-1 antibody-suppressible increase in DNA synthesis by cultured human melanocytes in a UV dose-dependent manner, which was associated with a marked and rapid (80 s) increase in the intracellular calcium level upon incubation with human melanocytes. These studies suggest that ETs produced and secreted by keratinocytes play an essential role in the maintenance of melanocyte proliferation and UV hyperpigmentation in the epidermis.
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Resveratrol is a cancer preventative agent that is found in red wine. Piceatannol is a closely related stilbene that has antileukaemic activity and is also a tyrosine kinase inhibitor. Piceatannol differs from resveratrol by having an additional aromatic hydroxy group. The enzyme CYP1B1 is overexpressed in a wide variety of human tumours and catalyses aromatic hydroxylation reactions. We report here that the cancer preventative agent resveratrol undergoes metabolism by the cytochrome P450 enzyme CYP1B1 to give a metabolite which has been identified as the known antileukaemic agent piceatannol. The metabolite was identified by high performance liquid chromatography analysis using fluorescence detection and the identity of the metabolite was further confirmed by derivatisation followed by gas chromatography–mass spectrometry studies using authentic piceatannol for comparison. This observation provides a novel explanation for the cancer preventative properties of resveratrol. It demonstrates that a natural dietary cancer preventative agent can be converted to a compound with known anticancer activity by an enzyme that is found in human tumours. Importantly this result gives insight into the functional role of CYP1B1 and provides evidence for the concept that CYP1B1 in tumours may be functioning as a growth suppressor enzyme. British Journal of Cancer (2002) 86, 774–778. DOI: 10.1038/sj/bjc/6600197 www.bjcancer.com © 2002 Cancer Research UK
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Orally administered methanol extract of Passiflora edulis rind (10 mg/kg or 50 mg/kg) or luteolin (50 mg/kg), which is one of consistent polyphenols of the extract, significantly lowered systolic blood pressure in spontaneously hypertensive rats (SHRs). Quantitative analysis by liquid chromatography tandem mass spectrometry (LC-MS/MS) showed that the extract contained 20 microg/g dry weight of luteolin and 41 microg/g dry weight of luteolin-6-C-glucoside. It also contained gamma-aminobutyric acid (GABA, 2.4 mg/g dry weight by LC-MS/MS or 4.4 mg/g dry weight by amino acid analysis) which has been reported to be an antihypertensive material. Since the extract contained a relatively high concentration of GABA, the antihypertensive effect of the extract in SHRs might be due mostly to the GABA-induced antihypertensive effect and partially to the vasodilatory effect of polyphenols including luteolin.
Article
Over the years there has been much debate as to whether α-MSH has a role as a pigmentary hormone in humans. There are two main reasons for this. First, despite the observations in the 1960s that α-MSH increased skin darkening in humans, there are reports that the peptide has no effect on melanogenesis in cultured human melanocytes. Second, the human pituitary, unlike that of most mammals, secretes very little α-MSH and circulatory levels of the peptide in humans are extremely low. However, there is now evidence from several groups that α-MSH is capable of stimulating melanogenesis in cultured human melanocytes. Rather than producing an overall increase in melanin production, it appears that the peptide acts specifically to increase the synthesis of eumelanin. Such an action could well explain the previously observed skin darkening effects of α-MSH. It is also now known that α-MSH is not produced exclusively in the pituitary but has been found at numerous sites, including the skin where it is produced by several cell types. Related Proopiomelanocortin (POMC) peptides such as ACTH are also produced in human skin. The ACTH peptides act at the same receptor (MC-1) as α-MSH and certain of these would appear to be more potent than α-MSH in stimulating melanogenesis. The ACTH peptides are also present in greater amounts than α-MSH in human epidermis and it is likely that they play an important role in regulating pigmentary responses. These POMC peptides are released from keratinocytes in response to ultraviolet radiation (UVR) and it has been proposed that they serve as paracrine factors in mediating UV induced pigmentation. Their production by keratinocytes could therefore be critical in determining pigmentary responses and any changes in the availability of these POMC peptides might explain the variations in tanning ability seen in different individuals. However, the possibility that tanning ability is also dependent upon differences at the level of the MC-1 receptor cannot be ruled out and it has been suggested that an inability to tan may depend upon the presence of non-functional changes at the MC-1 receptor. α-MSH does, of course, affect human melanocytes in several ways and its stimulation of melanogenesis could be the consequence of some other fundamental action in the melanocyte. The peptide also has many other target sites in the skin and while it may have a role in regulating skin pigmentation in humans, it should not be viewed solely as a pigmentary peptide. α-MSH clearly has many different actions and its primary role in the skin may be to maintain homeostasis.
Article
The following 13 carotenoids from yellow passion fruit (Passiflora edulis) were conclusively identified: phytoene, phytofluene, ζ-carotene (principal carotenoid), neurosporene, β-carotene, lycopene, prolycopene, monoepoxy-β-carotene, β-cryptoxanthin, β-citraurin, antheraxanthin, violaxanthin, and neoxanthin. Electron impact mass spectrometry, complemented by UV−visible spectrophotometry and co-chromatography, besides 1H and 13C nuclear magnetic resonance spectroscopy for prolycopene, was used for this purpose. Seven of the carotenoids identified are reported as passion fruit carotenoids for the first time. Keywords: Carotenoids; passion fruit; identification
Article
Recent studies have shown that dietary fiber and polyphenols of vegetables and fruits improve lipid metabolism and prevent the oxidation of low density lipoprotein cholesterol (LDL-C), which hinder the development of atherosclerosis. The goal of this study was to measure the total polyphenol and dietary fiber contents of some tropical fruits (i.e., pineapple, wax apple, rambutan, lichi, guava, and mango) and compare the results to the content of these substances in the better characterized persimmon. It was found that lichi, guava, and ripe mango (cv. Keaw) have 3.35, 4.95, and 6.25 mg of total polyphenols in 100 g fresh fruit, respectively. This is significantly higher than in persimmon, pineapple, wax apple, mature green mango, and rambutan [P < 0.0005 for pineapple (Smooth Cayene variant), wax apple, persimmon, rambutan, mature green mango (cv. Keaw); the value of P < 0.001 is found only for pineapple (Phuket, Queen variant)]. The same relationship was observed for the contents of gallic acid and of dietary fiber. It can be supposed that among the studied fruit, lichi, guava, and ripe mango may be preferable for dietary prevention of atherosclerosis.
Article
The cortex of 14 French apple varieties (12 cider and 2 juice varieties), one English cider variety, and one dessert apple (i.e., Golden Delicious) were studied for their polyphenol composition. Total polyphenols were assayed by the Folin-Ciocalteu method, and the precise polyphenolic composition (monomeric catechins, proanthocyanidins, hydroxycinnamic acids, and dihydrochalcones) was obtained by HPLC following thiolysis. ESI-MS and ESI-MS/MS analyses showed that chlorogenic acid and p-coumaroylquinic acid were methylated under the conditions of thiolysis. Depending on the variety, the global polyphenol concentration varied from 1 to 7 g per kilogram of fresh cortex. Cider varieties globally showed a higher polyphenol concentration than the dessert apple Golden Delicious, bitter varieties being the more concentrated. The proportion of the polyphenol classes varied greatly from one cultivar to another. For all varieties, procyanidins were always the predominant class. They were mainly constituted of (-)-epicatechin units with a small proportion of (+)-catechin as a terminal unit. The average degree of polymerization ranged between 4.2 and 7.5 depending upon the variety with an exception for the sharp varieties Guillevic and Avrolles which showed significant concentrations of procyanidins with DPn of 40 and 50, respectively.
Article
Epidemiological, clinical and laboratory studies have implicated solar ultraviolet (UV) radiation in various skin diseases including, premature aging of the skin and melanoma and non-melanoma skin cancers. Chronic UV radiation exposure-induced skin diseases or skin disorders are caused by the excessive induction of inflammation, oxidative stress and DNA damage, etc. The use of chemopreventive agents, such as plant polyphenols, to inhibit these events in UV-exposed skin is gaining attention. Chemoprevention refers to the use of agents that can inhibit, reverse or retard the process of these harmful events in the UV-exposed skin. A wide variety of polyphenols or phytochemicals, most of which are dietary supplements, have been reported to possess substantial skin photoprotective effects. This review article summarizes the photoprotective effects of some selected polyphenols, such as green tea polyphenols, grape seed proanthocyanidins, resveratrol, silymarin and genistein, on UV-induced skin inflammation, oxidative stress and DNA damage, etc., with a focus on mechanisms underlying the photoprotective effects of these polyphenols. The laboratory studies conducted in animal models suggest that these polyphenols have the ability to protect the skin from the adverse effects of UV radiation, including the risk of skin cancers. It is suggested that polyphenols may favorably supplement sunscreens protection, and may be useful for skin diseases associated with solar UV radiation-induced inflammation, oxidative stress and DNA damage.
Article
Oxidative damage is involved in many chronic diseases including those cited as the major causes of death in Western societies such as cardiovascular disorders and cancer. Antioxidants may prevent these degenerative processes by various mechanisms including the scavenging of free radicals. Intake of antioxidant supplements is associated with preventing oxidative damages. This study investigated the absorption and antioxidant effects of a xanthone-rich mangosteen liquid in healthy human volunteers after the acute consumption of 59 mL of the supplement. The liquid contained mangosteen, aloe vera, green tea, and multivitamins. Results indicated that alpha-mangostin and vitamins B(2) and B(5) were bioavailable, with observed C(max) at t(max) of around 1 h. The antioxidant capacity measured with the oxygen radical absorbance capacity (ORAC) assay was increased with a maximum effect of 18% after 2 h, and the increased antioxidant level lasted at least 4 h. Overall, this study demonstrated the bioavailability of antioxidants from a xanthone-rich mangosteen product and its in vivo antioxidant effects.
Article
The intent was to isolate an antifungal protein from seeds of the passion fruit (Passiflora edulis) and to compare its characteristics with other antifungal proteins and bovine beta-lactoglobulin in view of its N-terminal amino acid sequence similarity to beta-lactoglobulin. The isolation procedure entailed ion-exchange chromatography on Q-Sepharose, hydrophobic interaction chromatography on Phenyl-Sepharose, ion-exchange chromatography on DEAE-cellulose, and FPLC-gel filtration on Superdex 75. The isolated 67-kDa protein, designated as passiflin, exhibited an N-terminal amino acid sequence closely resembling that of bovine beta-lactoglobulin. It is the first antifungal protein found to have a beta-lactoglobulin-like N-terminal sequence. Its dimeric nature is rarely found in antifungal proteins. It impeded mycelial growth in Rhizotonia solani with an IC(50) of 16 microM and potently inhibited proliferation of MCF-7 breast cancer cells with an IC(50) of 15 microM. There was no cross-reactivity of passiflin with anti-beta-lactoglobulin antiserum. Intact beta-lactoglobulin lacks antifungal and antiproliferative activities and is much smaller in molecular size than passiflin. However, it has been reported that hydrolyzed beta-lactoglobulin shows antifungal activity. The data suggest that passiflin is distinct from beta-lactoglobulin.
Article
To examine the possibility of luteolin as a whitening agent, we measured antioxidant activity using DPPH assay, NBT/XO assay and intracellular ROS scavengning assay and depigmenting activity using tyrosinase assay, alpha-MSH-induced melanin production in B-16 cells. Luteolin showed dose-dependent anti-oxidant activity in DPPH, NBT/XO and intracellular ROS assay. Also, luteolin directly inhibited xanthine oxidase activity in a dose-dependent manner. Although luteolin did not directly inhibit tyrosinase activity, it dose-dependently inhibited both tyrosinase activity and melanin production in B16 melanoma cells stimulated by 1 microM alpha-MSH. Luteolin dose-dependently inhibited cAMP levels in B16 melanoma cells stimulated by 1 microM alpha-MSH and 1 microM forskolin, which suggest that luteolin directly inhibits adenyl cyclase in B16 melanoma cells. Therefore, these results suggest that whitening activity of luteolin may be due to the inhibition of adenyl cyclase involved in the signal pathway of alpha-MSH in B16 melanoma cells.
Article
The acai berry is the fruit of the acai palm and is traditionally consumed in Brazil but has gained popularity abroad as a food and functional ingredient, yet little information exists on its health effect in humans. This study was performed as an acute four-way crossover clinical trial with acai pulp and clarified acai juice compared to applesauce and a non-antioxidant beverage as controls. Healthy volunteers (12) were dosed at 7 mL/kg of body weight after a washout phase and overnight fast, and plasma was repeatedly sampled over 12 h and urine over 24 h after consumption. Noncompartmental pharmacokinetic analysis of total anthocyanins quantified as cyanidin-3-O-glucoside showed Cmax values of 2321 and 1138 ng/L at t max times of 2.2 and 2.0 h, and AUC last values of 8568 and 3314 ng h L(-1) for pulp and juice, respectively. Nonlinear mixed effect modeling identified dose volume as a significant predictor of relative oral bioavailability in a negative nonlinear relationship for acai pulp and juice. Plasma antioxidant capacity was significantly increased by the acai pulp and applesauce. Individual increases in plasma antioxidant capacity of up to 2.3- and 3-fold for acai juice and pulp, respectively were observed. The antioxidant capacity in urine, generation of reactive oxygen species, and uric acid concentrations in plasma were not significantly altered by the treatments. Results demonstrate the absorption and antioxidant effects of anthocyanins in acai in plasma in an acute human consumption trial.
Article
Resveratrol has been associated with reduced cardiovascular disease and reduced cancer risk. This phytoalexin has been reported in a number of plant species, including grapes, and may be one of the compounds responsible for the health benefits of red wine. Analytical methods for measuring resveratrol in wine and peanuts were adapted to isolate, identify, and quantify resveratrol in several cultivars of peanuts. Aqueous ethanol (80% v/v) extracts from peanuts without seed coats were purified over alumina/silica gel columns and analyzed by reversed phase HPLC using a C-18 column. Peanuts from each market type, Virginia, runner, and Spanish, produced in four different locations contained from 0.03 to 0.14 microg of resveratrol/g. Seed coats from runner and Virginia types contained approximately 0.65 microg/g of seed coat, which is equivalent to <0.04 microg/seed. Quantitative analysis of 15 cultivars representing 3 peanut market types, which had been cold stored for up to 3 years, indicated a range of 0.02-1.79 microg/g of peanut compared to 0.6-8.0 microg/mL in red wines.
Article
Methanol extract (RM-ext) obtained from the dried rhizome of Rheum undulatum was screened for activity in experimental models of type I allergy. RM-ext exhibited the inhibition on 48-h homologous passive cutaneous anaphylaxis (PCA) in rats and an antigen-induced histamine release from rat peritoneal mast cells. Among nine stilbenes isolated from RM-ext, seven inhibited the histamine release. Rhapontigenin (compound 1), piceatannol (2) and piceatannol 3'-beta-D-glycoside (6) with oral administration showed the inhibition on PCA. Compounds 1 and 2 exhibited the inhibitory effect on sheep red blood cell-induced delayed-type hyper sensitivity (SRBC-DTH) of type IV allergic model. These results indicated that the rhizome of Rheum undulatum inhibits the allergic reactions and that these inhibitory effects may be partially attributable to the stilbenes mentioned above.
Article
Dietary antioxidants are thought to be beneficial in reducing the incidence of coronary heart disease. In this study, we compared resveratrol and analogues on their antioxidation and free radical scavenging activities to their protective effects on ischaemia-reperfusion induced injuries of rat hearts. Astringinin (3,3′,4′,5-tetrahydroxystilbene) was shown to be a more potent inhibitor than other analogues against Cu2+-induced LDL (low-density lipoprotein) oxidation, as measured by the formation of conjugated diene and TBARS (thiobarbituric acid-reactive substance) and by the electrophoretic mobility of the oxidized LDL. Resveratrol (trans-3,4′,5-trihydroxystilbene) and astringinin scavenged the stable free radical DPPH (1,1-diphenyl-2-picryl-hydrazyl) with an IC0.200 of 7.1 and 4.3 μM, respectively. Astringinin has a superoxide anion scavenging activity about 160 fold more potent than resveratrol. After a 30 min global ischemia followed by 2 h reperfusion, astringinin (10 μM) significantly reduced infarct size, superoxide anion production and increased functional recovery of the coronary flow in Langendorff-perfused rat hearts. The result showed there is a positive correlation between the anti-oxidation and cardioprotective activities among these phenolic compounds. Our finding together with the fact that astringinin is more water-soluble than resveratrol suggest that astringinin could potentially be used as an anti-oxidant and cardioprotective agent in biological systems. British Journal of Pharmacology (2002) 135, 1627–1633; doi:10.1038/sj.bjp.0704637
Article
Vitamin C content in fresh and freeze-dried herbal juice, such as guava (Psidium guajava Linn.) emblic myrobolan (Phyllanthus embica Linn.), lemon (Citrus aurantifollia Swing), sweet pepper (Capsicum annuum Linn.) Garcinia schomburgkiana Pierre and passion fruit (Passiflora laurifoia Linn.) was determined by direct titration with iodine. The method showed excellent linearity (r2>0.99) over the concentration ranges tested (100-500% of the amount found in the juice samples), good precision (R.S.D.<1.5%) and recovery (>97%). The limit of detection and limit of quantitation were 2.2 and 7.3 mg, respectively. The amount of vitamin C found were 80.1 mg/100 g for guava, 226.0 mg/100 g for emblic myrobolan, 52.8 mg/100 g for sweet pepper, 39.1 mg/100 g for passion fruit, 10.5 mg/100 g for lemon and 4.6 mg/100 g for G. schomburgkiana. The stability of vitamin C during the first 4 weeks was remarkably improved after freeze-dried process. The percent reductions of vitamin C after freeze-dried process were 41.4 and 20.4% for guava and emblic myrobolan, respectively. After 8 weeks, the freeze-dried samples contained only traces amount of vitamin C tested by thin layer chromatography.
Article
The methanol extract of the leaves of Passiflora incarnata (100 and 200 mg/kg, p.o.) exhibited significant antitussive activity on sulfur dioxide-induced cough in mice, the cough inhibition (39.4 and 65.0%, respectively) being comparable to that of codeine phosphate (10 and 20 mg/kg, p.o., respectively).
Article
Yellow passion fruit juice (PFJ, Passiflora edulis f. flavicarpa) is an important component of many tropical fruit beverages, but limited data exist on its antioxidant chemical composition and stability during processing and storage. PFJ fortified with ascorbic acid (450 mg/L) and sucrose (10%) was compared to a nonfortified control, and each was evaluated with and without vacuum deaeration to remove dissolved oxygen. Following pasteurization, juices were stored for 28 days at 37 degrees C to accentuate physicochemical changes. Pasteurization (85 degrees C for 30 min) resulted in minor changes to physicochemical attributes, but appreciable changes occurred during storage that resulted in termination of the study after 28 days. Oxygen control strategies proved to be ineffective for quality retention and indicated oxygen-independent reactions affecting juice color, phytochemical content, and antioxidant activity. Ascorbic acid and sucrose fortification had an overall preservation effect on total carotenoids, the former resulting in hyperchromic shifts in absorbance, indicating their chemoprotection. Pasteurization resulted in a 25% loss in l-ascorbic acid, which was completely destroyed after 14 days of storage; losses coincided with increased juice browning and formation of 5-hydroxymethylfurfural. Numerous polyphenolics were present in PFJ, and 16 of them were tentatively characterized on the basis of spectral similarities to known standards. Individually, polyphenolics increased during pasteurization, only to decline during storage at elevated temperatures. Antioxidant activity was measured in PFJ and in two subfractions (hydrophilic and lipophilic) after processing and storage, but antioxidant values were nonadditive. A significant chemical interaction affecting antioxidant capacity was found for hydrophilic juice components, but none was observed in the presence of lipophilic phytochemicals. Physicochemical attributes and overall quality of PFJ were retained following pasteurization but were significantly impacted by degradative reactions during accelerated storage.
Article
Gnetol (2,3',5',6-tetrahydroxy-trans-stilbene), a naturally occurring compound particularly found in the genus Gnetum, had a strong inhibitory effect on murine tyrosinase activity. Gnetol (IC50, 4.5 microM) was stronger than kojic acid (IC50, 139 microM) as a standard inhibitor for murine tyrosinase activity. Moreover, gnetol significantly suppressed, melanin biosynthesis in murine B16 melanoma cells.
Article
The aim of this study was to investigate the effects of dietary supplementation with (+)-catechin on cutaneous antioxidant enzymes and the skin damage caused by UVB irradiation. BALB/c mice were divided into three groups. Each group was fed a regular diet (RD) or a 2% catechin-supplemented diet for either 2 weeks (2CSD) or 4 weeks (4CSD) ad libitum prior to UVB irradiation. Skin was removed for the antioxidant enzyme assay, hematoxylin and eosin staining, and the TEM analysis before and at various time points after UVB (200 mJ/cm2) irradiation. Before UVB irradiation, the superoxide dismutase (SOD) and catalase (CAT) activities of the 2CSD and the 4CSD groups were found to be lower than those of the RD group, whereas the glutathione peroxidase (GPx) activity of the 4CSD group was higher than those of the RD and the 2CSD groups (P<0.05). The SOD and CAT activities of the RD group decreased after UVB irradiation, while those of the 2CSD and the 4CSD groups increased immediately after irradiation and then decreased (P<0.05). Immediately after UVB irradiation, the GPx activities of the 4CSD and the 2CSD groups increased, but that of the RD group decreased. The GPx activity of all three groups showed a tendency to return to pre-UVB irradiation levels with time. Light microscopic findings of the RD group showed epidermal thinning and apoptotic cells at 24 h after UVB irradiation and mostly necrotic cells at 48 h, whereas only moderate thickening of the epidermis was observed in the 2CSD group at 48 h after irradiation. An electron microscopic examination produced similar findings. At 48 h after irradiation, nearly all epidermal cells seemed to be damaged in the RD group as compared to the 2CSD group. These results demonstrate that dietary supplementation with (+)-catechin could protect epidermal cells against UVB-induced damage by modulating antioxidant enzyme activities.
Article
We have previously shown that royal jelly (RJ) promoted collagen production by skin fibroblasts in the presence of ascorbic acid-2-O-alpha-glucoside (AA-2G). In this study, we purified the honeybee RJ-derived collagen production-promoting factor (HBRJ-CPF) from an alkali-solubilized fraction of RJ by C18 reverse-phase column chromatography. The elution profile by the C18 column chromatography and the molecular mass of the purified HBRJ-CPF material coincided with those of 10-hydroxy-2-decenoic acid (10H2DA). We then examined the collagen production-promoting activities of several commercially available fatty acids contained in RJ. We found that 10H2DA and 10-hydroxydecanoic acid increased the collagen production in a dose-dependent manner. Furthermore, 10H2DA induced the fibroblast cell line, NHDF, to produce transforming growth factor-beta 1 (TGF-beta 1) which is an important factor for collagen production. As expected, the collagen production-promoting activity of 10H2DA was neutralized by the anti-TGF-beta 1 antibody. These result suggest that HBRJ-CPF identified as 10H2DA promoted the collagen production of AA-2G-treated fibroblasts by inducing TGF-beta 1 production.
Article
Chronic exposure of solar ultraviolet (UV) light to human skin results in photoaging. UV-induced oxidative damage and induction of matrix metalloproteinases (MMP) have been implicated in this process. Because polyphenols from green tea (GTP) prevent other cutaneous adverse effects of UV radiation we hypothesized that UV irradiation-induced oxidative damage and induction of MMP might be prevented in vivo in mouse skin by oral administration of GTP. GTP was administered in drinking water (0.2%, wt/vol) to SKH-1 hairless mice, which were then exposed to multiple doses of UVB (90 mJ per cm2, for 2 mo on alternate days) following in vivo photoaging animal protocol. Treatment of GTP resulted in inhibition of UVB-induced protein oxidation in vivo in mouse skin, a hallmark of photoaging, when analyzed biochemically, by immunoblotting, and immunohistochemistry. GTP treatment also inhibited UVB-induced protein oxidation in vitro in human skin fibroblast HS68 cells, which supports in vivo observations. Moreover, oral administration of GTP also resulted in inhibition of UVB-induced expression of matrix degrading MMP, such as MMP-2 (67%), MMP-3 (63%), MMP-7 (62%), and MMP-9 (60%) in hairless mouse skin. These data suggest that GTP as a dietary supplement could be useful to attenuate solar UVB light-induced premature skin aging.
Article
A study was conducted to determine the presence of resveratrol, pterostilbene, and piceatannol in Vaccinium berries. Samples representing selections and cultivars of 10 species from Mississippi, North Carolina, Oregon, and Canada were analyzed by gas chromatography/mass spectrometry. Resveratrol was found in Vaccinium angustifolium (lowbush blueberry), Vaccinium arboretum (sparkleberry), Vaccinium ashei (rabbiteye blueberry), Vaccinium corymbosum (highbush blueberry), Vaccinium elliottii (Elliott's blueberry), Vaccinium macrocarpon (cranberry), Vaccinium myrtillus (bilberry), Vaccinium stamineum (deerberry), Vaccinium vitis-ideae var. vitis-ideae (lingonberry), and Vaccinium vitis-ideae var. minor (partridgeberry) at levels between 7 and 5884 ng/g dry sample. Lingonberry was found to have the highest content, 5884 ng/g dry sample, comparable to that found in grapes, 6471 ng/g dry sample. Pterostilbene was found in two cultivars of V. ashei and in V. stamineum at levels of 99-520 ng/g dry sample. Piceatannol was found in V. corymbosum and V. stamineum at levels of 138-422 ng/g dry sample. These naturally occurring stilbenes, known to be strong antioxidants and to have cancer chemopreventive activities, will add to the purported health benefits derived from the consumption of these small fruits.
Article
In order to develop a new skin whitening agent, safflower (Carthamus tinctorius L.) seeds were evaluated for melanogenesis inhibitory activity and its active principles were identified following activity-guided isolation. The 80% aqueous methanol extract and ethyl acetate fraction from safflower seeds showed a significant inhibition for mushroom tyrosinase. Three active compounds, N-feruloylserotonin, N-(p-coumaroyl)serotonin, and acacetin, were isolated from the ethyl acetate fraction as the active principles. Compared with arbutin (IC50=0.223 mM), the IC50 values of these compounds were 0.023, 0.074, and 0.779 mM for N-feruloylserotonin, N-(p-coumaroyl)serotonin, and acacetin, respectively. It was also found that N-feruloylserotonin and N-(p-coumaroyl)serotonin strongly inhibited the melanin production of Streptomyces bikiniensis and B16 melanoma cells in comparison with a known melanogenesis inhibitor, arbutin.
Article
A new source to produce a significant quantity of a naturally occurring polyphenol, piceatannol, was investigated in this study. Both resveratrol and piceatannol are recognized as important ingredients in functional foods due to their beneficial health effects. However, unlike resveratrol, the piceatannol concentration in plants is very low. Thus, calluses of peanuts, an easily obtainable source, were chosen as the material to induce piceatannol production under controlled conditions. To induce resveratrol and piceatannol, calluses were exposed to the ultraviolet (UV) irradiation. Significant quantities of resveratrol and piceatannol were produced by calluses upon UV irradiation in both static and suspension culture conditions. The amounts of piceatannol and resveratrol produced in 1 g of calluses ranged from 2.17 to 5.31 microg and from 0.25 to 11.97 microg, respectively, in static culture. In suspension culture, the amounts of induced piceatannol and resveratrol were somewhat lower. The quantities of induced piceatannol and resveratrol reached a maximum at 18 h after UV irradiation treatment in static culture. In contrast, the levels of resveratrol and piceatannol remained almost constant throughout the experiments in suspension culture. The piceatannol produced by calluses in all studies was much higher than the values reported in the literature, whereas the resveratrol produced was comparable to reported values.
Article
The influence of the insoluble fiber-rich fraction (FRF) prepared from defatted Passiflora edulis seed, a potential fiber source, on plasma and hepatic lipids and fecal output were investigated in hamsters fed a hypercholesterolemic diet containing 5% insoluble FRF. The results showed that the consumption of insoluble FRF diet relative to cellulose diet could effectively (P < 0.05) decrease the levels of serum triglyceride, serum total cholesterol, and liver cholesterol, and increase (P < 0.05) the levels of total lipids, cholesterol, and bile acids in feces. The consumption of insoluble FRF also increased (P < 0.05) the fecal bulk and moisture. The marked cholesterol- and lipid-lowering effects of insoluble FRF might be partly attributed to its ability to enhance the excretion of lipids and bile acids via feces. Our results suggested that insoluble FRF could be a potential hypocholesterolemic ingredient for fiber-rich functional foods, but some further researches in humans may be needed to confirm its benefits.
Article
Unlabelled: The popular medicine Passiflora edulis has been used as a sedative, tranquilizer, against cutaneous inflammatory diseases and intermittent fever. Most of the pharmacological investigations of Passiflora edulis have been addressed to its Central Nervous System activities, such as anxiolytic, anticonvulsant and sedative actions. Otherwise, there are few reports about the anti-inflammatory activity of the Passiflora species. The aim of this study was to investigate the mechanism of the anti-inflammatory effect of aqueous lyophilized extract obtained from leaves of Passiflora edulis var. flavicarpa Degener (Passifloraceae) in the mouse model of pleurisy induced by carrageenan (Cg), bradykinin, histamine or substance P, observing the effects upon leucocytes migration, myeloperoxidase (MPO), nitric oxide (NO) concentrations and tumor necrosis factor-alpha (TNFalpha) and interleukin-1 beta (IL-1beta) levels. Results: Passiflora edulis (250mg/kg) administered by intraperitoneal route (i.p.) inhibited the leukocyte, neutrophils, myeloperoxidase, nitric oxide, TNFalpha and IL-1beta levels (P<0.01) in the pleurisy induced by carrageenan. Passiflora edulis (250-500mg/kg, i.p.) also inhibited total and differential leukocytes in the pleurisy induced by bradykinin, histamine or substance P (P<0.05). Conclusion: Several mechanisms, including the inhibition of pro-inflammatory cytokines (TNFalpha, IL-1beta), enzyme (myeloperoxidase) and mediators (bradykinin, histamine, substance P, nitric oxide) release and/or action, appear to account for Passiflora edulis's actions.
Article
Antioxidants such as vitamins C and E have been reported to inhibit the progression of ultraviolet (UV) radiation-induced pigmentation in the skin of hairless mice. However, little is known of the lightening effect of proanthocyanidin, a powerful polyphenolic antioxidant, on UV-induced pigmentation of the skin. We investigated the lightening effect of oral administration of a proanthocyanidin-rich grape seed extract (GSE) using guinea pigs with UV-induced pigmentation. These pigmented guinea pigs were fed diets containing 1% GSE or 1% vitamin C (w/w) for 8 weeks. GSE-feeding had an apparent lightening effect on the guinea pigs' pigmented skin. Histologic evaluation demonstrated a decrease in the number of 3,4-dihydroxyphenylalanine (DOPA)-positive melanocytes as well as 8-hydroxy-2'-deoxyguanosine (8-OHdG)-positive, Ki-67-positive, proliferating cell nuclear antigen (PCNA)-positive melanin-containing cells in the basal epidermal layer of the UV-irradiated skin in GSE-fed guinea pigs. In contrast, these parameters did not change in the skin of vitamin C-fed or control guinea pigs. GSE inhibited the activity of mushroom tyrosinase and also inhibited melanogenesis without inhibiting the growth of cultured B16 mouse melanoma cells. In conclusion, we demonstrated that oral administration of GSE is effective in lightening the UV-induced pigmentation of guinea pig skin. This effect may be related to the inhibition of melanin synthesis by tyrosinase in melanocytes and the reactive oxygen species (ROS)-related proliferation of melanocytes.
Article
Some plant flavonoids in the form of whole plant extracts have been used topically for skin inflammatory disorders. Since matrix metalloproteinase-1 (MMP-1, collagenase-1) plays an important role in unbalanced turn-over or rapid breakdown of collagen molecules in human inflamed/UV-irradiated skin, the effects of natural flavonoids on MMP-1 activity and MMP-1 expression were studied to establish the therapeutic potential. Against recombinant human MMP-1, flavonols such as quercetin and kaempferol were strong inhibitors with IC50 values of 39.6 and 43.7 microM, respectively, while flavones such as apigenin and wogonin showed only weak inhibitory activity. In addition, quercetin, kaempferol, apigenin and wogonin (12.5-25.0 microM) strongly inhibited MMP-1 induction in 12-O-tetradecanoylphorbol 13-acetate-treated human dermal fibroblasts, but naringenin (a flavanone) did not. By means of the electrophoretic mobility shift assay, these flavonoids were also found to inhibit activation of the transcription factor, activator protein-1 (AP-1). Moreover, quercetin inhibited extracellular signal-regulated protein kinase (ERK) and p38 mitogen-activated protein kinase (MAPK) activation, and kaempferol inhibited p38 MAPK and c-Jun N-terminal kinase (JNK) activation among the MAPKs tested. In contrast, flavones and naringenin did not inhibit the activation of these three MAPKs. These results have shown, for the first time, that naturally-occurring flavonoids (quercetin, kaempferol, apigenin and wogonin) inhibit MMP-1 and down-regulate MMP-1 expression via an inhibition of the AP-1 activation although the cellular inhibitory mechanisms differ depending on their chemical structures. Therefore, certain plant flavonoid