Article

Everlasting flower ( Helichrysum stoechas Moench) as a potential source of bioactive molecules with antiproliferative, antioxidant, antidiabetic and neuroprotective properties

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Abstract

Helichrysum stoechas (L.) Moench is one of the scientific names of everlasting flower, which has traditionally been used as an ornamental, medicinal and food plant. The aim of this study was to identify the main phytochemical constituents as well as to evaluate the potential of this plant in terms of antioxidant, antidiabetic and neuroprotective activities. The phytochemical analysis of the methanolic extract allowed for the identification of ten constituents mainly of phenolic nature and with chemosystematic relevance: two heterodimeric phloroglucinols, arzanol (1) and compound (3), one homodimeric α-pyrone, helipyrone (2), three phenolic acids, p-hydroxybenzoic (4), caffeic (5) and neochlorogenic (6) acids, one polymethoxylated and two glycosidic flavonoids, 5,7-dihydroxy-3,6,8-trimethoxyflavone (7), isoquercitrin (8) and quercetagetin-7-O-glucopyranoside (9) together with santinol B (10). Bioassays showed significant antioxidant and antiproliferative effects and for the first time the potential of Helichrysum stoechas to inhibit the MAO-A, AChE and TYR enzymes, as well as to exert anti-α-glucosidase and anti-dipeptidyl peptidase-4 activities.

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... Traditionally, an infusion of FL and AP of this plant has been used to treat disorders such as influenza and cold, fever, and nervousness, as well as a diuretic and to treat gallbladder, urinary bladder, digestive, and pancreatic problems. 50,127,128 Regarding the chemical composition, some compounds have been identified in this plant, including F, chalcones, phloroglucinol derivatives, EO, α-pyrones, and Te. 129 Several biological studies have described that H. stoechas possess antimicrobial, antiinflammatory, antioxidant, anti-α-glucosidase, anti-tyrosinase, anti-acetylcholinesterase, and anti-dipeptidyl peptidase-4 properties. ...
... 129 Several biological studies have described that H. stoechas possess antimicrobial, antiinflammatory, antioxidant, anti-α-glucosidase, anti-tyrosinase, anti-acetylcholinesterase, and anti-dipeptidyl peptidase-4 properties. 50,127 Among the reported bioactivities of H. stoechas, the antioxidant property is the most analyzed. For example, methanolic extracts of H. stoechas FL and leafy stems were evaluated by means of the total antioxidant capacity, DPPH and ABTS radical scavenging assays, FRAP and chelating power, and inhibition of β-carotene bleaching. ...
... 131 With regard to antitumor activity, a methanolic extract of this plant inhibits the proliferation of HeLa cells in vitro in a dose-dependent manner. 127 Finally, H. stoechas inhibited enzymes related to the central nervous system and neurotransmitter metabolism, such as acetylcholinesterase, monoamine oxidase, and tyrosinase, suggesting that H. stoechas exhibits a neuroprotective action. 50,127 ...
Article
Traditional plants have been used in the treatment of disease and pain due to the beneficial properties from the antioxidant, anti-inflammation, analgesic and antibiotic activities. Asteraceae family is one of the most common groups of plants used in folk medicine. The species Achillea millefolium, Arnica montana, Bellis perennis, Calendula officinalis, Chamaemelum nobile, Eupatorium cannabinum, Helichrysum stoechas and Taraxacum officinale have been used in different remedies in the North West region of Spain. Besides the health beneficial properties, some of them like Chamaemelum nobile and Helichrysum stoechas are already employed in cooking and culinary uses, like cocktails, desserts and savory dishes. This study aimed to review the current information of the nutritive and beneficial properties and bioactive compounds of these plants which are not mainly used as foods but are possible candidates for this purpose. The report highlights their current uses and their suitability for the development of new functional food industrial applications. Phenolic compounds, essential oils and sesquiterpene lactones are some of the most important compounds, being related to different bioactivities. Thus, they could be interesting for the development of new functional foods.
... Edible flowers have shown antitumor potential associated with their content in phenolic compounds and their actions on cycle regulation, apoptosis-related proteins, protein kinases, growth and transcription factors, and inflammation mediators, among others (Matić et al., 2013). A wide variety of edible flowers and extract types have been screened in different cancer cell lines (Jdir et al., 2016;Kashif et al., 2015;Lee, Lee, & Choung, 2011;Les et al., 2017;Matić et al., 2013;Miceli et al., 2020;Ombra, D'Acierno, Nazzaro, & Fratianni, 2019;Sagdic et al., 2013;Telkoparan Akillilar, Tuglu, & Shomali Moghaddam, 2018). Cytotoxicity was found to be directly related to the phenolic content (Kucekova, Mlcek, Humpolicek, & Rop, 2013). ...
... Currently, the most established approach to treat AD is the inhibition of the cholinesterase enzyme, preventing the breakdown of ACh (National Institute on Aging, 2018). Methanolic extracts of some edible flowers, such as Nymphaea pubescens (Acharya, Dutta, Chaudhury, & De, 2018), Helichrysum stoechas (Les et al., 2017), C. cyanus or Anthyllis vulneraria (Nowicka & Wojdyło, 2019) and ethanolic extracts of Tagetes erecta (Moliner et al., 2018) and V. wittrockiana (Moliner et al., 2019) flowers exhibited an inhibition of the enzyme acetylcholinesterase (AChE) in vitro (Acharya et al., 2018;Les et al., 2017;Moliner et al, 2018Moliner et al, , 2019Nowicka & Wojdyło, 2019). That inhibitory effect was also found against butyrylcholinesterase (BuChE) for some flower extracts, but this effect was stronger against AChE than against BuChE (Nowicka & Wojdyło, 2019). ...
... Currently, the most established approach to treat AD is the inhibition of the cholinesterase enzyme, preventing the breakdown of ACh (National Institute on Aging, 2018). Methanolic extracts of some edible flowers, such as Nymphaea pubescens (Acharya, Dutta, Chaudhury, & De, 2018), Helichrysum stoechas (Les et al., 2017), C. cyanus or Anthyllis vulneraria (Nowicka & Wojdyło, 2019) and ethanolic extracts of Tagetes erecta (Moliner et al., 2018) and V. wittrockiana (Moliner et al., 2019) flowers exhibited an inhibition of the enzyme acetylcholinesterase (AChE) in vitro (Acharya et al., 2018;Les et al., 2017;Moliner et al, 2018Moliner et al, , 2019Nowicka & Wojdyło, 2019). That inhibitory effect was also found against butyrylcholinesterase (BuChE) for some flower extracts, but this effect was stronger against AChE than against BuChE (Nowicka & Wojdyło, 2019). ...
Article
Background The consumption of edible flowers has increased in recent years because of their wide use in gastronomy as a decorative element or as an ingredient in dishes. In addition to influencing texture, taste or appearance, flowers are rich in bioactive compounds. Scope and approach This review focuses on the composition and nutritional features of edible flowers and their extracts, and their health benefits related to cardiovascular diseases, cancer, neurological diseases, diabetes, obesity, in addition to their hepatoprotective and microbicidal effects. The mechanisms though which some of them exert their effects and the specific compounds associated with these effects have also been addressed. Key findings and conclusions Edible flowers have a high content in phenolic compounds and a high antioxidant capacity, property that confers positive effects on oxidative stress-related diseases. Some extracts based on edible flowers exert hepato-, neuro- or cardioprotective actions. Anticancer properties, improvements in metabolic disorders and microbiocidal effects even in multidrug-resistant bacteria have also been attributed to some edible flowers or their extracts. Most of the studies have been performed in vitro, so further assays in in vivo models are needed. Additionally, it would be important to elucidate the mechanisms by which these observed effects are performed. In conclusion, edible flowers could be used as a new approach for the development of nutraceutical products or functional foods.
... In the Spanish folk medicine, H. stoechas is used for mitigation of inflammatory complications, for wound healing , to soothe toothache, manage urologic and digestive disorders [2]. Other traditional medicinal uses of H. stoechas includes the treatment of influenza, nervousness, and pancreatic problems [6]. ...
... Scientific studies have focused on the biological potential H. stoechas and reported its anti-α-glucosidase, anti-tyrosinase, anti-acetylcholinesterase, anti-dipeptidyl peptidase-4, and antioxidant activities [6]. Hydroalcoholic extract of H. stoechas has been identified as promising candidates for the cosmetic industry. ...
... Arzanol, α-pyrone, helipyrone, p-hydroxybenzoic, caffeic acid, neochlorogenic acid, 5,7-dihydroxy-3,6,8-trimethoxyflavone, isoquercitrinand, quercetagetin-7-O-glucopyranoside, and santinol B have been isolated from the J o u r n a l P r e -p r o o f methanolic extracts of H. stoechas. [6]. The capitula of H. stoechas extracted with 70% ethanol () showed significant amounts of phenolic acids (chlorogenic and quinic acid and their derivatives) as well as other polyphenols such as quercetin, kaempferol, apigenin glucosides, and tetrahydroxychalcone-glucoside [8]. ...
Article
We endeavoured to probe into and compare the possible effect(s) of different extraction techniques (accelerated solvent extraction (ASE), microwave-assisted extraction (MAE), ultrasonication-assisted extraction (UAE), maceration, and Soxhlet extraction (SE)) on the bioactivity (antioxidant and enzyme inhibitory activities) of the aerial parts of Helichrysum stoechas subsp. barrelieri (Ten.) Nyman. Total phenolic and flavonoid contents of the extracts obtained by different extraction methods followed the order of ASE > MAE > UAE > maceration > SE. Extract obtained by ASE was the most potent radical scavenger (219.92 and 313.12 mg Trolox equivalent [TE]/g, against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS), respectively) and reducing agent (927.39 and 662.87 mg TE/g, for cupric reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP), respectively). Helichrysum stoechas extract obtained by UAE (18.67 mg ethylenediaminetetraacetic equivalent [EDTAE]/g) was the most active metal chelator and inhibitor of acetylcholinesterase (4.23 mg galantamine equivalent [GALAE]/g) and butyrylcholinesterase (6.05 mg GALAE/g) cholinesterase. Extract from maceration (183.32 mg kojic acid equivalent [KAE]/g) was most active against tyrosinase while ASE extract (1.66 mmol acarbose equivalent [ACAE]/g) effectively inhibited α-glucosidase. In conclusion, data amassed herein tend to advocate for the use of non-conventional extraction techniques, namely ASE and UAE, for the extraction of bioactive secondary metabolites from H. stoechas aerial parts.
... The plant is well adapted to environments that lack water as it naturally grows on alkaline, dry, sandy and poor soil at the altitude from the sea level up to 2200 m [6]. The Helichrysum Miller genus includes more than a thousand of taxa, among them the most well-known and studied species are Helichrysum italicum (Roth) G. Don [7] (Figure 1), Helichrysum stoechas (L.) Moench [8], and Helichrysum arenarium (L.) Moench [9]. H. italicum and H. stoechas are distributed throughout the Mediterranean [10] but are especially characteristic to Adriatic Plants 2021, 10, 1738 2 of 17 region [11] and Iberian Peninsula [12], respectively, whereas H. arenarium is mostly found in the Central Europe [9,10]. ...
... H. italicum and H. stoechas are distributed throughout the Mediterranean [10] but are especially characteristic to Adriatic Plants 2021, 10, 1738 2 of 17 region [11] and Iberian Peninsula [12], respectively, whereas H. arenarium is mostly found in the Central Europe [9,10]. Despite the long tradition in treatment of various disorders for all three before-mentioned species, their traditional use for treating digestive problems (e.g., fullness and bloating) has been approved by the WHO and the European Medicines Agency (EMA) for the species H. arenarium alone [8]. Nevertheless, H. italicum has been recently investigated quite extensively, especially in the Balkan countries. ...
... Iberian Peninsula [12], respectively, whereas H. arenarium is mostly found in the Central Europe [9,10]. Despite the long tradition in treatment of various disorders for all three before-mentioned species, their traditional use for treating digestive problems (e.g., fullness and bloating) has been approved by the WHO and the European Medicines Agency (EMA) for the species H. arenarium alone [8]. Nevertheless, H. italicum has been recently investigated quite extensively, especially in the Balkan countries. ...
Article
Full-text available
Helichrysum italicum is a Mediterranean plant with various pharmacological activities. Despite extensive reports on the bioactivity of the plant, its clinically studied applications have not yet been reviewed. The aim of our study was to gather information on the internal use of H. italicum and its bioactive constituents to determine its efficacy and safety for human use. We reviewed research articles that have not been previously presented in this context and analyzed relevant clinical studies with H. italicum. Cochranelibrary.com revealed six eligible clinical trials with H. italicum that examined indications for pain management, cough, and mental exhaustion. Although the efficacy of H. italicum has been demonstrated both in in vitro tests and in humans, it is difficult to attribute results from clinical trials to H. italicum alone, as it has usually not been tested as the sole component. On the other hand, clinical trials provide positive information on the safety profile since no adverse effects have been reported. We conclude that H. italicum is safe to use internally, while new clinical studies with H. italicum as a single component are needed to prove its efficacy. Based on the recent trend in H. italicum research, further studies are to be expected.
... A recent study showed the inhibitory activity of Helichrysum stoechas (L.) Moench methanolic extract on monoamine oxidase A (MAO-A), which is a well-known enzyme with an important role in maintaining the normal function of several modulators of the central nervous system (CNS) that are involved in behavior, pain and cognitive functions [17]. MAO-A inhibitors have been generally used for the treatment of mood disorders, in particular as antidepressant agents [18] and several studies have reported that the effect of MAO-A inhibitors in increasing ERK activation may be an important reason for their pharmacological activity. ...
... Indeed, only its antioxidant and antimicrobial properties have been studied [25]. Recently, Les et al. [17] reported the in vitro dose-dependent inhibition of MAO-A enzyme activity, which is an important target in the management of mood disorders [18], using a chemically characterized Helichrysum stoechas methanolic extract (HSE). For this reason, the aim of this work was to investigate the potential effect of the above-mentioned extract in the management of anxiety-and depression-related symptoms in animal models. ...
... Helichrysum stoechas (L.) Moench methanolic extract (HSE) was obtained from the aerial parts, including flowers, by cold maceration with methanol as previously reported [17,43]. The solvent was removed by using rota-vaporing techniques. ...
Article
Full-text available
The long-term use of anxiolytic and antidepressant drugs can cause a plethora of side effects and the use of complementary and alternative medicine, which is generally considered safer than conventional medicine, is consistently increasing. Helichrysum stoechas (L.) Moench methanolic extract (HSE) has shown MAO-A inhibitory properties in previous studies. With the aim of obtaining innovative and safer therapies for mood disorders, this study investigated the potential activity of HSE in the management of anxiety- and depression-related symptoms. HSE showed dose-dependent (30–100 mg/kg p.o.) anxiolytic-like activity in the light dark box and marble burying tests, without any antidepressant-like activity, as shown by the results of the tail suspension test. Additionally, HSE did not have any effect on the modulation of pain, which highlights its selectivity in the control of anxiety-related behavior. At active doses, HSE did not produce any sedative effect or result in impaired motor coordination and memory functions. Western blotting experiments showed the ability of HSE to counteract the reduction in the phosphorylation of ERK44/42, to restore brain-derived neurotrophic factor (BDNF) expression and to return cyclic AMP response element binding (CREB) levels to basal levels in noradrenergic hippocampal neurons of mice exposed to an anxiety-related environment, which indicates a protective role against anxiety behavior. These results suggest that oral administration of HSE might represent an interesting opportunity for the management of anxiety disorders.
... For example, the discovery of artemisinin, an antimalarial drug from the leaves of Artemisia annua L., a member of the Asteraceae family [1][2][3][4][5][6][7][8] illustrated the importance of the family toward a role in the production of plant-derived medicines. The Asteraceae is one the largest families of flowering plants in the world, with about 1600 genera and 23,000 species, found almost everywhere in the world except in Antarctica [9][10][11][12][13][14]. Several members of this family are characterized by phytochemical compounds such as acetophenones, caffeoylquinic acids, phloroglucinol, polyphenols, pyrrolizidine alkaloids, polyacetylenes, chalcone, flavonoids, and diterpenoids [15][16][17][18][19]. Several species of the family Asteraceae are characterized by analgesic, anti-allergic, antibacterial, antidiabetic, antifungal, antiviral, antiinflammatory, antimigraine, antioxidant, antiproliferative, antipyretic, antitumor, antiulcer, cardiotonic, and neuroprotective and neurotoxicity activities [16,17,[19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. The genus Helichrysum Mill. is one of the most important sources of herbal medicines among the Asteraceae genera [17,27,[29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]. ...
... The Asteraceae is one the largest families of flowering plants in the world, with about 1600 genera and 23,000 species, found almost everywhere in the world except in Antarctica [9][10][11][12][13][14]. Several members of this family are characterized by phytochemical compounds such as acetophenones, caffeoylquinic acids, phloroglucinol, polyphenols, pyrrolizidine alkaloids, polyacetylenes, chalcone, flavonoids, and diterpenoids [15][16][17][18][19]. Several species of the family Asteraceae are characterized by analgesic, anti-allergic, antibacterial, antidiabetic, antifungal, antiviral, antiinflammatory, antimigraine, antioxidant, antiproliferative, antipyretic, antitumor, antiulcer, cardiotonic, and neuroprotective and neurotoxicity activities [16,17,[19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. The genus Helichrysum Mill. is one of the most important sources of herbal medicines among the Asteraceae genera [17,27,[29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]. Helichrysum longifolium DC. and Helichrysum pedunculatum Hilliard and B.L. Burtt. ...
Article
Full-text available
Helichrysum longifolium and Helichrysum pedunculatum have a long history of medicinal use, particularly managing wounds acquired during male circumcision rites in South Africa. There is a need to evaluate the existence of any correlation between the ethnomedicinal applications, the phytochemistry and pharmacological properties of the species. Therefore, in this review, analyses of the botanical, medicinal, and chemical and biological activities of H. longifolium and H. pedunculatum are presented as well as exploring the potential of the two species as important sources of health and pharmaceutical products. Information on the botany, medicinal uses, and phytochemistry and biological activities of H. longifolium and H. pedunculatum was assembled from several internet sources which included Scopus, Google Scholar, Elsevier, Science Direct, Web of Science, PubMed, SciFinder, and BMC. Additional information was sourced from journal articles, scientific reports, theses, books, and book chapters obtained from the University library. This study showed that alkaloids, flavonoids, linoleic acid, oleic acid, phenol, proanthocyanidin, saponins, and tannins have been identified from the leaves of H. longifolium and H. pedunculatum. The pharmacological research showed that H. longifolium and H. pedunculatum extracts and compounds isolated from the species have antibacterial, antifungal, anti-inflammatory, antioxidant, antiplasmodial, antiprotozoal, and cytotoxicity activities. For local communities to use H. longifolium and H. pedunculatum extracts with confidence as herbal medicines, there is a need for extensive phytochemical and pharmacological studies. Further research is required to establish the safety profiles of different H. longifolium and H. pedunculatum preparations.
... Ethnobotanical surveys revealed that H. stoechas have been used to treat flu, common cold, wound healing, digestive disorders and many other medical issues (Barroso et al., 2014;Zengin et al., 2020). Also, this plant showed many biological properties such as anti-inflammatory and antioxidant, as well as certain medicinal activities, including antidiabetic, antimicrobial, antiproliferative and antiallergic (Carini et al., 2001;Les et al., 2017;Zengin et al., 2020). The phytochemical studies of H. stoechas revealed a variety of secondary metabolites, including phenolic, flavonoids and terpenoids (Al-Rehaily et al., 2008). ...
... Indeed, it has been reported that quercetin and luteolin, two flavonoids present in the studied extracts, exhibited higher superoxide scavenging activity (Fazilatun et al., 2004). Moreover, Les et al. (2017) reported the potential superoxide scavenging effect of the Helichrysum stoechas methanolic extract. ...
Article
The present study was aimed to investigate the phenolic composition, antioxidant and anti-inflammatory activities of ethyl acetate (EAE) and n-butanol (BuE) extracts obtained from the aerial parts of Helichrysum stoechas (L.) Moench. Both extracts are rich in polyphenols and flavonoids with a wealth more marked for EAE. The LC-ESI-MS analysis revealed the presence of many important phenolics such as isoquercitrin, rutin, ferulic acid and chlorogenic acid. The extracts exhibited anti-inflammatory effect by inhibiting the croton oil-induced ear œdema and the neutrophil migration in carrageenan-induced air pouch model. These extracts stabilized erythrocytes membrane and inhibited protein denaturation. In addition, both extracts exerted antioxidant effect by scavenging superoxide anion radicals, hydroxyl radicals and hydrogen peroxide. Moreover, they exerted a significant protective effect against AAPH-induced erythrocyte hemolysis. Results obtained in the present study indicate that H. stoechas can be a potential source of natural antioxidant and anti-inflammatory agents.
... H. arenarium has long been used in traditional medicine as an herbal tea for the treatment of various health-related problems such as fever and nervousness, as well as gall-bladder and urinary-tract diseases. Recently, the World Health Organization (WHO) and European Medicines Agency (EMA) have officially approved the use of H. arenarium infusions and tinctures for the treatment of digestive disorders (Akaberi et al., 2019;Les et al., 2017). Many scientific studies show that H. arenarium is a rich source of essential oils, volatile acids and fatty acids as well as various phenolic compounds, including phenolic acids, flavonoids, coumarins and ligno-flavonoids (Akaberi et al., 2019;Albayrak et al., 2010;Les et al., 2017;Liu et al., 2019;Pljevljakušić et al., 2018). ...
... Recently, the World Health Organization (WHO) and European Medicines Agency (EMA) have officially approved the use of H. arenarium infusions and tinctures for the treatment of digestive disorders (Akaberi et al., 2019;Les et al., 2017). Many scientific studies show that H. arenarium is a rich source of essential oils, volatile acids and fatty acids as well as various phenolic compounds, including phenolic acids, flavonoids, coumarins and ligno-flavonoids (Akaberi et al., 2019;Albayrak et al., 2010;Les et al., 2017;Liu et al., 2019;Pljevljakušić et al., 2018). To date, nearly 40 different flavonoids have been identified in the H. arenarium inflorescence, out of which the chalcone isosalipurposide and the isomers of flavanone naringenin are the dominant ones (Akaberi et al., 2019;Babotȃ et al., 2018;Jarzycka et al., 2013;Pljevljakušić et al., 2018). ...
Article
In the present study, an analytical methodology based on natural deep eutectic solvents (NADESs) and ultrasound-assisted extraction (UAE) is demonstrated as an environmentally friendly protocol for the isolation of valuable phenolic compounds from inflorescences of Helichrysum arenarium L. For this purpose, 11 different NADESs containing choline chloride and selected hydrogen bond donors, including organic acids, polyols, sugars and an amide, were tailored and evaluated based on the content of individual compounds determined by HPLC-PDA-MS n. Choline chloride-lactic acid based NADES (NADES 1) showed the most promising extraction effi-ciencies for flavonoids (15.34 ± 0.10 mg g − 1) and phenolic acids (5.10 ± 0.12 mg g − 1) as the efficiencies were comparable to those obtained with 80 % methanol (15.60 ± 0.09 mg g − 1 and 5.32 ± 0.18 mg g − 1 , respectively) and up to 54 % higher compared to water (9.94 ± 0.13 mg g − 1 and 5.47 ± 0.22 mg g − 1). Furthermore, three essential parameters of the proposed NADES 1 methodology (UAE time, water content in NADES, and NADES hydrogen donor/acceptor molar ratio) were optimized by Box-Behnken experimental design. Based on the statistically evaluated results the following conditions were determined to be optimal: an UAE time of 85 min, 38 % water in NADES 1, and a molar ratio of choline chloride:lactic acid of 1:4. The developed approach allows easy transfer of the proposed methodology to large-scale extraction, enabling clean production with minimal environmental impact.
... tyrrhenicum Bacch., Brullo e Giusso (Asteraceae) in a littoral location of La Maddalena Archipelago was investigated and its oil containing monoterpene ester neryl acetate, the oxygenated sesquiterpene 5-eudesmen-11-ol, the sequiterpene hydrocarbons δ-cadinene and γ-cadinene showed a strong inhibitory activity on human malignant melanoma cells A375 (IC 50 of 16 μg/mL) (Ornano et al., 2015). Les et al. performed phytochemical analysis on the methanolic extracts of Helichrysum stoechas Moench collected from Villanueva de Gállego (Zaragoza, Spain) and identified 10 constituents as 2 heterodimeric phloroglucinols including arzanol, 1 homodimeric αpyrone (helipyrone), 3 phenolic acids (p-hydroxybenzoic, caffeic and neo-chlorogenic acids), 1 polymethoxylated and 2 glycosidic flavonoids (5,7-dihydroxy-3,6,8-trimethoxyflavon, isoquercitrin and quercetagetin-7-O-glucopyranoside) together with santinol B. Bioassays of these metabolites showed significant antioxidant, antiproliferative, anti-α-glucosidase, anti-dipeptidyl peptidase-4 activities as well as inhibiton of MAO-A, AChE, and TYR enzymes (Les et al., 2017). ...
... In another study, Helichrysum extracts were found to have significant antimicrobial activity against 13 bacteria and 2 yeasts with agar diffusion method (Albayrak et al., 2010). In a more recent study, Helichrysum stoechas Moench showed significant antioxidant and antiproliferative activities (Les et al., 2017). In a 2016 study, 3 new amino-phloroglucinol derivatives named helichrytalicines were isolated and identified along with 17 known compounds from medium-polar extract of H. italicum and one compound was found to have high capacity to inhibit biofilm formation of Staphylococcus epidermidis (D'Abrosca et al., 2016). ...
Article
Full-text available
It is known that some addition products of beta-nitrostyrenes exhibit potent antimicrobial activity. In order to investigate the effects of structural modifications on the biological properties, some new Michael type addition products of beta-ethyl-beta-nitrostyrenes were synthesized. In this study, eight new 1-[(2-aminophenyl)thio]-1-phenyl-2-nitrobutane (2) derivatives were synthesized by addition of 2-aminothiophenol to the double bond of beta-ethyl-beta-nitrostyrenes (1). The chemical structures were proved by IR and 1H-NMR data and by elemental analysis. Antimicrobial activities of the synthesized compound were investigated against Escherichia coil, Pseudomonas aeruginosa, Proteus mirabilis, Enterococcus faecalis, Bacillus subtilis, Staphylococcus aureus, Candida albicans by the microdilution method. In addition, the newly synthesized compounds were studied for antiviral activities. All of them were found to be almost 100 fold more active than the standard compound aciclovir (CAS 59277-89-3).
... tyrrhenicum Bacch., Brullo e Giusso (Asteraceae) in a littoral location of La Maddalena Archipelago was investigated and its oil containing monoterpene ester neryl acetate, the oxygenated sesquiterpene 5-eudesmen-11-ol, the sequiterpene hydrocarbons δ-cadinene and γ-cadinene showed a strong inhibitory activity on human malignant melanoma cells A375 (IC 50 of 16 μg/mL) (Ornano et al., 2015). Les et al. performed phytochemical analysis on the methanolic extracts of Helichrysum stoechas Moench collected from Villanueva de Gállego (Zaragoza, Spain) and identified 10 constituents as 2 heterodimeric phloroglucinols including arzanol, 1 homodimeric αpyrone (helipyrone), 3 phenolic acids (p-hydroxybenzoic, caffeic and neo-chlorogenic acids), 1 polymethoxylated and 2 glycosidic flavonoids (5,7-dihydroxy-3,6,8-trimethoxyflavon, isoquercitrin and quercetagetin-7-O-glucopyranoside) together with santinol B. Bioassays of these metabolites showed significant antioxidant, antiproliferative, anti-α-glucosidase, anti-dipeptidyl peptidase-4 activities as well as inhibiton of MAO-A, AChE, and TYR enzymes (Les et al., 2017). ...
... In another study, Helichrysum extracts were found to have significant antimicrobial activity against 13 bacteria and 2 yeasts with agar diffusion method (Albayrak et al., 2010). In a more recent study, Helichrysum stoechas Moench showed significant antioxidant and antiproliferative activities (Les et al., 2017). In a 2016 study, 3 new amino-phloroglucinol derivatives named helichrytalicines were isolated and identified along with 17 known compounds from medium-polar extract of H. italicum and one compound was found to have high capacity to inhibit biofilm formation of Staphylococcus epidermidis (D'Abrosca et al., 2016). ...
Article
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Helichrysum species are used widely to treat various medical conditions. In the present study, 14 extracts obtained from 7 Helichrysum species such as H. araxinum Takht. ex Kirp., H. armenium DC, H. arenarium, H. pallasii, H. stoechas, H. sanguineum, and H. graveolens (Asteraceae) were screened for their in vitro antibacterial, antifungal, and antiviral activities. Antibacterial and antifungal activities were evaluated against both standard and isolated strains of Gram negative (E. coli, P. aeruginosa, P. mirabilis, K. pneumoniae, A. baumanni) and Gram positive (S. aureus, E. faecalis) bacteria, as well as fungi (Candida albicans, C. parapsilosis) by microdilution method. We performed susceptibility testing according to the Clinical and Laboratory Standards Institute (CLSI; formerly NCCLS). As human pathogens both Herpes simplex virus Type-1 (HSV-1), a DNA virus, and Parainfluenza-3 virus (PI-3), an RNA virus, were employed for antiviral assessment of the water and ethanol extracts of Helichrysum species by using Madin-Darby Bovine Kidney and Vero cell line. All the extracts showed more potent antibacterial activity against Gram positive bacteria (ranging between 16 and 64 μg/mL) than Gram negative (8–64 μg/mL), while showing considerable antifungal activity at 8 μg/mL concentration. Antifungal activities of the extracts were found to be close to antifungal agents in routine clinical use. In particular, all of the ethanolic extracts were found to show better inhibition against S. aureus with a MIC value of 8 μg/mL. In the meantime, ethanolic extracts of H. arenarium and H. armenium DC showed notable antiviral activity against both HSV-1 and PI-3; at a range of 2–32 and 4–64 μg/mL, respectively, by the absence of cytophatic effect. All activities were evaluated at nontoxic concentrations. Helichrysum arenarium and H. armenium DC were found to be the most remarkable species among the tested extracts in terms of bioactivity.
... tyrrhenicum Bacch., Brullo e Giusso (Asteraceae) in a littoral location of La Maddalena Archipelago was investigated and its oil containing monoterpene ester neryl acetate, the oxygenated sesquiterpene 5-eudesmen-11-ol, the sequiterpene hydrocarbons δ-cadinene and γ-cadinene showed a strong inhibitory activity on human malignant melanoma cells A375 (IC 50 of 16 μg/mL) (Ornano et al., 2015). Les et al. performed phytochemical analysis on the methanolic extracts of Helichrysum stoechas Moench collected from Villanueva de Gállego (Zaragoza, Spain) and identified 10 constituents as 2 heterodimeric phloroglucinols including arzanol, 1 homodimeric αpyrone (helipyrone), 3 phenolic acids (p-hydroxybenzoic, caffeic and neo-chlorogenic acids), 1 polymethoxylated and 2 glycosidic flavonoids (5,7-dihydroxy-3,6,8-trimethoxyflavon, isoquercitrin and quercetagetin-7-O-glucopyranoside) together with santinol B. Bioassays of these metabolites showed significant antioxidant, antiproliferative, anti-α-glucosidase, anti-dipeptidyl peptidase-4 activities as well as inhibiton of MAO-A, AChE, and TYR enzymes (Les et al., 2017). ...
... In another study, Helichrysum extracts were found to have significant antimicrobial activity against 13 bacteria and 2 yeasts with agar diffusion method (Albayrak et al., 2010). In a more recent study, Helichrysum stoechas Moench showed significant antioxidant and antiproliferative activities (Les et al., 2017). In a 2016 study, 3 new amino-phloroglucinol derivatives named helichrytalicines were isolated and identified along with 17 known compounds from medium-polar extract of H. italicum and one compound was found to have high capacity to inhibit biofilm formation of Staphylococcus epidermidis (D'Abrosca et al., 2016). ...
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Glycolysis is a metabolic pathway vital to the production of energy and some organisms rely on it solely to meet their energy requirements. It is also a central pathway in the metabolism of carbohydrates and a source of therapeutic targets against diabetes and cancer. Caffeoylquinic acids (CQAs) have been extensively studied for their role in the treatment and prevention of diabetes (and cancer) but their mechanisms of action remain mostly unknown. As such, molecular docking was used to find possible targets of CQAs in the glycolysis pathway. The molecular docking assays showed that CQAs were docked preferably to the Rossman fold (nicotinamide adenine dinucleotide — NAD(H) binding site) of oxidoreductases, that use NAD(H) as a cofactor, than to any other site. In-vitro assays were then performed using two NAD(H) dependent oxidoreductases from glycolysis (alcohol dehydrogenase and L-lactate dehydrogenase) in order confirm if CQAs would compete with the cofactor to inhibit the reaction. The results from these assays indicate that CQAs can act as both inhibitors and activators of NAD(H) dependent oxidoreductases of the glycolysis pathway.
... This species has been used in European folk medicine as a choleretic, hepatoprotective, and detoxication agents (Czinner et al., 2000). Based on traditional knowledge, a preparation from flowers of Helichrysum stoechas (L.) Moench in the form of infusion or decoction has been approved by the World Health Organization (WHO) and the European Medicines Agency (EMA) for the treatment of digestive problems including fullness and bloating (Neves et al., 2009;Les and Venditti, 2017). Table 1 shows the application of different Helichrysum spp. in various traditional and folk systems of medicine. ...
... Research concerning pharmacological activities of everlasting flowers indicate that these plants have strong anti-inflammatory, antimicrobial (Les and Venditti, 2017), antioxidant (Babotȃ et al., 2018), anti-atherosclerotic (Mao et al., 2017), anti-HIV (Heyman et al., 2015), and anti-tuberculosis (Skvortsova et al., 2015;Chinsembu, 2016) activities. Moreover, phytochemical studies show that phenolic compounds including different types of free and glycosylated flavonoids and phenolic acids are the main classes of secondary metabolites in this genus (Gouveia and Castilho, 2011;Mari et al., 2014;Pereira et al., 2017). ...
Article
Tropical diseases such as leishmaniosis constitute a major health concern in developing countries. Multiresistance of pathogens against classical antibiotics is a growing problem in treating infectious diseases. Thus, the search for new antibiotics is an urgent challenge. Helichrysum spp., mainly distributed in African countries, have been used in traditional and folk medicine for the treatment of several disorders including infectious diseases such as protozoal problems. In an ongoing project on the beneficial effects of Helichrysum spp., we aim to investigate and compare the anti-protozoal activities and phytochemical components of Helichrysum oligocephalum DC. and Helichrysum leucocephalum Ausfeld. Previously, we discovered pyrone and phloroglucinol derivatives as the active anti-protozoal components in Helichrysum oocephalum Boiss. [IC50 values 5.08 µg/mL and 4.01 µg/mL against Leishmania donovani and Plasmodium falciparum, respectively for dichloromethane (DCM) fraction]. As the former plants also showed similar activities to some extent [IC50 values 5.19 µg/mL and 5.42 µg/mL against L. donovani and P. falciparum respectively for DCM fraction of H. oligocephalum, IC50 value 3.8 µg/mL against P. falciparum for DCM fraction of H. leucocephalum], we decided to compare the metabolite profiles of those plants with H. oocephalum for dereplication purposes. A sensitive method coupling high-performance liquid chromatography with a photodiode-array detector (PDA) and electrospray ionization mass spectrometry (ESIMS) was optimized for separation and metabolite profiling. The LC-ESIMS metabolite profiles of the fractions from the plants were compared by applying a two-step workflow using an ACD/MS workbook suite add-in, and data clustering on an open-source web platform freeclust. The metabolites were identified by NMR and LC-PDA-ESIMS techniques. The metabolites can be categorized into major types namely flavonoids, phenolic acids, pyrone, and phloroglucinol derivatives. Phloroglucinol derivatives were mainly present in DCM fractions. DCM extract of H. oligocephalum showed the most similar profile to our previously studied extract of H. oocephalum and seems to be even much richer in pyrone and phloroglucinol derivatives. The data could emphasize the potential of Helichrysum spp. for the treatment of infectious diseases. However, more studies on the other species around the world are needed to have a much better insight.
... In contrast to Helichrysum italicum, which has been extensively studied [1], only a few studies were conducted on H. stoechas [2]. They showed interesting biological activities of methanolic extracts from flowering aerial parts towards cosmetic [3] and pharmaceutical [4] applications, as well as in the food industry because of its antimicrobial potential and strong antioxidant capacity [5][6][7]. Recent data showed that powder or extract of H. stoechas had antifungal activity against plant pathogenic fungus Sclerotinia sclerotiurum, opening new perspectives in the field of agro ecology [8]. ...
... However, a stimulating effect of elicitation on phytotoxic activity on cress root growth was observable for extract concentrations in the range from 0.31 to 0.83 mg.mL -1 ( Table 2, values in bold), with an inhibition rate being for each extract concentration 8% greater with MeJa-elicited than with non-elicited cells extracts. 4: Root (R) and hypocotyl (H) lengths for each batch were standardized by subtracting their batch average and dividing the difference by their batch standard deviation. The "batch" effect was therefore corrected, which allowed a fair comparison between the three batches. ...
... Inhibitory potential of the extracts on some key enzymes involved in neurological, metabolic and skin-related diseases was tested using in vitro assays adapted to a microplate reader. Hence, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory properties (related to neuroprotective potential of the extracts) were investigated using protocols described by Menghini et al. [26] and Les et al. [27] using Ellman's method with slight changes. The sample solution (2 mg/mL, 50 μL) was mixed with Ellman's reagent DTNB (5,5-dithio-bis(2-nitrobenzoic) acid, 125 μL) and acetylcholinesterase (AChE) or butyrylcholinesterase (BChE) in buffer (Tris-HCl, pH 8.0, 25 μL). ...
... The antidiabetic properties of the three Salvia extracts were tested based on their in vitro inhibitory capacity on α-amylase and α-glucosidase [25,27]. In α-amylase assay, sample solutions (2 mg/mL, 25 μL) were premixed with the α-amylase solution (50 μL) in phosphate buffer (pH 6.9) ...
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Even though Salvia genus is one of the most known and studied taxa of Lamiaceae family, the knowledge regarding the chemical composition and health-related benefits of some locally used Salvia species (mostly endemic) is still scarce. In this regard, the present work aims to evaluate the chemical profile and potential bioactivities of 70% (v/v) ethanolic extracts obtained from the less-studied S. transsylvanica and S. glutinosa in comparison with S. officinalis. HPLC-PDA analysis revealed the presence of rutin and catechin as the main compounds in the extracts of the three studied species (using the employed HPLC method), whereas the presence of naringenin was highlighted only in S. glutinosa extract. Chlorogenic acid, rutin and quercetin were identified and quantified for the first time in S. transsylvanica extracts. The in vitro antioxidant capacity of each extract was tested through complementary methods (phosphomolybdenum assay, DPPH, ABTS, CUPRAC and FRAP assays), and correlated with the presence of phenolics (especially flavonoids) in high amounts. The neuroprotective and antidiabetic abilities of S. officinalis (the most active as AChE, BChE and α-glucosidase inhibitor), S. glutinosa (the most active as α-amylase inhibitor) and S. transsylvanica were also studied. For each extract it was determined the antimicrobial, antifungal and cytotoxic effects using in vitro assays. The obtained results confirm the potential of S. transsylvanica and S. glutinosa as promising sources of bioactive compounds and as a starting point for further analyses.
... From a systematic point of view, Helichrysum Mill. is a large genus, with a worldwide distribution (Azizi et al., 2014a, b;Azizi et al., 2019). The most well-known and studied species of this genus are H. italicum (Antunes Viegas et al., 2014), H. stoechas (Les et al., 2017), and H. arenarium (Pljevljakušić et al., 2018). Studies show that Helichrysum spp. ...
Article
The plants belonging to the genus Helichrysum (Asteraceae) are known as everlasting flowers and widely used in traditional medicine worldwide. Surveys on their traditional uses as well as phytochemical and pharmacological studies have revealed the potential of these plants for drug discovery. Although there are several studies on some of the species, most of the plants need to be investigated thoroughly. The aim of this review is to present a collated and coherent overview of the documented traditional uses, pharmacological activities and particularly bioactive constituents of Helichrysum species. Scientific databases including Scifinder, ISI Web of Knowledge, PubMed and Scopus as well as several traditional texts and books were searched to collect the data. Review of studies showed that Helichrysum spp. have been used in different systems of traditional and folk medicines for the treatment of various infections, wounds, digestive problems, diabetes and colds, of which some are confirmed in modern medicine such as the antimicrobial activity. Phytochemical investigations have shown that these plants are rich in phenolic compounds such as flavonoids, pyrones, phloroglucinols and essential oils, and in some species terpenes such as sesquitepenes and diterpenes are dominant. However, among these compounds, pyrones and phloroglucinols have been reported to be the bioactive constituents in most of the studies. Overall, according to the potential of these plants, further phytochemical, ethnopharmacological and pharmacological studies are required since only a few species have been investigated so far.
... The α-glycosidase inhibitory assay was adapted from the methodology previously described by Les et al. (2017) and Spínola and Castilho (2017). The assay was conducted in a 96-well microplate with a reaction mixture containing 50 μL of extract sample diluted in 50 μL of 100 mM-phosphate buffer (pH 6.8) and 50 μL yeast α-glucosidase (2 U/mL in same buffer). ...
Article
Cytinus hypocistis whole plant and its three different parts (petals, stalks, and nectar) were chemically characterised and their biological properties evaluated. A total of 17 phenolic compounds were identified, being galloyl-bis-HHDP-glucose the most abundant. All the tested extracts showed high antioxidant capacity, with the petals exhibiting the most promising results both in the OxHLIA (IC50 = 0.279 ng/mL) and TBARS (IC50 = 0.342 ng/mL) assays. For the antidiabetic and anti-tyrosinase enzyme inhibitory assays, the stalk extract presented the lowest IC50 values, 0.039 mg/mL and 0.09 mg/mL, respectively. Regarding antibacterial activity, all tested extracts displayed broad-spectrum microbial inhibition against both Gram-positive and Gram-negative bacteria. Similarly, all extracts displayed effective anti-proliferation activity against four tested tumour cell lines (NCI-H460, HeLa, HepG2, and MCF-7), with no toxicity observed for a non-tumour cell line. Considering the anti-inflammatory activity, the petals showed the highest NO inhibition (IC50 = 127 μg/mL). These results point C. hypocistis as a promising source of health-promoting biomolecules.
... The α-glucosidase inhibitory assay was measured according to method described previously [20,21]. In brief, 50 µL of sample diluted in 50 µL 100 mM-phosphate buffer (pH 6.8) in a 96-well microplate, were mixed with 50 µL yeast α-glucosidase for 10 min before 50 µL substrate (5 mM, p-nitrophenyl-α-D-glucopyranoside prepared in same buffer) were added. ...
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The present study aimed, on the one hand, to improve the yield of microwave assisted extraction (MAE) of polyphenols from beech bark by using a design of experiments (DoE) approach. On the other hand, beech bark extracts (BBE) were characterized in terms of their phytochemical profile and evaluated for biological potential (antioxidant, antibacterial, antifungal, antimutagen, anti-α-glucosidase, and anti-tyrosinase). The extraction time varies with the amount of extracted total phenolic content (TPC). The microwave power favors TPC extraction but in different proportions. The optimum conditions which gave the highest TPC (76.57 mg GAE/g dry plant material) were reached when the microwave power was 300 W, extraction time was 4 min, and the solvent was an ethanol-water (50:50) mixture. The practical value of TPC after a controlled experiment was 76.49 mg GAE/g plant material. The identified compounds were vanillic acid, gallic acid, epicatechin, catechin, protocatechuic acid, chlorogenic acid, ferulic acid, and isoquercitrin. The antioxidant potential of BBEs was demonstrated by in vitro experiments. The BBEs were active against Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhimurium, Escherichia coli, and Candida species. All extracts were antimutagenic and expressed an inhibition on α-glucosidase and tyrosinase activity. Regarding antimutagen activity, the assayed extracts may be considered to have low or no antimutagen effects.
... Yet, they are also very useful to reveal new and unexpected potential uses by assessing their biological activities in both in vitro and in vivo studies. (Esposito et al., 2013;Cardile et al., 2015;Parenti et al., 2016;Venditti et al., 2016b;Camilo et al., 2017;Les et al., 2017). The phytochemical analysis may also be employed to detect the presence of toxic constituents, such as in the case of hepatotoxic neo-clerodanes from Teucrium polium L. Venditti et al., 2017aVenditti et al., , 2017b, and revealed to be a useful tool for the quality control of plant raw materials collected for botanical purposes (Toniolo et al., 2014;. ...
Article
In this work, the first phytochemical analysis ever performed on the fruits of Styrax officinalis L. (Styracaceae) collected from a population vegetating in the Mounts Lucretili National Park (Italy) was reported. Fifteen compounds were identified: tri-α-linolenoyl-sn-glycerol (1), 1,2-di-α-linolenoyl-3-linoleoyl-sn-glycerol (2), 1-α-linolenoyl-2-palmitoyl-sn-glycerol (3), 1,2-di-α-linolenoyl-sn-glycerol (4), egonol (5), demethylegonol (6), homoegonol (7), 1,5-anhydro-D-mannitol (8), glucose (9), sucrose (10), 6'''-O-benzoyl-sucrose (11), raffinose (12), lactic acid (13), succinic acid (14) and glutamic acid (15). These compounds belong to seven different classes of natural metabolites and most of them have chemotaxonomic relevance. Moreover, S. officinalis might be an useful source of enantiopure 1,5-anhydro-D-mannitol which has several medicinal potentialities and is a versatile building block in organic synthesis, in particular for what concern the “Green” approaches, of valuable and potentially biologically active molecules. The presence of compounds (1-15) provides also a phytochemical rationale for the ancient ethnopharmacological uses of the species and affords evidences on its nutraceutical potentialities even for their consumption as food in human nutrition as it actually happens for animals.
... More recently, numerous phytochemicals have been valued for their ability to improve symptoms triggered by chronic metabolic conditions like type 1 and T2DM, as well as neurodegenerative diseases. Among these, extracts from plants such as Pterocarpus marsupium, Eugenia jambolana, Helichrysum stoechas and Rheum palmatum have collectively demonstrated positive effects in pathologies of the CNS, which were in part associated with their moderate DPP-IV inhibitory activity (Kosaraju et al., 2014;Les et al., 2017;Wang et al., 2017). However, one extract in particular, known as berberine, has revealed robust neuroprotective, anti-apoptotic, anti-inflammatory and anti-oxidative properties in various animal models of CNS disorders such as AD, PD, stroke, and even depression or anxiety (Kulkarni and Dhir, 2008;Ahmed et al., 2015;Liu et al., 2016;Shen et al., 2016;Maleki et al., 2017). ...
Article
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Dipeptidyl peptidase IV (DPP-IV) is a serine protease best known for its role in inactivating glucagon-like peptide-1 (GLP-1), pituitary adenylate cyclase-activating polypeptide (PACAP) and glucose-dependent insulinotropic peptide (GIP), three stimulators of pancreatic insulin secretion with beneficial effects on glucose disposal. Owing to the relationship between DPP-IV and these peptides, inhibition of DPP-IV enzyme activity is considered as an attractive treatment option for diabetic patients. Nonetheless, increasing studies support the idea that DPP-IV might also be involved in the development of neurological disorders with a neuroinflammatory component, potentially through its non-incretin activities on immune cells. In this review article, we aim at highlighting recent literature describing the therapeutic value of DPP-IV inhibitors for the treatment of such neurological conditions. Finally, we will illustrate some of the promising results obtained using berberine, a plant extract with potent inhibitory activity on DPP-IV.
... Another important source of herbal medicines among Asteraceae taxa is the genus Helichrysum Mill. [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60]. According to Lourens et al. [61] and Pljevljakušić et al. [62], the genus Helichrysum is characterized by acylphloroglucinols, humulone derivatives, flavonoids, chalcones, phenolic acids, phthalides, sterols, coumarins, pyrones, diterpenes, sesquiterpenes, and polyacetylenes. ...
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Helichrysum cymosum is a valuable and well-known medicinal plant in tropical Africa. The current study critically reviewed the medicinal uses, phytochemistry and biological activities of H. cymosum. Information on medicinal uses, phytochemistry and biological activities of H. cymosum, was collected from multiple internet sources which included Scopus, Google Scholar, Elsevier, Science Direct, Web of Science, PubMed, SciFinder, and BMC. Additional information was gathered from pre-electronic sources such as journal articles, scientific reports, theses, books, and book chapters obtained from the University library. This study showed that H. cymosum is traditionally used as a purgative, ritual incense, and magical purposes and as herbal medicine for colds, cough, fever, headache, and wounds. Ethnopharmacological research revealed that H. cymosum extracts and compounds isolated from the species have antibacterial, antioxidant, antifungal, antiviral, anti-HIV, anti-inflammatory, antimalarial, and cytotoxicity activities. This research showed that H. cymosum is an integral part of indigenous pharmacopeia in tropical Africa, but there is lack of correlation between medicinal uses and existing pharmacological properties of the species. Therefore, future research should focus on evaluating the chemical and pharmacological properties of H. cymosum extracts and compounds isolated from the species.
... The α-glucosidase inhibitory assay was measured in a 96-well microplate reader based on [77] with slight modification. In brief, 50 μL of each fruit sample at different concentrations (3.750, 1.875, 0.938, 0.469, 0.234, 0.118, 0.059, 0.029 and 0.015 mg/ mL) dissolved in DMSO diluted in 50 μL 100 mMphosphate buffer (pH 6.8) in a 96-well microplate, was mixed with 50 μL yeast α-glucosidase (2 U/mL) for 10 min prior to addition of 50 μL substrate (5 mM, p-nitrophenyl-α-D-glucopyranoside prepared in same buffer). ...
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Averrhoa carambola L. is a tropical tree with edible fruit that grows at different climatic conditions. Despite its nutritive value and reported health benefits, it is a controversial fruit owing to its rich oxalate content. The present study aimed at investigating aroma and nutrient primary metabolites distribution in A. carambola fruits grown in Indonesia, Malaysia (its endemic origin) versus Egypt, and at different ripening stages. Two techniques were employed to assess volatile and non-volatile metabolites including headspace solid-phase micro-extraction (HS-SPME) joined with gas chromatography coupled with mass-spectrometry (GC-MS) and GC-MS post silylation, respectively. Twenty-four volatiles were detected, with esters amounting for the major class of volatiles in Egyptian fruit at ca. 66%, with methyl caproate as the major component, distinguishing it from other origins. In contrast, aldehydes predominated tropically grown fruits with the ether myristicin found exclusively in these. Primary metabolites profiling led to the identification of 117 metabolites viz. sugars, polyols and organic acids. Fructose (38–48%) and glucose (21–25%) predominated sugar compositions in ripe fruits, whereas sorbitol was the major sugar alcohol (2.4–10.5%) in ripe fruits as well. Oxalic acid, an anti-nutrient with potential health risks, was the major organic acid detected in all the studied fruits (1.7–2.7%), except the Malaysian one (0.07%). It increases upon fruit ripening, including considerable amounts of volatile oxalate esters detected via SPME, and which must not be omitted in total oxalate determinations for safety assessments.
... Lycopodium alkaloids are compounds isolated from plants of Lycopodiaceae and Huperziaceae, with diverse structures including many unusual skeletons of interest from biogenetic and biological points of view, and challenging targets for total synthesis (Hartrampf et al., 2017;Pinto et al., 2017;Saborit et al., 2016;Wang et al., 2017). Alkaloids are known to possess important bioactivities including acetylcholinesterase inhibitory activity (Benamar et al, 2016(Benamar et al, ,2017Les et al, 2017). Since huperzine A, a potent, reversible and selective acetylcholinesterase inhibitor and a promising drug for the treatment of symptoms of Alzheimer's disease was discovered from Huperzia serrata (Thunb. ...
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Lycopodium japonicum Thunb (Lycopodiaceae) is a common and abundant plant widely distributed in China, Japan and countries of Southern Asia and used in traditional Chinese medicine for the treatment of sprains, strains and myasthenia. This review focuses on the phytochemicals and biological actions, with the objective of stimulating further studies on the plant. 132 chemical compounds have been identified and isolated from this plant, and the most important are alkaloids and serratane triterpenoids. The isolated compounds of L. japonicum were shown to possess acetylcholinesterase inhibitory, cytotoxic, anti-inflammatory, anti-HIV-1 and α-glucosidase inhibitory activities. Further studies should be carried out on this plant in order to disclose many more active principles and mechanisms of active components.
... Furthermore the double emulsion/evaporation microencapsulation method was applied to produce microspheres containing H. stoechas extract, which were further successfully incorporated into a moisturizer. Later, Les et al. 142 found a considerably different profile for a methanolic extract of the aerial parts of H. stoechas assessed via liquid chromatography with parallel nuclear magnetic resonance spectroscopy and mass spectrometry (LC-NMR-MS): two heterodimeric phloroglucinols (inclusive arzanol); one homodimeric α-pyrone (helipyrone); three phenolic acids (p-hydroxybenzoic, caffeic, and neochlorogenic acids); one polymethoxylated and two glycosidic flavonoids (5,7-dihydroxy-3,6,8-trimethoxyflavone, isoquercitrin, and quercetagetin-7-O-glucopyranoside), besides to santinol B. Additionally the authors verified significant antioxidant and antiproliferative activities for the methanolic extract and, for the first time, reported the potential of H. stoechas to inhibit the monoamine oxidase a, acetylcholinesterase, and tyrosinase enzymes, not to mention its anti-α-glucosidase and anti-dipeptidyl peptidase-4 activities. Silva et al. 140 reported that chlorogenic acid, cynarin, and arzanol were the main phenolic components of H. stoechas flowers and stems/leaves aqueous extracts with relevant antiacetylcholinesterase properties (IC 50 values of 260.7 and 654.8 μg mL − 1 , respectively). ...
Chapter
Mediterranean basin is abundant with native edible species that have been used in human diet throughout the centuries as an integral part of the so-called Mediterranean diet. Despite their beneficial health effects, consumption of these species was neglected during the last decades due to modern lifestyles and the shift to western diets and ready-to-eat products. However, the surging scientific knowledge about the health benefits of the Mediterranean diet has been the driving force for the recent rekindling of consumers’ and market’s interest for wild edible greens. The present chapter will provide information about the most commonly used wild greens in three Mediterranean countries, Greece, Italy, and Portugal, giving insight into botanical information, common uses, chemical composition, and their health effects. Moreover, considering the increasing market demands for such species, the current trends and future perspectives in the commercial cultivation of wild greens is also highlighted.
... Phytocompounds have an important influence on the metabolism and neutralization of foreign substances, including carcinogens and mutagens. They have the ability to bind free radicals and reactive metabolites of foreign substances, inhibit xenobiotic activating en-zymes, and activate detoxification enzymes [33]. A comprehensive study of phyto compounds as potential protectors in the toxic, genotoxic and mutagenic effects of various environmental pollutants on the body is necessary. ...
... The capacity of inhibition α-glucosidase (from yeast and rat) was measured in a 96-well microplate reader [32,33]. The lyophilized tisane extracts were re-dissolved in water to obtain a stock solution of 8 mg/mL. ...
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The chemical composition and biological properties correlation in several medicinal and aromatic plants is still underexplored, especially in its most common form of consumption as tisane. The present study aims to characterize the organic acids and vitamin E composition of five tisanes and their extracts by High-Performance Liquid Chromatography coupled to a diode-array detector (HPLC-DAD) and HPLC coupled to a fluorescence detector techniques, respectively, and the phenolic composition by HPLC-DAD-ESI/MS (mass spectrometry by electrospray ionization). It also focuses on their bioactive properties, namely antioxidant, antimicrobial, anti-inflammatory, cytotoxic, anti-tyrosinase, and anti-diabetic activities. A Principal Component Analysis (PCA) was performed in order to understand the correlation between the chemical composition and bioactive properties of the tisanes. The tisane 5 (T5) composed by lemon thyme, tutsan, cloves, and cinnamon, was the most promising mixture, presenting the lowest values for the lipid peroxidation inhibition, anti-inflammatory, and anti-diabetic activity. It also presented the highest concentration of phenolic acids (caffeoylquinic acids derivatives), and flavan-3-ols (catechin derivatives). Only the dry plants presented tocopherols. For the antihemolytic, antimicrobial, and cytotoxic activity, T2 and T4 (with lemon thyme) were highlighted as the best herbal mixtures. The PCA proved to be a valid tool to select the most promising tisane according to the bioactivity. These results suggest that the studied tisanes can be source of high added-value bioactive compounds with health-promoting effects and potential for application in the food and nutraceutical industries, among others.
... RT extract has demonstrated the ability to inhibit the AChE, MAO and TYR enzymes, which could explain its traditional uses as a stimulant, memory enhancer or antidepressant, reinforcing its neuroprotective role. Others isolated extracts of plants and flavonoids have demonstrated the capacity to inhibit CNS enzymes [15,18,23,42,43] and decrease the toxicity by Aβ accumulation [15,23,38,44]. Due to these mechanisms, many natural products have neurotherapeutic potential for the prevention and treatment of different CNS disorders. ...
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In traditional medicine, Jasonia glutinosa (L.) DC or rock tea (RT) has been mainly used to treat digestive and respiratory pathologies but also as an antimicrobial or an antidepressant herbal remedy. An ethanolic extract of RT has been demonstrated to have antioxidant and anti-inflammatory effects, which may be explained by its phytochemical profile, rich in polyphenols and pigments. The aim of this study is to investigate the neuroprotective potential of RT. For this purpose, the ethanolic extract of RT is assayed in Caenorhabditis elegans (C. elegans) as an in vivo model, and through in vitro assays using monoamine oxidase A, tyrosinase and acetylcholinesterase as enzymes. The RT extract reduces juglone-induced oxidative stress in worms and increases the lifespan and prevents paralysis of C. elegans CL4176, a model of Alzheimer’s disease; the extract is also able to inhibit enzymes such as acetylcholinesterase, monoamine oxidase A and tyrosinase in vitro. Together these results demonstrate that Jasonia glutinosa is a good candidate with antioxidant and neuroprotective potential for the development of new products with pharmaceutical interests.
... Species from Helichrysum generally are used traditional medicine against kidney stones, inflammation, gallbladder, cold, liver, diabetes and digestive disorders [10,11]. It has been approved by World Health Organization and European Medicines Agency consuming as the infusion or decocation of flowers of species from genus [12]. It is accepted that the curative effects of genus is chiefly due to some antioxidants including mainly flavonoids, coumarins, phenolic acids contents. ...
... The pharmaceutical, cosmetic and perfume industries have taken a strong interest in Helichrysum species because of the specific essential oil (EO) aroma and composition [2]. Extracts from Helichrysum species possess a wide range of pharmacological activities such as antioxidant, antimicrobial, antiatherosclerotic, antiproliferative, antidiabetic, neuroprotective and antiinflammatory activities [3][4][5][6]. There are 16 species in the Helichrysum genus spread across Europe [7]. ...
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This study compared the essential oils (EO) composition of Helichrysum arenarium (Bulgarian populations) with that of the cultivated species H. italicum. The EO composition of H. arenarium and H. italicum were analyzed via gas chromatography. In general, 75 components were identified in H. arenarium EO and 79 in H. italicum EO. The predominant constituents in H. arenarium EO were α-pinene (34.64–44.35%) and sabinene (10.63–11.1%), which affirmed the examined population as a new chemical type. Overall, the main EO constituents of H. italicum originating in France, Bosnia and Corsica were neryl acetate (4.04–14.87%) and β-himachalene (9.9–10.99%). However, the EOs profile of H. italicum introduced from the above three countries differed to some extent. D-limonene (5.23%), italicene, α-guaiene and neryl acetate (14.87%) predominated in the H. italicum introduced from France, while α-pinene (13.74%), δ-cadinene (5.51%), α-cadinene (3.3%), β-caryophyllene (3.65%) and α-calacorene (1.63%) predominated in plants introduced from Bosnia. The EOs of the plants introduced from France and Corsica had similar chemical composition and antimicrobiological activity.
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Pomegranate juice and related products have long been used either in traditional medicine or as nutritional supplements claiming beneficial effects. Although there are several studies on this food plant, only few works have been performed with pomegranate juice or marketed products. The aim of this work is to evaluate the antioxidant effects of pomegranate juice on cellular models using hydrogen peroxide as an oxidizing agent or DPPH and superoxide radicals in cell free systems. The antiproliferative effects of the juice were measured on HeLa and PC-3 cells by the MTT assay and pharmacologically relevant enzymes (cyclooxygenases, xanthine oxidase, acetylcholinesterase and monoamine oxidase A) were selected for enzymatic inhibition assays. Pomegranate juice showed significant protective effects against hydrogen peroxide induced toxicity in the Artemia salina and HepG2 models; these effects may be attributed to radical scavenging properties of pomegranate as the juice was able to reduce DPPH and superoxide radicals. Moderate antiproliferative activities in HeLa and PC-3 cancer cells were observed. However, pomegranate juice was also able to inhibit COX-2 and MAO-A enzymes. This study reveals some mechanisms by which pomegranate juice may have interesting and beneficial effects in human health.
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Hypericum androsaemum is an evergreen shrub spread in the Mediterranean basin and cultivated in sev- eral European countries. The plant bears fleshy and berry-like capsules that ripen from red to shiny black. In several European conutries H. androsaemum has been traditionally used as diuretic, hepatoprotective, wound healing and as an antidepressant agent. The aim of the study was to evaluate the pharmaceu- tical potential of the methanolic extract of H. androsaemum red berries (HASE) through inhibition of CNS enzymes such as monoamine oxidase A (MAO-A), tyrosinase (TYR) and acetylcholinesterase (AChE). HASE was obtained by soxhlet extraction and analysed by HPLC-DAD for the content of ten bioactive con- stituents. HASE activities were measured in terms of monoamine oxidase A (MAO-A), tyrosinase (TYR) and acetylcholinesterase (AChE) inhibition. HASE was very rich of shikimic acid and chlorogenic acid, occurring at concentration of 94941.7 and 39059.1 mg/kg, respectively. HASE was able to inhibit MAO-A and TYR in a dose dependent manner, although activity was not superior to positive control substances. On the basis of HASE composition and inhibitory effects on MAO-A and tyrosinase, red berries might represent an alternative Hypericum to obtain pharmacologically active substances.
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Ethnopharmacological relevance: Helichrysum (Asteraceae) flowers, known as "altın otu, yayla çiçeği, kudama çiçeği", are widely used to remove kidney stones and for their diuretic properties in Turkey. Aim of the study: To determine the curative effect of infusions prepared from capitulums of Helichrysum graveolens (M.Bieb.) Sweet (HG) and H. stoechas ssp. barellieri (Ten.) Nyman (HS) on sodium oxalate induced kidney stones. Materials and methods: Infusions prepared from the capitulums of HG and HS were tested for their curative effect on calcium oxalate deposition induced by sodium oxalate (70mg/kg i.p.). Following the injection of sodium oxalate for 5 days, plant extracts were administered to rats at two different doses. Potassium citrate was used as positive control. Water intake, urine volume, body, liver and kidney weights were measured; biochemical and hematological analyses were conducted on urine and blood samples. Additionally, histopathological examinations were done on kidney samples. Results: H. stoechas extract showed prominent effect at 156mg/kg dose (stone formation score: 0.33), whereas number of kidney stones was maximum in sodium oxalate group (stone formation score: 2.33). The reduction in the uric acid and oxalate levels of urine samples and the elevation in the urine citrate levels are significant and promising in extract groups. Some hematological, biochemical and enzymatic markers are also ameliorated by the extracts. Conclusions: This is the first report on the curative effect of immortal flowers. Our preliminary study indicated that Helichrysum extracts may be used for treatment of urolithiasis and Helichrysum extracts are an alternative therapy to potassium citrate for patients suffering from kidney stones.
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The extracts from 25 plant species from Salvia, Hypericum, Onosma, Thymus, Origanum, Rosa, and Prunus with eight isolated compounds were screened for their memory-vitalizing potential against the enzymes, i.e., acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase (TYR) along with DPPH, DMPD, and NO radicals and iron-chelation capacity using spectrophotometric microtiter assays. The n-hexane:dichloromethane (1:1) extract of Onosma nigricaule roots (63.18. ±. 0.56%) and the ethyl acetate extract of the aerial parts of Hypericum capitatum var. capitatum (50.79. ±. 3.88%) were the most active toward AChE and BChE, respectively. The highest iron-chelating capacity was found in the n-hexane extract of Thymus sipyleus subsp. sipyleus var. sipyleus, where mostly Labiatae species exhibited better radical scavenging effect. Among the extracts, the roots of O. nigricaule, the aerial parts of Hypericum capitatum var. capitatum and T. sipyleus subsp. sipyleus var. sipyleus could be further evaluated for their memory-vitalizing properties based on different mechanisms.
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In this study, we reported the analysis of the medium polarity fraction obtained from an accession of Helichrysum microphyllum subsp. tyrrhenicum from La Maddalena Island. Besides several compounds already evidenced in this species and related genera, i.e. micropyrone (1), arzanol (2), helipyrone (3), acetyl-bitalin derivatives (4, 5), gnaphaliol (6), caffeic acid (7), ursolic acid (8), 7-O-β-(d-glucopyranosyl)-5-methoxy-1(3H)-isobenzofuranone (9), gnaphaliol-9-O-β-d-glucopyranoside (11) and gnaphaliol-3-O-β-d-glucopyranoside (12), the presence of a new glycosidic phthalide, 6-O-β-(d-glucopyranosyl)-4-methoxy-1(3H)-benzofuranone (10), was evidenced for the first time, which resulted in a structural isomer of compound (9). The occurrence of this new benzofuranone derivative is an additional evidence of the deep intraspecific variability expressed by this species, which was also stated for the non-volatile components, and may be a distinctive trait of the population growing on La Maddalena Island.
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Caffeic acid phenethyl ester (CAPE), a naturally occurring compound isolated from propolis extract, has been reported to have a number of biological and pharmacological properties, exerting antioxidant, anti-inflammatory, anticarcinogenic, antibacterial and immunomodulatory effects. Recent in vivo and in vitro study findings have provided novel insights into the molecular mechanisms involved in the anti-inflammatory and immunomodulatory activities of this natural compound. CAPE has been reported to have anti-inflammatory properties involving the inhibition of certain enzyme activities, such as xanthine oxidase, cyclooxygenase and nuclear factor-κB (NF-κB) activation. Since inflammation and immune mechanisms play a crucial role in the onset of several inflammatory diseases, the inhibition of NF-κB represents a rationale for the development of novel and safe anti-inflammatory agents. The primary goal of the present review is to highlight the anti-inflammatory and immunomodulatory activities of CAPE, and critically evaluate its potential therapeutic effects.
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Context: There is a need for the discovery of novel natural remedies to prevent and treat metabolic disorders such as hyperglycemia, type II non-insulin-dependent diabetes mellitus and obesity. Several Achillea species have been utilized for centuries all around the world and are generally considered effective as hypoglycemic. Objective: Considering the ethnobotanical uses of Achillea genus, we evaluated the in vitro inhibitory activity of Achillea tenorii Grande (Asteraceae) extract on α-glucosidase, which is a valuable target to prevent and treat metabolic disorders. We also tested its antioxidant activity. Moreover, the phytochemical profile was discussed from a chemotaxonomic point of view. Material and methods: In vitro α-glucosidase inhibition of crude ethanolic extract obtained from the aerial parts was assayed as well as the in vitro antioxidant activity (ABTS, DPPH, and FRAP-FZ tests). The extract was characterized by a phytochemical point of view by means of spectroscopic analysis. Results: The extract results endowed with α-glucosidase inhibitory activity (IC50 32 µg/mL) with a particular mechanism of action definable as un-competitive, which differed from the mechanism observed for the best-known α-glucosidase inhibitor (acarbose and miglitol). In addition, a considerable antioxidant potential has been found for A. tenorii extract, which resulted mainly constituted by phenolic compounds as caffeoylquinic acids, and flavonoids. Discussion and conclusions: These results suggest the potential of A. tenorii as a possible natural remedy to prevent and treat metabolic disorders of carbohydrates.
Article
Twenty components (including a new flavanone) were isolated and identified from the whole plant of Anaphalis sinica Hance. Their structures were determined on the basis of spectral analysis and chemical transformation. These components are 6-[(5-methyl-6-ethyl-4-hydroxy-pyrone-3-yl)-methylene]glabranine (1), kaempferol (2), tiliroside (3), quercetin (4), quercetin-3-O-β-D-glucoside (5), scutellarin (6), 5,7-dihydroxy-8-methoxyflavone (7), 5,7-dihydroxy-4′-methoxy-flavone-7-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (8), helipyrone (9), 4′-hydroxydehydrokawain (10), panamin (11), ursolic acid (12), pomolic acid (13), 3-acetyloleanolic acid (14), a mixture of N-(2-hydroxy-acyl)-4-hydroxy-8(E)-ene-sphingenine (15), O-methyl-D-inositol (16), a mixture of β-sitosterol (17) and stigmasterol (18) and a mixture of daucosterol (19) and stigmasterol-β-D-glucoside (20). Among them, 6-[(5-methyl-6-ethyl-4-hydroxy-pyrone-3-yl)-methylene]glabranine (1) is a new compound, and 13C NMR data of panamin (11) is reported for the first time.
Article
Aim The aqueous methanolic extracts of two plants from Algeria, Helichrysum stoechas subsp. rupestre and Phagnalon saxatile subsp. saxatile, were investigated for their antioxidant activity. Method Total phenolics, flavonoids, and tannins were determined by spectrophotometric techniques. In vitro antioxidant and radical scavenging profiling was determined by spectrophotometric methods, through: Total antioxidant capacity, and radical scavenging effects by the DPPH and ABTS methods, reducing and chelating power, and blanching inhibition of the β-carotene. Results All of the extracts showed interesting antioxidant and radical scavenging activity. The highest contents in phenolics, tannins, and the highest total antioxidant capacity as gallic acid equivalents of 97.5 ± 0.33 mg GAE/g DW was obtained for the flowers of H. stoechas subsp. rupestre extract in the phosphomolybdenum assay. An extract of the leafy stems of P. saxatile subsp. saxatile revealed the highest content of flavonoids, and the highest antioxidant activity by the radical scavenging and β-carotene assays when compared with standards. The best activity was by the scavenging radical DPPH with an IC50 value of 5.65 ± 0.10 μg·mL−1. Conclusion The studied medicinal plants could provide scientific evidence for some traditional uses in the treatment of diseases related to the production of reactive oxygen species (ROS) and oxidative stress.
Article
The dimeric 4-hydroxy-2-pyrone, heliopyrone, was isolated from Anaphalis araneosa and its structure confirmed by spectral analysis and synthesis.
Article
From the aerial parts of Helichrysum decumbens, three new antifungal phloroglucinol derivatives have been identified. Their structures have been established by UV, IR, EIMS, FAB-MS, 1H NMR and 13C NMR techniques. In addition, the highly methylated flavonoids 3,5-dihydroxy-6,7,8-trimethoxyflavone, 5,7-dihydroxy-3,6,8-trimethoxy-flavone and 3,5-dihydroxy-6,7-dimethoxyflavone have been detected, the latter being a new naturally occurring compound. The phloroglucinols prevented the growth of Cladosporium herbarum in a bio-assay. These secondary metabolises are externally deposited on the plant surfaces.
Article
The isolation of 18 phenolic compounds (alpha-pyrones, phloroglucinols, phenolic acids, flavonoids, and coumarin)from the aerial pails of Helichrysum stoechas var. olonnense is reported.
Article
During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicum subsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a-c, 6-8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysum phenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureus isolates. These observations validate the topical use of Helichrysum extracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.
Article
In the polar fraction of the extract from Helichrysum arenarium roots, the methylene-bis-4-hydroxy-2H-pyran-2-one derivatives, helipyrone and two new homologues norhelipyrine and bisnorhelipyrone, were identified. Two antibacterial glycosides, C19H24O9 and C30H44O14, and the flavonoids galangin, naringenin and kampferol-3-glucoside were also found.
Article
The aim of this work is to catalogue, document, and make known the uses of plants for folk medicine in the western part of the province of Granada (southern Spain). An analysis was made of the species used, parts of the plant employed, preparation methods, administration means, and the ailments treated in relation to pathological groups. The work was performed in 16 municipalities within the study zone. The participants were located mainly by questionnaires distributed in public and private centres. The information, gathered through semi-structured open interviews of a total of 279 people, was included in a database for subsequent analysis. A floristic catalogue of the territory was compiled, enabling analyses of the relevance of certain botanical families in popular medicine. Great diversity was established among medicinal species in the region. A total of 229 species of plants were catalogued for use in human medicine to prevent or treat 100 different health problems covering 14 different pathological groups. The number of references reached 1963. The popular pharmacopoeia of this area relies primarily on plants to treat digestive, respiratory, and circulatory problems, using mainly the soft parts of the plant (leaves and flowers) prepared in simple ways (decoction, infusion). An analysis of the medicinal ritual uses of 34 species and the different symptoms reflected a certain acculturation in relation to ethnobotanical knowledge in the last 20 years. The traditional knowledge of plants was shown in relation to medicinal use, reflecting a striking diversity of species and uses, as well as their importance in popular plant therapy in the study zone. These traditions could pave the way for future phytochemical and pharmacological studies and thereby give rise to new medicinal resources.
Article
The methanolic extracts of 16 Helichrysum species were investigated for their in vitro antioxidant, radical scavenging and antimicrobial activities. All the extracts showed strong antioxidant and radical scavenging activity. The highest total antioxidant capacity as ascorbic acid equivalents (AAE) of 194.64 mg/g dry extract was obtained for Helichrysum noeanum in the phosphomolybdenum assay. The highest IC50 value (7.95 μg/ml) was observed for the extract of Helichrysum stoechas subsp. barellieri in the DPPH assay. The total phenolic contents of the extracts ranged from 66.74 to 160.63 mg gallic acid equivalents (GAE)/g dry extract. The major component present in the extracts was identified as chlorogenic acid followed by apigenin-7-glucoside and apigenin by HPLC analysis. All the extracts showed significant antimicrobial activity against microorganisms containing 13 bacteria and two yeasts in the agar diffusion method.
Article
Based on its capacity to inhibit in vitro HIV-1 replication in T cells and the release of pro-inflammatory cytokines in monocytes, the prenylated heterodimeric phloroglucinyl α-pyrone arzanol was identified as the major anti-inflammatory and anti-viral constituent from Helichrysum italicum. We have now investigated the activity of arzanol on the biosynthesis of pro-inflammatory eicosanoids, evaluating its anti-inflammatory efficacy in vitro and in vivo. Arzanol inhibited 5-lipoxygenase (EC 7.13.11.34) activity and related leukotriene formation in neutrophils, as well as the activity of cyclooxygenase (COX)-1 (EC 1.14.99.1) and the formation of COX-2-derived prostaglandin (PG)E(2)in vitro (IC(50)=2.3-9μM). Detailed studies revealed that arzanol primarily inhibits microsomal PGE(2) synthase (mPGES)-1 (EC 5.3.99.3, IC(50)=0.4μM) rather than COX-2. In fact, arzanol could block COX-2/mPGES-1-mediated PGE(2) biosynthesis in lipopolysaccharide-stimulated human monocytes and human whole blood, but not the concomitant COX-2-derived biosynthesis of thromboxane B(2) or of 6-keto PGF(1α), and the expression of COX-2 or mPGES-1 protein was not affected. Arzanol potently suppressed the inflammatory response of the carrageenan-induced pleurisy in rats (3.6mg/kg, i.p.), with significantly reduced levels of PGE(2) in the pleural exudates. Taken together, our data show that arzanol potently inhibits the biosynthesis of pro-inflammatory lipid mediators like PGE(2)in vitro and in vivo, providing a mechanistic rationale for the anti-inflammatory activity of H. italicum, and a rationale for further pre-clinical evaluation of this novel anti-inflammatory lead.
Article
This study examines the protective effect of arzanol, a pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum, against the oxidative modification of lipid components induced by Cu(2+) ions in human low density lipoprotein (LDL) and by tert-butyl hydroperoxide (TBH) in cell membranes. LDL pre-treatment with arzanol significantly preserved lipoproteins from oxidative damage at 2h of oxidation, and showed a remarkable protective effect on the reduction of polyunsaturated fatty acids and cholesterol levels, inhibiting the increase of oxidative products (conjugated dienes fatty acids hydroperoxides, 7β-hydroxycholesterol, and 7-ketocholesterol). Arzanol, at non-cytotoxic concentrations, exerted a noteworthy protection on TBH-induced oxidative damage in a line of fibroblasts derived from monkey kidney (Vero cells) and in human intestinal epithelial cells (Caco-2), decreasing, in both cell lines, the formation of oxidative products (hydroperoxides and 7-ketocholesterol) from the degradation of unsaturated fatty acids and cholesterol. The cellular uptake and transepithelial transport of the compound were also investigated in Caco-2 cell monolayers. Arzanol appeared to accumulate in Caco-2 epithelial cells. This phenol was able to pass through the intestinal Caco-2 monolayers, the apparent permeability coefficients (P(app)) in the apical-to-basolateral and basolateral-to-apical direction at 2h were 1.93±0.36×10(-5) and 2.20±0.004×10(-5)cm/s, respectively, suggesting a passive diffusion pathway. The results of the work qualify arzanol as a potent natural antioxidant with a protective effect against lipid oxidation in biological systems.
Article
Chemical constituents and antimicrobial activity of the essential oils and crude ethanol extract from apical part of Helichrysum stoechas were investigated. The chromatographic and spectrophotometric analysis revealed that the major components of essential oil were alpha-pinene (59%), limonen (16.7%), alpha-bisabolol (9.6%) and beta-carophyllene (4%). The major components of ethanolic extract were 3 isomers of caffeoylquinic acid, 2 isomeric dicaffeoylquinic acids, a pigenin glucosides, quercetin and kaempferol. Both essential oils and ethanolic extracts had significant antimicrobial activity on Staphylococcus aureus , Staphylococcus epidermis and Klebsiella pneumonae in addition to some pathogenic fungi as Candida albicans .
Article
Identification of plants with anti-inflammatory activity can be successfully based on information gained through knowledge on their traditional use. This is particularly true for biodiversity-rich regions of the world such as the Mediterranean. While such approaches are often single target based, here we used a multitarget, cell-based approach focusing on the pro-inflammatory signaling cascade and especially the NF-kappaB (NF-kappaB) pathway. The plants from South-Eastern Spain were chosen on the basis that they were recorded as having a traditional use against an indication related to inflammation. The primary target was the transcription factor NF-kappaB (using a luciferase-based assay in HeLa cells). In addition extracts were tested in vitro for effects on cytokines (IL-6, IL-8, TNF-alpha) or PGE(2) in monocytes and for potential cytotoxic/pro-apoptotic action as well as for their influence on the cell cycle. Overall, 64 medicinal plant drugs from 61 species were assessed as potential inhibitors of inflammatory mediators to levels of 100-10 microg/ml. Three plants showed the highest level of activity (50 microg/ml) in inhibiting the activation of NF-kappaB in 5.1 cells: Helichrysum stoechas (Asteraceae), Dorycnium pentaphyllum (Fabaceae, s.l.) and Phlomis almeriensis (Lamiaceae). In the tests against the cytokines it was particularly striking to find that a number of species, Bupleurum fruticosum, Chamaespartium tridentatum, Genista ramosissima, Helichrysum stoechas, Mercurialis tomentosa, Ononis ramosissima, Peganum harmala, Picnomon acarna, Retama sphaerocarpa and Santolina viscosa showed extracts that were active at inhibiting TNF-alpha (10 microg/ml). Overall, this project has identified a series of species with an activity profile which merits further phytochemical-pharmacological investigation.
Article
Fractionation of the dicholoromethane extract of the aerial parts of Helichrysum stoechas yielded seven isolates (1-7), which exhibited varying antimicrobial activity against Gram-positive bacteria. Pure compounds 1-3 have been previously reported in the same species and 4 and 5 were identified as italipyrone and plicatipyrone, previously isolated from H. italicum and H. plicatum. The two other isolates are helipyrone (6) and homoarenol (7) mixed with related substances. Compound 6c (4,4'-dihydroxy-5,6,5',6'-tetramethyl-3,3'-methylen-di-pyr-2-one) and 6b helipyrone with one methyl substitution, have not been previously reported in other species.
Article
A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation. The assay detects living, but not dead cells and the signal generated is dependent on the degree of activation of the cells. This method can therefore be used to measure cytotoxicity, proliferation or activation. The results can be read on a multiwell scanning spectrophotometer (ELISA reader) and show a high degree of precision. No washing steps are used in the assay. The main advantages of the colorimetric assay are its rapidity and precision, and the lack of any radioisotope. We have used the assay to measure proliferative lymphokines, mitogen stimulations and complement-mediated lysis.
Article
Liquid Chromatography-Ion Trap Mass Spectrometry with an atmospheric pressure chemical ionization (APCI) interface in the negative and positive-ion modes in parallel to UV-diode-array detection (DAD), was applied for the rapid detection/characterization in crude extracts of the water-soluble antioxidant phenolics from Helichrysum stoechas. APCI-MS provides unequivocal molecular weight data of these compounds and useful information about their structures (diagnostic fragments ions), which were confirmed by the UV-DAD fingerprints. This combined approach allows the identification of ten constituents, including the three naturally occurring isomers of caffeoylquinic acid (CGAs), namely neo-chlorogenic acid, chlorogenic acid and crypto-chlorogenic acid, 2 isomeric dicaffeoyl quinic acids, 2 isomeric naringenin glucosides, quercetin, kaempferol and apigenin glucosides and a tetrahydroxychalcone-glucoside. The water-soluble extract from H. stoechas, standardized in both total polyphenol and kaempferol-3-glucoside content, exhibits strong antioxidant activity in vitro when tested in both artificial membrane systems (phosphatidylcholine liposomes) and in a cell model (rat erythrocytes).
Article
Thin-layer chromatography (TLC) was used to screen for acetylcholinesterase inhibitors from Amaryllidaceae extracts. The TLC plate was developed and then stained using Ellman's reagent, 5,5'-dithiobis-(2-nitrobenzoic acid), to detect acetylcholinesterase activity. The advantages of this TLC assay method were that we could dereplicate the known inhibitor galanthamine, widely occurring in Amaryllidaceae, at an early stage of the isolation procedure. Moreover, there is no disturbance from sample dissolving solvents as in the microplate assay, and it is a very simple method. The detection limits were 10-200 ng for several known acetylcholinesterase inhibitors tested, and it is thus more sensitive than UV or Dragendorff's reagent detection. Also the minimal detectable amount for an acetylcholinesterase inhibitor tested was much less than that needed for the microplate assay. We screened 15 Amaryllidaceae extracts using this TLC method, and chose candidates for acetylcholinesterase inhibitor isolation.
Article
From the capitula of Helichrysum compactum, the flavonoids apigenin, kaempferol, luteolin, naringenin, 3,5-dihydroxy-6,7,8-trimethoxyflavone, kaempferol-3-O-glucoside, luteolin-7-O-glucoside and luteolin-4',7-di-O-glucoside and from the leafy stems apigenin, kaempferol, luteolin, quercetin, apigenin-7-O-glucoside, luteolin-7-O-glucoside, and quercetin-3-O-glucoside were isolated. Extracts of the capitula of H. compactum show antioxidant activity by inhibition of lipid peroxidation and also show antibacterial activity.
Article
An overview of agents causing hypopigmentation in human skin is presented. The review is organized to put forward groups of biological and chemical agents. Their mechanisms of action cover (i) tyrosinase inhibition, maturation and enhancement of its degradation; (ii) Mitf inhibition; (iii) downregulation of MC1R activity; (iv) interference with melanosome maturation and transfer; (v) melanocyte loss, desquamation and chemical peeling. Tyrosinase inhibition is the most common approach to achieve skin hypopigmentation as this enzyme catalyses the rate-limiting step of pigmentation. Despite the large number of tyrosinase inhibitors in vitro, only a few are able to induce effects in clinical trials. The gap between in-vitro and in-vivo studies suggests that innovative strategies are needed for validating their efficacy and safety. Successful treatments need the combination of two or more agents acting on different mechanisms to achieve a synergistic effect. In addition to tyrosinase inhibition, other parameters related to cytotoxicity, solubility, cutaneous absorption, penetration and stability of the agents should be considered. The screening test system is also very important as keratinocytes play an active role in modulating melanogenesis within melanocytes. Mammalian skin or at least keratinocytes/melanocytes co-cultures should be preferred rather than pure melanocyte cultures or soluble tyrosinase.
Article
An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol alpha-pyrone arzanol (1a) as a potent NF-kappaB inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinol-type structure of arzanol and the 1,2,4-trihydroxyphenyl-type structure of the base-induced fragmentation product of homoarenol could be reconciled in light of a retro-Fries-type fragmentation that triggers a change of the hydroxylation pattern of the aromatic moiety. On the basis of these findings, the structure of arenol, the major constituent of the clinically useful antibiotic arenarin, should be revised from 2b to 1b, solving a long-standing puzzle over its biogenetic derivation. An alpha-pyrone (micropyrone, 7), the monoterpene rac-E-omega-oleoyloxylinalol (10), four known tremetones (9a-d), and the dimeric pyrone helipyrone (8) were also obtained. Arzanol inhibited HIV-1 replication in T cells and the release of pro-inflammatory cytokines in LPS-stimulated primary monocytes, qualifying as a novel plant-derived anti-inflammatory and antiviral chemotype worth further investigation.
Helichrysoside: a new acylated flavonoid glycoside from Helichrysum kraussii Sch Bip
  • H A Candy
  • W Wright
Candy, H.A., Wright, W., 1975. Helichrysoside: a new acylated flavonoid glycoside from Helichrysum kraussii Sch Bip. South African J. Chem. 28, 215-219.
Hypopigmenting agents: an updated review on biological, chemical and clinical aspects
  • F Solano
  • S Briganti
  • M Picardo
  • G Ghanem
Solano, F., Briganti, S., Picardo, M., Ghanem, G., 2006. Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res. 19, 550-571. http://dx.doi.org/10.1111/j.1600-0749.2006.00334.x.