Analysis and Characterisation of Anthocyanins in Mulberry Fruit

ArticleinCzech Journal of Food Sciences 28(2) · November 2009with 480 Reads 
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Abstract
X. (2010): Analysis and characterisation of anthocy-anins in mulberry fruit. Czech J. Food Sci., 28: 117–126. The fruit of mulberry (Morus alba L., Moraceae) has been used as medicinal food in China for a long history. The pigment from the fruit extract is a kind of natural colourant for food processing and has potential medical and com-mercial values. This study focuses on the analysis and characterisation of anthocyanins from mulberry pigment. The fresh mulberry fruits were extracted with the solvent of 95% alcohol/0.1% HC l (1:1, ratio) at room temperature for 4 h in the dark. After the isolation using C-18 column, the pigment was identified with UV-Visible Spectroscopy, HPLC-PAD, LC-MS, and 1 HNMR. The results showed that the abundant anthocyanins in mulberry pigment are cya-nidin 3-O-rutinoside (60%) and cyanidin 3-O-glucoside (38%). The minor anthocyanins (totally 2%) are pelargonidin 3-O-glucoside and pelargonidin 3-O-rutinoside.

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  • ... Over 600 naturally occurring ACNs have been reported differing in (a) the number and position of hydroxyl and methoxyl groups in the basic anthocyanidin skeleton, (b) identity, number and positions at which sugars are attached and (c) the extent of sugar acylation and identity of acylating agent [3]. They differ from other natural flavonoids on the basis of colour ranges that can be derived from them and their [4] capability to form resonance structures through pH variation [5]. Therefore, ACNs are regarded as potential candidates for natural colorants in the food industry [6,7]. ...
    ... ACNs are considered as substantial dietary compounds also, owing to their potent free radical scavenging and antioxidant nature in vitro leading to their antihypertensive and anticarcinogenic [4] behaviour against oral, esophageal and colon cancer [5]. In addition, ACNs could promote sharp-sightedness, immune response, blood circulatory system and protection against cardiac diseases [6]. ...
    ... ACNs, placed in dark, also showed almost the same stability at temperature 10 to 25°C (P ˃ 0.05), however, a noticeable reduction in stability occurred with 50% degradation by increasing temperature from 25 to 55°C as it is obvious from Figure 3(b). It has been reported by other authors also temperature elevation leads to the acceleration of ACNs destruction [5]. ...
  • ... It is well established that Aβ peptide-induced neuronal toxicity occurs via oxidative stress induction [18]. As illustrated in Figure 1C, PC12 cells were pre-treated with MNCM extract for 24 h before adding Aβ [25][26][27][28][29][30][31][32][33][34][35] peptides. The Aβ [25][26][27][28][29][30][31][32][33][34][35] peptides are widely used in AD study. ...
    ... As illustrated in Figure 1C, PC12 cells were pre-treated with MNCM extract for 24 h before adding Aβ [25][26][27][28][29][30][31][32][33][34][35] peptides. The Aβ [25][26][27][28][29][30][31][32][33][34][35] peptides are widely used in AD study. Moreover, they have short fragments but retain active domains of Aβ . ...
    ... Interestingly, keracyanin (60%) and kuromanin (38%) were the two main anthocyanins detected in mulberry [31,32]. Keracyanin (610.90 µg/g DW) and kuromanin (730.97 µg/g DW) detected in MNCM extract were in the range of those detected in Korean mulberries (30.6-486.7 µg keracyanin/g DW and 93.2-1364.9 ...
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    Alzheimer’s disease (AD) is the most common form of dementia, characterized by chronic neuron loss and cognitive problems. Aggregated amyloid beta (Aβ) peptides, a product of cleaved amyloid precursor protein (APP) by beta-secretase 1 (BACE-1), have been indicated for the progressive pathogenesis of AD. Currently, screening for anti-AD compounds in foodstuffs is increasing, with promising results. Hence, the purpose of this study was to investigate the extraction conditions, phytochemical contents, and anti-AD properties, targeting Aβ peptides of Morus cf. nigra ‘Chiang Mai’ (MNCM) both in vitro and in vivo. Data showed that the aqueous extract of MNCM contained high amounts of cyanidin, keracyanin, and kuromanin as anthocyanidin and anthocyanins. The extract also strongly inhibited cholinesterases and BACE-1 in vitro. Moreover, MNCM extract prevented Aβ-induced neurotoxicity and promoted neurite outgrowth in neuronal cells. Interestingly, MNCM extract reduced Aβ1–42 peptides and improved locomotory coordination of Drosophila co-expressing human APP and BACE-1, specifically in the brain. These findings suggest that MNCM may be useful as an AD preventive agent by targeting Aβ formation.
  • ... This behavior is due to structural changes of anthocyanin molecules with pH changes. Usually, very acidic pH predominates flavium cation which generally has a maximum absorption in the region of λ max = 520 nm (Qin et al. 2010;Vankar and Shukla 2011). On the other hand, in a basic medium, the band disappeared in the visible region; this phenomenon may be related to the fact that the pH increase results in the appearance of various structures in equilibrium even in unknown proportions for all anthocyanins (Qin et al. 2010). ...
    ... Usually, very acidic pH predominates flavium cation which generally has a maximum absorption in the region of λ max = 520 nm (Qin et al. 2010;Vankar and Shukla 2011). On the other hand, in a basic medium, the band disappeared in the visible region; this phenomenon may be related to the fact that the pH increase results in the appearance of various structures in equilibrium even in unknown proportions for all anthocyanins (Qin et al. 2010). ...
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    Indicators are substances that change color as the pH of the medium. Many of these substances are dyes of synthetic origin. The mulala plant (Euclea natalensis), which roots are commonly used by rural communities for their oral hygiene, and roseira (Hibiscus rosa-sinensis), an ornamental plant, are abundant in Mozambique. Currently, synthetic acid-base indicators are most commonly used but have environmental implications and, on the other hand, are expensive products, so the demand for natural indicators started. This study investigated the applicability of aqueous extracts of H. rosa-sinensis and E. natalensis as acid-base indicators. Ground on this work, the extracts can be used as acid-base indicators. On the basis of the absorption spectroscopy in both the UV-Vis region and previous studies, it was possible to preliminarily pinpoint anthocyanins and naphthoquinones as responsible for the shifting of colors depending on the pH range of aqueous extracts of H. rosa-sinensis and E. natalensis. These natural indicators are easily accessible, inexpensive, easy to extract, environmentally safe, and locally available.
  • ... Cyanidin rhamnosylhexoside Fruit [25] Delphinidin acetylhexoside Fruit [25] Delphinidin hexoside Fruit [25] Delphinidin rhamnosylhexoside Fruit [25] Pelargonidin 3-O-glucoside Fruit [34] Pelargonidin 3-O-rutinoside Fruit [34] Pelargonidin hexoside Fruit [25] Pelargonidin rhamnosylhexoside Fruit [25] Petunidin rhamnosylhexoside Fruit [25] Phenolic acids ...
    ... Cyanidin rhamnosylhexoside Fruit [25] Delphinidin acetylhexoside Fruit [25] Delphinidin hexoside Fruit [25] Delphinidin rhamnosylhexoside Fruit [25] Pelargonidin 3-O-glucoside Fruit [34] Pelargonidin 3-O-rutinoside Fruit [34] Pelargonidin hexoside Fruit [25] Pelargonidin rhamnosylhexoside Fruit [25] Petunidin rhamnosylhexoside Fruit [25] Phenolic acids ...
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    The present review is aimed at providing a comprehensive summary on the botany, utility, phytochemistry, pharmacology, and clinical trials of Morus alba (mulberry or sang shu). The mulberry foliage has remained the primary food for silkworms for centuries. Its leaves have also been used as animal feed for livestock and its fruits have been made into a variety of food products. With flavonoids as major constituents, mulberry leaves possess various biological activities, including antioxidant, antimicrobial, skin-whitening, cytotoxic, anti-diabetic, glucosidase inhibition, anti-hyperlipidemic, anti-atherosclerotic, anti-obesity, cardioprotective, and cognitive enhancement activities. Rich in anthocyanins and alkaloids, mulberry fruits have pharmacological properties, such as antioxidant, anti-diabetic, anti-atherosclerotic, anti-obesity, and hepatoprotective activities. The root bark of mulberry, containing flavonoids, alkaloids and stilbenoids, has antimicrobial, skin-whitening, cytotoxic, anti-inflammatory, and anti-hyperlipidemic properties. Other pharmacological properties of M. alba include anti-platelet, anxiolytic, anti-asthmatic, anthelmintic, antidepressant, cardioprotective, and immunomodulatory activities. Clinical trials on the efficiency of M. alba extracts in reducing blood glucose and cholesterol levels and enhancing cognitive ability have been conducted. The phytochemistry and pharmacology of the different parts of the mulberry tree confer its traditional and current uses as fodder, food, cosmetics, and medicine. Overall, M. alba is a multi-functional plant with promising medicinal properties.
  • ... These results corresponded to the previous studies, which suggested that the predominant anthocyanins found in mulberry (M. alba L.) extracted with acidic ethanol were keracyanin (60%) and kuromain (38%), while traces of pelargonidin 3-O-glucoside and pelargonidin 3-O-rutinoside were also detected at 2% in total [20]. Previous studies also suggested that aqueous ethanolic extracts of five cultivars of Korean mulberry (M. ...
    ... However, opposite results were observed with superoxide anion scavenging capacity, in which delphinidin is the strongest scavenger, followed by cyanidin and pelargonidin, respectively [24]. The effect of the environment is related to sensitivity of detected anthocyanins/anthocyanidins, which also depend on extraction methods, including pH, temperature, and light exposure [20]. Interestingly, the degree and position of hydroxyl, methoxyl, and sugar moieties of anthocyanins/anthocyanidins play a significant role in their antioxidant capacities. ...
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  • ... The dominant pericarp anthocyanin in red litchi cultivars is cyanidin-3-rutinoside ([93 %) (Wei et al. 2011). Cyanidin-3-rutinoside is also the main anthocyanin in the fruits of Morus alba (Qin et al. 2010), Rubus idaeus (Sparzak et al. 2010), Rubus glaucus, and Solanum betaceum (Osorio et al. 2012). LcUFGT1 is responsible for the formation of cyanidin-3-glucoside in the pericarp of litchi (Li et al. 2016). ...
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    Glycosylation plays a major role in the diversity in the chemical compositions of flavonoids. In this study, we performed biochemical and molecular assays to identify a glucosyltransferase gene responsible for the anthocyanin composition in litchi. Cyanidin-3-glucoside and cyanidin-3-rutinoside were predominant anthocyanins in the red pericarp and young leaf of litchi. Anthocyanin composition varied among litchi varieties. Anthocyanin profile was primarily determined by genetic factors. Higher activities of UDP-rhamnose: cyanidin-3-glucoside rhamnosyltransferase (CGRT) were detected in the pericarps of the cyanidin-3-rutinoside predominant varieties. Three full-length putative UDP-rhamnose: flavonoid glycoside 2″-O-beta-l-rhamnosyltransferase-like genes were isolated and designated as LcFGRT2, LcFGRT4, and LcFGRT5. Phylogenetic analysis showed that these genes were clustered with other glucoside-glycosyltransferases. Notable activities in catalyzing cyanidin-3-rutinoside formation were observed in extracts of tobacco leaves and yeast with heterologous expression of LcFGRT4. However, the expression pattern of LcFGRT4 did not agree with the CGRT activity. This result suggests that the difference in CGRT among varieties occurred post-transcriptionally. Nucleotide variation in LcFGRT4 was surveyed by sequencing 30 litchi accessions with different anthocyanin profiles. Eight non-synonymous single-nucleotide polymorphisms were detected. Type A LcFGRT4 sequence (LcFGRT4A) was observed in cyanidin-3-glucoside-dominant varieties, whereas type B LcFGRT4 sequence (LcFGRT4B) was detected in cyanidin-3-glucoside-dominant varieties. A mutant in 343 C/G polymorphism was targeted as the critical point responsible for the CGRT activity. Results indicated that a single-point mutation in LcFGRT4 could alter the activity of CGRT and may contribute to the diverse anthocyanin profile of litchi.
  • ... Phytochemical studies on M. nigra have demonstrated the presence of various minerals (Akbulut and Özcan, 2008), vitamins (β-carotenes, thiamine, riboflavin, niacin, biotin, and ascorbic acid) (Ercisli and Orhan, 2007), polysaccharides (1-deoxynojirimycin, rhamnose, and galacturonic acid) (Iqbal et al., 2012), sterols (β-sitosterol, terpenoids, and sesquiterpenes) and fatty acids (linoleic acid) (Calín-Sánchez et al., 2013), alkaloids (morroles and mulbaines) (Song et al., 2009), anthocyanins (cyanidin-3glucoside, cyanidin-3-rutinoside, and pelargonidin-3glucoside) (Qin et al., 2010), flavonols (morusinol and albanol) (Sugiyama et al., 2013), prenylated flavonoids (albanins, astragalin, cyclomorusins, isomulberrofurans, and kuwanons) (Pawlowska et al., 2008), and phenolic compounds (kaempferol and its derivatives) (Memon et al., 2010). Several studies have reported the presence of antibacterial (Fukai et al., 2005), antithrombotic (Yamamoto et al., 2006), antiviral (Keyaerts et al., 2007), antioxidant (Isabelle et al., 2008;Yu et al., 2014), antityrosinase (Zheng et al., 2010), antihyperuricemic (Wang et al., 2011), antiatherogenic (Chan et al., 2013), antidiabetic (He and Lu, 2013), antiinflammatory (Chao et al., 2013), anticancer (Qadir et al., 2014), and antifungal (Shukla et al., 2014) activities in various phytochemicals isolated from black mulberry. ...
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    Morus nigra Linn. (black mulberry) is used in gastrointestinal ailments. This study demonstrates gut modulatory properties of M. nigra. The prokinetic, laxative, and antidiarrheal activities of M. nigra were assessed in mice, while isolated rabbit jejunum and guinea-pig ileum were used to explore insight into mechanism(s). At 30 and 70 mg/kg, the crude extract of M. nigra (Mn.Cr) exhibited atropine-sensitive prokinetic and laxative effects, similar to carbachol (CCh). While at higher doses (100, 300, and 500 mg/kg), Mn.Cr offered protection against castor oil-induced diarrhea. In rabbit jejunum, Mn.Cr and its chloroform fraction inhibited CCh-induced contractions more potently compared with high K(+) (80 mm). Conversely, petroleum fraction was more potent against high-K(+) -induced contractions. At 0.01 mg/mL, Mn.Cr caused a parallel shift in acetylcholine concentration-response curves (CRCs) followed by a non-parallel shift at 0.03 mg/mL, similar to dicyclomine. At further tested concentrations, Mn.Cr (0.1 and 0.3 mg/mL) and petroleum fraction suppressed Ca(2+) CRCs, similar to verapamil. In guinea-pig ileum, Mn.Cr, its aqueous and ethyl acetate fractions exhibited atropine-sensitive gut stimulant activity along with additional uncharacterized excitatory response in the aqueous fraction only. These results suggest that black mulberry possesses prokinetic, laxative, and antidiarrheal effects, putatively mediated through cholinomimetic, antimuscarinic, and Ca(2+) antagonist mechanisms, respectively. Copyright © 2016 John Wiley & Sons, Ltd.
  • ... The spectra showed that the maximum absorbance is at a wavelength of 280 nm, and there is also a peak at a wavelength of 325 nm and 540 nm. Depending on appropriate literature on the identification of anthocyanin extract, the spectra from fractions showed the spectrum anthocyanin acyl group [14][15][16][17][18][19]. was the mixture containing the fraction absorbance or the standard absorbance. ...
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    Objective: Purple sweet potato (Ipomoea batatas L.) contains antioxidant compounds like anthocyanins (cyanidin and peonidin). Therefore, the current study was conducted to obtain anthocyanins fractions from purple sweet potato with evaluation of its antioxidant activity following ferrous ion chelating (FIC) method and comparing its activity with Na2 EDTA. Furthermore, the oxidative molecular mechanism of purified fractions was investigated by in silico molecular docking to superoxide dismutase (SOD) and glutathione peroxidase (GPX). Methods: Evaluating antioxidant activity by using FIC method performed by observing the absorbance of a mixed solution of (NH4)2 Fe (SO4)2, ferrozine and purified fraction measured using a UV-Vis spectrophotometer. Linear regression was used to calculate the IC50 value. Molecular docking was performed using 4. 2 Autodock program. Data obtained in the form of docking score. Lower binding energy value show the more stable bond between the active compound and its target protein, SOD and GPX. Results: Anthocyanin purified fraction has strong antioxidant capabilities with IC50 value of 74. 44±1. 29 μg/ml, but was significantly lower with Na2 EDTA (p<0. 05). The other mechanism is its ability to induce the target protein such as SOD and GPX intracellular defense body to capture free radicals. But it still lower affinity than native ligand to the target protein GPX is-4. 28 kcal/mol while the native ligand with GPX of-7. 12 kcal/mol. While the bond between peonidin with SOD is greater affinity (-4. 21 kcal/mol) than the native ligand (-0. 86 kcal/mol). Conclusion: Anthocyanin purified fraction of purple sweet potato has a very potent antioxidant activity through two mechanisms as well as the metal chelating by using in vitro assay and free radical scavenger by inducing SOD.
  • ... The spectra showed that the maximum absorbance is at a wavelength of 280 nm, and there is also a peak at a wavelength of 325 nm and 540 nm. Depending on appropriate literature on the identification of anthocyanin extract, the spectra from fractions showed the spectrum anthocyanin acyl group [14][15][16][17][18][19]. was the mixture containing the fraction absorbance or the standard absorbance. ...
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    In the Indonesian health universal coverage system the hypertensive patients that grouped into the refer back patient treatment category, is one target of pharmaceutical home care. The aim of this study was to carried out the impact of pharmaceutical home care on patient compliances and clinical outcomes of hypertension without compeling indication out-patient on Wangaya General Hospital in the municipality of Denpasar Bali. Design research is an experimental study with one group pre-post test design. The thirteen patients who met the inclusion criteria will be given pharmaceutical home care services for 16 visits over three months period. The complianced levels were scored and statistical analyzed using linear regression and wilcoxon test. The pharmaceutical home care visit could increase the patients adherence to antihypertensive drug administration, increasing diet compliance, and adherence of physical exercise from good adherence to excellent adherence (p value=0,001), Pharmaceutical home care visit could increase patient compliance to restrictions of smoking and alcohol consumption from good adherence to very good adherence. The decreasing of the patient’s systolic blood pressure correlated to the pharmacist home visit (p value=0,000). The pharmaceutical home care has influenced on health behavior of hypertensive patients and the patients concordance to take their medication and introduced better clinical outcome.
  • ... To identify the major black mulberry phenolics, LC-MS analysis was performed on the methanolic extracts of the fruit and the juice samples. Two anthocyanins, cyanidin-3-glucoside (peak #1, [M+H] + (m/z) 449) and cyanidin-3-rutinoside (peak #2, [M+H] + (m/z) 595) could be identified based on their molecular mass and maxima in their light absorption spectrum as reported by Qin et al. (2010). In addition, two phenolic esters (3-caffeoylquinic acid (peak #3, [M+H] + (m/z) 355) and 4-cafeoylquinic acid (peak #4, [M+H] + (m/z) 355)) and three flavonols (rutin (quercetin-3-rutinoside) (peak #5, [M+H] + (m/z) 611), quercetin-3-glucoside (peak #6, [M+H] + (m/z) 465), and quercetin-3-malonylglucoside (peak #7, [M+H] + (m/z) 551)) were identified, based on data by Lee and Choi (2012) (Table 3 and Fig. 2). ...
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  • ... The UV-Visible of the extract was taken and found to have 476 nm absorption band. Anthocyanins are characterized by two absorption bands: one is wavelength =280 nm in the UV region and another is 520 nm in the visible region [25]. ...
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  • ... Purplish black color from black mulberry fruit was due to anthocyanin compound; this compound is stable in an acidic environment (pH <5) and 50°C; therefore, the drying temperature was not over 50°C. [28] From the drying process, 846,86 g of black mulberries was obtained. ...
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    Background: Acne is a skin disease characterized by chronic inflammation in the polisebasea that often occurs in adolescence. Utilization of the black mulberry fruit with a high phenolic is one alternative for the treatment of acne. Aims and Objectives: The aims of this research are to develop and test a peel-off mask gel prepared from black mulberries (Morus nigra) extracts, which has antibacterial activity against Staphylococcus epidermidis and Propionibacterium acnes. Materials and Methods: Black mulberry fruit was extracted with the maceration method by using ethanol (96%). Then, the antibacterial activity of the extract was determined by the disc-diffusion method, while the mean inhibitory concentration (MIC) and mean bactericidal concentration (MBC) were determined by the microdilution method. Then, the extract was formulated into the base of the peel-off mask gel containing variations in concentration of polyvinyl alcohol (7%, 9%, and 10%) and hydroxypropyl methylcellulose (2% and 2.5%). The formulations prepared were evaluated for their physical properties, including organoleptic behavior, homogeneity, pH, viscosity, spreadability, and drying time. Irritation tests were performed, and antibacterial activity of the formulation was also assessed. Results: The results showed that the black mulberry fruit extract has antibacterial activity with MIC value of 2.5% against S. epidermidis and P. acnes, while MBC values were 2.5% and 5%, respectively. Formulations with the best results of physical evaluation were obtained for the formula containing polyvinyl alcohol at 7% and hydroxypropyl methyl cellulose at 2.5%. The antibacterial activity of the peel-off mask gel formulation from black mulberries (M. nigra) extract occurs with 3 × MIC and produce inhibition zone 6.11 ± 3.2 mm against S. epidermidis and 5.43 ± 0.6 mm against P. acnes. Conclusion: It can be concluded that the peel-off mask gel prepared from black mulberry (M. nigra) fruit extract is effective as well as safe to be used as a topical preparation.
  • ... The morphological traits of higher performance aggregate fruits have been observed in the Vanch and Rushan valley which showed statistically significant differences from the other districts. Mulberry fruits change the color from green to black purple through red along maturity phases (Qin et al., 2010); in the Western Pamirs five classes of colors were observed for the mulberry fruits ( Table 6). All of them were evidenced in Vanch and Rushan areas and the white color fruits were the most abundant (64.7% and 55.5% respectively). ...
    Article
    The local fruit biodiversity can represent a good opportunity to maintain the agriculture and to develop economies in "marginal" territory such as those in the mountain rural areas. The genetic diversity of the Morus spp. is little known in the Western Pamir mountains, so that the objective of the present study was to improve the knowledge of the polymorphism of the species in the different poorly explored Tajik valleys by investigating the main quantitative and qualitative traits. Materials and methods - Six selected sites of the Gorno Badakhshan Autonomous Oblast (GBAO) region were investigated through field measurement on morphological traits of mulberry trees (both from wild and cultivated habitats). The qualitative analysis on fresh and dried fruits were carried out on four cultivars of the white mulberry (Morus alba L.) and one cultivar of the black mulberry (Morus nigra L.) collected in the Pamir Biological Institute, the highest botanical garden of the Commonwealth of Independent States (CIS). Results and discussion - Our study revealed high variability for all the measured parameters confirmed by a wide polymorphism. The highest rate of variability and the most promising genotypes in terms of fruit morphological traits were observed in the Vanch and the Rushan valleys. Due to the highest ascorbic acid content for the black cv. Shatut and the white cv. Marvori and a better taste, confirmed by the highest reducing and total sugar contents during the early and the full ripening (cv. Bedonia), mulberry fruits can be suggested for the fresh consumption. The cv. Shatut is the only one suggested for sun-drying, following specific local recipes for traditional consumption. Conclusion - The high morphogenetic variability of the mulberry trees in a marginal mountain area as the Gorno Badakhshan in the Western Pamir offers opportunities to make value of fruits with high nutritional and sensory profile and to develop the agricultural resources of any vulnerable territory.
  • ... The GJR extract had eight major components (Figure 1). The UV spectrum was similar to the anthocyanins class reported in the literature (Qin et al. 2010), with a maximum UV absorption at~520 nm, corresponding to cyanidin and delphinidin (Santiago et al. 2014). ...
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    Grape juice residue was incorporated into ice cream at 2.5%, 5.0% and 10.0% to obtain a product with functional characteristics. The chemical composition, colour, total phenolic compounds, antioxidant capacity and sensory acceptance of the ice creams were analysed at day 0 and after 40 days of storage. Ice creams containing grape juice residue had a higher concentration of phenolic compounds and antioxidant activity compared to the control samples. Consumers’ acceptance was similar for all products. At the end of storage, the polyphenol content and antioxidant activity had decreased. Grape juice residue has potential as a natural source of antioxidants to develop new products.
  • ... Anthocyanins are the major components identified in ripened MFs from different regions and the abundance of all the compounds in the anthocyanins group increased during ripening. This was particularly true for the cyanidin-based anthocyanins such as cyanidin-3-O-glucoside (peak E1) and cyanidin rhamnosylhexoside (peak E2), which were reported to be the most abundant type of anthocyanins in ripened MFs (Qin et al., 2010). Pelargonidin-3-O-glucoside (peak E3) was unambiguously characterized by comparison with standards, while peak ...
  • ... 42,43 A small amount of pelargonidin-3-glucoside and pelargonidin-3-rutinoside has been detected in mulberry fruit in addition to C3G and C3R in some reports. 44,45 Using high-speed counter-current chromatography, Du et al. 46 identified five anthocyanins in mulberry fruit: cyanidin 3-O-(6″-O-α-rhamnopyranosyl-β-D-glucopyranoside) (C3RG) (also known as keracyanin), cyanidin 3-O-(6″-Oa-rhamnopyranosyl-β-D-galactopyranoside) (C3RGa), C3G, cyanidin 3-O-β-D-galactopyranoside (C3Ga), and cyanidin 7-O-β-D-glucopyranoside (C7G). In another analytical study, the main anthocyanin was C3RGa, at 41.3% of mulberry anthocyanin extract (MAE), and other isolated pigments were C3RG and petunidin 3-O-β-glucopyranoside. ...
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    Mulberry (Morus alba L.) fruit has a high yield in one fruiting season in many countries, especially in Asia, and a long history of use as an edible fruit and traditional medicine. A great diversity of nutritive compounds such as fatty acids, amino acids, vitamins, minerals and bioactive compounds, including anthocyanins, rutin, quercetin, chlorogenic acid, and polysaccharides have been found in mulberry fruit depending on the cultivars and maturity stages. Furthermore, the extracts and active components of mulberry fruit have demonstrated numerous biological activities, including anti-oxidant, neuroprotective, anti-atherosclerosis, immunomodulative, anti-tumor, anti-hyperglycemic, hypolipidemic activities in vitro and in vivo studies, and received increasing interest from researchers and pharmaceutical companies. Although some mechanistic studies further substantiate these potential health benefits of mulberry fruit, a need exists to make a better understanding of the roles of these compounds in the traditional medicine and the diet. This review provides recent findings regarding the chemical constituents and biological activities of mulberry fruit, which may be useful for stimulating deep research of mulberry fruit and for predicting their uses as important and safe contributors to benefit human health.
  • ... Accumulative lines of evidence have demonstrated that flavonoids, a class of polyphenols found in abundance in vegetables and fruits, can improve cognitive performance across the age groups after a single and repeated administration [6][7]. Several clinical data clearly reveal that anthocyanins, a subclass of flavonoids, significantly enhance cognitive function [8][9][10]. This raises the possibility that an anthocyanin-rich substance can be used as a functional ingredient in food and drinks in order to produce functional food. ...
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    Currently, cognitive enhancers are considered necessary because they play a critical role in daily and social behaviors. The cognitive-enhancing effect of mulberry milk has gained attention due to the cognitive-enhancing effect of this anthocyanin-rich substance and the cognitive-enhancing effect of mulberry fruit in animal models. However, the effect of anthocyanin-rich mulberry milk in clinical trials especially in children is still unknown. This study was a randomized double-blind crossover intervention. A total of forty-six healthy, normal, cognitive subjects aged 6–12 years old were provided mulberry milk (containing mulberry 10 g) or placebo milk (50 mL). Attention and cognitive function were assessed using the auditory odd ball paradigm of event-related potential, whereas working memory was assessed using a computerized battery test. The assessment was performed at baseline and then at 1.5 and 3 hours postdosing. At the end of study period, the activities of acetylcholinesterase (AChE) and monoamine oxidase (MAO) together with that of saliva cortisol were determined. Following mulberry milk intervention, the decreased N100 latency and the increased P300 amplitude were increased both at 1.5 and 3 hours after dosing. The decreased response time of digit updating was observed both at 1.5 and 3 hours after dosing, whereas the decreased response time of picture updating was observed at 3 hours after dosing. In addition, the reduction of saliva cortisol was also observed at both periods. The improvement of attention and cognitive processing capabilities together with the working memory suggests the cognitive-enhancing potential of mulberry milk for school-age children. The possible underlying mechanism may be associated partly with the reduction of cortisol, a stress hormone.
  • ... Morus nigra belongs to Genus Morus known rich in phenolic such as kuwanon E and kuwanon U, chalcone, morusin, moracin, anthocyanin, vanillic acid hexoside, 5-p-Ocoumaroylquinic acid, 4,5-di-O-caffeoylquinic acid, luteolin hexoside, luteolin rutinoside, and quercetin rhamnosyl dihexoside. 19,20,21 Among three extracts that were investigated for antibacterial activity, two extracts including stem bark and fruit ethanol extract had an inhibitory effect against S. epidermidis and P. acnes, but had moderate activity on leaves ethanol extract of black mulberry (Graphic 1). Diffusion method was chosen because this method was simple, rapid, reproducible, and inexpensive. ...
    Article
    Full-text available
    Introduction: the Morus nigra (Moraceae) known as black mulberry is a well-grown plant in Lembang, Indonesia. Previous studies showed that black mulberry fruit has activity as antibacterial and antioxidant. The aims of this study were to evaluate the antibacterial effect of ethanol extract from stem bark, fruit, and leaves of Morus nigra, MIC and morphological changes of the most active extract against Staphylococcus epidermidis and Propionibacterium acnes. Methods: Agar diffusion and microdilution assays were used to evaluate the antibacterial effect of the extract by measuring the zone of inhibition and the minimum inhibitory concentration (MIC) of the extract against the test bacteria. Scanning electron microscopy (SEM) was performed to evaluate the morphological changes induced by the extract in cellular membrane of the bacteria. Protein and ion leakage from the bacterial cells induced by the extract were also evaluated. Results: the antibacterial activity showed the most active extract was an ethanol extract of the stem bark against S. epidermidis and P. acnes with MIC value 4 mg/ml and 2 mg/ml, respectively. The extract also induced protein and ion leakage in test bacterial cells. SEM findings revealed that the extract induced potential cellular membrane damage in 4xMIC. Conclusion: The antibacterial activity was related to the damaged of bacterial cell wall. Keywords: Morus nigra, Staphylococcus epidermidis, Propionibacterium acnes, cellular membrane damage
  • ... This was caused by the fact that the measurements of UV-induced fluorescence (for calculation of the logFER R/UV index) were done with excitation at 375 nm, which is well absorbed by flavonols, but the anthocyanins had a low absorption in this range. On the other hand, anthocyanins contribute to absorption of UV radiation in the UV-B zone with (the absorption maximum *280 nm (Qin et al. 2010) and they contribute to the total flavonoids and total phenolics assessed by the biochemical methods (Fig. 2a, b), although the contribution of anthocyanins to total flavonoids is non-specific (Mabry et al. 1970). Moreover, it was shown that the significant absorbance of anthocyanins at 630 nm (red LED emission) may lead to decrease of FRF R /FRF UV ratio, depending on the concentration of anthocyanins (Tuccio et al. 2011). ...
    Article
    Environmentally induced variation and the genotypic differences in flavonoid and phenolic content in lettuce can be reliably detected using the appropriate parameters derived from the records of rapid non-invasive fluorescence technique. The chlorophyll fluorescence excitation ratio method was designed as a rapid and non-invasive tool to estimate the content of UV-absorbing phenolic compounds in plants. Using this technique, we have assessed the dynamics of accumulation of flavonoids related to developmental changes and environmental effects. Moreover, we have tested appropriateness of the method to identify the genotypic differences and fluctuations in total phenolics and flavonoid content in lettuce. Six green and two red genotypes of lettuce (Lactuca sativa L.) grown in pots were exposed to two different environments for 50 days: direct sunlight (UV-exposed) and greenhouse conditions (low UV). The indices based on the measurements of chlorophyll fluorescence after red, green and UV excitation indicated increase of the content of UV-absorbing compounds and anthocyanins in the epidermis of lettuce leaves. In similar, the biochemical analyses performed at the end of the experiment confirmed significantly higher total phenolic and flavonoid content in lettuce plants exposed to direct sun compared to greenhouse conditions and in red compared to green genotypes. As the correlation between the standard fluorescence indices and the biochemical records was negatively influenced by the presence of red genotypes, we proposed the use of a new parameter named Modified Flavonoid Index (MFI) taking into an account both absorbance changes due to flavonol and anthocyanin content, for which the correlation with flavonoid and phenolic content was relatively good. Thus, our results confirmed that the fluorescence excitation ratio method is useful for identifying the major differences in phenolic and flavonoid content in lettuce plants and it can be used for high-throughput pre-screening and phenotyping of leafy vegetables in research and breeding applications towards improvement of vegetable health effects.
  • ... The light absorbance is colour dependent. Anthocyanins, for example, are able to absorb light within the visible and NIR range (400 -700 nm) whose maximum absorbance is reported usually to be about 520 nm [10] but this differs depending on the type of anthocyanin [11]. Thus, one function of the natural dye is to enhance absorption of light energy (hv) within the visible and NIR regions [12]. ...
    Article
    Full-text available
    An outdoor study on the photoelectrochemical performance of dye-sensitized solar cells (DSSCs) with extracts of leaves of Acalypha wilkesiana ‘Haleakala’ and flowers of Hibiscus sabdariffa as sensitizers was undertaken in which the latter was used as a bench mark. Three extraction methods of natural dyes, namely; aqueous, cold ethanol, and Soxhlet hot ethanol, were employed to investigate their impact on the performance of the dye sensitized solar cells. Aqueous and Soxhlet hot ethanol extracts performed the best for Hibiscus sabdariffa and Acalypha wilkesiana ‘Haleakala’ respectively. Hibiscus sabdariffa yielded the averaged photoelectrochemical performance of light-to-current conversion efficiency of 0.07%, open circuit voltage (Voc) of 0.44 V, short circuit current density (Jsc) of 0.23 mA/cm2; and Acalypha wilkesiana ‘Haleakala’ yielded 0.06% efficiency, Voc of 0.40 V, Jsc of 0.26 mA/cm2. The study for Acalypha wilkesiana ‘Haleakala’ further included varying dye concentrations by dilution. It was found out that the dilution factor Df of 10 (ratio of 1:9) was optimum at which the best efficiency was achieved.
  • ... Therefore, the interest for evaluation of the anthocyanin content within a sample has increased . The analytical methods usually used for anthocyanin characterisation consist of HPLC methods (Lee et al. 2008; Qin et al. 2010; de Villiers et al. 2011; Peña et al. 1997). ...
    Article
    The quality of red wines is given by phenolic compounds and anthocyanins and is associated with colour, taste and therapeutic effects on human health. This work aims to provide a detailed profile of phenolic compounds and anthocyanins that are found in five red wine samples from Dealu Mare-Valea Calugareasca region. The phenolic and anthocyanin profiles of the red wine samples were determined by high-performance liquid chromatography-photodiode array-mass spectrometry and matrix-assisted laser desorption/ionisation–time of flight, respectively. The results obtained showed that Feteasca Neagra had the highest content of phenolic compounds followed by Pinot Noir while the preponderant compound was gallic acid. Amongst anthocyanins, malvidin was found to be the major compound and the highest anthocyanin content was found also for Feteasca Neagra wine. A simple high-performance liquid chromatography-photodiode array-mass spectrometry method was developed, optimised and applied for the quantification of phenolic compounds in red wine samples from Dealu Mare-Valea Calugareasca region. In the same time, a rapid matrix-assisted laser desorption/ionisation–time of flight method that does not need sample preparation was applied for the identification of anthocyanins. Moreover, the phenolic and anthocyanin composition of red wines from Dealu Mare-Valea Calugareasca region is reported for the first time. The phenolic and anthocyanin profile determination will be beneficial for the Romanian winemakers to produce high-quality red wines.
  • ... [32] isolated cyanidin 3-O-glucoside, cyanidin 3-O-rutinoside, pelargonidin 3-O-glucoside and pelargonidin 3-O-rutinoside ultraviolet-visible from mulberry fruits grown in Shaanxi, China using UV-Visible spectroscopy, HPLC-pulsed amperometric detector (PAD), LC-MS and proton nuclear magnetic resonance (1HNMR). Du, et al. [33] isolated cyanidin 3-O-β-D-galactopyranoside, cyanidin 3-O-β-D-glucopyranoside and cyanidin 7-O-β-D-glucopyranoside from mulberry fruits bought from local stores in Hangzhou, China. ...
    Article
    Full-text available
    Mulberry (Morus alba L.) belongs to the Moraceae family and is widely planted in Asia. Mulberry fruits are generally consumed as fresh fruits, jams and juices. They contain considerable amounts of biologically active ingredients that might be associated with some potential pharmacological activities that are beneficial for health. Therefore, they have been traditionally used in traditional medicine. Studies have reported that the presence of bioactive components in mulberry fruits, including alkaloids and flavonoid, are associated with bioactivities such as antioxidant. One of the most important compounds in mulberry fruits is anthocyanins which are water-soluble bioactive ingredients of the polyphenol class. Studies have shown that mulberry fruits possess several potential pharmacological health benefits including anti-cholesterol, anti-obesity and hepatoprotective effects which might be associated with the presence of some of these bioactive compounds. However, human intervention studies on the pharmacological activities of mulberry fruits are limited. Therefore, future studies should explore the effect of mulberry fruit consumption on human health and elucidate the detailed compounds. This paper provides an overview of the pharmacological activities of mulberry fruits.
  • ... 6,7 Sebuah penelitian 959 menyatakan, asupan antosianin dengan mengkonsumsi 1-2 porsi buah berry setiap hari dapat mengurangi risiko penyakit kardiovaskuler 8 dan dapat berfungsi sebagai antiaterosklerosis, anti-karsinogenik, dan antiinflamatori. 9 Banyaknya manfaat antosianin bagi tubuh, maka antosianin memiliki peluang untuk dikembangkan sebagai komponen pangan fungsional. ...
    Article
    Latar Belakang : Buni mengandung antioksidan yang tinggi antosianin, namun jarang dimanfaatkan. Buni ingin dimanfaatkan menjadi suatu produk yang disukai dan dapat menjadi alternatif produk kaya antioksidan, dengan cara pembuatan sari buah. Oleh karena itu dilakukan penelitian tentang pengaruh konsentrasi gula terhadap aktivitas antioksidan dan tingkat penerimaan pada sari buah buni.Tujuan : Mengetahui pengaruh perbedaan konsentrasi gula terhadap kadar antosianin, vitamin C, aktivitas antioksidan, dan tingkat penerimaan sari buah buni (Antidesma bunius).Metode : Penelitian eksperimental dengan rancangan acak lengkap dengan 3 variasi penambahan gula sebesar 16, 18, dan 20%, serta 1 kontrol. Analisis statistik kadar antosianin, vitamin C, dan aktivitas antioksidan menggunakan uji One Way ANOVACI 95% dengan uji lanjut Tukey. Tingkat penerimaan menggunakan uji Friedman dengan uji lanjut Wilcoxon.Hasil : Sari buah buni dengan penambahan gula 16% memiliki kadar antosianin, kadar vitamin C, aktivitas antioksidanpaling tinggi, masing – masing 479.22 mg; 60.72 mg; 73.07%. Saribuah buni dengan penambahan gula 20% memiliki nilai rata – rata paling tinggi untuk warna(3.36) dan aroma(3.40) dengan kriteria “netral” dan rasa (4.04) dengan kriteria “suka”.Simpulan : Ada pengaruh penambahan gula terhadap kadar antosianin, vitamin C dan aktivitas antioksidan sari buah buni. Ada pengaruh penambahan gula terhadap tingkat penerimaan aroma dan rasa, kecuali warna.
  • ... The fruit of M. alba is edible and widely used in the preparation of juices, smoothies, desserts, jams, etc. Additionally, M. alba fruit has a long history of being used as a medicinal food in China to prevent premature graying of hair; nourish the blood and kidneys; and treat fatigue, weakness, dizziness, constipation, urinary incontinence, tinnitus, and anemia [2,3]. Various active biological components of M. alba fruit have been previously reported, including anthocyanins, rutin, quercetin, chlorogenic acid, and polysaccharides [1]. ...
    Article
    Full-text available
    In this study we aimed to compare the chemical composition and biological activity between Morus alba L. leaf extract obtained with 95% v/v ethanol using a pulsed electric field (PEF) and the conventional maceration method. Extracts of M. alba leaves collected from Chiang Mai (CM), Sakon Nakon (SK), and Buriram (BR), Thailand, were investigated for 1-deoxynojirimycin content by high-performance liquid chromatography and for total phenolic content by the Folin–Ciocalteu method. Antioxidant activity was investigated by 2,2′-diphenyl-1-picrylhydrazyl (DPPH), 2,2’-azinobis-3-ethylbenzothiazoline-6-sulphonate (ABTS), and ferric reducing antioxidant power (FRAP) assay. Anti-tyrosinase and anti-hyaluronidase activity was investigated by in vitro spectrophotometry. The results show that this is the first study to indicate PEF as a novel method for enhancing the phenolic content and antioxidant, anti-tyrosinase, and anti-hyaluronidase activity of M. alba leaf extract (P < 0.05). PEF extract of M. alba leaves collected from BR had comparable ABTS•+ scavenging activity to l-ascorbic acid and comparable anti-tyrosinase activity to kojic acid (P > 0.05). On the other hand, PEF extract of M. alba leaves collected from SK exhibited significantly high anti-hyaluronidase activity, comparable to that of oleanolic acid (P > 0.05). Therefore, PEF is suggested for further M. alba leaf extraction in the production of natural whitening and anti-aging cosmetic ingredients.
  • ... Anthocyanins belong to the subfamily of flavonoids and responsible for red to blue and (32,35,36). Out of the 20 components, the chief anthocyanin isolated from mulberry fruit is Cyanidin 3-O-glucoside (301.75 mg/ g of mulberry anthocyanin extract), which exerts antidiabetic and antitumor activity (23,37). ...
    Preprint
    Mulberry (Morus) cultivated worldwide in diverse agro-ecological conditions recognized as the fodder of silkworms (Bombyx mori). In India, ranging from high altitude Himalayan region to coastal region, the farmers generally cultivate these four species of mulberry (Morus alba, M. indica, M. serrata, and M. laevigata). Mulberry fruit is used in traditional medicine for several years in China and also consumed as food material in different countries of Asia and Africa. Mulberry fruit, along with high nutritious value, contains many bioactive phytochemicals that are30 of health benefits and can fight against many diseases. Many researchers attracted to this property of mulberry fruit, and they isolated bioactive polysaccharides, anthocyanins, flavonols, flavonols, phenolic acids, alkaloids, and melatonins. These compounds have antioxidant property and due to this, either in synergistically or in the pure form, these components have direct or indirect curative activity on diabetes, inflammation, tumor, hepatic diseases, immunomodulation, hyperlipidemia, neural damage, and chronic diseases. This tremendous bioactivity of mulberry fruit extract may open up a new dimension in the food and medicine industry. The present review provides recent findings of the phytochemical foundation and their bioactivities, which may encourage many researchers to explore the molecular mechanism of the biological activities which can be used for human welfare.
  • ... In our study, cyanidin glycosides were identified in the dark-colored fruit extracts: Cyanidin 3-O-glucoside and cyanidin 3-O-rutinoside. These cyanidin derivatives are the main representatives of this class of compounds found in mulberry pigment, containing cyanidin 3-O-rutinoside (60%) and cyanidin 3-O-glucoside (38%) [22]. The chromatographic method yielded a lower phenolics content for both leaves and fruits (see Table 3). ...
    Article
    Full-text available
    Two various species of mulberry (Morus sp.) were selected to enrich rape honey with dried leaves or lyophilized fruits (4% w/v). Finally, fruits and leaves of the ‘Ukraińska’ clone were introduced into the honey during creaming in concentrations from 1 to 4% w/v. The total phenolic content, antioxidant activity, anthocyanins content, and polyphenolic profile were tested in plant extracts and enriched honeys. Moreover, α-glucosidase, β-galactosidase, and diastase activities were investigated in honeys. For mulberry extracts, chlorogenic acid isomers and rutin were considered main antioxidant compounds. The antioxidant activity of honey enriched with mulberry leaves increased even more than 50 times, due to introducing numerous phenolic acids and flavonoid glycosides. A significant decrease in the diastase activity in honey depending on the content of added mulberry leaves (almost 50% decrease in the case of 4% addition) was found, suggesting the inhibitory effect of honey with mulberry leaves against carbohydrate hydrolyzing enzymes.
  • ... The UV-Vis spectrum shows two peaks around 280 and 560 nm. Based on the previous study conducted by Qin et al., anthocyanidin-3-O-rutinoside had maximum wavelength on 281.1 and 524.7 nm (Qin et al., 2010). Similarity between those spectra hypothetically indicated that the second isolate was an anthocyanidin-3-O-rutinoside. ...
    Article
    Full-text available
    Wild mulberry (Morus nigra L.) is a kind of berries that has a high content of anthocyanin pigment. Anthocyanin is a natural pigment that has good biological activity so that widely be used as both food and drug ingredients. There are many studies conducted that have isolation anthocyanin from mulberry extract, but most of them used various expensive methods and the process included several steps that make them not cost-effective nor time-efficient. This research was conducted in order to do an isolation of anthocyanin from wild mulberry through a single step. The extraction of compounds was done by maceration and the isolation was done by thin layer chromatography method. The isolation product was identified with reagents, consisting of ferric chloride and sodium hydroxide, and with spectrophotometry methods, consisting of UV-Vis and infrared spectrophotometry. As result, this research was able to isolate anthocyanin from wild mulberry fruit by thin layer chromatography method. The identification with spectrophotometry methods indicated that the isolated compound hypothetically was anthocyanidin-3-O-rutinoside.
  • ... ‫به‬ ‫کامبوچا‬ ‫تهیه‬ ‫می‬ ‫گرفته‬ ‫کار‬ ‫شود‬ ( Jayabalan et al., 2014 Castilla et al., 2006;Day et al., 1997;Demir, 2014 Ahlawat et al., 2017;Kamiloglu et al., 2013;Qin et al., 2010 Yavari et al., 2010;Yavari et al., 2011 ) . Ayed et al., 2017;Chakravorty et al., 2016;Jayabalan et al., 2010;Jayabalan et al., 2007;Sun et al., 2015;Watawana et al., 2017 Chakravorty et al., 2016;Chu and Chen, 2006;Jayabalan et al., 2007;Malbaša et al., 2008;Sun et al., 2015 ...
    Article
    Full-text available
    The possibility of replacing sugar with grape and black mulberry syrups in the production of Kombucha and its effect on pH, acidity, polyphenols, flavonoids, antioxidant activity, glucose and organoleptic properties was investigated during 15 days fermentation. The results showed that the pH of all samples decreased significantly during fermentation. The amounts of the acidity, antioxidant activity, total phenolic and flavonoid compounds of all samples increased during fermentation period, and the highest levels of them were observed in Kombucha samples containing mulberry syrup, mixed syrup, grape syrup and control, respectively. The glucose content decreased during the fermentation process and the highest reduction of glucose was observed in samples including natural syrups. Sensory analysis revealed that although Kombucha beverages made from syrups were slightly darker with sour taste than bright control sample, but based on panelists, Kombucha containing mulberry syrup was competitive with the control sample. The findings of this study indicate the potential of replacing 50% sugar with mulberry syrup to improve the functional Kombucha with less glucose and more amounts of antioxidants and organic acids.
  • ... The UV-Vis spectrum shows two peaks around 280 and 560 nm. Based on the previous study conducted by Qin et al., anthocyanidin-3-O-rutinoside had maximum wavelength on 281.1 and 524.7 nm (Qin et al., 2010). Similarity between those spectra hypothetically indicated that the second isolate was an anthocyanidin-3-O-rutinoside. ...
    Article
    Full-text available
    Wild mulberry (Morus nigra L.) is a kind of berries that has a high content of anthocyanin pigment. Anthocyanin is a natural pigment that has good biological activity so that widely be used as both food and drug ingredients. There are a lot of research had conducted isolation of anthocyanin from mulberry. But, most of them used various expensive methods and the process included several steps that make them not cost-effective and time-efficient. This research was conducted in order to do an isolation of anthocyanin from wild mulberry through a single step. The extraction of compounds was done by maceration and the isolation was done by thin layer chromatography method. The isolation product was identified with reagents, consisted of ferric chloride and sodium hydroxide, and spectrophotometry methods, consisted of UV-Vis and Infrared spectrophotometry. As result, this research was able to isolate anthocyanin from wild mulberry fruit by thin layer chromatography method. The identification with spectrophotometry methods indicated that the isolated compound hypothetically was anthocyanidin-3-O-rutinoside
  • ... By red-purple color of CFE, it may be responsible for anthocyanins which is the water soluble pigment [19]. From the UV absorption peaks, two peaks at λ = 280-290 nm and λ = 500-540 nm were related with some research that found anthocyanin at λ max = 280 and λ max = 520 via UV-Visible absorption spectra [20]. Therefore, these peaks confirmed that CFE is contain anthocyanins. ...
    Article
    Full-text available
    Phenolic compounds are a large group of phytochemical compounds in plants which have antioxidant activity. Hibiscus species were used in traditional medicine in North-America with biological activities. In this study, total phenolic content, total flavonoid content and antioxidant activities of Chaba maple ( Hibiscusacetosella ) flower extract (CFE) in Thailand were investigated. The total phenolic and flavonoid contents were determined by Folin-Ciocalteu assay and aluminum chloride colorimetric method, respectively. Antioxidant activities of CFE were examined by DPPH radical scavenging, ferric reducing antioxidant power (FRAP) and nitric oxide (NO) radical scavenging ability methods. The results showed that total phenolic content and total flavonoid content were 91.22±0.68 mg gallic acid equivalent/g fresh matter and 0.31±0.01 mg quercetin equivalent/g fresh matter, respectively. For antioxidant activities, IC 50 of DPPH radical scavenging was 57.93±0.37 μg/ml, the power of ferric reducing was 1,707.18±1.99 μM and IC 50 of NO radical scavenging was 229.30±0.71 μg/ml. In conclusion, CFE could be potentially used as a new natural bioactive ingredient for nutritional supplements and cosmetics application.
  • ... In particular, mulberry fruit juice has been used as a folk remedy for treating aphtha, asthma, colds, coughs, diarrhea, dyspepsia, edema, fevers, headache, hypertension, and wounds [13]. Mulberry fruits contain a variety of chemical components, including anthocyanins, sugars, organic acids, free amino acids, vitamins, and micronutrients [14]. Chu et al. [15] have previously identi ed apigenin, ca eic acid, chlorogenic acid, gallic acid, luteolin, morin, rutin, kaempferol, and quercetin in mulberry fruit. ...
    Article
    Full-text available
    Mulberry ( Morus alba L.) has been used in East Asia (Korea, China, and Japan) as a medicine because of its various pharmacological effects including the excellent antioxidant properties of its fruit. This study analyzed extracts from 12 varieties of Korean mulberry fruit for flavonoids using ultrahigh-performance liquid chromatography coupled with diode array detection and quadrupole time-of-flight mass spectrometry (UPLC-DAD-QTOF/MS). Six quercetin derivatives were identified by mass spectrometry (MS) based on the [quercetin + H] ⁺ ion ( m/z 303), while four kaempferol derivatives were identified based on the [kaempferol + H] ⁺ ion ( m/z 287). Two new compounds (morkotin A and morkotin C, quercetin derivatives) were identified for the first time in mulberry fruit. The total flavonoid contents of the mulberry fruits ranged from 35.0 ± 2.3 mg/100 g DW in the Baek Ok Wang variety (white mulberry) to 119.9 ± 7.0 mg/100 g DW in the Dae Shim variety. This study has, for the first time, evaluated the flavonoid chromatographic profiles of 12 varieties of Korean mulberry fruits in a following quali-quantitative approach, which will contribute to improved utilization of these fruits as health foods.
  • ... Kefir grains can be added to cow, goat or sheep milk to produce lactic acid, acetic acid, CO 2 , alcohol and aromatic compounds (Rosa et al. 2017) and they can also be applied to ferment different substrates including cheese whey, fruit juice and molasses (Nouska et al. 2015). Black mulberry (Morus nigra L.) is one of the most important species of the genus Morus, with fruits having substantial levels of total phenolics, total flavonoids, and ascorbic acid (Qin et al. 2010). The ripe mulberry fruit is dark red to dark purple, and this colouring arises from the presence of anthocyanins that can prevent oxidation reactions (Eo et al. 2014). ...
    Article
    Mixture of mulberry juice and whey was evaluated as a potential substrate for the production of a beverage by Tibetan kefir grains. Different mulberry juice addition was used. Acidity, pH, volatile flavour compounds as well as microbial communities were determined during 40 h of fermentation at 18°C. Gas chromatography-mass spectroscopy (GC-MS) analysis revealed that ethanol and 3-methyl-1-butanol were dominant alcohols, and ethyl caprylate, ethyl caprate, ethyl acetate and ethyl caproate were the most dominant ester compounds. The microbial communities of fermented beverage were close to kefir grains indicating that they had similar microbial communities gradually during the fermentation process. Lactococcus was frequently detected at the beginning and then Lactobacillus rapidly proliferated after acclimatizing to the fermentation environment. Acetobacter was steadily increasing during the fermentation process. For the fungi, Candida was frequently detected with the highest abundances in almost all samples.
  • ... To identify the major black mulberry phenolics, LC-MS analysis was performed on the methanolic extracts of the fruit and the juice samples. Two anthocyanins, cyanidin-3-glucoside (peak #1, [M+H] + (m/z) 449) and cyanidin-3-rutinoside (peak #2, [M+H] + (m/z) 595) could be identified based on their molecular mass and maxima in their light absorption spectrum as reported by Qin et al. (2010). In addition, two phenolic esters (3-caffeoylquinic acid (peak #3, [M+H] + (m/z) 355) and 4-cafeoylquinic acid (peak #4, [M+H] + (m/z) 355)) and three flavonols (rutin (quercetin-3-rutinoside) (peak #5, [M+H] + (m/z) 611), quercetin-3-glucoside (peak #6, [M+H] + (m/z) 465), and quercetin-3-malonylglucoside (peak #7, [M+H] + (m/z) 551)) were identified, based on data by Lee and Choi (2012) (Table 3 and Fig. 2). ...
  • ... Mulberries are rich in carbohydrates, cellulose, and minerals and contain bioactive substances, mainly polysaccharides (Ercisli & Orhan, 2007;Liu, Hua, & Wang, 2012) and polyphenols. Of polyphenols, resveratrol and anthocyanins scavenge free radicals, protect against cardiovascular diseases, and reduce liver dysfunction (Aramwit, Bang, & Srichana, 2010;Qin et al., 2010). ...
  • ... It summarizes the research on protocyanidins and anthocyanins in the foodstuffs carried out by the candidate in a number of scientific papers and three of them deal with analytical problems related to the anthocyane pigments [4][5][6]. Anyway, identification and quantification of anthocyanes in red fruits is by no means a novel subject matter and quite a number of papers on these issues have already been published in the past decade or more (e.g., [7][8][9][10][11][12]). ...
    Article
    The aim of this study was to revisit the TLC authentication of alimentary products concept based on analysis of anthocyanes with the foodstuffs of plant origin. To this effect, we used two anthocyanins (cyanin and keracyanin) and two anthocyanidins (pelargonidin and delphinidin) as phytochemical standards. The first step was to develop a novel method making use of the RP-18 F254s stationary phase (which ensures mixed-mode retention mechanism with the localized adsorption on the non-bonded silanols) and acetic acid as the mobile phase component. Importantly, similar TLC systems are currently used for the analysis of anthocyanes. Individual steps of our method development enabled a deeper insight in vulnerability of anthocyanins to external conditions resulting in hydrolysis thereof. In this study, it was impossible to fully separate the products of hydrolytic degradation of the test anthocyanins in a single development run and it was only triple development which ensured distinct and symmetrically shaped chromatographic spots, further scrutinized with use of mass spectrometry. The identity of the hydrolytically split fractions was additionally studied with use of the p-aminobenzoic acid (PABA) test. To obtain calibration curves, triple development was employed for cyanin, keracyanin, and pelargonidin, while delphinidin was developed in one development run. The respective LOD and LOQ values were: for spot (i) derived from the cyanin standard, 0.005 and 0.016 μg spot-1; for spot (ii) derived from the cyanin standard, 0.006 and 0.017 μg spot-1; for spot (i) derived from the keracyanin standard, 0.092 and 0.274 μg spot-1; for spot (ii) derived from the keracyanin standard, 0.035 and 0.104 μg spot-1; for the pelargonidin standard, 0.013 and 0.040 μg spot-1; and for the delphinidin standard, 0.036 and 0.108 μg spot-1. The developed method was used to identify and quantify cyanin, keracyanin, pelargonidin and delphinidin in selected alimentary products (syrups, juices and herbal infusions), keeping in mind that the obtained numerical results were of semi-quantitative nature only.
  • Article
    A rapid isocratic HPLC was developed and validated for use in simultaneous analysis of cyanidin and delphinidin extracted from purple cobs of Zea mays L. ceritina Kulesh. (CC), blue petals of Clitoria ternatea L. (CT) and an anthocyanin complex (AC). The method was shown to be rapid, precise and accurate within 5 20 μg/ml (r > 0.997) with limits of detection and quantitation of 0.45 and 1.52 μg/ml for cyanidin and 4.04 and 13.3 μg/ml for delphinidin, respectively. It could quantitatively detect and compare changes in cyanidin and delphinidin from the AC exposed to human gingival epithelium cells.
  • Article
    Anthocyanins play an important role in the colour of red wine or mulberry wine. The effect of anthocyanin structures (substitution therein) on the self-association and colour in an aqueous alcohol solution was investigated in order to provide helpful knowledge about the relationship between anthocyanin structure and colour. The addition of hydroxyl at the C3' position weakens self-association, whereas addition at the C5' position facilitates self-association. However, the hydroxyl substitutions at the C3' and C5' positions enhance colour. The methoxy substitutions at the C3' and C5' positions enhance the self-association and the colour. The replacement of glucoside with the disaccharide rutinoside at the C3 position was detrimental to self-association, but the substitution of rutinoside at the C3 position produced a stronger colour than the substitution of glucoside at the same position. Cyanidin 3-O-glucoside and cyanidin 3-O-rutinoside enhanced colour via intramolecular co-pigmentation instead of self-association. The anthocyanin colour was affected synthetically by the types and positions of the substituent in the anthocyanin molecule.
  • Article
    Over 600 anthocyanins have been identified to date. These structures have been determined by high-performance liquid chromatography (HPLC) coupled to UV-Vis (UV) detector, diode-array detector (DAD), and different mass spectrometry (MS) analyzers, such as ion trap (IT), quadrupole (Q), time-of-flight (TOF) and hybrid analyzers Q-TOF. MS has generally been coupled to different ion sources such as electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI). Moreover, capillary electrophoresis (CE) coupled to DAD and MS detectors has also been used to characterize anthocyanins. Among these analytical methods, the UV-Vis spectra represents a valuable analytical tool for identifying anthocyanins because they have a specific and intense absorbance band in the range of 520 to 560 nm; meanwhile, MS is a powerful tool which can provide information on molecular mass and also structural features of the different constituents. This chapter provides an overview of the uses of HPLC and CE coupled to different detection systems, discussing the fundamentals of sample extraction and separation.
  • Article
    Introduction Drying of mulberries Compositional and nutritional characteristics of mulberries Phytochemicals in mulberries and their by-products Natural antioxidants in mulberries Health effects of mulberries Food application of mulberries and their by-products Conclusions References
  • Article
    Antioxidant activities and hypolipidemic effects of three different anthocyanin-enriched extracts from mulberry fruit(MA), litchi pericarp (LPA) and purple sweet potato (SPA) were investigated. These three extracts were prepared with macroporous resins and their contents of total phenolic compounds were 335.3 mg/g, 242.0 mg/g and 191.9 mg/g, while their contents of total monomelic anthocyanins were 189.2 mg/g, 112.0 mg/g and 41.8 mg/g, respectively. LPA exhibited the highest antioxidant activity, followed by MA and SPA. LPA had the strongest effect in lowering blood TC and TG, and then SPA and MA. All of the extracts increased significantly antioxidant indices of blood and liver of animal models, reduced LDL-C, AL and AI2, and had no obvious effect on HDL-C. The comparative experiment showed that these three extracts could be used to develop functional foods with antioxidant activity and hypolipidemic effect, and extract from mulberry is the best choice considering the regulation of health food in China.
  • Article
    Full-text available
    Mulberry (Morus spp.) of Moraceae family has been regarded as a unique plant on this earth due to its broader geological distribution across the continents; ability to be cultivated in different forms; multiple uses of leaf foliage and its positive impact in environmental safety approach through ecorestoration of degraded lands, bioremediation of polluted sites, conservation of water, prevention of soil erosion and improving air quality by carbon sequestering. Mulberry is also used as a medicinal plant in improving and enhancing the life of human beings by utilizing the biologically active pharmacokinetic compounds found in leaf, stem and root parts. Further industrial exploitation of mulberry through preparation of various products in pharmaceutical, food, cosmetic and health care industries has gained the attention of industrialists. As mulberry is being exploited by sericulture, pharmaceutical, cosmetic, food and beverage industries along with its utilization in environmental safety approach; it is appropriate to call it as a most suitable plant for sustainable development. Through this review paper, all the important characteristics of mulberry were put together for considering it as an ideal plant in providing sustainable future.
  • Article
    Full-text available
    The present work investigated the phenolic profiles (including nonanthocyanin and anthocyanin phenolics), antioxidant activities, and neuroprotective potential of mulberry fruit (MF) (Morus atropurpurea Roxb.) grown in China at different ripening stages. High-performance liquid chromatography-tandem mass spectrometry method (HPLC-MS/MS) was used to identify and quantify the phenolic compounds. The antioxidant capacity, total phenolic content (TPC), total flavonoid content (TFC), and total monomeric anthocyanin content (TAC) were determined using spectrophotometric methods. The neuroprotective effects of MFs at different ripening stages were investigated using Aβ25-35 -treated PC12 cells as the cellular model of Alzheimer's disease. Of the 19 phenolic compounds characterized from the MF extracts, the contents of rutin and anthocyanins increased and that of chlorogenic acid decreased significantly with maturity. At the fully ripened stage, MF extracts showed the highest amounts of TPC (11.23 mg gallic acid equivalents/g fresh weight), TFC (15.1 mg rutin equivalents/g fresh weight), and TAC (1177 mg cyanidin 3-O-glucoside equivalents/100 g fresh weight). Meanwhile, antioxidant activity of MF extracts at this stage was highest according to ABTS (an IC50 value of 4.11 μg/mL) and DPPH (an IC50 value of 10.08 μg/mL) assays. Cellular assays revealed increased cell viability in cells treated with the ripe MF extracts; compared with the control groups, the ripening fruits also increased the antioxidant enzyme levels in PC12 cells. Together, these results suggest that the antioxidant activities and neuroprotective properties of ripening MFs are related to the contents and types of phenolic compounds that are present in the fruits.
  • Article
    Full-text available
    The colors of native pigmented potatoes were extracted, purified and the anthocyanin spectra identified by FTIR and UV Visible in this solution. In the extract, the effect caused by different cooking processes (boiled, fried and microwaved) of native pigmented potatoes was quantified for total anthocyanins (CAT) and total polyphenols (PFT) before and after each process. The content of (CAT) in the native red potato (PST) and purple potato (PWQ) was 59.21 and 19.35 (mg cyanidin 3 glucoside / 100 g) respectively and once processed the potato (PST) decreases its (CAT) to 4.63 (mg cyanidin 3-glucoside / 100g) in the process of cooking by microwave oven, like potato (PWQ) at 1.31 (mg cyanidin 3-glucoside / 100g) in frying. The composition of (PFT) in potato (PST) and (PWQ) of 179.51 and 87.92 (mg gallic acid / 100g) respectively and after processing, are 125.27 (mg gallic acid / 100g) in the microwave oven of the potato (PST) and 12.19 (mg gallic acid / 100g) in potato frying (PWQ). The most severe decrease in (CAT) and (PFT) content, presented the native potato wenq'os, the most severe decrease in (CAT) and (PFT) content, presented the native fried purple potato, which determines that this cooking process has a greater degradation effect on the antioxidant compounds in native pigmented potatoes
  • Article
    Full-text available
    Diet is an essential factor affecting the development of and risk for diabetes mellitus. In search of preventative and therapeutic strategies, it is to be considering the potential role of certain foods and their bioactive compounds to prevent the pathogenesis associated with metabolic diseases. Human consumption of anthocyanins is among the highest of all flavonoids. Epidemiological studies have suggested that the consumption of anthocyanins lowers the risk of diabetes and diabetic complications. Anthocyanins are important natural bioactive pigments responsible for red to blue colour of fruits, leaves, seeds, stems and flowers, which are present in a variety of plant species particularly in berries and cherries. A large number of bioactive anthocyanins, such as cyanidin, malvidin, delphinidin, pelargonidin, peonidin, petunidin and their metabolites have shown multiple biological activities with apparent effects on glucose absorption, glucose uptake, insulin secretion and sensitivity, on the enzymes involved in glucose metabolism, gene expressions, inflammatory mediators, glucose transporters in progression of diabetes and associated complications, such as diabetic retinopathy, nephropathy, neuropathy and diabetic vascular diseases. The versatility of the anthocyanins provides a promising approach for diabetes management than synthetic drugs. Here we summarize effect of several anthocyanins on many in vitro, in vivo and clinical studies and also reveals the mechanisms which could prevent or reverse the underlying mechanisms of diabetic pathologies including promotion of antioxidant, anti-hyperlipidemic, anti-inflammatory and anti-apoptotic activities.
  • Article
    Red light was used to illuminate Monascus purpureus M9 to evaluate its effects on growth, pigments, and citrinin production. The contents of citrinin and six intracellular pigments, rubropunctamine (RUM), monascorubramine (MOM), monascin (MS), ankaflavin (AK), rubropunctatin (RUN), and monascorubrin (MON), from Monascus purpureus M9 were measured using high-performance liquid chromatography (HPLC). The results indicated that continuous illumination with red light promoted mycelial growth, the synthesis and accumulation of pigments, and spore formation in Monascus purpureus M9, especially the production of cleistothecia. Furthermore, five illumination conditions stimulated the production of RUM, MOM, MS, and AK, but inhibited the yields of RUN, MON, and citrinin. Under the optimal red light illumination condition (light intensity: 300 lux, illumination time: 30 min/d, and lighting regime: 12 h), the yields of RUM, MOM, MS, and AK were increased by 53.8%, 75.2%, 42.2%, and 59.4%, respectively, and those of RUN, MON, and citrinin were decreased by 42.6%, 54.5%, and 42.5%, respectively. © 2017, Editorial Board of Modern Food Science and Technology. All right reserved.
  • Article
    Purpose of Review China has a long history in planting mulberry with the most varieties and the largest production in the world. This article provides a brief overview of an important edible fruit and traditional medicine in China—Fructus Mori (FM, mulberry fruit or Morus alba L. fruit), including the main chemical constituents, major bioactivities and the future prospective. Recent Findings Phytochemical studies have revealed that Fructus Mori contains a great diversity of nutritive compounds such as organic acids, amino acids, vitamins, minerals, and bioactive components, including polysaccharides, polyphenolics, anthocyanins, flavonoids, alkaloids, stilbenes, and diels-alder type adducts. Besides, the extracts and active components of FM were reported to have numerous biological activities, including antioxidant, antihyperglycemic, antitumor, hepatoprotective, and neuroprotective activities in in vitro and in vivo studies. Summary This review provides recent findings systematically regarding the structural characteristics and biological activities of FM, which may be useful for stimulating deep research of therapeutic potentials and for predicting their uses as important and safe functional foods to benefit human health.
  • Article
    Introduction. The studying of the chemical composition and biological activity of plant wastes is an actual problem. The Onion – Allium cepa L., the family Alliaceae belong to the plants that form both primary and secondary wastes. Primary wastes of onion – peels, are formed immediately after harvesting. Secondary are formed during processing of food industry.The aim of the study – to learn the qualitative composition and quantitative content of anthocyanins of Onion’s peels of the “Red Baron” and “Mars” varieties.Research Methods. The presence of this group of compounds in the onion peels of both varieties was confirmed by qualitative reactions with alkali and lead acetate and thin-layer chromatography. The modified spectrophotometric method according to State Pharmacopoeia of Ukraine 2 edition monograph “Blueberry fresh fruits” was used for quantitative determination of anthocyanins.Results and Discussion. Malvidin-3-O-glycoside, malvidin-3.5-diglycoside, delphinidin-3-O-glycoside, cyanidin3-O-glycoside, cyanidine-3.5-diglycoside were identified in onion’s peels both varieties. The content of anthocyaninsin Onion`s peels of the “Red Baron” and “Mars” varieties was determined by spectrophotometric method.Conclusions. 5 anthocyanin glycosides were identified in Onion’s peels “Red Baron” and “Mars” varieties using thin layer chromatography. Optimal conditions to maximize the extraction of anthocyans from the Onion peels were selected. The quantitative content of anthocyanins in the Onion peels of the “Red Baron” and “Mars” varieties was determined.
  • Article
    The spectrophotometric characteristics of bugnay (Antidesma bunius) anthocyanins in acidified solutions of copper (Cu2+) and iron (Fe3+) were investigated after one hour of reaction to determine the changes in their absorbance characteristics. Anthocyanins from bugnay were isolated using solid phase extraction followed by evaporation at 40°C. The total anthocyanin content of the extract was determined to be 103.87 ± 2.91 mg/L cyanidin-3O-glucoside equivalents using pH differential method. Maximum absorbance readings at pH 1.0 and 4.5 were determined to be at 520 nm and 350 nm, respectively. Cyanidin-3-glucoside was identified as one of the components of the three pigments in the extract using reversed phase high performance liquid chromatography. At pH 1.0, copper caused greater hypochromic shift of bugnai anthocyanins compared to iron (p<0.01) while iron caused greater hypochromic shift at pH 4.5. Copper also caused hypsochromic shift of anthocyanins from 520nm to 350nm at pH 1.0 but not at pH 4.5. Correlation analysis showed a significant moderate positive correlation between mean % hypochromic shift and concentration of copper ions at pH 1.0 (R2 = 0.603, ρ<0.01) and 4.5 (R2 = 0.533, ρ<0.01), and iron at pH 4.5 (R2 = 0.638, ρ<0.01). The spectroscopic characteristics of bugnay anthocyanins at 350 nm and 520 nm can be used as parameters to detect copper and iron in acidic solutions.
  • Article
    Mulberry (Morus sp.) fruits provide high levels of anthocyanins, quercetin glycoside, and chlorogenic acid. Recently, mulberry’s polyphenols and their functionalities are spotlighted in different ex vivo and in vivo studies. Meanwhile, the deficiency of systematic knowledge on the health effects and polyphenols composition greatly hinders the development of mulberry as a sustainable fruit. This review briefly summarises the polyphenol compositions, metabolism, health benefits, and their stability in different mulberry production steps. These claimed health effects include anti-oxidative, anti-cancer, anti-diabetes, anti-obesity, and other related effects. However, although the current evidence is promising, further clinical studies are needed to evaluate the role of mulberries' polyphenols to support human health. Besides, the mechanisms by which they confer the health benefits, the bioavailability studies on mulberry’s polyphenols are also scarce. We compile the research findings from the available literatures within the last two decades, and we also suggest some future perspectives in this review.
  • Analysis and biological activities of anthocyanins
    • J.-M Konga
    • L.-S Chiaa
    • N.-K Goha
    • T.-F Chiaa
    • R Brouillardb
    Konga J.-M., Chiaa L.-S., Goha N.-K., Chiaa T.-F., Brouillardb R. (2003): Analysis and biological activities of anthocyanins. Phytochemistry, 64: 923-933.
  • Sorption isotherms and drying characteristics of mulberry (Morus alba)
    • M Maskan
    • F Gogus
    Maskan M., Gogus F. (1998): Sorption isotherms and drying characteristics of mulberry (Morus alba). Journal of Food Engineering, 37: 437-449.
    • W B Phippen
    • J E Simon
    Phippen W.B.; Simon J.E. (1998): Anthocyanins in Basil (Ocimum basilicum L.). Journal of Agricultural and Food Chemistry, 46: 1734-1738.
  • Study on the extraction of anthocyanins from grape wine pomace
    • C G Qin
    Qin C.G. (1997): Study on the extraction of anthocyanins from grape wine pomace. Fine Chemicals, 14: 59-61.
  • Article
    The Lamiaceae family, which includes basil, sage, and thyme, has long been recognized as a rich source of diverse and unique anthocyanins. The development of intensely purple pigmented basil in the ornamental and herb trade prompted this examination of eight commercial varieties of purple basils (Ocimum basilicum L.) as a potential new source of anthocyanins. Anthocyanins were isolated and characterized utilizing high-performance liquid chromatography, spectral data, and plasma desorption mass spectrometry. Fourteen different anthocyanins were isolated, consisting of 11 cyanidin-based pigments and 3 peonidin-based pigments. The large-leaf basil varieties, Purple Ruffles, Rubin, and Dark Opal, had an average extractable total anthocyanin content ranging from 16.63 to 18.78 mg/100 g of fresh tissue, while the ornamental small-leaf variety, Purple Bush, had only 6.49 mg/100 g of fresh tissue. The highest concentration of total anthocyanins occurred just prior to flowering, although by day 8 seedlings already had accumulated all 14 anthocyanins. Comparisons were made to other anthocyanin sources, with results showing that purple basils are an abundant source of acylated and glycosylated anthocyanins and could provide a unique source of stable red pigments to the food industry. Keywords: Basil; Ocimum basilicum L.; anthocyanins; HPLC; plasma desorption mass spectrometry
  • Article
    The flavour characteristics of three black mulberry (Morus nigra) cultivars from the Aegean region of Turkey were investigated using GC/MS and sensory analysis techniques. A total of 18 flavour compounds were identified by GC/MS in the three cultivars. Total sugar content varied between 11.3 and 16.2%, pH between 3.60 and 3.80 and total acidity between 1.51 and 1.79%. The sensory assessment indicated that black mulberry has fruity, sweet, sour, musky and woody flavour notes and fruity, acid, musky, leafy and woody-fresh aroma characteristics. The evaluation of GC/MS and sensory data revealed that ethyl linolenate was the most effective compound contributing to the unique flavour of black mulberry.© 2002 Society of Chemical Industry
  • Article
    Anthocyanin composition of black raspberry (Rubus occidentalis) was studied using high-performance liquid chromatography coupled to photodiode array (PDA) detection and electrospray ionization mass spectrometry (LC-ESI/MS) and tandem mass spectrometry (MS/MS). Pelargonidin 3-rutinoside was isolated and identified in black raspberries using HPLC, UV–Vis spectroscopy, MS, and NMR spectroscopy. No pelargonidin derivative had been previously found in Rubus occidentalis. In addition, the presence and identities of four previously reported anthocyanins (cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside) were confirmed by HPLC/MS and MS/MS analyses.
  • Article
    This study aimed to elucidate how sucrose affects the anthocyanin and antioxidant capacity at low pH under high temperature. The interactive role of different sucrose concentrations (20%, 40%, 60%) and pH values (2, 3, 4) on a mulberry anthocyanin model system at different heating times was investigated. A520 (red color) decreased from 0 to 4 h and increased thereafter, degradation index of anthocyanin (DI) increased in the pure anthocyanin system during 68 h of heating. The samples with sucrose showed a DI peak at 17 h, which indicated that severe browning occurred after this period should be along with lower ratio of A420 and A520, and the latter high A520 came from a brown pigment instead of anthocyanin. Furfural content reached a maximum at 26 h during heating, and other caramelization intermediates showed a similar trend during this period. All samples, with or without sucrose, showed increase in polymeric and copigmented anthocyanin and a decrease in the monomeric ones during heating. The browning depends on the pH and sucrose concentration. Samples at pH 2 with higher sucrose showed the most significant browning and the increase of ferric reducing ability of plasma (FRAP) indicated that hydrolysis of sucrose might increase the antioxidant capacity. Further correlation analysis indicated that changes of antioxidant capacity during heating were closely related to the caramelization intermediate developed from sucrose in the sugar added system. Effect of sucrose on the anthocyanin and antioxidant capacity of of mulberry extract during high temperature heating. Tsai P.-J., Delva L., Yu T.-Y., Huang Y.-T., Dufossé L.. Food Research International, 2005, 38(8-9), 1059-1065.
  • Article
    Anthocyanins, present in the berries of Smilax aspera L., a creeping shrub typical of the Mediterranean region, were extracted and identified for the first time. The pigments were extracted from the skin of the berries with of 0.1% HCl in methanol solution, purified on a C-18 solid-phase cartridge and characterized by means of HPLC-DAD-MS analysis. From spectral analysis before and after acid and alkaline hydrolysis, it was noted that pelargonidin 3-O-rutinoside represented about 83% of the total anthocyanin content in the skin of Smilax aspera berries. A low quantity of cyanidin 3-O-rutinoside (13%) was also found. The attractive colour and the great abundance of the plant in the south of Italy make Smilax aspera berries a new and very good source of natural pigments.
  • Article
    Many isoprenylated flavonoids have been isolated from the mulberry tree and related plants (Moraceae). Among them, kuwanons G (1) and H (2) were the first isolation of the active substance exhibiting the hypotensive effect from the Japanese Morus root bark. These compounds are considered to be formed through an enzymatic Diels-Alder reaction of a chalcone (3) and dehydrokuwanon C (4) or its equivalent. Since that time, about 40 kinds of Diels-Alder type adducts structurally similar to that of 1 have been isolated from the moraceous plants. Some strains of Morus alba callus tissues have a high productivity of mulberry Diels-Alder type adducts, such as chalcomoracin (5) and kuwanon J (6). The biosynthesis of mulberry Diels-Alder type adducts has been studied with the aid of the cell strains.
  • Article
    The effects of temperature and pH on the kinetics of the antiradical capacity of mulberry fruit extract were investigated. The browning index (A 420/A 510) increased as pH increased. The change in browning index at pH 2.0 was less than that at pH 4.0. The antiradical capacity increased as browning index increased. The correlation values (slop) of antiradical capacity and browning index were 135.8 (80 °C), 164.4 (90 °C), and 179.7 (100 °C). The antiradical capacity variation was adequately described by both first order and zero order kinetics; however, a zero order kinetic model was proposed because of a better fit. According to the Arrhenius model, the activation energies for antiradical capacity in the range 80–100 °C for the three different pH values were 82.0 kJ/mol for pH 2.0, 70.8 kJ/mol for pH 3.0, and 41.1 kJ/mol for pH 4.0.
  • Article
    New polyhydroxylated alkaloids, (2R,3R,4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine-N-propionamide from the root bark of Morus alba L., and 4-O-α-d-galactopyranosyl-calystegine B2 and 3β,6β-dihydroxynortropane from the fruits, were isolated by column chromatography using a variety of ion-exchange resins. Fifteen other polyhydroxylated alkaloids were also isolated. 1-Deoxynojirimycin, a potent α-glucosidase inhibitor, was concentrated 2.7-fold by silkworms feeding on mulberry leaves. Some alkaloids contained in mulberry leaves were potent inhibitors of mammalian digestive glycosidases but not inhibitors of silkworm midgut glycosidases, suggesting that the silkworm has enzymes specially adapted to enable it to feed on mulberry leaves. The possibility of preventing the onset of diabetes and obesity using natural dietary supplements containing 1-deoxynojirimycin and other α-glucosidase inhibitors in high concentration is of great potential interest.
  • Article
    This study focuses on the impact of anthocyanin structures such as 5-glucosidic substitution and aromatic acylation on anthocyanin, colour and stability at various pH values. Two concentrations (0.05 and 0.15 mM) of cyanidin 3-glucoside (1), cyanidin 3-(2″-glucosylglucoside)-5-glucoside (2), and cyanidin 3-(2″-(2′′′-sinapoylglucosyl)-6″-sinapoylglucoside)-5-glucoside (3) in aqueous solutions were studied at fourteen pH levels between 1.1 and 10.5 during a 98 day period at 10 °C. The three pigments represent the structural variation of many anthocyanins isolated from fruits and vegetables. Colours were expressed by the CIELAB coordinates hab, (hue angle), C* (chroma=saturation), and L* (lightness), as well as by visible absorption maxima (λmax) and molar absorption coefficients (ε). Limitations of using only spectral parameters, such as λmax and ε, to express colour variations, were revealed. Pigment 2 was more unstable than 1 at most pH values, showing lower C* and higher L* values after storage for only hours in neutral and weakly acid solutions. Pigment 3 showed higher colour stability than the nonacylated forms at all pH values but pH 1.1, where all pigments retained their colours in the storage period, and in the most alkaline solutions, where all pigments experienced dramatic colour changes. Of potential importance for some food products, in solutions with pH 4.1 and 5.1, 3 maintained nearly the same hab, C*, and L* values during the whole measuring period (98 days), in contrast to pigments 1 and 2. The hue angle shift towards bluish tones in freshly made samples of anthocyanins with 5-glucosidic substitution, were amplified with aromatic acylation (3) throughout the entire pH range except pH 10.5. The variations in the results emphasizes the importance of structure for anthocyanin properties in fresh and processed fruits and vegetables.
  • Article
    A black, high anthocyanin sorghum variety (Tx430) grown in several environments was analyzed for anthocyanins by spectrophotometric and HPLC methods. The samples were also analyzed for antioxidant activity using the 2,2′-azinobis (3-ethyl-benzothiaziline-6-sulfonic acid) method. Two extracting solvents, 1% HCl in methanol and 70% aqueous acetone, were compared. Sorghum brans had three to four times higher anthocyanin contents than the whole grains. The brans were a good source of anthocyanin (4.0–9.8 mg luteolinidin equivalents/g) compared to pigmented fruits and vegetables (0.2–10 mg/g), fresh weight basis. Acidified methanol extracted the anthocyanins better than aqueous acetone. Luteolinidin and apigeninidin accounted for about 50% of the anthocyanins in the black sorghums. The sorghum grains and their brans had high antioxidant activity (52–400 μmol TE/g) compared to other cereals (<0.1–34 mg TE/g). Black sorghum should be useful in food and other applications, because it is a valuable source of anthocyanins with good antioxidant activity.
  • Article
    Anthocyanins and betalains play important roles both in plant physiology, visual attraction for pollinators and seed dispersers, but also in food mainly defining its aesthetic value. Since anthocyanin and betalain structures allow to predict only part of their appearance, additional chemical and anatomical functions are required to modulate the appearance of plants and coloured food. Physiological effects that the same pigments exert in plants are supposedly similar to those which they show in humans following ingestion of coloured food. Therefore, anthocyanins and betalains both in fresh and also processed fruit and vegetables serve two functions: They improve the overall appearance, but also contribute to consumers' health and well-being.
  • Article
    Drying characteristics of Mulberry (M. alba) including sorption isotherms and drying kinetics were investigated. Adsorption and desorption isotherms at 10, 20 and 30 °C and isosteric heats of sorption were determined. At higher water activities, as the temperature was increased, a crossing of the isotherm curves was detected. Some hysteresis effect decreasing with higher temperature was observed. Mulberry was dried in a pilot plant tray drier with a constant air velocity of 1.2 m s−1 at 60, 70 and 80 °C. Only falling rate drying periods (three falling rate periods) were observed in the mulberry drying experiments. The diffusivity values changed from 2.32 × 10−10 to 2.76 × 10−9 m2s−1 within the given temperature range. Effect of temperature on the diffusivity was expressed by an Arrhenius relation with an activation energy value of 21.2 kJ mol−1.
  • Article
    Qualitative determination of anthocyanins in extracts of red fruits by narrow-bore HPLC/ESI-MS was carried out. This method was used to investigate anthocyanin contents of black bilberry (Vaccinium myrtillus L.), blackberry (Rubus sp.), and mulberry (Morus nigra). An ultraviolet diode array and a mass spectrometer with ESI source were used for detection. Anthocyanin identifications were made by using retention time data and UV-vis and mass spectra and comparing them with those of commercially available standard compounds. The method allowed the identification of fourteen anthocyanins in black bilberry extract, six anthocyanins in blackberry extract, and five anthocyanins in mulberry extract.
  • Article
    Fruits from 107 genotypes of Vaccinium L., Rubus L., and Ribes L., were analyzed for total anthocyanins (ACY), total phenolics (TPH), and antioxidant capacities as determined by oxygen radical absorbing capacity (ORAC) and ferric reducing antioxidant power (FRAP). Fruit size was highly correlated (r = 0.84) with ACY within Vaccinium corymbosum L., but was not correlated to ACY across eight other Vaccinium species, or within 27 blackberry hybrids. Certain Vaccinium and Ribes fruits with pigmented flesh were lower in ACY, TPH, ORAC, and FRAP compared to those values in berries with nonpigmented flesh. ORAC values ranged from 19 to 131 micromol Trolox equivalents/g in Vaccinium, from 13 to 146 in Rubus, and from 17 to 116 in Ribes. Though ACY may indicate TPH, the range observed in ACY/TPH ratios precludes prediction of ACY from TPH and vice versa for a single genotype. In general, TPH was more highly correlated to antioxidant capacity than ACY was. This study demonstrates the wide diversity of phytochemical levels and antioxidant capacities within and across three genera of small fruit.
  • Article
    High-performance liquid chromatography (HPLC) with photodiode array detection was applied for the characterization of anthocyanins in red-fleshed Budd Blood (Citrus sinensis) orange. More than seven anthocyanin pigments were separated within 30 min by using a binary gradient (0.1% H(3)P0(4) in water and 0.1% H(3)PO(4) in acetonitrile) elution on a Prodigy ODS column. Separations by reversed-phase HPLC and semipreparative HPLC on a Prodigy 10-microm ODS Prep column, and acid and alkali hydrolyses were used for identification of anthocyanins. The primary anthocyanins in Budd Blood orange grown in Florida were cyanidin-3-(6"-malonylglucoside) (44.8%) followed by cyanidin-3-glucoside (33.6%). Two other minor pigments were also acylated with malonic acid. Malonated anthocyanins represented the major proportion (>51%) of anthocyanins in Budd Blood orange. Total anthocyanin contents and juice color parameters (CIE L,a,b) were compared with six other Florida-grown blood oranges.
  • Article
    Fifteen anthocyanin structures are reported from an extract of black currant berries (Ribes nigrum L.). These are the 3-O-glucosides and the 3-O-rutinosides of pelargonidin, cyanidin, peonidin, delphinidin, petunidin, and malvidin, cyanidin 3-O-arabinoside, and the 3-O-(6' '-p-coumaroylglucoside)s of cyanidin and delphinidin. The anthocyanins were characterized by means of size exclusion chromatography, high-performance liquid chromatography, UV-visible spectroscopy, and electrospray mass spectrometry. The four main pigments (the 3-O-glucosides and the 3-O-rutinosides of delphinidin and cyanidin) made up >97% of the total anthocyanin content. The minor pigments were enriched from the extract by successive partition against ethyl acetate and by gel fractionation. These chromatographic steps were successfully used to isolate the acylated anthocyanins from the ethyl acetate layer and to separate cyanidin 3-O-arabinoside from the mixture of anthocyanins. The amounts of anthocyanin rutinosides were found to be higher than the amount of the corresponding glucosides for all detected pigments having the same aglycon moiety.
  • Article
    A series of cyanidin-based anthocyanin pigments was investigated to determine the effect of structural variation on a number of chemical and physical properties: CIELAB color coordinates, visual detection thresholds, hydration constants (pK(H)), and in vitro antioxidant activities (ORAC). In addition to individual isolated compounds, purified total pigment isolates from blackberry, elderberry, black carrot, red cabbage, and sweet potato were also examined. Acylation with cinnamic acids shifted color tonality (hue angle) to purple, and markedly increased pK(H) and antioxidant activity, but lowered the visual detection threshold. Glycosidic substitution at the 5 position moved tonalities toward purple and decreased pK(H), and tended to lower the ORAC value, but raised the visual detection threshold. Increasing the number of sugar substituents at the 3 position also affected all of these parameters, however, the extent was not predictable. Antioxidant levels of purified anthocyanin extracts were much higher than expected from anthocyanin content indicating synergistic effect of anthocyanin mixtures.
  • Article
    Among ethanol extracts of 10 edible berries, bilberry extract was found to be the most effective at inhibiting the growth of HL60 human leukemia cells and HCT116 human colon carcinoma cells in vitro. Bilberry extract induced apoptotic cell bodies and nucleosomal DNA fragmentation in HL60 cells. The proportion of apoptotic cells induced by bilberry extract in HCT116 was much lower than that in HL60 cells, and DNA fragmentation was not induced in the former. Of the extracts tested, that from bilberry contained the largest amounts of phenolic compounds, including anthocyanins, and showed the greatest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. Pure delphinidin and malvidin, like the glycosides isolated from the bilberry extract, induced apoptosis in HL60 cells. These results indicate that the bilberry extract and the anthocyanins, bearing delphinidin or malvidin as the aglycon, inhibit the growth of HL60 cells through the induction of apoptosis. Only pure delphinidin and the glycoside isolated from the bilberry extract, but not malvidin and the glycoside, inhibited the growth of HCT116 cells.
  • Article
    The antioxidant activity of the six common anthocyanidins, pelargonidin, cyanidin, delphinidin, peonidin, petunidin, and malvidin, and their glycosidic forms was evaluated in three lipid-containing models [human low-density lipoprotein (LDL) and bulk and emulsified methyl linoleate]. In addition, the radical scavenging activity of the compounds against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical was studied. Most anthocyanins and their aglycons acted as strong antioxidants in emulsion and LDL. Many compounds showed an activity comparable to the well-known antioxidants alpha-tocopherol, Trolox, catechin, and quercetin. In bulk methyl linoleate, anthocyanins and anthocyanidins possessed only a weak antioxidant activity or even oxidation-promoting activity. Depending on the anthocyanidin, different glycosylation patterns either enhanced or diminished the antioxidant power. For the most part, the activities of the glycosides and the aglycons did not differ remarkably in emulsion. In LDL the aglycons showed in general higher activities than the glycosides. In bulk oil, to the contrary, the glycosides were more effective than the aglycons.
  • Article
    Anthocyanin pigments in the berries of baguaçu (Eugenia umbelliflora Berg), a tropical fruit from Brazil, were extracted with 0.1% HCl in ethanol, and the crude anthocyanin extract was purified by Amberlite XAD-7 open-column chromatography. Six major anthocyanins were isolated by preparative HPLC, and their chemical structures were identified by spectroscopic methods (TLC, UV-vis, MS, and (1)H NMR). Delphinidin 3-O-beta-glucopyranoside, cyanidin 3-O-beta-glucopyranoside, petunidin 3-O-beta-glucopyranoside, pelargonidin 3-O-beta-glucopyranoside, peonidin 3-O-beta-glucopyranoside, and malvidin 3-O-beta-glucopyranoside were identified. On the basis of chromatographic data the total anthocyanin content was 342 mg/100 g of fresh baguaçu berries. Therefore, the concomitant presence of six anthocyanins in a single plant species makes this product promising as a new pigment source.
  • Article
    Anthocyanins are naturally occurring compounds that impart color to fruits, vegetables, and plants. They are probably the most important group of visible plant pigments besides chlorophyll. Apart from imparting color to plants, anthocyanins also have an array of health-promoting benefits, as they can protect against a variety of oxidants through a various number of mechanisms. However, anthocyanins have received less attention than other flavonoids, despite this. This article reviews their biological functions and pre-clinical studies, as well as the most recent analytical techniques concerning anthocyanin isolation and identification.
  • Article
    Full-text available
    Cyanidin and its glycosides belong to the anthocyanins, a widespread class of water-soluble plant compounds that are responsible for the brilliant color (red, orange, blue) of fruits and flowers. They are widely ingested by humans as it has been estimated a daily intake around 180 mg, mainly deriving from fruits and red wines. This paper reviews the literature on the biological activities, absorption and metabolism of cyanidins, with emphasis to the antioxidant, antimutagenic and other protective activities ascribed to these compounds. Their role in contrasting development of cancer and other pathologies is also reviewed. It is concluded that a great deal of work is still necessary to i) definitively clarify the metabolism of cyanidins in human beings; ii) assess the dietary burden and variations within and between populations; iii) evaluate the relationship between cyanidin glycosides-rich food consumption and incidence of given pathologies. The amount of work to be performed is even more significant when considering a possible therapeutic use of cyanidin glycosides-based drugs. With this aim, information on absorption, distribution, metabolism and excretion of cyanidin-glycosides administered by main possible routes are largely insufficient. However, consisting findings allow looking at cyanidins as dietary compounds with a potential beneficial role for human health.
  • Article
    An anthocyanin, 1, with the novel 4-substituted aglycone, 5-carboxypyranopelargonidin, was isolated in small amounts from the acidified, methanolic extract of strawberries, Fragaria ananassa Duch., by preparative HPLC after purification by partition against ethyl acetate, Amberlite XAD-7 and Sephadex LH-20 column chromatography. It was identified mainly by 2D NMR spectroscopy and electrospray LC-MS as the 3-O-beta-glucopyranoside of 5-carboxy-2-(4-hydroxyphenyl)-3,8-dihydroxy-pyrano[4,3,2-de]-1-benzopyrylium, an anthocyanidin which is homologous to 5-carboxypyranomalvidin (vitisidin A) reported in red wines and 5-carboxypyranocyanidin recently isolated from red onions. By comparison of UV-Vis absorption spectra, 1 showed in contrast to 2, pelargonidin 3-O-beta-glucopyranoside, a local absorption peak around 360 nm, a hypsochromic shift (8 nm) of the visible absorption maximum, and lack of a distinct UV absorption peak around 280 nm. The similarities between the absorption spectra of 1 in various acidic and neutral buffer solutions implied restricted formation of the instable colourless equilibrium forms, which are typical for most anthocyanins in weakly acidic solutions. The molar absorptivity (epsilon) of 1 varied little with pH contrary to similar values of for instance the major anthocyanin in strawberry, 2. However, 2 revealed higher epsilon-values than 1 at all pH values except 5.1. At pH 5.1, the epsilon-value of 1 (6250) was nearly four times the corresponding value of 2 (1720), which showed the potential of 5-carboxypyranopelargonidin derivatives as colorants in solutions with pH around 5. The colours of 1 and 2 in buffered solutions with pH 1.1 and pH 6.9 have been described by the CIELAB coordinates h(ab) (hue angle), C* (chroma), and L* (lightness).
  • Article
    Anthocyanins are responsible for a variety of bright colors including red, blue, and purple in fruits, vegetables, and flowers and are consumed as dietary polyphenols. Anthocyanin-containing fruits are implicated in a decrease in coronary heart disease and are used in antidiabetic preparations. In the present study, we have determined the ability of anthocyanins, cyanidin-3-glucoside (1), delphinidin-3-glucoside (2), cyanidin-3-galactoside (3), and pelargonidin-3-galactoside (4), and anthocyanidins, cyanidin (5), delphinidin (6), pelargonidin (7), malvidin (8), and petunidin (9), to stimulate insulin secretion from rodent pancreatic beta-cells (INS-1 832/13) in vitro. The compounds were tested in the presence of 4 and 10 mM glucose concentrations. Our results indicated that 1 and 2 were the most effective insulin secretagogues among the anthocyanins and anthocyanidins tested at 4 and 10 mM glucose concentrations. Pelargonidin-3-galactoside is one of the major anthocyanins, and its aglycone, pelargonidin, caused a 1.4-fold increase in insulin secretion at 4 mM glucose concentration. The rest of the anthocyanins and anthocyanidins tested in our assay had only marginal effects on insulin at 4 and 10 mM glucose concentrations.
  • Article
    Anthocyanin composition in berries of Rhamnus alaternus L., a perennial wild shrub typical of the Mediterranean area, was determined for the first time. The pigments were extracted from the berries with 0.1% HCl in methanol and purified using a C-18 solid-phase cartridge. High-performance liquid chromatography diode array detection-mass spectrometry analysis showed that delphinidin 3-O-rutinoside represented about 62.4% of the total pigments. Other anthocyanins were 3-O-rutinoside derivatives of cyanidin (8.4%), petunidin (15.8%), pelargonidin (4.7%), and peonidin and malvidin (8.7%). The concomitant presence of the six most common anthocyanidins suggested that R. alaternus berries, besides being a good pigment source, could also be a useful tool for anthocyanin identification.
  • Article
    Anthocyanins, present in various fruits and vegetables as natural colorant, have been well characterized to be involved in various bioactive properties and are wildly used for their antioxidant properties. Furthermore, recent studies have revealed pleiotropic anticancer and antiproliferative capabilities of anthocyanin. Berry extract contains high amounts of anthocyanins and is commonly used in diet or in some therapeutic applications. In this study, we first observed that cyanidin 3-rutinoside and cyanidin 3-glucoside (extracted from Morus alba L.) exerted a dose-dependent inhibitory effect on the migration and invasion, of highly metastatic A549 human lung carcinoma cells in absence of cytotoxicity. The results showed that cyanidin 3-glucoside and cyanidin 3-rutinoside treatments could decrease the expressions of matrix matalloprotinase-2 (MMP-2) and urokinase-plasminogen activator (u-PA) in a dose-dependent manner and enhance the expression of tissue inhibitor of matrix matalloprotinase-2 (TIMP-2) and plasminogen activator inhibitor (PAI). Further analysis with semi-quantitative RT-PCR showed that these alterations were all on the transcriptional level. Further, a treatment of cyanidin 3-rutinoside and cyanidin 3-glucoside also resulted in an inhibition on the activation of c-Jun and NF-kappaB. Together, these result suggested that anthocyanins could decrease the in vitro invasiveness of cancer cells and therefore, may be of great value in developing a potential cancer therapy.
  • Article
    Consumption of fruits and berries has been associated with decreased risk of developing cancer. The most abundant flavonoid constituents of fruits and berries are anthocyans (i.e. anthocyanins, glycosides, and their aglycons, anthocyanidins) that cause intense colouration. In this review, we describe epidemiological evidence hinting at the cancer preventive activity of anthocyan-containing foods in humans, results of chemoprevention studies in rodent models with anthocyans or anthocyan-containing fruit/vegetable extracts, and pharmacological properties of anthocyans. Anthocyanidins have been shown to inhibit malignant cell survival and confound many oncogenic signalling events in the 10(-6)-10(-4) M concentration range. Studies of the pharmacokinetics of anthocyanins after their consumption as single agents, anthocyanin mixtures or berry extracts suggest that anthocyanins reach levels of 10(-8)-10(-7) M in human blood. It is unclear whether such concentrations are sufficient to explain anticarcinogenic effects, and whether anthocyanins exert chemopreventive efficacy themselves, or if they need to undergo hydrolysis to their aglyconic counterparts. The currently available literature provides tantalising hints of the potential usefulness of anthocyans or anthocyan mixtures as cancer chemopreventive interventions. Nevertheless further studies are necessary to help adjudge the propitiousness of their clinical development.
  • Article
    Anthocyanin composition in the berries of Laurus nobilis L., a perennial tree or shrub typical of the Mediterranean region, was determined for the first time. The pigments were extracted from the berries with 0.1% HCl in methanol, purified on a C-18 solid-phase cartridge, and characterized by means of high-performance liquid chromatography (HPLC)-diode array detection (DAD)-mass spectrometry (MS) analysis. The major anthocyanins were characterized as cyanidin 3-O-glucoside (41%) and cyanidin 3-O-rutinoside (53%). Furthermore, two minor anthocyanins were detected and identified as 3-O-glucoside and 3-O-rutinoside derivatives of peonidin (5%). The two major pigments were also isolated by preparative HPLC and characterized by H1 nuclear magnetic resonance (NMR) spectroscopy. The attractive color and the great abundance of the plant in the south of Italy make Laurus nobilis berries a new and very good source of natural pigments.
  • Article
    The stability of anthocyanins from red wine was assessed using an in vitro digestion system that simulated the physiochemical changes that occur in the upper gastrointestinal tract. Anthocyanins in red wine were stable to gastric conditions whereas there was a small loss in total phenol content. After pancreatic digestion, the total anthocyanins were very poorly recovered compared to the bulk phenols in the IN sample, which was previously described as the “serum-available” fraction, and the majority of the anthocyanins and phenols were recovered in the OUT fraction, previously described as the “colon-available” fraction. Removing alcohol from the wine samples prior to the procedure did not markedly affect this pattern.
  • Article
    The dicaffeoyl anthocyanin, phacelianin, was isolated from blue petals of Phacelia campanularia. Its structure was determined to be 3-O-(6-O-(4'-O-(6-O-(4'-O-beta-d-glucopyranosyl-(E)-caffeoyl)-beta-d-glucopyranosyl)-(E)-caffeoyl)-beta-d-glucopyranosyl)-5-O-(6-O-malonyl-beta-d-glucopyranosyl)delphinidin. The CD of the blue petals of the phacelia showed a strong negative Cotton effect and that of the suspension of the colored protoplasts was the same, indicating that the chromophores of phacelianin may stack intermolecularly in an anti-clockwise stacking manner in the blue-colored vacuoles. In a weakly acidic aqueous solution, phacelianin displayed the same blue color and negative Cotton effect in CD as those of the petals. However, blue-black colored precipitates gradually formed without metal ions. A very small amount of Al(3+) or Fe(3+) may be required to stabilize the blue solution. Phacelianin may take both an inter- and intramolecular stacking form and shows the blue petal color by molecular association and the co-existence of a small amount of metal ions. We also isolated a major anthocyanin from the blue petals of Evolvulus pilosus and revised the structure identical to phacelianin.
  • Article
    Anthocyanin pigments from a wide variety of edible and ornamental black, blue, pink, purple, red, and white wheat, barley, corn, rice, and wild rice were identified and quantified to evaluate their potential as natural colorants or functional food ingredients. The total anthocyanin contents varied significantly and exhibited a range of 7-3276 microg/g. Some grains, such as red rice and black rice, contained a limited number of pigments, whereas others, such as blue, pink, purple, and red corns, had complex anthocyanin profiles. Of the 42 anthocyanin compounds observed, 9 were characterized by comparison of the spectroscopic and chromatographic properties with those of authentic standards. The remaining compounds were tentatively identified on the basis of spectroscopic properties and electrospray ionization mass spectra. The most abundant anthocyanins were cyanidin 3-glucoside in black and red rices and in blue, purple, and red corns, pelargonidin 3-glucoside in pink corn, and delphinidin 3-glucoside in blue wheat.
  • Article
    Flavonols are products of the flavonoid biosynthetic pathway, which also give rise to anthocyanins and condensed tannins in grapes. We investigated their presence in the berry skins of 91 grape varieties (Vitis vinifera L.), in order to produce a classification based on the flavonol profile. The presence of laricitrin 3-O-galactoside and syringetin 3-O-galactoside in red grapes is reported here for the first time. In red grapes, the main flavonol was quercetin (mean = 43.99%), followed by myricetin (36.81%), kaempferol (6.43%), laricitrin (5.65%), isorhamnetin (3.89%), and syringetin (3.22%). In white grapes, the main flavonol was quercetin (mean = 81.35%), followed by kaempferol (16.91%) and isorhamnetin (1.74%). The delphinidin-like flavonols myricetin, laricitrin, and syringetin were missing in all white varieties, indicating that the enzyme flavonoid 3',5'-hydroxylase is not expressed in white grape varieties. The pattern of expression of flavonols and anthocyanins in red grapes was compared, in order to gain information on the substrate specificity of enzymes involved in flavonoid biosynthesis.
  • Article
    The major anthocyanins of boysenberry fruit, a cross between Rubus loganbaccus and Rubus baileyanus Britt., were isolated by preparative high-performance liquid chromatography (HPLC). The structures of cyanidin-3-[2-(glucosyl)glucoside] (1) and cyanidin-3-[2-(glucosyl)-6-(rhamnosyl)glucoside] (2) were determined by NMR in 1% DCOOD/D(2)O. An unusually high chemical shift (delta 2.5) is reported for H-5' '' of cyanidin-3-[2-(glucosyl)glucoside].