Soluble phenolics and antioxidant properties of soybean (Glycine max L.) cultivars with varying seed coat colours

This research was the first to investigate nutritional components, including soluble phenolics (isoflavones and anthocyanins), protein, oil, and fatty acid as well as antioxidant activities in different coloured seed coat soybeans (yellow, black, brown, and green) for two crop years. The soluble phenolics differed significantly with cultivars, crop years, and seed coat colours, while protein, oil, and fatty acid exhibited only slight variations. Especially, malonylgenistin and cyanidin-3-O-glucoside compositions had the most remarkable variations. Green soybeans had the highest average isoflavone content (3079.42 μg/g), followed by yellow (2393.41 μg/g), and black soybeans (2373.97 μg/g), with brown soybeans showing the lowest value (1821.82 μg/g). Anthocyanins showed only in black soybeans, with the average contents of the primary anthocyanins, cyanidin-3-O-glucoside, delphinidine-3-O-glucoside, and petunidin-3-O-glucoside, quantified at 11.046, 1.971, and 0.557 mg/g, respectively. Additionally, Nogchae of green soybean and Geomjeongkong 2 of black soybean may be recommended as potential cultivars owing to the highest average isoflavone (4411.10 μg/g) and anthocyanin (21.537 mg/g) contents. The scavenging activities of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals also differed remarkably, depending upon isoflavone and anthocyanin contents, with black soybeans exhibiting the highest antioxidant effects.     

Saskatoon berries (Amelanchier alnifolia Nutt.) scavenge free radicals and inhibit intracellular oxidation

Two cultivars (Thiessen and Smoky) of Saskatoon berries (Amelanchier alnifolia Nutt.) possess free radical scavenging activities in a concentration-dependent manner, whereas Thiessen presented higher (p < 0.05) activity compared to Smoky due to its relatively abundant anthocyanin content. Total anthocyanin content significantly corresponded to free radical scavenging activities (p < 0.05). Solvent fractionation revealed that the free radical scavenging components, i.e., anthocyanin, predominantly occurred in the ethyl acetate and n-butanol extracted fractions, suggesting that active components are more likely to occur in glycoside forms. HPLC further confirmed the existence of cyanidin-3-O-galactoside and cyanidin-3-O-glucoside as leading anthocyanins in the Saskatoon berries. Furthermore, Saskatoon berries extracts from both cultivars suppressed peroxy-radical induced intracellular oxidation in a concentration-dependent manner without affecting cell viability. The obtained results provided useful information for the future application of Saskatoon berries in the nutraceutical industry.     

Studies on the anthocyanin profile and biological properties from the fruits of Acanthopanax senticosus (Siberian Ginseng)

The anthocyanin profile and biological activities, including antioxidant, xanthine oxidase inhibitory, angiotensin converting enzyme (ACE) inhibitory, and anticancer of Acanthopanax senticosus fruits were evaluated for the first time. The acidified 80% methanol extract of this species exhibited high biological properties at a concentration of 60 μg/ml. Moreover, cyanidin-3-O-(2″-O-xylosyl)-glucoside was identified using C₁₈ column chromatography, NMR spectroscopy, and HPLC-DAD-ESI/MS analysis. This compound was present at 5.2 mg/g, representing approximately 91% of the total peak area and possessed strong antioxidant effects against DPPH, ABTS, and hydroxyl radicals (IC₅₀ of 85.2, 43.7, and 126.6 μg/ml, respectively). Cyanidin-3-O-(2″-O-xylosyl)-glucoside also exhibited significant inhibitory activities against xanthine oxidase and ACE (IC₅₀: 55.5 and 47.1 μg/ml, respectively). Especially, LNCap (prostate), MOLT-4F (leukaemia), and ACHN (renal) cell lines exhibited potent anticancer effects, with IC₅₀ of 5.2, 11.2, and 22.5 μg/ml, respectively, in comparison with other cancer cell lines. Therefore, A. senticosus fruit may be utilised as an effective source for food and nutraceutical uses due to its high anthocyanin content as well as various biological properties.     

Identification of anthocyanins isolated from black rice (Oryza sativa L.) and their degradation kinetics

Black rice is rich in anthocyanins-plant pigments. The aim of this work was to identify anthocyanins in black rice using high-performance liquid chromatography (HPLC)-electrospray ionization — mass spectrometry with diode array detection. Four different anthocyanins (cyanidin-3-glucoside, peonidin-3-glucoside, cyanidin-3,5-diglucoside, cyanidin-3-rutinoside) were identified in black rice. Thermal stability of the four anthocyanins in black rice extract was studied at selected temperatures (80 °C, 90 °C and 100 °C) in the range of pH 1.0–pH 6.0. The results indicated that the thermal degradation of anthocyanins followed the first-order reaction kinetics. The temperature-dependent degradation was adequately modeled on the Arrhenius equation. The calculated values of activation energies (Ea), t_1/2 and k were different for the four anthocyanins. The degradation rate of monomeric anthocyanin increased with increasing heating temperature and pH values. Especially, as heating temperature increasing to 100 °C and pH value to 5.0.     

Impact of various factors on the composition and stability of black currant anthocyanins

Nine black currant varieties cultivated in Lithuania were studied. The highest amount of ascorbic acid was established in fresh berries from cv Minaj Smyriov and Kupoliniai: these varieties contained 220.5 and 186.7 mg 100 g⁻¹ of ascorbic acid in berries. The highest amount of anthocyanins was found in cake produced from berries cv Kupoliniai and Kriviai: 14.65 and 15.42 mg g⁻¹, respectively. The major pigment determined in Kupoliniai variety was delphinidin-3-rutinoside; in Ben Lomond, Minaj Smyriov, Kriviai and Gagatai cultivars, cyanidin-3-rutinoside. The composition of the identified pigments was the following: cyanidin-3-rutinoside (33–38%), delphinidin-3-rutinoside (27–34%), cyanidin-3-glucoside (8–10%) and delphinidin-3-glucoside (8–10%). Impact of storage, thermal treatment and addition of sweeteners were studied. Cyanidin-3-rutinoside was the most stable to the effect of thermal treatment at 95 °C, while cyanidin and delphinidin rutinosides were the most stable during storage for 12 months at 8 °C. Fructose has a greater effect on anthocyanin degradation compared with glucose and aspartame.     

Furostanol saponins in Allium caepa L. Var. tropeana seeds

An analysis of the polar extracts from seeds of Allium caepa L. var. tropeana led to the isolation of eight furostanol saponins, one of which was previously reported in the literature. On the basis of 1D, 2D NMR and mass spectrometry data, the structures of the compounds were elucidated as 1-O-β-D-glucopyranosyl-(25R)-furost-5(6)-en-1β,3β,22α,26-tetraol-26-O-α-L-rhamnopyranosyl-(1‴ → 2″)-O-α-L-arabinopyranoside (1a), its epimer at position 22, 1-O-β-D-glucopyranosyl-(25R)-furost-5(6)-en-1β,3β,22β,26-tetraol-26-O-α-L-rhamnopyranosyl-(1‴ → 2″)-O-α-L-arabinopyranoside (1b), 1-O-β-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-1β,3β,22ξ,26-tetraol-26-O-α-L-rhamnopyranosyl-(1‴ → 2″)-O-α-L-arabinopyranoside (probably artefact) (2), 1-O-β-D-glucopyranosyl-(25R)-furost-5(6)-en-1β,3β,22β,26-tetraol-26-O-α-L-rhamnopyranosyl-(1‴ → 6″)-O-β-D-galactopyranoside (3), 1-O-β-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-1β,3β,22ξ,26-tetraol-26-O-α-L-rhamnopyranosyl-(1‴ → 6″)-O-β-D-galactopyranoside (probably artefact) (4), 26-O-β-D-glucopyranosyl-(25R)-furost-5(6)-en-3β,22α,26-triol-3-O-α-L-rhamnopyranosyl-(1″ → 2′)-O-[β-D-glucopyranosyl-(1‴ → 6′)-O]-β-D-glucopyranoside (5a) and its epimer at position 22,26-O-β-D-glucopyranosyl-(25R)-furost-5(6)-en-3β,22β,26-triol-3-O-α-L-rhamnopyranosyl-(1″ → 2′)-O-[β-D-glucopyranosyl-(1‴ → 6′)-O]-β-D-glucopyranoside (5b) and the known compound 26-O-β-D-glucopyranosyl-22-O-methyl-(25R)-furost-5(6)-en-3β,22ξ,26-triol-3-O-α-L-rhamnopyranosyl-(1″ → 2′)-O-[β-D-glucopyranosyl-(1‴ → 6′)-O]-β-D-glucopyranoside (6) [Mimaki, Y., Satou, T., Kuroda, M., Sashida, Y., & Hatakeyama, Y. (1999). Steroidal saponins from the bulbs of Lilium candidum. Phytochemistry, 51, 567–573]. This is the first report on furostanol saponins in the seeds of Allium caepa L. var. tropeana.     

Anthocyanin and phenolic characterization,chemical composition and antioxidant activity of chagalapoli (Ardisia compressa K.) fruit: A tropical source of natural pigments

Chagalapoli (Ardisia compressa K.) is a tropical fruit of deep purple color with a high content of pigments. Anthocyanins, polyphenol composition, antioxidant activity and physicochemical characteristics of chagalapoli fruits (CF) are analyzed. The proximal and mineral composition is similar to that found in common berries (strawberry, blackberry and blueberry). A high content of total phenolics (1051.3 ± 43.5 mg of gallic acid equivalents/100 g of FW) is present, among which anthocyanins predominated (796.0 ± 2.3 mg of cyanidin 3-O-glucoside equivalents/100 g FW). Twelve anthocyanins were separated and ten of them identified by HPLC–DAD–MS. The main anthocyanins were malvidin-3-O-galactoside (35%), delphinidin 3-O-galactoside (28%) and petunidin 3-O-galactoside (19%). Other polyphenols identified included: flavonols, flavan-3-ols (catechin and proantocyanidin dimers) and hydroxycinnamoyl derivatives. The antioxidant activity of CF was 40% higher than that found in common berries, which were simultaneously analyzed. The high content of anthocyanins in CF and its peculiar anthocyanin profile make this under-utilized fruit a promising source of pigments and phenolic nutraceuticals.     

Identification and characterisation of anthocyanins in the antioxidant activity-containing fraction of Liriope platyphylla fruits

The objective of this study was to investigate antioxidant activities and anthocyanin profiles in the fruits of Liriope platyphylla, where these are considered functional substances in Korea. The acidic methanol extract of this species exhibited potent antioxidant activities, showing 83.9% DPPH scavenging activity and 92.5% ABTS scavenging activity at a concentration of 0.5 mg/ml. Moreover, anthocyanins were identified by reversed-phase C₁₈ column chromatography, NMR spectroscopy, and HPLC-DAD-ESI/MS analysis. Seven anthocyanins were characterised, including delphinidin-3-O-glucoside (1), delphinidin-3-O-rutinoside (2), cyanidin-3-O-glucoside (3), petunidin-3-O-glucoside (4), petunidin-3-O-rutinoside (5), malvidin-3-O-glucoside (6), and malvidin-3-O-rutinoside (7). Among these, petunidin-3-O-rutinoside (5) (7302.2 μg/g) and malvidin-3-O-rutinoside (7) (5776.1 μg/g) were the predominant anthocyanins, whereas the least prevalent anthocyanin was found to be cyanidin-3-O-glucoside (3) (64.9 μg/g). Therefore, our results suggest that strong antioxidant activities of the acidic methanol extract of L. platyphylla fruits are correlated with high anthocyanin contents, particularly the petunidin-3-O-rutinoside (5) and malvidin-3-O-rutinoside (7).     

Identification and quantification of phenolic acids and flavonol glycosides in Tunisian Morus species by HPLC-DAD and HPLC–MS

The total polyphenol and flavonoids in leaves of Morus alba var. alba, Morus alba var. rosa and Morus rubra were determined and identification of their components was carried out. The total content of phenolics varied between 345.20 and 631.53 mg gallic acid equivalents (GAE)/100 g dry weight (DW) basis. The total amount of flavonoids ranged between 193.87 and 398.33 mg rutin equivalents (RE)/100 g DW. Thirteen compounds were isolated by chromatography, and their structures determined to be mainly flavonol glycosides and phenolic acids. Three novel components were identified as kaempferol-7-O-glucoside, quercetin-3-O-β-glucoside-7-O-α-rhamnoside and quercetin-3-O-rhamnoside-7-O-glucoside, for the first time from mulberry leaves. Others known compounds were also identified.     

Factors controlling flavors binding constants to cyclodextrins and their applications in foods

The binding constants of 14 different flavors (Maltol, Furaneol, Vanillin, Methyl Cinnamate, Cineole, Citral, Menthol, Geraniol, Camphor, Nootkatone, Eugenol, p-vinil Guayacol and Limonene) to cyclodextrins (α-cyclodextrin and β-cyclodextrin) have been determined by an UV–Vis spectrophotometric technique. In all cases the binding constant of flavors to β-cyclodextrin are bigger than the corresponding one to α-cyclodextrin. This fact is due to the different size of cyclodextrin cavity. As well as, a relationship between log P of each flavor and the binding constants was found, proving that the driving force for host–guest complex formation is hydrophobic/hydrophilic interactions.     

Lingonberry (Vaccinium vitis-idaea L.) grown in the Pacific Northwest of North America: Anthocyanin and free amino acid composition

Lingonberries and their products are popular and generally accessible in Europe, though in the US they are uncommon and considered a minor berry/fruit crop. The on-going interest in potential health benefits from berry consumption has heightened interest in broadening the selection of berry/fruit crops in the US. This study measured total phenolics, total tannins, complete anthocyanin content, and total (and individual) free amino acid composition for each of five lingonberry cultivars. Cultivars Ida, Koralle, Linnea, Sanna, and Sussi were grown in Oregon, USA, and had only been evaluated previously for their horticultural traits. All five cultivars contained the three anticipated anthocyanins (by HPLC): cyanidin-3-galactoside (main anthocyanin found in these berries), cyanidin-3-glucoside, and cyanidin-3-arabinoside. These lingonberries’ total anthocyanin content ranged from 27.4 (‘Linnea’) to 52.6 (‘Ida’) mg/100 g fw. They contained 22 free amino acids (FFAs) and total FAAs ranged from 28.92 (‘Sanna’) to 70.38 (‘Koralle’) mg/100 g fw. Asparagine (ASN) was the leading FAA (22–34% of the total FAAs) for all five cultivars. This is the first report on lingonberry FAA content.     

Characterisation of phenolic phytochemicals and quality changes related to the harvest times from the leaves of Korean purple perilla (Perilla frutescens)

The objective of this study was to investigate the profiles of phenolic phytochemicals in the leaves of Korean purple perilla (cv. Bora, Perilla fructescens) using reversed-phase C₁₈ column chromatography and HPLC with DAD-ESI/MS analysis. Changes in their contents were also the first reported through eight different harvest times during two months. They were characterised as five anthocyanins and three phenolic acids including cyanidin-3,5-di-O-glucoside (1), cyanidin-3-O-glucoside (2), cyanidin-3-O-(6-O-caffeoyl)glucoside-5-O-glucoside (3), cyanidin-3-O-(6-O-coumaroyl)glucoside-5-O-glucoside (4), cyanidin-3-O-(6-O-coumaroyl)glucoside (5), caffeic acid (6), rosmarinic acid (7), and rosmarinic acid methylester (8). Significant differences were observed between individual and total phytochemical contents, especially, cyanidin-3-O-(6-O-coumaroyl)glucoside-5-O-glucoside (4) and rosmarinic acid (7) exhibited the predominant constituents. Among different harvest times, the highest content was found with 82.473 mg/g on 21st September, while the lowest was 39.000 mg/g on 17th August. These results may be useful in determining the optimal harvest time at which phenolic phytochemicals reaches a maximum level in mid-September.     

Phytochemical,antioxidant and pigment stability of açai (Euterpe oleracea Mart.) as affected by clarification,ascorbic acid fortification and storage

Açai juice at two clarity stages (semi-clarified and clarified) was compared to 100% açai pulp following ascorbic acid fortification to evaluate phytochemical and antioxidant changes during storage at 4 and 20 °C. Cyanidin-3-rutinoside (202 ± 5.8 mg/L) and cyanidin-3-glucoside (75 ± 4.8 mg/L) were the predominant anthocyanins in açai while 11 non-anthocyanin polyphenolics were detected in concentrations from 1.1 to 55 mg/L of açai pulp. Clarification of açai pulp resulted in a 27% loss in total polyphenolics (197 ± 6.9 mg gallic acid/100 mL) and in a 20% reduction in both total anthocyanins (729 ± 3.4 mg/L) and antioxidant capacity (54 ± 1.7 μmol Trolox equivalents/mL). Anthocyanin degradation followed first order kinetics, with half-lives ranging from 9.4 to 43 days for cyanidin-3-glucoside and from 18 to 82 days for cyanidin-3-rutinoside. Fortification with ascorbic acid accelerated anthocyanin degradation in clarified juice at both storage temperatures, likely due to the loss of polymeric anthocyanin forms (21%) during clarification. Although clarification enhanced the amount of monomeric anthocyanins present in açai juice which relates positively to the aesthetic quality, processing and handling regimes must be optimized to achieve maximum retention of their functional properties during storage.     

Elucidation of structural difference in theaflavins for modulation of starch digestion

The relationship between structure and activity of theaflavins against human pancreatic α-Amylase was investigated by in vitro and in silico methods. The IC₅₀ and total energy value showed that inhibitory effects followed the order: theaflavin-3, 3’-di-O-gallate > theaflavin-3’-O-gallate > theaflavin-3-O-gallate > theaflavin. Inhibitory activity was depended on hydroxyl groups and galloyl moieties of theaflavins to interact with the catalytic residues of the active site of α-Amylase by hydrogen bonds and π–π (aromatic–aromatic) interactions. The galloylated theaflavin has higher binding affinity with α-Amylase than non-galloylated theaflavin. The study showed that theaflavins might act as natural enzyme inhibitors with potential health benefits, which provide a foundation for designing novel functional food for effective controlling of starch digestion and postprandial glucose levels.     

Anthocyanin profile of mayhaw (Cretaegus opaca)

Mayhaw samples (Elite 2001, Texas Star 2000 and 1999) were harvested over a three-year period and analyzed for anthocyanin concentration, colour density, polymeric colour, and % polymeric compounds. Anthocyanins were separated by HPLC. All mayhaw samples from the three year period contained about 50% of cyanidin-3-glucoside, 10–21% cyanidin-3-galactoside, and less than 32% unidentified anthocyanins. The highest concentration of anthocyanins was detected in the Texas Star 1999 sample (about 7 mg/100 g) whereas Texas 2000 and Elite 2001 had 3.3 and 2.3 mg/100 g of anthocyanins, respectively. Colour density was lower in the Elite samples than the Texas. The polymeric anthocyanins and polymeric colour decreased in the Elite 2001 > Texas Star 2000 > Texas Star 1999 and the decrease was tentatively ascribed to sample age.     

Taste modification of amino acids and protein hydrolysate by α-cyclodextrin

The objective of this work was to characterize the formation of amino acid inclusion complexes with α-cyclodextrin (α-CD) and evaluate the influence of added α-CD on the taste perception of amino acids and hydrolyzed soy protein at pH 4.5. The formation of the inclusion complexes of phenylalanine, tryptophane, tyrosine, isoleucine, proline and histidine with α-CD were detected by nuclear magnetic resonance techniques (ROESY and DOSY) and the sensory characteristics of soy hydrolysates were judged by a panel of trained tasters. It was concluded that these amino acids form inclusion complexes with α-CD and the order of affinity for the α-CD cavity is phenylalanine ≈ tryptophane > proline > isoleucine ≈ tyrosine ≈ histidine. α-CD alters the bitter taste perception of the amino acids and reduces the bitter taste from hydrolyzed soy protein. These results indicate a potential use of α-CD for debittering protein hydrolysates in acidic beverages.     

Cyanidin-3-glucoside,nutritionally important constituents and in vitro antioxidant activities of Santalum album L. berries

Anthocyanins are ubiquitous plant pigments. They are hydrophilic, and have high tinctorial value hence, used as natural food colorant. The main aim of this study was characterization of Santalum album L. berries for its pigment content, nutritionally important phytoconstituents and functional attributes. Major pigment identified was cyanidin-3-glucoside (0.21% FW) as confirmed by spectral characteristics including LC–MS. Nutrients such as total carbohydrates (8.5), proteins (5.8), free amino acids (0.8 g), oil (1.5 g), ascorbic acid (1.5 μg), tocopherols (0.3 mg) and niacin (5.2 mg) per 100 g berries were determined along with total soluble solids (13.4°Brix) and phenols (3.1 mg GAE/g). Reducing power and DPPH· scavenging assays showed highest activity in methanol extract, which also efficiently protected bleaching of β-carotene (EC₅₀ 285 μg/mL) in β-carotene–linoleate model. Pigment rich crude extract was not toxic to HepG2 cells during 24 h exposure, whereas cyanidin-3-glucoside was cytotoxic (IC₅₀ 0.1 μg/mL).     

Influence of Dekkera bruxellensis on the contents of anthocyanins,organic acids and volatile phenols of Dão red wine

The anthocyanin, organic acid and volatile phenol compositions of red wine obtained from Touriga Nacional grapes growing in the Dão region (Portugal) were determined by HPLC/DAD, HPLC/UV and GC/FID, respectively. By these means, nine anthocyanic compounds (malvidin-3,5-O-diglucoside, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, peonidin-3-O-glucoside, malvidin-3-O-glucoside, delphinidin, cyanidin, pelargonidin and malvidin), six organic acids (ketoglutaric, tartaric, malic, quinic, lactic and shikimic acids) and two volatile phenols (4-ethylguaiacol and 4-ethylphenol) were identified and quantified. Malvidin-3-O-glucoside, the pair lactic plus shikimic acids and 4-ethylguaiacol were the main anthocyanin, organic acids and volatile phenol, respectively. The effects of nine different Dekkera bruxellensis strains on these chemical parameters were also evaluated. The results obtained indicate that some strains of D. bruxellensis yeast are able to cause deterioration of red wine from the Dão region during its maturation by the production of volatile phenols, namely 4-ethylphenol.     

Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis

The aim of this study was to isolate and identify the anthocyanins in the black seed coated soybean (cv. Cheongja 3, Glycine max (L.) Merr.) using reverse phase C-18 open column chromatography and high-performance liquid chromatography (HPLC) with diode array detection and electro spray ionization/mass spectrometry (DAD-ESI/MS) analysis, respectively. Anthocyanins were extracted from the coat of black soybeans with 1% TFA in methanol, isolated by RP-C-18 column chromatography, and their structures elucidated by 1D and 2D NMR spectroscopy. The isolated anthocyanins were characterised as delphinidin-3-O-glucoside (3), cyanidin-3-O-glucoside (5), petunidin-3-O-glucoside (6), pelargonidin-3-O-glucoside (7) and cyanidin (9). Furthermore, four minor anthocyanins were detected and identified as catechin-cyanidin-3-O-glucoside (1), delphinidin-3-O-galactoside (2), cyanidin-3-O-galactoside (4), and peonidin-3-O-glucoside (8) based on the fragmentation patterns of HPLC-DAD-ESI/MS analysis.     

Characterization of in vitro anthocyanin-producing sour cherry (Prunus cerasus L.) callus cultures

Anthocyanin-producing callus cultures from in vitro sour cherry (Prunus cerasus L.) leaf tissues were established. As in the parent leaf tissues, the calli extracts showed the synthesis of a prevalent anthocyanin, cyanidin 3-glucoside. When the dark grown callus cultures were exposed to the light, cyanidin 3-glucoside content was increased from 0.1 to 4.5 mg 100 g⁻¹ fresh weight. Thus, of the available strategies for the enhancement of pigment production light resulted the triggering factor in this cell system. The addition of 50 μM jasmonic acid to the culture medium stimulated cyanidin 3-glucoside synthesis which resulted in an earlier appearance of pigment on the calli.