effect of dose size on bioavailability of acylated and nonacylated anthocyanins from red cabbage (Brassica oleracea L. Var. capitata)

Recent studies indicate that anthocyanin intake conveys a variety of health benefits, which depend on absorption and metabolic mechanisms that deliver anthocyanins and their bioactive metabolites to responsive tissues. The anthocyanin bioavailability of red cabbage (Brassica oleracea L. var. capitata) was evaluated as reflected by urinary excretion of anthocyanins and anthocyanin metabolites. Twelve volunteers consumed 100, 200, and 300 g of steamed red cabbage (containing 1.38 micromol of anthocyanins/g of cabbage) in a crossover design. Anthocyanin concentration in cabbage extract and urine was measured by HPLC-MS/MS. Six nonacylated and 30 acylated anthocyanins were detected in red cabbage, and 3 nonacylated anthocyanins, 8 acylated anthocyanins, and 4 metabolites were present in urine. Mean 24 h excretion of intact anthocyanins increased linearly from 45 (100 g dose) to 65 nmol (300 g dose) for acylated anthocyanins and from 52 (100 g dose) to 79 nmol (300 g dose) for nonacylated anthocyanins. Urinary recovery of intact anthocyanins (percent of anthocyanin intake) decreased linearly from 0.041% (100 g dose) to 0.020% (300 g dose) for acylated anthocyanins and from 0.18% (100 g dose) to 0.09% (300 g dose) for nonacylated anthocyanins. Anthocyanin metabolites consisted of glucuronidated and methylated anthocyanins. The results show that red cabbage anthocyanins were excreted in both intact and metabolized forms and that recovery of nonacylated anthocyanins in urine was >4-fold that of acylated anthocyanins.     

Structure-function relationships of anthocyanins from various anthocyanin-rich extracts on the inhibition of colon cancer cell growth

Anthocyanins are potent antioxidants and may be chemoprotective. However, the structure-function relationships are not well understood. The objectives of this study were to compare the chemoprotective properties of anthocyanin-rich extracts (AREs) with variable anthocyanin profiles to understand the relationship between anthocyanin chemical structure and chemoprotective activity, measured as inhibition of colon cancer cell proliferation. Additionally, the chemoprotective interaction of anthocyanins and other phenolics was investigated. AREs with different anthocyanin profiles from purple corn, chokeberry, bilberry, purple carrot, grape, radish, and elderberry were tested for growth inhibition (GI 50) using a human colorectal adenocarcinoma (HT29) cell line. All AREs suppressed HT29 cell growth to various degrees as follows: purple corn (GI 50 approximately 14 microg of cy-3-glu equiv/mL) > chokeberry and bilberry > purple carrot and grape > radish and elderberry (GI 50 > 100 microg of cy-3-glu equiv/mL). Anthocyanins played a major role in AREs' chemoprotection and exerted an additive interaction with the other phenolics present. Statistical analyses suggested that anthocyanin chemical structure affected chemoprotection, with nonacylated monoglycosylated anthocyanins having greater inhibitory effect on HT-29 cell proliferation, whereas anthocyanins with pelargonidin, triglycoside, and/or acylation with cinnamic acid exerted the least effect. These findings should be considered for crop selection and the development of anthocyanin-rich functional foods.     

Gastrointestinal uptake of nasunin, acylated anthocyanin in eggplant

We previously showed that nasunin, acylated anthocyanins in eggplant peel, comprises two isomers, cis-nasunin and trans-nasunin. In this study, gastrointestinal absorption of cis- and trans-nasunins was studied in rats. Orally administered nasunins were quickly absorbed in their original acylated forms and maximally appeared in blood plasma after 15 min. When the maximum plasma concentration and area under the plasma concentration curve were normalized by orally administered dose (micromoles per kilogram), there was no significant difference in the uptake efficiency between two isomers and both exhibited a plasma level almost identical to that of delphinidin 3-O-beta-D-glucopyranoside. However, metabolites such as 4'-O-methyl analogues and extended glucuronides which were observed for delphinidin 3-O-beta-D-glucopyranoside and cyanidin 3-O-beta-D-glucopyranoside metabolisms were not detected in urine or blood plasma. Moreover, deacylated and glycolytic products of nasunins such as delphinidin 3-O-beta-D-glucopyranoside or delphinidin (aglycone) were also not detected in blood plasma even after oral administration for 8 h. These results indicated that nasunins were absorbed in their original acylated forms and exhibit a bioavailability almost identical to that of nonacylated anthocyanins.     

Effect of storage temperature on the stability of anthocyanins of a fermented black carrot (Daucus carota var. L.) beverage: shalgam

The effect of temperature on the stability of shalgam anthocyanins stored at 4, 25, and 40 degrees C for 90 days was investigated. The effect of pasteurization and sorbate addition on the anthocyanin stability as compared to control was also studied. The monomeric anthocyanin content and color density decreased with increasing time as a function of storage temperature whereas the percent polymeric color and browning increased. The same trends were observed in control, pasteurized, and sorbate-added shalgam samples. Shalgam anthocyanins consisted of two nonacylated and three acylated cyanidin derivatives. Acylated anthocyanins were more stable when compared to nonacylated ones at all storage temperatures. The activation energies, 11.11-11.64 kcal/mol, were calculated from the reaction rate constants evaluated taking first-order reaction kinetics. The highest anthocyanin retention was observed at 4 degrees C storage temperature with a half-life between 231 and 239 days.     

Anthocyanins present in selected tropical fruits: acerola, jambolão, jussara, and guajiru

Many tropical fruits are rich in anthocyanins, though limited information is available about the characterization and quantification of these anthocyanins. The identification and quantification of anthocyanin pigments in four tropical fruits were determined by HPLC-MS/MS. Fruits studied included acerola (Malphigia emarginata), jussara (Euterpe edulis), jambol?o (Syzygium cumini), and guajiru (Chrysobalanus icaco). All four fruits were found to contain anthocyanin pigments. Anthocyanidin backbones included cyanidin, delphinidin, peonidin, pelargonidin, petunidin, and malvidin. Guajiru contained several acylated forms, while acerola, jussara, and jambol?o contained only nonacylated glycosides. These results demonstrate that these tropical fruits are rich in anthocyanins and that the anthocyanins are widely ranging in anthocyanidin backbone, glycosylation, and acylation.     

Calf thymus DNA-binding ability study of anthocyanins from purple sweet potatoes ( Ipomoea batatas L.)

A total of 10 anthocyanin compounds were identified from five purple sweet potato ( Ipomoea batatas L.) varieties, Qunzi, Zishu038, Ji18, Jingshu6, and Ziluolan, by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) to assess their calf thymus DNA-binding ability in vitro. The interaction between anthocyanins and calf thymus DNA in Tris-HCl buffer solution (pH 6.9) was evaluated by fluorescence spectroscopy. Using ethidium bromide (EB) as a fluorescence probe, fluorescence quenching of the emission peak was seen in the DNA-EB system when anthocyanins were added, indicating that the anthocyanins bound with DNA. The acylated groups influenced the ability of the interaction with DNA. Anthocyanins from purple sweet potato with more acylated groups in sorphorose have a stronger binding ability with DNA.     

Profiling of hydroxycinnamoyl tartrates and acylated anthocyanins in the skin of 34 Vitis vinifera genotypes

The diversity of berry skin flavonoids in grape genotypes has been previously widely investigated with regard to major compounds (nonacylated anthocyanins and flavonols), but much less with regard to acylated anthocyanins and hydroxycinnamoyl tartrates (HCTs). In this study, the composition of the phenolic fraction of the berry skin (free and acylated anthocyanins, flavonols, and HCTs) was assessed on 34 grapevine genotypes grown in a collection vineyard in northwestern Italy. The phenolic fraction was profiled on berries collected in the same vineyard, at the same ripening level across two successive vintages. The anthocyanin, HCT, and flavonol profiles were specific of each genotype, and the first two were relatively little affected by the vintage. A wide diversity in the polyphenolic fraction was shown among cultivars. Besides expected discriminatory effects of free anthocyanins and flavonol profiles, principal component analyses allowed a good discrimination of cultivars on the basis of coumaroylated anthocyanins and of the HCT profile. Anthocyanins were mostly acylated by aromatic acids, and acylation was independent from the anthocyanin substrate. HCTs were present mostly as coumaroyl and caffeoyl derivatives, and no correlation was observed between the same acylation patterns of tartrate and of anthocyanins. The results of this study are discussed in the light of new hypotheses on still unknown biosynthetic steps of phenolic substances and of the potential use of these substances in discrimination and identification of different grape cultivars in wines.     

Compositional Differences in Anthocyanins from Blue‐ and Purple‐Grained Spring Wheat Grown in Four Environments in Central Saskatchewan

Anthocyanins are important dietary components that play significant roles in human health because of their antioxidant and anti‐inflammatory properties. In the present study nine anthocyanin‐pigmented spring wheat lines grown at two sites in central Saskatchewan, Canada, were evaluated in terms of anthocyanin composition in comparison with four wheat checks over a two‐year period. The genotypes studied were blue‐aleurone and purple‐pericarp wheat. The anthocyanin pigments were quantified and identified with liquid chromatography and mass spectrometry. Two anthocyanin profiles were identified in the breeding lines, namely, blue profile and purple profile. Wheat lines with a purple profile had overall higher anthocyanin concentrations and more pigments than the blue‐aleurone lines. The purple profile was also characterized by the presence of acylated anthocyanins containing malonyl and succinyl substituents, but no acylated pigments were found in the blue profile. Delphinidin was the dominant aglycone in the blue profile, whereas cyanidin was the principal anthocyanidin in the purple profile. Genotype and interactions among genotype, year, and location were found to significantly influence content and composition of anthocyanin pigments. These differences in anthocyanin content and composition reflect various color characteristics and bioactivity for purple or blue wheat when utilized.     

Direct absorption of acylated anthocyanin in purple-fleshed sweet potato into rats

Absorption of acylated anthocyanins in purple-fleshed sweet potato (Ipomoea batatas cv. Ayamurasaki) in rats was studied to obtain evidence that the acylated anthocyanins themselves could exert a physiological function in vivo. Peonidin 3-caffeoylsophoroside-5-glucoside (Pn 3-Caf*sop-5-glc) in purple-fleshed sweet potato was directly absorbed into rat and present as an intact acylated form in plasma. After oral administration of the purple-fleshed sweet potato anthocyanin (PSA) concentrate containing 38.9 micromol of Pn 3-Caf*sop-5-glc/kg of body weight, Pn 3-Caf*sop-5-glc was detected in the plasma, and the C(max) value and t(max) were estimated as 50.0 +/- 6.8 nmol/Lof plasma and 30 min, respectively. Furthermore, the plasma antioxidant capacity was significantly elevated from 58.0 +/- 12.0 to 89.2 +/- 6.8 micromol of Trolox equivalent/L of plasma 30 min after the administration of the PSA concentrate.     

Bioavailability and tissue distribution of anthocyanins in bilberry (Vaccinium myrtillus L.) extract in rats

To clarify how structural diversity of anthocyanins relates to their in vivo function, bioavailability was precisely studied in rats using bilberry (Vaccinium myrtillus L.) extract (Bilberon 25) as an anthocyanin source that contains 15 different anthocyanins. The bilberry extract was orally or intravenously administered to rats, and the plasma levels of each anthocyanin were determined by high-performance liquid chromatography. As the result, all anthocyanins except peonidin 3-O-alpha-L-arabinoside were detectable in the blood plasma. The plasma concentration of anthocyanins as a whole reached the maximum level of 1.2 microM at 15 min after oral administration of 400 mg/kg bilberry extract (153.2 mg/kg as anthocyanins) and then decreased with time. Uptake and decay profiles of each anthocyanin in the plasma were almost the same for all anthocyanins except a few with their maximum after 30 min. Among the anthocyanins carrying the same aglycone, the plasma level after 15 min of oral administration was as follows: galactoside > glucoside > arabinoside. Plasma clearance of anthocyanins after intravenous administration clearly showed that arabinoside disappeared more rapidly than glucoside and galactoside. On the other hand, when anthocyanins carrying the same sugar moiety were compared, the half disappearance time of plasma anthocyanins was in the following order: delphinidin > cyanidin > petunidin = peonidin > malvidin. The bioavailability of anthocyanins was in the range of 0.61-1.82% and was 0.93% as the anthocyanin mixture. The bioavailability of anthocyanins carrying the same aglycone was in the following order: Galactoside showed the highest followed by glucoside and arabinoside for cyanidin and delphinidin, but arabinoside and galactoside showed a higher bioavailability than glucoside for petunidin and malvidin. Anthocyanins recovered in urine and bile during the first 4 h after intravenous administration were only 30.8 and 13.4%, respectively. Anthocyanin profiles in tissues were quite different from those in blood plasma. The major anthocyanins distributed in liver and kidney were the O-methyl anthocyanins such as peonidin, malvidin, and other O-methyl anthocyanins derived from delphinidin, cyanidin, and petunidin-glycosides.     

Effects of growing conditions on purple corncob (Zea mays L.) anthocyanins

Purple corn ( Zea mays L.) has been used for centuries as a natural food colorant in South America and, more recently, in Asia and Europe. However, limited information is available on the factors affecting their anthocyanin concentration and profiles. In this study, 18 purple corn samples grown under different conditions in Peru were evaluated for quantitative and qualitative anthocyanin composition as well as total phenolics. High variability was observed on monomeric anthocyanin and phenolic contents with yields ranging from 290 to 1333 mg/100 g dry weight (DW) and from 950 to 3516 mg/100 g DW, respectively, while 30.5-47.1% of the total phenolics were anthocyanins. The major anthocyanins present were cyanidin-3-glucoside, pelargonidin-3-glucoside, peonidin-3-glucoside, cyanidin-3-maloylglucoside, pelargonidin-3-maloylglucoside, and peonidin-3-maloylglucoside, and 35.6-54.0% of the anthocyanins were acylated. Potassium sources/concentrations on the soil and seedling density did not significantly affect anthocyanin composition. The growing location affected anthocyanin levels and the percentage of anthocyanins to total phenolics ( p < 0.01) and should be taken into account when choosing a material for color production.     

Comparison of volatiles, phenolics, sugars, antioxidant vitamins, and sensory quality of different colored carrot varieties

Four different colored carrots, orange, purple with orange core, yellow, and white, were examined for their content of phenolics, antioxidant vitamins, and sugars as well as their volatiles and sensory responses. A total of 35 volatiles were identified in all carrots, 27 positively. White carrot contained the highest content of volatiles, followed by orange, purple, and yellow. In total, 11, 16, 10, and 9 phenolic compounds were determined for the first time in orange, purple, yellow, and white carrots, respectively. Of these, chlorogenic acid was the most predominant phenolic compound in all carrot varieties. Differences (p < 0.05) in relative sweetness, the contents of vitamin C and alpha- and beta-carotenes, and certain flavor characteristics were observed among the colored carrot varieties examined. Purple carrots contained 2.2 and 2.3 times more alpha- and beta-carotenes (trace in yellow; not detected in white) than orange carrots, respectively. Purple carrot may be used in place of other carrot varieties to take advantage of its nutraceutical components.     

Particle size reduction leading to cell wall rupture is more important for the β-carotene bioaccessibility of raw compared to thermally processed carrots

The amount of nutrients that can be released from food products (i.e., nutrient in vitro bioaccessibility) is often studied as it is a starting point for investigating nutrient bioavailability, an indicator for the nutritional value of food products. However, the importance of mastication as a particle size reduction technique is poorly understood and is often neglected during in vitro procedures determining bioaccessibility. Therefore, the aim of the present work was to study the effect of mechanical breakdown on the β-carotene bioaccessibility of carrot samples, having different textural/structural characteristics (as a result of thermal processing). In the first part of this study, the all-E-β-carotene bioaccessibility of carrot particles of different sizes (ranging from cell fragments up to large cell clusters), generated from raw as well as from gently and intensely cooked carrot samples, was determined. In the second part of the study, the effect of human mastication on the particle size reduction of raw as well as of gently and intensely cooked carrot samples was investigated in order to allow identification and validation of a technique that could mimic mastication during in vitro procedures. Results showed a strong dependency of the all-E-β-carotene bioaccessibility on the particle size for raw and gently cooked carrots. After intense cooking, on the other hand, a considerable amount of all-E-β-carotene could be released from cell fragments (smaller than a cell) as well as from small and large cell clusters. Hence, the importance of mechanical breakdown, and thus also of (in vitro) mastication, is dependent on the carrot sample that is considered (i.e., the extent to which the carrot sample has been thermally processed prior to the particle size reduction). Structural changes occurring during mechanical and thermal processing are hereby key factors determining the all-E-β-carotene bioaccessibility. The average particle size distribution curves of raw and cooked carrots, which were chewed by 15 persons, could be mimicked by mixing 50 g of carrots using a Grindomix (Retsch) at 2500 rpm during 5 s. Based on this scientific knowledge, the identified in vitro mastication technique was successfully integrated in the in vitro digestion procedure determining the all-E-β-carotene bioaccessibility of carrot samples.     

Relationship between phenolic compounds, anthocyanins content and antioxidant activity in colored barley germplasm

Barley and its products are good sources of antioxidants. This experiment was conducted to examine the classification and concentration of phenolic compounds, proanthocyanidins, and anthocyanins in 127 lines of colored barley. Their relationship with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity was also examined. Barley was placed into seven groups using the colorimeter: hulled (black 1, black 2, black 3, and purple) and unhulled (black, blue, and purple). The contents of phenolic compounds and anthocyanins were analyzed by using HPLC. The average content of phenolic compounds in unhulled barley groups (268.6 microg/g) was higher than that in hulled (207.0 microg/g) (P > 0.05). The proanthocyanidins content was determined by modified vanillin assay. The average content of proanthocyanidins was significantly higher in purple and blue barley groups compared with black (P < 0.05). The content of anthocyanins varied from 13.0 to 1037.8 microg/g. Purple and blue barley groups contained higher average contents of anthocyanins than black (P < 0.05). The most common anthocyanin in the purple barley groups was cyanidin 3-glucoside, whereas delphinidin 3-glucoside was the most abundant anthocyanin in the blue and black groups. In colored barley, DPPH radical scavenging activity had high positive correlation to the content of phenolic compounds and proanthocyanidins.     

Potential chemopreventive properties of anthocyanin-rich aqueous extracts from in vitro produced tissue of sweetpotato (Ipomoea batatas L.)

Anthocyanin-rich aqueous extracts from cell suspension cultures of a high anthocyanin-producing sweetpotato PL (purple line) cell line grown under two different media conditions, MM (multiplication medium) and APM (high anthocyanin-producing medium) and from the cell line's donor tissue, field-grown storage root (SR) of sweetpotato, cv. Ayamurasaki, were evaluated for antioxidative (DPPH test), antimutagenic (Salmonella/reversion assay; mutagen, Trp-P-1), and antiproliferative (human promyelocytic leukaemia cells HL-60) activities. Both cell line extracts MM and APM exhibited higher radical scavenging activities (RSA), 3.8- and 1.4-fold, respectively, than the SR extract. The antimutagenic activity of all extracts was found to be dose-dependent. At a dose of 1 mg/plate, the highest activity exhibited APM (73% inhibition of Trp-P-1-induced reverse mutation of Salmonella typhimurium TA98), followed by MM (54% inhibition) and SR (36% inhibition). The MM extract was the strongest inhibitor of the proliferation of human promyelocytic leukemia cells. At a concentration of 1.6 mg/mL medium during 24 h, it suppressed the growth of 47% of HL-60 cells. A significantly lower growth suppression effect displayed APM and SR extracts (21 and 25%, respectively). Total anthocyanin levels and anthocyanin composition in evaluated samples seem to be related to their activities. The MM extract, which exhibited the highest RSA and antiproliferation activities, contained the highest level of anthocyanins. Among them, nonacylated cyanidin 3-sophoroside-5-glucoside dominated. It is speculated that the presence of this anthocyanin contributed toward enhanced activities of MM extract.     

Composition and stability of anthocyanins in blue-grained wheat

Wheat grain is recognized as a good source of potentially health-enhancing components such as dietary fiber, phenolics, tocopherols, and carotenoids. Anthocyanins, another group of bioactive compounds, are found in blue and purple wheat grains. In the present study, a blue aleurone spring wheat line "Purendo 38" with relatively high content of total anthocyanins was used to investigate the composition and stability of anthocyanins over three crop years. Commercial cultivars of purple (Konini) and red (Katepwa) wheats were included in the study. Separation of anthocyanins by high-performance liquid chromatography (HPLC) showed that each wheat had a distinct anthocyanin profile. Four major anthocyanins were separated from blue wheat extracts as compared to five anthocyanins in purple wheat. Cyanidin 3-glucoside was the predominant anthocyanin in purple wheat, whereas it was the second major anthocyanin in blue wheat. The predominant anthocyanin in blue wheat, making up approximately 41% of the total anthocyanin content, remains to be structurally unidentified. Blue wheat anthocyanins were thermally most stable at pH 1. Their degradation was slightly lower at pH 3 as compared to pH 5. Increasing the temperature from 65 to 95 degrees C increased degradation of blue wheat anthocyanins. Addition of SO(2) during heating of blue wheat had a stabilizing effect on anthocyanin pigments. The optimal SO(2) concentrations were 500-1000 ppm for whole meals and 1000-3000 ppm for isolated anthocyanins. Further studies are underway to identify and verify individual anthocyanins in blue wheat and their potential end uses.     

Effects of solvent and temperature on pressurized liquid extraction of anthocyanins and total phenolics from dried red grape skin

Pressurized liquid extraction (PLE) was used to extract anthocyanins from the freeze-dried skin of a highly pigmented red wine grape with six solvents at 50 degrees C, 10.1 MPa, and 3 x 5 min extraction cycles. Temperature (from 20 to 140 degrees C in 20 degrees C increments) effects on anthocyanin recovery by acidified water and acidified 60% methanol were also studied. Acidified methanol extracted the highest levels of total monoglucosides and total anthocyanins, whereas the solvent mixture (40:40:20:0.1 methanol/acetone/water HCl) extracted the highest levels of total phenolics and total acylated anthocyanins. Acidified water extracts obtained by PLE at 80-100 degrees C had the highest levels of total monoglucosides, total acylated anthocyanins, total anthocyanins, total phenolics, and ORAC values. Acidified methanol extracts obtained by PLE at 60 degrees C had the highest levels of total monoglucosides and total anthocyanins, whereas extracts obtained at 120 degrees C had the highest levels of total phenolics. High-temperature PLE (80-100 degrees C) using acidified water, an environmentally friendly solvent, was as effective as acidified 60% methanol in extracting anthocyanins from grape skins.     

Color stability of commercial anthocyanin-based extracts in relation to the phenolic composition. Protective effects by intra- and intermolecular copigmentation

Anthocyanin extracts are increasingly used as food ingredients. A current challenge is to maintain their color properties. The stability of some colorants has been studied in sugar and non-sugar drink models at three pH values (3, 4, and 5) under thermal and light conditions simulating rapid food aging. At a given pH, color stability mainly depends on the structures of anthocyanins and of colorless phenolic compounds. Colorants rich in acylated anthocyanins (purple carrot, red radish, and red cabbage) display great stability due to intramolecular copigmentation. The protection of red chromophore is higher for diacylated anthocyanins in red radish and red cabbage. For colorants without acylated anthocyanins (grape-marc, elderberry, black currant, and chokeberry), intermolecular copigmentation plays a key role in color protection. Colorants rich in flavonols and with the highest copigment/pigment ratio show a remarkable stability. By contrast, catechins appear to have a negative effect on red colorants, quickly turning yellowish in drink models. This effect is more pronounced when the pH is increased. Finally, color does not seem to be greatly influenced by the addition of sugar.     

LC-PDA-ESI/MS(n) identification of new anthocyanins in purple Bordeaux radish ( Raphanus sativus L. variety)

An LC-PDA-ESI/MS(n) profiling method was used to identify the anthocyanins of purple Bordeaux radish and led to the assignment of 60 anthocyanins: 14 acylated cyanidin 3-(glucosylacyl)acylsophoroside-5-diglucosides, 24 acylated cyanidin 3-sophoroside-5-diglucosides, and 22 acylated cyanidin 3-sophoroside-5-glucosides. The identifications were supported by the presence of 3-sophoroside-5-diglucoside and 3-sophroside-5-glucoside of cyanidin in the alkaline-hydrolyzed extract. A reliable method to identify the anthocyanins containing 3-(glucosylacyl)acylsophorosyl functions is described. The tentative identifications were obtained from tandem mass data analysis and confirmed by high-resolution mass measurements. Further assignments were made for some anthocyanins from a comparison of the mass and UV-vis data and elution order with those of the anthocyanins in the authors' polyphenol database and from consideration of the structural characteristics of the anthocyanins from similar plants and similar anthocyanins in the literature. The presence of 38 acylated cyanidin 3-sophoroside-5-diglucosides and around 10 acylated cyanidin 3-sophoroside-5-malonylglucosides in plants is reported here for the first time.     

Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity

Anthocyanins and proanthocyanidins were characterized by HPLC-ESI-MS/MS coupled with a diode array and/or fluorescent detector in seven cultivars of Ribes nigrum (black currant) and Ribes rubrum (red currant, Red Lake), six cultivars of Ribes grossularia (gooseberries), Aronia melanocarpa(chokeberry), and Sambucus nigra (elderberry). Thirty-one different anthocyanins were detected in these berries, but not every anthocyanin was observed in each berry. A number of minor anthocyanins were identified from these berries for the first time. The concentrations of individual anthocyanins in all of the berries were quantified using relevant anthocyanidin 3-glucoside standards. Among the berries studied in this paper and in berries in general, chokeberry has the highest total anthocyanin concentrations [1480 mg/100 g of fresh weight (FW)], whereas the lowest total anthocyanin concentration in the berries studied was found in the gooseberry cv. Careless, which contained only 0.07 mg/100 g of FW. Two cultivars of gooseberries (Marigold and Leveller) did not contain any anthocyanins. Total proanthocyanidin concentrations in the berries studied ranged from 23 to 664 mg/100 g of FW in elderberry and chokeberry, respectively. Procyanidin or prodelphinidin polymers were the predominant components (>65% w/w) in most of the berries. The lipophilic and hydrophilic antioxidant capacities were measured by the oxygen radical absorbance capacity (ORAC(FL)) procedure. The total antioxidant capacity varied from 21 micromol of TE/g of FW in Careless gooseberry to 161 micromol of TE/g of FW in chokeberry. Total phenolics in the berries in general paralleled hydrophilic antioxidant capacity.