Colour variation in red grapevines (Vitis vinifera L.): genomic organisation, expression of flavonoid 3'-hydroxylase, flavonoid 3',5'-hydroxylase genes and related metabolite profiling of red cyanidin-/blue delphinidin-based anthocyanins in berry skin
Simone D. CastellarinGabriele Di GasperoRaffaella MarconiAlberto NonisE. PeterlungerSophie PaillardAnne‐Françoise Adam‐BlondonR. Testolin
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Abstract Background Structural genes of the phenyl-propanoid pathway which encode flavonoid 3'- and 3',5'-hydroxylases (F3'H and F3'5'H) have long been invoked to explain the biosynthesis of cyanidin- and delphinidin-based anthocyanin pigments in the so-called red cultivars of grapevine. The relative proportion of the two types of anthocyanins is largely under genetic control and determines the colour variation among red/purple/blue berry grape varieties and their corresponding wines. Results Gene fragments of VvF3'H and VvF3'5'H , that were isolated from Vitis vinifera 'Cabernet Sauvignon' using degenerate primers designed on plant homologous genes, translated into 313 and 239 amino acid protein fragments, respectively, with up to 76% and 82% identity to plant CYP75 cytochrome P450 monooxygenases. Putative function was assigned on the basis of sequence homology, expression profiling and its correlation with metabolite accumulation at ten different ripening stages. At the onset of colour transition, transcriptional induction of VvF3'H and VvF3'5'H was temporally coordinated with the beginning of anthocyanin biosynthesis, the expression being 2-fold and 50-fold higher, respectively, in red berries versus green berries. The peak of VvF3'5'H expression was observed two weeks later concomitantly with the increase of the ratio of delphinidin-/cyanidin-derivatives. The analysis of structural genomics revealed that two copies of VvF3'H are physically linked on linkage group no. 17 and several copies of VvF3'5'H are tightly clustered and embedded into a segmental duplication on linkage group no. 6, unveiling a high complexity when compared to other plant flavonoid hydroxylase genes known so far, mostly in ornamentals. Conclusion We have shown that genes encoding flavonoid 3'- and 3',5'-hydroxylases are expressed in any tissues of the grape plant that accumulate flavonoids and, particularly, in skin of ripening red berries that synthesise mostly anthocyanins. The correlation between transcript profiles and the kinetics of accumulation of red/cyanidin- and blue/delphinidin-based anthocyanins indicated that VvF3'H and VvF3'5'H expression is consistent with the chromatic evolution of ripening bunches. Local physical maps constructed around the VvF3'H and VvF3'5'H loci should help facilitate the identification of the regulatory elements of each isoform and the future manipulation of grapevine and wine colour through agronomical, environmental and biotechnological tools.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.
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Peonidin
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Anthocyanins are a major group of red to blue spectrum plant pigments with many consumer health benefits. Anthocyanins are derived from the flavonoid pathway and diversified by glycosylation and methylation, involving the concerted action of specific enzymes. Blueberry and bilberry (Vaccinium spp.) are regarded as 'superfruits' owing to their high content of flavonoids, especially anthocyanins. While ripening-related anthocyanin production in bilberry (V. myrtillus) and blueberry (V. corymbosum) is regulated by the transcriptional activator MYBA1, the role of specific structural genes in determining the concentration and composition of anthocyanins has not been functionally elucidated. We isolated three candidate genes, CHALCONE SYNTHASE (VmCHS1), ANTHOCYANIDIN SYNTHASE (VmANS) and UDP-GLUCOSE : FLAVONOID-3-O-GLYCOSYLTRANSFERASE (VcUFGT2), from Vaccinium, which were predominantly expressed in pigmented fruit skin tissue and showed high homology between bilberry and blueberry. Agrobacterium-mediated transient expression of Nicotiana benthamiana showed that overexpression of VcMYBA1 in combination with VmANS significantly increased anthocyanin concentration (3-fold). Overexpression of VmCHS1 showed no effect above that induced by VcMYBA1, while VcUFGT2 modulated anthocyanin composition to produce delphinidin-3-galactosylrhamnoside, not naturally produced in tobacco. In strawberry (Fragaria × ananassa), combined transient overexpression of VcUFGT2 with a FLAVONOID 3´,5´-HYDROXYLASE from kiwifruit (Actinidia melanandra) modulated the anthocyanin profile to include galactosides and arabinosides of delphinidin and cyanidin, major anthocyanins in blueberry and bilberry. These findings provide insight into the role of the final steps of biosynthesis in modulating anthocyanin production in Vaccinium and may contribute to the targeted breeding of new cultivars with improved nutritional properties.
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Vaccinium myrtillus
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Abstract. Anggraini T, Syukri D, Manasikan TW, Nakano K. 2020. Anthocyanin profile of Syzygium oleana young leaves and fruits using triple quadrupole mass spectrometer: Identification of a new peonidin. Biodiversitas 21: 5893-5900. Anthocyanin is pigment present in many red, blue and purple colored plants that can be used as stable food-safe colorings and also offer health benefits as antioxidants. Syzygium oleana, with its dark purple fruit and red leaves, is one hitherto unexplored source of anthocyanin. This study is the first to establish the anthocyanin profile of S. oleana leaves and fruit exploiting the speed and accuracy of Multiple Reaction Monitoring (MRM) with a triple quadrupole mass spectrometer. The anthocyanin compounds in the leaves and fruit of S. oleana were found to be derivatives of agliconpeonidin, cyanidin derivative, delphinidin. It was found that while both leaves and fruit of S. oleana contain the anthocyanin precursors cyanidin, delphinidin, petunidin, and peonidin. Fruit contains the anthocyanin malvidin and a large amount of petunidin not present in the leaves. In detail: anthocyanin found in S. oleana leaves were Cyanidin 3-galactoside, cyanidin with m/z 611, Delphinidin 3-O-β-D-glucopyranoside, and unknown peonidin. Anthocyanin in S. oleana fruits was cyanidin with m/z 449.1, delphinidin 3-O-β-D-glucopyranoside, petunidin with m/z 476, Malvidin 3-O-β-D-glucopyranoside, and an unknown peonidin. Fruit could be a better anthocyanin source and more effective as colorant than leaves, while leaves contain a stronger as yet unidentified antioxidant.
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Putative flavanol−anthocyanin condensation products were detected in a polyphenol-rich concentrate from black currant (Ribes nigrum L.). These compounds had UV−vis spectra similar to those of delphinidin-3-O-rutinoside and cyanidin-3-O-rutinoside, but eluted before all previously described anthocyanins on reversed phase HPLC. Mass spectrometric data indicated that they were rutinoside derivatives of novel aglycons 304 amu greater than delphinidin and cyanidin, respectively. The compounds were partly purified by semipreparative HPLC and gave MS and MS2 spectra consistent with anthocyanin rutinosides covalently linked to epigallocatechin or gallocatechin. These compounds are similar in structure to compounds thought to influence color and quality in red wines and strawberry juice products. There was also evidence for the presence of a range of other flavanol−anthocyanin condensation products. The compounds were present at differing levels in juices of 10 black currant varieties, which were roughly correlated to the content of the parent anthocyanins. The flavanol−anthocyanin products were present in polyphenol-enriched concentrates obtained by solid phase extraction, in commercially produced concentrates, and in fresh extracts of black currants. This suggests that the compounds were not artifacts formed during concentration or purification. However, differences in their comparative contents may be related to the lability of the parent anthocyanins during processing. Although present at low levels, the flavanol−anthocyanin products may influence color or quality parameters of black currant juices, and they may confer enhanced stability to the biological activities reported for their anthocyanin parents. Keywords: Anthocyanins; flavanols; black currant; Ribes nigrum; polyphenol; condensation products
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Ethephon
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Flavanone
Chalcone isomerase
Anthocyanidins
Flavonoid Biosynthesis
Plant Physiology
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Nierembergia sp., a popular floricultural species, only has violet and white flower color and lacks pink to red. To elucidate the reason, we analyzed its flavonoids. Its major anthocyanin was determined to be delphinidin 3-O-(6-O-(4-O-(4-O-(6-O-caffeoyl-β-D-glucopyranosyl)-p-coumaroyl)-α-L-rhamnosyl)-β-D-glucopyranosyl)-5-O-β-D-glucopyranoside. The petals rarely contained cyanidin and pelargonidin, and they contained more flavonols than anthocyanins. We also characterized the biosynthetic pathway by cloning the cDNAs encoding enzymes involved in the flavonoid biosynthesis pathway: chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), flavonoid 3′-hydroxylase (F3′H), flavonoid 3′,5′-hydroxylase (F3′5′H), dihydroflavonol 4-reductase (DFR), flavonol synthase (FLS), and UDP-rhamnose: anthocyanidin 3-glucoside rhamnosyltransferase (3RT). Northern blot analysis revealed that the expressions of CHS, F3′5′H, DFR, and 3RT genes were coordinately regulated in parallel with anthocyanin accumulation in the petals, indicating that anthocyanin biosynthesis is transcriptionally regulated; on the other hand, the transcripts of the F3′H gene were rarely detected. Antisense suppression of the F3′5′H gene decreased the amount of F3′5′H transcripts and that of delphinidin. It was noteworthy that the color of the transgenic flower changed from violet to white rather than to reddish, which was the expectation.
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Petal
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Flavanone
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Anthocyanins are the most important polyphenolic substances contained in blackcurrant fruits. They are responsible for the various health benefits caused, in particular, by their high antioxidant activity. Anthocyanins derived from anthocyanidins cyanidin and delphinidin are typical for blackcurrant fruits, especially their rutinoside and glucoside forms. These four anthocyanins usually represent about 97–98% of total anthocyanins in blackcurrant fruits. In this study, we developed and validated a new HPLC-DAD method for rapid anthocyanin separation and determination in fifteen perspective blackcurrant cultivars (‘Ruben’, ‘Ben Lomond’, ‘Ben Conan’, ‘Ceres’, ‘Moravia’, ‘Ometa’, ‘Lota’, ‘Fokus’, ‘Tenah’, ‘Sejanec’, ‘Consort’, ‘Triton’, ‘Ben Hope’, ‘Ben Gairn’, and one gooseberry hybrid ‘Josta’). Eight of them were monitored throughout the three-year experiment. The most represented anthocyanins in all monitored blackcurrant cultivars were delphinidin-3-rutinoside (36.7–63.6%), cyanidin-3-rutinoside (26.4–40.6%), delphinidin-3-glucoside (6.1–17.9%), and cyanidin-3-glucoside (1.3–9.9%). The individual anthocyanin proportion (%) in each cultivar was specific, and a similar profile was verified in a three-year period for eight available cultivars. Total anthocyanin content expressed as a sum of four major anthocyanins present in blackcurrants was compared with values expressed as the equivalent of cyanidin-3-glucoside, as many authors do. We revealed an underestimation of about 20% with the latter method. Cultivars with the highest average total anthocyanin content were ‘Ben Gairn’ (294.38 mg/100 g), ‘Ceres’ (281.31 mg/100 g), and ‘Ometa’ (269.09 mg/100 g).
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In recent years, considerable attention has been paid to anthocyanins due to their abilities to inhibit oxidative stress and cell proliferation. The regulations of apoptosis and the phase II enzymes glutathione-S-transferase (GST) and quinone reductase (QR) are other potential mechanisms through which flavonoids such as anthocyanins may prevent cancer. Our study confirmed that anthocyanin fractions from high bush blueberry cultivars increased apoptosis using two different methods: DNA fragmentation and caspase-3 activity. The effect of anthocyanins on the activity of the detoxifying enzymes GST and QR was also determined. Major anthocyanins identified were delphinidin, cyanidin, peonidin, petunidin, and malvidin. In Tifblue and Powderblue cultivars, DNA fragmentation increased at anthocyanin concentrations from 50 to 150 μg/mL, but cells treated with the anthocyanin fraction of Brightblue and Brightwell showed a prominent ladder at 50−100 μg/mL when compared to cells treated with 150 μg/mL. There was a significant difference in the caspase-3 activity (P < 0.05) between the control cells and the cells treated with anthocyanins from all of the cultivars. The response correlated positively with dose. The QR activity was lower in all cells treated with an anthocyanin fraction from Tifblue, Powderblue, Brightblue, and Brightwell cultivars than in control cells (P < 0.05). The activity decreased gradually when treated with increased concentrations of anthocyanin fractions (50−150 μg/mL) in the Tifblue and Powderblue cultivars. The GST activity was lower (P < 0.05) in cells treated with anthocyanin fractions from all of the cultivars and at all concentrations. These results indicated that apoptosis was confirmed in HT-29 cells when treated with anthocyanins from blueberry cultivars at 50−150 μg/mL concentrations, but these same concentrations decrease QR and GST activities rather than induce them. Keywords: Anthocyanins; blueberries; caspase-3; cultivars; DNA fragmentation; DNA ladder; glutathione-S-transferase; phase-II enzymes; quinone reductase
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Peonidin
Pelargonidin
Glutathione reductase
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