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Review
. 2013 Sep 27;14(10):19651-69.
doi: 10.3390/ijms141019651.

Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols

Riccardo Flamini  1 , Fulvio Mattivi, Mirko De Rosso, Panagiotis Arapitsas, Luigi Bavaresco
Affiliations
Review

Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols

Riccardo Flamini et al. Int J Mol Sci. .

Abstract

Grape is qualitatively and quantitatively very rich in polyphenols. In particular, anthocyanins, flavonols and stilbene derivatives play very important roles in plant metabolism, thanks to their peculiar characteristics. Anthocyanins are responsible for the color of red grapes and wines and confer organoleptic characteristics on the wine. They are used for chemotaxonomic studies and to evaluate the polyphenolic ripening stage of grape. They are natural colorants, have antioxidant, antimicrobial and anticarcinogenic activity, exert protective effects on the human cardiovascular system, and are used in the food and pharmaceutical industries. Stilbenes are vine phytoalexins present in grape berries and associated with the beneficial effects of drinking wine. The principal stilbene, resveratrol, is characterized by anticancer, antioxidant, anti-inflammatory and cardioprotective activity. Resveratrol dimers and oligomers also occur in grape, and are synthetized by the vine as active defenses against exogenous attack, or produced by extracellular enzymes released from pathogens in an attempt to eliminate undesirable toxic compounds. Flavonols are a ubiquitous class of flavonoids with photo-protection and copigmentation (together with anthocyanins) functions. The lack of expression of the enzyme flavonoid 3',5'-hydroxylase in white grapes restricts the presence of these compounds to quercetin, kaempferol and isorhamnetin derivatives, whereas red grapes usually also contain myricetin, laricitrin and syringetin derivatives. In the last ten years, the technological development of analytical instrumentation, particularly mass spectrometry, has led to great improvements and further knowledge of the chemistry of these compounds. In this review, the biosynthesis and biological role of these grape polyphenols are briefly introduced, together with the latest knowledge of their chemistry.

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Figures

Figure 1
Figure 1
General phenylpropanoid pathway. PAL, phenylalanine ammonia lyase; C4H, cinnamate-4-hydroxylase; 4CL, 4-coumaroyl:CoA-ligase; CHS, chalcone synthase; STS, stilbene synthase.
Figure 2
Figure 2
Flavonoid pathway. CHS, chalcone synthase; CHI, chalcone isomerase; F3′H, flavonoid-3′-hydroxylase; F3′5′H, flavonoid-3′,5′-hydroxylase; F3H, flavanone-3-hydroxylases; FLS, flavonol synthase; DFR, dihydroflavonol reductase; LAR, leucoanthocyanidin reductase; LDOX, leucoanthocyanidin dioxigenase; ANR, anthocyanidin reductase; UFGT, UDP-glucose:flavonoid 3-O-glucosyl transferase; OMT, O-methyltransferase.
Figure 3
Figure 3
Structures of the principal V. vinifera grape anthocyanins.
Figure 4
Figure 4
Structures of anthocyanins identified in 21 different hybrid red grape varieties.
Figure 5
Figure 5
Structures of stilbenes in grape. (1) Z- and E-astringin; (2) Z- and E-piceid; (3) pterostilbene (3,5-dimethoxy-4′-hydroxystilbene); (4) piceatannol; (5) pallidol; (6) pallidol-3-O-glucoside; (7) parthenocissin A; (8) trans-resveratrol; (9) resveratroloside; (10) hopeaphenol; (11) ampelopsin H; (12) caraphenol B; (13) vaticanol C isomer; (14) resveratrol-4′-O-β-d-glucopyranoside; (15) isohopeaphenol; (16) E- and Z-ɛ-viniferin; (17) E- and Z-miyabenol C; (18) E- and Z-δ-viniferin; (19) trans-resveratrol-4′-methyl ether.
Figure 6
Figure 6
Flavonols pathway. The trihydroxylated flavonols myricetin, laricitrin and syringetin are lacking in the berries of white grapes.
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