Chapter 9B
Flavanols, Flavonols and Dihydroflavonols
Nancy Terrier, C ́eline Poncet-Legrand, and Veronique Cheynier ́
Contents
9B.1 StructureandOccurrenceinGrape ........................................... 463
9B.1.1 GeneralStructuralCharacteristics .................................... 463
9B.1.2 Flavanols ......................................................... 465
9B.1.3 Flavonols and Dihydroflavonols................................ ...... 473
9B.2 ExtractionintotheWine.................................................... 474
9B.2.1 WhiteWines ...................................................... 474
9B.2.2 RedWines ........................................................ 475
9B.3 ReactionsinWine ......................................................... 477
9B.3.1 Flavonoid Reactivity....... ........................................ 477
9B.3.2 EnzymaticProcesses ............................................... 478
9B.3.3 ChemicalReactions ................................................ 478
9B.4 Interactions with Other Grape and Wine Constituents..................... ...... 486
9B.4.1 InteractionProcesses ............................................... 486
9B.4.2 Flavonoid Interactions...... ........................................ 487
9B.4.3 Flavonoid Interactions with Other Macromolecules................ ...... 490
9B.4.4 Flavonoid Adsorption on Solid Material......................... ...... 494
References ............................................................... 496
9B.1 Structure and Occurrence in Grape
9B.1.1 General Structural Characteristics
Flavanols, flavonols, and dihydroflavonols, like the anthocyanins presented in
Chapter 9A, belong to the flavonoid family. These compounds are phenolic com-
pounds that share a common C6-C3-C6 skeleton consisting of two phenolic rings
(named A and B) linked together by a heterocyclic pyran ring (C-ring) as shown
in Fig. 9B.1. Among them, several classes can be distinguished on the basis of
V. Cheynier (B)
INRA, UMR Sciences pour l’Oenologie, 2, place Viala, F-34060
Montpellier, France
e-mail: [email protected]
M.V. Moreno-Arribas, M.C. Polo (eds.),Wine Chemistry and Biochemistry,
DOI 10.1007/978-0-387-74118-518,©CSpringer Science+Business Media, LLC 2009
463