Chapter 9A
Anthocyanins and Anthocyanin-Derived
Compounds
Mar ́ıa Monagas and Begona Bartolome ́
Contents
9A.1 GeneralConsiderationsofAnthocyaninsinWine............................... 439
9A.2 Chemical Reactions of Anthocyanins During Winemaking: Main Anthocyanin-
Derived Compounds............................ ........................... 442
9A.2.1 Reactions of Anthocyanins with Enzymatically Generatedo-Quinones..... 443
9A.2.2 Anthocyanin-Flavanol and Anthocyanin-Anthocyanin Direct Condensation
Reactions .........................................................444
9A.2.3 Anthocyanin-Flavanol and Anthocyanin-Anthocyanin Aldehyde-Mediated
Condensation Reactions .............................................447
9A.2.4 ReactionsLeadingtoPyranoanthocyanin Formation..................... 449
9A.3 EnzymaticDeglycosilationofAnthocyaninsDuringWinemaking ................. 455
9A.4 AdsorptionofAnthocyaninsonYeastCellWalls ............................... 455
References ............................................................... 456
9A.1 General Considerations of Anthocyanins in Wine
Structural characteristics and occurrence. Anthocyanins are mainly located in
the grape skins, with the exception of the teinturier varieties that also contain
anthocyanins in the pulp. The anthocyanins identified in grape skins and wines
fromVitis viniferaare the 3-O-monoglucosides and the 3-O-acylated monogluco-
sides of five main anthocyanidins – delphinidin, cyanidin, petunidin, peonidin and
malvidin – which differ from each other by the number and position of the hydroxyl
and methoxyl groups located in the B-ring of the molecule (Fig. 9A.1). Acylation
occurs at the C-6 position of the glucose molecule by esterification with acetic,
p-coumaric and caffeic acids (Mazza and Miniati 1993). Recently, the existence of
anthocyanins acylated with lactic acid, originating in wine from grape anthocyanins,
has been reported (Alcalde-Eon et al. 2006).
In the last few years, the use of mass spectrometry techniques (FAB-MS,
ESI-MS/MS, MALDI-MS, HPLC/API-MS and HPLC/ESI-MS) has allowed
B. Bartolom ́e(B)
Instituto de Fermentaciones Industriales, CSIC. Juan de la Cierva 3, 28006 Madrid, Spain.
e-mail: [email protected]
M.V. Moreno-Arribas, M.C. Polo (eds.),Wine Chemistry and Biochemistry,
DOI 10.1007/978-0-387-74118-517,©CSpringer Science+Business Media, LLC 2009
439