Wine Chemistry and Biochemistry

(Steven Felgate) #1
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


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