title: Fate of Anthocyanins through Cocoa Fermentation. Emergence of New Polyphenolic Dimers.
abstract: Fresh, ripe cocoa beans from Cameroon (German cocoa/Amelonado group and ICS 40/Trinitario group) were subjected to fermentation-like incubations in acetic acid, lactic acid, or both and to natural fermentation. Two naturally fermented samples from Cuba (UF 654/Trinitario group and C 411/Criollo group) were also investigated. Both cyanidin-3-galactoside and cyanidin-3-arabinoside (found as major anthocyanins in colored beans only) were drastically degraded through fermentation, especially in small beans and in the presence of acetic acid. On the other hand, emergence of a cyanidin-rhamnose isomer was evidenced, even in Criollo beans. In addition to the recently described structures F1 and F2 [m/z = 575 in ESI(-)], three additional polyphenolic structures [F3, F4, and F5; m/z = 557 in ESI(+)] were found after fermentation, the two former ones resulting from epicatechin oxidation. Synthesis of F5 requires an interclass reaction between cyani(di)n and epicatechin, which explains its absence in fermented Criollo beans.
authors.affiliation: Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, ELIM, Faculté des Bioingénieurs, Université catholique de Louvain , Croix du Sud, 2 box L07.05.07, B-1348 Louvain-la-Neuve, Belgium.
authors.forename: Cédric
authors.initials: C
authors.lastname: De Taeye
authors.affiliation: Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, ELIM, Faculté des Bioingénieurs, Université catholique de Louvain , Croix du Sud, 2 box L07.05.07, B-1348 Louvain-la-Neuve, Belgium.|Laboratory of Plant Physiology, Department of Biological Sciences, Higher Teacher's Training College, University of Yaounde I , P.O. Box 47, Yaounde, Cameroon.
authors.forename: Victor Jos
authors.initials: VJ
authors.lastname: Eyamo Evina
authors.affiliation: Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, ELIM, Faculté des Bioingénieurs, Université catholique de Louvain , Croix du Sud, 2 box L07.05.07, B-1348 Louvain-la-Neuve, Belgium.
authors.forename: Gilles
authors.initials: G
authors.lastname: Caullet
authors.affiliation: Laboratory of Plant Physiology, Department of Biological Sciences, Higher Teacher's Training College, University of Yaounde I , P.O. Box 47, Yaounde, Cameroon.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Niemenak
authors.affiliation: Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, ELIM, Faculté des Bioingénieurs, Université catholique de Louvain , Croix du Sud, 2 box L07.05.07, B-1348 Louvain-la-Neuve, Belgium.
authors.forename: Sonia
authors.initials: S
authors.lastname: Collin
mesh_terms: D000872:Anthocyanins / Q000378:metabolism; D002099:Cacao / Q000737:chemistry*; D019281:Dimerization; D005285:Fermentation; D010936:Plant Extracts / Q000737:chemistry*; D059808:Polyphenols / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry
chemical_list: D000872:Anthocyanins; D010936:Plant Extracts; D059808:Polyphenols
keywords: Criollo; anthocyanin; cocoa fermentation; cyanidin-rhamnoside; epicatechin