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Article Dans Une Revue Journal of Natural Products Année : 2016

Synthesis, identification, and structure elucidation of adducts formed by reactions of hydroxycinnamic acids with glutathione or cysteinylglycine

Résumé

Grape polyphenols, especially hydroxycinnamic acids such as caftaric and ca ff eic acid, are prone to enzymatic oxidation reactions during the winemaking process, forming o -quinones and leading to color darkening. Glutathione is capable of trapping these o -quinones and thus limiting juice browning. In this study, the addition of glutathione or cys- teinylglycine onto caftaric or ca ff eic acid o -quinones formed by polyphenoloxidase-catalyzed reactions was investigated by UPLC-DAD-ESIMS and NMR data analyses. Complete iden- ti fi cation of adducts has been achieved via NMR data. The results con fi rmed that the favored reaction is the substitution of the sulfanyl group of cysteine at C-2 of the aromatic ring. Several minor isomers, namely, the cis -isomer of the 2- S adduct and trans -isomers of the 5- S and 6- S adducts, and the 2,5-di- S -glutathionyl adducts were also identi fi ed and quanti fi ed by qNMR. With the exception of 2-( S -glutathionyl)- and 2,5-di( S -glutathionyl)- trans -caftaric acid, these products had never been formally identi fi ed. In particular, the 5- S and 6- S derivatives are reported here for the fi rst time. The fi rst formal identi fi cation of 2- S cis - derivatives is also provided. Moreover, NMR and UPLC-DAD-ESIMS analysis showed that signature UV and MS spectra can serve as markers of the conformation and substitution position in the aromatic ring for each of the isomers
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Dates et versions

hal-01397453 , version 1 (15-11-2016)

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Nayla Ferreira Lima, Anna Vallverdu Queralt, Emmanuelle Meudec, Jean Paul Mazauric, Nicolas Sommerer, et al.. Synthesis, identification, and structure elucidation of adducts formed by reactions of hydroxycinnamic acids with glutathione or cysteinylglycine. Journal of Natural Products, 2016, 79 (9), pp.2211-2222. ⟨10.1021/acs.jnatprod.6b00279⟩. ⟨hal-01397453⟩
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