New polyphenolic compounds with xanthylium skeletons formed through reaction between (+)-catechin and glyoxylic acid.
The reaction between (+)-catechin and glyoxylic acid was studied in a model solution system. The major (+)-catechin carboxymethine-linked dimer was isolated and shown to proceed to new polyphenolic compounds exhibiting absorption maxima around 440 and 460 nm. Three yellow pigments were obtained by incubation of the 8-8 colorless isomer. One was the previously reported xanthylium compound NJ2 with a maximum at 440 nm. The other two, showing absorption maxima at 460 nm, were obtained separately by incubation of the colorless dimer in hydroethanolic or methanolic medium. Structural elucidation of these two new yellow pigments was achieved by means of MS and 1D and 2D NMR techniques and showed that they were, respectively, ethyl and methyl esters of NJ2. The fact that these compounds were not obtained when NJ2 was incubated in hydromethanolic or ethanolic medium showed that esterification took place before the formation of the xanthylium chromophores. The detection of the esterified colorless compounds and the corresponding xanthene intermediates confirmed the postulated mechanism. New pigments exhibiting a strong absorption at 560 nm were also observed.
Es-Safi
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NE
ISVV-INRA Institut des Produits de la Vigne, Unité de Recherche Biopolymères et Arômes, 2 place Viala, 34060 Montpellier, France. essafi@ensam.inra.fr
Le Guernevé
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C
Fulcrand
H
H
Cheynier
V
V
Moutounet
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M
D002392:Catechin / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids; D005511:Food Handling; D008401:Gas Chromatography-Mass Spectrometry; D006038:Glyoxylates / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D010860:Pigments, Biological / Q000138:chemical synthesis / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014966:Xanthenes / Q000737:chemistry*
D005419:Flavonoids; D006038:Glyoxylates; D010636:Phenols; D010860:Pigments, Biological; D011108:Polymers; D014966:Xanthenes; D002392:Catechin; C031150:glyoxylic acid