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Cyclohexanecarboxylic‐Acid Derivatives from Psiadia trinervia
Author(s) -
Wang Ying,
Hamburger Matthias,
Gueho Joseph,
Hostettmann Kurt
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750122
Subject(s) - quinic acid , chemistry , caffeic acid , chlorogenic acid , chirality (physics) , hydrolysis , ethyl ester , chromatography , stereochemistry , organic chemistry , antioxidant , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
From a MeOH extra of Psiadia trinervia , seven phenolic compounds were isolated by gel filtration and reversed‐phase chromatography. Six of them are known compounds, namely 3,4‐di‐ O ‐caffeoylquinic acid ( 2 ), 3,5‐di‐ O ‐caffeoylquinic acid ( 3 ), caffeic acid, and three 3‐methoxyflavonoids. Compound 1 is a 3,4‐di‐ O ‐caffeoyl derviative of (1 S ,3 R ,4 R ,5 R )‐1,3,4, 5‐tetrahydroxycyclohexanecarboxylic acid, a novel steroisomer of (−)‐quinic acid. Following hydrolytic treatment of the MeOH extract, ethyl 3‐ O ‐caffeoylquinate ( 4 ), ethyl 3,4‐di‐ O ‐caffeoylquinate ( 5 ), and ethyl 3,5‐ O ‐caffeoylquinate ( 6 ) were isolated. The latter three compounds are artifacts. The configuration of 1‐3 was established by NMR and CD (exciton chirality method).