The Absolute Configuration of 1-(3‘,4‘-Dihydroxycinnamoyl)cyclopentane-2,3-diol from the Amazonian Tree Chimarrhis turbinata

Autor: Lucia Cardoso, Carmen, da Silva Bolzani, Vanderlan, Helena Siqueira Silva, Dulce, Ishii, Hideki, Berova, Nina, Nakanishi, Koji
Zdroj: Journal of Natural Products; July 2006, Vol. 69 Issue: 7 p1046-1050, 5p
Abstrakt: An antioxidant, 1-(3‘,4‘-dihydroxycinnamoyl)cyclopentane-2,3-diol or (E)-2,3-dihydroxycyclopentyl-3-(3‘,4‘-dihydroxyphenyl)acrylate (1), and two known trans-and cis-chlorogenic acid methyl esters were isolated from the ethanolic extract of the leaves of Chimarrhis turbinata. The relative configuration of 1was determined by NMR and by comparison of the circular dichroic spectrum (CD) with those of the enantiomers of synthetic 3‘,4‘-dimethoxycinnamoyl analogues. The absolute configuration of one of the synthetic enantiomers was determined using the CD exciton chirality method. This established the structure of naturally occurring 1 as (E)-2,3-dihydroxycyclopentyl-3-(3‘,4‘-dihydroxyphenyl)acrylate.
Databáze: Supplemental Index