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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

The absolute configuration of 1-(3 ',4 '-dihydroxycinnamoyl)cyclopentane-2,3-diol from the Amazonian tree Chimarrhis turbinata

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Author(s):
Cardoso, Carmen Lucia ; Bolzani, Vanderlan da Silva [2] ; Silva, Dulce Helena Siqueira ; Ishii, Hideki ; Berova, Nina ; Nakanishi, Koji
Total Authors: 6
Document type: Journal article
Source: Journal of Natural Products; v. 69, n. 7, p. 1046-1050, July. 2006.
Field of knowledge: Physical Sciences and Mathematics - Chemistry
Abstract

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 1 was 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. (AU)

FAPESP's process: 03/02176-7 - Conservation and sustainable use of the diversity from Cerrado and Atlantic Forest: chemical diversity and prospecting for potential drugs - phase II
Grantee:Vanderlan da Silva Bolzani
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants