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Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa.


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Title: Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa.
Authors: Huang, Yong-Lin / Tsujita, Takaaki / Tanaka, Takashi / Matsuo, Yosuke / Kouno, Isao / Li, Dian-Peng / Nonaka, Gen-Ichiro
Issue Date: Nov-2011
Publisher: Elsevier BV
Citation: Phytochemistry, 72(16), pp.2006-2014; 2011
Abstract: Triterpene hexahydroxydiphenoyl (HHDP) esters have only been isolated from Castanopsis species, and the distribution of these esters in nature is of chemotaxonomical interest. In this study, the chemical constituents of the leaves of Castanopsis fissa were examined in detail to identify and isolate potential HHDP esters. Together with 53 known compounds, 3,4-di-O-galloyl-1-O-purpurogallin carbonyl quinic acid (1) and 3,24-(S)-HHDP-2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide (2) were isolated and their structures were elucidated by spectroscopic and chemical methods. The polyphenols of the leaves were mainly composed of galloyl quinic acids, triterpenes HHDP esters, ellagitannins and flavonol glycosides. In particular, the isolation yields of 1,3,4-trigalloyl quinic acid and compound 2 were 1.53% and 0.27%, respectively, from the fresh leaves. The presence of lipid soluble HHDP esters of oleanane-type triterpenes as one of the major metabolites is an important chemotaxonomical discovery. Lipase inhibition activities and ORAC values of the major constituents were compared. The triterpene HHDP ester showed moderate lipase inhibition activity and myricitrin gave the largest ORAC value.
Keywords: Benzotropolone / Castanopsis fissa / Ellagitannin / Fagaceae / Galloyl quinic acid / Purpurogallin / Triterpene
URI: http://hdl.handle.net/10069/25834
ISSN: 00319422
DOI: 10.1016/j.phytochem.2011.07.007
PubMed ID: 21831402
Rights: Copyright © 2011 Elsevier Ltd. All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/25834

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