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Title: Non-Phenolic Linear Diarylheptanoids from Curcuma xanthorrhiza: A Novel Type of Topical Anti-Inflammatory Agents: Structure-Activity Relationship
Authors: P. Claeson
U. Pongprayoon
T. Sematong
P. Tuchinda
V. Reutrakul
P. Soontornsaratune
W. C. Taylor
Mahidol University
Rangsit University
Thailand Institute of Scientific and Technological Research (TISTR)
The University of Sydney
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Medicine;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 1-Dec-1996
Citation: Planta Medica. Vol.62, No.3 (1996), 236-240
Abstract: The topical anti-inflammatory activity of three nonphenolic linear 1,7-diarylheptanoids, previously isolated from a Thai medicinal plant, Curcuma xonthorrhiza (Zingiberaceae) and four new semi-synthetic derivatives of the naturally occurring compounds were assessed in the murine model of ethyl phenylpropiolate-induced ear edema. The naturally occurring compound 1E,3E,1,7-diphenylheptadien-5-one (6) exerted the most potent anti-inflammatory activity, with an ID50 value of similar magnitude to that of the reference drug oxyphenbutazone (67 vs. 46 μg|ear, respectively). None of the semi-synthetic diarylheptanoids was more active than 6. The chemical structures and pharmacological data of the natural and semi-synthetic derivatives identified a distinct structure-activity relationship. The degree of unsaturation in positions 1 and 3, and the nature of the oxygenated functional group in position 5 of the C7-chain were found to play significant roles in determining the observed in vivo activity. Based on these findings, the non-phenolic linear 1,7-diarylheptanoids are proposed to represent a novel class of topical anti-inflammatory agents.
ISSN: 00320943
Appears in Collections:Scopus 1991-2000

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