Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: structure-activity relationship

Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: structure-activity relationship

The topical anti-inflammatory activity of three non-phenolic linear 1,7-diarylheptanoids, previously isolated from a Thai medicinal plant, Curcuma xanthorrhiza (Zingiberaceae) and four new semi-synthetic derivatives of the naturally occurring compounds were assessed in the murine model of ethyl phen...

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Bibliographic Details
Published in:Planta medica Vol. 62; no. 3; p. 236
Main Authors: Claeson, P, Pongprayoon, U, Sematong, T, Tuchinada, P, Reutrakul, V, Soontornsaratune, P, Taylor, W C
Format: Journal Article
Language:English
Published: Germany 01-06-1996
Subjects:
Alkynes
Animals
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - isolation & purification
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Asia, Southeastern
Edema - chemically induced
Edema - drug therapy
Heptanes - chemical synthesis
Heptanes - isolation & purification
Heptanes - pharmacology
Inflammation
Male
Molecular Structure
Oxyphenbutazone - pharmacology
Plants, Medicinal
Rats
Rats, Sprague-Dawley
Structure-Activity Relationship
Asia, Southeastern
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Summary:The topical anti-inflammatory activity of three non-phenolic linear 1,7-diarylheptanoids, previously isolated from a Thai medicinal plant, Curcuma xanthorrhiza (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 micrograms/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:0032-0943
DOI:10.1055/s-2006-957867