Non-Phenolic Linear Diarylheptanoids from Curcuma xanthorrhiza: A Novel Type of Topical Anti-Inflammatory Agents: Structure-Activity Relationship

P. Claeson; U. Pongprayoon; T. Sematong; P. Tuchinda; V. Reutrakul; P. Soontornsaratune; W. C. Taylor

doi:10.1055/s-2006-957867

Planta Medica, Table of Contents

Planta Med 1996; 62(3): 236-240
DOI: 10.1055/s-2006-957867

Paper

Non-Phenolic Linear Diarylheptanoids from Curcuma xanthorrhiza: A Novel Type of Topical Anti-Inflammatory Agents: Structure-Activity Relationship

P. Claeson¹ ^, ² , U. Pongprayoon³ , T. Sematong³ , P. Tuchinda¹ , V. Reutrakul¹ , P. Soontornsaratune³ , W. C. Taylor⁴

¹Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
²Department of Pharmacognosy, Faculty of Pharmacy, Rangsit University, Paholyotin Road, Patumtani 12000, Thailand
³Pharmaceuticals and Natural Products Department, Thailand Institute of Scientific and Technological Research, 196 Paholyotin Road, Bangkok 10900, Thailand
⁴Department of Organic Chemistry, University of Sydney, N.S.W. 2006, Australia

Abstract

PDF Download

Abstract

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 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-diaryl-heptanoids are proposed to represent a novel class of topical anti-inflammatory agents.

Key words

Curcuma xanthorrhiza Roxb. - Zingiberaceae - diarylheptanoids - topical anti-inflammatory activity - structure-activity relationship

PDF (395 kb)