Three Non-Phenolic Diarylheptanoids with Anti-Inflammatory Activity from Curcuma xanthorrhiza

P. Claeson; A. Panthong; P. Tuchinda; V. Reutrakul; D. Kanjanapothi; W. C. Taylor; T. Santisuk

doi:10.1055/s-2006-959730

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Planta Med 1993; 59(5): 451-454
DOI: 10.1055/s-2006-959730

Paper

Three Non-Phenolic Diarylheptanoids with Anti-Inflammatory Activity from Curcuma xanthorrhiza

P. Claeson¹ , A. Panthong² , P. Tuchinda¹ , V. Reutrakul¹ , D. Kanjanapothi² , W. C. Taylor³ , T. Santisuk⁴

¹Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
²Department of Pharmacology, Faculty of Medicine, Chiang Mai University, Chiang Mai 50002, Thailand
³Department of Organic Chemistry, University of Sydney, N.S.W. 2006, Australia
⁴The Forest Herbarium, Royal Forestry Department, Bangkok 10900, Thailand

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1992

1993

Publication Date:
04 January 2007 (online)

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Abstract

Bioassay-guided fractionation of a hexane extract of the rhizomes of Curcuma xanthorrhiza Roxb. (Zingiberaceae) led to the isolation of three non-phenolic diarylheptanoids, identified mainly by high-field ¹H-NMR as trans-trans-1,7-diphenyl-1,3-heptadien-4-one (alnustone), trans-1,7-diprienyl-1-hepten-5-ol, and trans,trans-1,7-diphenyl-1,3-heptadien-5-ol. The latter is reported for the first time as a plant constituent. Germacrone, curzerenone, and cinnamaldehyde were also isolated and identified. The three diarylheptanoids all exerted significant anti-inflammatory activity in the assay of carrageenin-induced hind paw edema in rats.

Key words

Curcuma xanthorrhiza - Zingiberaceae - medicinal plant - diarylheptanoids - NMR - anti-inflammatory activity