Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L.

Stevenson, Philip C., Veitch, Nigel C. and Simmonds, Monique S.J. (2007) Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L. Phytochemistry, 68 (11). pp. 1579-1586. ISSN 0031-9422

Abstract

Methanol extracts of Kaempferia rotunda L. rhizomes yielded seven compounds including six polyoxygenated cyclohexane derivatives identified as (−)-6-acetylzeylenol (1), four acylated derivatives of 1-benzoyloxymethyl-1,6-epoxycyclohexan-2,3,4,5-tetrol (3–6), a Diels–Alder adduct of 3-benzoyl-1-benzoyloxymethylcyclohexa-4,6-dien-2,3-diol (7), and a triacylated derivative of salicin (9). The cyclohexane diepoxide, crotepoxide (8), was also obtained. Spectroscopic methods were used for structure determination. The methanol extract of the rhizomes of K. rotunda and (−)-2-acetyl-4-benzoyl-1-benzoyloxymethyl-1,6-epoxycyclohexan-2,3,4,5-tetrol (2-acetylrotepoxide B; 6), had antifeedant activity against larvae of Spodoptera littoralis. (−)-Zeylenol (2) also showed antifeedant activity, whereas (−)-6-acetylzeylenol (1) was inactive.

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