Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L.
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.
Stevenson
Philip C
PC
Jodrell Laboratory, Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK. p.stevenson@kew.org <p.stevenson@kew.org>
Veitch
Nigel C
NC
Simmonds
Monique S J
MS
D000818:Animals; D001592:Benzyl Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D003510:Cyclohexanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005247:Feeding Behavior / Q000187:drug effects; D005960:Glucosides; D007814:Larva / Q000502:physiology; D010936:Plant Extracts / Q000737:chemistry; D027343:Rhizome / Q000737:chemistry; D018411:Spodoptera / Q000502:physiology; D030521:Zingiberaceae / Q000737:chemistry*
D001592:Benzyl Alcohols; D003510:Cyclohexanes; D005960:Glucosides; D010936:Plant Extracts; C005696:salicin