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Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L.

Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L.

Stevenson, Philip C. ORCID: 0000-0002-0736-3619, 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 (doi:https://doi.org/10.1016/j.phytochem.2007.03.015)

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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.

Item Type: Article
Additional Information: Phytochemistry is an Official Journal of the Phytochemical Society of Europe and the Phytochemical Society of North America.
Uncontrolled Keywords: Kaempferia rotunda, Zingiberaceae, cyclohexane epoxides, zeylenol, salicin, Diels–Alder adduct
Subjects: Q Science > QD Chemistry
S Agriculture > SB Plant culture
Faculty / Department / Research Group: Faculty of Engineering & Science > Natural Resources Institute
Faculty of Engineering & Science > Natural Resources Institute > Agriculture, Health & Environment Department
Related URLs:
Last Modified: 11 Nov 2011 12:06
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/3369

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