Phytochemical and larvicidal studies on Stemona curtisii: Structure of a new pyriodo[1,2-a]azepine Stemona alkaloid

Authors

Pitchaya Mungkornasawakul, Chiang Mai University
Stephen G. Pyne, University of WollongongFollow
Araya Jatisatienr, Chiang Mai University
Damrat Supyen, Chiang Mai University
Chaiwat Jatisatienr, Chiang Mai University
Wilford Lie, University of Wollongong
Alison T. Ung, University of Wollongong
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

11490

Publication Details

Mungkornasawakul, P., Pyne, S. G., Jatisatienr, A., Supyen, D., Jatisatienr, C., Lie, W., Ung, A. T., Skelton, B. W. & White, A. H. (2004). Phytochemical and larvicidal studies on Stemona curtisii: Structure of a new pyriodo[1,2-a]azepine Stemona alkaloid. Journal of Natural Products, 67 675-677.

Abstract

A new pentacyclic Stemona alkaloid, stemocurtisinol (3), with a pyrido[1,2-a]azepine A,B-ring system, and the known pyrrolo[1,2-a]azepine alkaloid oxyprotostemonine (4) have been isolated from a root extract of S. curtisii. The structure and relative stereochemistry of stemocurtisinol was determined by spectral data interpretation and X-ray crystallography. This compound is a diastereoisomer of oxystemokerrin and has the opposite configuration at C-4 and C-19. The individual alkaloid components showed significant larvicidal activity (IC₅₀ 4−39 ppm) on mosquito larvae (Anopheles minimus HO).