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

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...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2004-04, Vol.67 (4), p.675-677
Hauptverfasser:	Mungkornasawakul, P, Pyne, S.G, Jatisatienr, A, Supyen, D, Jatisatienr, C, Lie, W, Ung, A.T, Skelton, B.W, White, A.H
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Anopheles - drug effects Azepines - chemistry Azepines - isolation & purification Azepines - pharmacology Biological and medical sciences Crystallography, X-Ray Fundamental and applied biological sciences. Psychology Furans - chemistry Furans - isolation & purification Furans - pharmacology Inhibitory Concentration 50 Larva - drug effects Medically important nuisances and vectors, pests of stored products and materials: population survey and control Molecular Structure Stemonaceae - chemistry Thailand Vectors. Intermediate hosts
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Zusammenfassung:	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 (IC(50) 4-39 ppm) on mosquito larvae (Anopheles minimus HO).
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np034066u