Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-α]azepine Stemona alkaloid

P. Mungkornasawakul; S.G. Pyne; A. Jatisatienr; D. Supyen; C. Jatisatienr; W. Lie; A.T. Ung; Brian Skelton; Allan White

doi:10.1021/np034066u

Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-α]azepine Stemona alkaloid

P. Mungkornasawakul
, S.G. Pyne
, A. Jatisatienr
, D. Supyen
, C. Jatisatienr
, W. Lie
, A.T. Ung
, Brian Skelton
, Allan White

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

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).

Original language	English
Pages (from-to)	675-677
Journal	Journal of Natural Products
Volume	67
Issue number	4
DOIs	https://doi.org/10.1021/np034066u
Publication status	Published - 2004

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title = "Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-α]azepine Stemona alkaloid",

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).",

author = "P. Mungkornasawakul and S.G. Pyne and A. Jatisatienr and D. Supyen and C. Jatisatienr and W. Lie and A.T. Ung and Brian Skelton and Allan White",

year = "2004",

doi = "10.1021/np034066u",

language = "English",

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pages = "675--677",

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T1 - Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-α]azepine Stemona alkaloid

AU - Mungkornasawakul, P.

AU - Pyne, S.G.

AU - Jatisatienr, A.

AU - Supyen, D.

AU - Jatisatienr, C.

AU - Lie, W.

AU - Ung, A.T.

AU - Skelton, Brian

AU - White, Allan

PY - 2004

Y1 - 2004

N2 - 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).

AB - 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).

U2 - 10.1021/np034066u

DO - 10.1021/np034066u

M3 - Article

C2 - 15104502

SN - 0163-3864

VL - 67

SP - 675

EP - 677

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-α]azepine Stemona alkaloid

Abstract

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