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

Mungkornasawakul, P; Pyne, SG; Jatisatienr, A; Supyen, D; Jatisatienr, C; Lie, W; Ung, AT; Skelton, BW; White, AH

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

Mungkornasawakul, P Pyne, SG Jatisatienr, A Supyen, D Jatisatienr, C Lie, W Ung, AT

Skelton, BW White, AH

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Publication Type:: Journal Article
Citation:: Journal of Natural Products, 2004, 67 (4), pp. 675 - 677
Issue Date:: 2004-04-01

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Field	Value	Language
dc.contributor.author	Mungkornasawakul, P	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Jatisatienr, A	en_US
dc.contributor.author	Supyen, D	en_US
dc.contributor.author	Jatisatienr, C	en_US
dc.contributor.author	Lie, W	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Skelton, BW	en_US
dc.contributor.author	White, AH	en_US
dc.date.issued	2004-04-01	en_US
dc.identifier.citation	Journal of Natural Products, 2004, 67 (4), pp. 675 - 677	en_US
dc.identifier.issn	0163-3864	en_US
dc.identifier.uri	http://hdl.handle.net/10453/8701
dc.description.abstract	A new pentacyclic Stemona alkaloid, stemocurtisinol (3), with a pyrido[1,2-α]azepine A,B-ring system, and the known pyrrolo[1,2-α ]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).	en_US
dc.relation.ispartof	Journal of Natural Products	en_US
dc.relation.isbasedon	10.1021/np034066u	en_US
dc.subject.classification	Medicinal & Biomolecular Chemistry	en_US
dc.subject.mesh	Animals	en_US
dc.subject.mesh	Anopheles	en_US
dc.subject.mesh	Stemonaceae	en_US
dc.subject.mesh	Alkaloids	en_US
dc.subject.mesh	Azepines	en_US
dc.subject.mesh	Furans	en_US
dc.subject.mesh	Crystallography, X-Ray	en_US
dc.subject.mesh	Inhibitory Concentration 50	en_US
dc.subject.mesh	Molecular Structure	en_US
dc.subject.mesh	Larva	en_US
dc.subject.mesh	Thailand	en_US
dc.title	Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-a]azepine Stemona Alkaloid	en_US
dc.type	Journal Article
utslib.citation.volume	4	en_US
utslib.citation.volume	67	en_US
utslib.for	0601 Biochemistry and Cell Biology	en_US
utslib.for	03 Chemical Sciences	en_US
utslib.for	06 Biological Sciences	en_US
utslib.for	11 Medical and Health Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	4	en_US
pubs.publication-status	Published	en_US
pubs.volume	67	en_US

Abstract:

A new pentacyclic Stemona alkaloid, stemocurtisinol (3), with a pyrido[1,2-α]azepine A,B-ring system, and the known pyrrolo[1,2-α ]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).

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http://hdl.handle.net/10453/8701