6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

•The first Stemona alkaloid with a seco-pyrido[1,2-a]azepine structure is reported.•The structure was elucidated using spectroscopic and X-ray crystallographic analysis.•Biosynthesis proposed by azepine ring cleavage of co-isolated stemocurtisine. A novel seco-stemocurtisine-type alkaloid, 6-hydroxy...

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Bibliographic Details
Published in:Phytochemistry letters 2013-11, Vol.6 (4), p.602-605
Main Authors: Mungkornasawakul, Pitchaya, Pyne, Stephen G., Willis, Anthony C., Jatisatienr, Arayar, Phuthsuk, Duang, Lie, Wilford
Format: Article
Language:English
Subjects:
aerial parts
alkaloids
nuclear magnetic resonance spectroscopy
Pyrido[1,2-a]azepine
Seco-alkaloid
Stemona
Stemona alkaloid
Stemona curtisii
X-ray diffraction
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Summary:•The first Stemona alkaloid with a seco-pyrido[1,2-a]azepine structure is reported.•The structure was elucidated using spectroscopic and X-ray crystallographic analysis.•Biosynthesis proposed by azepine ring cleavage of co-isolated stemocurtisine. A novel seco-stemocurtisine-type alkaloid, 6-hydroxy-5,6-seco-stemocurtisine was isolated from the aerial parts of Stemona curtisii (Stemonaceae) collected from Trang Province in Thailand. The unprecedented 5,6-seco-pyrido[1,2-a]azepine structure was elucidated by 2D NMR analysis and a single crystal X-ray crystallographic analysis.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2013.07.016