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DOI: 10.1055/s-2006-959735
© Georg Thieme Verlag Stuttgart · New York
Revised Stereochemistry of So-Called Isoselagine and Spectroscopic Analysis of 6α-Hydroxylycopodine from Lycopodium serratum var. longipetiolatum
Publication History
1992
1993
Publication Date:
04 January 2007 (online)
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Abstract
The structure of isoselagine, isolated from the Chinese medicinal plant Lycopodium serratum Thunb. var. longipetiolatum Spring, was shown to be identical with huperzine A (1) and to have an exocyclic double bond in the E -configuration from NOE data. In the process of extraction of isoselagine, we also isolated and identified another alkaloid, 6α-hydroxylycopodine (L. 20) (2) that was found to occur in this plant for the first time. The structure of L. 20 was previously determined mainly by the chemical means, and this is the first report on the analysis of its structure by 1H- and 13C-NMR with more advanced 2D-NMR techniques. The X-ray crystallography revealed the stereochemistry of 2 and confirmed its structure. The hemostatic properties of the isolated alkaloids were studied, but they showed no platelet aggregation activity.
Key words
Lycopodium serratum Thunb var. longipetiolatum Spring - isoselagine - huperzine A - 6α-hy-droxylycopodine - stereochemistry - NMR-assignments - X-ray analysis