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Planta Med 1993; 59(5): 467-470
DOI: 10.1055/s-2006-959735
Paper

© Georg Thieme Verlag Stuttgart · New York

Revised Stereochemistry of So-Called Isoselagine and Spectroscopic Analysis of 6α-Hydroxylycopodine from Lycopodium serratum var. longipetiolatum

Chang-Ming Sun1 , Li-Kang Ho2 , Mei-Ling Sun1
  • 1National Research Institute of Chinese Medicine, Taipei Hsien, 231 Taiwan, Republic of China
  • 2Department of Pharmacology, National Yang-Ming Medical College, Taipei 112, Taiwan, Republic of China
Further Information

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

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