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Planta Med 1992; 58(5): 449-453
DOI: 10.1055/s-2006-961511
Paper

© Georg Thieme Verlag Stuttgart · New York

Epimeric (20R,20S)-Verazine Isolated from Veratrum maackii: Two-Dimensional NMR Studies and Total Assignment of 1H- and 13C-Resonances

Xiuwen Han1 , Heinz Rüegger2 , 3
  • 1Dalian Institute of Chemical Physics, Chinese Academy of Science, Dalian, People's Republic of China
  • 2Spectrospin AG, Industriestraße 26, CII-8117 Fällanden, Switzerland
  • 3Laboratorium für Anorganische Chemie, Eidgenössische Technische Hochschule, CH-8092 Zürich, Switzerland
Further Information

Publication History

1991

Publication Date:
05 January 2007 (online)

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Abstract

13C-NMR evidence shows that verazine [(25S)-iminocholesta-5,22(N)-diene-3β-ol] isolated from the Chinese plant Veratrum maackii (Melanthiaceae) consists of a 20R/20S mixture of epimers. The determination of the configurations at the chiral epimeric center and of the conformation of the 17β-side chain is based on the total assignment of the 13C- and 1H-NMR resonances. This goal was achieved by the extensive use of homo- and heteronuclear shift correlation and two-dimensional NOE spectroscopy methods at high magnetic field.

Key words

Veratrum maackii - verazine - stereochemical elucidation - NMR spectroscopy