Studies on the alkaloids of Thalictrum thunbergii DC. XVIII. Structure of thalictine, the tertiary base in the stems and leaves.

Chemical and Pharmaceutical Bulletin
1975.0

Abstract

The structure of thalictine (1), isolated from the stems and leaves of Thalictrum thunbergii DC., has been established as 1 by nuclear magnetic resonance (NMR) spectral data and chemical degradation. The molecular formula C₃₇H₄₀O₆N₂ of thalictine was determined by elemental analysis and mass spectrometry, indicating it is a bisbenzylisoquinoline (biscoclaurine) alkaloid. Chemical degradation methods including permanganate oxidation of O-ethylthalictine methyl methine (yielding 4-ethoxy-3,4'-oxydibenzoic acid, identified with an authentic sample) and sodium in liquid ammonia cleavage of O-ethylthalictine (yielding (S)-armepavine and (S)-O-ethylarmepavine) were employed. NMR spectral data revealed that thalictine is a 5–7' linked biscoclaurine alkaloid with a 21-membered heterocyclic ring, and its stereostructure was established as (S,S)-type. Mass spectral data and molecular models further supported the structure assignment. Thalictine is an additional example of 5-7' linked biscoclaurines and contains a cryptophenolic hydroxyl group in the benzyl moiety.

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