Glucohaplopine — A new glycoalkaloid fromHaplophyllum perforatum

Chemistry of Natural Compounds
1979.0

Abstract

Two studies on alkaloids are presented. First, continuing the separation of chloroform-soluble alkaloids from Haplophyllum perforatum, a new glycoalkaloid glucohaplopine (I, C₁₉H₂₁NO₉) was isolated. Its structure was elucidated as 7-β-D-glucopyranosyloxy-4,8-dimethoxyfuroquinoline based on UV, IR, mass spectrometry, acetylation (forming a tetraacetyl derivative), enzymatic hydrolysis (yielding haplopine and D-glucose), and Klyne's rule (confirming β-glucosidic bond). Second, continuing the separation of alkaloids from Fumaria vaillantii, cheilanthifoline, parfumine, and d-stylopine were isolated (identified by comparison with authentic samples), along with a new base norjuziphine (II, C₂₀H₂₀NO₄). Its structure was determined as the N-demethyl derivative of juziphine via UV, IR, NMR, mass spectrometry, and methylation (yielding juziphine, confirmed by TLC and mixed melting point).

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