1983•Helvetica Chimica ActaRequires access

Biosynthesis of Benzo[c]phenanthridine Alkaloids Sanguinarine, Chelirubine and Macarpine

Narao Takao, M. Kamigauchi, Momoyo Okada

Abstract

Abstract The biosynthesis of the benzo[c]phenanthridine alkaloids was investigated in a cell suspension culture of Macleaya cordata (papaveraceae). Feeding experiments define the biosynthetic pathway (–)‐7,8,13,13a‐tetrahydrocoptisine →(–)‐cis‐N‐methyl‐7,8,13,13a‐tetrahydrocoptisinium salt 15→ protopine (5)→ sanguinarine (1)→ chelirubine (3)→ macarpine (4).

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Key concepts: Sanguinarine, Phenanthridine, Protopine, Chemistry, Papaveraceae, Biosynthesis, Alkaloid, Stereochemistry