Journal of the Chemical Society C Organic · 1966 · 20 citations · 0 references
Life SciencesBotanyPlant SciencesNatural Product BiosynthesisPlant BiochemistryPlant Molecular BiologyAlkaloid BiosynthesisPlant Natural Product BiosynthesisSecondary Metabolite BiosynthesisAbsolute Configuration AssignmentAbsolute Configuration DeterminationBiosynthetic Intermediates In Alkaloid PathwaysChemical DegradationChemical Degradation PathwaysPlant AlkaloidsQuinoline Alkaloid BiosynthesisTracer Experiments
A new bisbenzylisoquinoline alkaloid, stebisimine, has been isolated from Stephania japonica Miers and shown by physical methods and chemical degradation to be N-nor-1,2-dehydro-epistephanine. Tracer experiments have shown that half of the epistephanine molecule is derived exclusively from (–)-N-methylcoclaurine but not from its enantiomer. This confirms the absolute configuration of the alkaloid and shows that racemisation of the (+)-enantiomer is unimportant in this plant.