Biosynthesis of bisbenzylisoquinoline alkaloids in cultured roots of Stephania cepharantha.

Cultured roots of Stephania cepharantha, which are rich sources of bisbenzylisoquinoline alkaloids, were fed 14C-labelled tyrosine, tyramine or dopamine. While tyrosine was well incorporated into the bisbenzylisoquinolines, tyramine and dopamine were poorly incorporated. Incorporated tyrosine was shown to be decarboxylated and stored as tyramine in the roots, then gradually converted to the bisbenzylisoquinolines. Tracer experiments using [3-13C]tyrosine demonstrated that tyrosine was specifically incorporated into the corresponding sites of aromoline, which verified that aromoline was composed of four molecules of tyrosine. The ratio of 13C-enrichments of C-4 and C-alpha in (R) and (S) halves of aromoline was the same within experimental limits. This indicated that the two coclaurine units must have one and the same biogenetic origin.