Issue 14, 1977

Biosynthesis of reticuline

Abstract

The incorporation of tyrosine, dopa, dopamine, and 4-hydroxy- and 3,4-dihydroxy-phenylpyruvic acids into reticuline in Litsea glutinosa has been studied, and it has been demonstrated that dopa and dopamine contribute only to the formation of the phenethylamine portion; the benzylic portion is biosynthesized from 3,4-dihydroxyphenylpyruvic acid not derived from dopa. Tyrosine and 4-hydroxy- and 3,4-dihydroxy-phenylpyruvic acids participate in the formation of both ‘halves’ of reticuline. Tracer experiments have shown the intermediacy of norlaudanosoline-1-carboxylic acid, norlaudanosoline, and didehydronorlaudanosoline in the biosynthesis of reticuline. Incorporation studies with (±)-4′-O-methylnorlaudanosoline, (±)-laudanosoline, (±)-6-O-methylnorlaudanosoline, and (±)-nor-reticuline have demonstrated that O-methylation prededes N-methylation and that there is no rigid selectivity of O-methylation in the biosynthesis of reticuline.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1977, 1662-1666

Biosynthesis of reticuline

D. S. Bhakuni, A. N. Singh, S. Tewari and R. S. Kapil, J. Chem. Soc., Perkin Trans. 1, 1977, 1662 DOI: 10.1039/P19770001662

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