Issue 6, 1978

Biosynthesis of the abnormal Erythrina alkaloids, cocculidine and cocculine

Abstract

The incorporation of (±)-N-norprotosinomenine, (±)-N-nororientaline, (±)-N-nor-reticuline, (±)-norlaudanosoline, (±)-protosinomenine, and N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-2-(4-hydroxyphenyl)ethylamine into cocculidine has been studied, and the specific utilization of the (±)-N-norprotosinomenine demonstrated. A double labelling experiment with (±)-[1-3H, 4′-methoxy-14C]-N-norprotosinomenine showed that the 4′-O-methyl group of the precursor is retained in the bioconversion and the erythrinan ring system is not formed by addition of the secondary amino function onto an ortho-quinone system. Parallel experiments with (+)- and (–)-N-norprotosinomenine demonstrated specific incorporation of the (+)-isomer into cocculidine. High incorporation of cocculidine into cocculine revealed that O-demethylation is the terminal step in the biosynthesis of the latter. Feeding experiments also revealed that the plants can convert isococculidine into cocculidine with very high efficiency.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 618-622

Biosynthesis of the abnormal Erythrina alkaloids, cocculidine and cocculine

D. S. Bhakuni and A. N. Singh, J. Chem. Soc., Perkin Trans. 1, 1978, 618 DOI: 10.1039/P19780000618

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