Biosynthesis of the abnormal Erythrina alkaloids, cocculidine and cocculine

Bhakuni, Dewan S. ; Singh, Awadhesh N. (1978) Biosynthesis of the abnormal Erythrina alkaloids, cocculidine and cocculine Journal of Chemical Soceity, Perkin Transactions 1 . pp. 618-622. ISSN 0300-922X

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Official URL: http://www.rsc.org/publishing/journals/P1/article....

Related URL: http://dx.doi.org/10.1039/P19780000618

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.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:2356
Deposited On:07 Oct 2010 09:10
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