Biosynthesis of the bisbenzylisoquinoline alkaloid cocsulin

Bhakuni, Dewan S. ; Labroo, Virender M. ; Singh, Awadhesh N. ; Kapil, Randhir S. (1978) Biosynthesis of the bisbenzylisoquinoline alkaloid cocsulin Journal of Chemical Soceity, Perkin Transactions 1 . pp. 121-125. ISSN 0300-922X

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The incorporation of (±)-coclaurine, (±)-norcoclaurine, (±)-N-methylcoclaurine, and didehydro-N-methylcoclaurinium iodide into cocsulin in Cocculus laurifolius DC has been studied, and specific utilization of the (±)-N-methylcoclaurine demonstrated. The evidence supports the occurrence of oxidative dimerization of two N-methylcoclaurine units to give cocsulin. Double labelling experiments with (±)-N-methyl[1-3H, methoxy-14C]coclaurine showed that the O-methyl function from one of the N-methylcoclaurine units is lost in the bioconversion into cocsulin. Experiments with (±)-N-[14C]methyl[1-3H]coclaurine demonstrated that the hydrogen atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into cocsulin. Parallel feedings of (+)-(S)- and (-)-(R)-N-methylcoclaurines showed that the stereospecificity is maintained in the biosynthesis of cocsulin from the 1-benzylisoquinoline precursor.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:2357
Deposited On:07 Oct 2010 09:09
Last Modified:16 May 2011 07:43

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