Biosynthesis of cocsulinin

Bhakuni, Dewan S. ; Jain, Sudha ; Singh, Awadhesh N. (1978) Biosynthesis of cocsulinin Journal of Chemical Soceity, Perkin Transactions 1 . pp. 380-383. 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/P19780000380

Abstract

The incorporation of (±)-norcoclaurine, (±)-coclaurine, and (±)-N-methylcoclaurine into cocsulinin in Cocculus laurifolius DC has been studied, and specific utilization of the (±)-N-methylcoclaurine has been demonstrated. The evidence supports oxidative dimerisation of two N-methylcoclaurine units to give cocsulinin. Experiments with (±)-N-[14C]methyl[1-3H]coclaurine have demonstrated that the hydrogen atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into cocsulinin. Parallel feedings of (+)-(S)- and (-)-(R)-N-methylcoclaurines showed that the configuration at C-1 is maintained in the biosynthesis of cocsulinin from the 1-benzylisoquinoline precursor.A double-labelling experiment with (±)-N-methyl[1-3H, 6-O-methyl-14C]coclaurine has shown that the 6-O-methyl group of an N-methylcoclaurine unit is lost in the biotransformation into cocsulinin. Incorporation of (+)-(S,S)-O-methylcocsulinin established that de-O-methylation is the terminal step in the biosynthesis of cocsulinin.

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