Biosynthesis of oxyacanthine

Bhakuni, Dewan S. ; Singh, Awadhesh N. ; Jain, Sudha (1978) Biosynthesis of oxyacanthine Journal of Chemical Soceity Perkin Transactions 1 . pp. 1318-1321. ISSN 0300-922X

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The incorporation of (±)-norcoclaurine, (±)-coclaurine, (±)-N-methylcoclaurine, didehydro-N-methylco-claurinium iodide, (+)-(S)-N-methylcoclaurine and (-)-(R)-N-methylcoclaurine into oxyacanthine in Cocculus laurifolius DC has been studied and specific utilization of (±)-N-methylcoclaurine, (+)-(S)-N-methylcoclaurine, (-)-(R)-N-methylcoclaurine, and didehydro-N-methylcoclaurinium iodide demonstrated. The evidence supports intermolecular oxidative coupling of (+)-(S)-N-methylcoclaurine and (-)-(R)-N-methylcoclaurine to give oxyacanthine. A double labelling experiment with (±)-[1-3H,N-14CH3]-N-methylcoclaurine demonstrated that the hydrogen atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into oxyacanthine.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:2353
Deposited On:07 Oct 2010 09:11
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