Issue 11, 1978
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Biosynthesis of oxyacanthine

Dewan S. Bhakuni,   Awadhesh N. Singh  and  Sudha Jain  

Abstract

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.

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Article information

DOI
https://doi.org/10.1039/P19780001318
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 1318-1321

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Biosynthesis of oxyacanthine

D. S. Bhakuni, A. N. Singh and S. Jain, J. Chem. Soc., Perkin Trans. 1, 1978, 1318 DOI: 10.1039/P19780001318

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