Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine

Bhakuni, Dewan S. ; Jain, Sudha ; Singh, Awadhesh N. (1980) Biosynthesis of the bisbenzylisoquinoline alkaloid, tetrandrine Phytochemistry, 19 (11). pp. 2347-2350. ISSN 0031-9422

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The incorporation of (±)-coclaurine, (±)-norcoclaurine, (±)-N-methylcoclaurine and didehydro-N-methyleoclaurinium iodide into tetrandrine in Cocculus laurifolius has been studied and specific utilization of (±)-N-ethylcoclaurine demonstrated. The evidence indicates that tetrandrine is formed in the plants by oxidative dimerization of N-methylcoclaurine. Double labelling experiment 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 tetrandrine. Parallel feedings of (+)-(S)- and (-)-(R)-N-methylcoclaurines showed that the stereospecificity is maintained in the biosynthesis of tetrandrine from the 1-benzylisoquinoline precursor.

Item Type:Article
Source:Copyright of this article belongs to Phytochemical Society of Europe.
Keywords:Cocculus laurifolius; Menispermaceae; Biosynthesis; Tetrandrine: (±)-N-Methyleoclaurine
ID Code:2297
Deposited On:07 Oct 2010 11:22
Last Modified:16 May 2011 07:37

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