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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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00319...
Related URL: http://dx.doi.org/10.1016/S0031-9422(00)91024-0
Abstract
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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