Biosynthesis of thalicarpine

Bhakuni, Dewan S. ; Jain, Sudha (1982) Biosynthesis of thalicarpine Tetrahedron, 38 (5). pp. 729-732. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(82)80216-0

Abstract

The incorporation of (±)-, norlaudanosoline, -nor-reticuline, -N-methylcoclaurine and -norlaudanidine into thalicarpine in Cocculus laurifolius DC has been studied and specific utilization of (±)- reticuline is demonstrated. The evidence supports that both the "halves" of thalicapine are derived from reticuline. Parallel feedings of (S)-, and (R)-, reticulines showed that the stereospecifity is maintained in the biosynthesis of thalicarpine from the 1-benzyl-tetrahydroisoquinoline precursor. A double-labelling experiment with (±)-[1-3H, 4'-O14CH3] nor-reticuline has shown that the 4'---O---Me group of a nor-reticuline unit is lost in the biotransformation into thalicarpine. Feeding experiments also revealed that the plants can convert (S)-bolding and (S)-isoboldine into thalicarpine.

Item Type:Article
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ID Code:2305
Deposited On:07 Oct 2010 11:21
Last Modified:16 May 2011 07:28

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