The biosynthesis of the alkaloids of croton sparsiflorus morong

Bhakuni, Dewan S. ; Jain, Sudha (1981) The biosynthesis of the alkaloids of croton sparsiflorus morong Tetrahedron, 37 (18). pp. 3175-3181. ISSN 0040-4020

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Incorporation of tyrosine, dopa, dopamine, 4-hydroxyphenylpyruvic acid, (±)-, norcoclaurine-1-carboxylic acid, -norcoclaurine, -coclaurine, and -N-methylcoclaurine into N-methylcrotsparine, N-methylcrotsparinine and N-methylsparsiflorine in Croton sparsiflorus Morong has been studied. The evidence supports the direct oxidative coupling of (+)-, and (-)-N-methylcoclaurines to give N-methylcrotsparine and N-methylcrotsparinine respectively. Tracer experiment show that N-methylcrotsparine undergoes dienone-phenol rearrangement to give N-methylsparsiflorine. A double labelling experiment with (±)-N[14C]methyl[1-3H]coclaurine demonstrated that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion. The intermediacy of norcoclaurine-1-carboxylic acid and specific incorporation of dehydro-N-methylcoclaurinium salt into the bases have been demonstrated.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:2273
Deposited On:07 Oct 2010 11:39
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