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Communication | Regular issue | Vol 24, No. 9, 1986, pp.2415-2421
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2415
Altered Alkaloid Pattern in Dark Grown Seedlings of Catharanthus roseus. The Isolation and Characterization of 4-Desacetoxyvindoline: A Novel Indole Alkaloid and Proposed Precursor of Vindoline

John Balsevich,* Vincenzo DeLuca, and Wolf G. W. Kurz

*Plant Biothchnology Institute, National Research Council of Canada, Saskatoon, Saskatchewan, S7N, OW9, Canada

Abstract

Seeds of Catharanthus roseus cv. Little Delicata were germinated in the dark which resulted in relatively high and even rates of germination. Analysis of alkaloids from the cotyledons of 6 - 9 day old dark grown seedlings led to the identification of tabersonine, 16-methoxytabersonine, and catharanthine as relatively major components while vindoline, deacetylvindoline, 4-desacetoxyvindoline and 16-hydroxytabersonine were identified as minor components. Subjecting dark grown seedlings to light led to a rapid increase in the amount of vindoline present with a concomitant decrease in the amounts of tabersonine, 16-methoxytabersonine and the minor components. The amount of catharanthine present was not greatly affected. These observations suggested that the biosynthetic pathway between tabersonine and vindoline proceeds as follows: 16-hydroxytabersonine → 16-rnethoxytabersonine → 16-methoxy-2,3-dihydro-3-hydroxytabersonine → 16-methoxy-2,3-dihydro-3-hydroxy-N(1)-methyltabersonine (i .e. desacetoxyvindoline) → deacetylvindoline → vindoline.
+ The numbering system used was as for aspidospermidine in Chemical Abstracts.