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

HETEROCYCLES
1986.0

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-methoxytabersonine → 16-methoxy-2,3-dihydro-3-hydroxytabersonine → 16-methoxy-2,3-dihydro-3-hydroxy-N(1)-methyltabersonine (i.e. desacetoxyvindoline) → deacetylvindoline → vindoline. © 1986.

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