Randomisation and apparent regiospecificity in the incorporation of acetate into the monoterpenoid segment of the Corynanthe alkaloids
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 18,p. 1245-1246
- https://doi.org/10.1039/c39850001245
Abstract
Incorporation of 13C-enriched acetates into ajmalicine (3) by tissue cultures of Catharanthus roseus shows that, although administered [2-13C]-and [1,2-13C2]-acetates are extensively randomised prior to incorporation, the 16-, 17-, 18-, 19-, and 22-positions of monoterpene skeleton are selectively enriched as a result of equilibration of 13C enrichment in the intermediate 3-hydroxy-3-methylglutaryl (HMG) CoA pool; in contrast, DL-[2-13C]mevalonic acid was incorporated preferentially into dimethylailylpyrophosphate-derived unit of the monoterpene moiety.Keywords
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