Antitumor Bisindole Alkaloids from (L.) by Arnold Brossi and Matthew Suffness (Eds.)

By Arnold Brossi and Matthew Suffness (Eds.)

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STRUCTURE AND BIOSYNTHESIS OF BISINDOLES 39 was found in the roots at the start of flowering, and the minimum in the stems during the full fruiting stage. The rate of alkaloid accumulation decreased during fruit maturation, and the most active stage of alkaloid biosynthesis was at the start of flowering in all vegetative organs. This is in accord with previous studies (106) where a higher level of vinblastine (1) was reported in extracts of leaves of young C. roseus plants than in those of older plants.

Vindolicine (32) Vindolicine (32) is an unusual alkaloid, isolated from C. roseus (29,53), whose structure reflects the joining of two vindoline units through con- 32 I . STRUCTURE AND BIOSYNTHESIS OF BlSlNDOLES 35 densation with a one-carbon fragment. Although there are other bisindole alkaloids known to be formed by the union of two Aspidosperma units ( 3 ) ,vindolicine (32)is the only example linked in the above manner. The structure of 32 was confirmed by UV, IR, 'H-, and I3C-NMR measurements.

48%) was strictosidine lactam (41), which is not normally seen in extracts of intact plants. Variation of the pH and added phytohormones did not significantly alter the pattern of alkaloids produced by this cell line (160). Further cell line studies (161) afforded one line (176G) which produced mainly ajmalicine (39) and lochnericine (73) and one (299’11)which apparently contained relatively inactive p-glucosidases, since the major alkaloids produced were strictosidine (33) (83%) and strictosidine lactam (41) (Table XIII).

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