By Arnold Brossi and Matthew Suffness (Eds.)
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Extra info for Antitumor Bisindole Alkaloids from (L.)
The inferences of these results for the formation of the bisindoles where both monomeric structural elements are defacto required are clear. Miura and co-workers (121) have successfully induced multiple shoot cultures of C. O mg/liter of the cytokinin benzyladenine. 37 mg/g dry weight, respectively in the leaf tissue. In the case of catharanthine (4) this represented a 10-fold increase over the parent plant tissue, and such levels were sustained in the regenerated plants. 1 mg/g dry weight, respectively.
The methanol extract of the same culture afforded sitsirikine (48), isositsirikine (58), dihydrositsirikine (59), yohimbine (60), 3-iso-19-epiajmalicine (61), pleiocarpamine ( 5 3 , and antirhine (62) (130). Pitiard et af. (131,132)found a strain which produced over 50 alkaloids as detected by TLC, and 13 of these were identified (Table XIII), including 3 new to C. roseus, 3-epiajmalicine (63), deacetylakuammiline (64), and dihydrocondylocarpine (65), and 3 new natural products, 7-hydroxyindolenine ajmalicine (66), pseudoindoxyl ajmalicine (67), and 10-hydroxy-deacetylakuammiline (68).
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. According to the 13C-NMR spectrum of 32 (Table XII) the molecule is not symmetrical in space, based on the observed conformationally induced interaction between the two units, which causes some carbons to be shifted downfield while others are shifted upfield.
Antitumor Bisindole Alkaloids from (L.) by Arnold Brossi and Matthew Suffness (Eds.)