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

By Arnold Brossi and Matthew Suffness (Eds.)

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90. 90 was assigned to the acetate at C-3 in the vindoline part, identical in chemical shift to the C-3 acetate in deacetoxyvinblastine acetate. 3). 48 assigned to 3'-H. From 26 GABOR B L A S K ~ A N D G E O F F R E Y C O R D E L L CO,CH, CH3 R1 R2 21 H OH 22 OH H these data, structure 21 was proposed for pseudovinblastinediol; however, based on the evidence available at present, the alternative structure 22 cannot be excluded from consideration. 18. Roseadine (23) The bioassay-guided fractionation of C.

The structure elucidation of 19 was further supported by 13C-NMRmeasurements (Table IX). 5 (C-19'). Such downfield shifts have been reported previously for the aminomethylene carbons in vincaleukoblastine ",-ox, 23 1. 2 53. 26 pg/ml) test systems in vitro (46). 16. Leurocolornbine (20) Leurocolornbine (20) was isolated from C. The mass spectrum of 20 indicated a molecular weight of 826, and high-resolution mass measurement verified the molecular formula C,,H,,N,O,,. Deuterium exchange in combination with mass spectrometry suggested that 20 contained one more exchangeable proton, most likely attached to an oxygen atom, than vinblastine (I), indicating that an additional hydroxyl group 24 GABORBLASKOANDGEOFFREYCORDELL ’3 20 was present in the molecule.

The configuration at C-4’ in leurocolombine (20) is considered to be the same as in vinblastine (1) in view of the similarity of the chemical shifts of the neighboring carbon atoms in 1 and 20; however, no configuration has yet been determined for C-2’. Leurocolombine (20) exhibited antimitotic activity and marginal antitumor activity against the Ridgeway osteogenic sarcoma (27% inhibition at 15 mg/kg) (44). 17. Pseudovinblastinediol (21) Pseudovinblastinediol (21) (formerly named pseudovincaleukoblastinediol) has been isolated from C.

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