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

By Arnold Brossi and Matthew Suffness (Eds.)

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85 with a concomitant loss of an aminomethylene signal, suggesting the presence of a cyclic amide. Distinction between the placement of the carbonyl group at C-5’ or C-19’ was made by comparison of the ‘H-NMR spectrum of 14 with that of 19’-oxoleurosine (15) previously synthesized from leurosine (11) by oxidation with iodine under basic conditions (90). 66, permitting the placement of the carbonyl group of 14 at C-5‘. 5’-Oxoleurosine (14) was evaluated for antitumor activity according to established protocols.

The most productive line, MSC-B- 1, consisted of two distinctly different tissues, multiple shoots and unorganized tissue, and was maintained growing and productive for 30 months. Vinblastine (1)was isolated by HPLC, and the content was estimated to be 15 pg/g dry weight. Production of this alkaloid was greater than that in the callus culture but less than that observed for the parent plant, even though the levels of catharanthine (4) and vindoline (3) were about the same. C. CELLSUSPENSION STUDIES Studies using suspension cultures of C.

One significant difference from the ‘H-NMR spectrum of 1 is the much lower chemical shift for the C-21 methyl protons in the spectrum of vincovaline (28), which indicates the somewhat different environment for this group. The resistance of the C-4’ hydroxyl group to acetylation suggests that it may have the same configuration (p) as vinblastine (1). Comparison of the CD spectrum of 28 with those of various synthetic bisindole derivatives epimeric at stereo centers C-2’ and C- 18’ established the (2’S, 18’R) absolute configuration for the corresponding stereo centers of vincovaline (28).

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