Structural investigations of the products of vincristine sulfate formed after in vitro incubation of the alkaloid in bile of dogs

  • Thimmaiah K
  • Sethi V
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Abstract

Vincristine (VCR) was incubated in bile from dogs at 37 °C for 72 h. At the end of the incubation, the mixture was extracted with methylene chloride. HPLC analysis (μBondapak C18, 10-μm, reverse-phase steel column; isocratic solvent system, 50% MeOH in 10 mM KH2PO4, pH 4.0; flow rate, 1.3 ml/min; detector, 254 nm) of the extract gave four peaks, A, B, C, and D with retention times of 3.8, 4.8, 7.0, and 21.9 min, respectively. In this system, VCR corresponded with peak C and its spectral properties were identical to those of the parent compound. The UV, IR, and MS spectral properties of these peaks were as follows [UV (λmax); IR (cm-1); MS ( m z)] peak A: 210, 250, 295 nm; 3424, 2919, 2850, 1738, 1680, 1601, 1461, 1382, 1231, 1032, 748; 783 (MH+); peak B: 210, 252, 295, 306 nm; 3465, 2919, 2851, 1739, 1679, 1599, 1034, 746; 825 (MH+); peak C: 220, 255, 295 nm; 3456, 2920, 2851, 1742, 1683, 1615, 1456, 1385, 734; 825 (MH+); peak D: 217, 252, 293, 312 nm; 3435, 2920, 2852, 1739, 1677, 1460, 1377, 1032, 726; 839 (MH+). These data suggest the following tentative structures: peak A, 4-deacetylvincristine; peak B, 4′-deoxy-3′-hydroxyvincristine; and peak D, 3′,4′-epoxyvincristine N-oxide. The structure of peak A as 4-deacetylvincristine was confirmed by chemical synthesis. © 1990.

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Authors

  • K. N. Thimmaiah

  • V. Sagar Sethi

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