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

Thimmaiah, K. N. and Sethi, V. S. (1990) Structural investigations of the products of vincristine sulfate formed after invitro incubation of the alkaloid in bile of dogs. Microchemical Journal, 41 (3). pp. 320-326.

Text savedrecs(57).bib Download (1kB)

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 ()] 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.

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Dr Raju C
Date Deposited:	21 Jan 2021 10:00
Last Modified:	27 Jan 2021 10:07
URI:	http://eprints.uni-mysore.ac.in/id/eprint/15373

Actions (login required)

View Item