Characterization of the products of vinblastine dihydrogen sulfate formed after invitro incubation in bile

Thimmaiah, K. N. and Sethi, V. S. (1990) Characterization of the products of vinblastine dihydrogen sulfate formed after invitro incubation in bile. Microchemical Journal, 41 (3). pp. 313-319.

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Abstract

Vinblastine (VLB) was incubated in bile from a dog at 37 °C for 72 h. The reaction mixture was extracted with methylene chloride and the extract gave four major peaks (A, B, C, and D) with retention times of 4.0, 6.5, 9.8, and 28.0 min, respectively, in an HPLC system (μBondapak C18 column; solvent, 50% MeOH in 10 mM KH2PO4, pH 4.0; flow rate, 1.3 ml/min; detector, 254 nm). In the HPLC system, VLB corresponded with peak C and its spectral properties were identical to the parent compound. The UV, IR, and MS data of these peaks were as follows [UV (λmax); IR (cm−1); MS ()]: peak A: 212, 252, 295 nm; 3363, 2922, 2850, 1734, 1611, 1455, 1373, 1235, 1036, 745; 769 (MH+); peak B: 210, 253, 282, 302 nm; 3421, 2922, 2850, 1734, 1452, 1369, 1040, 740; 809 (MH+); peak C: 214, 255, 280, 290 nm; 3468, 2919, 2851, 1742, 1461, 1373, 1041, 745; 811 (MH+); peak D: 208, 255, 288, 312 nm; 3570, 2919, 2850, 1739, 1464, 1383, 1036, 725; 825 (MH+). The following tentative structures for the products are proposed: peak A, 4-deacetylvinblastine; peak B, 3′,4′-anhydrovinblastine N-oxide; and peak D, 19′-oxovinblastine. The structure of peak A as 4-deacetylvinblastine was confirmed by chemical synthesis.

Item Type:	Article
Uncontrolled Keywords:	Chemistry, Analytical
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Dr Raju C
Date Deposited:	21 Jan 2021 09:47
Last Modified:	25 Jan 2021 05:56
URI:	http://eprints.uni-mysore.ac.in/id/eprint/15372

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