Autoxidation of the antimicrobial alkaloid cleistopholine in solution.
The alkaloid cleistopholine (3) undergoes rapid autoxidation in ethyl acetate solution under air giving rise to the corresponding N-oxide on one pathway, and to oxidation of the methyl group to a hydroxymethyl, formyl and further on to a carboxy group on the other one. Autoxidation can be suppressed by protection from light and air. In methanolic solution the extent of oxidation is less, in hydrochloric acid solution it is neglectable. The quinone moiety seems to be involved in the disposition to undergo oxidation.
Dombeck
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Department Pharmazie, Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Germany.
Bracher
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D000880:Anthraquinones / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004355:Drug Stability; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D019999:Pharmaceutical Solutions
D000880:Anthraquinones; D000890:Anti-Infective Agents; D001372:Aza Compounds; D007202:Indicators and Reagents; D019999:Pharmaceutical Solutions; C511287:cleistopholine