Microbial transformation of papaveraldine.
Preparative-scale fermentation of papaveraldine (1), the known benzylisoquinoline alkaloid, with Mucor ramannianus 1839 (sih) has resulted in a stereoselective reduction of the ketone group and the isolation of S-papaverinol (2) and S-papaverinol N-oxide (3). The structure elucidation of both metabolites was based primarily on 1D-, 2D-NMR analyses and chemical transformations. The absolute configuration of 2 was determined using Horeau's method of asymmetric esterification. These metabolism results were consistent with the previous plant cell transformation studies on papaverine and isopapaverine.
El Sayed
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Medicinal, Aromatic and Poisonous Plants Research Center, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. abdelaty@ksu.edu.sa
D003497:Cyclic N-Oxides / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D009089:Mucor / Q000378:metabolism*; D010084:Oxidation-Reduction; D010208:Papaverine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism
D003497:Cyclic N-Oxides; C411339:papaverinol N-oxide; C039657:papaverinol; D010208:Papaverine; C039655:papaveraldine