Transformation of 2,2′-Bimorphine to the Novel Compounds 10-α- S -Monohydroxy-2,2′-Bimorphine and 10,10′-α,α′- S , S ′-Dihydroxy-2,2′-Bimorphine by Cylindrocarpon didymum

Abstract

Whole-cell suspensions of Cylindrocarpon didymum were observed to transform 2,2′-bimorphine to the compounds 10-α-S-monohydroxy-2,2′-bimorphine and 10,10′-α,α′-S,S′-dihydroxy-2,2′-bimorphine. Mass spectrometry and 1H nuclear magnetic resonance spectroscopy confirmed the identities of these new morphine alkaloids.

Microbial Transformation of Nitrogenous Compounds

“…The same 2,2 -bimorphine has been further transformed into 10-α-S-monohydroxy-2,2 -bimorphine and 10,10 -α,α -S,S -dihydroxy-2,2 -bimorphine by the same group of researchers, again utilizing C. didymum whole-cell suspensions [50]. These compounds were confirmed using classical spectroscopic …”

“…Steps involved in the transformation of 2,2 -bimorphine to 10-α-S-monohydroxy-2,2 -bimorphine and 10,10 -α,α -S,S -dihydroxy-2,2 -bimorphine in the presence of Cylindrocarpon didymum [50] Preparative-scale fermentation of papaveraldine, the known benzylisoquinoline alkaloid, with Mucor ramannianus 1839 (sih) has resulted in a stereoselective reduction of the ketone group and the isolation of Spapaverinol and S-papaverinol N-oxide [56]. The structure elucidations of both metabolites were reported to be based primarily on 1D and 2D NMR analyses and chemical transformations [56].…”

“…Berberine and sanguinarine are used as antimicrobials and others as muscle relaxants, such as parpaverine and (+)-tubocurarine [2]. The morphine alkaloids are the major alkaloid components of the opium poppy, Papaver somniferum, and these compounds still provide some of the most potent analgesic compounds in clinical use [50]. Many synthetic derivatives of morphine have been reported, and subtle changes in functionality can significantly alter the pharmacological activity of these compounds [50].…”

“…The morphine alkaloids are the major alkaloid components of the opium poppy, Papaver somniferum, and these compounds still provide some of the most potent analgesic compounds in clinical use [50]. Many synthetic derivatives of morphine have been reported, and subtle changes in functionality can significantly alter the pharmacological activity of these compounds [50]. The microbial transformations of morphine alkaloids have been investigated as a means of producing opiates and pivotal intermediates that are difficult to produce by chemical synthesis [50].…”

“…Many synthetic derivatives of morphine have been reported, and subtle changes in functionality can significantly alter the pharmacological activity of these compounds [50]. The microbial transformations of morphine alkaloids have been investigated as a means of producing opiates and pivotal intermediates that are difficult to produce by chemical synthesis [50].…”