Microbial Transformation of Sampangine

Abstract

Microbial transformation studies of the antifungal alkaloid sampangine (2) have revealed that it is metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4'-O-methyl-beta-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the beta-glucopyranose conjugate (4). Metabolites 3 and 4 have been characterized on the basis of spectral data. Both 3 and 4 had significant in vitro activity against Cryptococcus neoformans but were inactive against Candida albicans. Metabolite 4 was inactive in vivo in a mouse model of cryptococcosis.

Microbial Transformation of Nitrogenous Compounds

“…The same research group previously (in 1999) reported microbial transformation studies of the antifungal alkaloid sampangine, which showed that the compounds can also be metabolized by a large number of microorganisms [59]. They utilized a standard two-stage fermentation technique; Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4 -O-methyl-β-glucopyranose conjugate, while Absidia glauca (ATCC 22752), C. elegans Scheme 7 Conversion of benzosampangine into the β-glucopyranose conjugate of benzosampangine utilizing different microorganisms [58] (ATCC 9245), Cunninghamella sp.…”

“…Both of them exhibited significant in vitro activity against Cryptococcus neoformans but did not show activity against Candida albicans. The β-glucopyranose conjugate was inactive in vivo in a mouse model of cryptococcosis [59]. …”

“…They utilized a standard two-stage fermentation technique; Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4 -O-methyl-β-glucopyranose conjugate, while Absidia glauca (ATCC 22752), C. elegans Scheme 7 Conversion of benzosampangine into the β-glucopyranose conjugate of benzosampangine utilizing different microorganisms [58] (ATCC 9245), Cunninghamella sp. (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the β-glucopyranose conjugate [59]. The structures of the related starting and transformed molecules are shown in Fig.…”

“…The metabolites 4 -O-methyl-β-glucopyranose and β-glucopyranose conjugates have been characterized on the basis of spectral data [59]. Both of them exhibited significant in vitro activity against Cryptococcus neoformans but did not show activity against Candida albicans.…”

Identification and Biological Activity of Microbial Metabolites of Xanthohumol

“…Culture and substrate controls were run simultaneously with the above experiments. 16) Microbial Transformation of Xanthohumol (1) by C. echinulata The filtrate of the combined fermentation broth was exhaustively extracted with EtOAc. On evaporation of the solvent a yellowish solid was obtained (500 mg).…”