Glucosidation of betulinic acid by Cunninghamella species.
Microbial transformation of the antimelanoma agent betulinic acid (1) was studied. Preparative scale biotransformation with resting-cell suspensions of Cunninghamella species NRRL 5695 resulted in the production of a fungal metabolite of 1, which has been characterized as 28-O-beta-D-glucopyranosyl 3beta-hydroxy-lup-20(29)-en-28-oate (2) based on spectral and enzymic data. The in vitro cytotoxicity assay of metabolite 2 revealed no activity against several human melanoma cell lines.
Chatterjee
P
P
Division of Basic Pharmaceutical Sciences, School of Pharmacy, Northeast Louisiana University, Monroe, Louisiana 71209, USA.
Pezzuto
J M
JM
Kouzi
S A
SA
D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D001711:Biotransformation; D002470:Cell Survival / Q000187:drug effects; D020093:Cunninghamella / Q000378:metabolism*; D004354:Drug Screening Assays, Antitumor; D005285:Fermentation; D005960:Glucosides / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D008545:Melanoma / Q000473:pathology; D053978:Pentacyclic Triterpenes; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014315:Triterpenes / Q000378:metabolism* / Q000494:pharmacology; D014407:Tumor Cells, Cultured; D000094062:Betulinic Acid
D000972:Antineoplastic Agents, Phytogenic; D005960:Glucosides; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid