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Applied and Environmental Microbiology, September 2000, p. 3850-3855, Vol. 66, No. 9
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.

Biotransformation of the Antimelanoma Agent Betulinic Acid by Bacillus megaterium ATCC 13368

Parnali Chatterjee,1 Samir A. Kouzi,2,* John M. Pezzuto,3 and Mark T. Hamann4

Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, Louisiana 712091; Department of Pharmaceutics and Medical Chemistry, School of Pharmacy, University of the Pacific, Stockton, California 952112; Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 606123; and Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, Mississippi 386774

Received 6 March 2000/Accepted 5 June 2000

Microbial transformation of the antimelanoma agent betulinic acid was studied. The main objective of this study was to utilize microorganisms as in vitro models to predict and prepare potential mammalian metabolites of this compound. Preparative-scale biotransformation with resting-cell suspensions of Bacillus megaterium ATCC 13368 resulted in the production of four metabolites, which were identified as 3-oxo-lup-20(29)-en-28-oic acid, 3-oxo-11alpha -hydroxy-lup-20(29)-en-28-oic acid, 1beta -hydroxy-3-oxo-lup-20(29)-en-28-oic acid, and 3beta ,7beta ,15alpha -trihydroxy-lup-20(29)-en-28-oic acid based on nuclear magnetic resonance and high-resolution mass spectral analyses. In addition, the antimelanoma activities of these metabolites were evaluated with two human melanoma cell lines, Mel-1 (lymph node) and Mel-2 (pleural fluid).

* Corresponding author. Mailing address: School of Pharmacy, University of the Pacific, Stockton, CA 95211.. Phone: (209) 946-2420. Fax: (209) 946-2410. E-mail: skouzi{at}uop.edu.

Applied and Environmental Microbiology, September 2000, p. 3850-3855, Vol. 66, No. 9
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.




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