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Planta Med 2004; 70(7): 637-641
DOI: 10.1055/s-2004-827187
Original Paper
Biochemistry and Molecular Biology
© Georg Thieme Verlag KG Stuttgart · New York

Microbial Metabolism of Pseudoprotodioscin

Mei Dong1 , 4 , Xizhi Feng2 , 4 , Ben-Xiang Wang3 , Takashi Ikejima3 , Li-Jun Wu4
  • 1Department of Cell Biology, Neurobiology, and Anatomy, University of Cincinnati, Cincinnati, Ohio, USA
  • 2Department of Chemistry, University of Virginia, Charlottesville, Virginia, USA
  • 3Research Center of New Drugs, Changchun College of Traditional Chinese Medicine, Changchun, P. R. China
  • 4Department of Natural Medicinal Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China
Further Information

Publication History

Received: October 17, 2003

Accepted: April 12, 2004

Publication Date:
15 July 2004 (online)

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Abstract

Microbial transformation of the furostanol saponin pseudoprotodioscin (1) using Aspergillus fumigatus resulted in the isolation of two new steroidal metabolites, 3-O-[bis-α-L-rhamnopyranosyl-(1→2 and 1→4)-β-D-glucopyranosyl]-22R,25R-spirost-5-ene-3β,20α-diol (2) and 3-O-[bis-α-L-rhamnopyranosyl-(1→2 and 1→4)-β-D-glucopyranosyl]-25R-furost-5-ene-3β,22α,26-triol (3), in addition to the previously reported steroidal saponins: dioscin (4) and progenin II (5). The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. Metabolites 2 - 5 showed significant cytotoxicity against cancer cell lines A375, L929, and HeLa with IC50 values ranging from 1.18 μM to 17.88 μM.

Key words

Dioscorea panthaica - Dioscoreaceae - pseudoprotodioscin - microbial metabolism - cytotoxicity

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Dr. Xizhi Feng

Department of Chemistry

University of Virginia

P.O. Box 400319

Charlottesville

Virginia 22904-4319

USA

Phone: +1-434-249-4865

Fax: +1-513-558-2445

Email: xf3p@virginia.edu