Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus

Leverrier, A. and Martin, Marie-Therese and Servy, C. and Ouazzani, J. and Retailleau, P. and Awang, Khalijah and Mukhtar, M.R. and Gueritte, F. and Litaudon, M. (2010) Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus. Journal of Natural Products-Copublished with the Am. Soc. of Pharmacognosy, 73 (6). pp. 1121-1125.

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Abstract

In our search for inhibitors of the antiapoptotic protein Bcl-xL, investigation of Xylopia caudata afforded a new diterpenoid, ent-trachyloban-4 beta-ol (2), and five known ent-trachylobane or ent-atisane compounds. Only ent-trachyloban-18-oic acid (1) exhibited weak binding activity to Bcl-xL. These compounds exhibited cytotoxicity against KB and HCT-116 cell lines with IC(50) values between 10 and 30 mu M. Bioconversion of compound 1 by Rhizopus arrhizus afforded new hydroxylated metabolites (3-7) of the ent-trachylobane ancl ent-kaurene type;aid compound 8, with a rearranged pentacyclic carbon framework that was named rhizopene. Compounds 3-8 were noncytotoxic to the two cancer cell lines, and compounds 3 and 5 exhibited only weak binding affinity for Bcl-xL.

Item Type: Article
Funders: UNSPECIFIED
Subjects: R Medicine
Depositing User: Mr Faizal 2
Date Deposited: 27 Apr 2015 01:30
Last Modified: 01 Mar 2019 09:16
URI: http://eprints.um.edu.my/id/eprint/13387

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