Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
Document Type
Article
Publication Date
1-1-2010
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.
Publication Title
Journal of Natural Products-Copublished with the Am. Soc. of Pharmacognosy
Volume
73
Issue
6
Publisher
American Chemical Society
Publisher Location
1155 16TH ST, NW, WASHINGTON, DC 20036 USA