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

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. Thes...

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Main Authors: Leverrier, A., Martin, Marie-Therese, Servy, C., Ouazzani, J., Retailleau, P., Awang, Khalijah, Mukhtar, M.R., Gueritte, F., Litaudon, M.
Format: Article
Published: American Chemical Society 2010
Subjects:
R Medicine
Online Access:http://eprints.um.edu.my/13387/
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spelling my.um.eprints.133872019-03-01T09:16:58Z http://eprints.um.edu.my/13387/ Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus Leverrier, A. Martin, Marie-Therese Servy, C. Ouazzani, J. Retailleau, P. Awang, Khalijah Mukhtar, M.R. Gueritte, F. Litaudon, M. R Medicine 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. American Chemical Society 2010 Article PeerReviewed 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.
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic R Medicine
spellingShingle R Medicine
Leverrier, A.
Martin, Marie-Therese
Servy, C.
Ouazzani, J.
Retailleau, P.
Awang, Khalijah
Mukhtar, M.R.
Gueritte, F.
Litaudon, M.
Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
description 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.
format Article
author Leverrier, A.
Martin, Marie-Therese
Servy, C.
Ouazzani, J.
Retailleau, P.
Awang, Khalijah
Mukhtar, M.R.
Gueritte, F.
Litaudon, M.
author_facet Leverrier, A.
Martin, Marie-Therese
Servy, C.
Ouazzani, J.
Retailleau, P.
Awang, Khalijah
Mukhtar, M.R.
Gueritte, F.
Litaudon, M.
author_sort Leverrier, A.
title Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
title_short Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
title_full Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
title_fullStr Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
title_full_unstemmed Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic Acid by Rhizopus arrhizus
title_sort rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic acid by rhizopus arrhizus
publisher American Chemical Society
publishDate 2010
url http://eprints.um.edu.my/13387/
_version_ 1643689536209813504
score 13.211869

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