Document Detail


Microbial transformations of natural antitumor agents, 25. Conversions of 3-ketoaphidicolin.
MedLine Citation:
PMID:  6434698     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Microbial transformation experiments were conducted using 3-ketoaphidicolin (2) as a starting material. Metabolites were isolated by solvent extraction and chromatography, and structures were elaborated by cmr and pmr spectroscopy, ms, and ir analyses. Several microorganisms provided metabolites in excellent yields, including 3-epiaphidicolin (4), 6 beta-hydroxy-3-ketoaphidicolin (5), and 19-nor-16,17-dihydroxyaphidicolan-3-one (6). The last compound is formed via oxidation of the primary alcohol functional group at position 18 to the corresponding beta-keto acid derivative which spontaneously decarboxylates. This reaction is analogous to the metabolic demethylation of sterol intermediates. Each metabolite was tested for antitumor activity in the P-388 leukemic test system, and in the 6C631 colon tumor model system. None of the compounds were active in vivo, and all were less active than aphidicolin in the in vitro P-388 test system.
Authors:
J Ipsen; J P Rosazza
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of natural products     Volume:  47     ISSN:  0163-3864     ISO Abbreviation:  J. Nat. Prod.     Publication Date:    1984 May-Jun
Date Detail:
Created Date:  1984-11-02     Completed Date:  1984-11-02     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  497-503     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Animals
Antibiotics, Antineoplastic / metabolism*,  pharmacology
Aphidicolin
Biotransformation
Chaetomium / metabolism
Diterpenes / metabolism*,  pharmacology
Fermentation
Leukemia P388 / drug therapy
Magnetic Resonance Spectroscopy
Rats
Streptomyces / metabolism
Grant Support
ID/Acronym/Agency:
NCI-CM-07324/CM/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Antibiotics, Antineoplastic; 0/Diterpenes; 38966-21-1/Aphidicolin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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