Document Detail

Inhibition of very-long-chain fatty acid formation by indanofan, 2-[2-(3-chlorophenyl)oxiran-2-ylmethyl]-2-ethylindan-1,3-dione, and its relatives.
MedLine Citation:
PMID:  11926546     Owner:  NLM     Status:  MEDLINE    
Indanofan and its analogs inhibited the elongation of stearoyl- or arachidoyl-CoA by [2-14C]-malonyl-CoA in leek microsomes from Allium porrum. Although the precise mode of interaction of indanofan at the molecular level is not completely clarified by the present study, it is concluded that indanofan and analogs act as inhibitor of the elongase enzyme involved in de novo biosynthesis of fatty acids with an alkyl chain longer than C18, called very-long-chain fatty acids (VLCFAs). For a strong inhibition of VLCFA formation chloro substituents at the benzene ring and the oxirane group were necessary. Furthermore, the greenhouse test showed strong activity for indanofan and its analogs, and the scores coincided with cell-free elongation inhibition. The cell-free assay, however, failed to indicate any activity for an analog having a methylene instead of the oxirane group, while both Digitaria ciliaris and Echinochloa oryzicola were killed with 1 kg a.i./ha. This finding cannot be discussed because the applied use rate of 1 kg a.i./ha is too high to allow for a score differentiation. For high concentrations of this compound additional unknown inhibitory effects may be involved besides fatty acid elongation.
Hideomi Takahashi; Jochen Schmalfuss; Aiko Ohki; Akemi Hosokawa; Akira Tanaka; Yukiharu Sato; Bernd Matthes; Peter Böger; Ko Wakabayashi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Zeitschrift für Naturforschung. C, Journal of biosciences     Volume:  57     ISSN:  0939-5075     ISO Abbreviation:  Z. Naturforsch., C, J. Biosci.     Publication Date:    2002 Jan-Feb
Date Detail:
Created Date:  2002-04-02     Completed Date:  2002-05-10     Revised Date:  2009-11-04    
Medline Journal Info:
Nlm Unique ID:  8912155     Medline TA:  Z Naturforsch C     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  72-4     Citation Subset:  IM    
Graduate School of Agricultural Science, Tamagawa University, Tokyo, Japan.
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MeSH Terms
Acyl Coenzyme A / metabolism
Acyl-Carrier Protein S-Malonyltransferase
Acyltransferases / antagonists & inhibitors
Allium / metabolism*
Carbon Radioisotopes
Cell-Free System
Chlorobenzenes / pharmacology*
Fatty Acids / biosynthesis*,  chemistry
Herbicides / pharmacology*
Indans / pharmacology*
Malonyl Coenzyme A / metabolism
Stearic Acids / metabolism
Structure-Activity Relationship
Reg. No./Substance:
0/Acyl Coenzyme A; 0/Carbon Radioisotopes; 0/Chlorobenzenes; 0/Fatty Acids; 0/Herbicides; 0/Indans; 0/Stearic Acids; 0/indanofan; 524-14-1/Malonyl Coenzyme A; EC 2.3.-/Acyltransferases; EC Protein S-Malonyltransferase

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