Document Detail


Lipoxygenase inhibitory activity of anacardic acids.
MedLine Citation:
PMID:  15913294     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
6[8'(Z)-pentadecenyl]salicylic acid, otherwise known as anacardic acid (C15:1), inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) with an IC50 of 6.8 microM. The inhibition of the enzyme by anacardic acid (C15:1) is a slow and reversible reaction without residual activity. The inhibition kinetics analyzed by Dixon plots indicates that anacardic acid (C15:1) is a competitive inhibitor and the inhibition constant, KI, was obtained as 2.8 microM. Although anacardic acid (C15:1) inhibited the linoleic acid peroxidation without being oxidized, 6[8'(Z),11'(Z)-pentadecadienyl]salicylic acid, otherwise known as anacardic acid (C15:2), was dioxygenated at low concentrations as a substrate. In addition, anacardic acid (C15:2) was also found to exhibit time-dependent inhibition of lipoxygenase-1. The alk(en)yl side chain of anacardic acids is essential to elicit the inhibitory activity. However, the hydrophobic interaction alone is not enough because cardanol (C15:1), which possesses the same side chain as anacardic acid (C15:1), acted neither as a substrate nor as an inhibitor.
Authors:
Tae Joung Ha; Isao Kubo
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  53     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2005 Jun 
Date Detail:
Created Date:  2005-05-25     Completed Date:  2005-07-05     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4350-4     Citation Subset:  IM    
Affiliation:
Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA.
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MeSH Terms
Descriptor/Qualifier:
Anacardic Acids / chemistry,  metabolism,  pharmacology*
Kinetics
Linoleic Acid / metabolism
Lipid Peroxidation
Lipoxygenase / metabolism
Lipoxygenase Inhibitors / pharmacology*
Molecular Structure
Soybeans / enzymology
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anacardic Acids; 0/Lipoxygenase Inhibitors; 18654-18-7/anacardic acid; 2197-37-7/Linoleic Acid; EC 1.13.11.12/Lipoxygenase

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


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