Lipoxygenase inhibitory activity of anacardic acids.
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.
Ha
Tae Joung
TJ
Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA.
Kubo
Isao
I
D048729:Anacardic Acids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D007700:Kinetics; D019787:Linoleic Acid / Q000378:metabolism; D015227:Lipid Peroxidation; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000494:pharmacology*; D015394:Molecular Structure; D013025:Glycine max / Q000201:enzymology; D013329:Structure-Activity Relationship
D048729:Anacardic Acids; D016859:Lipoxygenase Inhibitors; C088115:anacardic acid; D019787:Linoleic Acid; D008084:Lipoxygenase