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Lipoxygenase Inhibitory Activity of Anacardic Acids

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2005, 53, 11, 4350-4354
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    Lipoxygenase Inhibitory Activity of Anacardic Acids
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    Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2005, 53, 11, 4350–4354
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    https://doi.org/10.1021/jf048184e
    Published May 10, 2005
    Copyright © 2005 American Chemical Society
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    Abstract

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    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 μM. 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 μM. 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.

    Keywords: Lipoxygenase inhibitors; anacardic acids; competitive inhibitor; Dixon plots; time-dependent inhibition

    Copyright © 2005 American Chemical Society

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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2005, 53, 11, 4350–4354
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf048184e
    Published May 10, 2005
    Copyright © 2005 American Chemical Society
    Request reuse permissions

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