Soybean lipoxygenase-promoted oxidation of free and esterified linoleic acid in the presence of deoxycholate |
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Authors: | George J Piazza Thomas A Foglia Alberto Nuñez |
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Affiliation: | (1) USDA, ARS, ERRC, 600 East Mermaid Lane Wyndmoor, PA, 19038 |
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Abstract: | Lipoxygenase (EC 1.13.11.12) catalyzes the reaction between oxygen and polyunsaturated fatty acids to give fatty acid hydroperoxides.
Recent work showed that soybean lipoxygenase 1 can oxidize diacylglycerols when deoxycholate is present in the reaction medium.
Conditions were sought to maximize 1,3-dilinolein oxidation with a commercial soybean lipoxygenase preparation. It was found
that dilinolein was oxidized most rapidly in a multicomponent buffer medium that contained 10 mM deoxycholate between pH 8
and 9. When dilinolein oxidation was conducted in the individual components of the multicomponent buffer, the oxidation rate
decreased two- to threefold. Addition of 0.2 M NaCl to one of the components, Tricine buffer, caused a twofold increase in
the oxidation rate, demonstrating that high ionic strength is a major factor promoting rapid oxidation in the multicomponent
buffer. In the deoxycholate multicomponent buffer, the order of reactivity toward oxidation was monolinolein>methyl linoleate≈
linoleic acid>dilinolein. Competition experiments in which mixtures of the substrates were presented simultaneously to lipoxygenase
in the presence of deoxycholate showed that linoleic acid was the most reactive substrate. When no surfactant was present
or when the surfactant was Tween 20, linoleic acid was the most rapidly oxidized substrate. Overall, the results demonstrate
that monolinolein and methyl linoleate are just as reactive, or more so, as linoleic acid to oxidation by lipoxygenase under
specified reaction conditions. In competition experiments, linoleic acid oxidation predominates, probably because its free
carboxyl functionality allows it to be preferentially bound to the active site of lipoxygenase. |
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Keywords: | Deoxycholate diacylglycerol Glycine max hydroperoxide linoleate lipoxygenase monoacylglycerol |
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