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  • Substrate specificity effects of lipoxygenase products and inhibitors on soybean lipoxygenase-1.

Substrate specificity effects of lipoxygenase products and inhibitors on soybean lipoxygenase-1.

Bioorganic & medicinal chemistry (2009-09-01)
Aaron T Wecksler, Natalie K Garcia, Theodore R Holman
ABSTRACT

Recently, it has been shown that lipoxygenase (LO) products affect the substrate specificity of human 15-LO. In the current paper, we demonstrate that soybean LO-1 (sLO-1) is not affected by its own products, however, inhibitors which bind the allosteric site, oleyl sulfate (OS) and palmitoleyl sulfate (PS), not only lower catalytic activity, but also change the substrate specificity, by increasing the arachidonic acid (AA)/linoleic acid (LA) ratio to 4.8 and 4.0, respectively. The fact that LO inhibitors can lower activity and also change the LO product ratio is a new concept in lipoxygenase inhibition, where the goal is to not only reduce the catalytic activity but also alter substrate selectivity towards a physiologically beneficial product.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Linoleic acid, technical, 58-74% (GC)
Supelco
Linoleic acid, analytical standard
Sigma-Aldrich
Linoleic acid, liquid, BioReagent, suitable for cell culture
Sigma-Aldrich
Oleic Acid-Water Soluble, powder, BioReagent, suitable for cell culture
Sigma-Aldrich
α-Linoleic acid, ≥98%
Sigma-Aldrich
Oleic acid, natural, FCC
Sigma-Aldrich
Oleic acid, meets analytical specification of Ph, Eur., 65.0-88.0% (GC)
Sigma-Aldrich
Oleic acid, technical grade, 90%
Supelco
Oleic acid, analytical standard
Supelco
Oleic acid, Selectophore, ≥99%
Sigma-Aldrich
Oleic acid, ≥99% (GC)
Sigma-Aldrich
Oleic acid, BioReagent, suitable for cell culture