13(S)-HpODE

13(S)-HpODE is produced by the oxidation of linoleic acid by lipoxygenase-1 (LO-1) in many plants including soybean, flaxseed, apples, and tea leaves,1,2 and by 15-LO in mammals.3 In plants, 13(S)-HpODE is the preferred substrate for the garlic bulb divinyl ether synthase.4 In mammalian tissues, 13(S)-HpODE is generally reduced to 13(S)-HODE,a compound which exhibits many biological activities.3 A direct action for 13(S)-HpODE has been demonstrated in Syrian hamster embryo cells where it stimulates EGF-dependent mitogenesis and up-regulation of EGF-dependent tyrosine phosphorylation.5 Membrane-esterified 13(S)-HpODE has been identified in human atherosclerotic plaques.6

Reference:

1. Gardner, H.W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism Biochim. Biophys. Acta 1001(3), 274-281 (1989).

2. Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway Lipid Metabolism in Plants 167-191 (1993).

3. Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid Progress in Lipid Research 35, 203-226 (1996).

4. Grechkin, A.N., and Hamberg, M. Divinyl ether synthase from garlic (Allium sativum L.) bulbs: Sub-cellular localization and substrate regio- and stereospecificity FEBS Letters 388, 112-114 (1996).

5. Glasgow, W.C., Hui, R., Everhart, A.L., et al. The linoleic acid metabolite, (13S)-hydroperoxyoctadecadienoic acid, augments the epidermal growth factor receptor signaling pathway by attenuation of receptor dephosphorylation. Differential response in Syrian hamster embryo tumor suppressor phenotypes The Journal of Biological Chemisty 272, 19269-19276 (1997).

6. Folcik, V.A., Nivar-Aristy, R.A., Krajewski, L.P., et al. Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques Journal of Clinical Investigation 96, 504-510 (1995).