Description
12(S)-
HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of platelet or leukocyte 12-
lipoxygenase (12-
LO) on arachidonic acid. It activates human blood leukocyte 5-
LO, resulting in the synthesis of 5(S)-
HETE, leukotriene B
4 (LTB
4), and 5(S),12(S)-
DiHETE. Rat lung metabolizes 12(S)-
HpETE to 8,11,12-
and 10,11,12-
trihydroxyeicostrienoic acids. 12(S)-
HpETE is the mediator of many biological functions, including induction of c-
fos and c-
jun, activation of AP-
1, and endothelium-
dependent vasoconstriction. It mediates the inhibitory synaptic response to FMRF-
amide in
Aplysia sensory neurons and inhibits Ca
2+/calmodulin-
dependent protein kinase II from rat brain cortex.
Definition
ChEBI: 12(S)-HPETE is the (S)-enantiomer of 12-HPETE. It has a role as a mouse metabolite. It is functionally related to an icosa-5,8,10,14-tetraenoic acid. It is a conjugate acid of a 12(S)-HPETE(1-). It is an enantiomer of a 12(R)-HPETE.
References
[1] J MACLOUF P B B F de Laclos. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-icosatetraenoic acid.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1982, 79 19: 6042-6046. DOI:
10.1073/pnas.79.19.6042[2] KOJI KISHIMOTO . Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1996, 1300 1: Pages 56-62. DOI:
10.1016/0005-2760(95)00241-3[3] C. PACE-ASCIAK B S E Granstrm. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids.[J]. The Journal of Biological Chemistry, 1983, 48 1: 6835-6840. DOI:
10.1016/s0021-9258(18)32298-1[4] MAKOTO NISHIYAMA . Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction[J]. European journal of pharmacology, 1998, 341 1: Pages 57-63. DOI:
10.1016/s0014-2999(97)01353-8[5] G N RAO. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity.[J]. The Journal of Biological Chemistry, 1996, 271 44: 27760-27764. DOI:
10.1074/jbc.271.44.27760[6] D. PIOMELLI. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition of Aplysia sensory cells[J]. Nature, 1987, 328 6125: 38-43. DOI:
10.1038/328038a0[7] D PIOMELLI. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1989, 86 21: 8550-8554. DOI:
10.1073/pnas.86.21.8550
