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Biosynthesis of 14,15-hepoxilins in human L1236 hodgkin lymphoma cells and eosinophils
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för neurokemi.ORCID-id: 0000-0002-6416-064X
Vise andre og tillknytning
2011 (engelsk)Inngår i: Lipids, ISSN 0024-4201, E-ISSN 1558-9307, Vol. 46, nr 1, s. 69-79Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Hepoxilins are epoxy alcohols synthesized through the 12-lipoxygenase (12-LO) pathway in animal cells. The epidermis is the principal source of hepoxilins in humans. Here we report on the formation of novel hepoxilin regioisomers formed by the 15-LO pathway in human cells. The Hodgkin lymphoma cell line L1236 possesses high 15-lipoxygenase-1 (15-LO-1) activity and incubation of L1236 cells with arachidonic acid led to the formation of 11(S)-hydroxy-14(S),15(S)-epoxy 5(Z),8(Z),12(E) eicosatrienoic acid (14,15-HxA(3) 11(S)) and 13(R)-hydroxy-14(S),15(S)-epoxy 5(Z),8(Z),11(Z) eicosatrienoic acid (14,15-HxB(3) 13 (R)). In addition, two hitherto unidentified products were detected and these products were collected and analyzed by positive ion electrospray tandem mass spectrometry. These metabolites were identified as 11(S),15(S)-dihydroxy-14(R)-glutathionyl-5(Z),8(Z),12(E)-eicosatrienoic acid (14,15-HxA(3)-C) and 11(S),15(S)-dihydroxy-14(R)-cysteinyl-glycyl-5(Z),8(Z),12(E)-eicosatrienoic acid (14,15-HxA(3)-D). Incubation of L1236 cells with synthetic 14,15-HxA(3) 11(S) also led to the formation of 14,15-HxA(3)-C and 14,15-HxA(3)-D. Several soluble glutathione transferases, in particular GST M1-1 and GST P1-1, were found to catalyze the conversion of 14,15-HxA(3) to 14,15-HxA(3)-C. L1236 cells produced approximately twice as much eoxins as cysteinyl-containing hepoxilins upon stimulation with arachidonic acid. Human eosinophils, nasal polyps and dendritic cells selectively formed 14,15-HxA(3) 11(S) and 14,15-HxB(3) 13(R) stereoisomers, but not cysteinyl-containing hepoxilins, after stimulation with arachidonic acid. Furthermore, purified recombinant 15-LO-1 alone catalyzed the conversion of arachidonic acid to 14,15-HxA(3) 11(S) and 14,15-HxB(3) 13(R), showing that human 15-LO-1 possesses intrinsic 14,15-hepoxilin synthase activity.

sted, utgiver, år, opplag, sider
2011. Vol. 46, nr 1, s. 69-79
Emneord [en]
Arachidonic acid, L1236, Hodgkin Reed-Sternberg cells, 15-Lipoxygenase, Glutathione conjugate
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-53704DOI: 10.1007/s11745-010-3485-1PubMedID: 21046276OAI: oai:DiVA.org:su-53704DiVA, id: diva2:391181
Tilgjengelig fra: 2011-01-24 Laget: 2011-01-24 Sist oppdatert: 2017-12-11bibliografisk kontrollert

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