(±)9(10)-DiHOME

(±)9(10)-DiHOME is the diol form of (±)9(10)-EpOME (Item No. 52400), a cytochrome P450-derived epoxide of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) also known as leukotoxin.¹ It is formed from 9(10)-EpOME by soluble epoxide hydrolase (sEH) in neutrophils.² It is toxic to Sf21 cells expressing sEH and to lacZ-expressing control cells, unlike leukotoxin, which is only toxic to cells containing sEH.^1,2 A mixture of 9(10)- and 12(13)-DiHOME induces cell death in rabbit renal proximal tubule cells concomitant with mitochondrial respiration dysfunction and induces lung injury, respiratory distress, and mortality in mice.^3,4 9(10)-DiHOME is a toxic lipid mediator involved in acute respiratory distress syndrome (ARDS), a common and often fatal complication in severe burn victims.^2,3 Levels of 9(10)-DiHOME are increased in bronchoalveolar lavage fluid (BALF) from women, but not men, with chronic obstructive pulmonary disease (COPD).⁵ BALF levels are also increased in patients with allergic asthma following allergen exposure compared to patients without allergic asthma.⁶ It has been used as a plasma biomarker for sEH activity in vivo.⁷

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1. Greene, J.F., Williamson, K.C., Newman, J.W., et al. Metabolism of monoepoxides of methyl linoleate: Bioactivation and detoxification. Arch. Biochem. Biophys. 376(2), 420-432 (2000).

2. Moghaddam, M.F., Grant, D.F., Cheek, J.M., et al. Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase. Nat. Med. 3(5), 562-566 (1997).

3. Zheng, J., Plopper, C.G., Lakritz, J., et al. Leukotoxin-diol a putative toxic mediator involved in acute respiratory distress syndrome. Am. J. Respir. Cell Mol. Biol. 25(4), 434-438 (2001).

4. Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol. Appl. Pharmacol. 146(1), 53-59 (1997).

5. Balgoma, D., Yang, M., Sjödin, M., et al. Linoleic acid-derived lipid mediators increase in a female-dominated subphenotype of COPD. Eur. Respir. J. 47(6), 1645-1656 (2016).

6. Lundström, S.L., Yang, J., Källberg, H.J., et al. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation. PLoS One 7(3), e33780 (2012).

7. Zhu, P., Peck, B., Licea-Perez, H., et al. Development of a semi-automated LC/MS/MS method for the simultaneous quantitation of 14,15-epoxyeicosatrienoic acid, 14,15-dihydroxyeicosatrienoic acid, leukotoxin and leukotoxin diol in human plasma as biomarkers of soluble epoxide hydrolase activity in vivo. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879(25), 2487-2493 (2011).

Matsumoto, K., Takada, Y., Imamura, Y., et al. Live and heat-treated Lactiplantibacillus plantarum induce distinct metabolic and immune responses in intestinal epithelial cells. iScience 29(5), 115516 (2026).

Nirengi, S., Buck, B., Das, D., et al. 12,13-diHOME protects against the age-related decline in cardiovascular function via attenuation of CaMKII. Nat. Commun. 16(1), 7088 (2025).

Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

Morisseau, C., and Hammock, B.D. Measurement of soluble epoxide hydrolase (sEH) activity. Curr. Protoc. Toxicol. 4.23.2(Suppl. 33), (2007).