LIPID MAPS

9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.^1,2,3,4 It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.^1,5 9(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50 = 28.7 µg/ml).² It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50 = 40.95 µM).³ In vivo, 9(S),12(S),13(S)-TriHOME (1 g/animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.⁴

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References

1. Hamberg, M., and Hamberg, G. Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid. Plant Physiol. 110(3), 807-815 (1996).

2. Hong, S.S., and Oh, J.S. Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat bran. J. Korean Soc. Appl. Biol. Chem. 55, 69-74 (2012).

3. Kim, C.S., Kwon, O.W., Kim, S.Y., et al. Five new oxylipins from Chaenomeles sinensis. Lipids 49(11), 1151-1159 (2014).

4. Shirahata, T., Sunazuka, T., Yoshida, K., et al. Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids. Tetrahedron 62(40), 9483-9496 (2006).

5. Fuchs, D., Tang, X., Johnsson, A.-K., et al. Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent process. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1865(4), 158611 (2020).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent process.,
Biochim Biophys Acta Mol Cell Biol Lipids, 2020

Pubmed ID: 31918007

DOI: 10.1016/j.bbalip.2020.158611

Pinellia ternata (#199225)

Magnoliopsida (#3398)

Pinellic acid from the tuber of Pinellia ternata Breitenbach as an effective oral adjuvant for nasal influenza vaccine.,
Int Immunopharmacol, 2002

Pubmed ID: 12349955

DOI: 10.1016/s1567-5769(02)00086-3

InChiKey (Click to copy)

MDIUMSLCYIJBQC-MVFSOIOZSA-N

InChi (Click to copy)

InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1

SMILES (Click to copy)