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Structure Database (LMSD)

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Common Name

9,12,13-TriHOME

Systematic Name

9S,12S,13S-trihydroxy-10E-octadecenoic acid

Synonyms

Pinellic acid
Dihydrofulgidic acid

LM ID

LMFA02000014

Formula

C₁₈H₃₄O₅

Exact Mass

Calculate m/z

330.240625

Sum Composition

FA 18:1;O3

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

3. 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).

4. 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).

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

References

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

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