LIPID MAPS

(±)11-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro.^1,2 It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes.^3,4,5 DHA is metabolized to 11(S)-HDHA by human platelets and canine retina.^6,7,8,5 In addition to 11(S)-HDHA, 14(S)-HDHA is also produced by platelets.^6,8,5 11(S)-HDHA was shown to be an inhibitor of U-46619-induced human platelet aggregation and rabbit and rat aortic smooth muscle contraction with IC50 values of about 50, 4.7, and 7.5 µM, respectively.^8,9 (±)11-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

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References

1. Kim, H.Y., Karanian, J.W., Shingu, T., et al. Sterochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate. Prostaglandins 40(5), 473-490 (1990).

2. Reynaud, D., Thickitt, C.P., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal. Biochem. 214(1), 165-170 (1993).

3. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. J. Chromatogr. 652(2), 123-136 (1994).

4. Bazan, N.G., Birkle, D.L., and Reddy, T.S. Docosahexaenoic acid (22:6, n-3) is metabolized to lipoxygenase reaction products in the retina. Biochem. Biophys. Res. Commun. 125(2), 741-747 (1984).

5. Lagarde, M., Croset, M., Guichardant, M., et al. Role of lipoxygenase products in platelet function: Relation to fatty acid modified phospholipids. Adv. Exp. Med. Biol. 192, 327-335 (1985).

6. Aveldaño, M.I., and Sprecher, H. Synthesis of hydroxy fatty acids from 4,7,10,13,16,19-[1-14C] docosahexaenoic acid by human platelets. J. Biol. Chem. 258(15), 9339-9343 (1983).

7. Karanian, J.W., Kim, H.Y., and Salem, N., Jr. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J. Pharmacol. Exp. Ther. 270(3), 1105-1109 (1994).

8. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J. Biol. Chem. 259(9), 5776-5783 (1984).

9. VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J. Lipid Res. 25(5), 507-517 (1984).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

InChiKey (Click to copy)

LTERDCBCHFKFRI-BGKMTWLOSA-N

InChi (Click to copy)

InChI=1S/C22H32O3/c1-2-3-4-5-6-7-9-12-15-18-21(23)19-16-13-10-8-11-14-17-20-22(24)25/h3-4,6-7,10-16,19,21,23H,2,5,8-9,17-18,20H2,1H3,(H,24,25)/b4-3-,7-6-,13-10-,14-11-,15-12-,19-16+

SMILES (Click to copy)

OC(=O)CC/C=C\C/C=C\C=C\C(O)C/C=C\C/C=C\C/C=C\CC

CHEBI ID

72794

PubChem CID

11631564

Cayman ID

33450

Heavy Atoms 25

Rings 0

Aromatic Rings 0

Rotatable Bonds 14