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Chemical Compound Review

gamolenate     (6Z,9Z,12Z)-octadeca-6,9,12- trienoate

Synonyms: CPD-8117, CHEBI:32391, AC1NUU1G, ZINC03777423, gamma-linolenate, ...
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Disease relevance of gamma-Linolenic acid


High impact information on gamma-Linolenic acid

  • Gamma-Linolenate and eicosapentaenoate were poor substrates for both isozymes, but in each case, these two fatty acids were better substrates for hPGHS-2 than hPGHS-1 [6].
  • However, when an activated substrate, 7-hydroxycoumarinyl gamma-linolenate (pKa approximately 7.8 for its leaving group) was used as substrate, there was a significant level of 7-hydroxycoumarin esterase (7-HCEase) activity (about 1% of wild type) associated with the purified S228CC cPLA2 mutant [7].
  • However, stereochemical analysis of the acyl components of the sn-triacylglycerol obtained from mature seeds indicated that, whereas no gamma-linolenate was present at the sn-1 position, it accounted for over 50% of the fatty acids at position sn-3 [8].
  • This was further confirmed in experiments that compared the specific radioactivity of the gamma-linolenate, in acyl-CoA and phosphatidylcholine, that was synthesized when [14C]linoleoyl-CoA was incubated with microsomal membranes, NADH and non-radioactive gamma-linolenoyl-CoA [9].
  • We have previously shown that a 70% gamma-linolenate concentrate (GLA; an AA intermediate) fed at a fixed dose (0.07 g/day) normalized hepatic PL AA and reduced weight gain selectively in the obese animals [3].

Chemical compound and disease context of gamma-Linolenic acid

  • HUFA biosynthesis plays a role in counteracting doxorubicin toxicity, but it cannot completely overcome the depletion of these fatty acids; serum and exogenous gamma-linolenate are critical in filling the decreased HUFA pool [10].

Biological context of gamma-Linolenic acid

  • A series of genetically related cell lines that express mdr genes but differ in their ability to form tumors has been challenged with gamma-linolenate and eicosapentaenoate to verify if the sensitivity of tumorigenic mdr cells to cytotoxic PUFAs differs from the sensitivity of non-tumorigenic mdr cells [11].

Anatomical context of gamma-Linolenic acid


Associations of gamma-Linolenic acid with other chemical compounds


Gene context of gamma-Linolenic acid

  • A study of the 7-HCEase activity demonstrated that when 7-hydroxycoumarinyl gamma-linolenate was dispersed in a phospholipid matrix it was hydrolyzed by cPLA2 at a rate comparable to that of an arachidonyl-containing phospholipid substrate and with an identical reaction progress curve [17].


  1. Polyunsaturated fatty acid-induced cytotoxicity against tumor cells and its relationship to lipid peroxidation. Bégin, M.E., Ells, G., Horrobin, D.F. J. Natl. Cancer Inst. (1988) [Pubmed]
  2. Effect of gamma-linolenate in multiple sclerosis. Meyer-Rienecker, J.H., Jenssen, H.L., Kohler, H., Field, E.J., Shenton, B.K. Lancet (1976) [Pubmed]
  3. Time-dependent effects of progressive gamma-linolenate feeding on hyperphagia, weight gain, and erythrocyte fatty acid composition during growth of Zucker obese rats. Thurmond, D.C., Tang, A.B., Nakamura, M.T., Stern, J.S., Phinney, S.D. Obes. Res. (1993) [Pubmed]
  4. Lithium gamma-linolenate-induced cytotoxicity against cells chronically infected with HIV-1. Kinchington, D., Randall, S., Winther, M., Horrobin, D. FEBS Lett. (1993) [Pubmed]
  5. Inhibitory effects of mold oil including gamma-linolenate on platelet thrombus formation in mesenteric microvessels of the rat. Nakahara, T., Yokochi, T., Kamisaka, Y., Yamaoka, M., Suzuki, O., Sato, M., Okazaki, S., Ohshima, N. Thromb. Res. (1990) [Pubmed]
  6. Fatty acid substrate specificities of human prostaglandin-endoperoxide H synthase-1 and -2. Formation of 12-hydroxy-(9Z, 13E/Z, 15Z)- octadecatrienoic acids from alpha-linolenic acid. Laneuville, O., Breuer, D.K., Xu, N., Huang, Z.H., Gage, D.A., Watson, J.T., Lagarde, M., DeWitt, D.L., Smith, W.L. J. Biol. Chem. (1995) [Pubmed]
  7. Functional identification of the active-site nucleophile of the human 85-kDa cytosolic phospholipase A2. Huang, Z., Payette, P., Abdullah, K., Cromlish, W.A., Kennedy, B.P. Biochemistry (1996) [Pubmed]
  8. Delta 6- and delta 12-desaturase activities and phosphatidic acid formation in microsomal preparations from the developing cotyledons of common borage (Borago officinalis). Griffiths, G., Stobart, A.K., Stymne, S. Biochem. J. (1988) [Pubmed]
  9. Biosynthesis of gamma-linolenic acid in cotyledons and microsomal preparations of the developing seeds of common borage (Borago officinalis). Stymne, S., Stobart, A.K. Biochem. J. (1986) [Pubmed]
  10. Role of gamma-linolenic acid in counteracting doxorubicin-induced damage in cultured rat cardiomyocytes. Hrelia, S., Bordoni, A., Biagi, P.L. Prostaglandins Leukot. Essent. Fatty Acids (2001) [Pubmed]
  11. Transformation renders MDR cells more sensitive to polyunsaturated fatty acids. Sircar, S., Cai, F., Begin, M.E., Weber, J.M. Anticancer Res. (1990) [Pubmed]
  12. Manipulation of plasma membrane physical state affects desaturase activity in rat lymphocytes. Garcia Zevallos, M., Farkas, T. Arch. Biochem. Biophys. (1989) [Pubmed]
  13. Biosynthesis of C18 polyunsaturated fatty acids in microsomal membrane preparations from the filamentous fungus Mucor circinelloides. Jackson, F.M., Fraser, T.C., Smith, M.A., Lazarus, C., Stobart, A.K., Griffiths, G. Eur. J. Biochem. (1998) [Pubmed]
  14. Oleic acid desaturation in Tetrahymena pyriformis. Koudelka, A.P., Bradley, D.K., Kambadur, N., Ferguson, K.A. Biochim. Biophys. Acta (1983) [Pubmed]
  15. Fatty acid changes in liver choline and ethanolamine glycerophospholipids in aspirin-treated rats fed linoleate, gamma-linolenate and fish oil. Huang, Y.S., Watanabe, Y., Horrobin, D.F., Simmons, V. Clinical physiology and biochemistry. (1989) [Pubmed]
  16. The effects of dietary protein and cholesterol on tissue cholesterol contents and N-6 fatty acid compositions in rats and mice fed a gamma-linolenate-rich diet. Huang, Y.S., Watanabe, Y., Horrobin, D.F., Simmons, V. Monographs on atherosclerosis. (1990) [Pubmed]
  17. A continuous fluorescence-based assay for the human high-molecular-weight cytosolic phospholipase A2. Huang, Z., Laliberté, F., Tremblay, N.M., Weech, P.K., Street, I.P. Anal. Biochem. (1994) [Pubmed]
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