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Chemical Compound Review

Ro 12-1989     (8Z,11Z,14Z)-icosa-8,11,14- trienoic acid

Synonyms: DGLA, CHEMBL465183, BSPBio_001286, CHEBI:53486, E4504_SIGMA, ...
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Disease relevance of Ro 12-1989

  • The proportion of dihomo-gamma-linolenic acid (20:3n-6) in serum phospholipids was inversely related to insulin sensitivity both before (r = -0.48, P < 0.001) and after (r = -0.46, P < 0.001) weight loss, but it did not change significantly in either group [1].
  • Uptake and metabolism of exogenous eicosa-8,11,14-trienoic acid in minimal deviation hepatoma 7288 C cells [2].
  • The most significant findings in eczema patient MNC were reduced ratios of 20:4n-6/20:3n-6 in total lipids and in phosphatidyl ethanolamine (PE) and of 20:4n-6/18:2n-6 in both total lipids, phosphatidyl choline (PC) and PE [3].
  • PN applied to malnourished patients with cystic fibrosis results in beneficial effects in a subgroup characterized by the presence of DHLA in serum; for the group as a whole, the positive effects are minimal [4].
  • Results showed that both spontaneous hypertension and salt-loading suppressed the desaturation of radiolabeled 18:2n-6 and of 20:3n-6 [5].

Psychiatry related information on Ro 12-1989

  • Linoleic acid (18:2n-6), the precursor of the n-6 fatty acids, was below normal in intermittent explosive disorder, but the dihomogammalinolenic acid (DGLA) (20:3n-6) and some subsequent n-6 acids were at the same time elevated among all offenders [6].

High impact information on Ro 12-1989


Biological context of Ro 12-1989

  • Beyond 30, 20, and 60 microM of 18:2n-6, 20:3n-6, and 18:3n-3 concentration, respectively, the enzyme activity deviated from Michaelis-Menten kinetics, suggesting an inhibition by excess substrate which is unlikely to occur in vivo as endogenous substrate concentration is much lower [12].
  • These results demonstrate in term baboon neonates that in vivo 1) 20:4n-6 was retroconverted to 20:3n-6, 2) 20:4n-6 did not contribute significantly to de novo lipogenesis of saturates and monounsaturates, and 3) the preformed 20:4n-6 contribution to brain 22:4n-6 accumulation was quantitatively a significant metabolic fate for dietary 20:4n-6 [13].
  • Preincubating the highly TNF-sensitive WEHI clone 13 cells for 44 hr with 50 mumol/L of 20:5n-3, 22:6n-3, 18:3n-6, 20:3n-6 or 20:4n-6 reduced cell survival 22 hr after challenge with TNF (40 ng/L) by 65%, 72%, 60%, 98% and 85%, respectively [14].
  • During the course of lactation the levels of n-6 metabolites, e.g. 18:3n-6, 20:3n-6 and 20:4n-6, in milk fat declined progressively [15].
  • Pulmonary function improved in patients who normalized their DHLA levels (vital capacity increased from 2.2 +/- 0.3 to 2.6 +/- 0.3 area %, p < 0.05), whereas those who continued to have undetectable levels of DHLA deteriorated (forced expiratory volume in 1 s decreased from 0.7 +/- to 0.6 +/- 0.1, p < 0.001) [4].

Anatomical context of Ro 12-1989


Associations of Ro 12-1989 with other chemical compounds


Gene context of Ro 12-1989

  • In BOR and MIX animals, 20:3n-6 levels were significantly increased (P less than 0.05) in all phospholipids relative to SAF and MFO [25].
  • The proportions of the major long-chain polyunsaturated fatty acids (LCP), 20:3n-6, 20:4n-6, 22:5n-3 and 22:6n-3, were highest at 1 week and decreased thereafter in both types of milk [26].

Analytical, diagnostic and therapeutic context of Ro 12-1989

  • Likewise, plasma levels of 20:3n-6, 20: 5n-3, and 22:6n-3 were lower in Usher's syndrome type I compared with the control group [27].
  • In conclusion, intravenous injection of a DGLA emulsion increased DGLA concentrations in immune cells within 1 h and suppressed the DTH reaction [28].
  • Fat-free diet produces a reduction in the conversion of eicosa-8,11,14-trienoic acid to arachidonic acid [29].
  • The concentrations of the fatty acids 20:3n-6 and 20:4n-6 were significantly reduced after 3.5 months with a vegan diet (P < 0.0001 and P < 0.01 respectively), but the concentration increased to baseline values with a lactovegetarian diet [30].
  • The substrate of the reaction [1-14C]eicosa-8,11,14-trienoic acid (20:3n-6), was separated from the product [1-14C]eicosa-5,8,11,14-tetraenoic acid (20:4n-6) by reverse phase high-pressure liquid chromatography (RP-HPLC) [31].


  1. Effects of equal weight loss with orlistat and placebo on body fat and serum fatty acid composition and insulin resistance in obese women. Tiikkainen, M., Bergholm, R., Rissanen, A., Aro, A., Salminen, I., Tamminen, M., Teramo, K., Yki-Järvinen, H. Am. J. Clin. Nutr. (2004) [Pubmed]
  2. Uptake and metabolism of exogenous eicosa-8,11,14-trienoic acid in minimal deviation hepatoma 7288 C cells. Gaspar, G., de Alaniz, M.J., Brenner, R.R. Lipids (1975) [Pubmed]
  3. Polyunsaturated fatty acids in plasma, red blood cells and mononuclear cell phospholipids of patients with atopic dermatitis. Lindskov, R., Hølmer, G. Allergy (1992) [Pubmed]
  4. Long-term parenteral nutrition in cystic fibrosis. Kirvela, O., Stern, R.C., Askanazi, J., Doershuk, C.F., Rothkopf, M.M., Katz, D.P. Nutrition (Burbank, Los Angeles County, Calif.) (1993) [Pubmed]
  5. Effect of salt-loading and spontaneous hypertension on in vitro metabolism of [1-14C]linoleic and [2-14C]dihomo-gamma-linolenic acids. Poisson, J.P., Huang, Y.S., Mills, D.E., de Antueno, R.J., Redden, P.R., Lin, X., Narce, M., Horrobin, D.F. Biochem. Med. Metab. Biol. (1993) [Pubmed]
  6. Plasma phospholipid essential fatty acids and prostaglandins in alcoholic, habitually violent, and impulsive offenders. Virkkunen, M.E., Horrobin, D.F., Jenkins, D.K., Manku, M.S. Biol. Psychiatry (1987) [Pubmed]
  7. Fatty acids and their prostaglandin derivatives: inhibitors of proliferation in aortic smooth muscle cells. Huttner, J.J., Gwebu, E.T., Panganamala, R.V., Milo, G.E., Cornwell, D.C., Sharma, H.M., Geer, J.C. Science (1977) [Pubmed]
  8. Transformation of arachidonic acid and homo-gamma-linolenic acid by rabbit polymorphonuclear leukocytes. Monohydroxy acids from novel lipoxygenases. Borgeat, P., Hamberg, M., Samuelsson, B. J. Biol. Chem. (1976) [Pubmed]
  9. Dietary manipulation implicates lipid signaling in the regulation of germ cell maintenance in C. elegans. Watts, J.L., Browse, J. Dev. Biol. (2006) [Pubmed]
  10. Evening primrose oil and borage oil in rheumatologic conditions. Belch, J.J., Hill, A. Am. J. Clin. Nutr. (2000) [Pubmed]
  11. Umbilical vessels of preeclamptic women have low contents of both n-3 and n-6 long-chain polyunsaturated fatty acids. Velzing-Aarts, F.V., van der Klis, F.R., van der Dijs, F.P., Muskiet, F.A. Am. J. Clin. Nutr. (1999) [Pubmed]
  12. Delta6- and delta5-desaturase activities in the human fetal liver: kinetic aspects. Rodriguez, A., Sarda, P., Nessmann, C., Boulot, P., Leger, C.L., Descomps, B. J. Lipid Res. (1998) [Pubmed]
  13. Significant utilization of dietary arachidonic acid is for brain adrenic acid in baboon neonates. Wijendran, V., Lawrence, P., Diau, G.Y., Boehm, G., Nathanielsz, P.W., Brenna, J.T. J. Lipid Res. (2002) [Pubmed]
  14. Effects of n-3 and n-6 fatty acids on tumor necrosis factor cytotoxicity in WEHI fibrosarcoma cells. Brekke, O.L., Espevik, T., Bardal, T., Bjerve, K.S. Lipids (1992) [Pubmed]
  15. Effects of repeated gestation and lactation on milk n-6 fatty acid composition in rats fed on a diet rich in 18:2n-6 or 18:3n-6. Huang, Y.S., Redden, P.R., Horrobin, D.F., Churchill, S., Parker, B., Ward, R.P., Mills, D.E. Br. J. Nutr. (1992) [Pubmed]
  16. Dietary copper deficiency alters protein and lipid composition of murine lymphocyte plasma membranes. Korte, J.J., Prohaska, J.R. J. Nutr. (1987) [Pubmed]
  17. Effect of various steroids on the biosynthesis of arachidonic acid in isolated hepatocytes and HTC cells. Marra, C.A., de Alaniz, M.J., Brenner, R.R. Lipids (1988) [Pubmed]
  18. Microsomal delta 5 desaturation of eicosa-8,11,14-trienoic acid is activated by a cytosolic fraction. Leikin, A.I., Brenner, R.R. Lipids (1989) [Pubmed]
  19. Dietary fats and platelet function among Finnish men. Salo, M.K. Ann. Med. (1989) [Pubmed]
  20. Dose-response effects of dietary gamma-linolenic acid-enriched oils on human polymorphonuclear-neutrophil biosynthesis of leukotriene B4. Ziboh, V.A., Fletcher, M.P. Am. J. Clin. Nutr. (1992) [Pubmed]
  21. Ability of 15-hydroxyeicosatrienoic acid (15-OH-20:3) to modulate macrophage arachidonic acid metabolism. Chapkin, R.S., Miller, C.C., Somers, S.D., Erickson, K.L. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  22. Fatty acyl desaturation in isolated hepatocytes from Atlantic salmon (Salmo salar): stimulation by dietary borage oil containing gamma-linolenic acid. Tocher, D.R., Bell, J.G., Dick, J.R., Sargent, J.R. Lipids (1997) [Pubmed]
  23. Stearidonic acid, an inhibitor of the 5-lipoxygenase pathway. A comparison with timnodonic and dihomogammalinolenic acid. Guichardant, M., Traitler, H., Spielmann, D., Sprecher, H., Finot, P.A. Lipids (1993) [Pubmed]
  24. Effects of dietary supplementation of rapeseed oil on metabolism of [1-14C]18:1n-9, [1-14C]20:3n-6, and [1-14C]20:4n-3 in Atlantic salmon hepatocytes. Moya-Falcón, C., Thomassen, M.S., Jakobsen, J.V., Ruyter, B. Lipids (2005) [Pubmed]
  25. Dietary manipulation of macrophage phospholipid classes: selective increase of dihomogammalinolenic acid. Chapkin, R.S., Somers, S.D., Erickson, K.L. Lipids (1988) [Pubmed]
  26. Changes in the fatty acid composition of preterm and term human milk from 1 week to 6 months of lactation. Luukkainen, P., Salo, M.K., Nikkari, T. J. Pediatr. Gastroenterol. Nutr. (1994) [Pubmed]
  27. Polyunsaturated fatty acids are lower in blood lipids of Usher's type I but not Usher's type II. Maude, M.B., Anderson, E.O., Anderson, R.E. Invest. Ophthalmol. Vis. Sci. (1998) [Pubmed]
  28. Intravenous injection of tridihomo-gamma-linolenoyl-glycerol into mice and its effects on delayed-type hypersensitivity. Taki, H., Nakamura, N., Hamazaki, T., Kobayashi, M. Lipids (1993) [Pubmed]
  29. Effect of dietary fatty acids on delta 5 desaturase activity and biosynthesis of arachidonic acid in rat liver microsomes. de Gomez Dumm, I.N., de Alaniz, M.J., Brenner, R.R. Lipids (1983) [Pubmed]
  30. Changes in plasma phospholipid fatty acids and their relationship to disease activity in rheumatoid arthritis patients treated with a vegetarian diet. Haugen, M.A., Kjeldsen-Kragh, J., Bjerve, K.S., Høstmark, A.T., Førre, O. Br. J. Nutr. (1994) [Pubmed]
  31. Delta 5 desaturase activity in rat kidney microsomes. Irazú, C.E., González-Rodríguez, S., Brenner, R.R. Mol. Cell. Biochem. (1993) [Pubmed]
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