The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

AG-C-24610     octadeca-9,12,15-trienoic acid

Synonyms: AG-E-90690, AG-F-59439, KBioGR_000096, KBioSS_000096, ANW-73133, ...
 
 
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.
 

Disease relevance of linolenic acid

  • A high alpha-linolenate diet suppresses antigen-induced immunoglobulin E response and anaphylactic shock in mice [1].
  • These results, together with the reported suppressive effects of a high alpha-linolenate diet on the formation of lipid-derived allergic mediators, support the hypothesis that raising the (n-3) to (n-6) ratios of diets would be effective in reducing the severity of immediate-type allergic hypersensitivity [1].
  • Our results indicate that dietary enrichment with alpha-linolenate causes unfavorable effects in this anti-GBM nephritis model [2].
  • 3. The proliferative response to the purified protein derivative of Mycobacterium tuberculosis was inhibited by all of the polyunsaturated fatty acids tested, except alpha-linolenate, and also by stearate [3].
  • Mice were fed diets with three different ratios of alpha-linolenate (18:3n-3) to linoleate (18:2n-6), and the severity of hepatitis during endotoxic shock was compared [4].
 

Psychiatry related information on linolenic acid

 

High impact information on linolenic acid

 

Chemical compound and disease context of linolenic acid

  • In agreement with in vitro study, our present study demonstrates that dietary high alpha-linolenate suppresses PAF production in rat kidney during systemic endotoxemia, and which is mainly due to the decrease in alkylacyl-GPC content, altered fatty acid compositions of the precursor lipids and lower CoA-independent transacylase activity [12].
 

Biological context of linolenic acid

  • These results indicate that carbon from alpha-linolenate is not exclusively conserved for synthesis of longer n-3 polyunsaturates but is a readily accessible carbon source for de novo lipogenesis during early brain development in the suckling rat [13].
  • The ALA-rich diet tripled the percentage of platelet EPA, (P < 0.0005) but had little effect on coagulation and fibrinolysis [14].
  • Previous studies demonstrated that high levels of alpha-linolenate in cell membranes of potato tubers (achieved by overexpressing fatty acid desaturases) enhances lipid peroxidation, oxidative stress, and tuber metabolic rate, effectively accelerating the physiological age of tubers [15].
  • In cultures competent to undergo sexual development, alpha-linoleate was the predominant fatty acid, ranging from 53 to 65% of the total fatty acid mass. alpha-Linolenate was 3% or less of the total fatty acid, in marked contrast to the much higher levels (10-35%) typically reported for vegetative cultures [16].
  • The results indicate that the effects of specific PUFA contained in BSO on lipid metabolism are different from those of LA and ALA [17].
 

Anatomical context of linolenic acid

 

Associations of linolenic acid with other chemical compounds

 

Gene context of linolenic acid

  • The APC ratio demonstrated increased anticoagulant activity on the ALA-rich diet (P < 0.001) only [14].
  • When the intracellular free Ca2+ concentration [( Ca2+]i) returned to basal level, fatty acid free bovine serum albumin (BSA) was added to remove extracellular and membrane bound ALA [24].
  • The whole body Cho content was significantly lower, by 28%, in the high alpha-linolenate group compared with the high linoleate group, but the total lipid content, PL and neutral lipids were similar between the groups [25].
  • Thus, ALA and EPA inhibit antioxidant defenses of the cell and damage the DNA, which can ultimately lead to tumor cell lysis [26].
  • Effect of dietary alpha-linolenate/linoleate balance on lipopolysaccharide-induced tumor necrosis factor production in mouse macrophages [27].
 

Analytical, diagnostic and therapeutic context of linolenic acid

  • Ligation of the CD3 complex of the T cell antigen receptor with an anti-CD3 antibody (OKT3) during the sustained [Ca2+]i increased (induced by a sub-optimal concentration of ALA), produced a greater response [24].
  • Analysis of pooled skin specimens from a previous study in which weanling rats were fed a fat-free diet and supplemented orally with pure alpha-linolenate for 13 weeks (Hansen, H.S. and Jensen, B. (1983) Lipids 18, 682-690) revealed very little polyunsaturated fatty acid in the two sphingolipids [28].

References

  1. A high alpha-linolenate diet suppresses antigen-induced immunoglobulin E response and anaphylactic shock in mice. Watanabe, S., Sakai, N., Yasui, Y., Kimura, Y., Kobayashi, T., Mizutani, T., Okuyama, H. J. Nutr. (1994) [Pubmed]
  2. Effect of dietary alpha-linolenate/linoleate balance on crescent type-anti-glomerular basement membrane nephritis in rats. Watanabe, S., Suzuki, E., Kojima, R., Suzuki, Y., Okuyama, H. Lipids (1990) [Pubmed]
  3. Polyunsaturated fatty acids suppress human peripheral blood lymphocyte proliferation and interleukin-2 production. Calder, P.C., Newsholme, E.A. Clin. Sci. (1992) [Pubmed]
  4. Effect of dietary alpha-linolenate/linoleate balance on endotoxin-induced hepatitis in mice. Watanabe, S., Okuyama, H. Lipids (1991) [Pubmed]
  5. Versatile roles of docosahexaenoic acid in the prenatal brain: From pro- and anti-oxidant features to regulation of gene expression. Yavin, E. Prostaglandins Leukot. Essent. Fatty Acids (2006) [Pubmed]
  6. alpha-linolenate-deficiency-induced alterations in brightness discrimination learning behavior and retinal function in rats. Okuyama, H., Ohishi, M., Fukuma, A., Sato, Y., Ikemoto, A., Fujii, Y. World review of nutrition and dietetics. (2001) [Pubmed]
  7. Effects of dietary vegetable oils on behavior and drug responses in mice. Kameyama, T., Ohhara, T., Nakashima, Y., Naito, Y., Huang, M.Z., Watanabe, S., Kobayashi, T., Okuyama, H., Yamada, K., Nabeshima, T. Biol. Pharm. Bull. (1996) [Pubmed]
  8. 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]
  9. Mutants of Arabidopsis deficient in the synthesis of alpha-linolenate. Biochemical and genetic characterization of the endoplasmic reticulum linoleoyl desaturase. Browse, J., McConn, M., James, D., Miquel, M. J. Biol. Chem. (1993) [Pubmed]
  10. Effect of dietary alpha-linolenate on platelet-activating factor production in rat peritoneal polymorphonuclear leukocytes. Horii, T., Satouchi, K., Kobayashi, Y., Saito, K., Watanabe, S., Yoshida, Y., Okuyama, H. J. Immunol. (1991) [Pubmed]
  11. Nutritional attributes of traditional flaxseed in healthy young adults. Cunnane, S.C., Hamadeh, M.J., Liede, A.C., Thompson, L.U., Wolever, T.M., Jenkins, D.J. Am. J. Clin. Nutr. (1995) [Pubmed]
  12. Dietary alpha-linolenate suppresses endotoxin-induced platelet-activating factor production in rat kidney. Oh-hashi, K., Takahashi, T., Tanabe, A., Watanabe, S., Okuyama, H. Lipids (1999) [Pubmed]
  13. Recycling of carbon into lipids synthesized de novo is a quantitatively important pathway of alpha-[U-13C]linolenate utilization in the developing rat brain. Menard, C.R., Goodman, K.J., Corso, T.N., Brenna, J.T., Cunnane, S.C. J. Neurochem. (1998) [Pubmed]
  14. Comparison of the effects of two low fat diets with different alpha-linolenic:linoleic acid ratios on coagulation and fibrinolysis. Allman-Farinelli, M.A., Hall, D., Kingham, K., Pang, D., Petocz, P., Favaloro, E.J. Atherosclerosis (1999) [Pubmed]
  15. Lipid metabolism during aging of high-alpha-linolenate-phenotype potato tubers. Zabrouskov, V., Knowles, N.R. Arch. Biochem. Biophys. (2002) [Pubmed]
  16. Changes in fatty acid composition of Neurospora crassa accompany sexual development and ascospore germination. Goodrich-Tanrikulu, M., Howe, K., Stafford, A., Nelson, M.A. Microbiology (Reading, Engl.) (1998) [Pubmed]
  17. 5c,11c,14c-eicosatrienoic acid and 5c,11c,14c,17c-eicosatetraenoic acid of Biota orientalis seed oil affect lipid metabolism in the rat. Ikeda, I., Oka, T., Koba, K., Sugano, M., Lie Ken Jie, M.S. Lipids (1992) [Pubmed]
  18. Regulation by dietary essential fatty acid balance of tumor necrosis factor production in mouse macrophages. Watanabe, S., Onozaki, K., Yamamoto, S., Okuyama, H. J. Leukoc. Biol. (1993) [Pubmed]
  19. Synaptic vesicle ultrastructural changes in the rat hippocampus induced by a combination of alpha-linolenate deficiency and a learning task. Yoshida, S., Yasuda, A., Kawazato, H., Sakai, K., Shimada, T., Takeshita, M., Yuasa, S., Kobayashi, T., Watanabe, S., Okuyama, H. J. Neurochem. (1997) [Pubmed]
  20. Pathway of alpha-linolenic acid through the mitochondrial outer membrane in the rat liver and influence on the rate of oxidation. Comparison with linoleic and oleic acids. Clouet, P., Niot, I., Bézard, J. Biochem. J. (1989) [Pubmed]
  21. Maternal Parity and Diet (n-3) Polyunsaturated Fatty Acid Concentration Influence Accretion of Brain Phospholipid Docosahexaenoic Acid in Developing Rats. Ozias, M.K., Carlson, S.E., Levant, B. J. Nutr. (2007) [Pubmed]
  22. Adipose hormone-sensitive lipase preferentially releases polyunsaturated fatty acids from triglycerides. Gavino, V.C., Gavino, G.R. Lipids (1992) [Pubmed]
  23. Dietary polyunsaturated Fatty acids in gestation alter fetal cortical phospholipids, Fatty acids and phosphatidylserine synthesis. Tam, O., Innis, S.M. Dev. Neurosci. (2006) [Pubmed]
  24. Ca2+ entry in T cells is activated by emptying the inositol 1,4,5-triphosphate sensitive Ca2+ pool. Chow, S.C., Jondal, M. Cell Calcium (1990) [Pubmed]
  25. Lipid lowering effects of high linoleate and high alpha-linolenate diets in rats and mice. Consequence of long-term feedings. Sakai, K., Shimokawa, T., Kobayashi, T., Okuyama, H. Chem. Pharm. Bull. (1992) [Pubmed]
  26. Free radical-dependent suppression of growth of mouse myeloma cells by alpha-linolenic and eicosapentaenoic acids in vitro. Kumar, G.S., Das, U.N. Cancer Lett. (1995) [Pubmed]
  27. Effect of dietary alpha-linolenate/linoleate balance on lipopolysaccharide-induced tumor necrosis factor production in mouse macrophages. Watanabe, S., Hayashi, H., Onozaki, K., Okuyama, H. Life Sci. (1991) [Pubmed]
  28. Essential function of linoleic acid esterified in acylglucosylceramide and acylceramide in maintaining the epidermal water permeability barrier. Evidence from feeding studies with oleate, linoleate, arachidonate, columbinate and alpha-linolenate. Hansen, H.S., Jensen, B. Biochim. Biophys. Acta (1985) [Pubmed]
 
WikiGenes - Universities