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Chemical Compound Review

VACCENIC ACID     (E)-octadec-11-enoic acid

Synonyms: AG-G-69788, CHEBI:28727, CHEBI:36023, C18:1 trans-11, Ambap143-25-9, ...
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Disease relevance of VACCENIC ACID


High impact information on VACCENIC ACID

  • A deletion of nodE resulted in the absence of C16:2 and C16:3 fatty acids, which were replaced by vaccenic acid (delta 11-C18:1), but did not change the proportion of (omega-1)-hydroxylated fatty acids [6].
  • The strain with the R. tropici nodA gene produced Nod factors acylated by vaccenic acid, instead of the C16 unsaturated or hydroxylated fatty acids characteristic of R. meliloti Nod factors, and infected and nodulated alfalfa with a significant delay [2].
  • In synaptosomal brain membranes, the addition of oleic acid (cis), elaidic acid (trans), and the cis and trans isomers of vaccenic acid, at a concentration of 0.87 mumol of lipid/mg of protein, strongly reduced the Bmax and, to a lesser degree, the binding affinity of the mu-selective opioid [3H]Tyr-D-Ala-Gly-(Me)Phe-Gly-ol ([3H]DAMGO) [7].
  • Diets rich in conjugated linoleic acid and vaccenic acid have no effect on blood pressure and isobaric arterial elasticity in healthy young men [8].
  • The crystal structure of Blc with vaccenic acid, an unsaturated C18 fatty acid, reveals that the binding site spans across the Blc dimer, opposite to its membrane anchored face [9].

Biological context of VACCENIC ACID

  • The objective of this study was to examine the effect on blood pressure (BP) and isobaric arterial elasticity (AE), as a measure of arterial health, of a commercial mixture of conjugated linoleic acids (CLA) and of milk fat produced through livestock feeding to have a high content of vaccenic acid (VA) [8].
  • Analysis of Delta AUC for the 6-h postprandial period of selected and total fatty acids showed a lower concentration of vaccenic acid (P = 0.002) after the DAG bolus diet [10].
  • The aims of this study were to determine whether vaccenic acid (VA; t11-18:1) is converted to c9,t11-CLA in human mammary (MCF-7) and colon (SW480) cancer cell lines and whether VA influences cell viability and other CLA-bioresponsive markers [11].
  • Effects of dietary cis 9, trans 11-18:2, trans 10, cis 12-18:2, or vaccenic acid (trans 11-18:1) during lactation on body composition, tissue fatty acid profiles, and litter growth in mice [12].
  • We may conclude that a regular intake of CLA, or/and vaccenic acid as its precursor, should work as an excellent preventive agent by modulating lipid metabolism in target tissues thus conferring protection against the attack of insults of different type [13].

Anatomical context of VACCENIC ACID


Associations of VACCENIC ACID with other chemical compounds


Gene context of VACCENIC ACID

  • These findings suggest that increased PUFA may limit ruminal production of CLA and trans-vaccenic acid (VA) and/or may depress stearoyl-CoA desaturase expression or activity in lean tissues, which in turn limits CLA formation and accretion in tissues [19].

Analytical, diagnostic and therapeutic context of VACCENIC ACID


  1. Biohydrogenation of unsaturated fatty acids. Hydrogenation by cell-free preparations of Butyrivibrio fibrisolvens. Hunter, W.J., Baker, F.C., Rosenfeld, I.S., Keyser, J.B., Tove, S.B. J. Biol. Chem. (1976) [Pubmed]
  2. The NodA proteins of Rhizobium meliloti and Rhizobium tropici specify the N-acylation of Nod factors by different fatty acids. Debellé, F., Plazanet, C., Roche, P., Pujol, C., Savagnac, A., Rosenberg, C., Promé, J.C., Dénarié, J. Mol. Microbiol. (1996) [Pubmed]
  3. Effects of butter high in ruminant trans and monounsaturated fatty acids on lipoproteins, incorporation of fatty acids into lipid classes, plasma C-reactive protein, oxidative stress, hemostatic variables, and insulin in healthy young men. Tholstrup, T., Raff, M., Basu, S., Nonboe, P., Sejrsen, K., Straarup, E.M. Am. J. Clin. Nutr. (2006) [Pubmed]
  4. Synthesis and utilization of fatty acids by wild-type and fatty acid auxotrophs of Caulobacter crescentus. Letts, V., Shaw, P., Shapiro, L., Henry, S. J. Bacteriol. (1982) [Pubmed]
  5. Fatty acid profiles of nitrite-oxidizing bacteria reflect their phylogenetic heterogeneity. Lipski, A., Spieck, E., Makolla, A., Altendorf, K. Syst. Appl. Microbiol. (2001) [Pubmed]
  6. Role of the Rhizobium meliloti nodF and nodE genes in the biosynthesis of lipo-oligosaccharidic nodulation factors. Demont, N., Debellé, F., Aurelle, H., Dénarié, J., Promé, J.C. J. Biol. Chem. (1993) [Pubmed]
  7. Modulation of opioid receptor binding by cis and trans fatty acids. Remmers, A.E., Nordby, G.L., Medzihradsky, F. J. Neurochem. (1990) [Pubmed]
  8. Diets rich in conjugated linoleic acid and vaccenic acid have no effect on blood pressure and isobaric arterial elasticity in healthy young men. Raff, M., Tholstrup, T., Sejrsen, K., Straarup, E.M., Wiinberg, N. J. Nutr. (2006) [Pubmed]
  9. The membrane bound bacterial lipocalin Blc is a functional dimer with binding preference for lysophospholipids. Campanacci, V., Bishop, R.E., Blangy, S., Tegoni, M., Cambillau, C. FEBS Lett. (2006) [Pubmed]
  10. Diacylglycerol oil does not affect portal vein transport of nonesterified fatty acids but decreases the postprandial plasma lipid response in catheterized pigs. Kristensen, J.B., Jørgensen, H., Mu, H. J. Nutr. (2006) [Pubmed]
  11. Vaccenic acid (t11-18:1) is converted to c9,t11-CLA in MCF-7 and SW480 cancer cells. Miller, A., McGrath, E., Stanton, C., Devery, R. Lipids (2003) [Pubmed]
  12. Effects of dietary cis 9, trans 11-18:2, trans 10, cis 12-18:2, or vaccenic acid (trans 11-18:1) during lactation on body composition, tissue fatty acid profiles, and litter growth in mice. Loor, J.J., Lin, X., Herbein, J.H. Br. J. Nutr. (2003) [Pubmed]
  13. Modulation of lipid metabolism and vitamin A by conjugated linoleic acid. Carta, G., Angioni, E., Murru, E., Melis, M.P., Spada, S., Banni, S. Prostaglandins Leukot. Essent. Fatty Acids (2002) [Pubmed]
  14. Butter naturally enriched in conjugated linoleic acid and vaccenic acid alters tissue fatty acids and improves the plasma lipoprotein profile in cholesterol-fed hamsters. Lock, A.L., Horne, C.A., Bauman, D.E., Salter, A.M. J. Nutr. (2005) [Pubmed]
  15. Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland. Banni, S., Angioni, E., Murru, E., Carta, G., Melis, M.P., Bauman, D., Dong, Y., Ip, C. Nutrition and cancer. (2001) [Pubmed]
  16. Effects of forage and sunflower oil levels on ruminal biohydrogenation of fatty acids and conjugated linoleic acid formation in beef steers fed finishing diets. Sackmann, J.R., Duckett, S.K., Gillis, M.H., Realini, C.E., Parks, A.H., Eggelston, R.B. J. Anim. Sci. (2003) [Pubmed]
  17. Long-Term exposure of INS-1 cells to cis and trans fatty acids influences insulin release and fatty acid oxidation differentially. Alstrup, K.K., Brock, B., Hermansen, K. Metab. Clin. Exp. (2004) [Pubmed]
  18. Trans-octadecenoic acids and milk fat depression in lactating dairy cows. Griinari, J.M., Dwyer, D.A., McGuire, M.A., Bauman, D.E., Palmquist, D.L., Nurmela, K.V. J. Dairy Sci. (1998) [Pubmed]
  19. Effectiveness of short-term feeding strategies for altering conjugated linoleic acid content of beef. Griswold, K.E., Apgar, G.A., Robinson, R.A., Jacobson, B.N., Johnson, D., Woody, H.D. J. Anim. Sci. (2003) [Pubmed]
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