Vaccenic acid explained

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt.[1] [2] Trans fat in human milk may depend on trans fat content in food.[3]

Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).[4]

Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid,[5] [6] where it shows anticarcinogenic properties.[7]

Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.[8] Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked,[9] indicating that it is stockpiled similarly to omega-3 fatty acids.

Health

Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable shortenings, or a mixture of pork lard and soy fat, by lowering total LDL and triglyceride levels.[10] [11] [12] [13] [14] A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL.[15]

Obese rats fed a diet enriched with vaccenic acid for 16 weeks had a reduction in total cholesterol, LDL cholesterol and lower triglyceride levels,[16] with an effect comparable to CLA. This effect was not seen in lean rats.[17]

Vaccenic acid accumulates in the orbitofrontal cortex to a higher extent in patients with bipolar disorder and schizophrenia.[18] [19]

Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may be the cause of the phenomenon commonly known as old person smell.[20]

Alkaline phosphatase was inhibited 25% by vaccenic acid in osteoblasts.[21]

A 2023 University of Chicago study found that trans-vaccenic acid enhances anti-tumor immunity by activating CD8+ T cells. This effect is accomplished by deactivating a GPR43 receptor, which activates the CREB pathway instead. The effect was produced with a diet containing 1% w/w TVA.[22]

Notes and References

  1. Web site: Now there are good trans fats? . Bowerman . Susan . May 19, 2008 . Los Angeles Times.
  2. Precht D, Molkentin J . August 1999 . C18:1, C18:2 and C18:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids . Nahrung . 43 . 4 . 233–44 . 10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B . 10481820.
  3. Friesen R, Innis SM . October 2006 . Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling . J. Nutr. . 136 . 10 . 2558–61 . 10.1093/jn/136.10.2558 . 16988126 . free.
  4. Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F . 2005 . Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats . . 88 . 449 . 449 . 10.3168/jds.S0022-0302(05)72705-3 . 15653508 . free.
  5. Web site: cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat . Bauman, Dale . https://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm . 2006-09-07 . 2007-01-15.
  6. Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C . 2001 . Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland . Nutr Cancer . 41 . 1–2 . 91–7 . 10.1080/01635581.2001.9680617 . 12094634. 2920114 .
  7. Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C . October 1, 2004 . The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats . J Nutr . 134 . 10 . 2698–704 . 10.1093/jn/134.10.2698 . 15465769 . 2007-01-15. free .
  8. Web site: Seed Oil Fatty Acids Database . Federal Research Centre for Nutrition and Food - Institute for Lipid Research.
  9. Bainbridge . Melissa L. . Cersosimo . Laura M. . Wright . André-Denis G. . Kraft . Jana . 2016-03-01 . Brockmann . Gudrun A. . Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow . PLOS ONE . en . 11 . 3 . e0150386 . 10.1371/journal.pone.0150386 . free . 1932-6203 . 4773160 . 26930646. 2016PLoSO..1150386B .
  10. http://www.redorbit.com/news/health/2608879/trans-fats-from-ruminant-animals-may-be-beneficial Trans Fats From Ruminant Animals May Be Beneficial – Health News
  11. The Journal of Nutrition. 140. 1. Jan 2010. 18–24. 19923390. 10.3945/jn.109.105163. Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr-/- Mice. Bassett. C. M. C.. Edel. A. L.. Patenaude. A. F.. McCullough. R. S.. Blackwood. D. P.. Chouinard. P. Y.. Paquin. P.. Lamarche. B.. Pierce. G. N.. free.
  12. University of Alberta. Natural trans fats have health benefits, University of Alberta study shows. 2 April 2008. Wang. Flora. Proctor. Spencer. amp.
  13. Wang Y, Jacome-Sosa MM, Vine DF, Proctor SD . Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans-fats to improve CVD risk. 20 May 2010. Lipid Technology. 22. 5. 103–106. 10.1002/lite.201000016.
  14. Bassett C, Edel AL, Patenaude AF, McCullough RS, Blackwood DP, Chouinard PY, Paquin P, Lamarche B, Pierce GN . Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr−/− Mice. 2010. The Journal of Nutrition. 140. 1. 18–24. 10.3945/jn.109.105163. 19923390. free.
  15. David J. Baer, PhD. US Department of Agriculture, Agricultural Research Service, Beltsville Human Nutrition Research Laboratory. New Findings on Dairy Trans Fat and Heart Disease Risk, IDF World Dairy Summit 2010, 8–11 November 2010. Auckland, New Zealand
  16. AFNS. Alberta natural trans fat research earns global recognition . April 2, 2008.
  17. Wang . Ye . Jacome-Sosa . M. Miriam . Vine . Donna F. . Proctor . Spencer D. . May 2010 . Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans -fats to improve CVD risk . Lipid Technology . en . 22 . 5 . 103–106 . 10.1002/lite.201000016 . 0956-666X.
  18. McNamara . RK . Jandacek . R . Rider . T . Tso . P . Hahn . CG . Richtand . NM . Stanford . KE . 2007 . Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications . Schizophr Res . 91 . 1–3 . 37–50 . 10.1016/j.schres.2006.11.027 . 1853256 . 17236749.
  19. McNamara . RK . Jandacek . R . Rider . T . Tso . P . Stanford . KE . Hahn . CG . Richtand . NM . 2008 . Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder . Psychiatry Research . 160 . 3 . 285–299 . 10.1016/j.psychres.2007.08.021 . 2620106 . 18715653.
  20. Haze S, Gozu Y, Nakamura S, Kohno Y, Sawano K, Ohta H, Yamazaki K . April 2001 . 2-Nonenal newly found in human body odor tends to increase with aging . J. Invest. Dermatol. . 116 . 4 . 520–4 . 10.1046/j.0022-202x.2001.01287.x . 11286617. free .
  21. Hamazaki K, Suzuki N, Kitamura K, Hattori A, Nagasawa T, Itomura M, Hamazaki T . June 2016 . Is vaccenic acid (18:1t n-7) associated with an increased incidence of hip fracture? An explanation for the calcium paradox . Prostaglandins Leukot. Essent. Fatty Acids . 109 . 8–12 . 10.1016/j.plefa.2016.04.001 . 27269708.
  22. Fan H, Xia S, Xiang J et al. . Trans-vaccenic acid reprograms CD8+ T cells and anti-tumour immunity . 22 November 2023 . Nature . 623 . 7989 . 1034–1043 . 10.1038/s41586-023-06749-3. free . 37993715 . 10686835 .

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