Polyunsaturated fat

Polyunsaturated fats are fats in which the constituent hydrocarbon chain possesses two or more carbon–carbon double bonds.[1][2] Polyunsaturated fat can be found mostly in nuts, seeds, fish, seed oils, and oysters.[1] "Unsaturated" refers to the fact that the molecules contain less than the maximum amount of hydrogen (if there were no double bonds). These materials exist as cis or trans isomers depending on the geometry of the double bond.

Saturated fats have hydrocarbon chains which can be most readily aligned. The hydrocarbon chains in trans fats align more readily than those in cis fats, but less well than those in saturated fats. In general, this means that the melting points of fats increase from cis to trans unsaturated and then to saturated. See the section about the chemical structure of fats for more information.

Chemical structure of the polyunsaturated fat linoleic acid.
3D representation of linoleic acid in a bent conformation.
Chemical structure of alpha-linolenic acid (ALA), an essential omega−3 fatty acid.

The position of the carbon-carbon double bonds in carboxylic acid chains in fats is designated by Greek letters.[1] The carbon atom closest to the carboxyl group is the alpha carbon, the next carbon is the beta carbon and so on. In fatty acids the carbon atom of the methyl group at the end of the hydrocarbon chain is called the omega carbon because omega is the last letter of the Greek alphabet. Omega-3 fatty acids have a double bond three carbons away from the methyl carbon, whereas omega-6 fatty acids have a double bond six carbons away from the methyl carbon. The illustration below shows the omega-6 fatty acid, linoleic acid.

While it is the nutritional aspects of polyunsaturated fats that are generally of greatest interest, these materials also have non-food applications. Drying oils, which polymerize on exposure to oxygen to form solid films, are polyunsaturated fats. The most common ones are linseed (flax seed) oil, tung oil, poppy seed oil, perilla oil, and walnut oil. These oils are used to make paints and varnishes.

Health

Potential benefits

In preliminary research, omega-3 fatty acids in algal oil, fish oil, fish and seafood have been shown to lower the risk of heart attacks.[3] Other preliminary research indicates that omega-6 fatty acids in sunflower oil and safflower oil may also reduce the risk of cardiovascular disease.[4]

Among omega-3 fatty acids, neither long-chain nor short-chain forms were consistently associated with breast cancer risk. High levels of docosahexaenoic acid (DHA), however, the most abundant omega-3 polyunsaturated fatty acid in erythrocyte (red blood cell) membranes, were associated with a reduced risk of breast cancer.[5] The DHA obtained through the consumption of polyunsaturated fatty acids is positively associated with cognitive and behavioral performance.[6] In addition DHA is vital for the grey matter structure of the human brain, as well as retinal stimulation and neurotransmission.[1]

Dietary intake of polyunsaturated fatty acids is under preliminary research to assess the risk of developing amyotrophic lateral sclerosis (motor neurone disease).[7][8]

The importance of the ratio of omega-6/omega-3 essential fatty acids as established by comparative studies shows an omega-6:omega-3 ratio under 4:1 may influence health.[9]

Contrary to conventional advice, an evaluation of evidence from 1966-1973 pertaining to the health impacts of replacing dietary saturated fat with linoleic acid found that participants in the group doing so had increased rates of death from all causes, coronary heart disease, and cardiovascular disease.[10] Although this evaluation was disputed by many scientists,[11] it fueled debate over worldwide dietary advice to substitute polyunsaturated fats for saturated fats.[12]

Pregnancy

Polyunsaturated fat supplementation does not decrease the incidence of pregnancy-related disorders, such as hypertension or preeclampsia, but may increase the length of gestation slightly and decreased the incidence of early premature births.[1]

Expert panels in the United States and Europe recommend that pregnant and lactating women consume higher amounts of polyunsaturated fats than the general population to enhance the DHA status of the fetus and newborn.[1]

Cancer

Results from observational clinical trials on polyunsaturated fat intake and cancer have been inconsistent and vary by numerous factors of cancer incidence, including gender and genetic risk.[3] Some studies have shown associations between higher intakes and/or blood levels of polyunsaturated fat omega-3s and a decreased risk of certain cancers, including breast and colorectal cancer, while other studies found no associations with cancer risk.[3][13]

Food sources

Food sources of polyunsaturated fats include:[1][14]

Food source (100g)Polyunsaturated fat (g)
Walnuts47
Canola Oil34
Sunflower seeds33
Sesame Seeds26
Chia Seeds23.7
Unsalted Peanuts16
Peanut Butter14.2
Avocado Oil13.5 [15]
Olive Oil11
Safflower Oil 12.82[16]
Seaweed11
Sardines5
Soybeans7
Tuna14
Wild Salmon17.3
Whole Grain Wheat9.7

References

  1. 1 2 3 4 5 6 7 "Essential Fatty Acids". Micronutrient Information Center, Oregon State University, Corvallis, OR. May 2014. Retrieved 24 May 2017.
  2. ↑ "Omega-3 fatty acids, fish oil, alpha-linolenic acid". Mayo Clinic. 2017. Retrieved 24 May 2017.
  3. 1 2 3 "Omega-3 Fatty Acids and Health: Fact Sheet for Health Professionals". US National Institutes of Health, Office of Dietary Supplements. 2 November 2016. Retrieved 5 April 2017.
  4. ↑ Willett, Walter C (September 2007). "The role of dietary n-6 fatty acids in the prevention of cardiovascular disease". Journal of Cardiovascular Medicine. 8: S42–5. doi:10.2459/01.JCM.0000289275.72556.13. PMID 17876199.
  5. ↑ Pala, V.; Krogh, V; Muti, P; Chajès, V; Riboli, E; Micheli, A; Saadatian, M; Sieri, S; Berrino, F (July 2001). "Erythrocyte membrane fatty acids and subsequent breast cancer: a prospective Italian study". Journal of the National Cancer Institute. 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870.
  6. ↑ Van De Rest, O.; Geleijnse, J. M.; Kok, F. J.; Van Staveren, W. A.; Dullemeijer, C.; Olderikkert, M.G.M.; Beekman, A. T.F.; De Groot, C. P.G.M. (August 2008). "Effects of Fish Oil on cognitive performance in older subjects". Neurology. 71 (6): 430–38. doi:10.1212/01.wnl.0000324268.45138.86. PMID 18678826.
  7. ↑ Veldink, J H; Kalmijn, S; Groeneveld, G-J; Wunderink, W; Koster, A; De Vries, J H M; Van Der Luyt, J; Wokke, J H J; Van Den Berg, L H (April 2007). "Intake of polyunsaturated fatty acids and vitamin E reduces the risk of developing amyotrophic lateral sclerosis". Journal of Neurology, Neurosurgery, and Psychiatry. 78 (4): 367–71. doi:10.1136/jnnp.2005.083378. PMC 2077791. PMID 16648143.
  8. ↑ Okamoto, Kazushi; Kihira, Tameko; Kondo, Tomoyoshi; Kobashi, Gen; Washio, Masakazu; Sasaki, Satoshi; Yokoyama, Tetsuji; Miyake, Yoshihiro; et al. (October 2007). "Nutritional status and risk of amyotrophic lateral sclerosis in Japan". Amyotrophic Lateral Sclerosis. 8 (5): 300–4. doi:10.1080/17482960701472249. PMID 17852010.
  9. ↑ Simopoulos (October 2002). "The importance of the ratio of omega-6/omega-3 essential fatty acids". The importance of the ratio of omega-6/omega-3 essential fatty acids. National Institutes of Health. 56 (8): 365–79. doi:10.1016/S0753-3322(02)00253-6. PMID 12442909.
  10. ↑ Ramsden, C; Zamora, D; Leelarthaepin, B; Majchrzak-Hong, S; Faurot, K; Suchindran, C; Ringel, A; Davis, J; Hibbeln, J (February 2013). "Use of dietary linoleic acid for secondary prevention of coronary heart disease and death: evaluation of recovered data from the Sydney Diet Heart Study and updated meta-analysis". BMJ Group. 346: e8707. doi:10.1136/bmj.e8707. PMC 4688426. PMID 23386268.
  11. ↑ Interview: Walter Willett (2017). "Research Review: Old data on dietary fats in context with current recommendations: Comments on Ramsden et al. in the British Medical Journal". TH Chan School of Public Health, Harvard University, Boston. Retrieved 24 May 2017.
  12. ↑ Weylandt, K. H.; Serini, S; Chen, Y. Q.; Su, H. M.; Lim, K; Cittadini, A; Calviello, G (2015). "Omega-3 Polyunsaturated Fatty Acids: The Way Forward in Times of Mixed Evidence". BioMed Research International. 2015: 143109. doi:10.1155/2015/143109. PMC 4537707. PMID 26301240.
  13. ↑ Patterson, R. E.; Flatt, S. W.; Newman, V. A.; Natarajan, L; Rock, C. L.; Thomson, C. A.; Caan, B. J.; Parker, B. A.; Pierce, J. P. (2010). "Marine Fatty Acid Intake is Associated with Breast Cancer Prognosis". Journal of Nutrition. 141 (2): 201–206. doi:10.3945/jn.110.128777. PMC 3021439. PMID 21178081.
  14. ↑ "National nutrient database for standard reference, release 23". United States Department of Agriculture, Agricultural Research Service. 2011.
  15. ↑ "Vegetable oil, avocado Nutrition Facts & Calories". nutritiondata.self.com.
  16. ↑ "United States Department of Agriculture – National Nutrient Database". Sep 8, 2015.
  17. 1 2 3 4 5 Anderson. "Fatty acid composition of fats and oils" (PDF). UCCS. Retrieved April 8, 2017.
  18. ↑ "NDL/FNIC Food Composition Database Home Page". Nal.usda.gov. Retrieved May 21, 2013.
  19. ↑ USDA → Basic Report: 04042, Oil, peanut, salad or cooking Retrieved on January 16, 2015
  20. ↑ nutritiondata.com → Oil, vegetable safflower, oleic Retrieved on April 10, 2017
  21. ↑ nutritiondata.com → Oil, vegetable safflower, linoleic Retrieved on April 10, 2017
  22. ↑ nutritiondata.com → Oil, vegetable, sunflower Retrieved on September 27, 2010
  23. ↑ USDA Basic Report Cream, fluid, heavy whipping
  24. ↑ "Nutrition And Health". The Goose Fat Information Service.
  25. ↑ nutritiondata.com → Egg, yolk, raw, fresh Retrieved on August 24, 2009
  26. ↑ "09038, Avocados, raw, California". National Nutrient Database for Standard Reference, Release 26. United States Department of Agriculture, Agricultural Research Service. Retrieved 14 August 2014.
  27. ↑ "Feinberg School > Nutrition > Nutrition Fact Sheet: Lipids". Northwestern University. Archived from the original on 2011-07-20.
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