Tricosanoic acid is an 23-carbon, odd-chain saturated fat (23:0) synthesized initially from propionic acid and can be derived in the diet from sesame, sunflower, and hempseed oils. It can furthermore be found in milk and dairy products, as well as some wild mushroom species. It can also be endogenously made.
Most research in fatty acid metabolism has focused on even-chain fatty acids since they represent >99% of total human lipid concentration. For years, it had been concluded that odd chain saturated fatty acids (OCSFAs) were of little significance and used only as internal standards in laboratory methodology. However, there is now a realization that they are, in fact, relevant and important physiologically.
OCS-FAs mainly originate from dairy fat since microbiome fermentation in ruminant animals is a primary source of production. The human body can also synthesize them by elongating propionic acid, a short chain fatty acid formed in the microbiome. New research is showing they may also be formed by shortening VLCFAs by removing carbon molecules using α-oxidation. Metabolism of OCS-FAs is a bit different than even-numbered chained fatty acids. Both odd and even chain fatty acids undergo oxidation, though OCS-FAs produce a molecule of propionyl-CoA and a molecule of acetyl-CoA instead of two acetyl-CoAs. Propionyl-CoA requires a vitamin B12-dependent enzyme to be converted into succinyl-CoA and used in the citric acid cycle. It should be noted that the microbiome is not the only source for the OCS-FA precursor propionate. Endogenous propionate can be produced by the degradation of some amino acids, which can then lead to OCS-FA production.
Several epidemiologic studies show a positive association between OCS-FA and reduced risk for inflammation, cardiometabolic disease, multiple sclerosis, and nonalcoholic steatohepatitis. They are also being studied as adjuvant therapies in cancer due to their cell signaling properties which induce targeted apoptosis. Additionally, it has been found that OCS-FAs increase membrane fluidity more than PUFAs, and they are being studied as a form of treatment for Alzheimer’s disease.
References:
- Senila L, Neag E, Cadar O, Kovacs MH, Becze A, Senila M. Chemical, Nutritional and Antioxidant Characteristics of Different Food Seeds. Applied Sciences. 2020;10(5):1589.
- Liu M, Zuo LS, Sun TY, et al. Circulating Very-Long-Chain Saturated Fatty Acids Were Inversely Associated with Cardiovascular Health: A Prospective Cohort Study and Meta-Analysis. Nutrients. 2020;12(9).
- Tsou P-L, Wu C-J. Sex-dimorphic association of plasma fatty acids with cardiovascular fitness in young and middleaged general adults: subsamples from nhanes 2003–2004. Nutrients. 2018;10(10):1558.
- Ardisson Korat AV, Malik VS, Furtado JD, et al. Circulating Very-Long-Chain SFA Concentrations Are Inversely Associated with Incident Type 2 Diabetes in US Men and Women. The Journal of Nutrition. 2019;150(2):340-349.
- Lee YS, Cho Y, Shin MJ. Dietary Very Long Chain Saturated Fatty Acids and Metabolic Factors: Findings from the Korea National Health and Nutrition Examination Survey 2013. Clinical nutrition research. 2015;4(3):182-189.
- Lemaitre RN, Jensen PN, Hoofnagle A, et al. Plasma Ceramides and Sphingomyelins in Relation to Heart Failure Risk: The Cardiovascular Health Study. Circulation: Heart Failure. 2019;12(7):e005708.
- Lemaitre RN, King IB, Rice K, et al. Erythrocyte very long-chain saturated fatty acids associated with lower risk of incident sudden cardiac arrest. Prostaglandins, Leukotrienes and Essential Fatty Acids. 2014;91(4):149-153.
- Li D, Misialek JR, Jing M, et al. Plasma phospholipid verylong-chain SFAs in midlife and 20-year cognitive change in the Atherosclerosis Risk in Communities (ARIC): a cohort study. The American journal of clinical nutrition. 2020;111(6):1252-1258.
Decreased dietary intake of these saturated fatty acids, or avoidance of products containing them, can result in low levels. Some VLSFAs can be synthesized from other fatty acids. Therefore, decreased levels of precursors, lack of vitamin and mineral cofactors, or SNPs in the elongase enzyme may also contribute to low levels. Specific deficiency in VLSFAs is not well studied. Though, due to their importance in brain development and their associations with improved health outcomes, as outlined above, research is evolving.
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Intake of foods containing these VLSFAs or use of products containing them can contribute to higher levels. Increased intake of precursor fatty acids, or SNPs in the elongase enzyme, may alter levels.
Additionally, as an odd-chain fatty acid, tricosanoic acid elevations can be seen with functional deficiency of vitamin B12 since it is required for the conversion of propionate for oxidation. Tricosanoic acid can be high in microbiome dysbiosis with increased production of the short chain fatty acid propionate (its precursor).
The health implications of elevated VLSFAs levels are evolving, though they are generally found to be beneficial in health and aging. Several meta-analyses suggest a beneficial association of very long chained saturated fatty acids with cardiovascular health outcomes as well as lower risks of type 2 diabetes, atrial fibrillation, heart failure, and coronary disease. These VLSFAs may also be important in neural development and cognition. The mechanisms of these very long chained saturated fatty acids are not fully known. Because VLSFAs are components of ceremides involved in apoptosis, there is strong evidence that VLSFAs are protective against apoptosis and cell death.
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% Omega-3s, % Omega-6s, % Omega-9s, % Saturated Fats, 1-Methylhistidine, 3-Hydroxyisovaleric Acid, 3-Hydroxyphenylacetic Acid, 3-Hydroxypropionic Acid, 3-Methyl-4-OH-phenylglycol, 3-Methylhistidine, 4-Hydroxyphenylacetic Acid, 5-OH-indoleacetic Acid, 8-OHdG (urine), a-Amino-N-butyric Acid, a-Aminoadipic Acid, a-Hydroxybutyric Acid, a-Hydroxyisobutyric Acid (from MTBE), a-Keto-b-Methylvaleric Acid, a-Ketoadipic Acid, a-Ketoglutaric Acid, a-Ketoisocaproic Acid, a-Ketoisovaleric Acid, a-Ketophenylacetic Acid (from Styrene), a-Linolenic (ALA) 18:3 n3, AA / EPA (20:4 n6 / 20:5 n3), Adipic Acid, Alanine, Aluminum, Anserine (dipeptide), Antimony, Arachidic C20:0, Arachidonic (AA) 20:4 n6, Arginine, Arsenic, Asparagine, Aspartic Acid, b-Alanine, b-Aminoisobutyric Acid, b-OH-b-Methylglutaric Acid, b-OH-Butyric Acid, Barium, Behenic C22:0, Benzoic Acid, Bismuth, Cadmium, Calcium, Carnosine (dipeptide), Cesium, Chromium, cis-Aconitic Acid, Citramalic Acid, Citric Acid, Citrulline, Cobalt, Copper, Creatinine, Creatinine Concentration (Amino Acids FMV), Cystathionine, Cysteine, Cystine, D-Arabinitol, Dihomo-g-linolenic (DGLA) 20:3 n6, Dihydroxyphenylpropionic Acid (DHPPA), Docosahexaenoic (DHA) 22:6 n3, Docosapentaenoic (DPA) 22:5 n3, Docosatetraenoic (DTA) 22:4 n6, Eicosadienoic 20:2 n6, Eicosapentaenoic (EPA) 20:5 n3, Elaidic 18:1 n9t, Ethanolamine, Formiminoglutamic Acid (FIGlu), g-Aminobutyric Acid, g-Linolenic (GLA) 18:3 n6, Gadolinium, Gallium, Glutamic Acid, Glutamine, Glutaric Acid, Glyceric Acid, Glycine, Glycolic Acid, Hippuric Acid, Histidine, Homovanillic Acid, Indoleacetic Acid, Iron, Isocitric Acid, Isoleucine, Isovalerylglycine, Kynurenic / Quinolinic Ratio, Kynurenic Acid, Lactic Acid, Lead, Leucine, Lignoceric C24:0, Linoleic (LA) 18:2 n6, Linoleic / DGLA (18:2 n6 / 20:3 n6), Lipid Peroxides (urine), Lithium, Lysine, Magnesium, Malic Acid, Manganese, Margaric C17:0, Mercury, Methionine, Methylmalonic Acid, Molybdenum, Nervonic 24:1 n9, Nickel, Niobium, Oleic 18:1 n9, Omega-3 Index, Omega-6s /Omega-3s, Ornithine, Orotic Acid, Oxalic Acid, Palmitic C16:0, Palmitoleic 16:1 n7, Pentadecanoic C15:0, Phenylacetic Acid, Phenylalanine, Phosphoethanolamine, Phosphoserine, Platinum, Potassium, Proline, Pyroglutamic Acid, Pyruvic Acid, Quinolinic Acid, Rubidium, Sarcosine, Selenium, Serine, Stearic C18:0, Strontium, Suberic Acid, Succinic Acid, Sulfur, Tartaric Acid, Taurine, Thallium, Thorium, Threonine, Tin, Tricosanoic C23:0, Tryptophan, Tungsten, Tyrosine, Uranium, Urea, Urine Creatinine, Vaccenic 18:1 n7, Valine, Vanadium, Vanilmandelic Acid, Xanthurenic Acid, Zinc