Dihomo-gamma-linolenic acid (DGLA) is a 20-carbon omega-6 with 3 double bonds (20:3n6) derived from the essential linolenic acid. LA is metabolized to GLA, which is rapidly elongated to DGLA. There are only trace amounts of DGLA found in organ meats, otherwise it must be synthesized from GLA. The inability to convert precursor fatty acids to DGLA is associated with various pathologic and physiologic conditions such as aging, diabetes, alcoholism, atopic dermatitis, rheumatoid arthritis, cancer, and cardiovascular disease.
DGLA is a precursor to prostaglandin PGE1, which inhibits platelet aggregation and inflammation, produces vasodilation, inhibits cholesterol biosynthesis and thrombus formation, regulates immune responses and reduces blood pressure. It is also involved in inhibiting the formation of pro-inflammatory compounds from AA. PGE1 can also inhibit growth and differentiation of cancer cells. Although the mechanism of DGLA in cancer has not yet been identified, the potential benefits are being studied. DGLA-enriched oils and fermented DGLA oil supplements are being developed with excellent safety profiles and studied in a variety of clinical conditions.
References:
- Wang X, Lin H, Gu Y. Multiple roles of dihomo-γ-linolenic acid against proliferation diseases. Lipids in Health and Disease. 2012;11(1):25.
- Yeung J, Tourdot BE, Adili R, et al. 12(S)-HETrE, a 12-Lipoxygenase Oxylipin of Dihomo-γ-Linolenic Acid, Inhibits Thrombosis via Gαs Signaling in Platelets. Arteriosclerosis, thrombosis, and vascular biology. 2016;36(10):2068-2077.
- Nykiforuk CL, Shewmaker C, Harry I, et al. High level accumulation of gamma linolenic acid (C18: 3d6. 9, 12 cis) in transgenic safflower (Carthamus tinctorius) seeds. Transgenic research. 2012;21(2):367-381.
- Tanaka T, Kakutani S, Horikawa C, Kawashima H, Kiso Y. Oral supplementation with dihomo-γ-linolenic acid (DGLA)- enriched oil increases serum DGLA content in healthy adults. Lipids. 2012;47(6):643-646.
- Rao CV. Regulation of COX and LOX by curcumin. Advances in experimental medicine and biology. 2007;595:213-226.
- Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C. Health Implications of High Dietary Omega-6 Polyunsaturated Fatty Acids. Journal of nutrition and metabolism. 2012;2012:539426.
- Tsurutani Y, Inoue K, Sugisawa C, Saito J, Omura M, Nishikawa T. Increased Serum Dihomo-γ-linolenic Acid Levels Are Associated with Obesity, Body Fat Accumulation, and Insulin Resistance in Japanese Patients with Type 2 Diabetes. Intern Med. 2018;57(20):2929-2935.
- Imamura S, Morioka T, Yamazaki Y, et al. Plasma polyunsaturated fatty acid profile and delta-5 desaturase activity are altered in patients with type 2 diabetes. Metabolism. 2014;63(11):1432-1438.
- Ouchi S, Miyazaki T, Shimada K, et al. Decreased circulating dihomo-gamma-linolenic acid levels are associated with total mortality in patients with acute cardiovascular disease and acute decompensated heart failure. Lipids in Health and Disease. 2017;16(1):150.
- Das UN. Arachidonic acid in health and disease with focus on hypertension and diabetes mellitus: A review. Journal of advanced research. 2018;11:43-55.
- Kapoor R, Huang Y-S. Gamma linolenic acid: an antiinflammatory omega-6 fatty acid. Current pharmaceutical biotechnology. 2006;7(6):531-534.
Decreased intake of the essential LA, or inefficient metabolism of the omega-6 fatty acids can lead to decreased production of DGLA. Lack of vitamin or mineral cofactors, or SNPs in the elongase and desaturase enzymes can contribute to lower DGLA levels either from production to DGLA or increased metabolism to AA.
It should also be emphasized that smoking, alcohol, and systemic inflammation can slow the elongase enzyme and conversion to DGLA. Due to the anti-inflammatory and beneficial effects of DGLA, low levels have significant clinical associations such as diabetes, alcoholism, atopic dermatitis, rheumatoid arthritis, cancer, and cardiovascular disease. Decreased levels are associated with increased total mortality in patients with acute cardiac events and decompensated heart failure.
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Supplementation with DGLA or GLA, as well as high dietary intake of the essential LA, can lead to higher DGLA levels.
Lack of vitamin and mineral cofactors, or SNPs in the enzyme which converts DGLA downstream to arachidonic acid, may also contribute to elevations.
Higher DGLA levels are mainly beneficial due to its anti-inflammatory role. Although there is some concern regarding DGLA being converted to its pro-inflammatory metabolite, arachidonic acid, the conversion is generally limited. The reason for this limitation is that inflammatory arachidonic acid-derived lipid mediators (eicosanoids) are made via several pathways two of which are cyclooxygenase (COX) and lipoxygenase (LOX).
The synthesis of AA eicosanoids is dependent on DGLA since DGLA competes with AA for COX and LOX. When DGLA is in excess, it inhibits the synthesis of AA-derived eicosanoids due to its higher affinity for the COX and LOX enzymes.
High levels of DGLA are associated with elevated body mass index, waist circumference, body fat percentage, and other obesity-related parameters. It should be noted that some of these clinical associations are related to increased overall intake of omega-6 fatty acids. But insulin itself can downregulate the enzyme delta-5-desaturase which synthesizes AA from DGLA. Therefore, obesity and insulin resistance can affect delta-5-desaturase resulting in higher DGLA levels.
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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
