conjugated linoleic acid

Conjugated linoleic acid, a naturally occurring fatty acid, is present in ruminant meat and dairy products and is produced by a bio-hydrogenation process in the rumen. In this case, the predominant isomer formed is 9cis, 11trans.

9(Z),11(E)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in beef and milk fat.1It binds to peroxisome proliferator-activated receptor α (PPARα; IC50= 140 nM) and activates the receptor in a reporter assay using COS-1 cells expressing mouse PPARα when used at a concentration of 100 μM.29(Z),11(E)-Conjugated linoleic acid inhibits TNF-α-inducedGLUT4expression and increases insulin-stimulated glucose transport in 3T3-L1 adipocytes.3Dietary administration of 9(Z)11(E)-conjugated linoleic acid reduces serum fasting glucose, insulin, and triglyceride levels and decreases white adipose tissue macrophage infiltration inob/obmice. It also increases body weight gain and body fat in weanling mice.4[Matreya, LLC. Catalog No. 1278] 1.Shultz, T.D., Chew, B.P., Seaman, W.R., et al.Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cellsCancer Lett.63(2)125-133(1992) 2.Moya-Camarena, S.Y., Heuvel, J.P.V., Blanchard, S.G., et al.Conjugated linoleic acid is a potent naturally occurring ligand and activator of PPARαJ. Lipid Res.40(8)1426-1433(1999) 3.Moloney, F., Toomey, S., Noone, E., et al.Antidiabetic effects of cis-9, trans-11-conjugated linoleic acid may be mediated via anti-inflammatory effects in white adipose tissueDiabetes56(3)574-582(2007) 4.Pariza, M.W., Park, Y., and Cook, M.E.The biologically active isomers of conjugated linoleic acidProg. Lipid Res.40(4)283-298(2001)

9(E),11(E)-12-nitro Conjugated linoleic acid (9(E),11(E)-12-nitro CLA) is a nitrated fatty acid. It is formed from 9(Z),11(E)-CLA upon exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or a combination of myeloperoxidase, hydrogen peroxide, and nitrite.1It is also formed in LPS-stimulated RAW 264.7 macrophages, an effect that can be reduced by the nitric oxide synthase (NOS) inhibitor L-NAME .29(E),11(E)-12-nitro CLA has been found in human plasma. 1.Woodcock, S.R., Salvatore, S.R., Bonacci, G., et al.Biomimetic nitration of conjugated linoleic acid: Formation and characterization of naturally occurring conjugated nitrodienesJ. Org. Chem.79(1)25-33(2014) 2.Bonacci, G., Baker, P.R.S., Salvatore, S.R., et al.Conjugated linoleic acid is a preferential substrate for fatty acid nitrationJ. Biol. Chem.287(53)44071-44082(2012)

9(E),11(E)-Conjugated Linoleic Acid (9(E),11(E)-CLA) belongs to a group of eight geometric isomers of linoleic acid, characterized by adjacent double bonds. This specific isomer, 9,11 all-trans linoleic acid, was first discovered in ground beef and is found in various dairy products as well. Notably, it has been shown to decrease mammary tumors in rats with dietary inclusion as minimal as 0.1%. [Matreya, LLC. Catalog No. 1181]

9(E),11(E)-9-nitro Conjugated Linoleic Acid (9E,11E-9-nitro CLA) is a nitrated fatty acid produced from 9Z,11E-CLA through exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or the combined action of myeloperoxidase, hydrogen peroxide, and nitrite. Additionally, it forms in LPS-stimulated RAW 264.7 macrophages, a process that can be inhibited by the nitric oxide synthase (NOS) inhibitor L-NAME. This compound has also been detected in human plasma.

9(Z),11(E)-Conjugated Linoleic Acid Methyl Ester, identified in lemon grass (C. flexuosus), serves as a standard for quantifying conjugated linoleic acids in thermally stressed olive oil and trans fats in bakery products. [Matreya, LLC. Catalog No. 1255]

9(E),11(E)-Conjugated Linoleic Acid Methyl Ester, identified in thermally stressed cooking oils, can serve as an indicator for the adulteration of olive oils with lower quality oils. [Matreya, LLC. Catalog No. 1257]

9(Z),11(Z)-Conjugated Linoleic Acid Methyl Ester serves as a standard in the quantification of conjugated linoleic acid methyl esters via GC-MS, according to Matreya, LLC. Catalog No. 1256.

10(E),12(Z)-Conjugated linoleic acid methyl ester serves as a standard for quantifying 10(E),12(Z)-conjugated linoleic acid in L. plantarum culture samples. [Matreya, LLC. Catalog No. 1254]

Bovinic acid ((9Z,11E)-Octadecadienoic acid) is a conjugated linoleic acid with anticancer and anti-atherosclerotic activity and can be used to study coronary heart disease and obesity in the elderly.

Jacaric acid is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants. Structurally, it is an 18-carbon ω-6 triene isomer of γ-linolenic acid . Jacaric acid induces cell cycle arrest and apoptosis in a variety of cancer cell lines (GI50 = 1-5 μM). It increases the production of reactive oxygen species, and cytotoxicity is abolished by the antioxidant α-tocopherol, suggesting that apoptosis results from oxidative stress. Jacaric acid is metabolized in vivo to conjugated linoleic acid , which is also cytotoxic to cancer cells. Jacaric acid inhibits cyclooxygenase-1 in vitro (Ki = 1.7 μM) and, with long term feeding, decreases stearoyl-CoA desaturase expression and activity in mice.

9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes. α-ESA ethyl ester is a neutral, more lipid soluble form of the free acid.

Methyl alpha-eleostearate (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes. α-ESA methyl ester is a neutral, more lipid soluble form of the free acid.

1,2,3-Tritridecanoyl glycerol, a synthetic triacylglycerol featuring tridecanoic acid at the sn-1, sn-2, and sn-3 positions, serves as a standard for relative triacylglycerols quantification in C. elegans fat stores and as an internal standard in quantifying triacylglycerols in serum and liver of adult rat offspring exposed to dietary conjugated linoleic acids during and post-gestation.

trans-Vaccenic acid is a precursor substance that synthesizes saturated fatty acids in the rumen and conjugated linoleic acid at the tissue level. trans-Vaccenic acid inhibits proliferation and induces apoptosis of human nasopharyngeal carcinoma cells through the mitochondria-mediated apoptotic pathway.

CLA, or conjugated linoleic acid, is a polyunsaturated fatty acid that naturally occurs in various animal products such as meat and dairy. It offers several potential health benefits for humans, including the reduction of body fat, improved insulin sensitivity, and anti-inflammatory effects. Extensively researched for its impact on weight loss and muscle growth, CLA also shows potential in preventing chronic diseases like heart disease and cancer. Additionally, it is available as a dietary supplement in capsule form.