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Α-Linolenic Acid

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Α-Linolenic Acid 2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected] Product Information α-Linolenic acid Identification Product Number ALN-CG-xxx CAS Number 463-40-1 EN Number 207-334-8 Common Name α-Linolenic acid Systematic Name (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid Alternative Names 18:3 (n-3); Linolenic acid; α-LA; ALA Storage Temperature -80°C or lower Characteristics Specifications Molecular Formula C18H30O2 Purity ≥ 99 % Molecular Weight 278.44 g/mol Form Liquid above -11°C Melting Point -11 to -12°C Color Clear, colorless Density 0.914 g/mL at 25°C (lit.) Precautions & Disclaimer For laboratory use only. Not for use on humans. Not for drug, household or other uses. Handling & Preparation Instructions This purified fatty acid is liquid at room temperature (oil) and not soluble in water. The product is supplied sterile. It can be solubilized in undiluted serum or in ethanol or DMSO. Essential fatty acids are also soluble in chloroform or ether. However those two organic solvents are not recommended with the use of cells. After reconstitution, the product can be aliquoted and stored at -80°C. We recommend adding the essential fatty acids cocktail to the medium the day of use. The concentration to add to the culture is to be determined by the user. As a starting point, we provide some references from the literature. Amri et al. used α-Linolenic acid to induce adipocyte differentiation and/or to activate PPARs in cultured cells [1]. They showed that a concentration of 200 μM stimulated transcription of the FA transporter FAAR (NUC I) in transfected 3T3-C2 cells. Additionally, they demonstrated that a concentration of 250 μM promoted the differentiation of Ob1771 preadipocytes. Storage Polyunsaturated fatty acids are sensitive to oxidation, light and heat. The vacuum amber glass ampoule is optimal to prevent premature degradation. The product must be stored under -80°C and freeze-thaw cycles should be avoided. The product is stable in its ampoule at -80°C for at least 12 months. About essential fatty acids and derivatives Omega (ω) -3 and ω -6 fatty acids are essential to maintain the homoeostasis of the human body. Linoleic and α-Linolenic acids are considered the only two essential fatty acids because they cannot be synthetized by animals. Therefore, they have to be accumulated from food because mammals lack the appropriate enzyme to perform the carbon desaturation beyond carbons 9 and 10 to introduce a double bond. However, humans can synthesize long-chain (20 carbons or more) ω-6 fatty acids from the parent fatty acid Linoleic acid and long-chain ω-3 fatty acids from the parent fatty acid α-Linolenic acid. © 2017, SiliCycle Inc. Printed in Canada 2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA Tel.: +1 418 874.0054 / Fax: +1 418 874.0355 Toll Free: +1 877 745.4292 (North America Only) Email: [email protected] Fatty acids are the constituent of the hydrophobic tail of phospholipids that form the cell membrane. When polyunsaturated fatty acids (PUFAs) are used to form phospholipids, the curvature in their structure creates spacing between them, allowing the increase of lateral movements of transmembrane proteins. Movement of membrane proteins, such as receptors, integrins and ion channels, is fundamental to their function. PUFAs are also essential precursors of the eicosanoid family of hormones. Supplementation with ω-3 fatty acids has been shown to reduce inflammation and increase microglial phagocytosis in a model of multiple sclerosis [2]; to suppress the pathological phenotype of human bronchial epithelial cells in a model of cystic fibrosis [3]; and to protect photoreceptors from oxidation-induced apoptosis in rats retinal neuron cells [4]. These in vitro studies demonstrate that various cell types do benefit from supplementation with essential fatty acids, not only adipocytes. The beneficial effects of essential fatty acid supplementation have been well documented in vivo as well. For example, clinical studies have demonstrated that a diet rich in ω-3 fatty acids can reduce inflammation in obese pregnant women [5] and reduce the progression of Alzheimer’s disease [6]. About α-Linolenic acid α-Linolenic acid is a naturally occurring ω-3 fatty acid found in plant oils such as flaxseeds, canola, soy, and walnuts. α- Linolenic acid is an important precursor for the synthesis of longer chain ω-3 PUFAs [7]. Of particular interest, Eicosapentaenoic acid (EPA) and Docosahexaenoic acid (DHA) are ω-3 fatty acids present in fish oil that can also be synthesized in humans from dietary α-Linolenic acid intake. However, the efficacy of this desaturation is low. Indeed, less than 20 % of α-Linolenic acid will be converted to downstream derivatives [8-14]. The efficacy of ω−3 long-chain PUFA synthesis decreases down the cascade of α-Linolenic acid conversion. Hence, the conversion to DHA from α-Linolenic acid is less efficient than for EPA [7, 15]. Bone marrow mesenchymal stromal cells (BMSCs) are used in cell therapy due to their immunomodulatory capability. However, when extensively cultured in vitro, their cell membranes become deficient in ω-3 fatty acids, limiting their anti- inflammatory properties. Cultured-BMSCs were supplemented with different PUFAs. Supplementation with EPA and DHA efficiently attenuated inflammatory signaling while supplementation with α-Linolenic acid did not [16], probably due to the low capability of BMSCs to perform the desaturation steps necessary to convert α-Linolenic acid to EPA and DHA [17]. The role of the α-Linolenic ω-3 fatty acid in cancer, insulin resistance and cardiovascular disease has been studied extensively and reviewed by Brenna et al. [8]. Contact Us Thank you for choosing a SiliCycle product. Customer service is our priority and we give our best to answer your needs. If you have any questions or need further information, please contact us at [email protected] and our team of cell biologists will be delighted to respond quickly. References [1] Amri EZ, et al. (1995) Cloning of a protein that mediates transcriptional effects of fatty acids in preadipocytes. Homology to peroxisome proliferator-activated receptors J Biol Chem [2] Chen S, et al. (2014) n-3 PUFA supplementation benefits microglial responses to myelin pathology Sci Rep [3] Njoroge SW, et al. (2012) DHA and EPA reverse cystic fibrosis-related FA abnormalities by suppressing FA desaturase expression and activity J Lipid Res [4] Simon MV, et al. (2016) Synthesis of docosahexaenoic acid from Eicosapentaenoic acid in retina neurons protects photoreceptors from oxidative stress J Neurochem [5] Haghiac M, et al. (2015) Dietary Omega-3 Fatty Acid Supplementation Reduces Inflammation in Obese Pregnant Women: A Randomized Double-Blind Controlled Clinical Trial PLoS One [6] Wang X, et al. (2015) Effects of n-3 FA supplementation on the release of proresolving lipid mediators by blood mononuclear cells: the OmegAD study J Lipid Res [7] Burdge GC, et al. (2005) Conversion of alpha-Linolenic acid to longer-chain polyunsaturated fatty acids in human adults Reprod Nutr Dev [8] Brenna JT, et al. (2009) alpha-Linolenic acid supplementation and conversion to n-3 long-chain polyunsaturated fatty acids in humans Prostaglandins Leukot Essent Fatty Acids [9] Brenna JT (2002) Efficiency of conversion of alpha-Linolenic acid to long chain n-3 fatty acids in man Curr Opin Clin Nutr Metab Care [10] Wijendran V, et al. (2004) Dietary n-6 and n-3 fatty acid balance and cardiovascular health Annu Rev Nutr [11] Burdge GC, et al. (2002) Conversion of alpha-Linolenic acid to eicosapentaenoic, Docosapentaenoic and docosahexaenoic acids in young women Br J Nutr [12] Burdge GC, et al. (2002) Eicosapentaenoic and Docosapentaenoic acids are the principal products of alpha-Linolenic acid metabolism in young men* Br J Nutr [13] Giltay EJ, et al. (2004) Docosahexaenoic acid concentrations are higher in women than in men because of estrogenic effects Am J Clin Nutr [14] Burdge G (2004) Alpha-Linolenic acid metabolism in men and women: nutritional and biological implications Curr Opin Clin Nutr Metab Care [15] Innis SM (2007) Fatty acids and early human development Early Hum Dev [16] Tigistu-Sahle F, et al. (2016) Metabolism and phospholipid assembly of polyunsaturated fatty acids in human bone marrow mesenchymal stromal cells J Lipid Res [17] Grammatikos SI, et al. (1994) Diversity in the ability of cultured cells to elongate and desaturate essential (n-6 and n-3) fatty acids Ann N Y Acad Sci © 2017, SiliCycle Inc. Printed in Canada .
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