Eicosapentaenoic Acid - CAS 10417-94-4
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Not Intended for Therapeutic Use. For research use only.
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Eicosapentaenoic acid (EPA) is an omega-3 fatty acid.
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1.Synthesis of the Conjugated Trienes 5E,7E,9E,14Z,17Z Eicosapentaenoic Acid and 5Z,7E,9E,14Z,17Z Eicosapentaenoic Acid, and Their Induction of Apoptosis in DLD-1 Colorectal Adenocarcinoma Cells
Tsuyoshi Tsuzuki, Kazumi Tanaka, Shigefumi Kuwahara, and Teruo Miyazawa,* Lipids, Vol. 40, no. 2 (2005)
To identify the specific cytotoxic FA, we have synthesized possible candidates for the active species. Here, we report the synthesis of (5E,7E,9E,14Z,17Z)-5,7,9,14,17-eicosapentaenoic acid (E-CEPA, Scheme 1) and its 5-(Z) isomer (Z-CEPA, Scheme. 1), which both exist naturally in the red alga (Ptilota filicina J. Agardh). We then examined the cytotoxicity of these molecules in human tumor cells and confirmed that both isomers have strong bioactivity.
2.Accumulation of Eicosapentaenoic Acid in Membranes of Erythrocytes and Leukocytes during Alterative-Exudative and Allergic Inflammation
N. M. Shilina, O. N. Komarova, F. A. Medvedev, M. I. Dubrovskaya*, and I. Ya. Kon’. Bulletin of Experimental Biology and Medicine, Vol. 149, No. 5, 2010
The composition of fatty acids in erythrocyte membranes from healthy children was characterized by prevalence of w6-family arachidonic acid (AA) and high content of 蠅3-family docosahexaenoic acid (DHA; relative to the amount of polyunsaturated fatty acids). The contents of AA (20:4) and DHA (22:6) decreased sharply, while the amount of eicosapentaenoic acid (EPA; 20:5) of the w3 family increased significantly in IDGIT patients (Table 1; Fig. 1, a). These changes were observed in IDGIT patients with normal body weight and obesity (Table 1; Fig. 1, a). Therefore, severe metabolic changes during obesity do not affect the composition of cell membrane fatty acids under conditions of inflammation. Changes in the amount of fatty acids in erythrocyte membranes were followed by variations in some indexes for the state of membranes. The EPA/DHA ratio in membranes was significantly elevated during inflammation (12.8 vs. 3.2 in healthy donors).
3.Seasonal Transfer of the Pool of the Essential Eicosapentaenoic Acid along the Pelagic Trophic Chain of a Eutrophic Reservoir
N. N. Sushchik, M. I. Gladyshev, O. N. Makhutova. Doklady Biological Sciences, 2008, Vol. 422, pp. 355–356.
It is known that not only the amount of produced and consumed organic matter, but also its quality, i.e., its elementary and biochemical composition are important for functioning of trophic chains. In the past two decades, it has been demonstrated that interaction between producers and primary consumers (phyto- and zooplankton) in pelagic ecosystems substantially depends on the phytoplankton content of the essential eicosapentaenoic acid (20:5 w3, EPA). It is believed that the EPA content of seston, which ultimately determines the efficiency of interaction between trophic links, inversely depends on the trophicity level of water ecosystems. This statement is based on the analysis of summer phytoplankton, which is known to be mainly represented by diatom, cryptophyte, and other EPArich microalgae in oligotrophic water bodies, whereas cyanobacteria incapable of synthesizing this fatty acid dominate eutrophic water bodies.
4.Eicosapentaenoic acid increases lipolysis through up-regulation of the lipolytic gene expression and down-regulation of the adipogenic gene expression in 3T3-L1 adipocytes
Mak-Soon Lee, In-Sook Kwun, Yangha Kim. Genes Nutr (2008) 2:327–330
In the present study, we investigated the effects of eicosapentaenoic acid (EPA), known as one of the most critical components of n-3 PUFA, on lipid metabolism and the underlying mechanisms in 3T3-L1 adipocytes. We hypothesize that EPA stimulates lipolysis through induction of lipolytic gene expression and suppression of adipogenic gene expression. We measured the lipid accumulation and release of free fatty acids (FFAs) and glycerol into medium followed by EPA treatment. In addition, the mRNA levels of the adipogenic genes including peroxisome proliferator-activated receptor-c (PPAR-c) and acetyl-CoA carboxylase (ACC), and carnitine palmitoyltransferase I-a (CPT-Ia), one of lipolytic genes, were measured.
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CAS 10417-94-4 Eicosapentaenoic Acid

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