Eicosadienoic acid can inhibit the activity of mouse 5'-monophosphoadenosine diphosphate reductase (IMPDH), and its binding to IMPDH is competitive (Ki = 3.1μM) [1]. Eicosadienoic acid is a rare natural n-6 type polyunsaturated fatty acid mainly present in animal tissues. It is metabolized into stearidonic acid (SCA) in macrophages [2]. Eicosadienoic acid is used to study the effects of fatty acid composition on the fluidity and function of cell membranes [3].
In vitro, Eicosadienoic acid (0, 10, 25, 50 and 100μM; 24 hours) increased the proportion of n-6 type polyunsaturated fatty acids (such as LA, GLA, DGLA, AA and adrenal acid) in mouse RAW264.7 macrophages in a dose-dependent manner, and significantly reduced the percentage of monounsaturated fatty acids (MUFA) [4]. Eicosadienoic acid (10μM; 24 hours) inhibited the decrease in cell viability induced by lipopolysaccharide (LPS) in RAW264.7 cells, and downregulated the expression of iNOS and COX-2 in cells and the level of ROS [5].
References:
[1] Mizushina Y, Dairaku I, Yanaka N, et al. Inhibitory action of polyunsaturated fatty acids on IMP dehydrogenase. Biochimie. 2007;89(5):581-590.
[2] Yagaloff KA, et al. Essential fatty acids are antagonists of the leukotriene B4 receptor. Prostaglandins Leukot Essent Fatty Acids. 1995 May;52(5):293-7.
[3] Yang X, Sheng W, Sun G Y, et al. Effects of fatty acid unsaturation numbers on membrane fluidity and α-secretase-dependent amyloid precursor protein processing[J]. Neurochemistry international, 2011, 58(3): 321-329.
[4] Huang YS, Huang WC, Li CW, Chuang LT. Eicosadienoic acid differentially modulates production of pro-inflammatory modulators in murine macrophages. Mol Cell Biochem. 2011;358(1-2):85-94.
[5] Pereira D M, Correia-da-Silva G, Valentão P, et al. Anti-inflammatory effect of unsaturated fatty acids and ergosta-7, 22-dien-3-ol from Marthasterias glacialis: Prevention of CHOP-mediated ER-stress and NF-κB activation[J]. PloS one, 2014, 9(2): e88341.
Eicosadienoic acid能够抑制小鼠5'-单磷酸肌苷脱氢酶（IMPDH）的活性，并且与IMPDH的结合具有竞争性（Ki=3.1μM）[1]。Eicosadienoic acid是一种主要存在于动物组织中的罕见的天然存在的n-6型多不饱和脂肪酸，在巨噬细胞中代谢为stearidonic acid（SCA） [2]。Eicosadienoic acid被用于研究脂肪酸组成对细胞膜流动性和功能的影响[3]。
在体外，Eicosadienoic acid（0, 10, 25, 50和100μM; 24h）以剂量依赖性方式增加了小鼠RAW264.7巨噬细胞中n-6型多不饱和脂肪酸（如LA、GLA、DGLA、AA和肾上腺酸）的比例，并显著降低了单不饱和脂肪酸(MUFA)的百分比 [4]。Eicosadienoic acid（10μM; 24h）抑制了脂多糖（LPS）诱导的RAW264.7细胞活力的降低，并下调了细胞iNOS、COX-2的表达和ROS的水平 [5]。