α-Eleostearic Acid

α-Eleostearic acid (α-ESA), also known as 9(Z),11(E),13(E)-octadecatrienoic acid, is a conjugated polyunsaturated fatty acid and peroxisome proliferator-activated receptor γ (PPARγ) agonist that has been found in tung tree seed oil.^1,2 It is converted to 9(Z),11(E)-conjugated linoleic acid (Item Nos. 90140 | 31552) by the cytochrome P450 (CYP) isoform CYP4F13 in rats.³ α-ESA (10 µM) activates PPARγ transcriptional activity in a reporter assay using RAW 264.7 cells.¹ It is an inhibitor of DNA polymerase α, -β, -γ, -Δ, and -ε (IC₅₀s = 10.7, 13.4, 10.6, 14, and 22 µM, respectively) and topoisomerase I and -II (IC₅₀s = 20 and 5 µM, respectively).⁴ α-ESA reduces the viability of, and induces apoptosis in, MCF-7 breast cancer cells in a concentration-dependent manner.⁵ It induces ferroptosis in MDA-MB-231 breast cancer cells, increasing lipid peroxidation when used at concentrations of 50 and 100 µM and inducing cell death when used at concentrations ranging from 10 to 40 µM.² These effects are dependent on long-chain acyl-CoA synthetase 1 (ACSL1) and can be blocked by ferrostatin-1 (Item No. 17729). Dietary administration of α-ESA reduces clinical signs of disease in a model of inflammatory bowel disease (IBD) induced by dextran sodium sulfate (DSS; Item No. 23250) in PPARγ-expressing, but not PPARγ-knockout, mice.¹

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1. Lewis, S.N., Brannan, L., Guri, A.J., et al. Dietary α-eleostearic acid ameliorates experimental inflammatory bowel disease in mice by activating peroxisome proliferator-activated receptor-γ. PLoS One 6(8), e24031 (2011).

2. Beatty, A., Singh, T., Tyurina, Y.Y., et al. Ferroptotic cell death triggered by conjugated linolenic acids is mediated by ACSL1. Nat. Commun. 12(1), 2244 (2021).

3. Wu, Q., and Tsuduki, T. CYP4F13 is the major enzyme for conversion of alpha-eleostearic acid into cis-9, trans-11-conjugated linoleic acid in mouse hepatic microsomes. J. Oleo Sci. 69(9), 1061-1075 (2020).

4. Mizushina, Y., Tsuzuki, T., Eitsuka, T., et al. Inhibitory action of conjugated C₁₈-fatty acids on DNA polymerases and DNA topoisomerases. Lipids 39(10), 977-983 (2004).

5. Moon, H.S., Guo, D.D., Lee, H.G., et al. Alpha-eleostearic acid suppresses proliferation of MCF-7 breast cancer cells via activation of PPARgamma and inhibition of ERK 1 / 2. Cancer Sci. 101(2), 396-402 (2010).

Beatty, A., Singh, T., Tyurina, Y.Y., et al. Ferroptotic cell death triggered by conjugated linolenic acids is mediated by ACSL1. Nat. Commun. 12(1), 2244 (2021).