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Structure Database (LMSD)

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Common Name

beta-eleostearic acid

Systematic Name

9E,11E,13E-octadecatrienoic acid

Synonyms

trans-9, trans-11, trans-13-octadecatrienoic acid
C18:3n-5,7,9
beta-eleostearinic acid

LM ID

LMFA01030148

Formula

C₁₈H₃₀O₂

Exact Mass

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278.22458

Sum Composition

FA 18:3

Status

Curated

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Classification

Biological Context

9(E),11(E),13(E)-Octadecatrienoic acid (β-ESA) is a conjugated polyunsaturated fatty acid that is found in plant seed oils and in mixtures of conjugated linolenic acids synthesized by the alkaline isomerization of linolenic acid.¹ It reduces growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. In vitro, β-ESA induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA. β-ESA decreases protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells via production of reactive oxygen species.² It also inhibits bacterial fatty acid dioxygenase with a Ki value of 49 nM in vitro.³

This information has been provided by Cayman Chemical

References

1. Yasui, Y., Hosokawa, M., Kohno, H., et al. Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells. Anticancer Res. 26(3A), 1855-1860 (2006).

2. Sun, Z., Wang, H., Ye, S., et al. Beta-eleostearic acid induce apoptosis in T24 human bladder cancer cells through reactive oxygen species (ROS)-mediated pathway. Prostaglandins Other Lipid Mediat. 99(1-2), 1-8 (2012).

3. Mashhadi, Z., Boeglin, W.E., and Brash, A.R. Robust inhibitory effects of conjugated linolenic acids on a cyclooxygenase-related linoleate 10S-dioxygenase: Comparison with COX-1 and COX-2. Biochim. Biophys. Acta 1851(10), 1346-1352 (2015).