LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

alpha-eleostearic acid

Systematic Name

9Z,11E,13E-octadecatrienoic acid

Synonyms

cis-9, trans-11, trans-13-octadecatrienoic acid
C18:3n-5,7,9
alpha-eleostearinic acid
Margarolic acid
cis-Eleostearic acid

LM ID

LMFA01030147

Formula

C₁₈H₃₀O₂

Exact Mass

Calculate m/z

278.22458

Sum Composition

FA 18:3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

9(Z),11(E),13(E)-Octadecatrienoic Acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil.¹ α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats.² It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ.¹ In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 µM.² It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 µM for different isoforms of the enzymes.³

This information has been provided by Cayman Chemical

References

1. Yasui, Y., Hosokawa, M., Sahara, T., et al. Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARγ in human colon cancer caco-2 cells. Prostaglandins Leukot. Essent. Fatty Acids 73(2), 113-119 (2005).

2. Tsuzuki, T., Tokuyama, Y., Igarashi, M., et al. Tumor growth suppression by a α-eleostearic acid, linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis 25(8), 1417-1425 (2004).

3. 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).