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Α-Eleostearic acid

Α-Eleostearic acid

α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid (the all-trans or (9E,11E,13E) isomer). Its high degree of unsaturation gives tung oil its properties as a drying oil.

Biochemical properties

α-Eleostearic acid makes up about 60% of the fatty acids from bitter gourd oil.

In their pioneering work on essential fatty acids, George Burr, Mildred Burr and Elmer Miller compared the nutritional properties of α-eleostearic acid (ESA) to that of its isomer alpha-linolenic acid (ALA). ALA relieved essential fatty acid deficiency; ESA did not.

In rats, α-eleostearic acid is converted to a conjugated linoleic acid.{{cite journal |doi-access=free}} The compound has been found to induce programmed cell death of fat cells,{{cite journal and of HL60 leukemia cells in vitro at a concentration of 20 μM. Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon carcinogenesis in rats.

Sources

α-Eleostearic acid is found in the oils extracted from seeds. Tung oil has 82% α-eleostearic acid. Bitter gourd seed oil has 60% α-eleostearic acid.

Etymology

Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.

References

References

  1. Burr, G.O.. (1932). "On the nature and role of the fatty acids essential in nutrition". J. Biol. Chem..
  2. (2008). "α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd". Journal of Agricultural and Food Chemistry.
  3. (2004). "Dietary seed oil rich in conjugated linolenic acid from bitter melon inhibits azoxymethane-induced rat colon carcinogenesis through elevation of colonic PPAR γ expression and alteration of lipid composition.". International Journal of Cancer.
  4. (2006-10-30). "Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology". Elsevier.
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fatty-acids alkenoic-acids polyenes
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