Cyberlipid

 

 

SULFUR CONTAINING FATTY ACIDS

 

Thia fatty acids : sulfur-substituted fatty acid analogues are actively synthesized as they are reported to have important pharmacological properties (antiatherosclerosis and antioxidant).
They can have a variable number of carbon atoms and the sulfur atom in different position (3-thia or 4-thia).


The most commonly 3-thia fatty acids studied are presently:

dodeca thia acetic acid CH3-(CH2)11-S-CH2-COOH
tetradeca thia acetic acid CH3-(CH2)13-S-CH2-COOH

These fatty acid derivatives are reported to have triglyceride and cholesterol lowering effects in animal models (Skrede S et al., Biochim Biophys Acta 1997, 1344, 115).

 

Isomeric epithio stearic acids have been described as minor constituents in canola oil. They were tentatively identified were the 9,12; 8,11; and 7,10 epithio stearic acids (Wijesundera RC et al., JAOCS 1988, 65, 959). The general formula is given below.

 


x = 5, 6 or 7 and y = 7, 6 or 5, respectively

 

– Sulfated fatty acids : New fatty acid derivatives have been isolated from the regurgitant of the grasshopper species Schistocerca americana. These compounds (named caeliferins) are composed of saturated and monounsaturated sulfated a-hydroxy fatty acids in which the w-carbon is substituted with a sulfated hydroxyl group (Alborn HT et al., PNAS 2007, 104, 12976). These compounds have a carbon chain of 15–20 carbons and are distributes in varying proportions. Of these, the 16:1 analog is predominant and is also the most active in inducing release of volatile terpenoid compounds when applied to damaged leaves of corn seedlings.

 

caeliferin
Caeliferin A 16:1

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