Fatty acids. Part 13. The synthesis of all the cis n-octadecenoic acids

Gunstone, Frank D.; Ismail, Ishamri

doi:10.1016/0009-3084(67)90029-1

Cited by 87 publications

(15 citation statements)

References 49 publications

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“…Methyl esters of the cis-octadecenoates were synthesized as described previously (3). ATP, coenzyme A and Triton X-100 (polyoxyethylene alcohol lauryl ether) were from Sigma Chemical.…”

Section: Methodsmentioning

confidence: 99%

Activation of long chain fatty acids by subcellular fractions of rat liver: III. Effect of ethylenic bond position on acyl‐CoA formation ofcis‐octadecenoates

Lippel

Carpenter

Gunstone

et al. 1973

Lipids

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The rates of rat liver microsomal and mitochondrial activation of the Δ4 to Δ17cis‐octadecenoate positional isomers have been investigated. The fatty acid to protein ratios required for maximum activation of the Δ8, Δ9 and Δ10 isomers were much lower than the corresponding ratios required for maximum activation of thecis‐octadecenoates with double bonds at either end of the fatty acid molecule. Also, as the incubation temperature was raised from 22–38 C the Δ8 and Δ9 isomers exhibited little change in their rates of activation, while large increases in activation rates of the isomers with the double bond at either end of the fatty acid chain were observed. Differential inhibition of the activation of the various positional isomers was observed when anionic, cationic, or nonionic detergents were included in the incubation medium. The different responses to fatty acid concentration, temperature and detergents are attributed to enzyme specificity and to differences in solution properties of thecis‐octadecenoates, rather than to the presence of separate rat liver enzymes that catalyze acyl‐CoA ester formation of the various positional isomers.

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“…Methyl esters of the cis-octadecenoates were synthesized as described previously (3). ATP, coenzyme A and Triton X-100 (polyoxyethylene alcohol lauryl ether) were from Sigma Chemical.…”

Section: Methodsmentioning

confidence: 99%

Activation of long chain fatty acids by subcellular fractions of rat liver: III. Effect of ethylenic bond position on acyl‐CoA formation ofcis‐octadecenoates

Lippel

Carpenter

Gunstone

et al. 1973

Lipids

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“…These early rat studies and later investigations (156) indicated that absorption of hydrogenated fat is equivalent to absorption of non hydrogen ated fats and oils. Chemically synthesized individual fatty acid isomers and their triglycerides have melting points that vary from -\3-54°C (14, 34, 66,72,73,168,169); recent animal studies with hydrogenated fats suggest that all isomers, including those with melting points higher than body temperature, are absorbed as well as oleic acid (57,120,121,225). These animal studies have been confirmed by human studies with pure triglycerides containing deuterated cis and trans positional octadecenoic acid isomers (5 6, 58, 59); melting point, double bond position, and configuration have no measurable effect on the absorption of any isomer.…”

Section: Absorptionmentioning

confidence: 98%

Nutrition and Biochemistry of Trans and Positional Fatty Acid Isomers in Hydrogenated Oils

Ea¹

1984

Annu. Rev. Nutr.

176

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“…The c-ix-octadecenoate isomers were synthesized in methyl ester form as described previously 6 14). The isomers were quantitated for these studies by GLC using methyl pentadecanoate as an internal standard.…”

Section: Farty Acidsmentioning

confidence: 99%

Quantitative effects of unsaturated fatty acids in microbial mutants. VI. Selective growth responses of yeast and bacteria to cis-octadecenoate isomers

Ohlrogge¹,

Barber²,

Lands³

et al. 1976

Can. J. Biochem.

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The full series of positional isomers of cis-octadecenoate were tested for their suitability in meeting the nutritional requirement for unsaturated fatty acids by mutants of Escherichia coli and Saccharomyces cerevisiae that were unable to synthesize unsaturated fatty acids. Quantitative comparisons of the efficiencies of the various isomers showed a range from 0-48 cells per femtomole for the prokaryotic cells and 0-5 for eukaryotic cells. The delta 5 isomer was much more effective than the delta 6 isomer with the bacterial cells whereas the reverse was true with the yeast cells. In general, isomers containing a cis ethylenic bond between carbons 7 and 12 were able to support extensive growth of either type of mutant. Since all of the various isomers were incorporated into cellular lipids by both types of microorganism, the different efficiencies observed in supporting growth were not a simple reflection of the inability of an acid to be esterified. The differences may reflect the suitability of the resultant esterified product to function as a normal membrane lipid. The contents of various fatty acids in the cellular phospholipids when growth ceases may have a linearly cumulative relationship to the degree of expansion of the acyl chains.

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Fatty acids. Part 13. The synthesis of all the cis n-octadecenoic acids

Cited by 87 publications

References 49 publications

Activation of long chain fatty acids by subcellular fractions of rat liver: III. Effect of ethylenic bond position on acyl‐CoA formation ofcis‐octadecenoates

Activation of long chain fatty acids by subcellular fractions of rat liver: III. Effect of ethylenic bond position on acyl‐CoA formation ofcis‐octadecenoates

Nutrition and Biochemistry of Trans and Positional Fatty Acid Isomers in Hydrogenated Oils

Quantitative effects of unsaturated fatty acids in microbial mutants. VI. Selective growth responses of yeast and bacteria to cis-octadecenoate isomers

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