Separation of saturated, unsaturated, and acetylenic fatty acid isomers by silver resin chromatography

1978 ◽  
Vol 55 (7) ◽  
pp. 561-563 ◽  
Author(s):  
E. A. Emken ◽  
J. C. Hartman ◽  
C. R. Turner
Keyword(s):  
Fatty Acid ◽  
Acetylenic Fatty Acid

scholarly journals First total synthesis of the (±)-2-methoxy-6-heptadecynoic acid and related 2-methoxylated analogs as effective inhibitors of the Leishmania topoisomerase IB enzyme

2012 ◽  
Vol 84 (9) ◽  
pp. 1867-1875 ◽  
Author(s):  
Néstor M. Carballeira ◽  
Michelle Cartagena ◽  
Fengyu Li ◽  
Zhongfang Chen ◽  
Christopher F. Prada ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Total Synthesis ◽  
Leishmania Donovani ◽  
Dna Topoisomerase ◽  
Triple Bonds ◽  
Weak Intermolecular Interactions ◽  
Topoisomerase Ib ◽  
Effective Inhibition ◽  
Acetylenic Fatty Acid

The fatty acids (±)-2-methoxy-6Z-heptadecenoic acid, (±)-2-methoxy-6-hepta-decynoic acid, and (±)-2-methoxyheptadecanoic acid were synthesized and their inhibitory activity against the Leishmania DNA topoisomerase IB enzyme (LdTopIB) determined. Both 2-OMe-17:1 fatty acids were synthesized from 4-bromo-1-pentanol, the olefinic fatty acid in 10 steps and in 7 % overall yield, while the acetylenic fatty acid in 7 steps and in 14 % overall yield. The 2-OMe-17:0 acid was prepared in 6 steps and in 42 % yield from 1-hexa-decanol. The 2-OMe-17:1 acids inhibited LdTopIB, with the acetylenic acid displaying an EC50 = 16.6 ± 1.1 μM, but the 2-OMe-17:0 acid did not inhibit LdTopIB. The (±)-2-methoxy-6Z-heptadecenoic acid preferentially inhibited LdTopIB over the human TopIB enzyme. Unsaturation seems to be a prerequisite for effective inhibition, rationalized in terms of weak intermolecular interactions between the active site of LdTopIB and either the double or triple bonds of the fatty acids. Toxicity toward Leishmania donovani promastigotes was also investigated, resulting in the order acetylenic > olefinic > saturated with the (±)-2-methoxy-6-heptadecynoic acid displaying an EC50 = 74.0 ± 17.1 μM. Our results indicate that α-methoxylation decreases the toxicity of C17:1 fatty acids toward L. donovani promastigotes, but improves their selectivity index.

Santalum insulare Acetylenic Fatty Acid Seed Oils: Comparison within the Santalum Genus

2008 ◽  
Vol 85 (4) ◽  
pp. 353-356 ◽  
Author(s):  
J.-F. Butaud ◽  
P. Raharivelomanana ◽  
J.-P. Bianchini ◽  
E. M. Gaydou
Keyword(s):  
Fatty Acid ◽  
Seed Oils ◽  
Acetylenic Fatty Acid

Mass spectra of acetylenic fatty acid methyl esters and derivatives

Lipids ◽  
1976 ◽  
Vol 11 (8) ◽  
pp. 599-603 ◽  
Author(s):  
R. Kleiman ◽  
M. B. Bohannon ◽  
F. D. Gunstone ◽  
J. A. Barve
Keyword(s):  
Fatty Acid ◽  
Mass Spectra ◽  
Fatty Acid Methyl Esters ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Acetylenic Fatty Acid

ChemInform Abstract: Taurospongins B and C, New Acetylenic Fatty Acid Derivatives Possessing a Taurine Amide Residue from a Marine Sponge of the Family Spongiidae.

ChemInform ◽  
2014 ◽  
Vol 45 (42) ◽  
pp. no-no
Author(s):  
Takaaki Kubota ◽  
Haruna Suzuki ◽  
Azusa Takahashi-Nakaguchi ◽  
Jane Fromont ◽  
Tohru Gonoi ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Marine Sponge ◽  
Fatty Acid Derivatives ◽  
The Family ◽  
Acetylenic Fatty Acid
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