Triacsin C Explained

Triacsin C is an inhibitor of long fatty acyl CoA synthetase that has been isolated from Streptomyces aureofaciens.^{[1] [2] [3]} It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.^[4]

In addition, triacsin C is a vasodilator.

Inhibition of lipid metabolism reduces/removes lipid droplets from HuH7 cells.^[5] In hepatitis C–infected HuH7 cells, this reduction/removal of lipid droplets by triacsin C correlates with a reduction in virion assembly and infectivity.^[6]

General chemical description

Triacsin C belongs to a family of fungal metabolites all having an 11-carbon alkenyl chain with a common N-hydroxytriazene moiety at the terminus. Due to the N-hydroxytriazene group, triacsin C has acidic properties and may be considered a polyunsaturated fatty acid analog.

Triacsin C was discovered by Keizo Yoshida and other Japanese scientists in 1982 in a culture of the microbe Streptomyces aureofaciens. They identified it as a vasodilator.

See also

• Fatty acid degradation#Activation_and_transport_into_mitochondria
• Fatty acyl CoA synthetase

Notes and References

1. J Antibiot (Tokyo) . 1982 . 35 . 2 . 151–156 . Studies on new vasodilators, WS-1228 A and B. I. Discovery, taxonomy, isolation and characterization . Yoshida K, Okamoto M, Umehara K, Iwami M, Kohsaka M, Aoki H, Imanaka H . 10.7164/antibiotics.35.151 . 6804425 . free .
2. Tomoda H, Igarashi K, Omura S. Inhibition of acyl-CoA synthetase by triacsins. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 921. 3. 1987. 595–598. 10.1016/0005-2760(87)90088-9. 3117118.
3. Tomoda H, Igarashi K, Chong JC, Ōmura S. Evidence for an Essential Role of Long Chain Acyl-CoA Synthetase in Animal Cell Proliferation. The Journal of Biological Chemistry. 1991. 266. 7. 4214–4219. 10.1016/S0021-9258(20)64309-5. free. 1999415.
4. Igal RA, Wang P, Coleman RA . Triacsin C blocks de novo synthesis of glycerolipids and cholesterol esters but not recycling of fatty acid into phospholipid: evidence for functionally separate pools of acyl-CoA . Biochem. J. . (Pt 2) . 529–34 . June 1997 . 324 . Pt 2 . 10.1042/bj3240529 . 9182714 . 1218462 .
5. Fujimoto Y, Itabe H, Kinoshita T, Homma KJ, Onoduka J, More M, Yamaguchi S, Makita M, Higashi Y, Yamashita A, Takano T. Journal of Lipid Research. 48. 6. 2007. 1280–1292. 10.1194/jlr.M700050-JLR200. free. 17379924. Involvement of ACSL in local synthesis of neutral lipids in cytoplasmic lipid droplets in human hepatocyte HuH7.
6. Liefhebber JM, Hague CV, Zhang Q, Wakelam MJ, McLauchlan J. Modulation of Triglyceride and Cholesterol Ester Synthesis Impairs Assembly of Infectious Hepatitis C Virus. The Journal of Biological Chemistry. 289. 31. 21276–21288. 2014. 10.1074/jbc.M114.582999. free. 24917668. 4118089.