Triacsin C

Triacsin C is an inhibitor of long fatty acyl CoA synthetase that has been isolated from Streptomyces aureofaciens.[1] 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.[2]

Triacsin C
Names
IUPAC name
N-(((2E,4E,7E)-undeca-2,4,7-trienylidene)amino)nitrous amide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.127.901
UNII
Properties
C11H17N3O
Molar mass 207.277 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In addition, triacsin C is a vasodilator.[1]

Inhibition of lipid metabolism reduces/removes lipid droplets from HuH7 cells. In hepatitis C infected HuH7 cells, this reduction/removal of lipid droplets significantly reduces virion formation and release.

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.[1] They identified it as a vasodilator.

gollark: ++help
gollark: ```Get out of our way type system! We're going to reinterpret these bits or die trying! Even though this book is all about doing things that are unsafe, I really can't emphasize that you should deeply think about finding Another Way than the operations covered in this section. This is really, truly, the most horribly unsafe thing you can do in Rust. The railguards here are dental floss.```
gollark: _goes off to find rustonomicon_
gollark: https://pastebin.com/S2WeZawLI managed to cause an interesting compile error...
gollark: GAH! Even the inline assembly is too safe!

See also

References
  1. Yoshida K, Okamoto M, Umehara K, Iwami M, Kohsaka M, Aoki H, Imanaka H (1982). "Studies on new vasodilators, WS-1228 A and B. I. Discovery, taxonomy, isolation and characterization". J Antibiot (Tokyo). 35 (2): 151–156. doi:10.7164/antibiotics.35.151. PMID 6804425.CS1 maint: multiple names: authors list (link)
  2. Igal RA, Wang P, Coleman RA (June 1997). "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. 324. ( Pt 2): 529–34. PMC 1218462. PMID 9182714.
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