Gliotoxin
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Gliotoxin".

Gliotoxin
Molecular formula	C13H14N2O4S2
Identifiers
CAS number	67-99-2
SMILES	O=C1N(C)C2(CO)C(N(C3C(C4)=CC=C[C@@H]3O)C41SS2)=O
Properties
Molar mass	326.4 g/mol
Appearance	white to light yellow solid
Solubility in DMSO	soluble
Hazards
MSDS	MSDS from Fermentek
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Previously gliotoxin has also been reported in yeasts of the genus Candida; results of a recent study of 100 clinical Candida isolates, however, have cast doubt on the occurrence of this metabolite in this group of fungi. ¹ It was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite.

Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. It also acts as an inhibitor of farnesyl transferase. It noncompetitively inhibits the chymotrypsin-like activity of the 20S proteasome. In vivo it displays anti-inflammatory activity.² It acts by blocking thiol groups in the cell membranes.

References

1. ^ Kupfahl C, Ruppert T, Dietz A, Geginat G, Hof H. (2007). "Candida species fail to produce the immunosuppressive secondary metabolite gliotoxin in vitro". FEMS Yeast Res 7: 986–92. doi:10.1111/j.1567-1364.2007.00256.x. PMID 17537180. 
2. ^ http://www.biomol.com/SiteData/docs/productdata/pi129.pdf

• Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro: A. Müllbacher, et al.; J. Gen. Microbiol. 131, 1251 (1985)

• "Mechanism of gliotoxin action and factors mediating gliotoxin sensitivity". R.W. Jones & J.G. Hancock; J. Gen. Microbiol. 134: 2067-2075 (1988)

• Gliotoxin stimulates Ca²⁺ release from intact rat liver mitochondria: M. Schweizer & C. Richter; Biochemistry 33, 13401 (1994)

• Extracellular calcium is not required for gliotoxin or dexamethasone- induced DNA fragmentation: a reappraisal of the use of EGTA: P. Waring & A. Sjaarda; Int. J. Immunopharmacol. 17, 403 (1995)

External links

Gliotoxin product page from Fermentek