Gliotoxin

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Formula = C₁₃H₁₄N₂O₄S₂
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CASNo = 67-99-2
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SMILES = O=C1N(C)C2(CO)C(N(C3C(C4)=CC=C [C@@H] 3O)C41SS2)=O
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MolarMass = 326.4 g/mol
Appearance = white to light yellow solid
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Solvent = DMSO
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Section7 = Chembox Hazards
ExternalMSDS = [http://www.fermentek.co.il/MSDS/Gliotoxin-MSDS.htm MSDS] from Fermentek
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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. cite journal|author=Kupfahl C, Ruppert T, Dietz A, Geginat G, Hof H.|year= 2007|title=Candida species fail to produce the immunosuppressive secondary metabolite gliotoxin in vitro|journal=FEMS Yeast Res|volume=7|pages=986–92|pmid=17537180|doi=10.1111/j.1567-1364.2007.00256.x] 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. [http://www.biomol.com/SiteData/docs/productdata/pi129.pdf] It acts by blocking thiol groups in the cell membranes.

References

*"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

[http://www.fermentek.co.il/gliotoxin.htm Gliotoxin] product page from Fermentek