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Gliotoxin
From Wikipedia, the free encyclopedia
| Gliotoxin | |
|---|---|
(3R,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione | |
| 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] However, a study published in 1991 by Shah and Larsen found "Clinical Isolates of yeast produce a Gliotoxin like substance" in 32 of 50 isolates tested. [2]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.[3] It acts by blocking thiol groups in the cell membranes.
References
- ^ Kupfahl C, Ruppert T, Dietz A, Geginat G, Hof H. (2007). [Expression error: Missing operand for > "Candida species fail to produce the immunosuppressive secondary metabolite gliotoxin in vitro"]. FEMS Yeast Res 7: 986–92. doi:. PMID 17537180.
- ^ Larsen, B,Shah, D, 1991 "Candida isolates of yeast produce a gliotoxin-like substance" Mycopathologia 116:203-208, 1991.
- ^ 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)
- Clinical Isolates of yeast produce a gliotoxin-like substance". D. Shah and B. Larsen; Mycopatholgia 116: 203-208,(1991)
- "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)
