World Library  
Flag as Inappropriate
Email this Article

Gliotoxin

Article Id: WHEBN0008016328
Reproduction Date:

Title: Gliotoxin  
Author: World Heritage Encyclopedia
Language: English
Subject: Disulfide bond, Organosulfur compounds, Fermentek
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Gliotoxin

Gliotoxin
Identifiers
CAS number  Y
PubChem
ChemSpider  Y
ChEMBL  Y,
Jmol-3D images Image 1
Properties
Molecular formula C13H14N2O4S2
Molar mass 326.4 g/mol
Appearance white to light yellow solid
Density 1.75 g/ml
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 (77 °F), 100 kPa)
 N?)

Gliotoxin is a sulfur-containing mycotoxin produced by several species of fungi, including pathogens of humans such as Aspergillus fumigatus,[1] and also by species of Trichoderma, and Penicillium. Gliotoxin has also been reported from yeasts of the genus Candida,[2] but results from other studies have cast doubt on the production of this metabolite by Candida fungi.[3][4] Gliotoxin 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.[5] It acts by blocking thiol groups in the cell membranes. It was investigated as an antibiotic and antifungal in the 1940s and recently as an antiviral agent.[6][7]

References

  1. ^ Scharf DH, Heinekamp T, Remme N, Hortschansky P, Brakhage AA, Hertweck C. (2012). "Biosynthesis and function of gliotoxin in Aspergillus fumigatus". Appl Microbiol Biotechnol. 93: 467–72. PMID 22094977. doi:10.1007/s00253-011-3689-1. 
  2. ^ Larsen, B,Shah, D, 1991 "Candida isolates of yeast produce a gliotoxin-like substance" Mycopathologia 116:203-208, 1991.
  3. ^ 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 (6): 986–92. PMID 17537180. doi:10.1111/j.1567-1364.2007.00256.x. 
  4. ^ Kosalec I, Puel O, Delaforge M, Kopjar N, Antolovic R, Jelic D, Matica B, Galtier P, Pepeljnjak S. (2010). "Isolation and cytotoxicity of low-molecular-weight metabolites of Candida albicans". Front Biosci 13: 6893–904. PMID 18508703. doi:10.2741/3197. 
  5. ^ http://www.biomol.com/SiteData/docs/productdata/pi129.pdf
  6. ^ Herrick, J. Arthur (March 1945), "Effects of Gliotoxin on Trichophyton Gypseum", The Ohio Journal of Science 
  7. ^ McDougall, J. K. (March 2, 2005), "Antiviral action of gliotoxin", Archives of Virology 
  • 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)

External links

  • Puri, A., Ahmad, A. and Panda, B. P. (2010), Development of an HPTLC-based diagnostic method for invasive aspergillosis. Biomed. Chromatogr., 24: 887–892. doi: 10.1002/bmc.1382 [1]
  • Gliotoxin product page from Fermentek
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 



Copyright © World Library Foundation. All rights reserved. eBooks from World Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.