Gliotoxin

ID 2: 80

Toxin: y

Trivial name:

10H-​3,​10a-​Epidithiopyrazino[1,​2-​a]​indole-​1,​4-​dione, 2,​3,​5a,​6-​tetrahydro-​6-​hydroxy-​3-​(hydroxymethyl)​-​2-​methyl-​, [3R-​(3α,​5aβ,​6β,​10aα)​]​- (8CI); Gliotoxin (6CI,​7CI); Aspergillin; S. N. 12870

Systematic name:

10H-3,10a-Epidithiopyrazino[1,2-a]indole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-, (3R,5aS,6S,10aR)-

Molecular formulae: 

C₁₃H₁₄N₂O₄S₂

Molecular weight: 326.39

Chemical abstract number: 67-99-2

Literature reference:

• Synthesis of aromatic amino acids in the living cell. Hugounenq, L.; Florence, Gabriel. Bulletin de la Societe de Chimie Biologique (1920), 2, 133-6.
  The nature of the antibiotic substances produced by Aspergillus fumigatus. Waksman, Selman A.; Geiger, Walton B. Journal of Bacteriology (1944), 47, 391-7.
  A preliminary note on the antibacterial substance from Aspergillus flavus. DEY N C. Current science (1945), 14, 265-7.
  Gliotoxin from Aspergillus chevalieri. Wilkinson, S.; Spilsbury, J. F. Nature (London, United Kingdom) (1965), 206(4984), 619.
  Determination of optimum growth conditions for gliotoxin production by Aspergillus fumigatus and development of a novel method for gliotoxin detection. Belkacemi, L.; Barton, R. C.; Hopwood, V.; Evans, E. G. V. (CORPORATE SOURCE PHLS Mycology Reference Laboratory, Department of Microbiology, University of Leeds, Leeds, UK). SOURCE Med. Mycol., 37(4), 227-233 (English) 1999 Blackwell Science Ltd.
  Aspergillin PZ, a novel isoindole-​alkaloid from Aspergillus awamori. Zhang Yi; Wang Tao; Pei Yuehu; Hua Huiming; Feng Baomin. The Journal of antibiotics (2002), 55(8), 693-5.
  Frequency and species distribution of gliotoxin-producing Aspergillus isolates recovered from patients at a tertiary-care cancer center. Lewis RE, Wiederhold NP, Lionakis MS, Prince RA, Kontoyiannis DP.J Clin Microbiol. 2005 Dec;43(12):6120-2.
  Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati. Larsen TO, Smedsgaard J, Nielsen KF, Hansen MA, Samson RA, Frisvad JC. Med Mycol. 2007 May;45(3):225-32.
  Metabolites of Aspergillus sp. HT-​2. Zhang, Limin; Li, Zhanlin; Bai, Jiao; Wu, Xin; Wang, Yu; Hua, Huiming. Zhongguo Yaoxue Zazhi (Beijing, China) (2011), 46(15), 1154-1158.
  Antitumor metabolites from fungus Aspergillus sydowi D 2-​6. Ren, Hong; Cao, Xueli; Wang, Qiaoe; Xu, Chunming. Zhongguo Yaoxue Zazhi (Beijing, China) (2011), 46(8), 569-575.
  

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/6223
• http://jb.asm.org/content/47/4/391.full.pdf+html
• http://www.currentscience.ac.in/Downloads/article_id_014_10_0265_0267_0.pdf
• http://www.nature.com/nature/journal/v206/n4984/pdf/206619a0.pdf
• https://www.jstage.jst.go.jp/article/antibiotics1968/55/8/55_8_693/_article
• http://www.tandfonline.com/doi/abs/10.1080/13693780601185939
• http://mmy.oxfordjournals.org/content/37/4/227.abstract

Aspergillus Species known to produce this metabolite:

• /species/a-niger
• /species/a-fumigatus
• /species/a-flavus
• /species/a-chevalieri
• /species/a-awamori
• /species/neosartorya-pseudofischeri
• /species/aspergillus-sp-ht-2
• /species/a-sydowii

Toxicity:

Gliotoxin posseses a spectrum of biological activities including antibacterial and antiviral activities, and it is also a potent immunomodulating agent. Gliotoxin is also an inducer of apoptotic cell death in a number of cell types, and it has been found to be associated with some diseases attributed directly or indirectly to fungal infections. It is a secondary metabolite produced by a number of Aspergillus and Penicillium species.
It is a potent immunosuppressive metabolite and brings about apoptosis in cells. Because of its effects on the immune system it may have a place in transplant surgery. There is limited evidence for its occurrence in moulded cereals. A. fumigatus is a potent pathogen which can colonise the lungs and other body tissues after ingestion of spores. There is some limited evidence that gliotoxin may be formed in situ in such circumstances.
hamster LDLo oral 25mg/kg (25mg/kg) Veterinary and Human Toxicology. Vol. 32(Suppl), Pg. 63, 1990.
Link to PubMed

mouse LD50 intraperitoneal 32mg/kg (32mg/kg) Chemotherapia. Vol. 10, Pg. 12, 1965.

mouse LD50 intravenous 7800ug/kg (7.8mg/kg) Chemotherapia. Vol. 10, Pg. 12, 1965.

mouse LD50 oral 67mg/kg (67mg/kg) Chemotherapia. Vol. 10, Pg. 12, 1965.


mouse LD50 subcutaneous 25mg/kg (25mg/kg) Chemotherapia. Vol. 10, Pg. 12, 1965.


rabbit LDLo intravenous 45mg/kg (45mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION. GASTROINTESTINAL: “HYPERMOTILITY, DIARRHEA” Journal of the American Chemical Society. Vol. 65, Pg. 2005, 1943.


rat LDLo intravenous 45mg/kg (45mg/kg) Veterinary and Human Toxicology. Vol. 32(Suppl), Pg. 63, 1990.
Link to PubMed

rat LDLo unreported 50mg/kg (50mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Journal of the American Chemical Society. Vol. 65, Pg. 2005, 1943.

Date uploaded: 2007-09-25 13:12:16

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Mycotoxin & Metabolites

Mycotoxin & Metabolite database

Aspergillus species produce a large number of secondary metabolites, sometimes referred to as extrolites. We attempt to list them all here and we also collect published papers.

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