Date: 26 November 2013
Secondary metabolites, 3D structure: Trivial name – gliotoxin
Copyright: n/a
Notes:
Species: A. flavus, A. fumigatus, A. niger, A. terreus, Eurotium chevalieri, Neosartorya pseudofischeriSystematic 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: C13H14N2O4S2Molecular weight: 326.393Chemical abstracts number: 67-99-2Selected references: Larsen TO, Smedsgaard J, Nielsen KF, Hansen MA, Samson RA, Frisvad JC. Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati. Med Mycol. 2007 May;45(3):225-32. 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. Lewis RE, Wiederhold NP, Lionakis MS, Prince RA, Kontoyiannis DP.J Clin Microbiol. 2005 Dec;43(12):6120-2. Frequency and species distribution of gliotoxin-producing Aspergillus isolates recovered from patients at a tertiary-care cancer center.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. 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. 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.
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Aspergillus flavus and Aspergillus parasiticus can produce aflatoxins are generally known as storage fungi, but they can also cause ear rots in the field. These species are observed as a gray-green, powdery molds and they can be detected in corn because they produce compounds that are fluorescent under black light.
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Histopathology of the jejenum showing necrosis and hyphae consistent with Aspergillus
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Image A. Multiple small lesions at both ends of the cordae tendinae in this patient who died of disseminated aspergillosis. He was a previously well 70 year old man who developed pneumonia on holiday, required artificial ventilation and died with a rapidly progressive cavitating pneumonia. Autopsy showed disseminated aspergillosis.
Image B. Another lesion in pt DB, that histologically showed a mass of hyphae and fibrin.
Image C. Large destructive lesion on the mitral valve in patient DB.
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The patient was a 610 g twin male born by spontaneous normal vaginal delivery at 23 weeks and 4 days gestation. He was started on benzyl penicillin and gentamicin for sepsis. On day 3, he developed metabolic acidosis, hyponatremia, anemia, thrombocytopenia and jaundice and his antibiotics were changed to vancomycin, cefotaxime and fluconazole.
On day 10, multiple circular skin papules with white eschars were noted on his back (Figure A). A full septic screen was repeated including skin scraping and biopsy for urgent microscopy and culture. Microscopy of skin scrapes revealed fungal elements including hyphae and fruiting heads suggestive of Aspergillus spp (Figure B). Lipid amphotericin B was commenced and fluconazole was stopped. Skin scrapings on culture grew Aspergillus fumigatus. A diagnosis of primary cutaneous aspergillosis was made. The patient responded to oral posaconazole 6mg/kg/8 hourly. All lesions disappeared after 44 days and he continued with posaconazole until day 60.
Published case at Langan et al Pediatr Dermatol 2010 Jul-Aug 27 (4) 403-4
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