Gliotoxin

Title: Gliotoxin
CAS Registry Number: 67-99-2
CAS Name: (3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Molecular Formula: C13H14N2O4S2
Molecular Weight: 326.39
Percent Composition: C 47.84%, H 4.32%, N 8.58%, O 19.61%, S 19.65%
Literature References: Antibiotic substance produced by various spp of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium spp: Weindling, Emerson, Phytopathology 26, 1068 (1936); 27, 1175 (1937); Johnson et al., J. Am. Chem. Soc. 65, 2005 (1943); Menzel et al., J. Biol. Chem. 152, 419 (1944). Structure: Bell et al., J. Am. Chem. Soc. 80, 1001 (1958); Beecham et al., Tetrahedron Lett. 1966, 3131. Crystallographic data: McCrone, Anal. Chem. 26, 1662 (1954). Biosynthesis: Suhadolnik, Chenoweth, J. Am. Chem. Soc. 80, 4391 (1958); Winstead, Suhadolnik, ibid. 82, 1644 (1960); J. D. M. Herscheid et al., J. Org. Chem. 45, 1885 (1980). Synthetic studies: Poisel, Schmidt, Ber. 104, 1714 (1971); ibid. 105, 625 (1972); Oehler et al., ibid. 625. Total synthesis of dl-form: T. Fukuyama, Y. Kishi, J. Am. Chem. Soc. 98, 6723 (1976); T. Fukuyama et al., Tetrahedron 37, 2045 (1981).
Properties: Monoclinic needles from methanol or benzene, dec 221°. [a]D25 -290° (c = 0.08 in ethanol). uv max: 270 nm (e 4500). Soly in mg/ml at 7°: acetic acid 12; acetone 9.0; acetonitrile 10.2; benzene 5.5; carbon tetrachloride 0.8; chloroform 20; dioxane 73 (decompn); dimethylformamide 17; ethyl acetate 8.5; ethanol 4.7; methanol 1.4; pyridine 77; water (30°): 0.07. Sensitive to oxidation and heat; inactivated by heating for 10 min at 100°.
Optical Rotation: [a]D25 -290° (c = 0.08 in ethanol)
Absorption maximum: uv max: 270 nm (e 4500)
Derivative Type: Monoacetate
Molecular Formula: C15H16N2O5S2
Molecular Weight: 368.43
Percent Composition: C 48.90%, H 4.38%, N 7.60%, O 21.71%, S 17.41%
Literature References: Isolated from cultures of Penicillium terlikowski Zaleski: Johnson et al., J. Am. Chem. Soc. 75, 2110 (1953).
Properties: Orthorhombic crystals from benzene, mp 162-163°.
Melting point: mp 162-163°
Glipizide Gliquidone Glisoxepid Globin Glucagon

Gliotoxin
Gliotoxin.png
Identifiers
CAS number 67-99-2 YesY
PubChem 6223
ChemSpider 5988 YesY
ChEMBL CHEMBL331627 YesY, CHEMBL145588
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
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]