Gliotoxin

Gliotoxin
Skeletal formula of gliotoxin
Space-filling model of the gliotoxin molecule
Names
IUPAC name
(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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.163.992 Edit this at Wikidata
UNII
  • InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1 checkY
    Key: FIVPIPIDMRVLAY-RBJBARPLSA-N checkY
  • InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
    Key: FIVPIPIDMRVLAY-RBJBARPLBT
  • Key: FIVPIPIDMRVLAY-RBJBARPLSA-N
  • O=C1N([C@@]2(SS[C@@]14N(C2=O)[C@H]3C(=C\C=C/[C@@H]3O)/C4)CO)C
Properties
C13H14N2O4S2
Molar mass 326.39 g·mol−1
Appearance White to light yellow solid
Density 1.75 g/ml
Solubility in DMSO soluble
Hazards
Safety data sheet (SDS) MSDS from Fermentek
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines[1] produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics.[2] Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of the most abundantly produced metabolites in human invasive Aspergillosis (IA).[3]

  1. ^ Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  2. ^ Jiang CS, Muller WE, Schroder HC, Guo YW (2012). "Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms". Chem. Rev. 112 (4): 2179–2207. doi:10.1021/cr200173z. PMID 22176580.
  3. ^ Lewis RE, Wiederhold NP, Chi J, Han XY, Komanduri KV, Kontoyiannis DP, Prince RA (January 2005). "Detection of Gliotoxin in Experimental and Human Aspergillosis". Infection and Immunity. 73 (1): 635–637. doi:10.1128/IAI.73.1.635-637.2005. PMC 538950. PMID 15618207.