Fumagillin

ID 2: 488

Toxin: y

Trivial name:

2,​4,​6,​8-​Decatetraenedioic acid 4-​(1,​2-​epoxy-​1,​5-​dimethyl-​4-​hexenyl)​-​5-​methoxy-​1-​oxaspiro[2.5]​oct-​6-​yl ester (6CI); 2,​4,​6,​8-​Decatetraenedioic acid, mono[(3R,​4S,​5S,​6R)​-​5-​methoxy-​4-​[(2R,​3R)​-​2-​methyl-​3-​(3-​methyl-​2-​butenyl)​oxiranyl]​-​1-​oxaspiro[2.5]​oct-​6-​yl] ester, (2E,​4E,​6E,​8E)​- (9CI); 2,​4,​6,​8-​Decatetraenedioic acid, mono[4-​(1,​2-​epoxy-​1,​5-​dimethyl-​4-​hexenyl)​-​5-​methoxy-​1-​oxaspiro[2.5]​oct-​6-​yl] ester (8CI); 2,​4,​6,​8-​Decatetraenedioic acid, mono[5-​methoxy-​4-​[2-​methyl-​3-​(3-​methyl-​2-​butenyl)​oxiranyl]​-​1-​oxaspiro[2.5]​oct-​6-​yl] ester, [3R-​[3α,​4α(2R*,​3R*)​,​5β,​6β(2E,​4E,​6E,​8E)​]​]​-; 1-​Oxaspiro[2.5]​octane, 2,​4,​6,​8-​decatetraenedioic acid deriv.; (-​)​-​Fumagillin; Amebacilin; Fugillin; Fumadil B; Fumagillin; Fumagillin DCH; Fumidil; NSC 9168; ZGN 201

Systematic name:

2,​4,​6,​8-​Decatetraenedioic acid, 1-​[(3R,​4S,​5S,​6R)​-​5-​methoxy-​4-​[(2R,​3R)​-​2-​methyl-​3-​(3-​methyl-​2-​buten-​1-​yl)​-​2-​oxiranyl]​-​1-​oxaspiro[2.5]​oct-​6-​yl] ester, (2E,​4E,​6E,​8E)​-

Molecular formulae: 

C₂₆H₃₄O₇

Molecular weight: 458.55

Chemical abstract number: 23110-15-8

Chemical type: Cyclohexane derivative

Literature reference:

• Fumagillin, an antibiotic from Aspergillus funigatus H-​3. EBLE T E; HANSON F R. Antibiotics & chemotherapy (1951), 1(1), 54-8.
  Aspergillus, angiogenesis, and obesity: the story behind beloranib. Howland RH. J Psychosoc Nurs Ment Health Serv. 2015 Mar 1;53(3):13-6. doi: 10.3928/02793695-20150219-01.

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/6917655

Aspergillus Species known to produce this metabolite:

• /species/a-fumigatus

Toxicity:

Originally isolated because of its antibiotic properties, especially against protozoa such as Entamoeba histolytica. LD50 in mice 800 mg/kg body-weight subcutaneously although as much as 2 mg/kg body-weight could be tolerated orally.

Date uploaded: 2005-12-13 00:00:00

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Mycotoxin & Metabolites

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