Cytochalasin E

ID 2: 475

Toxin: y

Trivial name:

21,​23-​Dioxa[13]​cytochalasa-​13,​19-​diene-​1,​17,​22-​trione, 6,​7-​epoxy-​18-​hydroxy-​16,​18-​dimethyl-​10-​phenyl-​, (7S,​13E,​16S,​18R,​19E)​-; Cytochalasin E; NSC 175151; [1,​3]​Dioxacyclotridecino[​4,​5-​d]​oxireno[f]​isoindole-​5,​10,​12(4H,​6H)​-​trione, 3,​13,​14,​14a,​15,​15a,​16a,​16b-​octahydro-​6-​hydroxy-​4,​6,​15,​15a-​tetramethyl-​14-​(phenylmethyl)​-​, [4S-​(1E,​4R*,​6S*,​7E,​11aR*,​14R*,​14aR*,​15R*,​15aS*,​16aR*,​16bR*)​]​-

Systematic name:

14-Benzyl-6-hydroxy-4,6,15,15a-tetramethyl-3,13,14,14a,15,15a,16a,16b-octahydro[1,3]dioxacyclotridecino[4,5-d]oxireno[2,3-f]isoindole-5,10,12(4H,6H)-trione

Molecular formulae: 

C₂₈H₃₃NO₇

Molecular weight: 495.57

Chemical abstract number: 36011-19-5

Chemical type: Alkaloid

Literature reference:

• Structure of cytochalasin E, a toxic metabolite of Aspergillus clavatus, Buechi, George; Kitaura, Yoshihiko; Yuan, Sun-Shine; Wright, Hal E.; Clardy, Jon; Demain, Arnold L.; Glinsukon, Thirayudh; Hunt, Nadine; Wogan, Gerald N. Journal of the American Chemical Society (1973), 95(16), 5423-5.
  Production of cytochalasin E by Aspergillus terreus. Fujishima, T.; Ichikawa, M.; Ishige, H.; Yoshino, H.; Ohishi, J.; Ikegami, S. Hakko Kogaku Kaishi (1979), 57(1), 15-19.

References URL: 

• http://pubchem.ncbi.nlm.nih.gov/compound/5458385
• http://pubs.acs.org/doi/pdf/10.1021/ja00797a060?source=chemport&cookieSet=1&cookieSet=1&cookieSet=1&cookieSet=1

Aspergillus Species known to produce this metabolite:

• /species/clavatus
• /species/a-terreus

Toxicity:

The cytochalasins inhibit cleavage in cultured animal cells leading to the formation of multinucleated cells and cells without nuclei. Cytochalasin E is one of the most acutely toxic of the group causing necrosis of many body organs and pulmonary haemorrhage. Oral LD50 in rats 9.1 mg/kg body-weight.

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

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Mycotoxin & Metabolites

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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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