Cytochalasin E

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

Chem abstract number: 

36011-19-5

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.

Chemical type: 

Alkaloid

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.

Structure image: 

Aspergillus Species known to produce this metabolite: 

Date uploaded: 

2005-12-13 00:00:00