Citreoviridin

Toxin: 

y

Trivial name: 

2,​4,​6,​8,​10,​12-​Tridecahexaenoic acid, 5-​hydroxy-​3-​methoxy-​4,​12-​dimethyl-​13-​(tetrahydro-​3,​4-​dihydroxy-​2,​4,​5-​trimethyl-​2-​furyl)​-​, δ-​lactone (7CI); 2H-​Pyran-​2-​one, 4-​methoxy-​5-​methyl-​6-​[7-​methyl-​8-​(tetrahydro-​3,​4-​dihydroxy-​2,​4,​5-​trimethyl-​2-​furanyl)​-​1,​3,​5,​7-​octatetraenyl]​-​, [2S-​[2α(1E,​3E,​5E,​7E)​,​3β,​4α,​5α]​]​-; 2H-​Pyran-​2-​one, 4-​methoxy-​5-​methyl-​6-​[7-​methyl-​8-​(tetrahydro-​3,​4-​dihydroxy-​2,​4,​5-​trimethyl-​2-​furyl)​-​1,​3,​5,​7-​octatetraenyl]​- (8CI); D-​Iditol, 2,​5-​anhydro-​1,​6-​dideoxy-​2-​C-​[(1E,​3E,​5E,​7E)​-​8-​(4-​methoxy-​5-​methyl-​2-​oxo-​2H-​pyran-​6-​yl)​-​2-​methyl-​1,​3,​5,​7-​octatetraenyl]​-​4-​C-​methyl- (9CI); Citreoviridin; Citreoviridin A; Citreoviridine; Citreoviridine A

Systematic name: 

D-Iditol, 2,5-anhydro-1,6-dideoxy-2-C-[(1E,3E,5E,7E)-8-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)-2-methyl-1,3,5,7-octatetraenyl]-4-C-methyl- (9CI)

Molecular formulae: 

C23H30O6

Molecular weight: 

402.48

Chem abstract number: 

25425-12-1

Literature reference: 

Toxic metabolites of the fungi isolated from homemade miso. Yamazaki, Mikio; Horie, Yoshikazu; Suzuki, Shigetoshi; Fujimoto, Haruhiro; Maebayashi, Yukio; Miyaki, Komei; Hatakeyama, Sadao. Shokuhin Eiseigaku Zasshi (1971), 12(5), 370-5.Franck B, Gehrken HP. Angew Chem Int Ed Engl. 1980;19(6):461-2 Occurrence of toxin-​producing molds in cereals of different sources. Bauer, J.; Gedek, B. Landwirtschaftliche Forschung, Sonderheft (1978), 35, 562-9. Citreoviridins from Aspergillus terreus. Franck B; Gehrken H P. Angewandte Chemie (International ed. in English) (1980), 19(6), 461-2.

Toxicity: 

Citreoviridin is produced by P. citreonigrum (synonyms P. citreoviride and P. toxicarium), particularly in rice after harvest. It can cause cardiac beriberi in man. Acute cardiac beriberi in Japan is now only of historical interest although P. citreonigrum and citreoviridin are still reported in other parts of Asia. The fungus is said to be favoured by the lower temperatures and shorter hours of daylight occurring in the more temperate rice growing areas. The toxin is also produced by P. ochrosalmoneum. Citreoviridin has been found in un-harvested corn in the USA. Citreoviridin is an unusual molecule consisting of a lactone ring conjugated to a furan ring, with a molecular weight of 402. It is a neurotoxin. Nishie K, Cole RJ, Dorner JW. Res Commun Chem Pathol Pharmacol. 1988 Jan;59(1):31-52.Toxicity of citreoviridin.

Structure image: 

Aspergillus Species known to produce this metabolite: 

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Date uploaded: 

2005-12-11 00:00:00