Date: 26 November 2013
Secondary metabolites, 3D structure: Trivial name – citreoviridin
Copyright: n/a
Notes:
Species: A. terreusSystematic 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: C23H30O6Molecular weight: 402.481Chemical abstracts number: 25425-12-1Selected references: Franck B, Gehrken HP. Angew Chem Int Ed Engl. 1980;19(6):461-2 Citreoviridins from Aspergillus terreus.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.
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Image A
CT Scan 30/3/99
Showing extreme pleural thickening and 2 small cavities at apex of left lung.
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A 43 year old with smoking related emphysema was admitted to hospital with two separate episodes of haemoptysis. He had been in good health up to 1989, when he was diagnosed as having bilateral pulmonary tuberculosis. At that time a CT scan revealed a cavity in the left upper lobe (20.8cm2) with adjacent confluent infiltrates and pleural thickening. On bronchoscopic examination no abnormalities were noted and endobronchial biopsies did not reveal hyphae.
Over the next 4 years his condition deteriorated and a CT scan showed the left upper lobe cavity had increased to 40cm2. Itraconazole 400mg daily was prescribed. There was some clinical improvement on itraconazole but patient eventually deteriorated with breathlessness and with significant weight loss.
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