Date: 26 November 2013
Secondary metabolites, 3D structure: Trivial name – versicolorin A
Copyright: n/a
Notes:
Species: A. flavus, A. versicolorSystematic name; Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, Z-(-)- Z-(-)-4,6,8-Trihydroxy-3a,12a-dihydroanthra(2,3-b)furo(3,2-d)furan-5,10-dione 4,6,8-Trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione Anthra[2,3-b]furo[3Molecular formulae: C18H10O7Molecular weight: 338.268Chemical abstracts number: 6807-96-1Selected references: Mori H, Kitamura J, Sugie S, Kawai K, Hamasaki T. Genotoxicity of fungal metabolites related to aflatoxin B1 biosynthesis. Mutat Res. 1985 Jul;143(3):121-5. Anderson MS, Dutton MF. Biosynthesis of versicolorin A. Appl Environ Microbiol. 1980 Oct;40(4):706-9.Toxicity: Little or no recorded toxicity in vertebrates but important as a representative of a group of metabolites which are precursors of the aflatoxins and sterigmatocystins.mouse LD50 intravenous 20mg/kg (20mg/kg) CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 3, Pg. 189, 1980. Bennett JW, Christensen SB. New perspectives on aflatoxin biosynthesis. Adv Appl Microbiol. 1983;29:53-92.
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Macroscopic view medial aspect of left upper lobe of lung showing segmental collapse and congestion of lower segments, with mucus extruding from incised bronchi.
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Born 75 years ago, Pt HK had 3 episodes of tuberculosis as a child and teenager, being treated with PAS and streptomycin. He suffered a ‘bad chest’ all his life and retired aged 54. Presenting with worsening and more frequent chest infections, he was referred with ‘bronchiectasis and Aspergillus sensitisation’. A diagnosis of chronic pulmonary aspergillosis was made in June 2009 on the basis of his chest radiograph and strongly positive Aspergillus precipitins (IgG antibodies) (titre 1/16). He also had Pseudomonas aeruginosa colonisation. His oxygen saturation was 87% and his pO2 6.8, pCO2 6.2 KPa.
His chest radiograph (see above, November 2009) was reported as showing; “ The lung fields are over-inflated. Bilateral apical fibrotic change secondary to old TB. No cavity seen.” At clinic, bilateral apical cavities were seen, with some associated pleural thickening at the left apex, without any evidence of a fungal ball.
He started posaconazole 400mg twice daily with therapeutic levels at subsequent visits. Sputum cultures never grew Aspergillus. Over the following 9 months he had no chest infections requiring antibiotics, his breathlessness worsened gradually and he remained easily fatigued. His Aspergillus antibody titres fell. Overall he felt better, but was concerned about declining respiratory status.
