Date: 26 November 2013
Secondary metabolites, structure diagram: Trivial name – secalonic acid D
Copyright: n/a
Notes:
Species: A. aculeatus, A. ochraceus, A. uvarumSystematic name: [7,7′-Bi-4aH-xanthene]-4a,4’a-dicarboxylic acid, 2,2′,3,3′,4,4′,9,9′-octahydro-1,1′,4,4′,8,8′-hexahydroxy-3,3′-dimethyl-9,9′-dioxo-, dimethyl ester, (3S,3’S,4R,4’R,4aR,4’aR)-Molecular formulae: C32 H30 O14Molecular weight: 638.581Chemical abstracts number: 35287-69-5Selected references: Andersen, Raymond; Buechi, George; Kobbe, Brunhilde; Demain, Arnold L. (Dep. Chem., Massachusetts Inst. Technol., Cambridge, Mass., USA). J. Org. Chem., 42(2), 352-3 (English) 1977.Kurobane I, Vining LC, McInnes AG. J Antibiot (Tokyo). 1979 Dec;32(12):1256-66. Biosynthetic relationships among the secalonic acids. Isolation of emodin, endocrocin and secalonic acids from Pyrenochaeta terrestris and Aspergillus aculeatus.Toxicity: mouse LD50 intraperitoneal 26500ug/kg (26.5mg/kg) EFFECTS: VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION LUNGS, THORAX, OR RESPIRATION: CHANGES IN PULMONARY VASCULAR RESISTANCE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Applied and Environmental Microbiology. Vol. 39, Pg. 285, 1980. mouse LD50 intravenous 25mg/kg (25mg/kg) EFFECTS: BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: FOOD INTAKE (ANIMAL) SKIN AND APPENDAGES (SKIN): HAIR: OTHER Journal of Toxicology and Environmental Health. Vol. 5, Pg. 1159, 1979.mouse LDLo oral 30mg/kg (30mg/kg) EFFECTS: SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION LIVER: HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 48, Pg. A14, 1979. rat LD50 oral 22mg/kg (22mg/kg) EFFECTS: SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION LIVER: HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 48, Pg.
Images library
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25/04/90 After itraconazole treatment. Major improvement, defined as a complete response, after 10 weeks therapy with itraconazole.
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Image A. Chest x-ray shows a single nodule in the left mid lung field.
Image B. This emphasises how chest x-rays in this context underestimate the extent of disease. The most anterior nodule has ground glass surrrounding the nodule, a halo sign. This diagnostic feature is missed on plain chest X-rays.
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Chest X ray after 4 days, prior to treatment, showing massive increase in volume of lesion (Fig 2)
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Image A. This patient, aged 25 years developed a non productive cough and dyspnoea in the context of late-stage AIDS, CMV disease with ganciclovir-induced neutropenia and receiving corticosteroids. His chest radiograph shows fine bilateral reticular lower-lobe shadowing. He then developed gastro-intestinal bleeding with a gastric ulcer which showed hyphae on biopsy. He then developed blindness of one eye and the globe of his eye perforated. Hyphae were seen and Aspergillus cultured from the vitreous aspirate.
Image B. This radiograph, taken 25 days after the first and 3 days before death, shows of fine bilateral lower-lobe reticular shadows progressing to nodules in all lung zones.
This patient was reported as patient 3 in Denning DW, Follansbee S, Scolaro M, Norris S, Edelstein D, Stevens DA. Pulmonary aspergillosis in the acquired immunodeficiency syndrome. N Engl J Med 1991; 324: 654-662.
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Further details
Image A. Bronchoscopy revealed Aspergillus on culture.
Image B. The ability of Aspergillus to cause pulmonary infarction, probably through direct angioinvasion in this case, is characteristic.
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(Fig 1) Chest radiograph with ‘classical’ appearance of a pulmonary infarction – a wedge-shaped lesion peripherally set against the pleura.
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Large soft left upper-lobe shadow of focal invasive pulmonary aspergillosis in leukaemia, that was missed on earlier radiographs but apparent retrospectively. Variable density of the lesion suggests cavitation, which would be clearly visible on a CT scan of the thorax.
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Severe unilateral invasive aspergillosis of the left lung, with complete consolidation of the left lower-lobe and reticular shadowing extending up into the left upper lobe. The right lung appears normal.