| Identification | Back Directory | [Name]
viridicatumtoxin | [CAS]
39277-41-3 | [Synonyms]
NSC 159628 viridicatumtoxin Spiro[2-cyclohexene-1,2'(1'H)-cyclopenta[de]naphthacene]-9'-carboxamide, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (1R,7'aR,11'aR,12'R)-rel-(-)- | [Molecular Formula]
C30H31NO10 | [MDL Number]
MFCD01675248 | [MOL File]
39277-41-3.mol | [Molecular Weight]
565.57 |
| Chemical Properties | Back Directory | [Melting point ]
235°C (rough estimate) | [Boiling point ]
630.75°C (rough estimate) | [density ]
1.3203 (rough estimate) | [refractive index ]
1.6310 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble | [form ]
A solid |
| Hazard Information | Back Directory | [Description]
Viridicatumtoxin in a mycotoxin originally isolated from Penicillium that has diverse biological activities, including antimicrobial, cytotoxic, and toxic properties. It inhibits the growth of B. subtilis, M. luteus, C. perfringens, B. fragilis, and methicillin-resistant S. aureus (MRSA; MICs = 0.39-1.56 μg/ml), as well as C. albicans, S. cerevisiae, M. racemosus, A. niger, and P. chrysogenum (MICs = 6.2-25 μg/ml), but has no activity against M. smegmatis, E. coli, K. pneumoniae, P. aeruginosa, or S. marcescens (MICs = >100 μg/ml). Viridicatumtoxin inhibits the production of polyprenyl alcohols by S. aureus undecaprenyl pyrophosphate (UPP) synthase, E. coli octaprenyl pyrophosphate synthase (OPS), and S. cerevisiae dehydrodolichyl pyrophosphate (DedoIPP) synthase in vitro (IC50s = 3.1, 21, and 71 μM, respectively). It has cytotoxic effects against human Jurkat T (IC50 = 4.92 μM), chronic lymphocytic leukemia (CLL; LC50 = 0.7-3.5 nM), and bone marrow-derived HS-5 stromal cells. Viridicatumtoxin is toxic to rats and mice when administered intraperitoneally (LD50s = 80 and 90 mg/kg, respectively) and to rats when administered via gastric intubation (LD50 = 122.4 mg/kg), but not to rats or mice when administered orally or through subcutaneous injection. | [Uses]
Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium, first isolated in 1976 as a mycotoxin. Initial testing revealed that viridicatumtoxin caused myocardial deterioration, renal tubule necrosis and spleen atrophy. Analogous to the related tetracyclines, viridicatumtoxin was found to be a potent antibacterial, with activity against S. aureus including MRSA and QRSA strains. Little has been published on the mode of action of viridicatumtoxin. | [Uses]
Viridicatumtoxin is a tetracycline-like metabolite produced by several species of Penicillium. | [Definition]
ChEBI: A tetracycline-like polyketide antibiotic that is produced by several species of Penicillium and Aspergillus. | [in vivo]
Viridicatumtoxin (60-400 mg/kg; i.p., p.o., s.c; ICR mice, Sprague-Dawley rats and mature Wistar rats (4/5 weeks; 16-20 g/140-150 g)) has no signs of toxicity with p.o. administration. As the dosage increasing (i.p. and p.o.), hepatocytes starts to have pathological changes and deaths occurrs in both mice and rats. Mice and rats which given the viridicatumtoxin by s.c. has no signs of toxicity and none die, but coagulation necrosis is present at the injection site[2]. | Animal Model: | ICR mice, Sprague-Dawley rats and mature Wistar rats (4/5 weeks; 16-20 g/140-150 g)[2] | | Dosage: | 60-400 mg/kg | | Administration: | i.p., p.o., s.c. | | Result: | Orally with viridicatumtoxin had no signs of toxicity. As the dosage increasing (i.p. and p.o.), hepatocytes started to have pathological changes and deaths occurred in both mice and rats. Mice and rats which given the viridicatumtoxin by s.c. had no signs of toxicity and none died, but coagulation necrosis was present at the injection site.
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| [References]
[1] R.D. HUTCHISON S. J van R P S Steyn. Viridicatumtoxin, a new mycotoxin from Penicillium viridicatum westling[J]. Toxicology and applied pharmacology, 1973, 24 3: Pages 507-509. DOI: 10.1016/0041-008x(73)90057-4 [2] JUNJI INOKOSHI. Inhibition of bacterial undecaprenyl pyrophosphate synthase by small fungal molecules[J]. Journal of Antibiotics, 2016, 69 11: 798-805. DOI: 10.1038/ja.2016.35 [3] ALISON M. BENDELE . Viridicatumtoxin mycotoxicosis in mice and rats[J]. Toxicology letters, 1984, 22 3: Pages 287-291. DOI: 10.1016/0378-4274(84)90103-6 |
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