Viridicatumtoxin B
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
(1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| C30H29NO10 | |
| Molar mass | 563.559 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Viridicatumtoxin B is a fungus-derived tetracycline-like antibiotic discovered in 2008. It was isolated from small amounts of penicillium fungi.[1]
Analogs lacking a hydroxyl group were even more effective than the original against Gram-positive bacteria.[1]
Concerns about solubility, biodegradation, availability and other issues must be resolved before clinical development begins.[1]
The substance was first isolated from the mycelium of liquid fermentation cultures of Penicillium species FR11.[2]
Structure
Based on mass spectrometry and nuclear magnetic resonance data, the substance was originally thought to be the 11a',12'-epoxide,[2] but the structure was later revised.[3]
Effects
Viridicatumtoxin B inhibited the growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus with a minimum inhibitory concentration of 0.5 μg/ml. That effect is similar to that of vancomycin, but 8 to 64 times greater than that of tetracycline.[2]
