Viridicatumtoxin A (also simply called viridicatumtoxin) is a fungus-derived tetracycline-like antibiotic, whose chemical structure was determined in 1976.[1][2] It is found in Penicillium viridicatum,[1] Penicillium aethiopicum,[2] among other fungi.
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| Preferred IUPAC name
(1S,7′aS,11′aS,12′S)-5′,6′,7′a,8′,11′a,12′-Hexahydroxy-3′-methoxy-2,6,6-trimethyl-7′,10′-dioxo-7′,7′a,10′,11′,11′a,12′-hexahydro-1′H-spiro[cyclohexane-1,2′-cyclopenta[de]tetracen]-2-ene-9′-carboxamide | |
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3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C30H31NO10 | |
| Molar mass | 565.575 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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Like viridicatumtoxin B, viridicatumtoxin A inhibits growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus, with an activity 8 to 64 times greater than that of tetracycline.[2]
References
edit- ^ a b Raju, M. S.; Wu, G.-S.; Gard, A.; Rosazza, J. P. (1982). "Microbial Transformations of Natural Antitumor Agents. 20. Glucosylation of Viridicatumtoxin". Journal of Natural Products. 45 (3): 321. doi:10.1021/np50021a014.
- ^ a b c Chooi, Yit-Heng; Cacho, Ralph; Tang, Yi (2010). "Identification of the Viridicatumtoxin and Griseofulvin Gene Clusters from Penicillium aethiopicum". Chemistry & Biology. 17 (5): 483–494. doi:10.1016/j.chembiol.2010.03.015. PMC 2884005. PMID 20534346.
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