Viridicatumtoxin A

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.

"Viridicatumtoxin" redirects here. For the related substance, see Viridicatumtoxin B.
Viridicatumtoxin A
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32-35,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28-,29-,30+/m0/s1
    Key: SUWQGLGDFGHZNH-WBWZXODPSA-N
  • CC1=CCC[C@@]([C@]12c3c4c(c(c5c(c4C2)[C@@H]([C@@]6([C@](C5=O)(C(=O)C(=C(C6)O)C(=O)N)O)O)O)O)c(cc3OC)O)(C)C
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).
Infobox references

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
  1. 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.
  2. 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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