A mycotoxin with diverse biological activities
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Oosporein

Item No. 29173

Technical Information
Formal Name
2,2′,5,5′-tetrahydroxy-4,4′-dimethyl-[bi-1,4-cyclohexadien-1-yl]-3,3′,6,6′-tetrone
CAS Number
475-54-7
Synonyms
  • NSC 88466
Molecular Formula
C14H10O8
Formula Weight
Purity
≥70%
A solid
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
CC1=C(O)C(C(C2=C(O)C(C(C)=C(O)C2=O)=O)=C(O)C1=O)=O
InChi Code
InChI=1S/C14H10O8/c1-3-7(15)11(19)5(12(20)8(3)16)6-13(21)9(17)4(2)10(18)14(6)22/h15,17,20,22H,1-2H3
InChi Key
DHMPJEGFPQTNFX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Oosporein is a mycotoxin that has been found in Beauveria and has diverse biological activities.1,2 It is cytotoxic to Sf9 and Sf21 insect cells with 50% cytotoxic concentration (CC50) values of 4.23 and 10.43 µM, respectively.3 Oosporin induces lethality in day-old cockerels (LD50 = 6.12 mg/kg).4 It inhibits Na+/K+-, Ca2+-, and Mg2+-ATPase activities by 27, 52, and 100%, respectively, in equine erythrocyte ghosts when used at a concentration of 200 µg/ml.2 Oosporein inhibits herpes simplex 1 (HSV-1), but not HeLa cell or E. coli, DNA polymerase (IC50s = 75, 610, and >700 µM, respectively).5 It is active against the bacterium S. pneumoniae (MIC = 32 µg/ml) and the plant pathogenic fungus P. infestans (MIC = 16 µM).1,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wainwright, M., Betts, R.P., and Teale, D.M. Antibiotic activity of oosporein from Verticillium psalliotae. Trans. Br. Mycol. Soc. 86(1), 168-170 (1986).

    2. Jeffs, L.B., and Khachatourians, G.G. Toxic properties of Beauveria pigments on erythrocyte membranes. Toxicon. 35(8), 1351-1356 (1997).

    3. Arboleda Valencia, J.W., Gaitán Bustamante, A.L., Jiménez, A.V., et alCytotoxic activity of fungal metabolites from the pathogenic fungus Beauveria bassiana: An intraspecific evaluation of beauvericin production. Curr. Microbiol. 63(3), 306-312 (2011).

    4. Cole, R.J., Kirksey, J.W., Cutler, H.G., et alToxic effects of oosporein from Chaetomium trilaterale. J. Agric. Food Chem. 22(3), 517-520 (1974).

    5. Terry, B.J., Liu, W.C., Cianci, C.W., et alInhibition of herpes simplex virus type 1 DNA polymerase by the natural product oosporein. J. Antibiot. (Tokyo) 45(2), 286-288 (1992).

    6. Nagaoka, T., Nakata, K., Kouno, K., et alAntifungal activity of oosporein from an antagonistic fungus against Phytophthora infestans. Z. Naturforsch. C. J. Biosci. 59(3-4), 302-304 (2004).