Oosporein

Oosporein
Names
	IUPAC name 2-(2,5-dihydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-3,6-dihydroxy-5-methylcyclohexa-2,5-diene-1,4-dione
	Other names NSC 88466; Chaetomidin; Iso-Oosporein; ;
Identifiers
CAS Number	475-54-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	13565485;
PubChem CID	135426831;
UNII	708AUK232A;
CompTox Dashboard (EPA)	DTXSID80963861 ;
	InChI 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 Key: DHMPJEGFPQTNFX-UHFFFAOYSA-N; Key: DHMPJEGFPQTNFX-UHFFFAOYSA-N;
	SMILES CC1=C(C(=O)C(=C(C1=O)O)C2=C(C(=O)C(=C(C2=O)O)C)O)O;
Properties
Chemical formula	C14H10O8
Molar mass	306.226 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

Oosporein is a toxic, bronze colored dibenzoquinone with the molecular formula C₁₄H₁₀O₈.^[2]^[3] Oosporein was first extracted from various molds and has antibiotic,^[4] antiviral, cytotoxic, antifungal, and Insecticide properties.^[3]^[5]^[2]

References

^ "Oosporein (CAS 475-54-7)". www.caymanchem.com.
^ ^a ^b ^c ^d Eisenbrand, Gerhard; Schreier, Peter (14 May 2014). RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006 (in German). Georg Thieme Verlag. p. 824. ISBN 978-3-13-179282-2.
^ ^a ^b Feng, Peng; Shang, Yanfang; Cen, Kai; Wang, Chengshu (8 September 2015). "Fungal biosynthesis of the bibenzoquinone oosporein to evade insect immunity". Proceedings of the National Academy of Sciences. 112 (36): 11365–11370. Bibcode:2015PNAS..11211365F. doi:10.1073/pnas.1503200112. PMC 4568701. PMID 26305932.
^ Handbook of Applied Mycology: Volume 2: Humans, Animals and Insects. CRC Press. 25 July 1991. p. 626. ISBN 978-0-8247-8435-5.
^ Ramesha, Alurappa; Venkataramana, M.; Nirmaladevi, Dhamodaran; Gupta, Vijai K.; Chandranayaka, S.; Srinivas, Chowdappa (1 September 2015). "Cytotoxic effects of oosporein isolated from endophytic fungus Cochliobolus kusanoi". Frontiers in Microbiology. 6: 870. doi:10.3389/fmicb.2015.00870. PMC 4556033. PMID 26388840.

Mc Namara, Louise; Dolan, Stephen K.; Walsh, John M.D.; Stephens, John C.; Glare, Travis R.; Kavanagh, Kevin; Griffin, Christine T. (August 2019). "Oosporein, an abundant metabolite in Beauveria caledonica, with a feedback induction mechanism and a role in insect virulence" (PDF). Fungal Biology. 123 (8): 601–610. Bibcode:2019FunB..123..601M. doi:10.1016/j.funbio.2019.01.004. PMID 31345414. S2CID 92167627.
Kögl, F.; van Wessem, G. C. (1944). "Untersuchungen über Pilzfarbstoffe XIV : Über Oosporein, den Farbstoff von Oospora colorans van Beyma". Recueil des Travaux Chimiques des Pays-Bas. 63 (1): 5–12. doi:10.1002/recl.19440630102.
Ross, P. Frank; Osheim, David L.; Rottinghaus, George E. (July 1989). "Mass Spectral Confirmation of Oosporein in Poultry Rations". Journal of Veterinary Diagnostic Investigation. 1 (3): 271–272. doi:10.1177/104063878900100317. PMID 2488354.
Canadian Journal of Biochemistry. National Research Council of Canada. p. 562.
Smith, DUPLICATE; Henderson, Rachel (23 July 1991). Mycotoxins and Animal Foods. CRC Press. p. 586. ISBN 978-0-8493-4904-1.

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