Oosporein

Last updated
Oosporein
Oosporein.svg
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 [1]
    • Chaetomidin [2]
    • Iso-Oosporein [2]
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • CC1=C(C(=O)C(=C(C1=O)O)C2=C(C(=O)C(=C(C2=O)O)C)O)O
Properties
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).

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]

Related Research Articles

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References

  1. "Oosporein (CAS 475-54-7)". www.caymanchem.com.
  2. 1 2 3 4 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.
  3. 1 2 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. doi: 10.1073/pnas.1503200112 . PMC   4568701 . PMID   26305932.
  4. Handbook of Applied Mycology: Volume 2: Humans, Animals and Insects. CRC Press. p. 626. ISBN   978-0-8247-8435-5.
  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.

Further reading