Involutin

Involutin
Names
Preferred IUPAC name
(4S,5R)-5-(3,4-Dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)cyclopent-2-en-1-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C17H14O6/c18-10-4-1-8(2-5-10)13-15(21)14(17(23)16(13)22)9-3-6-11(19)12(20)7-9/h1-7,13,16,18-20,22-23H
    Key: JDHDWVVITVZZFY-UHFFFAOYSA-N
  • O[C@H]1[C@H](C(=O)C(=C1O)C1=CC=C(O)C=C1)C1=CC=C(O)C(O)=C1
Properties
C17H14O6
Molar mass 314.293 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Involutin is an organic compound that can be found in mushrooms belonging to the genus Paxillus. It is part of a class of compounds known as diarylcyclopentenones. It is derived from atromentin which was shown from 3′,3″,5′,5″-d4-atromentin (deuterated atromentin) feeding studies and observing the deuterated incorporation into two atromentin derivatives (i.e., an increase in monoisotopic mass by 4 mass units), gyrocyanin and its oxidation product gyroporin.[1] It has been shown to be a Fe3+-reductant and presumed to be involved in Fenton chemistry for the initial attack of dead plant matter.[2]

References

  1. ^ Braesel, J; Götze, S; Shah, F; Heine, D; Tauber, J; Hertweck, C; Tunlid, A; Stallforth, P; Hoffmeister, D (2015). "Three Redundant Synthetases Secure Redox-Active Pigment Production in the Basidiomycete Paxillus involutus". Chemistry & Biology. 22 (10): 1325–34. doi:10.1016/j.chembiol.2015.08.016. PMID 26496685.
  2. ^ Shah, F; Schwenk, D; Nicolás, C; Persson, P; Hoffmeister, D; Tunlid, A (2015). "Involutin is an Fe3+ Reductant Secreted by the Ectomycorrhizal Fungus Paxillus involutus during Fenton-Based Decomposition of Organic Matter". Applied and Environmental Microbiology. 81 (24): 8427–8433. doi:10.1128/AEM.02312-15. PMC 4644656. PMID 26431968.


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