Quercinol, an anti-inflammatory chromene from the wood-rotting fungus Daedalea quercina (Oak Mazegill).
The fungus Daedalea quercina (oak mazegill) was examined for its capability of producing antioxidative and anti-inflammatory compounds. Bioactivity guided fractionation of the extract from a mycelial culture led to the isolation of quercinol, which was identified as (-)-(2S)-2-hydroxymethyl-2-methyl-6-hydroxychromene 1 by NMR and X-ray analyses. The cryptic hydroquinone 1 shows a broad anti-inflammatory activity against cyclooxygenase 2 (COX-2), xanthine oxidase (XO), and horseradish peroxidase (HRP) at micromolar concentrations.
Gebhardt
P
P
Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena, Germany.
Dornberger
K
K
Gollmick
F A
FA
Gräfe
U
U
Härtl
A
A
Görls
H
H
Schlegel
B
B
Hertweck
C
C
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001487:Basidiomycota / Q000378:metabolism*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018360:Crystallography, X-Ray; D051546:Cyclooxygenase 2 / Q000737:chemistry; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology; D015195:Drug Design; D006735:Horseradish Peroxidase / Q000037:antagonists & inhibitors; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors
D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D016861:Cyclooxygenase Inhibitors; C520998:quercinol; D006735:Horseradish Peroxidase; D051546:Cyclooxygenase 2; D014969:Xanthine Oxidase