De Novo Synthesis of 1,5-Dimethoxy Catechol by the Brown-Rot Fungus Gloeophyllum trabeum.
Publication Name: Applied and Environmental Microbiology
Publication URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC91078/
The new dimethoxycatechol 4,5-dimethoxy-1,2-benzenediol (DMC) and the new dimethoxyhydroquinone 2,5-dimethoxy-1,4-benzenediol (DMH) were isolated from stationary cultures of the brown rot fungus Gloeophyllum trabeum growing on a glucose mineral medium protected from light. The structure was elucidated by gas chromatography-mass spectrometry through comparison to a synthetic standard. Further confirmation was obtained by forming a dimethoxyoxazole derivative by condensation of DMC with methylene chloride and through examination of methylated derivatives. DMC and DMH may serve as ferric chelators, oxygen-reducing agents, and redox-cycling molecules, which would include functioning as electron transport carriers to Fentons reactions. Thus, they appear to be important components of the brown rot decay system of the fungus.