De novo synthesis of 4,5-dimethoxycatechol and 2,5-dimethoxyhydroquinone by the brown rot fungus Gloeophyllum trabeum

The new dimethoxycatechol 4,5-dimethoxy-1,2-benzenediol (DMC) and the new d imethoxyhydroquinone 2,5-dimethoxy-1,4-benzenediol (DMW) were isolated from stationary cultures of the brown rot fungus Gloeophyllum trabeum growing o n a glucose mineral medium protected from light. The structure was elucidat ed by gas chromatography-mass spectrometry through comparison to a syntheti c standard. Further confirmation was obtained by forming a dimethoxyoxazole derivative by condensation of DMC with methylene chloride and through exam ination of methylated derivatives. DMC and DMH may serve as ferric chelator s, oxygen-reducing agents, and redox-cycling molecules, which would include functioning as electron transport carriers to Fenton's reactions. Thus, th ey appear to be important components of the brown rot decay system of the f ungus.