Isolation and characterization of substituted 4-hydroxy-cyclohex-2-enones as metabolites of 3,4-dimethoxybenzyl alcohol and its methyl ether in ligninolytic cultures of Phanerochaete chrysosporium |
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Authors: | Urs M Tuor Hans E Schoemaker Matti S A Leisola Harald W H Schmidt |
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Institution: | (1) Department of Biotechnology, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093 Zürich, Switzerland;(2) Bio-Organic Chemistry Section, DSM Research, P.O. Box 18, NL-6160 MD Geleen, The Netherlands;(3) Research Center, Cultor Ltd., SF-02 460 Kantvik, Finland;(4) Givaudan-Roure Forschungsgesellschaft AG, CH-8600 Dübendorf, Switzerland |
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Abstract: | The metabolism of quinones formed in the enzymatic oxidation of veratryl alcohol (3,4-dimethoxybenzyl alcohol) (Ia) and its methyl ether Ib in ligninolytic cultures of Phanerochaete chrysosporium was studied. A metabolite of 2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione (IIa, formed from Ia by oxidation) was isolated and identified as cis-4-hydroxy-6-hydroxymethyl-3-methoxy-cyclohex-2-en-one (IVa), formally the reduced hydroquinone IIIa. The formation of IVa was also observed when both veratryl alcohol Ia or 2,5-dihydroxy-4-methoxybenzyl alcohol (IIIa), the hydroquinone of IIa, were used as substrates. Analogously, cis-4-hydroxy-3-methoxy-6-methoxymethyl-cyclohex-2-en-one (IVc) was isolated and identified as a metabolite from either 3,4-dimethoxybenzyl methyl ether (Ib) or from its oxidation product 5-methoxy-2-methoxymethyl-2,5-cyclohexadiene-1,4-dione (IIb) as well as from the corresponding hydroquinone 2,5-dihydroxy-4-methoxybenzyl methyl ether (IIIc). The physiological role of these unprecedented conversions is discussed.
Correspondence to: H. E. Schoemaker |
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