?-Ether cleavage of the lignin model compound 4-ethoxy-3-methoxyphenylglycerol-?-guaiacyl ether and derivatives by Phanerochaete chrysosporium
- 1 April 1981
- journal article
- research article
- Published by Springer Science and Business Media LLC in Archiv für Mikrobiologie
- Vol. 129 (2), 141-145
- https://doi.org/10.1007/bf00455350
Abstract
The white rot basidiomycete Phanerochaete chrysosporium metabolized 4-ethoxy-3-methoxyphenyl-glycerol-β-guaiacyl ether (V) in low nitrogen, stationary cultures under which conditions the ligninolytic enzyme system is expressed. 4-Ethoxy-3-methoxyphenylglycerol XIII, guaicol and 4-ethoxy-3-methoxybenzyl alcohol (II) were isolated as metabolic products. Exogenously added XIII was rapidly converted to 4-ethoxy-3-methoxybenzyl alcohol indicating that it is an intermediate in the metabolism of V. P. chrysosporium also metabolized 1-(4′-ethoxy-3′-methoxyphenyl)-2-(2″-methoxyphenoxy)-3-hydroxypropane VI. The degradation pathway for this dimer also included initial β-ether cleavage and α-hydroxylation of the diol product 1-(4′-ethoxy-3′-methoxyphenyl) 2,3 dihydroxypropane (XI) to yield the triol XIII which was cleaved at the α, β bond to yield 4-ethoxy-3-methoxybenzyl alcohol. Finally P. chrysosporium also cleaved the dimer 1-(4′-ethoxy-3′-methoxyphenyl)-2-(2″-methoxyphenoxy)-1-hydroxypropane (VIII) at the β-ether linkage yielding 1-(4′-ethoxy-3′-methoxyphenyl) 1,2 dihydroxypropane (IX) which was subsequently cleaved at the α, β bond to yield II. All of the results indicate that oxidative β-ether cleavage is an important initial reaction in the metabolism of β-aryl ether lignin substructure dimeric compounds. Metabolities were identified after comparison with chemically synthesized standards by gas liquid chromatography-mass spectrometry.Keywords
This publication has 21 references indexed in Scilit:
- Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-?-guaiacyl ether by Phanerochaete chrysosporiumArchiv für Mikrobiologie, 1980
- Metabolism of the lignin model compounds veratrylglycerol-?-guaiacyl ether and 4-ethoxy-3-methoxyphenylglycerol-?-guaiacyl ether by Phanerochaete chrysosporiumArchiv für Mikrobiologie, 1980
- Ligninolytic system of Phanerochaete chrysosporium: Inhibition by o-PhthalateArchiv für Mikrobiologie, 1979
- Effects of Microorganisms on LigninAnnual Review of Phytopathology, 1971
- Enzymic degradation of lignin V. The effect of NADH on the enzymic cleavage of arylalkylether bond in veratrylglycerol-β-guaiacylether as lignin model compoundArchives of Biochemistry and Biophysics, 1969
- Oxidation of guaiacyl- and veratryl-glycerol-β-guaiacyl ether by polyporus versicolor and stereum frustulationBiochimica et Biophysica Acta (BBA) - General Subjects, 1968
- Investigations on lignins and lignificationArchives of Biochemistry and Biophysics, 1963
- Synthesis of A-NorcholesterolJournal of the American Chemical Society, 1961
- Notes- Method for the Cleavage of Osmate EstersThe Journal of Organic Chemistry, 1960
- The Preparation of Methyl EstersJournal of the American Chemical Society, 1948