Abstract
Fusarium solani M-13-1 was shake-cultured in a medium containing guaiacylglycerol-β-coniferyl ether (I), a model compound representing the arylglycerol-β-aryl ether linkage in lignin, as sole carbon source. From the culture filtrate guaiacylglycerol-β-coniferyl aldehyde ether (II) and guaiacylglycerol-β-ferulic acid ether (III) were isolated as metabolic products. Incubation with (III) resulted in formation of guaiacylglycerol-β-vanillin ether (IV), which was further metabolized to guaiacyglycerol-β-vanillic acid ether (V). The results indicate that the cinnamyl alcohol group of (I) is initially oxidized to an aldehyde group, which is further oxidized to a carboxyl group, yielding (II) and (III). Compound (III) is converted to (IV) by the release of a C2 fragment, and the aldehyde group of (IV) is further oxidized to a carboxyl group, giving (V). In the pathway from (I) to (V), neither oxidation of the benzylic secondary alcohol to ketone nor cleavage of the arylglycerol-β-aryl ether linkage was observed. The fungus was found to attack both erythro and threo form without distinction.
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Abbreviations
- DHP:
-
dehydrogenation polymer
- DHCA:
-
dehydrodiconiferyl alcohol
- TLC:
-
thin layer chromatography
- AT:
-
aromatic
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Katayama, T., Nakatsubo, F. & Higuchi, T. Initial reactions in the fungal degradation of guaiacylglycerol-β-coniferyl ether, a lignin substructure model. Arch. Microbiol. 126, 127–132 (1980). https://doi.org/10.1007/BF00511217
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DOI: https://doi.org/10.1007/BF00511217