Abstract
The degradation of the phenylcoumaran substructure model compound methyl dehydrodiconiferyl alcohol by the white-rot wood decay fungus Phanerochaete chrysosporium was investigated using culture conditions optimized for lignin oxidation. Initial attack was in the cinnamyl alcohol side chain, which was oxidized to a glycerol structure. This was subsequently converted by loss of the two terminal carbon atoms, Cβ′ and Cγ′, to yield a Cα′-aldehyde structure, which was further oxidized to the Cα′-acid compound. The next detected intermediate, a phenylcoumarone, was produced by double bond formation between Cα and Cβ, and oxidation of the Cγ-alcohol to an aldehyde group. Further oxidation of Cγ to an acid yielded the next intermediate. The final identified degradation product was veratric acid. No products from the 5-substituted aromatic ring, and no phenolic products, were found. The initial glycerol-containing intermediate was a mixture of the threo and erythro forms, and no optical activity could be found, suggesting that its formation might have involved nonstereospecific Cα′-Cβ′ epoxidation followed by non-enzymatic hydrolysis of the epoxide.
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Abbreviations
- TLC:
-
thin layer chromatography
- LDA:
-
lithium diisopropyl amide
- DDQ:
-
2,3-dichloro-5,6-dicyanobenzoquinone
- MS:
-
mass spectrometry
- UV:
-
ultraviolet spectroscopy
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Nakatsubo, F., Kirk, T.K., Shimada, M. et al. Metabolism of a phenylcoumaran substructure lignin model compound in ligninolytic cultures of Phanerochaete chrysosporium . Arch Microbiol 128, 416–420 (1981). https://doi.org/10.1007/BF00405924
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DOI: https://doi.org/10.1007/BF00405924