Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid.
The white-rot fungus Pycnoporous cinnabarinus (DMS-1184) was submerged cultured for 22 days under controlled conditions in a bioreactor. After 6, 9, and 15 days of culture the growth medium was supplemented with [5-2H]-labelled ferulic acid (I). The major phenolic compounds identified labelled were four lignans, the methyl esters of ferulic (I) and vanillic acid (VIII), (E)-coniferyl aldehyde (II), (E)-coniferyl alcohol (III), vanillic acid (VIII), vanillin (IX) and vanillyl alcohol (X). The detection of considerable amounts of labelled 4-hydroxy-3-methoxyacetophenone (VII) in the late growth phase suggested the increasing formation and decarboxylation of free 4-hydroxy-3-methoxybenzoylacetic acid (VI) and, thus, a beta-oxidation-like degradation of ferulic acid (I) or its methyl ester to vanillic acid (VIII). 4-Hydroxy-3-methoxybenzoylacetic acid methyl ester (VI) and 3-hydroxy-(4-hydroxy-3-methoxyphenyl)-propanoic acid methyl ester (V) were synthesised and then identified as metabolites in the culture medium. The fungal degradation of the phenyl propenoic side chain of ferulic acid (I), a principal key step of lignin decomposition, appeared to proceed analogous to fatty acids.
Krings
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Institut für Lebensmittelchemie, Zentrum Angewandte Chemie der Universität, Wunstorfer Str. 14, D 30453 Hannover, Germany
Pilawa
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Theobald
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Berger
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RG
D001487:Basidiomycota / Q000378:metabolism*; D001547:Benzaldehydes / Q000378:metabolism; D019149:Bioreactors; D001709:Biotechnology; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000737:chemistry / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry
D001547:Benzaldehydes; D003373:Coumaric Acids; C004999:ferulic acid; C100058:vanillin