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  • 1
    Electronic Resource
    Electronic Resource
    Metabolism of a phenylcoumaran substructure lignin model compound in ligninolytic cultures of Phanerochaete chrysosporium (1981)
    Springer
    Archives of microbiology 128 (1981), S. 416-420 
    Details
    ISSN: 1432-072X
    Keywords: Lignin biodegradation ; White-rot fungi ; Fungus physiology ; Wood decay ; Aromatic metabolism ; Phanerochaete chrysosporium
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00405924
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  • 2
    Electronic Resource
    Electronic Resource
    A Phanerochaete chrysosporium mutant defective in lignin degradation as well as several other secondary metabolic functions (1982)
    Springer
    Archives of microbiology 132 (1982), S. 115-122 
    Details
    ISSN: 1432-072X
    Keywords: Phanerochaete chrysosporium ; Lignin degradation ; Veratryl alcohol ; Secondary metabolism ; Mutants ; Phenol oxidase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract A pleiotropic mutant of Phanerochaete chrysosporium 104-2 lacking phenol oxidase and unable to form fruit bodies and a revertant strain 424-2 were isolated after UV mutagenesis. Strains 104-2 and 424-2 had no apparent dysfunction in primary metabolism with glucose as a carbon source. Unlike the wild type strain and strain 424-2, strain 104-2 was unable to evolve 14CO2 from 14C ring, side chain and 3-O-14C-methoxy labeled lignin. In addition, strain 104-2 was unable to evolve 14CO2 from a variety of lignin model compounds including 14C-4′-methoxy labeled veratrylglycerol-β-guaiacyl (V) ether, γ-14C-guaiacylglycerol-β-guaiacyl ether (VI), as well as 1-(14C-4′-methoxy, 3′-methoxyphenyl)1,2 propene (III) and 1-(14C-4′-methoxy-3′-methoxyphenyl) 1,2 dihydroxypropane (IV). The addition of peroxidase/H2O2 to cultures of strain 104-2 did not alter its capacity to degrade the labeled lignins. A variety of unlabeled lignin model compounds previously shown to be degraded by the wild type organism including β-aryl ether dimers and diaryl propane dimers were also not degraded by the mutant 104-2. The revertant strain 424-2 regained the capacity to degrade these compounds. The substrates described are degraded by oxygen requiring system(s) expressed during the secondary phase of growth, suggesting this pleiotropic mutant is possibly defective in the onset of postprimary metabolism. The inability of the mutant to produce the secondary metabolite veratryl alcohol and to elaborate enzymes in the veratryl alcohol biosynthetic pathway supports this hypothesis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00508715
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Biosynthesis of the secondary metabolite veratryl alcohol in relation to lignin degradation in Phanerochaete chrysosporium (1981)
    Springer
    Archives of microbiology 129 (1981), S. 321-324 
    Details
    ISSN: 1432-072X
    Keywords: White-rot fungi ; Secondary metabolism ; Wood decay ; Mycelial pellets ; Fungus physiology ; l-Glutamic acid repression ; Phenylalanine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The lignin-degrading basidiomycete Phanerochaete chrysosporium synthesizes veratryl alcohol (3,4-dimethoxybenzyl alcohol) via phenylalanine, 3,4-dimethoxycinnamyl alcohol and veratrylglycerol. Study of the conversion of 3,4-dimethoxycinnamyl alcohol to veratrylglycerol and veratryl alcohol showed is to be (a) catalyzed by a secondary metabolic system, (b) markedly suppressed by culture agitation, and (c) strongly inhibited by l-glutamate. The amount of veratryl alcohol synthesized de novo was positively correlated with the O2 concentration after primary growth. Other work has shown that the cinnamyl alcohol terminal residue in a lignin substructure model compound is degraded via arylglycerol and benzyl alcohol structures in ligninolytic cultures of P. chrysosporium, and that the ligninolytic system exhibits traits (a)-(c) above. Ligninolytic activity is also strongly and positively correlated with O2 concentration. The results here suggest, therefore, that the actual biosynthetic secondary metabolic product is 3,4-dimethoxycinnamyl alcohol, but that this is degraded by the ligninolytic system to veratryl alcohol via veratrylglycerol. Veratryl alcohol is only slowly metabolized by the fungus, and accumulates.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00414706
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    Paper (German National Licenses)
    Fulltext
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