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  • Phanerochaete chrysosporium  (3)
  • Dibenzylbutyrolactone lignan  (1)
  • Lignin biodegradation  (1)
  • 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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  • 3
    Electronic Resource
    Electronic Resource
    Direct cleavage of the vicinal diol linkage of the lignin model compound dihydroanisoin by the basidiomycete Phanerochaete chrysosporium (1983)
    Springer
    Archives of microbiology 134 (1983), S. 299-302 
    Details
    ISSN: 1432-072X
    Keywords: Phanerochaete chrysosporium ; Vicinal diol cleavage ; Lignin model compounds ; Dihydroanisoin ; Anlsyl alcohol ; White rot basidiomycete ; Anisaldehyde ; Cytochrome P-450 ; Activated oxygen
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The white rot basidiomycete Phanerochaete chrysosporium metabolized dihydroanisoin (1,2-dianisylethane-1,2 diol) in low nitrogen stationary cultures, conditions under which the ligninolytic system is expressed. Anisyl alcohol was isolated as a metabolic product indicating an initial diol bond cleavage of the substrate. Use of 3H-labeled dihydroanisoin (1,2-dianisylethane-1,2-diol-1,2 3H) indicated that the diol bond was cleaved directly, yielding anisyl aldehyde as the initial product. The metabolically stable ketol anisoin was shown not be an intermediate in the metabolism of dihydroanisoin. The diol cleavage reaction was dependent on the concentration of molecular oxygen but O2 could be replaced by H2O2 under some conditions. The cleavage reaction was inhibited by exogenously-added tyrosine2-Cu2+ complex (TCC). The appearance of the fungal diol cleavage system parallels the appearance of the ligninolytic system under a variety of physiological conditions. In addition, preincubation of ligninolytic cultures with 2.5 mM l-glutamate represses both the ligninolytic and the diol cleavage activities.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00407806
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  • 4
    Electronic Resource
    Electronic Resource
    Enantiomeric compositions and biosynthesis ofWikstroemia sikokiana lignans (2000)
    Springer
    Journal of wood science 46 (2000), S. 234-242 
    Details
    ISSN: 1611-4663
    Keywords: Wikstroemia sikokiana ; Stereochemistry of biosynthesis ; Lariciresinol ; Secoisolariciresinol ; Dibenzylbutyrolactone lignan
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
    Notes: Abstract Thymelaeaceae plants produce dextrorotatory dibenzylbutyrolactone lignans, which are opposite enantiomers to the lignans isolated from other plants (e.g.,Forsythia spp.). In our previous paper, (−)-pinoresinol (74% enantiomer excess), (+)-matairesinol (optically pure), and (+)-wikstromol (optically pure) were isolated fromWikstroemia sikokiana (Thymelaeaceae). In the present investigation, a survey of lignans and the determination of their enantiomeric compositions were continued. Four lignans, (−)-lariciresinol, (−)-secoisolariciresinol, (+)-kusunokinin, and (+)-methyltrachelogenin, were isolated from MeOH extracts ofW. sikokiana stem. To our knowledge, we have isolated (+)-methyltrachelogenin from plants for the first time. Chiral high-performance liquid chromatographic analysis showed that (+)-kusunokinin and (+)-methyltrachelogenin were optically pure, whereas (−)-lariciresinol and (−)-secoisolariciresinol were not (39% and 45% enantiomer excess, respectively). Feeding experiments with deuterium-labeled substrates demonstrated conversion of coniferyl alcohol to the lignans and interconversion of lignans. These reaction sequences are similar to the sequence catalyzed byForsythia enzymes. However, predominant enantiomers of the lignans, except for secoisolariciresinol isolated fromW. sikokiana, have absolute configurations opposite to those of the corresponding lignans isolated fromForsythia spp. Based on the results of the isolation and the feeding experiments, several differences betweenW. sikokiana andForsythia spp. are pointed out regarding stereochemical mechanisms for lignan biosynthesis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00776455
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