Metabolism of the lignin model compounds veratrylglycerol-?-guaiacyl ether and 4-ethoxy-3-methoxyphenylglycerol-?-guaiacyl ether by Phanerochaete chrysosporium

Enoki, Akio; Goldsby, Gwendolyn P.; Gold, Michael H.

doi:10.1007/bf00446881

Cited by 62 publications

(26 citation statements)

References 16 publications

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“…Hence, incorporation of 18 0 into the benzyl position of (VII I) suggests the participation of another pathway, in which (V) is not involved, to yield (VIII). In conclusion, we propose the following ·two alternative pathways for the degradation of the [3-0-4 substructure based on the degradation products identified and isotopic experiments: (a) pathways via (V) (arylglycerol), (a-I) hydrolysis to give (V) and (VIII') or (a-2) initial attack of the vanillin portion in (IV') to result in (V); (b) direct oxygenative Ca-C p cleavage of the [3-0-4 substructure to give (VI), (VII) and (VIII), which is completely different from the mechanism reported by Enoki et al 17 ): Initial Cy-oxidation and subsequent non-oxygenative retro-aldol condensation type cleavage of the Ca-C p linkage. In the pathway (b), 18 0 2 was incorporated into the C a position, while it was presumed that 18 0 2 was not incorporated into the C a position on Ca-C p cleavage ofa [3-1 type lignin model dimer by P. chrysosporium.…”

Section: Incorporation Ofcontrasting

confidence: 51%

Deradation Pathway of Arylglycerol-β-aryl Ethers byPhanerochaete chrysosporium

Umezawa

Nakatsubo

Higuchi

1983

Agricultural and Biological Chemistry

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Section: Incorporation Ofcontrasting

confidence: 51%

Deradation Pathway of Arylglycerol-β-aryl Ethers byPhanerochaete chrysosporium

Umezawa

Nakatsubo

Higuchi

1983

Agricultural and Biological Chemistry

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“…In intact cultures of Phanerochaete chrysosporium C,-Cp cleavage is the major reaction (Enoki et al 1980(Enoki et al , 1981Higuchi et al 1983;Fenn and Kirk 1984). Quantitatively, degradation of the model compound I was fairly similar in both P. ehrysosporium and Phlebia radiata.…”

Section: Discussionmentioning

confidence: 95%

“…Thus, r-O-4 models are the most important types of compounds used in lignin biodegradation studies (Kirk et al 1986b;Buswell and Odier 1987;Kirk and Farrell 1987). The results suggest that ligninolytic cultures of the white-rot fungus Phanerochaete chrysosporium can oxidize fl-aryl ether dimers by several different pathways (Enoki et al 1980(Enoki et al , 1981Higuchi et al 1983;Fenn and Kirk 1984;Kirk et al 1986b;Miki et al 1986;Kirk and Farrell 1987). P. chrysosporiurn produces lignin peroxidases (ligninases) (Glenn et al 1983;Kirk 1983, 1984;) and manganese-dependent peroxidases (Mnperoxidases) Paszczynski et al 1985) but it is considered an atypical white-rot fungus as it does not produce laccase (EC 1.10.3.2).…”

Section: Introductionmentioning

confidence: 97%

Metabolism of non-phenolic ?-O-4 lignin model compounds by the white-rot fungus Phlebia radiata

Hatakka

Lundell

Tervilä-Wilo

et al. 1991

Appl Microbiol Biotechnol

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The degradation of three non-phenolic fl-Oo 4 diarylpropane lignin model compounds was studied in cultures of the white-rot fungus Phlebia radiata. The degradation pattern of the model compound 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-l,3-diol (I) was also compared with that of Phanerochaete chrysosporium under conditions where both fungi were cultivated without agitation in an oxygen atmosphere. Compound I was readily degraded by both fungi, and qualitatively the degradation patterns were quite similar. The product, after Ca-C a bond cleavage, was veratraldehyde (IV) which was almost stoichiometrically reduced to veratryi alcohol (V). However, large amounts of V were detected only in P. chrysosporiurn cultures. Experiments with the model compound 1-(4-ethoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-l,3-diol (II) showed that in the presence of II, the total amount of veratryl compounds accounted for [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33].LM in standing cultures of Phlebia radiata. The model compound 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenoxy) propane-l,3-diol (III) was more readily degraded than I and II. The results indicated that, in P. radiata cultures, the acting enzymes were lignin peroxidases and IV reducing enzyme, while laccase was less important.

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“…Studies have employed dimeric and polymeric model compounds of lignin (Enoki et al, 1980;Enoki & Gold, 1982;Kirk et al, 1983;Nakatsubo et al, 198 1 ;Kawai et al, 1985 ;Hammel et al, 1986), and [ 4C]lignin lignocellulose substrates. The natural substrates have been prepared from cereal grasses (e.g.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 14C-radiolabelled lignocelluloses from spring barley of differing maturities and their solubilization by Phanerochaete chrysosporium and Streptomyces cyaneus

Mason

Birch

Broda

1990

Journal of General Microbiology

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[U-14C]Phenylalanine was injected into spring barley plants during 140 d growth. Autoradiography of the plants revealed that, apart from high concentrations around the injection sites, radioactivity was evenly distributed throughout the plants.[14C]Lignin lignocellulose was prepared from plants cropped at 30,58,82 and 140 d after sowing, using organic and aqueous solvents followed by enzymic hydrolysis with commercial protease and polysaccharidase preparations. Weight loss due to solvent and enzymic treatments was greatest in the youngest plants, resulting in a preparation of [14C]lignocellulose of specific activity 2-8-fold higher than preparations from more mature plants. When subjected to crude preparations of extracellular protein from either Phunerochuete chrysosprium or Streptomyces cyuneus the substrate derived from the youngest plants (30 d) was particularly susceptible to solubilization of lignocellulose by polysaccharidases. Substrates prepared from plants after 58 d growth (i.e. fully grown) showed significant levels of lignocellulose solubilization that were not due to the action of polysaccharidases. When used in similar assays the oldest crops (82 and l a d ) were solubilized at very low levels. The desirability of using fully grown plants as substrates in lignin solubilization and biodegradation studies is clearly demonstrated.

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Metabolism of the lignin model compounds veratrylglycerol-?-guaiacyl ether and 4-ethoxy-3-methoxyphenylglycerol-?-guaiacyl ether by Phanerochaete chrysosporium

Cited by 62 publications

References 16 publications

Deradation Pathway of Arylglycerol-β-aryl Ethers byPhanerochaete chrysosporium

Deradation Pathway of Arylglycerol-β-aryl Ethers byPhanerochaete chrysosporium

Metabolism of non-phenolic ?-O-4 lignin model compounds by the white-rot fungus Phlebia radiata

Preparation of 14C-radiolabelled lignocelluloses from spring barley of differing maturities and their solubilization by Phanerochaete chrysosporium and Streptomyces cyaneus

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