Production of small molecular weight catalysts and the mechanism of trinitrotoluene degradation by several Gloeophyllum species

Newcombe, David; Paszczyński, Andrzej; Gajewska, Wioletta; Kröger, Mario; Feis, Gregor; Crawford, Ronald L.

doi:10.1016/s0141-0229(02)00014-5

Cited by 36 publications

(29 citation statements)

References 35 publications

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“…1). They propose that DMHQ is the extracellular reductant of Fe 3ϩ in S. lacrymans, basing their hypothesis on previous evidence that DMHQ drives Fenton chemistry by reducing Fe 3ϩ and O 2 in members of another brown rot lineage, the Gloeophyllales, when they are grown in liquid media (9)(10)(11)(12). Morerecent work conducted with biodegrading wood supports a physiological role for DMHQ in brown rot of natural substrates within the Gloeophyllales (18), and also the Polyporales (13).…”

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confidence: 86%

“…However, it is generally agreed that biodegradative hydroxyl radicals produced via extracellular Fenton chemistry (H 2 O 2 ϩ Fe 2ϩ ϩ H ϩ ¡ H 2 O ϩ Fe 3ϩ ϩ · OH) are important oxidants in incipient brown rot (5)(6)(7)(8). The requisite Fe 2ϩ and H 2 O 2 are produced in part by secreted fungal hydroquinones or catechols, and by more-reactive semiquinone radicals derived from them, which together drive one-electron reductions of Fe 3ϩ and O 2 in the wood (9)(10)(11)(12). In some cases, this chemistry is apparently also promoted by fungal laccases that oxidize hydroquinones or catechols to generate semiquinones (13).…”

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confidence: 99%

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Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Korripally

Timokhin

Houtman

et al. 2013

Appl Environ Microbiol

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dBasidiomycetes that cause brown rot of wood are essential biomass recyclers in coniferous forest ecosystems and a major cause of failure in wooden structures. Recent work indicates that distinct lineages of brown rot fungi have arisen independently from ligninolytic white rot ancestors via loss of lignocellulolytic enzymes. Brown rot thus proceeds without significant lignin removal, apparently beginning instead with oxidative attack on wood polymers by Fenton reagent produced when fungal hydroquinones or catechols reduce Fe 3؉ in colonized wood. Since there is little evidence that white rot fungi produce these metabolites, one question is the extent to which independent lineages of brown rot fungi may have evolved different Fe 3؉ reductants. Recently, the catechol variegatic acid was proposed to drive Fenton chemistry in Serpula lacrymans, a brown rot member of the Boletales (D. C. Eastwood et al., Science 333:762-765, 2011). We found no variegatic acid in wood undergoing decay by S. lacrymans. We found also that variegatic acid failed to reduce in vitro the Fe 3؉ oxalate chelates that predominate in brown-rotting wood and that it did not drive Fenton chemistry in vitro under physiological conditions. Instead, the decaying wood contained physiologically significant levels of 2,5-dimethoxyhydroquinone, a reductant with a demonstrated biodegradative role when wood is attacked by certain brown rot fungi in two other divergent lineages, the Gloeophyllales and Polyporales. Our results suggest that the pathway for 2,5-dimethoxyhydroquinone biosynthesis may have been present in ancestral white rot basidiomycetes but do not rule out the possibility that it appeared multiple times via convergent evolution.

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confidence: 86%

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confidence: 99%

Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Korripally

Timokhin

Houtman

et al. 2013

Appl Environ Microbiol

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“…88,89 Estudos mais recentes com fungos de decomposição parda crescidos em meio líquido definido demonstram que estes fungos usam radicais hidroxila para iniciar a degradação de vários polímeros sintéticos e organopoluentes. [90][91][92][93][94] O radical hidroxila pode abstrair hidrogênio de subunidades de açúcar de polissacarídeos como a celulose, com elevada constante de velocidade (~ 10 9 M -1 s -1…”

Section: áCido Oxálicounclassified

Relevância de compostos de baixa massa molar produzidos por fungos e envolvidos na biodegradação da madeira

Arantes¹,

Milagres²

2009

Quím. Nova

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Recebido em 16/7/08; aceito em 27/1/09; publicado na web em 3/7/09 RELEVANCE OF LOW MOLECULAR WEIGHT COMPOUNDS PRODUCED BY FUNGI AND INVOLVED IN WOOD BIODEGRADATION. Over the last decade, evidences have been shown that the wood biodegradation by fungi is not only a result of the action of their enzymatic machinery but also of various low molecular weight non-enzymatic compounds, especially in fungi that promote brown and white decay, which in nature are the major wood decaying microorganisms. The present review focuses on the recent theories involving these low molecular weight compounds that act direct or synergistically with lignocellulolytic enzymes to attack the wood main macromolecular constituents, their relevance as potential degradative systems, in the overall wood biodegradation, and also outlines their potential biotechnological applications.Keywords: wood biodegradation; enzymes; low molecular weight compounds.A biodegradação de materiais lignocelulósicos, como a madeira, é um processo natural de reciclagem de matéria orgânica e o entendimento deste processo contribui com a compreensão do ciclo natural do carbono, que tem início na biossíntese dos seus constituintes a partir de H 2 O, CO 2 e energia solar e termina com a mineralização destes constituintes e liberação de CO 2 e H 2 O, em decorrência da decomposição causada principalmente por fungos.Por muito tempo o processo de biodegradação foi foco de muitos estudos devido à grande quantidade de madeira e produtos à base de madeira, que são danificados por ação de fungos, e devido à necessidade do desenvolvimento de métodos de prevenção à biodegradação menos ofensivos ao meio ambiente. Atualmente, os fungos degradadores de madeira e/ou seus sistemas degradativos têm sido intensivamente estudados em razão do elevado potencial de utilização em aplicações biotecnológicas, como na biodegradação de compostos xenobióticos, 1-3 biorremediação de solos, 1,4,5 biopolpação da madeira 6,7 e biobranqueamento de polpas celulósicas. [8][9][10] Uma vez que o desenvolvimento e a eficácia destes métodos/processos dependem principalmente do conhecimento dos mecanismos químicos e bioquímicos envolvidos na biodegradação dos constituintes da madeira, o entendimento destes mecanismos certamente irá contribuir para o desenvolvimento de novas aplicações, assim como para a melhoria das já existentes.Apesar do considerável conhecimento adquirido nas últimas dé-cadas a respeito da enzimologia da biodegradação dos constituintes da madeira, até os dias de hoje não se conhecem os mecanismos químicos e bioquímicos exatos empregados pelos fungos durante este processo. Contudo, sabe-se que o processo de biodegradação da madeira por fungos não pode ser explicado unicamente com base na ação das diversas enzimas lignocelulolíticas por eles secretadas. Dentro dessa abordagem, pesquisas recentes têm indicado uma participação expressiva de compostos de baixa massa molar (CBMM). 11,12Neste sentido, esta revisão tem como objetivo principal agrupar as diferentes teorias envolvendo CBMM produ...

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“…For production of H 2 O 2 and regeneration of Fe 2ϩ , G. trabeum is reported as using extracellular phenolate biochelators (19,32,58). Of these biochelators, 2,5-dimethoxyhydroquinone and 4,5-dimethoxycatechol were identified and proposed to play a key role in providing the Fenton reactants via a hydroquinone-quinone redox cycle (30,32,41,45,50) driven by an intracellular low-specificity NADH quinone reductase (5,31). H 2 O 2 is formed nonenzymatically by dismutation of intermediate ·OOH/O 2 · Ϫ oxyradicals produced by reduction of O 2 by semiquinones or when either of these radicals are reduced by Fe 2ϩ (24).…”

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confidence: 99%

Characteristics of Gloeophyllum trabeum Alcohol Oxidase, an Extracellular Source of H ₂ O ₂ in Brown Rot Decay of Wood

Daniel

Volc

Filonova

et al. 2007

Appl Environ Microbiol

117

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A novel alcohol oxidase (AOX) has been purified from mycelial pellets of the wood-degrading basidiomycete Gloeophyllum trabeum and characterized as a homooctameric nonglycosylated protein with native and subunit molecular masses of 628 and 72.4 kDa, containing noncovalently bonded flavin adenine dinucleotide. The isolated AOX cDNA contained an open reading frame of 1,953 bp translating into a polypeptide of 651 amino acids displaying 51 to 53% identity with other published fungal AOX amino acid sequences. The enzyme catalyzed the oxidation of short-chain primary aliphatic alcohols with a preference for methanol (K m ‫؍‬ 2.3 mM, k cat ‫؍‬ 15.6 s ؊1 ). Using polyclonal antibodies and immunofluorescence staining, AOX was localized on liquid culture hyphae and extracellular slime in sections from degraded wood and on cotton fibers. Transmission electron microscopy immunogold labeling localized the enzyme in the hyphal periplasmic space and wall and on extracellular tripartite membranes and slime, while there was no labeling of hyphal peroxisomes. AOX was further shown to be associated with membranous or slime structures secreted by hyphae in wood fiber lumina and within the secondary cell walls of degraded wood fibers. The differences in AOX targeting compared to the known yeast peroxisomal localization were traced to a unique C-terminal sequence of the G. trabeum oxidase, which is apparently responsible for the protein's different translocation. The extracellular distribution and the enzyme's abundance and preference for methanol, potentially available from the demethylation of lignin, all point to a possible role for AOX as a major source of H 2 O 2 , a component of Fenton's reagent implicated in the generally accepted mechanisms for brown rot through the production of highly destructive hydroxyl radicals.

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Production of small molecular weight catalysts and the mechanism of trinitrotoluene degradation by several Gloeophyllum species

Cited by 36 publications

References 35 publications

Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Relevância de compostos de baixa massa molar produzidos por fungos e envolvidos na biodegradação da madeira

Characteristics of Gloeophyllum trabeum Alcohol Oxidase, an Extracellular Source of H ₂ O ₂ in Brown Rot Decay of Wood

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Production of small molecular weight catalysts and the mechanism of trinitrotoluene degradation by several Gloeophyllum species

Cited by 36 publications

References 35 publications

Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Evidence from Serpula lacrymans that 2,5-Dimethoxyhydroquinone Is a Lignocellulolytic Agent of Divergent Brown Rot Basidiomycetes

Relevância de compostos de baixa massa molar produzidos por fungos e envolvidos na biodegradação da madeira

Characteristics of Gloeophyllum trabeum Alcohol Oxidase, an Extracellular Source of H 2 O 2 in Brown Rot Decay of Wood

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Characteristics of Gloeophyllum trabeum Alcohol Oxidase, an Extracellular Source of H ₂ O ₂ in Brown Rot Decay of Wood