Biodegradation of aromatic compounds by white rot and ectomycorrhizal fungal species and the accumulation of chlorinated benzoic acid in ectomycorrhizal pine seedlings

ABSTRACT Aryl metabolite biosynthesis was studied in the white rot fungusBjerkandera adusta cultivated in a liquid medium supplemented with l-phenylalanine. Aromatic compounds were analyzed by gas chromatography-mass spectrometry following addition of labelled precursors (14C- and 13C-labelledl-phenylalanine), which did not interfere with fungal metabolism. The major aromatic compounds identified were benzyl alcohol, benzaldehyde (bitter almond aroma), and benzoic acid. Hydroxy- and methoxybenzylic compounds (alcohols, aldehydes, and acids) were also found in fungal cultures. Intracellular enzymatic activities (phenylalanine ammonia lyase, aryl-alcohol oxidase, aryl-alcohol dehydrogenase, aryl-aldehyde dehydrogenase, lignin peroxidase) and extracellular enzymatic activities (aryl-alcohol oxidase, lignin peroxidase), as well as aromatic compounds, were detected in B. adusta cultures. Metabolite formation required de novo protein biosynthesis. Our results show that l-phenylalanine was deaminated to trans-cinnamic acid by a phenylalanine ammonia lyase and trans-cinnamic acid was in turn converted to aromatic acids (phenylpyruvic, phenylacetic, mandelic, and benzoylformic acids); benzaldehyde was a metabolic intermediate. These acids were transformed into benzaldehyde, benzyl alcohol, and benzoic acid. Our findings support the hypothesis that all of these compounds are intermediates in the biosynthetic pathway froml-phenylalanine to aryl metabolites. Additionally,trans-cinnamic acid can also be transformed via β-oxidation to benzoic acid. This was confirmed by the presence of acetophenone as a β-oxidation degradation intermediate. To our knowledge, this is the first time that a β-oxidation sequence leading to benzoic acid synthesis has been found in a white rot fungus. A novel metabolic scheme for biosynthesis of aryl metabolites froml-phenylalanine is proposed.

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ChemInform Abstract: FACILE SYNTHESIS OF ETHYNYLATED BENZOIC ACID DERIVATIVES AND AROMATIC COMPOUNDS VIA ETHYNYLTRIMETHYLSILANE

Chemischer Informationsdienst ◽

10.1002/chin.198142137 ◽

1981 ◽

Vol 12 (42) ◽

Author(s):

W. B. AUSTIN ◽

N. BILOW ◽

W. J. KELLEGHAN ◽

K. S. Y. LAU

Keyword(s):

Benzoic Acid ◽

Aromatic Compounds ◽

Facile Synthesis ◽

Benzoic Acid Derivatives

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Effect of aromatic compounds on growth and ligninolytic enzyme production of two white rot fungi Ceriporiopsis subvermispora and Cyathus stercoreus

Canadian Journal of Microbiology ◽

10.1139/cjm-44-9-872 ◽

1998 ◽

Vol 44 (9) ◽

pp. 872-885 ◽

Cited By ~ 2

Author(s):

Anand Sethuraman ◽

Danny E. Akin ◽

Jason G. Eisele ◽

Karl-Erik L. Eriksson

Keyword(s):

Aromatic Compounds ◽

Enzyme Production ◽

White Rot Fungi ◽

Ligninolytic Enzyme ◽

White Rot ◽

Ceriporiopsis Subvermispora ◽

Cyathus Stercoreus

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Investigating the effects of symbiotic fungi on the flight behaviour ofSirex noctilio(Hymenoptera: Siricidae)

The Canadian Entomologist ◽

10.4039/tce.2016.10 ◽

2016 ◽

Vol 148 (5) ◽

pp. 543-551 ◽

Cited By ~ 5

Author(s):

Mark A. Sarvary ◽

Ann E. Hajek ◽

Katalin Böröczky ◽

Robert A. Raguso ◽

Miriam F. Cooperband

Keyword(s):

Fungal Species ◽

Flight Tunnel ◽

White Rot ◽

White Rot Fungus ◽

Sirex Noctilio ◽

Flight Behaviour ◽

Native North American ◽

Complete Chemical Analysis ◽

Volatile Profiles ◽

Symbiotic Fungi

AbstractThe invasive woodwaspSirex noctilioFabricius (Hymenoptera: Siricidae) is obligately associated with the symbiotic white rot fungusAmylostereum areolatum(Chaillet ex Fries) Boidin (Basidiomycota: Amylosteraceae), and shows positive chemotaxis to volatiles emitted by this symbiont. After introduction to North America,S. noctiliowas collected carrying another fungus speciesAmylostereum chailletii(Persoon) Boidin, used symbiotically by native North AmericanSirexLinnaeus. We conducted flight behaviour studies in a walk-in flight tunnel to evaluate specificity of the attraction of mated and unmatedS. noctilioto its primary symbiont,A. areolatum, versus the alternative symbiont,A. chailletii. Fewer unmated than matedS. noctiliofemales responded to either of the fungi. Unmated females showed no landing preference but matedS. noctiliofemales were attracted toA. areolatumalthough avoidance ofA. chailletiiwas not complete. Chemical analysis demonstrated major differences in the volatile profiles of the two fungal species. Sesquiterpenes dominated theA. areolatumsamples, whereas only two aromatic volatiles were consistently present in the nativeA. chailletii.

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Genome Sequencing and Carbohydrate-Active Enzyme (CAZyme) Repertoire of the White Rot Fungus Flammulina elastica

International Journal of Molecular Sciences ◽

10.3390/ijms19082379 ◽

2018 ◽

Vol 19 (8) ◽

pp. 2379 ◽

Cited By ~ 12

Author(s):

Young-Jin Park ◽

Yong-Un Jeong ◽

Won-Sik Kong

Keyword(s):

Gene Prediction ◽

Gc Content ◽

Industrial Applications ◽

Fungal Species ◽

Amino Acid Sequences ◽

Glycoside Hydrolases ◽

White Rot ◽

White Rot Fungus ◽

Carbohydrate Binding ◽

Carbohydrate Binding Modules

Next-generation sequencing (NGS) of the Flammulina elastica (wood-rotting basidiomycete) genome was performed to identify carbohydrate-active enzymes (CAZymes). The resulting assembly (31 kmer) revealed a total length of 35,045,521 bp (49.7% GC content). Using the AUGUSTUS tool, 12,536 total gene structures were predicted by ab initio gene prediction. An analysis of orthologs revealed that 6806 groups contained at least one F. elastica protein. Among the 12,536 predicted genes, F. elastica contained 24 species-specific genes, of which 17 genes were paralogous. CAZymes are divided into five classes: glycoside hydrolases (GHs), carbohydrate esterases (CEs), polysaccharide lyases (PLs), glycosyltransferases (GTs), and auxiliary activities (AA). In the present study, annotation of the predicted amino acid sequences from F. elastica genes using the dbCAN CAZyme database revealed 508 CAZymes, including 82 AAs, 218 GHs, 89 GTs, 18 PLs, 59 CEs, and 42 carbohydrate binding modules in the F. elastica genome. Although the CAZyme repertoire of F. elastica was similar to those of other fungal species, the total number of GTs in F. elastica was larger than those of other basidiomycetes. This genome information elucidates newly identified wood-degrading machinery in F. elastica, offers opportunities to better understand this fungus, and presents possibilities for more detailed studies on lignocellulosic biomass degradation that may lead to future biotechnological and industrial applications.

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Decay resistance of softwoods and hardwoods thermally modified by the Thermovouto type thermo-vacuum process to brown rot and white rot fungi

Holzforschung ◽

10.1515/hf-2015-0244 ◽

2016 ◽

Vol 70 (9) ◽

pp. 877-884 ◽

Cited By ~ 18

Author(s):

Jie Gao ◽

Jong Sik Kim ◽

Nasko Terziev ◽

Geoffrey Daniel

Keyword(s):

White Rot Fungi ◽

Brown Rot ◽

Decay Resistance ◽

Fungal Species ◽

White Rot ◽

Agar Block ◽

Pycnoporus Sanguineus ◽

Postia Placenta ◽

Soil Block ◽

Class 1

Abstract Softwoods (SW, spruce and fir) and hardwoods (HW, ash and beech) were thermally modified by the thermo-vacuum (Termovuoto) process for 3–4 h in the temperature range 160–220°C (TMW160–220°C) and their fungal durability were examined in soil-block tests with two brown rot (BR, Postia placenta, Gloeophyllum trabeum) and two white rot (WR, Pycnoporus sanguineus, Phlebia radiata) fungi. SW-TMW160–220°C were exposed to P. placenta and P. sanguineus and HW-TMW190–220°C to all fungal species. Considerable improvement (durability class 1–3) in decay resistance was only achieved for SW- and HW-TMW220°C. Thermal modification (TM) below 200°C influenced decay resistance negatively in case of some fungal species applied for both SW and HW. Judged by the durability class, decay resistance was higher in HW- than in SW-TMW at high TM temperature. Behavior of TM differed significantly between ash (ring-porous HW) and beech (diffuse-porous HW). A comparison between results of soil- and agar-block tests on Termovouoto wood demonstrated that the influence of testing method in terms of assignment to durability classes is not significant.

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Cool flames in the combustion of toluene and ethylbenzene

Proceedings of the Royal Society of London Series A - Mathematical and Physical Sciences ◽

10.1098/rspa.1956.0210 ◽

1956 ◽

Vol 238 (1213) ◽

pp. 143-153 ◽

Cited By ~ 4

Keyword(s):

Hydrogen Peroxide ◽

Light Intensity ◽

Benzoic Acid ◽

Aromatic Compounds ◽

Flow System ◽

Reaction Vessel ◽

Static System ◽

Cool Flame ◽

Cool Flames ◽

Blue Flame

The oxidation of toluene and ethylbenzene has been studied in a static system using a spherical reaction vessel (700 ml.) over the temperature range 300 to 500°C, and at total pressures up to 600 mm. Cool flames were observed in the oxidation of both hydrocarbons, but only the reaction of ethylbenzene gave rise to a ‘blue’ flame at higher temperatures. With neither hydrocarbon did periodicity in light intensity, or pressure pulses, occur. The ignition diagrams for 4 to 1 fuel + oxygen mixtures have been mapped out. With ethylbenzene, the cool flame was maintained in a flow system, its spectrum was photographed and shown to be similar to that of fluorescent formaldehyde. The products of the reaction contained acetophenone, benzaldehyde and benzoic acid, phenol, quinol, hydrogen peroxide and methoxyhydroperoxide. The results have been compared with corresponding data for the oxidation of paraffin hydrocarbons, and it is concluded that, with both aromatic compounds, the processes allowing the possibility of cool-flame formation are themselves secondary in nature.

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Hydrogen Isotope Exchange in Aromatic Compounds in the Presence of Raney Nickel Alloy

Australian Journal of Chemistry ◽

10.1071/ch9790189 ◽

1979 ◽

Vol 32 (1) ◽

pp. 189 ◽

Cited By ~ 4

Author(s):

AC Finlayson ◽

RKMR Kallury ◽

RH Prager

Keyword(s):

Benzoic Acid ◽

Aqueous Solutions ◽

Nickel Alloy ◽

Raney Nickel ◽

Aromatic Compounds ◽

Anthranilic Acid ◽

Hydrogen Isotope ◽

Isotope Exchange ◽

Hydrogen Isotope Exchange ◽

Rapid Proton

Aromatics undergo rapid proton-deuterium or -tritium exchange in aqueous solutions containing Raney nickel alloy. The specificity of exchange in benzoic acid, anthranilic acid, pyridine and aniline is investigated by degradation and mass and N.M.R. spectrometry. Positions meta and para to carboxylate are most readily exchanged.

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Biological pretreatment of wheat straw: Effect of fungal culturing on enzymatic hydrolysis of carbohydrate polymers

10.21203/rs.3.rs-227697/v1 ◽

2021 ◽

Author(s):

Aleksandar Knežević ◽

Ivana Đokić ◽

Tomislav Tosti ◽

Slađana Popović ◽

Dušanka Milojković-Opsenica ◽

...

Keyword(s):

Enzymatic Hydrolysis ◽

Wheat Straw ◽

Lignin Degradation ◽

Enzymatic Saccharification ◽

White Rot Fungi ◽

Fungal Species ◽

White Rot ◽

Irpex Lacteus ◽

Fungal Pretreatment ◽

Hydrolysis Of

Abstract The aim of the study was comparative analysis of degradation of wheat straw lignin by white-rot fungi and its implications on the efficiency of enzymatic hydrolysis of holocellulose. Cyclocybe cylindracea, Ganoderma resinaceum, Irpex lacteus, Pleurotus ostreatus and Trametes versicolor were the species studied. Peroxidases were predominantly responsible for lignin degradation even though high laccase activities were detected, except in the case of Irpex lacteus where laccase activity was not detected. Studied fungal species showed various ability to degrade lignin in wheat straw which further affected release of reducing sugars during enzymatic saccharification. The highest rate of lignin degradation was noticed in sample pretreated with Irpex lacteus (50.9 ± 4.1%). Among all tested species only Ganoderma resinaceum was suitable lignin degrader with the 2-fold higher hydrolysis yield (51.1 ± 4.7%) than in the control, and could have significant biotechnological application due to lower cellulose loss. A key mechanism of carbohydrate component convertibility enhancement was lignin removal in the biomass. Long time consumption, the low sugar yields and unpredictable fungal response still remain the challenge of the fungal pretreatment process.

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