Effect of the antifungal activity of oxygenated aromatic essential oil compounds on the white-rot Trametes versicolor and the brown-rot Coniophora puteana

A series of novel benzofuran-1,3,4-oxadiazole hybrids were synthesized and evaluated as antifungal agents. The synthetic pathway was started from salicylaldehyde, which afforded 5-(substituted benzylthio)-1,3,4-oxadiazole derivatives in moderate to good yields. The compounds were investigated for their antifungal potential against white-rot, Trametes versicolor and brown-rot, Poria placenta and Coniophora puteana fungi at different concentrations (500, 1000 ppm). The obtaining results demonstrated that most of the compounds at 500 ppm concentration did not exhibit acceptable antifungal effects but they had better antifungal activity at 1000 ppm concentration. Compounds 5a, 5c, and 5i showed inhibition percentages of 14.6%, 23.0%, and 14.7%, against the growth of P. placenta and C. puteana, respectively. Among the compounds, the 2-(benzofuran-2-yl)-5-((2,6-difluorobenzyl)thio)-1,3,4-oxadiazole (5h) hybrid was the most active one.

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Design and synthesis of new benzofuran-1,2,3-triazole hybrid preservatives and the evaluation of their antifungal potential against white and brown-rot fungi

BioResources ◽

10.15376/biores.15.4.7828-7843 ◽

2020 ◽

Vol 15 (4) ◽

pp. 7828-7843

Author(s):

Fahimeh Abedinifar ◽

S. Morteza F. Farnia ◽

Seyyed Khalil Hosseinihashemi ◽

Abbas Jalaligoldeh ◽

Shahrbanoo Arabahmadi ◽

...

Keyword(s):

Trametes Versicolor ◽

Brown Rot ◽

White Rot ◽

Gloeophyllum Trabeum ◽

Coniophora Puteana ◽

Brown Rot Fungi ◽

Design And Synthesis ◽

Poria Placenta ◽

Antifungal Potential ◽

Antifungal Effects

A series of novel benzofuran-1,2,3-triazole hybrids were synthesized and investigated as fungicidal preservatives. The compounds were evaluated for their antifungal potential against white-rot (Trametes versicolor), dry brown-rot (Poria placenta), and wet brown-rot (Coniophora puteana and Gloeophyllum trabeum) fungi, at different concentrations (500 ppm and 1000 ppm). The tests of the final products (8a, 8b, 8c, 8d, 8e, 8f, and 8g) demonstrated that compound N-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzofuran-2-carboxamide (8f) at a concentration of 500 ppm was the most active against wet brown-rot C. puteana (23.86% inhibition) and G. trabeum (47.16% inhibition) fungi. However, testing demonstrated that compounds 8a, 8b, 8c, 8d, and 8g at a concentration of 500 ppm did not exhibit acceptable antifungal effects against white-rot T. versicolor and dry brown-rot P. placenta fungi.

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Composition and antifungal activity of balsam from Liquidambar formosana Hance

Holzforschung ◽

10.1515/hf-2012-0086 ◽

2013 ◽

Vol 67 (3) ◽

pp. 345-351 ◽

Cited By ~ 8

Author(s):

Shih-Chang Chien ◽

Jun-Hong Xiao ◽

Yen-Hsueh Tseng ◽

Yueh-Hsiung Kuo ◽

Sheng-Yang Wang

Keyword(s):

Antifungal Activity ◽

Volatile Compounds ◽

Tree Species ◽

Brown Rot ◽

Betulonic Acid ◽

White Rot ◽

Spectroscopic Techniques ◽

Laetiporus Sulphureus ◽

Lenzites Betulina

Abstract Formosan sweet gum (Liquidambar formosana Hance) is a tree species endemic in Taiwan. In this study, the composition of balsam from L. formosana has been determined by several chromatographic and spectroscopic techniques. Among the 26 compounds identified, three new triterpenoids were detected, namely, 2α,3α-dihydroxyolean-12-en-28-al (1), 3α-hydroxyolean-12-en-30-ol (2), and 3α-hydroxyolean-2-oxo-12-en-28-al (3). The most abundant volatile compounds were β-caryophyllene (22.7%), α-pinene (23.3%), and β-pinene (19.6%), and the most abundant nonvolatile compounds were 3α,25-dihydroxyolean-12-en-28-oic acid (12, 19.1%), oleanonic aldehyde (9, 14.0%), and betulonic acid (15, 13.4%). The compounds 3α,25-dihydroxyolean-12-en-28-oic acid and bornyl cinnamate were found to be inhibitory for white rot (Lenzites betulina) and brown rot (Laetiporus sulphureus) fungi.

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PROPRIEDADES BIOLÓGICAS DE PAINÉIS DE CASCA DE ARROZ E ADESIVO TANINO-FORMALDEÍDO

Nativa ◽

10.31413/nativa.v6i5.5566 ◽

2018 ◽

Vol 6 (5) ◽

pp. 532 ◽

Cited By ~ 1

Author(s):

Joel Telles de Souza ◽

Clóvis Roberto Haselein ◽

Walmir Marques de Menezes ◽

Alencar Garlet ◽

Maiara Talgatti

Keyword(s):

Rice Husk ◽

Trametes Versicolor ◽

Oryza Sativa L ◽

Pearson Correlation ◽

Brown Rot ◽

Biological Properties ◽

White Rot ◽

Gloeophyllum Trabeum ◽

Natural Form ◽

Decay Fungi

O presente estudo tem como objetivo avaliar as propriedades biológicas, por meio de ensaio de apodrecimento acelerado com fungos xilófagos, em chapas aglomeradas de casca de arroz (Oryza sativa L) coladas com adesivo à base de tanino-formaldeído. Para tanto, foram utilizadas casca de arroz na forma natural e processada em moinho de martelo, compactadas a diferentes massas específicas (0,65; 0,95 e 1,15 g.cm-³) e aplicando-se teores de adesivos de 7, 10 e 13%, totalizando 54 chapas. Os resultados de perda de massa foram submetidos ao teste de correlação simples de Pearson e analisados por regressão. De acordo com os requisitos da norma ASTM D-2017 (2005), os testes biológicos, para todos os tratamentos, foram classificados como resistentes ao fungo Trametes versicolor, podridão branca. Já para o fungo Gloeophyllum trabeum a maioria dos tratamentos foram classificados como moderadamente resistente. Portanto, a casca de arroz mostra-se como uma alternativa de elevado potencial para a manufatura de chapas de maior resistência aos fungos apodrecedores de madeiras.Palavras-chave: massa específica, correlação simples de Pearson, fungos apodrecedores. BIOLOGICAL PROPERTIES OF RICE HUSK PARTICLEBOARD MANUFACTURED WITH TANNIN-FORMALDEHYDE ABSTRACT:Resistance to decay fungi Trametes versicolor and Gloephyllum trabeum of panels produced with rice husk and tannin - formaldehyde adhesive was evaluated. In the production of the panels, rice hulls were used in its natural form or hammer milled, compacted at different densities (0.65, 0.95 and 1.15 g/cm³) and with adhesives levels of 7, 10 and 13 % (based on the ovendry weight of the particles. The results were submitted to the Pearson correlation test and analyzed by regression. According to the requirements of ASTM D- 2017 (2005), the biological tests for all treatments were classified as resistant to white rot ungus Trametes versicolor. For the brown rot fungus Gloeophyllum trabeum, most treatments were classified as moderately resistant. Therefore, rice husk can be a high potential alternative to for the manufacture of particleboards for greater resistance to decay wood fungi.Keywords: specific gravity, simple Pearson correlation, decay fungi.

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Chemical structure and antifungal activity of mint essential oil components

Journal of the Serbian Chemical Society ◽

10.2298/jsc191210017p ◽

2020 ◽

Vol 85 (9) ◽

pp. 1149-1161

Author(s):

Dragana Plavsic ◽

Marija Skrinjar ◽

Djordje Psodorov ◽

Lato Pezo ◽

Ivan Milovanovic ◽

...

Keyword(s):

Antifungal Activity ◽

Essential Oil ◽

Chemical Structure ◽

Coefficient Of Determination ◽

Mentha Piperita ◽

Training Cycle ◽

Ms Analysis ◽

Structure Retention ◽

Quantitative Structure Retention Relationship ◽

Essential Oil Compounds

The objective of this research was to determine chemical composition and to evaluate the antifungal activity of essential oil of Mentha piperita. By the application of GC/MS analysis of essential mint oil, 27 components were identified. The major components were menthol (39.9 %), menton (23.51 %), menthyl acetate (7.29 %), 1.8-cineol (5.96 %), isomenton (5.24 %), isomenthol (3.17 %), trans-caryophyllene (2.88 %), limonene (2.14 %), pulegon (1.38 %), beta-pinene (1.14 %) and piperiton (1.03 %). The quantitative structure? retention relationship (QSRR) was employed to predict the retention time (RT) of Mentha piperita essential oil compounds obtained in GC/MS analysis, using twelve molecular descriptors selected by genetic algorithm. The selected descriptors were used, as inputs of an artificial neural network, to build an RT predictive QSRR model. The coefficient of determination was 0.983, during training cycle, indicating that this model could be used for prediction of RT values for essential oil compounds in Mentha piperita essential oil extracts. Essential oil of Mentha piperita showed antifungal activity on all tested isolates in the minimal inhibitory concentration range of 0.2?1.7 ?l/ml and a minimal fungicidal concentration (MFC) range of 1.7?454.5 ?l/ml. The most powerful antifungal activity of mint was observed in C. cladosporioides of MFC value 1.7 ?l/ml. P. aurantiogriseum showed the lowest sensitivity of MFC value 454.5 ?l/ml.

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Mechanical Properties and Decay Resistance ofcmd="newline"Hornbeam Cement Bonded Particleboards

Research Letters in Materials Science ◽

10.1155/2008/379749 ◽

2008 ◽

Vol 2008 ◽

pp. 1-4 ◽

Cited By ~ 2

Author(s):

Antonios N. Papadopoulos

Keyword(s):

Mechanical Properties ◽

Trametes Versicolor ◽

White Rot Fungi ◽

Decay Resistance ◽

White Rot ◽

Carpinus Betulus ◽

Cement Ratio ◽

Coniophora Puteana ◽

Wood Particles ◽

Minimum Requirements

Cement bonded particleboards were manufactured from hornbeam (Carpinus betulusL.) wood particles. Hydration tests were carried out to determine the inhibitory index in order to characterise wood-cement compatibility. The results revealed that the mixture of hornbeam-cement can be classified as moderate inhibition. Two wood: cement ratios were applied in this study, namely, 1 : 3 and 1 : 4, for the board manufacture. It was found that an increase of cement-wood ratio resulted in an improvement in all properties examined, except MOR. All properties of the boards made from 1 : 4 wood: cement ratio surpassed the minimum requirements set forth by the building type HZ code. Boards were exposed to brown and white rot fungi,Coniophora puteana, andTrametes versicolor, respectively. Overall, both fungi failed to attack the cement-bonded boards.

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Proteomics Reveals Octyl Gallate as an Environmentally Friendly Wood Preservative Leading to Reactive Oxygen Species-Driven Metabolic Inflexibility and Growth Inhibition in White-Rot Fungi (Lenzites betulina and Trametes versicolor)

Journal of Fungi ◽

10.3390/jof7020145 ◽

2021 ◽

Vol 7 (2) ◽

pp. 145

Author(s):

Jin-Wei Xu ◽

Chen-Chung Liao ◽

Ke-Chang Hung ◽

Zhong-Yao Wang ◽

Yu-Tang Tung ◽

...

Keyword(s):

Reactive Oxygen Species ◽

Antifungal Activity ◽

Trametes Versicolor ◽

Reactive Oxygen ◽

White Rot Fungi ◽

Environmentally Friendly ◽

White Rot ◽

Oxygen Species ◽

Wood Preservatives ◽

Lenzites Betulina

The most commonly applied wood preservatives are based on creosote, pentachlorophenol, and waterborne chromate copper arsenate, which negatively affect the environment. Thus, environmentally friendly wood preservatives are required. This study investigated the antifungal activity and mechanism of several long-chain alkyl gallates (3,4,5-trihydroxybenzoates) against white-rot fungi, Lenzites betulina and Trametes versicolor. The results revealed that octyl gallate (OG) had the best antifungal activity. Additionally, OG may have a mechanism of action similar to surfactants and inhibit ATPase activity, causing mitochondrial dysfunction and endogenous reactive oxygen species (ROS) production. Upon exposure to endogenous ROS, cells rapidly inhibit the synthesis of 60S ribosomal subunits, thus reducing the mycelial growth rate. L. betulina and T. versicolor also remodeled their energy metabolism in response to low ATP levels and endogenous ROS. After OG treatment, ATP citrate synthase activity was downregulated and glycolytic activity was upregulated in L. betulina. However, the activity of aerobic pathways was decreased and the oxidative branch of the pentose phosphate pathway was redirected form nicotinamide adenine dinucleotide phosphate (NADPH) to minimize endogenous ROS-mediated damage in T. versicolor. Taken together, these observations reveal that OG is a potent inhibitor of white-rot fungus. Further structural optimization research and pharmacological investigations are warranted.

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Antifungal activity of polycyclic aromatic hydrocarbons against Ligninolytic fungi

Hemijska industrija ◽

10.2298/hemind110408039m ◽

2011 ◽

Vol 65 (5) ◽

pp. 575-581 ◽

Cited By ~ 2

Author(s):

Mustafa Memic ◽

Alisa Selovic ◽

Jasmina Sulejmanovic

Keyword(s):

Polycyclic Aromatic Hydrocarbons ◽

Antifungal Activity ◽

Aromatic Hydrocarbons ◽

Fossil Fuels ◽

Brown Rot ◽

White Rot ◽

Wood Preservation ◽

Diffusion Method ◽

Ligninolytic Fungi ◽

Polycyclic Aromatic

Environmental contamination by polycyclic aromatic hydrocarbons (PAHs) has caused increasing concern because of their known, or suspected, carcinogenic and mutagenic effects. Polycyclic aromatic hydrocarbons occurring in the environment are usually the result of the incomplete combustion of carbon containing materials. The main sources of severe PAHs contamination in soil come from fossil fuels, i.e. production or use of fossil fuels or their products, such as coal tar and creosote. Creosote is used as a wood preservation for railway ties, bridge timbers, pilling and large-sized lumber. It consists mainly of PAHs, phenol and cresol compounds that cause harmful health effects. Research on biodegradation has shown that a special group of microorganisms, the white-rot fungi and brown-rot fungi, has a remarkable potential to degrade PAHs. This paper presents a study of the antifungal activity of 12 selected PAHs against two ligninolytic fungi Hypoxylon fragiforme (white rot) and Coniophora puteana (brown rot). The antifungal activity of PAHs was determined by the disc-diffusion method by measuring the diameter of the zone of inhibition. The results showed that the antifungal activity of the tested PAHs (concentration of 2.5 mmol/L) depends on the their properties such as molar mass, solubility in water, values of log Kow, ionization potential and Henry?s Law constant as well as number of aromatic rings, molecule topology or pattern of ring linkage. Among the 12 investigated PAHs, benzo(k) fluoranthene with five rings, and pyrene with four cyclic condensed benzene rings showed the highest antifungal activity.

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Chemical composition and antifungal activity of essential oil isolated from Chamaecyparis formosensis Matsum. wood

Holzforschung ◽

10.1515/hf.2005.049 ◽

2005 ◽

Vol 59 (3) ◽

pp. 295-299 ◽

Cited By ~ 37

Author(s):

Sheng-Yang Wang ◽

Chi-Lin Wu ◽

Fang-Hua Chu ◽

Shih-Chang Chien ◽

Yueh-Hsiung Kuo ◽

...

Keyword(s):

Chemical Composition ◽

Antifungal Activity ◽

Essential Oil ◽

Trametes Versicolor ◽

Wood Decay ◽

Retention Indices ◽

Decay Fungi ◽

Wood Decay Fungi ◽

Chamaecyparis Formosensis ◽

Reference Samples

Abstract The chemical composition of the essential oil of Chamaecyparis formosensis wood has been examined. GC-MS data and retention indices for reference samples were used to identify 32 constituents. α-Eudesmol (18.06%), β-guaiene (8.0%), (–)-β-cadinene (7.89%), γ-costal (7.03%), α-muurolol (6.49%), 4α-hydroxy-4β-methyldihydrocostol (5.52%), σ-selinene (4.78%), santolina triene (4.60%), eremophilene (4.32%), humulene (4.11%), myrtenol (4.11%), and τ-cadinene (3.25%) were the most abundant components. Tests with the typical wood decay fungi, Laetiporus sulphureus and Trametes versicolor, proved the antifungal activity of the oil, as the growth of L. sulphureus and T. versicolor was inhibited at concentrations of 50 and 100 μg ml−1, respectively. The following characteristic volatile compounds were isolated and purified from ethyl acetate fractions: epi-cubenol, chamaecynone, myrtenol, cis-myrtanol, 12-hydroxyisointermedenol and 4α-hydroxy-4β-methyldi-hydrocostol. Chamaecynone possessed the strongest antifungal activity, with an antifungal index of 88.2% and 67.3% for L. sulphureus and T. versicolor at a dose of 50 μg ml−1, respectively.

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