Fungicidal Activity of 3'-Substituted-3-Stilbenols

Holzforschung ◽  
2001 ◽  
Vol 55 (6) ◽  
pp. 568-572 ◽  
Author(s):  
T.H. Fisher ◽  
Y. Jin ◽  
T.P. Schultz
Keyword(s):  
Fungicidal Activity ◽  
Agar Plate ◽  
Brown Rot ◽  
Quantitative Structure Activity Relationship ◽  
White Rot ◽  
White Rot Fungus ◽  
Cinnamic Acids ◽  
Postia Placenta ◽  
Brown Rot Fungi ◽  
Structure Activity

Summary Twenty 3′-substituted-3-stilbenols were synthesized and tested for fungicidal activity (agar plate IC50 values) against two brown-rot fungi rot Gloeophyllum trabeum and Postia placenta and one white-rot fungus Trametes versicolor. Compounds synthesized were eight trans-3-X-3′-stilbenols (X = OMe, Me, Cl, OH, OPr, OBu, OOct, and O-p-Tol), three cis-3-X-3′-stilbenols (X = OMe, Me, Cl), three 3-hydroxy-α-(3-X-phenyl)cinnamic acids (X = OMe, Me, Cl), and six multisubstituted-3′-substituted-3-stilbenols (3′,4-diOMe, 3′-Me-4-OMe, 3′-Cl-4-OMe, 3′-OH-4-OMe, 3′-Cl-4-OMe-4′-OH, and 3′-Cl-4′-OH). The three cinnamic acids and 3′-OOct showed low to no activity against all three fungi. Most of these 3′-substituted-3-stilbenols (15 of 20) had fungicidal activity against the white-rot fungus T. versicolor, in contrast to earlier studies on 3′-substituted-4-stilbenols which were inactive against T. versicolor. These 3′-substituted-3-stilbenols also had fungicidal activity against G. trabeum and P. placenta, with the latter fungus having a parabolic lipophilic Quantitative Structure Activity Relationship (QSAR). 3′-O-p-Tol-3-stilbenol was the most active against T. versicolor and fifth most active against P. placenta of the twenty 3′-substituted-3-stilbenols examined here.

Iron and calcium translocation from pure gypsum and iron-amended gypsum by two brown rot fungi and a white rot fungus

Holzforschung ◽  
2008 ◽  
Vol 62 (6) ◽  
Author(s):  
Jonathan S. Schilling ◽  
Kaitlyn M. Bissonnette
Keyword(s):  
Building Materials ◽  
Woody Debris ◽  
White Rot Fungi ◽  
Brown Rot ◽  
White Rot ◽  
White Rot Fungus ◽  
Irpex Lacteus ◽  
Brown Rot Fungi ◽  
Ca Oxalate ◽  
Iron And Calcium

AbstractWood-degrading fungi commonly grow in contact with calcium (Ca)-containing building materials and may import Ca and iron (Fe) from soil into forest woody debris. For brown rot fungi, imported Ca2+may neutralize oxalate, while Fe3+may facilitate Fenton-based degradation mechanisms. We previously demonstrated, in two independent trials, that degradation of spruce by wood-degrading fungi was not promoted when Ca or Fe were imported from gypsum or metallic Fe, respectively. Here, we tested pine wood with lower endogenous Ca than the spruce blocks used in prior experiments, and included a pure gypsum treatment and one amended with 1% with FeSO4. Electron microscopy with microanalysis verified that brown rot fungiSerpula himantioidesandGloeophyllum trabeumand the white rot fungusIrpex lacteusgrew on gypsum and produced iron-free Ca-oxalate crystals away from the gypsum surface. Wood cation analysis verified significant Fe import by both brown rot isolates in Fe-containing treatments. Wood degradation was highest in Fe-gypsum-containing treatments for all three fungi, although only wood degraded byI. lacteushad significant Ca import. We suggest that Fe impurities may not exacerbate brown rot, and that both brown and white rot fungi may utilize Ca-containing materials.

scholarly journals Enhanced Lignocellulolytic Enzyme Activities on Hardwood and Softwood during Interspecific Interactions of White- and Brown-Rot Fungi

2021 ◽  
Vol 7 (4) ◽  
pp. 265
Author(s):  
Junko Sugano ◽  
Ndegwa Maina ◽  
Janne Wallenius ◽  
Kristiina Hildén
Keyword(s):  
Enzyme Activities ◽  
Interspecific Interactions ◽  
Wood Decay ◽  
Brown Rot ◽  
Species Interaction ◽  
Fungal Species ◽  
White Rot ◽  
White Rot Fungus ◽  
Wood Decomposition ◽  
Brown Rot Fungi

Wood decomposition is a sophisticated process where various biocatalysts act simultaneously and synergistically on biopolymers to efficiently break down plant cell walls. In nature, this process depends on the activities of the wood-inhabiting fungal communities that co-exist and interact during wood decay. Wood-decaying fungal species have traditionally been classified as white-rot and brown-rot fungi, which differ in their decay mechanism and enzyme repertoire. To mimic the species interaction during wood decomposition, we have cultivated the white-rot fungus, Bjerkandera adusta, and two brown-rot fungi, Gloeophyllum sepiarium and Antrodia sinuosa, in single and co-cultivations on softwood and hardwood. We compared their extracellular hydrolytic carbohydrate-active and oxidative lignin-degrading enzyme activities and production profiles. The interaction of white-rot and brown-rot species showed enhanced (hemi)cellulase activities on birch and spruce-supplemented cultivations. Based on the enzyme activity profiles, the combination of B. adusta and G. sepiarium facilitated birch wood degradation, whereas B. adusta and A. sinuosa is a promising combination for efficient degradation of spruce wood, showing synergy in β-glucosidase (BGL) and α-galactosidase (AGL) activity. Synergistic BGL and AGL activity was also detected on birch during the interaction of brown-rot species. Our findings indicate that fungal interaction on different woody substrates have an impact on both simultaneous and sequential biocatalytic activities.

Fungal biodegradation of genetically modified and lignin-altered quaking aspen (Populus tremuloides Michx.)

Holzforschung ◽  
2012 ◽  
Vol 66 (1) ◽  
Author(s):  
Richard Giles ◽  
Ilona Peszlen ◽  
Perry Peralta ◽  
Hou-Min Chang ◽  
Roberta Farrell ◽  
...  
Keyword(s):  
Populus Tremuloides ◽  
Lignin Content ◽  
Brown Rot ◽  
Decay Resistance ◽  
White Rot ◽  
White Rot Fungus ◽  
Quaking Aspen ◽  
Transgenic Trees ◽  
Postia Placenta ◽  
G Ratio

AbstractBetter access to wood carbohydrates as a result of reduced, or altered, lignin is a goal of biopulping, as well as biofuel research. In the present article, woods from three transgenic trees and one wild-type quaking aspen (Populus tremuloidesMichx.) were analyzed in terms of mass loss of cellulose and lignin after incubation with lignocellulolytic fungi. The transgenic trees had reduced lignin content through transfer of an antisense -4CL gene, elevated syringyl/guaiacyl (S/G) ratio through insertion of a sense CAld5H gene and low lignin content and elevated S/G ratio through simultaneous insertion of -4CL and CAld5H genes, respectively. The lignocellulolytic fungi employed were a lignin-selective white rot fungusCeriporiopsis subvermispora, a simultaneous white rot fungusTrametes versicolorand a brown rot fungusPostia placenta. Reduced lignin degradation was observed in woods with increased S/G ratios indicating that this analytical feature influences decay resistance, regardless of the fungal decay mechanism.

Decay resistance of wood treated with amino-silicone compounds

Holzforschung ◽  
2008 ◽  
Vol 62 (1) ◽  
pp. 112-118 ◽  
Author(s):  
Oliver Weigenand ◽  
Miha Humar ◽  
Geoffrey Daniel ◽  
Holger Militz ◽  
Carsten Mai
Keyword(s):  
Beech Wood ◽  
White Rot Fungi ◽  
Brown Rot ◽  
Decay Resistance ◽  
Solute Concentration ◽  
White Rot ◽  
White Rot Fungus ◽  
European Standard ◽  
Brown Rot Fungi ◽  
Amino Silicone

AbstractAn amino-silicone (AS; amino-polydimethylsiloxane) micro-emulsion was tested for its suitability to preserve wood against basidiomycetes in a mini-block experiment and in a test according to the European standard (1996) EN 113. Decay resistance was assessed against the white rot fungiTrametes versicolor,Ceriporiopsis subvermispora, andHypoxylon fragiforme, as well as the brown rot fungiConiophora puteana,Antrodia vaillantii,Gloeophyllum trabeumandSerpula lacrymans. Pine sapwood and beech wood were treated with AS emulsions at solute concentration levels of 2%, 5% and 15%. The mini-blocks treated with 15% concentrations of AS resisted decay byT. versicolorandC. puteanaover a long time (12 weeks), while samples treated with low and moderate concentrations underwent considerable mass losses. Accordingly, microscopic studies revealed a high degree of colonisation by the white rot fungus and loss of cell wall integrity (brown rot) in samples treated with 2% AS. At high AS content (15%), no or only initial stages of decay could be observed. In the European standard (1996) test EN 113, the mass loss in all fungal cultures except for the white rot ascomyceteH. fragiformewas below 5%, when the samples were treated with 15% AS. The effect of low and moderate AS concentration on the decay resistance was dependent on the fungal strain. The mode of action of AS treatment against basidiomycete decay is discussed.

Condensed conifer tannins as antifungal agents in liquid culture

Holzforschung ◽  
2013 ◽  
Vol 67 (7) ◽  
pp. 825-832 ◽  
Author(s):  
Anna-Kaisa Anttila ◽  
Anna Maria Pirttilä ◽  
Hely Häggman ◽  
Anni Harju ◽  
Martti Venäläinen ◽  
...  
Keyword(s):  
Growth Inhibition ◽  
Fungal Growth ◽  
White Rot Fungi ◽  
Brown Rot ◽  
Wood Preservative ◽  
Soft Rot ◽  
White Rot ◽  
Wood Preservatives ◽  
Active Components ◽  
Brown Rot Fungi

Abstract In the last decades, many wood preservatives have been prohibited for their ecotoxicity. The present article is focusing on the conifer-derived condensed tannins as environment-friendly options for the substitution of artificial wood preservatives. Eight different tannin fractions were extracted from spruce cones, spruce barks, and pine cones. The parameters of tannin extraction, such as the methods of purification and concentration of active components in the extracts, have been investigated. The cone and bark extracts were tested for the growth inhibition of eight brown-rot fungi, three white-rot fungi, and four soft-rot fungi in liquid cultures. The cone tannins provided a more efficient fungal growth inhibition than bark tannins. Purification increased the antifungal properties of the extracts. The growth of brown-rot fungi was inhibited by the tannins already at low concentrations. However, the extracts were not effective against the white-rot or soft-rot fungi. More investigation is needed concerning the tannin source and the purification procedure of the extracts before tannins can be considered as an ecologically benign wood preservative.

scholarly journals The Impact of Paraffin-Thermal Modification of Beech Wood on Its Biological, Physical and Mechanical Properties

Forests ◽  
2019 ◽  
Vol 10 (12) ◽  
pp. 1102 ◽  
Author(s):  
Ladislav Reinprecht ◽  
Miroslav Repák
Keyword(s):  
Mechanical Properties ◽  
Bending Strength ◽  
Beech Wood ◽  
Physical And Mechanical Properties ◽  
Brown Rot ◽  
European Beech ◽  
White Rot ◽  
White Rot Fungus ◽  
Poria Placenta ◽  
The Impact

The European beech (Fagus sylvatica L.) wood was thermally modified in the presence of paraffin at the temperatures of 190 or 210 °C for 1, 2, 3 or 4 h. A significant increase in its resistance to the brown-rot fungus Poria placenta (by 71.4%–98.4%) and the white-rot fungus Trametes versicolor (by 50.1%–99.5%) was observed as a result of all modification modes. However, an increase in the resistance of beech wood surfaces to the mold Aspergillus niger was achieved only under more severe modification regimes taking 4 h at 190 or 210 °C. Water resistance of paraffin-thermally modified beech wood improved—soaking reduced by 30.2%–35.8% and volume swelling by 26.8%–62.9% after 336 h of exposure in water. On the contrary, its mechanical properties worsened—impact bending strength decreased by 17.8%–48.3% and Brinell hardness by 2.4%–63.9%.

Thermal Stability and Decay Resistance Properties of Tropical Wood Polymer Nanocomposites (WPNC)

2013 ◽  
Vol 667 ◽  
pp. 482-489 ◽  
Author(s):  
Md. Saiful Islam ◽  
Sinin Hamdan ◽  
Mohamad Rusop ◽  
Md. Rezaur Rahman
Keyword(s):  
Thermal Stability ◽  
Polymer Nanocomposites ◽  
Phenol Formaldehyde ◽  
Brown Rot ◽  
Decay Resistance ◽  
White Rot ◽  
Postia Placenta ◽  
Tropical Wood ◽  
Wood Polymer ◽  
The Fourier Transform

The effects of nanoclay on the thermal stability and decay resistance properties of tropical wood polymer nanocomposites (WPNCs) were investigated in this work. WPNC were prepared from several selected tropical wood species by impregnating the selected woods with a combination of nanoclay and phenol formaldehyde (PF) prepolymer mixture. The formation of WPNC was confirmed by the fourier transform infrared spectroscopy (FTIR) analysis. Thermal property of manufactured WPNC in terms of thermogravimetric analysis (TGA) was evaluated, and an improvement in thermal stability was found for fabricated WPNC. The wood was then exposed to two types of fungi; white-rot (polyporous versicolor) and brown-rot (postia placenta), for 12 weeks. Decay was assessed through percentage (%) of weight loss. A significant improvement was found in the treated woods compared to the untreated ones. In addition, the fabricated WPNC showed lower moisture content compared with raw one.

Variation in germination percentage of basidiospores collected successively from wood decay fungi in culture

1983 ◽  
Vol 61 (1) ◽  
pp. 171-173 ◽  
Author(s):  
E. L. Schmidt ◽  
D. W. French
Keyword(s):  
Spore Germination ◽  
White Rot Fungi ◽  
Wood Decay ◽  
Brown Rot ◽  
Germination Percentage ◽  
White Rot ◽  
Malt Extract ◽  
Decay Fungi ◽  
Brown Rot Fungi ◽  
Wood Decay Fungi

Successive collections of basidiospores, produced in culture from the same hymenial areas of four species of wood decay fungi, were tested for spore germination percentage on malt extract agar under controlled conditions. Spores from white rot fungi retained high germination levels after 5 weeks of spore production, but germination averages for brown rot fungi decreased by more than 50%. Such variation should be considered in wood pathology research using spore germination bioassay.

scholarly journals Localizing gene regulation reveals a staggered wood decay mechanism for the brown rot fungusPostia placenta

2016 ◽  
Vol 113 (39) ◽  
pp. 10968-10973 ◽  
Author(s):  
Jiwei Zhang ◽  
Gerald N. Presley ◽  
Kenneth E. Hammel ◽  
Jae-San Ryu ◽  
Jon R. Menke ◽  
...  
Keyword(s):  
Cell Walls ◽  
Plant Biomass ◽  
Wood Decay ◽  
Brown Rot ◽  
Glycoside Hydrolases ◽  
Ros Generation ◽  
Rna Seq ◽  
Postia Placenta ◽  
Brown Rot Fungi ◽  
Whole Transcriptome

Wood-degrading brown rot fungi are essential recyclers of plant biomass in forest ecosystems. Their efficient cellulolytic systems, which have potential biotechnological applications, apparently depend on a combination of two mechanisms: lignocellulose oxidation (LOX) by reactive oxygen species (ROS) and polysaccharide hydrolysis by a limited set of glycoside hydrolases (GHs). Given that ROS are strongly oxidizing and nonselective, these two steps are likely segregated. A common hypothesis has been that brown rot fungi use a concentration gradient of chelated metal ions to confine ROS generation inside wood cell walls before enzymes can infiltrate. We examined an alternative: that LOX components involved in ROS production are differentially expressed by brown rot fungi ahead of GH components. We used spatial mapping to resolve a temporal sequence inPostia placenta, sectioning thin wood wafers colonized directionally. Among sections, we measured gene expression by whole-transcriptome shotgun sequencing (RNA-seq) and assayed relevant enzyme activities. We found a marked pattern of LOX up-regulation in a narrow (5-mm, 48-h) zone at the hyphal front, which included many genes likely involved in ROS generation. Up-regulation of GH5 endoglucanases and many other GHs clearly occurred later, behind the hyphal front, with the notable exceptions of two likely expansins and a GH28 pectinase. Our results support a staggered mechanism for brown rot that is controlled by differential expression rather than microenvironmental gradients. This mechanism likely results in an oxidative pretreatment of lignocellulose, possibly facilitated by expansin- and pectinase-assisted cell wall swelling, before cellulases and hemicellulases are deployed for polysaccharide depolymerization.

Efficacy of Pinosylvins against White-Rot and Brown-Rot Fungi

Holzforschung ◽  
1999 ◽  
Vol 53 (5) ◽  
pp. 491-497 ◽  
Author(s):  
Catherine C. Celimene ◽  
Jessie A. Micales ◽  
Leslie Ferge ◽  
Raymond A. Young
Keyword(s):  
Picea Glauca ◽  
Pinus Banksiana ◽  
White Rot Fungi ◽  
Brown Rot ◽  
Monomethyl Ether ◽  
Decay Resistance ◽  
White Rot ◽  
Red Maple ◽  
Brown Rot Fungi ◽  
Agar Media

Summary Three stilbenes, pinosylvin (PS), pinosylvin monomethyl ether (PSM) and pinosylvin dimethyl ether (PSD), were extracted from white spruce (Picea glauca), jack pine (Pinus banksiana), and red pine (Pinus resinosa) pine cones, and their structures were confirmed by spectroscopic and chromatographic (HPLC, GC/MS, NMR and FTIR) analysis. PS, PSM, PSD or a 1:1:1 mixture of these stilbenes at concentrations of 0.1 % and 1.0 % were examined for their fungal inhibitory activity by two bioassay methods. Growth of white-rot fungi (Trametes versicolor and Phanerochaete chrysosporium), and brown-rot fungi (Neolentinus lepideus, Gloeophyllum trabeum and Postia placenta) on agar media in the presence of each of the stilbenes or a 1:1:1 mixture inhibited growth of white-rot fungi, but slightly stimulated growth of brown-rot fungi. Soil-block assays, conditions more representative of those found in nature, did not correlate with those from the screening on agar media. PS, PSM, PSD or a 1:1:1 mixture of the three compounds at concentrations of 0.1 % and 1.0 % did not impart any significant decay resistance to white-rot fungi inoculated on a hardwood (Red maple). However under the same conditions, decay resistance was observed against brown-rot fungi on a softwood (Southern yellow pine). It appears that stilbenes at least partially contribute to wood decay resistance against brown-rot fungi.

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