scholarly journals Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Holzforschung ◽  
2005 ◽  
Vol 59 (6) ◽  
pp. 620-627 ◽  
Author(s):  
Chi-Lin Wu ◽  
Shih-Chang Chien ◽  
Sheng-Yang Wang ◽  
Yueh-Hsiung Kuo ◽  
Shang-Tzen Chang

Abstract Cadinane-type sesquiterpenes have a wide spectrum of biological activity, but their use as wood preservatives and the structure-activity relationships of their derivatives have not yet been reported. A total of 13 compounds were synthesized from T-cadinol, T-muurolol, and α-cadinol and their chemical structures were confirmed by IR, MS, and 1H and 13C NMR. The antifungal properties of 16 compounds against three wood-decay fungi were evaluated in vitro. α-Cadinol showed strong antifungal activity against Lenzites betulina, Trametes versicolor, and Laetiporus sulphureus (total mean IC50 0.10 mM). Among the derivatives synthesized, 3β-ethoxy-T-muurolol (0.24 mM), 4ξH-cadinan-10β-ol (0.25 mM), 4ξH-muurolan-10β-ol (0.29 mM), and 4ξH-cadinan-10α-ol (0.25 mM) showed good antifungal activity against all fungi tested. Correlation was observed between the antifungal activity of the compounds tested and log P. Furthermore, the presence of an unsaturated double bond and oxygen-containing functional groups in the compounds plays a key role in their antifungal activity. The stereo configuration of cadinane-type sesquiterpenes also influences their antifungal activity. Understanding how the structure of natural compounds relates to their antifungal function is important and may facilitate their application as novel wood preservatives.

1985 ◽  
Vol 63 (2) ◽  
pp. 337-339 ◽  
Author(s):  
Elmer L. Schmidt

Influences of eight saturated aliphatic acids (C5–C10, C12, and C16) on basidiospores of four isolates of wood-decay fungi (Poria tenuis and Trametes hispida, white rot fungi, and two isolates of the brown rot fungus Gloeophyllum trabeum) were observed in vitro. Spore responses after 24 h on malt extract agar containing 10, 102 or 103 ppm of each acid included normal germination, delay of germ tube emergence, vacuolation and degeneration of spore cytoplasm, and prevention of germ tube development without spore destruction. Acids of chain length C5–C10 prevented spore germination and killed spores of all fungi at concentrations of 20–50 ppm in media, whereas other acids tested were less active. Spore germination assay of decay fungi may prove useful as a screening tool to compare potency of wood preservatives.


2012 ◽  
Vol 518-523 ◽  
pp. 29-33 ◽  
Author(s):  
Peng Fei Xiao ◽  
Toshio Mori ◽  
Ryuichiro Kondo

Although heptachlor epoxide is one of the most persistent organic pollutants (POPs) that cause serious environmental problems, there is very limited information of the biodegradation of heptachlor epoxide by microorganisms, and no systematic study on the metabolic products and pathway of endrin by microorganisms has been conducted. Wood-decay fungi can degrade a wide spectrum of recalcitrant organopollutants, including polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated biphenyls (PCBs). In this study, 18 wood-decay fungi strains of genus Phlebia were investigated for their ability to degrade heptachlor epoxide, and Phlebia acanthocystis, Phlebia brevispora, Phlebia lindtneri and Phlebia aurea removed about 16, 16, 22 and 25% of heptachlor epoxide, respectively, after 14 days of incubation. Heptachlor diol and 1-hydroxy-2,3-epoxychlordene were detected in these fungal cultures as metabolites by gas chromatography and mass spectrometry (GC/MS), suggesting that the hydrolysis reaction in the epoxide ring and substitution of chlorine atom with hydroxyl group in C1 position occur in bioconversion of heptachlor epoxide by selected wood-decay fungi, respectively. This is the first report describing the metabolites of heptachlor epoxide by microorganisms.


2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Yu-Chang Su ◽  
Kuan-Ping Hsu ◽  
Eugene I-Chen Wang ◽  
Chen-Lung Ho

In this study, anti-mildew and anti-wood-decay fungal activities of the leaf and fruits essential oil and its constituents from Juniperus formosana were evaluated in vitro against seven mildew fungi and four wood decay fungi, respectively. The main compounds responsible for the anti-mildew and anti-wood-decay fungal activities were also identified. The essential oil from the fresh leaves and fruits of J. formosana were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS, respectively. The leaf oil mainly consisted of α-pinene (41.0%), limonene (11.5%), α-cadinol (11.0%), elemol (6.3%), and β-myrcene (5.8%); the fruit oil was mostly α-pinene (40.9%), β-myrcene (32.4%), α-thujene (5.9%) and limonene (5.9%). Comparing the anti-mildew and anti-wood-decay fungal activities of the oils suggested that the leaf oil was the most effective. For the anti-mildew and anti-wood-decay fungal activities of the leaf oil, the active source compounds were determined to be α-cadinol and elemol.


2011 ◽  
Vol 65 (1) ◽  
pp. 108-115 ◽  
Author(s):  
M. Schubert ◽  
T. Volkmer ◽  
C. Lehringer ◽  
F.W.M.R. Schwarze

2005 ◽  
Vol 58 (12) ◽  
pp. 901 ◽  
Author(s):  
Jenny M. Carr ◽  
Peter J. Duggan ◽  
David G. Humphrey ◽  
James A. Platts ◽  
Edward M. Tyndall

As part of a larger project aimed at the development of leach resistant boron-based wood preservatives, the anti-fungal and termiticidal activities, and the resistance to leaching from timber, of three related tetra-n-butylammonium spiroborates, tetra-n-butylammonium bis(ortho-hydroxymethylphenolato)borate 2, tetra-n-butylammonium bis[catecholato(2–)-O,O′]borate 3, and tetra-n-butylammonium bis[salicylato(2−)-O,O']borate 4, have been examined. All three borates are found to be active against test organisms, with the following orders of activity being observed: 2 > 3 > 4 > boric acid against wood decay fungi, and 2 > 3 ≈ 4 > boric acid against termites. The most active compound in both assays 2 also has the highest calculated lipophilicity. In a test for permanence in wood, the following order of leach resistance is observed: 4 >> 3 ≈ 2 > boric acid. This order appears to correlate more closely with the stability constants of the borate esters, as determined using 11B NMR spectroscopy, rather than calculated lipophilicities.


2019 ◽  
Vol 7 (3) ◽  
Author(s):  
Ferry Vernando Hutabarat ◽  
Farah Diba ◽  
Lolyta Sisillia

The aim of the research was to examine the antifungal activity and the most effective concentration of teak bark (Tectona grandis Linn F) extract in inhibiting wood decay fungi Schizophyllum commune Fries. Teak bark was derived from BKPH Ledok, Sambong district, Blora Regency, West Java. The Teak bark made into particle with size pass of 40 mesh and retained 60 mesh. Then one kilogram of teak bark particle was maceration with 10 liter of aquadest. The extract then mixes with potatoes dextrose agar (PDA) with several concentration i.e. 0%, 0.25%, 0.5%, 0.75% and 1% and pour into petri dish. One isolate of Schizophyllum commune was put in the center of PDA in each petri dish then incubated for nine days. The bioactive compound of extract teak bark was evaluation used phytochemical screening. Result of the research showed that teak bark extract at concentration 0.25% and 0.5% has antifungal activity values was 27.98% and 40.38% and categorized as medium inhibition growth of S. commune. Meanwhile at concentration 0.75% and 1% the AFA values was 59.94% and 65.51% categorized as strong inhibition growth of S. commune. The bioactive compounds from phytochemical screening test were alkaloid, flavonoid, terpenoid, fenolik, antrakuinon, and saponin. The extract of teak bark with concentration 0.75% and 1% are the most effective concentrations in inhibiting the growth of wood decay fungi S. commune Fries.Keywords : antifungal, phytochemical screening test, Schizophyllum commune, Tectona grandis


HortScience ◽  
2010 ◽  
Vol 45 (3) ◽  
pp. 401-408 ◽  
Author(s):  
Manuela Baietto ◽  
A. Dan Wilson

The development of wood decay caused by 12 major root-rot and trunk-rot fungi was investigated in vitro with sapwood extracted from nine ornamental and landscape hardwood and conifer species native to southern temperate regions of North America, Europe, and the lower Mississippi Delta. Wood decay rates based on dry weight loss for 108 host tree–wood decay fungi combinations were compared at 21 °C over 1-year and 2-year incubation periods in the absence of tree-resistance mechanisms. Strains of Armillaria mellea, Ganoderma lucidum, and Heterobasidion annosum exhibited the highest decay potential in most tree species tested. The order of fungi causing the greatest decay varied over time as a result of temporal changes in decay-rate curves. Relative wood durability or resistance to decay generally was greater in gymnosperm than in angiosperm wood types. Quercus nuttallii, Fraxinus pennsylvanica, and Quercus lyrata sustained the highest levels of decay by all fungi. Northern white cedar (Thuja occidentalis) sapwood was most resistant to decay by all rot-fungi tested, sustaining only limited weight loss after 1 and 2 years of decay, although sapwood of Pinus taeda, Liquidambar styraciflua, and Platanus occidentalis had relatively low levels of decay after 2 years. These results in combination with data from portable decay-detection devices provide useful information for the management of tree breakages or failures resulting from wood decay fungi in hazardous landscape trees. Some potential landscaping applications for tree evaluations, risk assessments, and selections for tree-replacement plantings are discussed.


2018 ◽  
Vol 94 (02) ◽  
pp. 109-116 ◽  
Author(s):  
Marta Aleksandrowicz-Trzcińska ◽  
Adam Szaniawski ◽  
Jacek Olchowik ◽  
Stanisław Drozdowski

2019 ◽  
Vol 22 (4) ◽  
pp. 1104-1114 ◽  
Author(s):  
Salma Moutaouafiq ◽  
Abdellah Farah ◽  
Yassine Ez zoubi ◽  
Mohamed Ghanmi ◽  
Badr satrani ◽  
...  

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