Fungus Phellinus Tremulae Research Articles

Phellintremulins A-C, antinociceptive sesquiterpenoids from the medicinal fungus Phellinus tremulae

Phellintremulin A (1), a rearranged sesquiterpenoid with an unprecedented bicyclic backbone, and two previously unreported illudane-type sesquiterpenoids, namely phellintremulin B (2) and phellintremulin C (3), together with two known analogues (±)‒4 and (±)‒5, were isolated from cultures of the medicinal fungus Phellinus tremulae. Their structures and absolute configurations were established by means of spectroscopic data and HRESIMS analyses, as well as ECD and NMR calculations. A plausible biogenesis for 1 was discussed. The electrophysiological experiments showed that phellintremulins (A‒C) can inhibit Nav current in DRG neuron cells at 10 μM, with percentage inhibitions of 23.2%, 49.3%, and 31.7%, respectively. The antinociceptive activities of phellintremulins (A‒C) were evaluated via the acetic acid-induced writhing test in mice at a dose of 3 mg/kg. They showed significant antinociceptive effects with percentages of inhibition of 43.8%, 54.4%, and 50.6%, respectively, and phellintremulin B and C expressed more potent analgesic effect than lidocaine.

Molecular Identification and Karyological Analysis of a Rampant Aspen Populus tremula L. (Salicaceae) Clone.

A rampant highly heterozygous aspen (Populus tremula L.) clone “Meshabash” has been revealed in course of population genetic diversity analysis in a native stand in the Republic of Tatarstan, Russia. Here we report the results of karyological analysis showing that this highly vigorous clone is diploid (2n = 38) while typically triploid aspen demonstrates increased growth rate and resistance to aspen trunk rot caused by fungus Phellinus tremulae. By means of DNA identification of a series of model trees using 14 SSR loci we outlined the area occupied by this clone (at least 1.94 ha) and demonstrated that its ramets constitute 40 out of 48 genotyped trunks on the plot with the maximal distance between ramets 254 m. Since aspen is able to regenerate after cutting or die-off of maternal tree by root suckers at a distance up to 20–35 m this assumed that current stand appeared as a result of such spreading from an ortet tree during at least 5 generations. Trunk rot damage in the wood of model trees indicated low influence of this pathogen on viability and performance of the studied clone that can be associated with its extreme heterozygosity level (0.926) exceeding all the studied trees in this research plot and in three other control samples.

Growth and breeding of aspen in Russia

Abstract Researches results are presented that describe variation in natural aspen stands and hybrid collections in Central European Russia. The subject of the study was the selection of the most productive and resistant to heart rot caused by fungus Phellinus tremulae (Fomes igniarius) stands. Mechanical wood properties, fodder values and other valuable characteristics of aspen are also shown. The valuable stands and hybrids which require conservation were selected for breeding and practical use.

The biosynthesis of the new tremulane sesquiterpenes isolated from Phellinustremulae

The tremulane sesquiterpenes isolated from the wood-rotting fungus Phellinustremulae are irregular isoprenoids derived from the cyclization and rearrangement of farnesyl pyrophosphate (FPP). The most interesting feature in the formation of the tremulane skeleton seems to involve the migration of a methyl group from one of the isoprene units. To investigate the biosynthetic origin of this unique sesquiterpene skeleton, labelling experiments were carried out by adding 13C-labelled sodium acetate to liquid cultures of Phellinustremulae. The labelling pattern was determined by 13C NMR spectral analysis of labelled tremulenediol A, which was purified as its di-p-bromobenzoate. A possible route to the tremulane skeleton, which accounts for the observed labelling pattern, proceeds from FPP, via humulene. The stereochemical course of the tremulane biosynthesis is discussed. Keywords: fungal metabolites, aspen, perhydroazulene sesquiterpenes, labelling experiments.

1994 E.W.R. Steacie Award Lecture Application of natural products chemistry to a biological problem

Aspen that bear a certain type of black gall have a lower incidence of heartwood rot (caused by the fungus Phellinustremulae) than do nearby non-gall trees. Efforts to determine the chemical nature of this black gall effect are described. The metabolites of some fungi associated with the black gall (Phomaetheridgei, Stachybotryscylindrospora), and of the rotting fungus Phellinustremulae, are described. Extracts of the black gall tissue have a very high concentration of benzoic acid and it is suggested that the benzoic acid may play a role in the protection of the galled trees. Keywords: fungal metabolites, aspen, benzoic acid, salicylic acid, black galls on aspen, Phellinustremulae.

Black stem galls on aspen: anatomy and histochemistry

Large black stem galls occur sporadically on trembling aspen (Populus tremuloides) in western Canada. Although little is known about their cause or structure, trees having these galls are less likely than surrounding aspen to have advanced decay caused by the fungus Phellinus tremulae. The anatomy and histochemistry of black galls and associated branch galls were studied and compared with normal wood and bark. Light microscopy showed that the cambium of black galls produces greater numbers of cells per growth ring and that growth rings are two to three times wider than normal. Vessel elements and fibers are unusually small and misshapen. Gall xylem has characteristics associated with wounding or infection: ray cells filled with phenolic deposits, and vessel elements occluded by tyloses and granular material. Frequent radial strands of undifferentiated callus tissue surrounded by necrophylactic periderms indicate sites of cambial damage of unknown cause. White areas within dark-colored gall xylem of some samples were free of most of these abnormalities, suggesting that a persistent agent is required for continuing tumor growth. Thickened outer bark harbored a variety of saprophytic fungi, especially hyphomycetes. Surface and internal morphology of black galls was also compared with similar stem galls caused by poplar budgall mites (Aceria parapopuli) and was found to be different. Bacteria, fungi, or mites were not obvious within living tissue, and further studies are necessary to determine the etiology of black galls. Key words: Populus tremuloides, poplar, black gall, wood anatomy.

Black stem galls on aspen and their relationship to decay by Phellinustremulae

Efficient use of trembling aspen (Populustremuloides Michx.) is often limited by the presence of extensive decay and stain. Aspen trees with black stem galls of unknown cause reportedly have less advanced decay caused by the fungus Phellinustremulae (Bond.) Bond. & Boriss. than do adjacent trees without galls. Nine field sites having large numbers of galled aspen were surveyed for the presence of P. tremulae conks. Logistic regression showed that the odds of a gall tree having at least one conk was 44% of that for trees without galls, and that the occurrence of conks varied among sites and increased with increasing tree diameter. Inclusion of black galls in models used to predict decay might result in greater accuracy on sites where these galls are prevalent. Black galls may also be potential sources of biological control agents against decay-causing organisms in aspen.

Phomalone, an antifungal metabolite of Phoma etheridgei

The metabolites produced by liquid cultures of Phoma etheridgei, a new fungus isolated from black galls of aspen, have been examined. This fungus is antagonistic to the aspen decay fungus Phellinus tremulae. The compound responsible for this antagonism has been isolated and its structure elucidated. Phomalone (1) is a previously undescribed natural product that possesses the same carbon skeleton as the Phoma pigmentivora metabolite LL-D253α. The structure was determined by physical methods, mainly 1H and 13C NMR. INAPT experiments played an important role. Some chemical transformations of phomalone (1) are described and it is shown by 13C-labelling experiments to be derived from six acetate units. Phomalone is active against Phellinus tremulae. Compounds 4, 6, 7, and 8 are also new natural products produced by P. etheridgei.

The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae

A series of new sesquiterpenes, the tremulanes, possessing a previously unreported substituted perhydroazulene carbon skeleton, has been isolated from liquid cultures of the aspen (Populus tremuloides) rotting fungus Phellinus tremulae. The structures were determined by NMR techniques ( 1 H- 1 H COSY, HMQC, and HMBC) and other physical methods including, in the case of tremulenolide A (6), X-ray crystallography. The chemical correlation of tremulenediol A (10) with tremulenolide A (6) is described as is the correlation of tremulenedial (8) with tremulenediol B (11). The absolute configuration of the compounds is assigned by application of the olefin octant rule to the allylic alcohol tremulenediol A (10). These new sesquiterpenes do not obey the biogenetic isoprene rule and it is suggested that they may not be derived from farnesyl pyrophosphate

2-Carbomethoxyoxepin: 1-carbomethoxybenzene 1,2-oxide. A metabolite of Phellinus tremulae.

The valence tautomer 2-carbomethoxyoxepin: 1-carbomethoxybenzene 1,2-oxide ( 1) has been isolated from liquid cultures of the wood-rotting fungus Phellinus tremulae. Methyl salicylate 2, a rearrangement product of the arene oxide 1, is produced by the same fungus. The biogenetic implications of these findings are discussed.

Antifungal activity of metabolites of Peniophora polygonia against the aspen decay fungus Phellinus tremulae

AbstractTen volatile and sixteen non‐volatile compounds have been isolated from culture filtrates of Peniophora polygonia. Among these, two volatile and three non‐volatile compounds significantly inhibited in vitro growth of Phellinus tremulae.

Novel 7-phenylheptan-3-ones from the fungus Phellinus tremulae

Novel 7-phenylheptan-3-ones from the fungus Phellinus tremulae