Differential inhibitory action of the fungal toxin orellanine on alkaline phosphatase isoenzymes

The inhibitory action of orellanine (3,3',4,4'-tetrahydroxy-2,2'-dipyridyl-1,1'-dioxide), a fungal toxin of Cortinarius orellanus Fr. and C. orellanoides R. Hry., on alkaline phosphatase isoenzymes was studied. Orellanine specifically inhibited alkaline phosphatase activity in LLC-PK1 renal epithelial cell cultures and in the colon carcinoma cell line Caco-2 without affecting gamma-glutamyl transpeptidase activity. Kinetic studies revealed that orellanine acts on renal alkaline phosphatase as a noncompetitive inhibitor, whereas the intestinal and placental isoforms are inhibited competitively.     

Isolation of a lethal toxin from Cortinarius orellanus Fr

The fungal toxin orellanine, isolated by Grzymala (10) from Cortinarius orellanus, seems to be a heterogeneous mixture of several toxic and nontoxic substances. We succeeded in isolating a lethal toxin which is sensitive to light and which is striking because of its long latency period. We consider this the main toxin of C. orellanus. Even in extremely high doses often times LD 100 mice do not die earlier than 48 hours after application. The paper gives details about the isolation and several properties of this slow acting toxin.     

Contribution to the nomenclature of Cortinarius subgenus Dermocybe

The correct citation of Dermocybe as a subgenus of Cortinarius should be: Cortinarius (Fr.) Fr. subgen. Dermocybe (Fr.) Sam., since it was Saccardo who definitely treated Dermocybe at the subgeneric level under the genus Coriinarius . According to the rules of nomenclature, the type species of Dermocybe must be Coriinarius cinnamomeus (L.: Fr.) Fr. Cortinarius croceus (Schaeff.: Fr.) H˜jiland is invalidly combined, and the new combination Cortinarius croceus (Schaeff.) Heiland is proposed. A neotype for Cortinarius croceus is also proposed. Hydrocybe palustris Moser is invalidly published since the author simultaneously published an alternative name, Cortinarius palusiris Moser. Therefore the combinations Dermocybe palustris (Moser) Moser and Coriinarius palusiris (Moser) Nez-dojminogo are invalid. The earliest legitimate name of the taxon is Cortinarius huronensis Ammirati & Smith.
Cortinarius sphagneti Orton is a later homonym of Cortinarius shagneti Sing. The earliest legitimate name of the former taxon is Cortinarius tubarius Ammirati & Smith.     

A new species and a new variety of Cortinarius sect. Defibulati from Niigata,Japan

 A new species and a new variety of Cortinarius sect. Defibulati are described and illustrated from Niigata, Japan. Cortinarius rugosolilacinus sp.nov., found in deciduous forests, is most similar to Cortinarius livido-ochraceus (=C. elatior), but differs mainly in its longer basidiospores, slender basidiocarp, and pale violet lamellae in the button stage. Cortinarius pseudosalor var. niigatensis var. nov., found in deciduous forests, is distinguished from the type variety by its brown to dark brown pileus with a wrinkled surface even when young. The differences between the two taxa and similar species are briefly discussed. Received: September 5, 2001 / Accepted: May 23, 2002     

Suppression of the toxic effect of soluble aluminium on fungi by dermocybin-1-β-D-glucopyranoside and orellanine from Cortinarius sanguineus and C. orellanoides

Extracts of Cortinarius sanguineus — containing anthraquinones — and C. orellanoides — containing orellanine — were examined for their ability to suppress the toxicity of aluminium ions by a bioassay experiment using the saprotrophic basidiomycete Mycena septentrionalis as the test organism. The aluminium concentrations used were: 0, 0.5,0.5e¹, 0.5e²,0.5e³, and 0.5e⁴ mM Al. All were given as aluminium sulphate, with or without the extract of Cortinarius sanguineus or C. orellanoides . The extract of C. sanguineus suppressed the toxic effect of Al up to 0.5e³ mM. The C. orellanoides extract inhibited growth of the test organism up to 0.5e¹ mM Al and suppressed the toxic effect of Al up to 0.5e³ mM Al. Mycena septentrionalis grew rapidly in 0.5e² and 0.5e³ mM Al. Chromatographic investigations indicated that Al was mainly bound to dermocybin-1-ß-D-glucopyranoside, but not to anthraquinone aglycones in the C. sanguineus extract. Corresponding procedures for the C. orellanoides extract revealed that Al was bound to orellanine (and orelline). Orellanine may form an Al-complex polymer at moderate Al levels and an Al-chelate at high Al levels. Aluminium removed the toxic effect of orellanine. The significance of a possible Al detoxifying mechanism for the tested fungi in nature is discussed.     

A re-evaluation of the Cortinarius scobinaceus and Cortinarius impolitus complex in the Mediterranean area

We have conducted a taxonomic study of Cortinarius belleri, C. cistohelvelloides, C. impolitus and C. scobinaceus from material collected in Spain, France, Italy, Portugal and Morocco. Based on anatomy, morphology, ecology and distribution (geographical data) we recognize two species, C. impolitus and C. scobinaceus, and the new combination C. scobinaceus var. cistohelvelloides is made. Cortinarius belleri, C. cistohelvelloides, C. impolitus and C. scobinaceus have been typed, and a key for identification of these taxa is included.     

A new variety of <Emphasis Type="Italic">Cortinarius subalboviolaceus</Emphasis> (Sect. <Emphasis Type="Italic">Sericeocybe</Emphasis>) from Japan

Cortinarius subalboviolaceus var. niigatensis var. nov., which grows in deciduous forests, is described and illustrated from Niigata and Gunma prefectures, Japan. It differs from C. subalboviolaceus var. subalboviolaceus mainly in its more distinct violet coloration and somewhat larger size of the basidiocarp.     

N-glucosyl-1H-indole derivatives from Cortinarius brunneus (Basidiomycetes)

Two new N-glucosylated indole alkaloids were isolated from fruiting bodies of the basidiomycete Cortinarius brunneus (Pers.) Fr. The structures were elucidated by means of the spectroscopic data. Additionally, the very recently reported compounds N-1-beta-glucopyranosyl-3-(carboxymethyl)-1H-indole (3) and N-1-beta-glucopyranosyl-3-(2-methoxy-2-oxoethyl)-1H-indole (4) could be detected. Compound 3 is the N-glucoside of the plant-growth regulator 1H-indole-3-acetic acid (IAA), but, in contrast, it does not exhibit auxin-like activity in an Arabidopsis thaliana tap root elongation assay.     

Cortinarius subgenus Dermocybe in Greenland

The following species of Cortinarius subg. Dermocybe are recorded from Greenland: C. cinnamomeus, C. croceus, C. norvegicus, C. croceoconus, C. huronensis var. huronensis, C. uliginosus, C. cinnamomeoluteus , and C. polaris . Ecological and plant geographical features are discussed for each species. Cortinarius cinnamomeus and C. uliginosirs seem to be southern species never penetrating into the arctic zones; C. croceus, C. croceoconus, C. huronensis var. huronensis , and C. cinnamomeoluteus southern species penetrating into the arctic zones; and C. norvegicus and C. polaris true arctic species. Cortinarius norvegicus is probably continental, while the other species are distributed in continental as well as oceanic areas.     

Cortinarius sanguineus and equally red species in Europe with an emphasis on northern European material

The red species of Cortinarius subgenus Dermocybe in Europe were studied based on morphological and molecular data. Three completely red species were recognized: C. sanguineus (syn. C. sanguineus var. aurantiovaginatus), C. puniceus (syn. C. cruentus, C. rubrosanguineus) and C. vitiosus comb. nov. Cortinarius sanguineus has dusky red to red pileus, reddish yellow mycelium and lacking or with only slightly encrusted hyphae in pileipellis. It occurs in mesic to damp forests with Picea, often on rich soil in the boreal and montane areas of Europe, presumably also in eastern Canada. Cortinarius puniceus differs from C. sanguineus by its stronger purplish red, narrower spores and spot-like encrusted hyphae in pileipellis. It grows with deciduous trees in the temperate zone of Europe. Cortinarius vitiosus is known only from Fennoscandia and occurs in dry to mesic coniferous forests. It has fairly thin, often zonate, dark red to dark reddish brown pileus, pale red mycelium, small spores and encrusted lamellar trama and pileipellis hyphae. In addition to these three species C. fervidus and C. phoeniceus occasionally have red basidiomes. The relationships of the species were inferred by analysis of ITS sequences. Our study suggests that the section Sanguinei, as earlier defined, is polyphyletic. Here the section is limited to include C. sanguineus, C. puniceus and North American D. sierraensis. The relationships with other red species were not determined. Section Dermocybe, including C. cinnamomeus, C. croceus and C. uliginosus, formed a monophyletic group, and the section Malicoriae had some support. A total of 34 new sequences are published including nine from type specimens.     

<Emphasis Type="Italic">Cortinarius stjernegaardii</Emphasis> and <Emphasis Type="Italic">C. kristinae</Emphasis> (Basidiomycota,Agaricales), two new European species with a mainly northern distribution

We describe two new, mainly North European species of basidiomycetous fungi. Cortinarius stjernegaardii belongs to the section Percomes containing several similar species with greenish-yellow, anthraquinonoid pigments and peculiar smells. The species has hitherto been identified as” C. bulbopodius” in the Nordic countries, an epithet which, however, is reduced to a synonym of C. aurilicis. Cortinarius kristinae belongs to the section Calochroi, which includes many morphologically similar species with sharply marginate bulbose stipes and yellow pileus colours. The species are distinguished from related taxa by molecular data (ribosomal ITS region), and typical specimens can be identified by a combination of basidiocarp coloration, stature, microscopy, reactions with KOH, and habitat.     

中国丝膜菌属三个新记录种

报道了丝膜菌属Cortinarius Telamonia亚属的3个中国新记录种,其中双环丝膜菌C bivelus产自我国东北和西南地区,亚石榴丝膜菌C.subbalaustinus产自云南省,亚野丝膜菌C subtorvus产自西藏自治区.对这3个种进行了详细的描述,并提供其宏观特征和显微结构图片.     

New Cortinarius species from Nothofagus forests in South Chile

Four new Cortinarius species are described from Nothofagus forests in South Chile. Cortinarius aurantiorufus and C. punctatisporus, subgenus Phlegmacium, stirps Inflatipes, are mainly characterized by a viscid to glutinous pileus and a bulbous whitish stipe. They differ in the color of the pileus, and shape, ornamentation, and size of the basidiospores. Futhermore, C. punctatisporus has a translucently striate pileus. Cortinarius rubrivelatus and C. parahumilis belong to subgenus Telamonia, stirps Brunneivelatus and Scabrisporus, respectively. Cortinarius rubrivelatus has a reddish veil, a viscid pileus, and large, ellipsoid to amygdaliform basidiospores. Cortinarius parahumilis has small, subglobose to broadly elliptical, minutely verrucose basidiospores and a viscid pileus.     

Problems in application of the terms ‘blastic’ and ‘thallic’ to modes of conidiogenesis in some onygenalean fungi

A woman suffering from acute tubulo-interstitial nephritis was admitted to the hospital ten days after deliberate intoxication by ingestion of Cortinarius orellanus. Orellanine, the main toxin responsible for orellanine poisoning, was detected in biological fluids and renal biopsies. It was assayed by direct spectrofluorimetry on two-dimensional thin-layer chromatograms after specific photodecomposition into orelline. The orellanine concentration was 6.12 mg/l in the plasma (10 days after ingestion). Orellanine levels in renal biopsies were 7 g per 25 mm³ of the first biopsy (13 days after ingestion) and 24 g per 8 mm³ of the second biopsy (6 months later).Taken in part from the doctorate thesis of S. Rapior.     

Multivariate analysis of fatty acids in spores of higher basidiomycetes: a new method for chemotaxonomical classification of fungi

The aim of the present work was to study the possibility of using the fatty acid content in the basidiospores as a taxonomic tool. Basidiospores of Armillaria borealis, Amanita muscaria, Agaricus sylvicola, Hypholoma capnoides, Cortinarius nemorensis and Russula delica were used. The content of fatty acids as well as other substances may vary to a certain degree depending on the part (pileus, stipe, lamella) or stage of development of the actual basidiocarp analysed. Moreover, substances from fungivorous invertebrates, parasitic fungi or bacteria may be found in the chemical analyses of the basidiocarps. Chemotaxonomic conclusions may, therefore, be burdened with serious uncertainties. On the other hand, the ripe basidiospores are terminated structures and belong to the most homogenous structures encountered from a basidiocarp. Their shape, size, colour and ornamentation are considerably homogenous within an actual species. Therefore, the basidiospores are often used as a reliable differentiating characteristic separating species as well as taxa of higher categories. From a practical point of view, ripe spores are easy to obtain in relatively large quantities with simple techniques, and they are not so prone to decay as the carpophore tissue. In the present study, gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), after methanolysis of the fungus spores, were used to map essential fatty acids in basidiomycetes. Gas chromatography and gas chromatography-mass spectrometry revealed the presence of fatty acids of C12:0-C24:0 size in the basidiospores of these higher basidiomycetes. The major fatty acid in H. capnoides is C18:2, and the major fatty acid in the other species is C18:1. The basidiospores proved to be a good source of fatty acids for chemotaxonomic investigations of agarics.     

丝膜菌属有毒蘑菇及其毒素研究进展

丝膜菌属Cortinarius是蘑菇目Agaricales中最大的属,目前已描述的物种超过2 000种,该属中一些种类含有剧毒的奥来毒素,可引起急性肾衰并导致死亡。本文对丝膜菌属有毒蘑菇中毒及种类、中毒临床症状、奥来毒素的检测方法、毒性毒理和中毒治疗以及奥来毒素在肾癌治疗中的应用等方面进行了梳理和综述,并对一些热点研究领域进行了展望。     

Effect of a mushroom toxin, orellanine, on the cellular slime mold Dictyostelium discoideum and the bacterium Escherichia coli

Abstract Orellanine, the toxic principle of Cortinarius orellanus efficiently inhibited the growth of the amoebae Dictyostelium discoideum . No significant effect on phagocytosis or pinocytosis was observed. The growth of the bacterium Escherichia coli was inhibited with a sensitivity similar to that of D. discoideum .     

Peroxidase-Mediated Oxidation, a Possible Pathway for Activation of the Fungal Nephrotoxin Orellanine and Related Compounds. ESR and Spin-Trapping Studies

Orellanine is the tetrahydroxylated and di-N-oxidized bipyridine toxin extracted from several Cortinarius mushrooms among them C. orellanus. The pathogenic mechanism involved in the C. orellanus-poisoning by orellanine leading to kidney impairment is not yet fully understood until now. Electron spin resonance (ESR) spectroscopy has been used to study the activation of orellanine by horseradish peroxidase/H₂O₂ system at physiological pH. Evidence for a one-electron oxidation of the toxin by this enzymatic system to an ortho-semiquinone radical intermediate is presented.

The orellanine ortho-semiquinone generated by the peroxidase/H₂O₂ system abstracts hydrogen from glutathione, generating the glutathionyl radical which is spin-trapped by 5,5'-dimethyl-1-pyrroline N-oxide (DMPO) and subsequently detected by ESR spectroscopy. Similarly, the ortho-semiquinone abstracts hydrogen from ascorbic acid to generate the ascorbyl radical which is detected by direct ESR. The peroxidatic oxidation of orellanine to semiquinone followed by its reduction by glutathione or ascorbic acid does not induce dioxygen uptake. The relationship between chemical structure and HRP oxidation of orellanine-related molecules, namely orelline and DHBPO₂ (the parent molecule lacking of hydroxyl groups in 3 and 3' position) has been investigated in absence or in presence of reducing agents. None of the orellanine-related compounds can be oxidized by the HRP/H₂O₂ system, showing that both catecholic moieties and aminoxide groups are necessary for observing the formation of the ortho-semiquinone form of orellanine. As shown for the (photo)chemical oxidation of orellanine, the mechanism of toxicity could be correlated with a depletion of glutathione and ascorbate levels which are implicated in the defence against oxidative damage.