Nachweis von (+)‐<i>epi</i>‐Muscarin in <i>Inocybe geophylla</i>. 36. Mitteilung über Muscarin und verwandte Stoffe

Bollinger, H.; Eugster, C. H.

doi:10.1002/hlca.19710540512

Cited by 9 publications

(1 citation statement)

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“…A few studies have been carried out on Inocybe species to identify their toxic principles: Jensen et al, 2006 reported aeruginascin, (a trimethyl ammonium analog of psilocybin) in Inocybe aeruginascens 8 ; Zhao et al 9 associated the toxicity of Inocybe umbrinella to the presence of lectins and biogenic amines were identified in I. patouillard 10 . The toxin muscarine was determined in I. cinnamomea, I. geophylla , and I. lacera 11 and its isomer epi-muscarine was identified in I. geophylla 12 . Gas Chromatography is one of the techniques for toxicological assessment of volatile toxicants while for non-volatile toxicants it is Liquid Chromatography 13 .…”

Section: Introductionmentioning

confidence: 99%

Toxic metabolite profiling of Inocybe virosa

Latha

Naveen

Naika

et al. 2020

Sci Rep

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Wild mushroom foraging involves a high risk of unintentional consumption of poisonous mushrooms which is a serious health concern. This problem arises due to the close morphological resemblances of toxic mushrooms with edible ones. The genus Inocybe comprises both edible and poisonous species and it is therefore important to differentiate them. Knowledge about their chemical nature will unambiguously determine their edibility and aid in an effective treatment in case of poisonings. In the present study, the presence of volatile toxic metabolites was verified in Inocybe virosa by gas chromatography. Methyl palmitate, phenol, 3,5-bis (1,1-dimethyl ethyl) and phytol were the identified compounds with suspected toxicity. The presence of the toxin muscarine was confirmed by liquid chromatography. The in vitro study showed that there was negligible effect of the digestion process on muscarine content or its toxicity. Therefore, the role of muscarine in the toxicity of Inocybe virosa was studied using a bioassay wherein metameters such as hypersalivation, immobility, excessive defecation, heart rate and micturition were measured. Administration of muscarine resulted in an earlier onset of symptoms and the extract showed a slightly stronger muscarinic effect in comparison to an equivalent dose of muscarine estimated in it. Further, the biological fate of muscarine was studied by pharmacokinetics and gamma scintigraphy in New Zealand white rabbits. Significant amount of the toxin was rapidly and effectively concentrated in the thorax and head region. This study closely explains the early muscarinic response such as miosis and salivation in mice. By the end of 24 h, a relatively major proportion of muscarine administered was accumulated in the liver which stands as an explanation to the hepatotoxicity of Inocybe virosa. This is one of the rare studies that has attempted to understand the toxic potential of muscarine which has previously been explored extensively for its pharmaceutical applications. Wild mushroom foraging involves a high risk of unintentional consumption of poisonous mushrooms which is a serious health concern. This problem arises due to the close morphological resemblance of toxic mushrooms with edible ones. The genus Inocybe also comprises both edible and poisonous species and it is therefore important to differentiate them. The species Inocybe virosa which is the focus of the present study is closely allied to Inocybe cutifracta which is an edible mushroom. The taxonomic classification of a mushroom species under the genus Inocybe, generally raises a suspicion about its edibility. This inevitable caution stems from the literature which abounds in cases of poisonings due to Inocybe mushrooms. Some of the poisonings reported have been associated with Inocybe fastigiata 1,2 , I. tristis 3 , I. anterospora 4 , I. aeruginascens 5 and I. patouillardii 6. Species such as I. asterospora, I. gobeyi, I. napipes, I. repanda, I. radiata, I. rimosa show psychotropic effects and classified as neurotoxic. Most of the I...

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Section: Introductionmentioning

confidence: 99%

Toxic metabolite profiling of Inocybe virosa

Latha

Naveen

Naika

et al. 2020

Sci Rep

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ChemInform Abstract: MUSCARIN UND VERWANDTE STOFFE 36. MITT. NACHWEIS VON (+)‐EPI‐MUSCARIN IN INOCYBE GEOPHYLLA

Bollinger¹,

Eugster²

1971

Chemischer Informationsdienst. Organische Chemie

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Konfigurative Zusammenhänge in der Muscarinreihe; Chiralität des epi‐, allo‐ und epiallo‐Muscarins, des Muscarons und allo‐Muscarons. Zur biogenese des muscarins 37. Mitteilung über muscarin und verwandte stoffe

Bollinger

Eugster

1971

Helvetica Chimica Acta

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1. Einleitung. -Uisher ist erst die Cliiralitat des (+)und des (-)-Muscarins durcli clieniische Verkniipfung mit L-bzw. n-Glucosamin und 2-Desoxy-~-ribose festgelegt 3) 1 2 1 [3] [4]. Seit wir nacliweisen konnten, dass alle stereoineren Muscarine in der Natur vorkommen [5] ' 61 und zudeni (--)-do-Muscarin aus Arnanita mnuscaria l ) 36. Mitteilung s [l]. 2) )Ketr. Muscaron, s. Xbschnitt4. ~. . >Aus dcr Iliplomarbeit (1970) und der gcplanten 1)issertation von H e i w i c h Bollingev.3. Chemische Verkniipfungsreaktionen (s. Formelschema 1). -I n friiheren Arbeiten [20] [21] wurde beobachtet, dass die mit verschiedenartigen Reduktionsmitteln durchgefuhrte Reduktion von Normuscaron unstereospezifisch zu einern Gemisch aller stereomerer Norniuscarine fuhrt. Als Grund wurde eine an C(2) leiclit verlaufende Epimerisierung angenommen. Diese Ergebnisse sind noch vor kurzer Zeit von Hardegger & Halder [22] an eineni speziell gereinigten Normuscaron in vollem Umfang bestatigt worden. Es schien uns deshalb am einfachsten, optisch aktives Normuscaron herzustellen, dieses zu reduzieren und das Gemisch der entstandenen Noralkohole chromatographisch aufzutrennen. Diese mussten alle identische Konfiguration an (75) aufweisen. Fur die Herstellung der Norketone bewahrte sich am besten Chroinsaure in 6~ H,SO,, rnit der bei 40-minutiger Oxydationsdauer bei 50" Rohausbeuten von 65% erzielt wurden. Viele andere Oxydationsmittel, wie z.B. Ag,CO,/Ceiite [23] oder Pt/O, in Wasser, bewahrten sich nicht. Die Reinheitspriifung

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Nachweis von (+)‐epi‐Muscarin in Inocybe geophylla. 36. Mitteilung über Muscarin und verwandte Stoffe

Cited by 9 publications

References 4 publications

Toxic metabolite profiling of Inocybe virosa

Toxic metabolite profiling of Inocybe virosa

ChemInform Abstract: MUSCARIN UND VERWANDTE STOFFE 36. MITT. NACHWEIS VON (+)‐EPI‐MUSCARIN IN INOCYBE GEOPHYLLA

Konfigurative Zusammenhänge in der Muscarinreihe; Chiralität des epi‐, allo‐ und epiallo‐Muscarins, des Muscarons und allo‐Muscarons. Zur biogenese des muscarins 37. Mitteilung über muscarin und verwandte stoffe

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