Isolierunǵ von (‐)‐<i>allo</i>‐Muscarin aus <i>Amanita muscaria</i>. 33. Mitteilung über Inhaltsstoffe von Fliegenpilzen

Schleusener, E.; Eugster, C. H.

doi:10.1002/hlca.19700530116

Cited by 14 publications

(1 citation statement)

References 7 publications

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“…Fr.) Hooker und von Inocybe-Spezies [2][3] [4] erhob sich die Frage nach der Chiralitat dieser Verbindungen, weil erwartet werden darf, dass ihre Kenntnis Einblicke in die noch unbekannte Biogenese des Muscarins und seiner Isomerer ge wonnen werden konnen.…”

unclassified

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

Bollinger

Eugster

1971

Helvetica Chimica Acta

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kvidence une limitation du modkle diatomique : l'anharmonicitk d'un systkme polyatornique assimilk B un systkme diatomique est augmentke, par rapport A celle d'une molkcule diatomique, B cause de la prksence d'un grand nombre d'oscillateurs et des couplages qu'ils favorisent et qui existent indkpendamment de tout modde. L'image donnke par de tels modkles diatomiques ne rend donc pas compte d'une situation moyennequant A l'anharmonicitkmais au contraire extrCme, puisqu'elle est b a d e SUT une bande de tr6s forte anharmonicitk.L'inaptitude des modes de vibration de groupe B dkcrire les harmoniques sup& rieurs n'a dcigale que celle des modes normaux de vibration B dcicrire les premiers hal-moniques.Ainsi donc, l'ktude des vibrations de valence C-H des alcanes a dkmontrk leur caract6re fortement localisk, au point que les modeles de groupe sont dkjA prkfkrables B celui des coordonnkes normales dans la rkgion des fondamentales [l], que les vibrations normales sont mises en dkfaut par les rkgles de symCtrie dans la rkgion du premier harmonique (cf. note a), et que les modkles de groupe, eux-m&mes, sont inefficaces dans celles des harmoniques supkrieurs et peuvent &tre remplacks par un modkle diatomique.Xous reinercions sinckrenient le Fonds National dc l'aide accord& pour ce travail.Zusammeizfassung. Die enantionieren epi-Normuscarinc lassen sich in Form der diastercotneren a-Methoxypropionsaurecster gas-chroniatographisch trennen. Bci Venvendung von (5')-u-Mcthoxypropionsaure als Vcresterungslromponentc konnte gezeig't wcrden, dass das in lnocybegeophylla (S'om. ex Fr.) Qudl. (Busidiomycetes) vorkomniende epi-Muscarin das (+ )-Enantiomere darstellt. l) 35. Mitteilung siehe [l] ; 34. Mitteilung siehe [Z],

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

Bollinger

Eugster

1971

Helvetica Chimica Acta

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ChemInform Abstract: INHALTSSTOFFE VON FLIEGENPILZEN 33. MITT. ISOLIERUNG VON (‐)‐ALLO‐MUSCARIN AUS AMANITA MUSCARIA

Schleusener¹,

Eugster²

1970

Chemischer Informationsdienst. Organische Chemie

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Muscarine and Muscarine Isomers in Selected Inocybe Species

Catalfomo

Eugster

1970

Helvetica Chimica Acta

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Summary. The distribution and relative concentrations of muscarine and its isomers in I.nocybe species were determined. Notable was the finding that I . cinnamomea A . H . Smith, 1.geophyUa Karst. and I . Zacera (Fr.) QuSZ. contained concentrations of e$i-muscarine equal to or higher than muscarine itself.The reasons for a re-examination of the occurrence of muscarine in mushroom: were dicussed in papers No. 28 [2] and No. 29 [3] of this series. After the isolation of muscarine from Amanita muscaria (L. ex Fr.) Hooker and certain Inocybe species, the mother liquors were examined for the presence of the stereoisomers of muscarine. The presence of allo-muscarine, epi-muscarine, and possibly epiallo-muscarine, in A . muscuria and certain Inocybe species was reported 141. Later, (-)-allo-muscarine was isolated from A . muscaria [l]. During these preliminary investigations, it was suspected that the muscarine fractions of certain Inocybe species contained a higher proportion of the stereoisomers of muscarine than muscarine itself. This observation provided the impetus for the present study.Muscarine muscarine is widely distributed, and where it often occurs in relatively high concentrations, to determine to what extent the stereoisomers of this compound are distributed throughout this genus. It is felt that these data might be useful in resolving some of the inconsistencies associated with the pharmacology and biosynthesis of muscarine, and possibly contribute to the taxonomic characters of the genus Inocybe. The species selected are somewhat representative of the genus Inocybe and, except for I.subbrunnea and 1.3398, all are known to contain muscarine. The total muscarine fractip from each species was obtained by the method described subsequently. Partially purified extracts of muscarine chloride were pyrolysed, and the resulting norbases were separated, identified, and assayed according to the procedures ofThe results are summarized in the Table. The following conclusions are noteworthy. Nor-muscarine and norepi-muscarine were identified with certainty in all species examined. Norallo-muscarine was detected 2,

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Isolierunǵ von (‐)‐allo‐Muscarin aus Amanita muscaria. 33. Mitteilung über Inhaltsstoffe von Fliegenpilzen

Abstract: Isolierung von (-)-allo-Muscarin aus

Cited by 14 publications

References 7 publications

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

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

ChemInform Abstract: INHALTSSTOFFE VON FLIEGENPILZEN 33. MITT. ISOLIERUNG VON (‐)‐ALLO‐MUSCARIN AUS AMANITA MUSCARIA

Muscarine and Muscarine Isomers in Selected Inocybe Species

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