Abstract
Phalloidin (Formula 1a) is one of the toxic components of the toadstool Amanita phalloides (Wieland, 1968); it is accompanied in the mushroom by several toxic relatives of which only phallacidin (Formula 1b) is shown in the general formula. Chemical manipulations can also lead to toxic derivatives or can annihilate the toxicity of the molecule. By degradation of the branched side chain 1a is transformed to desmethylphalloin (Formula 1c), a still toxic product, which can also be obtained in the tritiated state by this reaction. Radioactive carbon can be introduced by methylation of the indole nucleus of 1a giving a still toxic Nind-methyl compound (Formula 1d) (Faulstich and Wieland, 1971). On oxidation with hydrogen peroxide in acetic acid, two diastereomeric sulfoxides
are formed from 1a. (Faulstich et al., 1968), a toxic one (Formula 1e) with R-chirality at the SO center and a nontoxic one (Formula 1f) with S-chirality (Wieland et al., 1974). Vanishing of toxicity is also observed after opening of the thioether bridge by replacing the sulfur by two H-atoms by means of Raney-nickel (dethiophalloidin, Formula 1g) or by selective fission of a predestinated peptide bond which leads to a secophalloidin (Formula 1h).
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Wieland, T. (1976). Phallotoxins and Microfilaments. In: Heilmeyer, L.M.G., Rüegg, J.C., Wieland, T. (eds) Molecular Basis of Motility. 26. Colloquium der Gesellschaft für Biologische Chemie 10.–12. April 1975 in Mosbach/Baden, vol 26. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-81013-8_16
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DOI: https://doi.org/10.1007/978-3-642-81013-8_16
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