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Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization

Psilocin (1) is the dephosphorylated and psychotropic metabolite of the mushroom natural product psilocybin. Oxidation of the phenolic hydroxy group at the C‐4 position of 1 results in formation of oligomeric indoloquinoid chromophores responsible for the iconic blueing of bruised psilocybin‐produci...

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Detalles Bibliográficos
Autores principales: Lenz, Claudius, Dörner, Sebastian, Sherwood, Alexander, Hoffmeister, Dirk
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457229/
https://www.ncbi.nlm.nih.gov/pubmed/34062028
http://dx.doi.org/10.1002/chem.202101382
Descripción
Sumario:Psilocin (1) is the dephosphorylated and psychotropic metabolite of the mushroom natural product psilocybin. Oxidation of the phenolic hydroxy group at the C‐4 position of 1 results in formation of oligomeric indoloquinoid chromophores responsible for the iconic blueing of bruised psilocybin‐producing mushrooms. Based on previous NMR experiments, the hypothesis included that the 5,5’‐coupled quinone dimer of 1 was the primary product responsible for the blue color. To test this hypothesis, ring‐methylated 1 derivatives were synthesized to provide stable analogs of 1 dimers that could be completely characterized. The chemically oxidized derivatives were spectroscopically analyzed and compared to computationally derived absorbance spectra. Experimental evidence did not support the original hypothesis. Rather, the blue color was shown to stem from the quinoid 7,7’‐coupled dimer of 1.