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Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms.


ABSTRACT: Upon injury, psychotropic psilocybin-producing mushrooms instantly develop an intense blue color, the chemical basis and mode of formation of which has remained elusive. We report two enzymes from Psilocybe cubensis that carry out a two-step cascade to prepare psilocybin for oxidative oligomerization that leads to blue products. The phosphatase PsiP removes the 4-O-phosphate group to yield psilocin, while PsiL oxidizes its 4-hydroxy group. The PsiL reaction was monitored by in?situ 13 C?NMR spectroscopy, which indicated that oxidative coupling of psilocyl residues occurs primarily via C-5. MS and IR spectroscopy indicated the formation of a heterogeneous mixture of preferentially psilocyl 3- to 13-mers and suggest multiple oligomerization routes, depending on oxidative power and substrate concentration. The results also imply that phosphate ester of psilocybin serves a reversible protective function.

SUBMITTER: Lenz C 

PROVIDER: S-EPMC7004109 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms.

Lenz Claudius C   Wick Jonas J   Braga Daniel D   García-Altares María M   Lackner Gerald G   Hertweck Christian C   Gressler Markus M   Hoffmeister Dirk D  

Angewandte Chemie (International ed. in English) 20191204 4


Upon injury, psychotropic psilocybin-producing mushrooms instantly develop an intense blue color, the chemical basis and mode of formation of which has remained elusive. We report two enzymes from Psilocybe cubensis that carry out a two-step cascade to prepare psilocybin for oxidative oligomerization that leads to blue products. The phosphatase PsiP removes the 4-O-phosphate group to yield psilocin, while PsiL oxidizes its 4-hydroxy group. The PsiL reaction was monitored by in situ <sup>13</sup>  ...[more]

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