Injury‐Triggered Blueing Reactions of Psilocybe “Magic” Mushrooms
Identifieur interne : 000522 ( Main/Merge ); précédent : 000521; suivant : 000523Injury‐Triggered Blueing Reactions of Psilocybe “Magic” Mushrooms
Auteurs : Claudius Lenz ; Jonas Wick ; Daniel Braga ; María García-Altares ; Gerald Lackner ; Christian Hertweck ; Markus Gressler ; Dirk HoffmeisterSource :
- Angewandte Chemie (International Ed. in English) [ 1433-7851 ] ; 2019.
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
Url:
DOI: 10.1002/anie.201910175
PubMed: 31725937
PubMed Central: 7004109
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PMC:7004109Le document en format XML
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<front><div type="abstract" xml:lang="en"><title>Abstract</title>
<p>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 <italic>Psilocybe cubensis</italic>
that carry out a two‐step cascade to prepare psilocybin for oxidative oligomerization that leads to blue products. The phosphatase PsiP removes the 4‐<italic>O</italic>
‐phosphate group to yield psilocin, while PsiL oxidizes its 4‐hydroxy group. The PsiL reaction was monitored by in situ <sup>13</sup>
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.</p>
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