Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms.
Angew Chem Int Ed Engl
; 59(4): 1450-1454, 2020 01 20.
Article
in En
| MEDLINE
| ID: mdl-31725937
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 inâ
situ 13 Câ
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.
Key words
Full text:
1
Database:
MEDLINE
Main subject:
Biological Products
/
Agaricales
/
Psilocybe
/
Hallucinogens
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2020
Type:
Article
Affiliation country:
Germany