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Injury-Triggered Blueing Reactions of Psilocybe “Magic” Mushrooms

Summary

When magic mushrooms are injured or bruised, they turn blue—a phenomenon that has puzzled scientists for decades. Researchers discovered that two enzymes work together in a two-step process: first, an enzyme removes a protective chemical tag from psilocybin, converting it to psilocin; then, a second enzyme oxidizes this molecule, causing it to link together into larger chains that appear blue. This blue color appears to be a defense mechanism that protects the mushroom from insects.

Background

Psilocybe mushrooms develop an intense blue color upon injury or bruising, a phenomenon that has attracted scientific attention for decades. However, the chemical basis and biochemical mechanism underlying this blueing reaction has remained unknown. Previous research suggested the chromophore might be ortho-coupled biarylidenedione derivatives derived from psilocin.

Objective

To elucidate the chemical structure of the blue chromophore and identify the enzymes responsible for the blueing reaction in Psilocybe cubensis mushrooms. The study aimed to understand the enzymatic cascade that converts psilocybin into blue oligomeric products upon injury.

Results

Two enzymes were identified: PsiP, a phosphatase that dephosphorylates psilocybin to psilocin, and PsiL, a laccase that oxidizes psilocin’s 4-hydroxy group. The blue color results from heterogeneous quinoid psilocyl oligomers (3-13 mers) coupled primarily via carbon-5, with oligomerization occurring through multiple oxidative pathways depending on oxidant concentration and substrate availability.

Conclusion

The blueing reaction is a two-step enzymatic cascade involving dephosphorylation followed by oxidative oligomerization. The phosphate ester serves as a reversible protective group that keeps psilocybin stable until injury triggers enzyme activity, producing oligomeric defensive compounds. This represents an elegant wound-activated chemical defense system in these fungi.
  • Published in:Angewandte Chemie International Edition,
  • Study Type:Experimental Research,
  • Source: 10.1002/anie.201910175, PMID: 31725937
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