Hi there!
I have come across a Journal translated "News from Chemistry", which is mostly about new emerged stuff. In this Journal there was an article about the blue coloration of Psilos when you bruise their tissue. As it was derived from a recently published paper, I guess this is a kind of new theory so it may be new to many people here.
The "traditional" coloration reason given by wikipedia:
Quote:This reaction is thought to be due to the oxidation of psilocybin after the outer surface of the fruit body has been breached.[19] The degree of bluing in a Psilocybe fruit body roughly correlates with the concentration of psilocin in the mushroom.
Not really in detail, also it seems there is not much other info around. I just found
this, where in 1967 it was stated a chinone-like molecule is derived.
Now the article in that journal is focused on
this paper (
doi: 10.1002/anie.201910175). Here they describe the coloration in deep according to their theory as the following:
Upon tissue damage multiple enzymes convert the molecule as follows:
psilocybin (1) --dephosphorylation--> Psilocin (2)
Psilocin (2) --single-electron-transfer--> radical intermediate (thing with red dots)
reactive intermediate --> dimers (5,6) or oligomers (7-11)
Now the author also talks about the possible reason for this reaction and its physiological functions.
According to most theories the psilocin is a protection against animals who may feed on them (irony people actually eat it because of that ...).
But the author has developed a second theory:
According to him the oligomers may be the actual biologically active species, which is not a psychotropic agent, but has a direct protection function.
According to him these oligomers may produce reactive oxygen species (by conduction the single-electron-transfer) when they enter the basic, oxidative digestive system of insects or their larvae. Also they may bind to proteins of their digestive system and cause a precipitation, rendering them either useless or even kill the animal.
He mentions this would explain the rather unconventional usage of a Phosphate group to inactivate the 4-OH of the more reactive Psilocin. The dephosphorylation reaction is very fast to conduct and may be used to switch the molecule from harmless to harmful for certain insects.
So basically an oxidation reaction is still also involved, but if its true what the author said, its much more fancy than just "yeah buddy, your Psilo oxidized, still good to use!"
Actually when I think about it, if the author is correct, then all people should avoid bruising their mushrooms, as this would reduce their Psilo content (ok, maybe its not making a difference, but who does not want to go the most efficient way
).