Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

Mycelial cultures of Psilocybe cubensis that naturally produce psilocybin and psilocin can efficiently add a hydroxyl group to tryptamine derivatives at the 4-position. When synthetic N,N-diethyltryptamine was added, the fungus converted it into high amounts of 4-hydroxy-N,N-diethyltryptamine (up to 3.3%) and smaller amounts of 4-phosphoryloxy-N,N-diethyltryptamine (0.01–0.8%) in the fruiting bodies. This marks the first example of directed biosynthesis of tryptamine substances by fungi. Surface cultures of Psilocybe semilanceata also effectively transformed N-methyltryptamine. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified in the biomasses, but no alkaloids were found in the culture medium.

Study at a glance

Abstract

Abstract Mycelial cultures of Psilocybe cubensis capable of forming psilocybin and psilocin de novo display a high capacity for hydroxylation of tryptamine derivatives at the 4‐position. A specific biotransformation of added synthetic N,N‐diethyl‐tryptamine was found. Thus high amounts of 4‐hydroxy‐N,N‐diethyltryptamine (up to 3.3%) and a minor quantity of 4‐phosphoryloxy‐N,N‐diethyltryptamine (0.01–0.8%) were isolated from fruiting bodies of Psilocybe cubensis in corresponding experiments. This is the first example of a directed biosynthesis of tryptamine substances by fungi. An effective biotransformation of N‐methyltryptamine was also demonstrated with surface cultures of Psilocybe semilanceata. Baeocystin, a possible natural precursor of psilocybin, was detected and quantified in the biomasses. No alkaloids could be found in the culture medium.