Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe

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.