Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe
Journal of Basic Microbiology – January 01, 1989
Source: OpenAlex
Summary
Magic mushroom mycelium demonstrates remarkable chemical capabilities. *Psilocybe cubensis* mycelium, known for producing psilocybin, performs a unique biotransformation. It converts added tryptamine derivatives, like N,N-diethyltryptamine, into novel psychedelics. This involves specific hydroxylation, altering the original chemistry. Up to 3.3% 4-hydroxy-N,N-diethyltryptamine and 0.01–0.8% 4-phosphoryloxy-N,N-diethyltryptamine, new alkaloids, were isolated. This biochemistry highlights fungal biology's role in chemical synthesis and drug studies, potentially influencing neurotransmitter receptor influence on behavior. This stereochemistry is a first for fungal directed biosynthesis.
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.