A „Magic Mushroom“ Multi‐Product Sesquiterpene Synthase
Eike Schäfer, Stefan Bartram, Felix Trottmann, Markus Gressler, Christian Hertweck, Dirk Hoffmeister, Paula Sophie Seibold, Veit G. Haensch, Andrew R Chadeayne, Sarah E. O’connor
ChemBioChem August 24, 2023 DOI: 10.1002/cbic.202300511 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Psilocybe cubensis and related Psilocybe species |
| Topics | Psilocybin |
| Keywords | Enzyme Sesquiterpene Natural product Biochemistry Escherichia coli Terpenoid Mushroom Botany |
| Citations | 7 |
| Key findings | CubA is a multi-product sesquiterpene synthase that produces cubebol, β-copaene, δ-cadinene, and germacrene D, with β-copaene and δ-cadinene detected in mature Psilocybe cubensis mushrooms. |
Abstract
Abstract Psilocybe “magic mushrooms” are chemically well understood for their psychotropic tryptamines. However, the diversity of their other specialized metabolites, in particular terpenoids, has largely remained an open question. Yet, knowledge on the natural product background is critical to understand if other compounds modulate the psychotropic pharmacological effects. CubA, the single clade II sesquiterpene synthase of P. cubensis , was heterologously produced in Escherichia coli and characterized in vitro , complemented by in vivo product formation assays in Aspergillus niger as a heterologous host. Extensive GC‐MS analyses proved a function as multi‐product synthase and, depending on the reaction conditions, cubebol, β‐copaene, δ‐cadinene, and germacrene D were detected as the major products of CubA. In addition, mature P. cubensis carpophores were analysed chromatographically which led to the detection of β‐copaene and δ‐cadinene. Enzymes closely related to CubA are encoded in the genomes of various Psilocybe species. Therefore, our results provide insight into the metabolic capacity of the entire genus.