The zygomycete Mortierella alpina is a well-known
producer of polyunsaturated fatty acids in the food industry. Two
series of its secondary metabolites are reported: Malpinins, a family
of amphiphilic acetylated hexapeptides, were chemically characterized
and serve as natural emulsifiers during lipid secretion. Additionally,
hydrophobic cyclopentapeptides, malpibaldins, were structurally elucidated
by NMR experiments, and their absolute stereochemistry was elucidated
through chemical derivatization and synthesis. This work highlights
lower fungi as a novel reservoir for natural products.
The psychotropic effectso fPsilocybe "magic" mushroomsa re caused by the l-tryptophan-derived alkaloid psilocybin.D espite their significance,t he secondary metabolome of these fungi is poorly understood in general. Our analysis of four Psilocybe speciesi dentified harmane, harmine, and ar ange of other l-tryptophan-derived b-carbolines as their natural products,w hichw as confirmed by 1D and 2D NMR spectroscopy.S table-isotope labeling with 13 C 11 -l-tryptophan verifiedt he b-carbolines as biosynthetic products of these fungi. In addition, MALDI-MS imaging showedt hat b-carbolines accumulate toward the hyphal apices.A sp otent inhibitors of monoamine oxidases, b-carbolines are neuroactive compounds and interfere with psilocybin degradation. Therefore, our findings represent an unprecedented scenario of natural product pathways that diverge from the same buildingb lock and produce dissimilar compounds, yet contribute directlyo ri ndirectly to the same pharmacological effects.
Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is the main alkaloid of the fungal genus Psilocybe, the so-called "magic mushrooms." The pharmaceutical interest in this psychotropic natural product as a future medication to treat depression and anxiety is strongly re-emerging. Here, we present an enhanced enzymatic route of psilocybin production by adding TrpB, the tryptophan synthase of the mushroom Psilocybe cubensis, to the reaction. We capitalized on its substrate flexibility and show psilocybin formation from 4-hydroxyindole and l-serine, which are less cost-intensive substrates, compared to the previous method. Furthermore, we show enzymatic production of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach.
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