Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C
| Autor: | Peter Spiteller, Robert J. R. Jaeger, Zeljka Rupcic, Jana Backenköhler, Silke Wagner, Marc Stadler, Michèle-Laure Lieunang Watat, Rieke Himstedt |
|---|---|
| Přispěvatelé: | HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. |
| Rok vydání: | 2020 |
| Předmět: |
Mycena rosea
Magnetic Resonance Spectroscopy natural products pyrroloquinolines Formaldehyde alkaloids 010402 general chemistry 01 natural sciences Biochemistry Aldehyde chemistry.chemical_compound Very Important Paper Gallic Acid Antibiosis Botany Pyrroles Fruiting Bodies Fungal Gallic acid Amino Acids Molecular Biology chemistry.chemical_classification Mushroom Molecular Structure Full Paper biology 010405 organic chemistry Alkaloid Organic Chemistry chemical ecology Full Papers biology.organism_classification 0104 chemical sciences Amino acid chemistry Inactivation Metabolic Mucorales Quinolines Molecular Medicine Agaricales Bacteria |
| Zdroj: | ChemBioChem Chembiochem |
| ISSN: | 1439-7633 1439-4227 |
| DOI: | 10.1002/cbic.201900733 |
| Popis: | Mycenarubin C, a previously unknown red pyrroloquinoline alkaloid, was isolated from fruiting bodies of the mushroom Mycena rosea and its structure was elucidated mainly by NMR spectroscopy and mass spectrometry. Unlike mycenarubin A, the major pyrroloquinoline alkaloid in fruiting bodies of M. rosea, mycenarubin C, contains an eight‐membered ring with an additional C1 unit that is hitherto unprecedented for pyrroloquinoline alkaloids known in nature. Incubation of mycenarubin A with an excess of formaldehyde revealed that mycenarubin C was generated nearly quantitatively from mycenarubin A. An investigation into the formaldehyde content of fresh fruiting bodies of M. rosea showed the presence of considerable amounts of formaldehyde, with values of 5 μg per gram of fresh weight in fresh fruiting bodies. Although mycenarubin C did not show bioactivity against selected bacteria and fungi, formaldehyde inhibits the growth of the mycoparasite Spinellus fusiger at concentrations present in fruiting bodies of M. rosea. Therefore, formaldehyde might play an ecological role in the chemical defence of M. rosea against S. fusiger. In turn, S. fusiger produces gallic acid—presumably to detoxify formaldehyde by reaction of this aldehyde with amino acids and gallic acid to Mannich adducts. Natural protection: Mycenaubin C, a pyrroloquinoline alkaloid with an unprecedented core structure, was isolated from fruiting bodies of M. rosea. The alkaloid is generated from mycenarubin A and formaldehyde. The amounts of formaldehyde present in the fruiting bodies of M. rosea exhibit a fungistatic effect against the mycoparasite S. fusiger. In turn, S. fusiger is probably able to detoxify formaldehyde with gallic acid and amino acids to Mannich adducts. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text