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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 C 1  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.

Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C