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Two previously unknown blue alkaloid pigments, sanguinone A (1) and sanguinone B (2), and one new red indoloquinone alkaloid, sanguinolentaquinone (3), have been isolated from Mycena sanguinolenta fruiting bodies. In addition, decarboxydehydrosanguinone A (4) was identified as an oxidative decarboxylation artifact of 1. The structures of these alkaloids have been established by 2D NMR and ESIMS methods. The absolute configurations of 1 and 2 were determined by comparison of their CD spectra with the CD spectrum of mycenarubin A (5), which we isolated recently from fruiting bodies of the mushroom Mycena rosea. The sanguinones are structurally related not only to the mycenarubins A (5) and B but also to a large number of marine alkaloids such as the discorhabdins.

Three new chlorinated phenols have been isolated from mycelial cultures of the mushroom Mycena alcalina. Their structures were determined by mass spectrometry and 1D and 2D NMR experiments. Addition of bromide to the medium resulted in the production of the corresponding brominated phenols. In addition, small amounts of the nonhalogenated precursor were also isolated, indicating that the halogenated metabolites are generated by a regioselectively operating halogenase.