Sanguinones A and B, blue pyrroloquinoline alkaloids from the fruiting bodies of the mushroom Mycena sanguinolenta.
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.
Peters
Silke
S
Institut für Organische Chemie und Biochemie II der Technischen Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Spiteller
Peter
P
D000363:Agaricales / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D048690:Fruiting Bodies, Fungal / Q000737:chemistry*; D005858:Germany; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification
D000470:Alkaloids; D026121:Indole Alkaloids; D011758:Pyrroles; D011809:Quinones; C522949:sanguinolentaquinone; C522947:sanguinone A; C522948:sanguinone B