Pelianthinarubins A and B, Red Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena pelianthina

• Published in: Journal of natural products (Washington, D.C.) Vol. 79; no. 4; pp. 873 - 878
• Main Authors: Pulte, Anna, Wagner, Silke, Kogler, Herbert, Spiteller, Peter
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.04.2016; Amer Chemical Soc
• Subjects: Agaricales - chemistry; Alkaloids - chemistry; Alkaloids - isolation & purification; Betaine - analogs & derivatives; Betaine - chemistry; Chemistry, Medicinal; Fruiting Bodies, Fungal - chemistry; Germany; Histidine - analogs & derivatives; Histidine - chemistry; Life Sciences & Biomedicine; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Pyrroles - chemistry; Pyrroles - isolation & purification; Quinolines - chemistry; Quinolines - isolation & purification; Science & Technology; Germany; CHEMICAL-SHIFTS; FUNGI; SPONGE BATZELLA SP
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.5b00942

Pelianthinarubin A (1) and pelianthinarubin B (2), two previously unknown pyrroloquinoline alkaloids, have been isolated from fruiting bodies of Mycena pelianthina. The structures of these alkaloids have been deduced from their HR-(+)-ESIMS and 2D NMR data. The absolute configurations of the pelianthinarubins A (1) and B (2) were assigned by analysis of the NOE correlations and coupling constants and by comparison of the CD spectra of 1 and 2 and of hercynine obtained by degradation of 1 with suitable compounds of known absolute configuration. The pelianthinarubins A (1) and B (2), which contain an S-hercynine moiety, differ considerably from the known pyrroloquinoline alkaloids from marine organisms and other Mycena species, such as the mycenarubins, the haematopodins, and the sanguinones.