Mycenaflavin A, B, C, and D: Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena haematopus. Issue 34 (25th May 2018)

• Record Type: Journal Article
• Authors: Lohmann, Julia S.; Wagner, Silke; von Nussbaum, Monika; Pulte, Anna; Steglich, Wolfgang; Spiteller, Peter
• Is Part Of: Chemistry. Volume 24:Issue 34(2018)
• Page Start: 8609
• Page End: 8614
• Publication Date: 2018-05-25
• Subjects: alkaloids -- fungi -- metabolic profiling -- natural products -- pyrroloquinolines; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201800235
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Four so far unknown pyrroloquinoline alkaloids, yellow mycenaflavins A, B, and C, and the purple mycenaflavin D, have been isolated from the fruiting bodies of Mycena haematopus . The structures of these new alkaloids were elucidated by NMR spectroscopy and HRMS (ESI + ). The mycenaflavins are structurally related to mycenarubins and haematopodins, which have been previously identified in M. haematopus . However, compared with other known fungal pyrroloquinoline alkaloids, the mycenaflavins contain an additional double bond within the pyrroloquinoline moiety that accounts for the yellow colour of the monomeric mycenaflavins A, B, and C. The purple mycenaflavin D is the first known dimeric pyrroloquinoline alkaloid with a C−C bridge between the two pyrroloquinoline units. Although the minor pyrroloquinoline alkaloid constituent mycenaflavin A exhibits only moderate bioactivity against the soil bacterium Azoarcus tolulyticus, the major pyrroloquinoline alkaloid constituent haematopodin B is similarly active as the antibiotic gentamicin. Abstract : Colour from structure : Three new yellow and one purple pyrroloquinoline alkaloids have been found in Mycena haematopus (see figure). Purple mycenaflavin D (4 ) is the first known example with a C−C bridge between the two pyrroloquinoline units. Mycenaflavin A (1 ) exhibits only moderate bioactivity against the soil bacterium Azoarcus tolulyticus, but mycenarubin D and the major pyrroloquinoline alkaloid constituent of M. haematopus, haematopodin B, is as active as the antibiotic gentamicin.