title: Minutellins A - D, azaphilones from the stromata of Annulohypoxylon minutellum (Xylariaceae).
abstract: During the course of our screening for new metabolites with chemotaxonomic importance from stromata of fungi from the family Xylariaceae, we characterized several interesting metabolites in the fungus Annulohypoxylon minutellum. Extraction of the fruiting bodies and purification by preparative HPLC resulted in the isolation of five metabolites. The main compound was identified as the known metabolite hinnulin A (5), while four minor compounds were found to represent previously undescribed azaphilones, named minutellins A - D (1-4). Their planar structures were elucidated using NMR and HRESIMS data; absolute stereochemistry was assigned by CD data and Mosher's method. Compounds 1, 3 and 5 showed cytotoxic effects against murine and human cells. As the production of 1-5 is restricted to a group of closely related Annulohypoxylon species, they serve well as chemotaxonomic marker.
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Eric
authors.initials: E
authors.lastname: Kuhnert
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Surup
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany.
authors.forename: Sandra
authors.initials: S
authors.lastname: Halecker
authors.affiliation: Helmholtz Centre for Infection Research GmbH (HZI), Department Microbial Drugs, Inhoffenstraße 7, 38124 Braunschweig, Germany; German Centre for Infection Research Association (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany. Electronic address: marc.stadler@helmholtz-hzi.de.
authors.forename: Marc
authors.initials: M
authors.lastname: Stadler
mesh_terms: D000818:Animals; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D048690:Fruiting Bodies, Fungal / Q000737:chemistry; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D010860:Pigments, Biological / Q000737:chemistry* / Q000302:isolation & purification; D013098:Xylariales / Q000737:chemistry*
chemical_list: D001578:Benzopyrans; D010860:Pigments, Biological; C494154:azaphilone
keywords: Ascomycota; Binaphthyls; Biodiversity; Chemotaxonomy; Dereplication; Polyketides; Xylariales