Minutellins A – D, azaphilones from the stromata of Annulohypoxylon minutellum (Xylariaceae). (May 2017)

• Record Type: Journal Article
• Authors: Kuhnert, Eric; Surup, Frank; Halecker, Sandra; Stadler, Marc
• Is Part Of: Phytochemistry. Volume 137(2017)
• Page Start: 66
• Page End: 71
• Publication Date: 2017-05
• Subjects: Ascomycota -- Xylariales -- Binaphthyls -- Biodiversity -- Chemotaxonomy -- Dereplication -- Polyketides; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.02.014
• Languages: English
• ISSNs: 0031-9422

Abstract

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. Compounds1, 3 and5 showed cytotoxic effects against murine and human cells. As the production of1 –5 is restricted to a group of closely related Annulohypoxylon species, they serve well as chemotaxonomic marker. Graphical abstract: Highlights: Four unprecedented azaphilones and a known binaphthyl were isolated from the fungus Annulohypoxylon minutellum. Three of the compounds exhibited cytotoxic activity against human and murine cell lines. These metabolites are chemotaxonomic markers for the genus Annulohypoxylon .