Alliacane-Type Secondary Metabolites from Submerged Cultures of the Basidiomycete <i>Clitocybe nebularis</i>
Hedda Schrey, Tarek Scheele, Conrad Ulonska, Dana Leoni Nedder, Tim Stauch, Peter Spiteller, Marc Stadler
Abstract
Seven sesquiterpenoids, named nebucanes A–G (1–7), featuring a rare alliacane scaffold with unprecedented furan or pyrrole functions, were isolated from the fermentation broth of Clitocybe nebularis. Their structures were established on the basis of 1D/2D NMR spectroscopic analyses, HR-(+)-ESIMS spectra, and comparison of measured and calculated CD spectra for determination of the absolute configuration. Assessing the biological activities, nebucane D (4) exhibited antifungal effects against Rhodotorula glutinis, while nebucane G (7) displayed significant cytotoxicity against MCF-7 and A431 cell lines.
Topics & Concepts
StereochemistryFuranTerpenoidRhodotorulaFungi imperfectiPyrroleChemistryFermentationAscomycotaCytotoxicityAntifungalSecondary metabolismSecondary metaboliteBotanyAbsolute configurationMetaboliteBiologyMicrobiologyOrganic chemistryBiochemistryYeastBiosynthesisIn vitroEnzymeGeneFungal Biology and ApplicationsMicrobial Natural Products and BiosynthesisMycorrhizal Fungi and Plant Interactions