title: Acetophenone derivatives from a freshwater fungal isolate of recently described Lindgomyces madisonensis (G416).
abstract: The exploration of freshwater ascomycetes, which have undergone only limited investigation, may provide opportunities both to characterize new genera/species of fungi and to uncover new chemical diversity. In this study, seven acetophenone derivatives, madisone, 4'-methoxymadisone, dehydromadisone, 2″-methoxymadisone, dihydroallovisnaginone, dimadisone, and 4'-methoxydimadisone were characterized from an organic extract of a recently described Lindgomyces madisonensis (G416) culture, which was isolated from submerged wood collected in a stream in North Carolina. Madisone, dehydromadisone, 2″-methoxymadisone, dimadisone and 4'-demethoxydimadisone have not been reported previously, while 4'-methoxymadisone and dihydroallovisnaginone were previously unknown as natural products. Their structures were assigned on the basis of NMR and HRESIMS data, with the structure of madisone supported by X-ray crystallography. The antimicrobial activities of madisone, 4'-methoxymadisone and dihydroallovisnaginone were evaluated against a panel of bacteria and fungi. A heat map analysis of the surface of a G416 culture showed that most of the isolated compounds concentrated in the guttate compared with the vegetative mycelium of the fungus.
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Patricia A. Sullivan Science Building, PO Box 26170, Greensboro, NC 27402-6170, USA.
authors.forename: Noemi D
authors.initials: ND
authors.lastname: Paguigan
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Patricia A. Sullivan Science Building, PO Box 26170, Greensboro, NC 27402-6170, USA.
authors.forename: Huzefa A
authors.initials: HA
authors.lastname: Raja
authors.affiliation: Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109, USA.
authors.forename: Cynthia S
authors.initials: CS
authors.lastname: Day
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Patricia A. Sullivan Science Building, PO Box 26170, Greensboro, NC 27402-6170, USA. Electronic address: nicholas_oberlies@uncg.edu.
authors.forename: Nicholas H
authors.initials: NH
authors.lastname: Oberlies
mesh_terms: D000098:Acetophenones / Q000737:chemistry / Q000302:isolation & purification*; D001203:Ascomycota / Q000737:chemistry*; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D018360:Crystallography, X-Ray; D004926:Escherichia coli / Q000187:drug effects; D005618:Fresh Water; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects; D009657:North Carolina; D019906:Nuclear Magnetic Resonance, Biomolecular; D010802:Phylogeny; D013172:Spores, Fungal; D013211:Staphylococcus aureus / Q000187:drug effects; D014934:Wood / Q000382:microbiology
chemical_list: D000098:Acetophenones; C038699:acetophenone
keywords: Acetophenones; Freshwater ascomycetes; Lindgomyces madisonensis; Submerged wood