title: Antifungal and antioxidant activities of the phytomedicine pipsissewa, Chimaphila umbellata.
abstract: Bioassay-guided fractionation of Chimaphila umbellata (L.) W. Bart (Pyrolaceae) ethanol extracts led to the identification of 2,7-dimethyl-1,4-naphthoquinone (chimaphilin) as the principal antifungal component. The structure of chimaphilin was confirmed by 1H and 13C NMR spectroscopy. The antifungal activity of chimaphilin was evaluated using the microdilution method with Saccharomyces cerevisiae (0.05mg/mL) and the dandruff-associated fungi Malassezia globosa (0.39mg/mL) and Malassezia restricta (0.55mg/mL). Pronounced antioxidant activity of C. umbellata crude extract was also identified using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, suggesting this phytomedicine has an antioxidant function in wound healing. A chemical-genetic profile was completed with chimaphilin using approximately 4700 S. cerevisiae gene deletion mutants. Cellular roles of deleted genes in the most susceptible mutants and secondary assays indicate that the targets for chimaphilin include pathways involved in cell wall biogenesis and transcription.
authors.affiliation: Chemistry Department, Universidad Autónoma de Aguascalientes, Av. Universidad 940, Ags., CP 20100 México, Mexico.
authors.forename: Imelda J
authors.initials: IJ
authors.lastname: Galván
authors.forename: Nadereh
authors.initials: N
authors.lastname: Mir-Rashed
authors.forename: Matthew
authors.initials: M
authors.lastname: Jessulat
authors.forename: Monica
authors.initials: M
authors.lastname: Atanya
authors.forename: Ashkan
authors.initials: A
authors.lastname: Golshani
authors.forename: Tony
authors.initials: T
authors.lastname: Durst
authors.forename: Philippe
authors.initials: P
authors.lastname: Petit
authors.forename: Virginie Treyvaud
authors.initials: VT
authors.lastname: Amiguet
authors.forename: Teun
authors.initials: T
authors.lastname: Boekhout
authors.forename: Richard
authors.initials: R
authors.lastname: Summerbell
authors.forename: Isabel
authors.initials: I
authors.lastname: Cruz
authors.forename: John T
authors.initials: JT
authors.lastname: Arnason
authors.forename: Myron L
authors.initials: ML
authors.lastname: Smith
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D006834:Hydrazines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008290:Malassezia / Q000145:classification / Q000187:drug effects* / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010851:Picrates; D031827:Pyrolaceae / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects* / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D006834:Hydrazines; D009285:Naphthoquinones; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; C057774:chimaphilin