Antifungal and antioxidant activities of the phytomedicine pipsissewa, Chimaphila umbellata.
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.
Galván
Imelda J
IJ
Chemistry Department, Universidad Autónoma de Aguascalientes, Av. Universidad 940, Ags., CP 20100 México, Mexico.
Mir-Rashed
Nadereh
N
Jessulat
Matthew
M
Atanya
Monica
M
Golshani
Ashkan
A
Durst
Tony
T
Petit
Philippe
P
Amiguet
Virginie Treyvaud
VT
Boekhout
Teun
T
Summerbell
Richard
R
Cruz
Isabel
I
Arnason
John T
JT
Smith
Myron L
ML
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
D000935:Antifungal Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D006834:Hydrazines; D009285:Naphthoquinones; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; C057774:chimaphilin