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 (0.05 mg/mL) and the dandruff-associated fungi Malassezia globosa (0.39 mg/mL) and Malassezia restricta (0.55 mg/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 ∼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.

Additional Metadata
Keywords 2,7-Dimethyl-1,4-naphthoquinone, Antifungal mode of action, Antioxidant activity, Chemical-genetic profile, Chimaphila umbellata, Malassezia
Persistent URL dx.doi.org/10.1016/j.phytochem.2007.09.007
Journal Phytochemistry
Citation
Galván, I.J. (Imelda J.), Mir-Rashed, N. (Nadereh), Jessulat, M. (Matthew), Atanya, M. (Monica), Golshani, A, Durst, T. (Tony), … Smith, M. (2008). Antifungal and antioxidant activities of the phytomedicine pipsissewa, Chimaphila umbellata. Phytochemistry, 69(3), 738–746. doi:10.1016/j.phytochem.2007.09.007