Usnic Acid Derivatives with Cytotoxic and Antifungal Activities from the Lichen Usnea longissima
| Autor: | Ruo-yu Li, Qiang Guo, Guozhu Su, Zhong-Dong Hu, Xingyun Chai, Ailin Yang, Pengfei Tu, Zhe Wan, Chang-Hai Qu, Xuelong Yu |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Usnea
Antifungal Agents Stereochemistry Pharmaceutical Science Antineoplastic Agents Apoptosis Trichophyton rubrum 01 natural sciences Analytical Chemistry chemistry.chemical_compound Trichophyton Drug Discovery Humans IC50 Nuclear Magnetic Resonance Biomolecular Benzofurans Candida Pharmacology biology Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Organic Chemistry Usnic acid Hep G2 Cells biology.organism_classification 0104 chemical sciences Anti-Bacterial Agents 010404 medicinal & biomolecular chemistry Dose–response relationship Methotrexate Complementary and alternative medicine chemistry Molecular Medicine Two-dimensional nuclear magnetic resonance spectroscopy Drugs Chinese Herbal |
| Zdroj: | Journal of natural products. 79(5) |
| ISSN: | 1520-6025 |
| Popis: | Eight usnic acid derivatives, that is, usenamines A–F (1–6), usone (7), and isousone (8), together with the known (+)-usnic acid (9), were isolated from the lichen Usnea longissima. Their structures were elucidated using 1D and 2D NMR and MS data, and the absolute configurations of compounds 1 and 2 were defined by single-crystal X-ray diffraction analyses. Compounds 1, 2, and 8 showed inhibitory effects on the growth of human hepatoma HepG2 cells with IC50 values of 6.0–53.3 μM compared with methotrexate as the positive control, which had an IC50 value of 15.8 μM. Furthermore, 1 induced apoptosis of HepG2 cells in a dose-dependent manner at concentrations of 0–15.0 μM. The isolated compounds were also evaluated for their antifungal and antibacterial activities, with 7 and 8 exhibiting weak inhibitory effects on fungal Trichophyton rubrum spp. with an MIC value of 41.0 μM. |
| Databáze: | OpenAIRE |
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