Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696
| Autor: | Karoon Sadorn, Nattawut Boonyuen, Tanapong Boonruangprapa, Pattama Pittayakhajonwut, Siriporn Saepua, Pranee Rachtawee |
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| Rok vydání: | 2017 |
| Předmět: |
Antifungal Agents
Stereochemistry Cell Survival Plasmodium falciparum Antineoplastic Agents Plant Science Fungus Horticulture 010402 general chemistry 01 natural sciences Biochemistry Antimalarials Structure-Activity Relationship Ascomycota Bacillus cereus Cell Line Tumor Chlorocebus aethiops Animals Humans Cytotoxicity Molecular Biology IC50 Vero Cells Cell Proliferation Strain (chemistry) biology Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Chemistry General Medicine biology.organism_classification Antimicrobial 0104 chemical sciences Anti-Bacterial Agents Cereus Chromones Drug Screening Assays Antitumor Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Phytochemistry. 151 |
| ISSN: | 1873-3700 |
| Popis: | Eleven previously undescribed compounds, including cytosporanthraxanthone, xanthoquinodins A7–A10, ketoxanthoquinodin A6, xanthoquinodins B6–B8, and spiroxanthoquinodins A and B, and one synthetically known compound, 2-methoxy pinselin, as well as ten known compounds, including xanthoquinodins A4−A6, B4, and B5, chrysophanol, physcion, (4S)-5-hydroxy-4-methoxy-α-tetralone, (4S)-4,8-dihydroxy-α-tetralone (or isosclerone), and gonytolide C were isolated from the fungus Cytospora eugeniae BCC42696. Their chemical structures were determined based on the analysis of NMR spectroscopic and mass spectrometric data. Moreover, the absolute configurations of the unknown compounds were established by using NOESY and NOEDIFF NMR experiments along with CD spectroscopic data. The isolated xanthoquinodins exhibited a broad range of antimalarial, antibacterial, and fungicidal activities as well as cytotoxicity. Xanthoquinodins A6, B4, and B5 showed strong activity to Plasmodium falciparum, K1 strain (IC50 0.52–0.92 μM) and displayed anti-Bacillus cereus (MIC 1.56 μg/mL). Xanthoquinodin A6 also showed anti-Curvularia lunata (MIC 3.13 μg/mL). In addition, xanthoquinodins A4, A6, B4, and B5 and ketoxanthoquinodin A6 showed cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. |
| Databáze: | OpenAIRE |
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