Cyperane-Type and Related (Nor)Sesquiterpenoids from the Root Bark of Acanthopanax gracilistylus and Their Inhibitory Effects on Nitric Oxide Production
| Autor: | Pei Xie, Tong-Hua Yang, Huai-Li Xu, Rui Zhou, Yu Zhang, Liu Shijun, Deng Chong, Yan-Ni Liang, Xu Hongbo, Zhi-Shu Tang |
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| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
Pharmaceutical Science 01 natural sciences Analytical Chemistry Nitric oxide chemistry.chemical_compound Biosynthesis Drug Discovery Pharmacology chemistry.chemical_classification biology Bicyclic molecule 010405 organic chemistry Organic Chemistry 0104 chemical sciences Nitric oxide synthase 010404 medicinal & biomolecular chemistry Complementary and alternative medicine chemistry visual_art visual_art.visual_art_medium biology.protein Molecular Medicine Bark Enantiomer Two-dimensional nuclear magnetic resonance spectroscopy Lactone |
| Zdroj: | Journal of Natural Products. 83:1453-1460 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | An enantiomeric pair of rare cyperane-type sesquiterpenoids, (+)- and (-)-gracilistones C (1a, 1b), together with a novel norsesquiterpenoid, gracilistone D (2), bearing a bicyclic lactone system were isolated from the root bark of Acanthopanax gracilistylus using LC-MS-IT-TOF analyses. The structures and absolute configurations of 1a, 1b, and 2 were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and ECD spectroscopic methods. Intermediate 1b suggests a possible biosynthesis process involving compound 2. The bioassay results showed that compounds 1a, 1b, and 2 exhibited significant inhibitory effects against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells, with IC50 values of 7.7 ± 0.6, 6.8 ± 1.5, and 2.6 ± 0.4 μM, respectively. Additional docking analyses provided some perspective of this activity in human inducible nitric oxide synthase. |
| Databáze: | OpenAIRE |
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