1. 3,4- seco -Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus .
- Author
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Liu W, Deng S, Zhou D, Huang Y, Li C, Hao L, Zhang G, Su S, Xu X, Yang R, Li J, and Huang X
- Subjects
- Animals, Anti-Inflammatory Agents chemistry, Anti-Inflammatory Agents isolation & purification, Interleukin-6 genetics, Interleukin-6 immunology, Macrophages drug effects, Mice, NF-kappa B genetics, NF-kappa B immunology, Nitric Oxide Synthase Type II genetics, Nitric Oxide Synthase Type II immunology, Plant Extracts chemistry, Plant Extracts isolation & purification, Plant Leaves chemistry, RAW 264.7 Cells, Saponins chemistry, Saponins isolation & purification, Triterpenes chemistry, Triterpenes isolation & purification, Tumor Necrosis Factor-alpha genetics, Tumor Necrosis Factor-alpha immunology, Dammaranes, Anti-Inflammatory Agents pharmacology, Juglandaceae chemistry, Plant Extracts pharmacology, Saponins pharmacology, Triterpenes pharmacology
- Abstract
Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4- seco -dammarane triterpenoid saponins ( 1-11 ), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7 , 8 , 10 , and 11 showed strong inhibition on nitric oxide (NO) productions, with IC
50 values ranging from 8.23 to 11.23 μM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2 ), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure-activity relationships of the isolates were investigated. The results suggest that 3,4- seco -dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.- Published
- 2020
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