3,4-seco-Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus.,Journal of Agricultural and Food Chemistry

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3,4-seco-Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-02-11 , DOI: 10.1021/acs.jafc.9b06898
Wei Liu ₁ , Shengping Deng ₁ , Dexiong Zhou ₁ , Yan Huang ₁ , Chenguo Li ₁ , Lili Hao ₁ , Gaorong Zhang ₁ , Shanshan Su ₁ , Xia Xu ₁ , Ruiyun Yang ₁ , Jun Li ₁ , Xishan Huang ₁

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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 IC50 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.

中文翻译：

从青钱柳叶中分离出具有抗炎活性的 3,4-seco-达玛烷三萜皂苷。

青钱柳在我国南方常用来防治高血压、糖尿病、炎症等。尽管有关青花柳叶抗炎作用的研究已有报道，但尚未鉴定出活性抗炎化合物。本研究利用RAW 264.7细胞建立生物活性引导的鉴定模型，验证青花柳叶对炎症的抑制作用，并鉴定其抗炎成分。分离活性馏分，得到 18 个达玛烷三萜皂苷，其中包括 11 个新的 3,4-仲达玛烷三萜皂苷 (1-11)，通过核磁共振 (NMR) 波谱分析鉴定了其结构。质谱（MS）并与文献数据进行比较。化合物 7、8、10 和 11 对一氧化氮 (NO) 的产生具有很强的抑制作用，IC50 值范围为 8.23 至 11.23 μM。这四种化合物显着降低脂多糖激活的 RAW 264.7 细胞中肿瘤坏死因子-α (TNF-α)、前列腺素 E2 (PGE2) 和白细胞介素 6 (IL-6) 的分泌。此外，化合物 7 还能降低蛋白环加氧酶-2 (COX-2)、诱导型一氧化氮合酶 (iNOS) 和核因子 kappa-B (NF-κB/p65) 的表达。此外，还研究了分离物的结构-活性关系。结果表明，3,4-仲达玛烷三萜皂苷可用作潜在的抗炎药物，值得进一步研究。

更新日期：2020-02-11

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