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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 6.1 ) 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
Affiliation  

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Cyclocarya paliurus的叶子中分离出的具有抗炎活性的3,4-seco-Dammarane三萜皂苷。

华南Cyclocarya paliurus通常用于预防和治疗高血压,糖尿病和炎症。尽管已报道了有关C. paliurus叶片抗炎作用的研究,但尚未鉴定出活性抗炎化合物。在本研究中,RAW 264.7细胞用于建立生物活性指导的鉴定模型,以验证C. paliurus叶片对炎症的抑制作用并鉴定抗炎成分。分离出有效成分,得到18种丹玛烷三萜皂苷,其中包括11种新的3,4-seco-丹玛烷三萜皂苷(1-11),其结构是根据核磁共振(NMR)光谱和质谱(MS)并与文献数据进行比较。化合物7,8,10,11和11对一氧化氮(NO)的产生表现出强烈的抑制作用,IC50值为8.23至11.23μM。这四种化合物显着降低了脂多糖激活的RAW 264.7细胞中肿瘤坏死因子-α(TNF-α),前列腺素E2(PGE2)和白介素6(IL-6)的分泌。此外,化合物7降低了蛋白环氧合酶-2(COX-2),诱导型一氧化氮合酶(iNOS)和核因子κB(NF-κB/ p65)的表达。另外,研究了分离物的构效关系。结果表明3,4-seco-dammarane三萜皂苷可用作潜在的抗炎药,值得进一步研究。这四种化合物显着降低了脂多糖激活的RAW 264.7细胞中肿瘤坏死因子-α(TNF-α),前列腺素E2(PGE2)和白介素6(IL-6)的分泌。此外,化合物7降低了蛋白环氧合酶-2(COX-2),诱导型一氧化氮合酶(iNOS)和核因子κB(NF-κB/ p65)的表达。另外,研究了分离物的构效关系。结果表明3,4-seco-dammarane三萜皂苷可用作潜在的抗炎药,值得进一步研究。这四种化合物显着降低了脂多糖激活的RAW 264.7细胞中肿瘤坏死因子-α(TNF-α),前列腺素E2(PGE2)和白介素6(IL-6)的分泌。此外,化合物7降低了蛋白环氧合酶-2(COX-2),诱导型一氧化氮合酶(iNOS)和核因子κB(NF-κB/ p65)的表达。另外,研究了分离物的构效关系。结果表明3,4-seco-dammarane三萜皂苷可用作潜在的抗炎药,值得进一步研究。诱导型一氧化氮合酶(iNOS)和核因子κB(NF-κB/ p65)。另外,研究了分离物的构效关系。结果表明3,4-seco-dammarane三萜皂苷可用作潜在的抗炎药,值得进一步研究。诱导型一氧化氮合酶(iNOS)和核因子κB(NF-κB/ p65)。另外,研究了分离物的构效关系。结果表明3,4-seco-dammarane三萜皂苷可用作潜在的抗炎药,值得进一步研究。
更新日期:2020-02-11
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