State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China.
Phytochemistry. 2023 Oct;214:113746. doi: 10.1016/j.phytochem.2023.113746. Epub 2023 Jun 16.
Eight previously undescribed quinoline-4(1H)-one derivatives (1-8) and five known analogues (9-13) were isolated from the 95% aqueous extract of the aerial parts of Waltheria indica Linn. Their chemical structures were determined by analyzing 1D NMR, 2D NMR and HRESIMS data comprehensively. Compounds 1-8 possess diverse side chains at C-5 of quinoline-4(1H)-one or tetrahydroquinolin-4(1H)-one skeleton. The absolute configurations were assigned via comparison of the experimental and calculated ECD spectra, and analysis of the ECD data of the in situ formed [Rh(OCOCF)] complex. Additionally, all 13 isolated compounds were evaluated for their anti-inflammatory activities by measuring the inhibitory effects of nitric oxide (NO) production in lipopolysaccharide-induced BV-2 cells. Compounds 2, 5 and 11 showed moderate inhibition toward NO production with IC values of 40.41 ± 1.01, 60.09 ± 1.23 and 55.38 ± 0.52 μM, respectively.
从八角茴香的地上部分的 95%水性提取物中分离得到了 8 种以前未描述的喹啉-4(1H)-酮衍生物（1-8）和 5 种已知类似物（9-13）。通过全面分析 1D NMR、2D NMR 和 HRESIMS 数据确定了它们的化学结构。化合物 1-8 在喹啉-4(1H)-酮或四氢喹啉-4(1H)-酮骨架的 C-5 位具有不同的侧链。通过比较实验和计算的 ECD 光谱以及对原位形成的 [Rh(OCOCF)] 配合物的 ECD 数据的分析，确定了绝对构型。此外，还通过测量脂多糖诱导的 BV-2 细胞中一氧化氮（NO）产生的抑制作用来评估所有 13 种分离得到的化合物的抗炎活性。化合物 2、5 和 11 对 NO 产生表现出中等抑制作用，IC 值分别为 40.41±1.01、60.09±1.23 和 55.38±0.52μM。
