风轮菜中1个新的单萜
投稿时间:2023-05-14     点此下载全文
引用本文:赵迪,伍一炜,徐玉岩,范佳萍,张韵寒,杨蕊嶷,汪洪,吴丽丽,徐暾海,朱寅荻.风轮菜中1个新的单萜[J].中国现代中药,2023,25(9):1918-1924
DOI:10.13313/j.issn.1673-4890.20230514002
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作者中文名作者英文名单位中文名单位英文名E-Mail
赵迪 ZHAO Di 北京中医药大学 中药学院,北京 100029
温州医科大学 药学院,浙江 温州 325035
School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China
 
伍一炜 WU Yi-we 北京中医药大学 中药学院,北京 100029
温州医科大学 药学院,浙江 温州 325035
School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China
 
徐玉岩 XU Yu-yan 北京中医药大学 中药学院,北京 100029
温州医科大学 药学院,浙江 温州 325035
School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China
 
范佳萍 FAN Jia-ping 温州医科大学 药学院,浙江 温州 325035 School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China  
张韵寒 ZHANG Yun-han 北京中医药大学 中药学院,北京 100029 School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China  
杨蕊嶷 YANG Rui-yi 温州医科大学 药学院,浙江 温州 325035 School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China  
汪洪 WANG Hong 温州医科大学 药学院,浙江 温州 325035 School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China  
吴丽丽* WU Li-li 北京中医药大学 中医学院,北京 100029 School of Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029, China  
徐暾海 XU Tun-hai 北京中医药大学 中药学院,北京 100029 School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100029, China  
朱寅荻 ZHU Yin-di 温州医科大学 药学院,浙江 温州 325035 School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China  
基金项目:国家自然科学基金项目(81703689)
中文摘要:目的 研究风轮菜中的化学成分及生物活性。方法 运用硅胶、十八烷基硅烷键合硅胶(ODS)、Sephadex LH-20柱色谱及半制备高效液相色谱等方法,对风轮菜地上部分70%乙醇提取物的正丁醇萃取部位进行分离纯化。采用高分辨质谱、核磁共振波谱、紫外色谱、红外色谱、圆二色谱和计算圆二色谱对新化合物进行结构鉴定,核磁共振波谱和质谱鉴定已知化合物。采用棕榈酸(PA)诱导的HepG2细胞损伤模型研究化合物169的细胞保护活性。结果 从风轮菜70%乙醇提取物的正丁醇萃取部位中分离得到9个化合物,分别鉴定为 (4S,9S)-9-羟基茉莉酮(1)、红花菜豆酸(2)、环-(S-脯氨酸-R-亮氨酸)(3)、芹菜素-7-O-β-D-葡萄糖醛酸甲酯(4)、2-甲氧基-4-(2-丙烯基)-苯基-β-D-吡喃葡萄糖苷(5)、吐叶醇(6)、柚皮素-7-O-β-D-葡萄糖醛酸(7)、对-薄荷-3,8-二烯-1,2-二醇(8)、黄麻香堇醇C(9)。与模型组细胞存活率 [(63.5±2.3)%]相比,化合物9低、中、高剂量组细胞存活率[(81.0±2.0)%、(83.4±1.8)%、(90.8±2.1)%] 差异有统计学意义(P<0.001);化合物6高剂量组细胞存活率 [(72.3±2.2)%] 差异有统计学意义(P<0.05);化合物1未表现出明显活性。结论 化合物1为新化合物,化合物2~35~68系首次从风轮菜中分离得到。化合物9对PA诱导的HepG2细胞损伤具有显著的细胞保护活性,且与剂量呈正相关。化合物6在高剂量有一定的细胞保护活性。
中文关键词:风轮菜  化学成分  单萜  细胞保护
 
A New Monoterpenoid from Clinopodium chinense (Benth.) O. Kuntze
Abstract:Objective To study the chemical constituents and their biological activities in Clinopodium chinense (Benth.) O. Kuntze.Methods The chemical constituents of the 70% n-butanol extract of C. chinense were isolated and purified by column chromatography with silica gel, ODS, Sephadex LH-20, and semi-preparative high performance liquid chromatography (HPLC). High resolution mass spectrum, nuclear magnetic resonance (NMR), and ultraviolet, infrared, and circular dichroism spectroscopy were employed to identify the new compounds, and NMR and mass spectrometry were used for the structural identification of known compounds. The palmitic acid (PA)-induced injury model of HepG2 cells was used to examine the cytoprotective activities of compounds 1, 6, and 9.Results Nine chemical constituents were isolated and purified from the n-butanol extract of C. chinense and identified as (4S,9S)-9-hydroxyjasmololone (1), phaseic acid (2), cyclo-(S-Pro-R-Leu) (3), apigenin-7-O-β-D-glucuronide methyl ester (4), 2-methoxy-4-(2-propenyl)-phenyl-β-D-glucopyranoside (5), vomifoliol (6), naringenin-7-O-β-D-glucuronide (7), p-mentha-3,8-dien-1,2-diol (8), and corchoionol C (9). Compared with that [(63.5±2.3)%] in the control group (P<0.01), the survival rates of the cells treated with high-, medium-, and low-dose compound 9 increased (P<0.001), being (90.8±2.1)%, (83.4±1.8)%, and (81.0±2.0)%, respectively; the survival rate of the cells treated with high-dose compound 6 also increased (P<0.05), being (72.3±2.2)%; compound 1 did not show significant cytoprotective activity.Conclusion Compound 1 was new. Compounds 2-3, 5-6, and 8 were isolated from C. chinense for the first time. Compound 9 showed a significant protective effect on PA-induced HepG2 cell injury in a dose-dependent manner, and compound 6 at high doses showed cytoprotective activity.
keywords:Clinopodium chinense (Benth.) O. Kuntze  chemical constituents  monoterpenoid  cytoprotective activities
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