山茱萸中1个新的裂环环烯醚萜类化合物  

A new secoiridoid from Cornus officinalis

作　　者：吴晶晶 彭中灿 赫军[1] 丁康 续洁琨 张维库[1,2] WU Jing-jing;PENG Zhong-can;HE Jun;DING Kang;XU Jie-kun;ZHANG Wei-ku(Institute of Clinical Medical Sciences&Department of Pharmacy,China-Japan Friendship Hospital,Beijing 100029,China;Chinese Academy of Medical Sciences&Peking Union Medical Cllege,Bejing 100730,China;School of Life Sciences,Beijing University of Chinese Medicine,Bejing 100029,China)

机构地区：[1]中日友好医院临床医学研究所&药学部,北京100029 [2]中国医学科学院北京协和医学院,北京100730 [3]北京中医药大学生命科学学院,北京100029

出　　处：《中国中药杂志》2024年第15期4111-4117,共7页China Journal of Chinese Materia Medica

基　　金：国家自然科学基金项目(82273809,82273815,82073731);中央高水平医院临床科研业务费成果转化项目&中日友好医院菁英计划(2023-NHLHCRF-CXYW-01,ZRJY2024-BJ01)。

摘　　要：采用大孔吸附树脂、硅胶、ODS、Sephadex LH-20和HPLC等多种技术对山茱萸化学成分进行分离纯化,综合利用HR-ESI-MS、1D和2D NMR等波谱技术鉴定化合物结构,从山茱萸水提物中分离鉴定了10个化合物,分别为(±)-cornuscone(1)、(-)-(Z)-4-hydroxy-3-methoxyphenylpropene 4-O-β-L-xylopyranosyl-(1→6)-β-D-glucopyranoside(2)、kaempferol 3-O-β-D-glucopyranoside(3)、kampferol(4)、myricetin(5)、trifolin(6)、quercetin 3-O-β-D-glucopyranoside(7)、quercetin 3-O-β-D-glucuronide-6″-methyl ester(8)、quercetin 3-O-β-D-glucuronide-6″-ethyl ester(9)、pyrogallol(10)。化合物1为新的裂环环烯醚萜类化合物,命名为(±)-cornuscone,其结构中具有少见的C-1位甲基取代。选用脂多糖(lipopolysaccharide,LPS)诱导的小鼠RAW264.7细胞模型以评价化合物的抗炎活性,结果显示化合物1的半数抑制浓度(IC_(50))为(31.15±1.29)μmol·L^(-1),表明其抗炎活性显著优于阳性药吲哚美辛[indomethacin,IC_(50)为(48.32±1.66)μmol·L^(-1)]。The chemical constituents from Cornus officinalis were isolated and purified by various techniques such as macroporous adsorption resin,silica gel,octadecylsilyl(ODS),Sephadex LH-20 column chromatography and preparative high-performance liquid chromatography(HPLC).The structures of the isolates were determined by a combination of spectroscopic techniques such as high-resolution electrospray ionization mass spectrometry(HR-ESI-MS),one-dimensional(1D)and two-dimensional(2D)nuclear magnetic resonance(NMR)spectroscopy.Ten compounds were isolated from the aqueous extract of C.officinalis and identified as(±)-cornuscone(1),(-)-(Z)-4-hydroxy-3-methoxyphenylpropene 4-O-β-L-xylopyranosyl-(1→6)-β-D-glucopyranoside(2),kaempferol 3-O-β-D-glucopyranoside(3),kampferol(4),myricetin(5),trifolin(6),quercetin 3-O-β-D-glucopyranoside(7),quercetin 3-O-β-D-glucuronide-6″-methyl ester(8),quercetin 3-O-β-D-glucuronide-6″-ethyl ester(9)and pyrogallol(10).Compound 1 is a new secoiridoid,named(±)-cornuscone with a rare methyl substitution at the C-1 position.The anti-inflammatory activity of 1 was evaluated in lipopolysaccharide(LPS)-induced RAW264.7 cells in mice.The results showed the median inhibition concentration(IC_(50))of 1 was(31.15±1.29)μmol·L^(-1),which demonstrated that the anti-inflammatory activity of 1 was significantly superior to that of indomethacin[IC_(50)value of(48.32±1.66)μmol·L^(-1)].

关 键 词：山茱萸 裂环环烯醚萜 (±)-cornuscone 抗炎 

分 类 号：R284.1[医药卫生—中药学]