角茴香中1个新的吡嗪类生物碱  

A new pyrazine from Hypecoum erectum L.

作　　者：刘云 胡梦雅 张文静 范雨欣 徐瑞雯 朱登辉 孙彦君[1,2] 冯卫生 陈辉[1,2] LIU Yun;HU Meng-ya;ZHANG Wen-jing;FAN Yu-xin;XU Rui-wen;ZHU Deng-hui;SUN Yan-jun;FENG Wei-sheng;CHEN Hui(School of Pharmacy,Henan University of Chinese Medicine,Zhengzhou 450046,China;Co-construction of Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan&Education Ministry of China,Zhengzhou 450046,China)

机构地区：[1]河南中医药大学药学院,河南郑州450046 [2]呼吸疾病中医药防治省部共建协同创新中心,河南郑州450046

出　　处：《药学学报》2024年第1期183-187,共5页Acta Pharmaceutica Sinica

基　　金：国家自然科学基金资助项目(22177027)。

摘　　要：采用硅胶、ODS、MCI等柱色谱以及半制备液相等现代色谱分离技术对角茴香(Hypecoum erectum L.)正丁醇萃取部位的化学成分进行分离纯化,得到4个吡嗪类生物碱。运用现代波谱学方法(1D NMR、2D NMR、UV、IR、MS等)鉴定结构分别为hyperectpyrazin A(1)、1′S-(6-methylpyrazin-2-yl)-ethane-1′,2′-diol(2)、2-hydroxymethyl-6-methylpyrazin(3)和pyrazine-2-carboxylic acid(4)。化合物1为1个新的吡嗪类生物碱,化合物2~4为首次从角茴香中分离得到,并首次通过Mo_(2)(OAc)_(4)诱导的CD谱确定了化合物2的绝对构型。采用乙酰胆碱酯酶抑制模型和脂多糖诱导的RAW264.7巨噬细胞炎症模型,对化合物1~4进行体外活性评价,其中化合物2和4表现出一定的乙酰胆碱酯酶抑制活性,在终浓度为50μmol·L^(-1)时对乙酰胆碱酯酶的抑制率分别为44.40%和43.99%。Four pyrazines were isolated from the n-butanol fraction of Hypecoum erectum L.by using various chromatographic methods,including MCI gel,ODS,silica gel and semi-preparative HPLC.The structures of the isolated compounds were identified as hyperectpyrazin A(1),1′S-(6-methylpyrazin-2-yl)-ethane-1′,2′-diol(2),2-hydroxymethyl-6-methylpyrazin(3)and pyrazine-2-carboxylic acid(4)by spectroscopy methods(1D NMR,2D NMR,UV,IR,MS,etc.).The absolute configuration of compound 2 was determined by using the Mo_(2)(OAc)_(4) induced CD analysis for the first time.Compound 1 was a new compound,compounds 2-4 were isolated from H.erectum for the first time.Compounds 1−4 were evaluated for their inhibition against acetylcholinesterase and nitric oxide generation induced by lipopolysaccharide-RAW264.7 macrophage cells.At a concentration of 50μmol·L^(-1),compounds 2 and 4 displayed inhibitory effects on acetylcholinesterase with the inhibition rates of 44.40%and 43.99%,respectively.

关 键 词：角茴香 化学成分 吡嗪类生物碱 hyperectpyrazin A 乙酰胆碱酯酶抑制活性 

分 类 号：R284[医药卫生—中药学]