药学学报2024,Vol.59Issue(1) :183-187.DOI:10.16438/j.0513-4870.2023-0475

角茴香中1个新的吡嗪类生物碱

A new pyrazine from Hypecoum erectum L.

刘云 胡梦雅 张文静 范雨欣 徐瑞雯 朱登辉 孙彦君 冯卫生 陈辉
药学学报2024,Vol.59Issue(1) :183-187.DOI:10.16438/j.0513-4870.2023-0475

角茴香中1个新的吡嗪类生物碱

A new pyrazine from Hypecoum erectum L.

刘云 1胡梦雅 1张文静 1范雨欣 1徐瑞雯 1朱登辉 1孙彦君 2冯卫生 2陈辉2
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作者信息

  • 1. 河南中医药大学药学院,河南郑州 450046
  • 2. 河南中医药大学药学院,河南郑州 450046;呼吸疾病中医药防治省部共建协同创新中心,河南郑州 450046
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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(1DNMR、2DNMR、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Mo2(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50 μmol·L-1时对乙酰胆碱酯酶的抑制率分别为44.40%和43.99%.

Abstract

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 Mo2(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 50 μmol·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

Key words

Hypecoum erectum L./chemical constituent/pyrazines/hyperectpyrazin A/acetylcholinesterase inhibitory activity

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基金项目

国家自然科学基金(22177027)

出版年

2024
药学学报
中国药学会 中国医学科学院药物研究所

药学学报

CSTPCD北大核心
影响因子:1.274
ISSN:0513-4870
参考文献量13
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