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2020 , Vol. 40 >Issue 3: 679 - 687

DOI: https://doi.org/10.6023/cjoc201909036

研究论文

云南蕊木茎中的抗炎吲哚生物碱

  • 解天珍 ,
  • 赵云丽 ,
  • 马伟光 ,
  • 王易芬 ,
  • 于浩飞 ,
  • 王蓓 ,
  • 魏鑫 ,
  • 黄之镨 ,
  • 朱培凤 ,
  • 刘亚平 ,
  • 罗晓东
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  • a 云南大学化学科学与工程学院药学院 教育部自然资源药物化学重点实验室 昆明 650091;
    b 中国科学院昆明植物研究所 植物化学与西部植物资源持续利用国家重点实验室 昆明 650201;
    c 云南中医药大学 昆明 650500

收稿日期: 2019-09-26

  修回日期: 2019-11-02

  网络出版日期: 2020-04-02

基金资助

云南省重大科技计划（No.2019ZF003）、国家重点研究发展计划（No.2017YFC1704007）和国家自然科学基金（Nos.31872676，31500292）资助项目.

收起

Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis

  • Xie Tian-Zhen ,
  • Zhao Yun-Li ,
  • Ma Wei-Guang ,
  • Wang Yi-Fen ,
  • Yu Hao-Fei ,
  • Wang Bei ,
  • Wei Xin ,
  • Huang Zhi-Pu ,
  • Zhu Pei-Feng ,
  • Liu Ya-Ping ,
  • Luo Xiao-Dong
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  • a Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091;
    b State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201;
    c Yunnan University of Traditional Chinese Medicine, Kunming 650500

Received date: 2019-09-26

  Revised date: 2019-11-02

  Online published: 2020-04-02

Supported by

Project supported by the Yunnan Major Science and Technology Project (No. 2019ZF003), the National Key Research and Development Program of China (No. 2017YFC1704007) and the National Natural Science Foundation of China (Nos. 31872676, 31500292).

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摘要

应用多种色谱和波谱学方法，从云南蕊木（Kopsia officinalis）茎中分离鉴定了27个单萜吲哚生物碱，包括7个新化合物kopsiofficines A～G和20个已知化合物.此外，建立脂多糖（LPS）诱导的小鼠巨噬细胞RAW 264.7炎症模型，通过测定IL-1β，PGE2和TNF-α炎症因子释放评价生物碱的抗炎活性.结果表明，kopsiofficines A（1），kopsiofficines B（2），kopsiofficines D（4），kopsiofficines F（6），kopsiofficines G（7），12-methoxykopsine（11），kopsinoline（15），（－）-N-methoxy-carbonyl-11，12-methylenedioxykopsinaline（16），kopsinine（18）和kopsinic acid（20）表现出显著的抗炎活性，与阳性对照（地塞米松）基本相当.研究发现C-5位丙酮基取代的单萜吲哚生物碱的抗炎活性明显强于原型生物碱，推测丙酮基可能是抗炎活性的药效促进基团，研究结果为进一步的结构修饰和药理学研究提供了线索.

关键词： 云南蕊木; kopsiofficines A～G; 抗炎; 单萜吲哚生物碱

本文引用格式

解天珍 , 赵云丽 , 马伟光 , 王易芬 , 于浩飞 , 王蓓 , 魏鑫 , 黄之镨 , 朱培凤 , 刘亚平 , 罗晓东 . 云南蕊木茎中的抗炎吲哚生物碱[J]. 有机化学, 2020 , 40(3) : 679 -687 . DOI: 10.6023/cjoc201909036

Abstract

Seven new monoterpenoid indole alkaloids, kopsiofficines A~G, together with twenty known alkaloids, were isolated from the stems of Kopsia officinalis. Their structures were elucidated on the basis of extensive spectroscopic methods. The anti-inflammatory activities of all alkaloids were evaluated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells by the inhibiting the production of IL-1β, PGE2 and TNF-α. Among them, kopsiofficines A (1), kopsiofficines B (2), kopsiofficines D (4), kopsiofficines F (6), kopsiofficines G (7), 12-methoxykopsine (11), kopsinoline (15), (-)-N-methoxycarbonyl-11,12-methylenedioxykopsinaline (16), kopsinine (18) and kopsinic acid (20) exhibited significant anti-inflammatory activity, which were comparable to that of dexamethasone. The results supposed that the acetonyl group at C-5 of monoterpenoid indole alkaloids play an important role in their anti-inflammatory activity.

Key words： Kopsia officinalis; kopsiofficines A～G; anti-inflammatory; monoterpenoid indole alkaloids

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