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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

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 . Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 679 -687 . DOI: 10.6023/cjoc201909036

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