Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis

doi:10.6023/cjoc201909036

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 679-687.DOI: 10.6023/cjoc201909036 Previous Articles Next Articles

云南蕊木茎中的抗炎吲哚生物碱

解天珍^a,b, 赵云丽^b, 马伟光^c, 王易芬^b, 于浩飞^a, 王蓓^b, 魏鑫^b, 黄之镨^c, 朱培凤^b, 刘亚平^b, 罗晓东^a,b

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 发布日期:2020-04-02
通讯作者: 刘亚平, 罗晓东 E-mail:xdluo@mail.kib.ac.cn;liuyaping@mail.kib.ac.cn
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.

Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis

Xie Tian-Zhen^a,b, Zhao Yun-Li^b, Ma Wei-Guang^c, Wang Yi-Fen^b, Yu Hao-Fei^a, Wang Bei^b, Wei Xin^b, Huang Zhi-Pu^c, Zhu Pei-Feng^b, Liu Ya-Ping^b, Luo Xiao-Dong^a,b

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:2019-09-26 Revised:2019-11-02 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.

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云南蕊木茎中的抗炎吲哚生物碱

Anti-Inflammatory Indole Alkaloids from the Stems of Kopsia officinalis

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