Monoterpenoid indole alkaloids from the stems of Kopsia officinalis

Tian-Zhen Xie; Yun-Li Zhao; Jun-Jie He; Li-Xin Zhao; Xin Wei; Ya-Ping Liu; Xiao-Dong Luo

doi:10.1016/j.fitote.2020.104547

Monoterpenoid indole alkaloids from the stems of Kopsia officinalis

Fitoterapia. 2020 Jun:143:104547. doi: 10.1016/j.fitote.2020.104547. Epub 2020 Mar 12.

Authors

Tian-Zhen Xie¹, Yun-Li Zhao¹, Jun-Jie He², Li-Xin Zhao³, Xin Wei⁴, Ya-Ping Liu⁵, Xiao-Dong Luo⁶

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.
² Lanzhou University of Technolog, Lanzhou 730050, PR China.
³ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Yunnan Institute of Food Safety, Kunming University of Science and Technology, Kunming 650500, PR China. Electronic address: [email protected].
⁶ Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China. Electronic address: [email protected].

PMID: 32173419
DOI: 10.1016/j.fitote.2020.104547

Abstract

Five new indole alkaloids, kopsiofficines H-L (1-5), along with fourteen known alkaloids (6-19) were isolated from the stems of Kopsia officinalis. Their structures were elucidated by extensive NMR, mass spectroscopic analyses and comparison to the reported data. All the isolated compounds were evaluated their anti-inflammatory activities by inhibiting IL-1β, PGE2 and TNF-α secretion in lipopolysaccharide (LPS)-activated RAW264.7 cells. Compounds 2, 3, 6, 7, 11, 12, 15, and 17 show significant anti-inflammatory activities. These results demonstrate pharmacodynamic substance basis of these folkloric claims.

Keywords: Anti-inflammatory; Indole alkaloids; Kopsia officinalis; Kopsiofficines H-L.

MeSH terms

Animals
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Apocynaceae / chemistry*
China
Mice
Molecular Structure
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Stems / chemistry*
RAW 264.7 Cells
Secologanin Tryptamine Alkaloids / isolation & purification
Secologanin Tryptamine Alkaloids / pharmacology*

Substances

Anti-Inflammatory Agents
Phytochemicals
Secologanin Tryptamine Alkaloids