Racemic immunosuppressive seco-aporphine derivatives from Thalictrum wangii

Qiong Jin; Xin Wei; Xu-Jie Qin; Fei Gao; Pei-Feng Zhu; Hai-Lian Yuan; Guy Sedar Singor Njateng; Zhi Dai; Ya-Ping Liu; Xiao-Dong Luo

doi:10.1016/j.fitote.2019.104445

Racemic immunosuppressive seco-aporphine derivatives from Thalictrum wangii

Fitoterapia. 2020 Jan:140:104445. doi: 10.1016/j.fitote.2019.104445. Epub 2019 Nov 30.

Authors

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; 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.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Guizhou University of Traditional Chinese Medicine, Guiyang 550025, PR China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.
⁴ 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.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; 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. Electronic address: xdluo@mail.kib.ac.cn.

PMID: 31790771
DOI: 10.1016/j.fitote.2019.104445

Abstract

Thallactones A (1) and B (2), enantiomeric aporphine alkaloids with rare cleaved rings A and B, as well as thaliglucine N-oxide (3) and their biosynthetically related precursor, northalphenine (4), were isolated from the whole plant of Thalictrum wangii. Their structures with absolute configurations were elucidated by spectral techniques and electronic circular dichroism (ECD). Moreover, compounds 1, 3, and northalphenine inhibited concanavalin A (Con A)-stimulated proliferation of mice splenocyte significantly in a dose-dependent manner.

Keywords: Immunosuppressive bioactivity; Thalictrum wangii; seco-aporphine derivatives.

MeSH terms

Animals
Aporphines / isolation & purification
Aporphines / pharmacology*
China
Dose-Response Relationship, Drug
Immunosuppressive Agents / isolation & purification
Immunosuppressive Agents / pharmacology*
Mice
Molecular Structure
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Spleen / cytology
Spleen / drug effects
Stereoisomerism
Thalictrum / chemistry*

Substances

Aporphines
Immunosuppressive Agents
Phytochemicals
aporphine