Immune-inhibitive phenyl-C1 substituent aporphine alkaloids from Thalictrum cirrhosum

Zi-Ru Yan; Zeng-Yuan Wang; Bei Wang; Pei-Feng Zhu; Xin Wei; Hao-Fei Yu; Yi-Fen Wang; Ya-Ping Liu; Wei-Lie Xiao; Xiao-Dong Luo

doi:10.1016/j.fitote.2018.05.030

Immune-inhibitive phenyl-C₁ substituent aporphine alkaloids from Thalictrum cirrhosum

Fitoterapia. 2018 Jul:128:247-252. doi: 10.1016/j.fitote.2018.05.030. Epub 2018 May 28.

Authors

Zi-Ru Yan¹, Zeng-Yuan Wang², Bei Wang³, Pei-Feng Zhu¹, Xin Wei¹, Hao-Fei Yu¹, Yi-Fen Wang³, Ya-Ping Liu³, Wei-Lie Xiao⁴, Xiao-Dong Luo⁵

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; University of Chinese Academy of Sciences, Beijing 100049, PR China.
² Yunnan Institute of Food Safety, Kunming University of Science and Technology, Kunming 6505000, 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. Electronic address: xiaoweilie@ynu.edu.cn.
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: 29852264
DOI: 10.1016/j.fitote.2018.05.030

Abstract

Five new phenyl-C₁ substituent aporphine alkaloids, 6aR-2'-methoxycarbonyl-thaliadin (1), 6aR-2'-carboxyl-thaliadin (2), 6aR-3-methoxy-hernandalinol (3), 6aS-1,3,10-trimethoxy-natalamine (4), and 3-methoxy-2'-methoxycarbonyl-oxohernandalincin (5), together with sixteen known isoquinoline alkaloids (6-21) were isolated from the whole herb of Thalictrum cirrhosum (Levl.). Their structures were elucidated by extensive spectroscopic measurements, and six isoquinoline alkaloids showed significant inhibitory activity on concanavalin A-stimulated splenocytes proliferation with IC₅₀ values 36-44 μM by the immunosuppressive bioassay.

Keywords: Aporphine alkaloids; Immune-inhibition; Thalictrum cirrhosum.

MeSH terms

Alkaloids / isolation & purification*
Animals
Aporphines / isolation & purification*
Cells, Cultured
Isoquinolines / isolation & purification*
Male
Mice
Mice, Inbred BALB C
Molecular Structure
Spleen / cytology
T-Lymphocytes / drug effects
Thalictrum / chemistry*

Substances

Alkaloids
Aporphines
Isoquinolines