Eremophilane sesquiterpenoids from the whole plant of Parasenecio albus with immunosuppressive activity

Ming Zhou; Fangfang Duan; Ying Gao; Xiaogang Peng; Xianggao Meng; Hanli Ruan

doi:10.1016/j.bioorg.2021.105247

Eremophilane sesquiterpenoids from the whole plant of Parasenecio albus with immunosuppressive activity

Bioorg Chem. 2021 Oct:115:105247. doi: 10.1016/j.bioorg.2021.105247. Epub 2021 Aug 11.

Authors

Ming Zhou¹, Fangfang Duan², Ying Gao², Xiaogang Peng², Xianggao Meng³, Hanli Ruan⁴

Affiliations

¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China; Key Laboratory of Plant Germplasm Enhancement and Specialty Agriculture, Wuhan Botanical Garden, Chinese Academy of Sciences, Wuhan 430074, People's Republic of China.
² Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
³ College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
⁴ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: ruanhl@mails.tjmu.edu.cn.

PMID: 34411979
DOI: 10.1016/j.bioorg.2021.105247

Abstract

Fifteen new highly oxygenated eremophilane sesquiterpenoids, parasubolides A-O (1-15), were obtained from the whole plant of Parasenecio albus. The structures of 1-15 were elucidated based on the interpretation of NMR and HRESIMS data, along with experimental electronic circular dichroism (ECD) and single-crystal X-ray diffraction analysis. Compounds 1-6, and 9-14 represent the first class of 1,2,10-trioxygenated eremophilane lactones. Selected isolates were evaluated for their immunosuppressive activities. Compounds 4, 5, and 12 exhibited moderate inhibition against LPS-induced B-cell proliferation with IC₅₀ values of 23.1, 33.8, and 26.6 μM, respectively.

Keywords: Eremophilane; Immunosuppressive activity; Parasenecio albus; Sesquiterpenoids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Asteraceae / chemistry*
B-Lymphocytes / drug effects*
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Immunosuppressive Agents / chemistry
Immunosuppressive Agents / isolation & purification
Immunosuppressive Agents / pharmacology*
Lipopolysaccharides / antagonists & inhibitors
Lipopolysaccharides / pharmacology
Male
Mice
Mice, Inbred BALB C
Molecular Structure
Polycyclic Sesquiterpenes / chemistry
Polycyclic Sesquiterpenes / isolation & purification
Polycyclic Sesquiterpenes / pharmacology*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Structure-Activity Relationship

Substances

Immunosuppressive Agents
Lipopolysaccharides
Polycyclic Sesquiterpenes
Sesquiterpenes