Anti-inflammatory sesquiterpenoid dimers from Artemisia atrovirens

Zhengguang Shao; Lizhi Li; Yongzhe Zheng; Qi Gong; Chang-Qiang Ke; Sheng Yao; Haiyan Zhang; Chunping Tang; Yang Ye

doi:10.1016/j.fitote.2022.105199

Anti-inflammatory sesquiterpenoid dimers from Artemisia atrovirens

Fitoterapia. 2022 Jun:159:105199. doi: 10.1016/j.fitote.2022.105199. Epub 2022 Apr 20.

Authors

Zhengguang Shao¹, Lizhi Li², Yongzhe Zheng¹, Qi Gong³, Chang-Qiang Ke⁴, Sheng Yao⁴, Haiyan Zhang⁵, Chunping Tang⁴, Yang Ye⁶

Affiliations

¹ State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
² State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China.
³ CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁴ State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁵ University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China; CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁶ State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China; School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China. Electronic address: yye@simm.ac.cn.

PMID: 35452745
DOI: 10.1016/j.fitote.2022.105199

Abstract

Eight new sesquiterpenoid dimers, artatrovirenolides A-H (1-8), along with three known analogues (9-11), were isolated from Artemisia atrovirens by using the LC-MS guided isolation. Compound 1 was a compound dimerized from a guaianolide and a 1,10-seco-guaianolide unit while others were from two guaianolide units. Their structures were established by comprehensive analysis of spectroscopic data, and their absolute configurations were determined by the aid of time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculation. Compound 8 showed anti-inflammatory effect in LPS-stimulated BV-2 microglial cells at 1 μM, while compounds 1, 2, 5, and 6 inhibited microglial inflammation at 10 μM.

Keywords: Artatrovirenolides A-H; Artemisia atrovirens; Guaianolide; Sesquiterpenoid dimer; TDDFT ECD calculation.

MeSH terms

Anti-Inflammatory Agents / pharmacology
Artemisia* / chemistry
Microglia
Molecular Structure
Nitric Oxide
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology

Substances

Anti-Inflammatory Agents
Sesquiterpenes
Nitric Oxide