Diprenylated phenolic enantiomers from Artemisia scoparia

Guziliayi Kuerban; Ablajan Turak; Jiangyu Zhao; Haji Akber Aisa

doi:10.1016/j.phytochem.2024.113991

Diprenylated phenolic enantiomers from Artemisia scoparia

Phytochemistry. 2024 Mar:219:113991. doi: 10.1016/j.phytochem.2024.113991. Epub 2024 Jan 17.

Authors

Guziliayi Kuerban¹, Ablajan Turak², Jiangyu Zhao¹, Haji Akber Aisa³

Affiliations

¹ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; University of Chinese Academy of Sciences, Beijing 100049, China.
² State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China.
³ State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and the Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: haji@ms.xjb.ac.cn.

PMID: 38242272
DOI: 10.1016/j.phytochem.2024.113991

Abstract

Investigation on the chemical constituents of Artemisia scoparia resulted in the isolation of sixteen compounds, including undescribed six pairs of diprenylated phenolic enantiomers (±)-scopacoumaricin A-F, and two pairs of cis-trans isomers cis/trans-scopacoumaricin G and cis/trans-artepillin A. Trans-artepillin A was obtained from this plant for the first time. The structures of the isolates were proposed by analysis of their 1D, 2D-NMR and HRESIMS spectroscopic data. Their absolute configurations were determined by comparison of their experimental and calculated electronic circular dichroism spectra. Evaluations of the anti-inflammatory activity revealed that (-)-scopacoumaricin D, (+)-scopacoumaricin F and cis-scopacoumaricin G showed moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cell.

Keywords: Anti-inflammatory; Artemisia scoparia; Asteraceae; Enantiomer; Prenylated phenolics.

MeSH terms

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

Substances

Anti-Inflammatory Agents
Nitric Oxide