Sesquiterpenoids from aged Artemisia argyi and their 3D-QSAR for anti-HBV activity

Yu-Ying Song; Yong-Zhi Zhou; Yun-Fen Wang; Teng-Yun Shu; Yang Feng; Min Xu; Li-Hua Su; Hai-Zhou Li

doi:10.1016/j.phytochem.2023.113912

Sesquiterpenoids from aged Artemisia argyi and their 3D-QSAR for anti-HBV activity

Phytochemistry. 2024 Jan:217:113912. doi: 10.1016/j.phytochem.2023.113912. Epub 2023 Nov 2.

Authors

Yu-Ying Song¹, Yong-Zhi Zhou², Yun-Fen Wang³, Teng-Yun Shu⁴, Yang Feng⁵, Min Xu⁶, Li-Hua Su⁷, Hai-Zhou Li⁸

Affiliations

¹ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: 20202118062@stu.kust.edu.cn.
² Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: 20212118089@stu.kust.edu.cn.
³ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: 2403271015@qq.com.
⁴ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: tengyunshu@163.com.
⁵ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: fengyang@kust.edu.cn.
⁶ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: xumin@kust.edu.cn.
⁷ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: sulh@kust.edu.cn.
⁸ Laboratory of Medicinal Chemical Biology, Facaulty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, China. Electronic address: lihaizhou@kust.edu.cn.

PMID: 37918620
DOI: 10.1016/j.phytochem.2023.113912

Abstract

Artemisia argyi Levl. Et Vant, commonly known as "Chinese Mugwort," has been utilized in traditional Chinese medicine and cuisine for centuries. Aged Chinese Mugwort has been uncovered to possess superior quality and safety, and its ethyl acetate extract has been found to exhibit anti-hepatitis B virus (HBV) activity. In this study, twenty-five sesquiterpenoids were isolated and characterized from three-year-aged A. argyi. Among them, 14 previously undescribed sesquiterpenoids (1-14), featuring double bond oxidation or ring opening. It is hypothesized that during the aging process, sesquiterpenes undergo oxidative transformation of their double bonds to form alcohols due to external factors and inherent properties. The anti-HBV activity and cytotoxicity of all compounds were assessed in vitro using HepG 2.2.15 cells, and their structure-activity relationships were analyzed through three-dimensional quantitative structure-activity relationship (3D-QASR) techniques. The α-methylene-γ-lactone sesquiterpenoid derivatives were discovered to have potent inhibitory activity against HBV. This research may broaden the potential applications of Chinese Mugwort and offer further guidance for its development and utilization as functional food or traditional Chinese medicine.

Keywords: 3D-QSAR; Anti-Hepatitis B virus; Artemisia argyi; Artemisols A–N; Compositae; Sesquiterpenoids; α-methylene-γ-lactone.

MeSH terms

Artemisia* / chemistry
Hepatitis B virus
Medicine, Chinese Traditional
Quantitative Structure-Activity Relationship
Sesquiterpenes* / pharmacology

Substances

Sesquiterpenes
methylene-lactone