Cytotoxic guaianolides and seco-guaianolides from Artemisia atrovirens

Yongzhe Zheng; Chang-Qiang Ke; Shuaizhen Zhou; Lu Feng; Chunping Tang; Yang Ye

doi:10.1016/j.fitote.2021.104900

Cytotoxic guaianolides and seco-guaianolides from Artemisia atrovirens

Fitoterapia. 2021 Jun:151:104900. doi: 10.1016/j.fitote.2021.104900. Epub 2021 Mar 26.

Authors

Yongzhe Zheng¹, Chang-Qiang Ke², Shuaizhen Zhou², Lu Feng², Chunping Tang², Yang Ye³

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.
³ 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 201210, China. Electronic address: yye@simm.ac.cn.

PMID: 33781859
DOI: 10.1016/j.fitote.2021.104900

Abstract

A phytochemical investigation of a medicinal plant Artemisia atrovirens was carried out, resulting in the characterization of a novel bis-nor seco-guaianolide, seco-atrovirenolide A (1), a new 1,10-seco-guaianolide derivative, seco-atrovirenoic acid A (2), and a new artifact 10-methanoyloxy-seco-atrovirenoic acid A (3), together with eight known guaianolide and seco-guaianolide derivatives (4-11). The structures of new compounds were fully established by extensive analysis of MS, 1D and 2D NMR spectroscopic data. The absolute configurations of the isolated compounds were confirmed by TDDFT ECD calculation, Mosher's method, and X-ray crystal diffraction experiment. All the compounds were tested in vitro for their cytotoxicity against HL-60 and A549 cell lines. Some of them showed moderate inhibitory activity against HL-60 cell lines with IC₅₀ values ranging from 5.99 to 11.74 μM.

Keywords: 1,10-seco-Guaianolide; Artemisia atrovirens; Cytotoxicity; Guaianolide; TDDFT ECD calculation.

MeSH terms

A549 Cells
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Artemisia / chemistry*
China
HL-60 Cells
Humans
Limonins / isolation & purification
Limonins / pharmacology*
Molecular Structure
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plants, Medicinal / chemistry

Substances

Antineoplastic Agents, Phytogenic
Limonins
Phytochemicals