Cynbungenins A-K, structurally diverse steroids with cytotoxic activity from the roots of Cynanchum bungei Decne

Xiao-San Li; Ming-Shang Liu; Wan-Bi Feng; Yu-Hao Luo; Wei-Bin Yuan; Ting-Ting Li; Xiao-Fu Peng; Yong-Mei Huang; Xue-Mei Yang; Hui Luo

doi:10.1016/j.phytochem.2024.114287

Cynbungenins A-K, structurally diverse steroids with cytotoxic activity from the roots of Cynanchum bungei Decne

Phytochemistry. 2025 Jan:229:114287. doi: 10.1016/j.phytochem.2024.114287. Epub 2024 Sep 12.

Authors

Affiliations

¹ Guangdong Engineering Technology Research Center for the Development and Utilization of Mangrove Wetland Medicinal Resources, Key Lab of Zhanjiang for R&D Marine Microbial Resources in the Beibu Gulf Rim, and School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, 524023, PR China; Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, and School of Pharmacy, Guangdong Medical University, Dongguan, 523808, PR China. Electronic address: [email protected].
² Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, and School of Pharmacy, Guangdong Medical University, Dongguan, 523808, PR China.
³ Guangdong Engineering Technology Research Center for the Development and Utilization of Mangrove Wetland Medicinal Resources, Key Lab of Zhanjiang for R&D Marine Microbial Resources in the Beibu Gulf Rim, and School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, 524023, PR China.
⁴ Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, and School of Pharmacy, Guangdong Medical University, Dongguan, 523808, PR China; School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, PR China.
⁵ Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, and School of Pharmacy, Guangdong Medical University, Dongguan, 523808, PR China. Electronic address: [email protected].
⁶ Guangdong Engineering Technology Research Center for the Development and Utilization of Mangrove Wetland Medicinal Resources, Key Lab of Zhanjiang for R&D Marine Microbial Resources in the Beibu Gulf Rim, and School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, 524023, PR China; Guangdong Provincial Key Laboratory of Research and Development of Natural Drugs, and School of Pharmacy, Guangdong Medical University, Dongguan, 523808, PR China. Electronic address: [email protected].

PMID: 39276823
DOI: 10.1016/j.phytochem.2024.114287

Abstract

Chemical investigation of the acid hydrolysate of Cynanchum bungei roots led to the isolation of eleven undescribed steroids, namely cynbungenins A-K (1-11), and seven previously described analogues (12-18). The complete structures of these compounds were elucidated using the comprehensive spectroscopic analyses and reference data. Structurally, compounds 1 and 2 represent the first example of androstane-type steroids found in the Cynanchum plants, and compounds 3-6 and 12 are characterized as pregnane-type steroids with a rare 8,14-seco-steroid core. In the cytotoxic activity assay, compound 16 displayed the strongest cytotoxic effect against MCF-7, HCT-116, HeLa, and HepG2 cancer cell lines, with IC₅₀ values of 9.98-16.42 μM, and further research indicated that it induced both apoptosis and cell cycle arrest in the G0/G1 phase in a dose-dependent manner toward HepG2 cells.

Keywords: Asclepiadaceae; Cynanchum bungei; Cytotoxic activity; Steroids.

MeSH terms

Antineoplastic Agents, Phytogenic* / chemistry
Antineoplastic Agents, Phytogenic* / isolation & purification
Antineoplastic Agents, Phytogenic* / pharmacology
Apoptosis* / drug effects
Cell Proliferation / drug effects
Cynanchum* / chemistry
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor*
Hep G2 Cells
Humans
Molecular Structure
Plant Roots* / chemistry
Steroids* / chemistry
Steroids* / isolation & purification
Steroids* / pharmacology
Structure-Activity Relationship

Substances

Antineoplastic Agents, Phytogenic
Steroids