C21 steroidal glycosides from Cynanchum paniculatum (Bunge) Kitagawa: structural elucidation and biological evaluation

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2025-08-30 DOI:10.1016/j.phytochem.2025.114661

Chunmei Sai , Xinyue Lun , Fanzhu Meng , Kangyun Jiang , Qian Deng , Huannan Wang , Jiamei Tian , Mengyue Yang , Zhen Zhang , Huiming Hua

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Abstract

Phytochemical investigation of the ethyl acetate-soluble fraction from the 95 % ethanol extract of Cynanchum paniculatum (Bunge) Kitagawa roots and rhizomes led to the isolation of eight previously undescribed C₂₁ steroidal glycosides (1–8) designated cynapanosides H–O, alongside eighteen known analogues. The structures of the compounds were elucidated by comprehensive spectroscopic analysis using HRESIMS, 1D/2D NMR, and comparison with reported data. All isolated glycosides were evaluated for cytotoxic activity against HeLa and HepG2 cell lines. Among these, cynapanoside K (4) exhibited antiproliferative effects on HeLa cells by inducing apoptosis and S-phase cell cycle arrest. Mechanistic studies revealed that 4 downregulated Bcl-2, c-Myc, and Cyclin D1 protein expression while activating Caspase-9, suggesting mitochondria-mediated apoptotic pathways contribute to its cytotoxic activity. This study expands the chemical diversity of bioactive C₂₁ steroidal glycosides and provides insights into their potential antitumor mechanisms.

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北川银杏C21甾体苷：结构解析和生物学评价

从Cynanchum paniculatum (Bunge) Kitagawa根和根茎的95%乙醇提取物中提取乙酸乙酯可溶部分进行植物化学研究，分离出8种先前未描述的C21甾体苷（1-8），指定为cynapanosides H-O，以及18种已知的类似物。化合物的结构通过HRESIMS、1D/2D NMR和与文献资料的比较进行了全面的光谱分析。所有分离的糖苷对HeLa和HepG2细胞株的细胞毒活性进行了评估。其中，cynapanoside K(4)通过诱导HeLa细胞凋亡和s期细胞周期阻滞表现出抗增殖作用。机制研究显示，4在激活Caspase-9的同时下调Bcl-2、c-Myc和Cyclin D1蛋白的表达，提示线粒体介导的凋亡途径参与了其细胞毒活性。本研究扩大了生物活性C21甾体苷的化学多样性，并为其潜在的抗肿瘤机制提供了见解。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.