Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim

doi:10.1007/s13659-025-00510-1

Natural Products and Bioprospecting ›› 2025, Vol. 15 ›› Issue (4): 31-31.DOI: 10.1007/s13659-025-00510-1

Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim

Shuang-Shuang Xie^1,2, Xiang Yu^1,2, Qi-Mei Tie^1,2, Jing-Ke Zhang^1,2, Bei-Bei Zhang^1,2, Meng-Nan Zeng^1,2, Xiao-Ke Zheng^1,2, Wei-Sheng Feng^1,2

1. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, People's Republic of China;
2. The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou, 450046, People's Republic of China

Received:2025-02-16 Accepted:2025-04-01 Online:2025-05-13 Published:2025-08-23
Supported by:
This work was financially supported by the National Natural Science Foundation of China (No. 32200319); Postdoctoral Research Grant in Henan Province (No. 202102073); The National Key Research and Development Project (The Major Project for Research of the Modernization of TCM) (No. 2019YFC1708800); and the Central Leading Local Science and Technology Development Special Foundation ([2016]149).

Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim

Shuang-Shuang Xie^1,2, Xiang Yu^1,2, Qi-Mei Tie^1,2, Jing-Ke Zhang^1,2, Bei-Bei Zhang^1,2, Meng-Nan Zeng^1,2, Xiao-Ke Zheng^1,2, Wei-Sheng Feng^1,2

1. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, People's Republic of China;
2. The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou, 450046, People's Republic of China

通讯作者: Wei-Sheng Feng, E-mail:fwsh@hactcm.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (No. 32200319); Postdoctoral Research Grant in Henan Province (No. 202102073); The National Key Research and Development Project (The Major Project for Research of the Modernization of TCM) (No. 2019YFC1708800); and the Central Leading Local Science and Technology Development Special Foundation ([2016]149).

Abstract

Abstract: In this work, six pairs of undescribed enantiomeric prenylated flavonoids, ( ±)-epimesatines J–O (1a/1b–6a/6b), were isolated from the aerial parts of Epimedium sagittatum Maxim. Their structures and absolute configurations were determined based on spectroscopic data, quantum chemical calculations of electronic circular dichroism (ECD) and ¹³C NMR, as well as ECD experiments induced by Mo₂(OAc)₄ and Rh₂(OCOCF₃)₄. The cytotoxicity assay revealed that compounds 1a/1b, 2a/2b, and 4a/4b–6a/6b demonstrated significant inhibitory effects on the viability of human breast cancer cells MCF-7 while exhibiting no obvious toxicity towards human breast epithelial cells MCF-10A. Additionally, these compounds were found to decrease the expression of sphingosine kinase 1 (Sphk1) in MCF-7 cells. Notably, compounds 4a and 5b exhibited IC₅₀ values of 7.45 and 8.97 μM, respectively, in MCF-7 cells.

Key words: Epimedium sagittatum Maxim, Enantiomeric prenylated flavonoids, ECD, Cytotoxicity, Sphk1

摘要： In this work, six pairs of undescribed enantiomeric prenylated flavonoids, ( ±)-epimesatines J–O (1a/1b–6a/6b), were isolated from the aerial parts of Epimedium sagittatum Maxim. Their structures and absolute configurations were determined based on spectroscopic data, quantum chemical calculations of electronic circular dichroism (ECD) and ¹³C NMR, as well as ECD experiments induced by Mo₂(OAc)₄ and Rh₂(OCOCF₃)₄. The cytotoxicity assay revealed that compounds 1a/1b, 2a/2b, and 4a/4b–6a/6b demonstrated significant inhibitory effects on the viability of human breast cancer cells MCF-7 while exhibiting no obvious toxicity towards human breast epithelial cells MCF-10A. Additionally, these compounds were found to decrease the expression of sphingosine kinase 1 (Sphk1) in MCF-7 cells. Notably, compounds 4a and 5b exhibited IC₅₀ values of 7.45 and 8.97 μM, respectively, in MCF-7 cells.

关键词: Epimedium sagittatum Maxim, Enantiomeric prenylated flavonoids, ECD, Cytotoxicity, Sphk1

Shuang-Shuang Xie, Xiang Yu, Qi-Mei Tie, Jing-Ke Zhang, Bei-Bei Zhang, Meng-Nan Zeng, Xiao-Ke Zheng, Wei-Sheng Feng. Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim[J]. Natural Products and Bioprospecting, 2025, 15(4): 31-31.

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Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim

Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim

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