Epimesatines A-I, nine undescribed prenylated flavonoids with SPHK1 inhibitory activities from Epimedium sagittatum maxim

Shuangshuang Xie; Mengnan Zeng; Jingke Zhang; Juanjuan Liu; Junjun Wei; Ru Wang; Meng Li; Zhiyou Hao; Baoyu Ji; Xiaoke Zheng; Weisheng Feng

doi:10.1016/j.phytochem.2022.113314

Epimesatines A-I, nine undescribed prenylated flavonoids with SPHK1 inhibitory activities from Epimedium sagittatum maxim

Phytochemistry. 2022 Oct:202:113314. doi: 10.1016/j.phytochem.2022.113314. Epub 2022 Jul 8.

Authors

Affiliations

¹ School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, PR China; The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou, 450046, PR China.
² School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, PR China; Co-Construction Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of PR China, Zhengzhou, 450046, PR China.
³ School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, PR China; The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou, 450046, PR China; Co-Construction Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of PR China, Zhengzhou, 450046, PR China. Electronic address: zhengxk.2006@163.com.
⁴ School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou, 450046, PR China; The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou, 450046, PR China; Co-Construction Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of PR China, Zhengzhou, 450046, PR China. Electronic address: fwsh@hactcm.edu.cn.

PMID: 35810878
DOI: 10.1016/j.phytochem.2022.113314

Abstract

Epimesatines A-I, nine undescribed prenylated flavonoids, along with ten known analogues, were isolated from the aerial parts of Epimedium sagittatum Maxim. The structures and absolute configurations of epimesatines A-I were determined using a combination of spectroscopic data, Rh₂(OCOCF₃)₄-induced electronic circular dichroism (ECD) experiments, ECD comparisons, and X-ray crystallography analysis. Epimesatines A and I displayed notable activities on the viabilities of human non-small cell lung cancer (NSCLC) A549 cells with IC₅₀ values of 1.77 and 9.97 μM, respectively. Furthermore, epimesatines A and I significantly inhibited the expression of sphingosine kinase 1 (SPHK1) in A549 cells. In addition, none of these compounds showed obvious toxicity on normal human lung bronchial epithelial BEAS-2B cells.

Keywords: Berberidaceae; Epimedium sagittatum Maxim.; Non-small cell lung cancer; Prenylated flavonoids; Sphingosine kinase 1.

MeSH terms

Carcinoma, Non-Small-Cell Lung*
Epimedium* / chemistry
Epimedium* / metabolism
Flavonoids / chemistry
Humans
Lung Neoplasms*
Phosphotransferases (Alcohol Group Acceptor)

Substances

Flavonoids
Phosphotransferases (Alcohol Group Acceptor)
sphingosine kinase