Cytotoxic triterpenoid glycosides (saikosaponins) from the roots of Bupleurum chinense

Bioorg Med Chem Lett. 2015 Sep 15;25(18):3887-92. doi: 10.1016/j.bmcl.2015.07.053.

Dan-Qi Li ¹, Jie Wu ¹, Li-Yin Liu ¹, Ying-Ying Wu ¹, Ling-Zhi Li ¹, Xiao-Xiao Huang ¹, Qing-Bo Liu ¹, Jing-Yu Yang ², Shao-Jiang Song ³, Chun-Fu Wu ⁴

Affiliations

1 School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, 103 Wenhua Rd., Shenyang 110016, People's Republic of China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
2 Department of Pharmacology, Shenyang Pharmaceutical University, 103 Wenhua Rd., Shenyang 110016, People's Republic of China.
3 School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, 103 Wenhua Rd., Shenyang 110016, People's Republic of China; Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: songsj99@163.com.
4 Department of Pharmacology, Shenyang Pharmaceutical University, 103 Wenhua Rd., Shenyang 110016, People's Republic of China. Electronic address: wucf@syphu.edu.cn.

PMID: 26259802 DOI: 10.1016/j.bmcl.2015.07.053

Abstract

As a part of our ongoing studies on cytotoxic triterpenoid saponins from herbal medicines, phytochemical investigation of the roots of Bupleurum chinense DC. afforded four new saikosaponins (1-4), along with 16 known ones (5-20). Their structures were established by direct interpretation of their spectral data, mainly HR-ESI-MS, 1D NMR and 2D NMR, and by comparison with literature data. Among them, compound 20 was isolated from the natural product for the first time. The cytotoxicities of all compounds against five selected human Cancer cell lines (A549, HepG2, Hep3B, Bcap-37 and MCF-7) were assayed. In general, a number of the isolated compounds exhibited potent cytotoxic activities against the five selected human Cancer cell lines. In particular, compounds 3, 8-9, 11-13, 16 and 20 showed more potent cytotoxic activities against the HepG2 and A549 cell lines than the positive control 5-fluorouracil. Based on the primary screening results, the preliminary structure-activity relationship (SAR) studies were also discussed. The SAR results suggest that the 13,28-epoxy bridge, the orientation of the hydroxyl group and the type of the sugar units are important requirements for cytotoxicity and selectivity.

Keywords

Bupleurum chinense DC.; Cytotoxicitie; Saikosaponins; Structure–activity relationships (SAR).

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