Cytotoxic 13,28 Epoxy Bridged Oleanane-Type Triterpenoid Saponins from the Roots of Ardisia crispa.

Xin Yin,Ying Zhou,Ruihang Hu,Weiqian Zhu,Yongqiang Zhou

doi:10.3390/molecules27031061

Abstract

Ardisiacrispin D–F (1–3), three new 13,28 epoxy bridged oleanane-type triterpenoid saponins, together with four known analogues (4–7) were isolated from the roots of Ardisia crispa. The structures of 1–7 were elucidated based on 1D and 2D-NMR experiments and by comparing their spectroscopic data with values from the published literatures. Ardisiacrispin D–F (1–3) are first examples that the monosaccharide directly linked to aglycone C-3 of triterpenoid saponins in genus Ardisia are non-arabinopyranose. In the present paper, all compounds are evaluated for the cytotoxicity against three cancer cell lines (HeLa, HepG2 and U87 MG) in vitro. The results show that compounds 1, 4 and 6 exhibited significant cytotoxicity against Hela and U87 MG cells with IC50 values in the range of 2.2 ± 0.6 to 9.5 ± 1.8 µM. The present investigation suggests that roots of A. crispa could be a potential source of natural anti-tumor agents and their triterpenoid saponins might be responsible for cytotoxicity.

Highlights

The genus Ardisia (Primulaceae) is widely distributed in subtropical and tropical regions of the world, and, for along time, its roots have primarily been used as traditional medicines [1]
The roots of Ardisia species appeared to be a rich source of triterpenoid saponins, which have been isolated from various Ardisia species, including A. crenata, A. crispa, A. mamillata and A. pusilla
A total of seven 13,28 epoxy bridged oleanane-type triterpenoid saponins were isolated from the roots of A. crispa and 3 of them were new structures

Summary

Introduction

The genus Ardisia (Primulaceae) is widely distributed in subtropical and tropical regions of the world, and, for along time, its roots have primarily been used as traditional medicines [1]. The chemical constituents of the genus Ardisia were reported to be saponins, isocoumarins, peptides, quinones and alkylphenols [1]. The roots of Ardisia species appeared to be a rich source of triterpenoid saponins, which have been isolated from various Ardisia species, including A. crenata, A. crispa, A. mamillata and A. pusilla. Novel triterpenoid saponins, ardisicrenosides A-B and ardisiacrispins A-B, were previously isolated from A. crenata and A. crispa, respectively [1]. Phytochemical investigations revealed that triterpenoid saponins are the main constituents of the genus Ardisia, and have significant cytotoxic activities [2,3,4,5,6,7,8]. Triterpenoid saponins reported from Ardisia plants are interesting from the viewpoints of chemical diversity and biological activity

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Results

Conclusion