Serjanic Acid Glycosides from Chenopodium hybridum L. with Good Cytotoxicity and Selectivity Profile against Several Panels of Human Cancer Cell Lines.

Karolina Grabowska,Wiesław Oleszek,Irma Podolak,Agnieszka Galanty,Łukasz Pecio,Paweł Żmudzki

doi:10.3390/molecules26164915

Abstract

Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Their effect was dose and time-dependent with varied potency, the highest against prostate PC3 and melanoma WM793, where IC50 was lower than the reference drug doxorubicin. Structure–activity relationship is briefly discussed.

Highlights

Preliminary thin-layer chromatography (TLC) comparison of methanolic extracts revealed the presence of saponins with similar chromatographic patterns in extracts from the aerial parts
Data from our experiment show that the structure of saponin influences the cytotoxicity and selectivity, but the overall effect depends mainly on the susceptibility of cells which represent a given tumor type
NMR experiments 1D (1 H NMR–500 MHz, 13 C NMR–125 MHz) and 2D (HSQC, F2 -coupled Heteronuclear Single Quantum Coherence (HSQC), H2BC, Heteronuclear Multiple Bond Correlation (HMBC), COSY, TOCSY, T-ROESY) for compound 1 were performed on a BrukerAvance III HD Ascend-500 spectrometer (Bruker BioSpin, Rheinstetten, Germany), equipped with 5 mm 1 H{109 Ag-31 P} broad-band inverse (BBI) probe; spectra were recorded in the mixture of pyridine-d5 /D2 O (250/10) with 0.2% TFA

Summary

Introduction

Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR) Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Triterpene saponins are one of the most extensively studied groups of natural metabolites that were reported to exert cytotoxicity via various mechanisms including apoptotic or non-apoptotic pathways [1] These compounds are distributed in many plant families, including Amaranthaceae, which is a source of some commercially important species like Beta vulgaris or Chenopodium quinoa. The latter is a valued crop and food product for humans and animals. Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations

Methods

Results

Conclusion