Elsevier

Fitoterapia

Volume 106, October 2015, Pages 46-54
Fitoterapia

Pterocarpans and triterpenoids from Gueldenstaedtia verna

https://doi.org/10.1016/j.fitote.2015.07.021Get rights and content

Abstract

Two new pterocarpan glycosides (12), five new triterpenoids (37), and 13 known analogues (1420) were isolated from the whole plants of Gueldenstaedtia verna. These new compounds (17) were elucidated by extensive spectroscopic techniques including 1D (1H and 13C) and 2D NMR experiments (COSY, HSQC, HMBC and NOESY), HR-ESI-MS and chemical methods. The absolute configuration of 1 was established by the optical rotation, the comparison of experimental and calculated electronic circular dichroism (ECD) spectra and an X-ray diffraction analysis. All the isolates were evaluated for their cytotoxicities against four human cancer cell lines and inhibitory activities on LPS-induced NO production in RAW264.7 cells.

Introduction

The genus Gueldenstaedtia Fisch. (Leguminosae) comprises approximately 20 species that are mainly distributed in central and eastern Asia. Many Gueldenstaedtia species have been used in folk medicines for treatments of various inflammatory diseases [1]. Gueldenstaedtia verna (Georgi) Boriss. is a small (4–20 cm high) herbaceous perennials covered entirely with long, white pubescence, which produces violet flowers. The whole plants including roots have been used in traditional Chinese medicines (TCM) as a heat-clearing and detoxicating drug for the treatment of a wide range of discomforts, such as suppurative inflammation, furuncles, carbuncles, fever, gastroenteritis, and diarrhea. This herb shows significant antioxidant and antibacterial activities [2], [3]. It is used as a substitute for Viola yedoensis in TCM. Very little is known about the phytochemical composition of G. verna with the exception of several flavonoids [2], [3] and triterpenoids [4], [5]. As part of our ongoing investigation of the chemistry and biological activity of V. yedoensis and its substitutes [6], [7], [8], we report herein the isolation and structural elucidation of the new pterocarpans (12) and triterpenoids (37) from G. verna. Compound 1 is assigned as a rare pterocarpan ribofuranoside. All the isolates were evaluated for their cytotoxic activities against four human cancer cell lines including lung (A549), ileocecal adenocarcinoma (HCT-8), breast (MCF-7), and hepatocellular carcinoma (BEL-7402) cell lines. In addition, their inhibitory effects on lipopolysaccharides-induced NO production in RAW264.7 cells were also studied.

Section snippets

General

Optical rotations were measured at 20 °C on a Rudolph Autopol VI polarimeter (Rudolph Research Analytical, Hackettstown, NJ, USA). Electronic circular dichroism (ECD) spectra were recorded on a Chirascan CD spectrometer (Applied Photophysics Ltd., Leatherhead, UK). IR spectra were recorded on a Nicolet Avatar 360 FT-IR spectrometer (Thermo Nicolet Corporation, Madison, WI, USA) using KBr disks. NMR spectra were measured on a Bruker DRX 400 spectrometer (Bruker Daltonics, Fallanden, Switzerland).

Results and discussion

The dried and powdered whole plants of G. verna were successively extracted with 95% and 70% ethanol. The combined extract was concentrated, suspended in water, and partitioned with petroleum ether (60–90 °C), EtOAc and n-BuOH, successively. The EtOAc and n-BuOH fractions were repeatedly purified by a combination of column chromatography including silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC. A total of 8 triterpenoids and 12 flavonoids were obtained including two new pterocarpan

Conflict of interest

We wish to confirm that there are no known conflicts of interest associated with this publication and there has been no significant financial support for this work that could have influenced its outcome.

Acknowledgments

This work was supported by grants from the National Natural Science Foundation of China (No. 81473421 and No. 81073025).

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