Pterocarpans and triterpenoids from Gueldenstaedtia verna
Graphical abstract
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 (1–2) and triterpenoids (3–7) 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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