Elsevier

Tetrahedron

Volume 72, Issue 1, 7 January 2016, Pages 134-141
Tetrahedron

Furospirostanol and spirostanol saponins from the rhizome of Tupistra chinensis and their cytotoxic and anti-inflammatory activities

https://doi.org/10.1016/j.tet.2015.11.012Get rights and content

Abstract

Five new furospirostanol saponins (15), four new spirostanol saponins (69), along with one known spirostanol saponin were isolated from the rhizome of Tupistra chinensis. The chemical structures were determined by spectroscopic and chemical methods, including IR, NMR, MS, and GC analyses. The antiproliferative effects against five human cancer cell lines were assayed for all the isolated compounds. Compounds 610 showed potent cytotoxic activities against the five cancer cell lines. The isolated compounds were evaluated the inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in a macrophage cell line RAW 264.7. Compounds 610 showed significant inhibition on NO production with IC50 values between 3.1 and 4.4 μM.

Introduction

The genus Tupistra has 12 species in southwestern China, possessing similar morphologic characteristics, and some can be substituted for each other as a folk medicine for the treatment of pharyngolaryngitis, rheumatic diseases and snake-bite.1 Previous phytochemical investigations on this genus have led to the isolation of a series of structurally diverse compounds, including steroidal sapogenins,2 saponins,3 cardenolides4 and flavans.5, 6 These components exhibit diverse biological activities, such as anti-inflammatory,7 cytotoxicity8 and anti-fungal properties.9

Tupistra chinensis is distributed in Southwest China, and its dried rhizome is a reputed folk medicine to reduce carbuncles and ameliorate pharyngitis in the Shennongjia Forest District of Hubei Province in China.10 Steroidal saponins were believed to be the main active ingredients in this plant. As part of our research project to explore more diversity bioactive leading compounds from the medicinal herbs, we investigated the 60% EtOH extract of the dried rhizome of T. chinensis and obtained five new furospirostanes (15), four new steroid saponins (69), along with one known spirostanol saponin. Herein we report the isolation and structural elucidation of these compounds and their antiproliferative activity against five human cancer cell lines, as well as the inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in a macrophage cell line RAW 264.7.

Section snippets

Structural elucidation

The 60% ethanol extract of the dried underground parts of T. chinensis was successively chromatographed on D101 macroporous resin, silica gel, ODS, and finally purified by semi-preparative HPLC to afford nine new steroidal saponins, along with one known compound. The structures of all the isolated compounds (110) (Fig. 1) were elucidated on the basis of spectroscopic data and chemical methods, including IR, NMR, MS, and GC analyses. The known compound was identified as

Conclusion

Five new furospirostanol and four new spirostanol saponins, along with one known spirostanol saponin were isolated from the rhizome of T. chinensis. The chemical structures were determined by spectroscopic and chemical methods. Compounds 15 were uncommon polyhydroxylated furospirostanol glycosides and compounds 69 were unusual spirostanol saponins with glycosidation both at C-1 and C-3 of the aglycon. Some compounds showed potent cytotoxic activities against the five cancer cell lines and

General experimental procedures

Optical rotations were measured on a JASCO P-1020 digital polarimeter. IR spectra were obtained on a PerkinElmer 100 IR spectrometer with KBr. NMR spectra were recorded on Ultrashield 500 Plus instrument and were recorded in pyridine-d5. Chemical shifts (δ) are stated in ppm from the internal standard, tetramethylsilane (TMS). HRESIMS were measured on a Waters AQUITY UPLC/Q-TOF micro spectrometer. Semi-preparative HPLC was performed on a RAININ pump equipped with a Gilson 133 refractive index

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 81573303), the Natural Science Foundation of Guangdong province (No. 2014A030313588), and the starting fund of Guangdong Pharmaceutical University. The authors were also great acknowledgments to Prof. Dr. Hao Gao, Jinan University, for his generous help in the measurement of optical rotation.

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    As a traditional Chinese medicine, Tupistra chinensis has been used in China for years. Recently, as one of the main bioactive component, the saponin of T. chinensis has been reported exhibits a strong ability to inhibit the proliferation of tumor cells [10]; however, the mechanisms of how saponin of T. chinensis induces gastric cancer cell death has not been fully elucidated. The current work was studied the most potential anti-gastric cancer compound T-17, a new spirostanol saponin, which was extracted and isolated from T. chinensis.

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