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Molecules 2016, 21(1), 10; doi:10.3390/molecules21010010

Preparative Isolation of Two Prenylated Biflavonoids from the Roots and Rhizomes of Sinopodophyllum emodi by Sephadex LH-20 Column and High-Speed Counter-Current Chromatography

1
Collaborative Innovation Center for Respiratory Disease Diagnosis and Treatment & Chinese Medicine Development of Henan Province, Henan University of Traditional Chinese Medicine, Zhengzhou 450046, Henan, China
2
School of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450046, Henan, China
3
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China
4
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, China
5
Institute of Special Animal and Plant Sciences, Chinese Academy of Agricultural Sciences, Changchun 130112, Jilin, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 5 November 2015 / Revised: 8 December 2015 / Accepted: 13 December 2015 / Published: 23 December 2015
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [1124 KB, uploaded 23 December 2015]   |  

Abstract

Two prenylated biflavonoids, podoverines B–C, were isolated from the dried roots and rhizomes of Sinopodophyllum emodi using a Sephadex LH-20 column (SLHC) and high-speed counter-current chromatography (HSCCC). The 95% ethanol extract was partitioned with ethyl acetate in water. Target compounds from the ethyl acetate fraction were further enriched and purified by the combined application of SLHC and HSCCC. n-Hexane–ethyl acetate–methanol–water (3.5:5:3.5:5, v/v) was chosen as the two phase solvent system. The flow rate of mobile phase was optimized at 2.0 mL·min−1. Finally, under optimized conditions, 13.8 mg of podoverine B and 16.2 mg of podoverine C were obtained from 200 mg of the enriched sample. The purities of podoverines B and C were 98.62% and 99.05%, respectively, as determined by HPLC. For the first time, podoverins B and C were found in the genus Sinopodophyllum. Their structures were determined by spectroscopic methods (HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC). Their absolute configurations were elucidated by comparison of their experimental and calculated ECD spectra. The cytotoxic activities were evaluated against MCF-7 and HepG2 cell lines. The separation procedures proved to be practical and economical, especially for trace prenylated biflavonoids from traditional Chinese medicine. View Full-Text
Keywords: Sinopodophyllum emodi; prenylated biflavonoid; Sephadex LH-20 column chromatography; high-speed counter-current chromatography; cytotoxic activity Sinopodophyllum emodi; prenylated biflavonoid; Sephadex LH-20 column chromatography; high-speed counter-current chromatography; cytotoxic activity
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Sun, Y.-J.; Pei, L.-X.; Wang, K.-B.; Sun, Y.-S.; Wang, J.-M.; Zhang, Y.-L.; Gao, M.-L.; Ji, B.-Y. Preparative Isolation of Two Prenylated Biflavonoids from the Roots and Rhizomes of Sinopodophyllum emodi by Sephadex LH-20 Column and High-Speed Counter-Current Chromatography. Molecules 2016, 21, 10.

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