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      Preparative Separation of Six Rhynchophylla Alkaloids from Uncaria macrophylla Wall by pH-Zone Refining Counter-Current Chromatography

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          Abstract

          pH-Zone refining counter-current chromatography was successfully applied to the preparative isolation and purification of six alkaloids from the ethanol extracts of Uncaria macrophylla Wall. Because of the low content of alkaloids (about 0.2%, w/w) in U. macrophylla Wall, the target compounds were enriched by pH-zone refining counter-current chromatography using a two-phase solvent system composed of petroleum ether–ethyl acetate–isopropanol–water (2:6:3:9, v/v), adding 10 mM triethylamine in organic stationary phase and 5 mM hydrochloric acid in aqueous mobile phase. Then pH-zone refining counter-current chromatography using the other two-phase solvent system was used for final purification. Six target compounds were finally isolated and purified by following two-phase solvent system composed of methyl tert-butyl ether (MTBE)–acetonitrile–water (4:0.5:5, v/v), adding triethylamine (TEA) (10 mM) to the organic phase and HCl (5 mM) to aqueous mobile phase. The separation of 2.8 g enriched total alkaloids yielded 36 mg hirsutine, 48 mg hirsuteine, 82 mg uncarine C, 73 mg uncarine E, 163 mg rhynchophylline, and 149 mg corynoxeine, all with purities above 96% as verified by HPLC Their structures were identified by electrospray ionization-mass spectrometry (ESI-MS) and 1H-NMR spectroscopy.

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          Most cited references 26

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          Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography.

           Yoichiro Ito (2005)
          This paper aims to be an aid to those chemists who are interested in utilizing high-speed counter-current chromatography (HSCCC), which is free of irreversible adsorption and offers high resolution comparable to column chromatography. It explains the selection of HSCCC conditions step by step including the selection of two-phase solvent systems, determination of partition coefficient (K) of analytes, preparation of two-phase solvent system and sample solution, selection of elution mode, flow rate, rotation speed, and on-line monitoring of the eluate. The paper covers both standard HSCCC and pH-zone-refining CCC techniques. Technical terms (italic) unfamiliar to the beginner are comprehensively explained in Glossary. Various examples of two-phase solvent systems used in HSCCC are listed in Appendices A and B. The commercial sources of HSCCC and other CCC instruments are described in detail in the study edited by Berthod [A. Berthod (Ed.), Counter-current Chromatography, Elsevier, Amsterdam, 2003].
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            Separation of alkaloids from herbs using high-speed counter-current chromatography.

            Alkaloids represent a most widespread group of bioactive natural products. Because of their alkalinity and structural diversity, the fractionation and purification of the alkaloids from herbs can often present a number of practical difficulties using the conventional chromatographic techniques. High-speed counter-current chromatography (HSCCC) is a liquid-liquid partition chromatography with a support-free liquid stationary phase, and is gaining more and more popularity as a viable separation technique for bioactive compounds from natural resources. In the present review, focus is placed on the separation of alkaloids by both conventional HSCCC and pH-zone-refining counter-current chromatography (CCC) techniques from herbs. The review presents the separation of over 120 different alkaloid compounds from more than 30 plant species by the conventional HSCCC and pH-zone-refining CCC. Based on the data from the literature, the proper solvent systems for the separation of alkaloids by the conventional HSCCC and pH-zone-refining CCC are also summarized. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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              A Nuclear Magnetic Resonance Study on the Eleven Stereoisomers of Heteroyohimbine-Type Oxindole Alkaloids.

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                12 December 2013
                December 2013
                : 18
                : 12
                : 15490-15500
                Affiliations
                [1 ]Department of Biochemical Engineering, School of Life Science, Beijing Institute of Technology, Beijing 100081, China; E-Mail: zhqh8@ 123456163.com
                [2 ]Guizhou Academy of Testing and Analysis, Guiyang 550002, China
                [3 ]Guizhou Academy of Sciences, Guiyang 550001, China; E-Mail: linchanghu79@ 123456sina.com
                [4 ]TCM Process Control Research Center, Shandong Analysis and Test Center, Shandong Academy of Sciences, 19 Keyuan Street, Jinan 250014, China; E-Mail: wxjn1998@ 123456126.com
                Author notes
                [* ]Authors to whom correspondence should be addressed; E-Mails: duanwj@ 123456sdatc.com.cn (W.D.); bitluo@ 123456bit.edu.cn (A.L.); Tel.: +86-0531-8260-5319 (W.D.); Fax: +86-0531-8296-4889 (W.D.).
                Article
                molecules-18-15490
                10.3390/molecules181215490
                6270259
                24352009
                © 2013 by the authors; licensee MDPI, Basel, Switzerland.

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

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