High-Speed Countercurrent Chromatography

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High-Speed Countercurrent Chromatography Edited by YOICHIRO ITO Laboratory of Biophysical Chemistry National Institutes of Health Bethesda, Maryland WALTER D.

1 High-Speed Countercurrent Chromatography Edited by YOICHIRO ITO Laboratory of Biophysical Chemistry National Institutes of Health Bethesda, Maryland WALTER D. CONWAY Department of Pharmaceutics SUNY Buffalo Buffalo, New York A WILEY-INTERSCIENCE PUBLICATION JOHN WILEY & SONS New York / Chichester / Brisbane / Toronto / Singapore

2 High-Speed Countercurrent Chromatography Edited by YOICHIRO ITO Laboratory of Biophysical Chemistry National Institutes of Health Bethesda, Maryland WALTER D. CONWAY Department of Pharmaceutics SUNY Buffalo Buffalo, New York A WILEY-INTERSCIENCE PUBLICATION JOHN WILEY & SONS New York / Chichester / Brisbane / Toronto / Singapore

PREFACE CUMULATIVE LISTING OF VOLUMES IN SERIES xvii xix INSTRUMENTATION CHAPTER 1 PRINCIPLE, APPARATUS, AND METHODOLOGY OF HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 3 Yoichiro Ito 1.1. Introduction 3 1.

3 PREFACE CUMULATIVE LISTING OF VOLUMES IN SERIES xvii xix INSTRUMENTATION CHAPTER 1 PRINCIPLE, APPARATUS, AND METHODOLOGY OF HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 3 Yoichiro Ito 1.1. Introduction Principle of High-Speed Countercurrent Chromatography Two-Phase Distribution in a Rotating Coil in Unit Gravity Flow-Through Coil Planet Centrifuge Free of Rotary Seals Mechanism of High-Speed Countercurrent Chrmatography High-Speed Countercurrent Chromatograph Instrumentation Multilayer Coil Planet Centrifuge (Type J) Cross-Axis Synchronous Flow-Through Coil Planet Centrifuge Phase Distribution Diagrams Retention of Stationary Phase in Type J Coil Planet Centrifuge Retention of Stationary Phase in Cross- Axis Coil Planet Centrifuges SettlingTime General Methodology of High-Speed Countercurrent Chromatography Partition Coefficient Preparation of Sample Solution 39 vn

Vlll CONTENTS 1.5.3. Elution 1.5.4. Detection References 40 41 42 CHAPTER 2 ANALYTICAL HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY Daniel E. Schaufelberger 2.1. Introduction 2.2. Development of Analytical High-Speed Countercurrent Chromatography 2.

4 Vlll CONTENTS Elution Detection References CHAPTER 2 ANALYTICAL HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY Daniel E. Schaufelberger 2.1. Introduction 2.2. Development of Analytical High-Speed Countercurrent Chromatography 2.3. Theory 2.4. Practical Considerations Instrumentation Solvent Systems Handling Detection 2.5. Applications Methods Development Measurement of Partition Coefficients Natural Products Isolation 2.6. Discussion References SPECIAL TECHNIQUES CHAPTER 3 HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY/MASS SPECTROMETRY 73 Hisao Oka 3.1. Introduction Previous Interfacing of HSCCC With Thermospray Mass Spectrometry Direct Interfacing of HSCCC With Frit Electron Ionization, Chemical Ionization, and Fast Atom Bombardment Mass Spectrometry HSCCC/FritEIMSoflndoleAuxins HSCCC/Frit CIMS of Mycinamicins HSCCC/Frit FABMSof Colistin Complex Conclusion 90 References 90

IX CHAPTER 4 DUAL COUNTERCURRENT CHROMATOGRAPHY 93 Y. W. Lee 4.1. Introduction 93 4.2. Principles and Mechanism 94 4.3. Methods and Apparatus 95

5 IX CHAPTER 4 DUAL COUNTERCURRENT CHROMATOGRAPHY 93 Y. W. Lee 4.1. Introduction Principles and Mechanism Methods and Apparatus Applications Conclusion 104 References 104 CHAPTER 5 FOAM COUNTERCURRENT CHROMATOGRAPHY OF BACITRACIN COMPLEX 107 Hisao Oka 5.1. Introduction Apparatus of Foam Countercurrent Chromatography Previous Foam Countercurrent Chromatography Work Separation of Bacitracin Components With Nitrogen and Additive-Free Water Continuous Enrichment and Stripping of Bacitracin Components Conclusion 118 References 120 CHAPTER 6 ph-peak-focusing AND ph-zone- REFINING COUNTERCURRENT CHROMATOGRAPHY 121 Yoichiro Ito 6.1. Introduction ph-peak-focusing Countercurrent Chromatography Research for the Causative Agent Sharpening the BrAcT 3 Peak 121 Chemohydrodynamic Mechanism of ph- Peak-Focusing 126 Advanced Peak-Focusing Technique 136 Conclusion ph-zone-refining Countercurrent Chromatography 141

X CONTENTS 6.3.1. Characteristic Features of ph-zone- RefiningCCC 6.3.2. Chemohydrodynamic Mechanism of ph-zone-refining CCC 6.3.3. Simple Mathematical Model of ph- Zone-Refining CCC 6.3.4.

6 X CONTENTS Characteristic Features of ph-zone- RefiningCCC Chemohydrodynamic Mechanism of ph-zone-refining CCC Simple Mathematical Model of ph- Zone-Refining CCC Displacement ph-zone-refining CCC ph-zone-refining CCC versus Displacement Chromatography Applications of ph-zone-refining CCC Conclusion References APPLICATIONS CHAPTER 7 HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY OF NATURAL PRODUCTS 179 Marc Maillard, Andrew Marston, and Kurt Hostettmann 7.1. Introduction Instruments Solvent Systems 7.2. Preparative Applications Flavonoids Xanthones Tannins Lignans Monoterpene Glycosides Saponins Alkaloids Carotenoids Gingerols Polyacetylenic Alcohols Marine Natural Products Antibiotics 7.3. Analytical Applications Alkaloids Anthraquinones Coumarins Flavonoids

XI 7.3.5. Lignans 216 7.3.6. Macrolides 216 7.3.7. Triterpenoids 217 7.4. Conclusions 218 References 218 HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY ON MEDICINAL HERBS 225 Tian- You Zhang 8.1. Introduction 225 8.

7 XI Lignans Macrolides Triterpenoids Conclusions 218 References 218 HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY ON MEDICINAL HERBS 225 Tian- You Zhang 8.1. Introduction The Present Status of High-Speed Countercurrent Chromatography on Isolation of Medicinal Herbs Separations of Substances Prepared From Medicinal Herbs by the Horizontal Flow- Through Coil Planet Centrifuge Apparatus and Experimental Procedures Separations of a Group of Similar Substances Studies on the Preparative Capability of CPC and HPLC in the Separation of Polar Compounds Separation of Alkaloids, Hydroxyanthraquinones, and Flavonoids by Analytical HSCCC Apparatus and Experimental Procedures Separation of Alkaloids Extracted from Stephania tetranda S. Moore Separation of Hydroxyanthraquinone Derivatives Extracted from Rhubarb Rapid Separation of Flavonoids Extracted from Sea Buckthorn (Hippophae rhamnoides) Separations of Flavonoids and Alkaloids by Multilayer Coil Separator and Extractor Apparatus and Experimental Procedures 245

8.5.2. Separation of Daphne genkwa Flavonoids 247 8.5.3. Separation of Flavonoids from Crude Extracts of Sea Buckthorn (Hippophae rhamnoides) 249 8.5.4. Separation of Alkaloids from Anisodus tangulicus (Maxin) Pasch 250 8.

8 Separation of Daphne genkwa Flavonoids Separation of Flavonoids from Crude Extracts of Sea Buckthorn (Hippophae rhamnoides) Separation of Alkaloids from Anisodus tangulicus (Maxin) Pasch Semipreparative Separation of Alkaloids by GS-10A HSCCC Apparatus and Experimental Procedures Separation of Alkaloids from Sophora flavescens Ait and Datura mete L Separation of Alkaloids from Cephalotaxusfortunei Hook F Separation of Alkaloids from Senecio fuberi Hemsl Separation of Vincamine and Vincine Conclusion 262 References 263 CHAPTER 9 ISOLATION OF MARINE NATURAL PRODUCTS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 265 Nancy L. Fregeau and Kenneth L. Rinehart 9.1. Introduction Alternative Separation Techniques Countercurrent Chromatography Examples of Marine Natural Product Isolations Using High-Speed Countercurrent Chromatography Macrolides Polyethers Other Acetate-Derived Metabolites Terpenes and Steroids Peptides Nitrogen-Containing Heterocycles Conclusion 296 References 297

Xlll CHAPTER 10 SEPARATION OF COMPLICATED ANTIBIOTICS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 301 Ken-Ichi Harada 10.1. Introduction 301 10.2. Selected Antibiotics 302 10.3. Operation of HSCCC 304 10.

9 Xlll CHAPTER 10 SEPARATION OF COMPLICATED ANTIBIOTICS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 301 Ken-Ichi Harada Introduction Selected Antibiotics Operation of HSCCC Establishment of HPLC for SVD and BC Selection of Proper Two-Phase Solvent System Separation of SVD and BC Components by HSCCC Comparison of Elution Behavior of SVD and BC between HPLC and HSCCC Conclusion 317 References 318 CHAPTER 11 N-BROMOACETYL-3,3 5-TRIIODO-L- THYRONINE AND JV-BROMOACETYL-L- THYROXINE: SYNTHESIS AND CHARACTERIZATION 321 Hans J. Cahnmann Introduction Synthesis Synthesis of BrAcT Synthesis of BrAcT 4 Purification High-Speed Countercurrent Chromatography Solvents Elution Eluate Scanning Storage of HSCCC-Purified BrAcT 3 and BrAcT 4 Verification of Identity and Purity HPLC TLC Absorption Spectra in the Near UV Summary Refe rences

XIV CONTENTS CHAPTER 12 SEPARATION AND PURIFICATION OF DYES BY CONVENTIONAL HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY AND ph-zone-refining COUNTERCURRENT CHROMATOGRAPHY 337 Adrian Weisz 12.1. Introduction 337 12.

10 XIV CONTENTS CHAPTER 12 SEPARATION AND PURIFICATION OF DYES BY CONVENTIONAL HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY AND ph-zone-refining COUNTERCURRENT CHROMATOGRAPHY 337 Adrian Weisz Introduction Instrumentation Conventional HSCCC Separations Sulforhodamine B Tetrabromotetrachlorofluorescein and Phloxine B Complementary Use of HSCCC and Preparative HPLC in the Separation of a Synthetic Mixture of Dyes ph-zone-refining Countercurrent Chromatography Introduction Principle Preliminary Requirements for ph- Zone-Refining CCC Preparative Separations of Brominated and Chlorinated Fluoresceins Preparative Separations of Iodinated Fluoresceins Conclusions 381 References 382 CHAPTER 13 SEPARATION OF PROTEINS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY 385 Yoichi Shibusawa Introduction Apparatus Polymer Phase Systems for Protein Separation Countercurrent Chromatography Fractionation of Proteins PEG-Potassium Phosphate Systems PEG-Dextran Polymer Phase System Conclusion 412 References 413

XV CHAPTER 14 SEPARATION OF RARE EARTH AND CERTAIN INORGANIC ELEMENTS BY HIGH SPEED COUNTERCURRENT CHROMATOGRAPHY 415 Eiichi Kitazume 14.1. Introduction 415 14.2.

11 XV CHAPTER 14 SEPARATION OF RARE EARTH AND CERTAIN INORGANIC ELEMENTS BY HIGH SPEED COUNTERCURRENT CHROMATOGRAPHY 415 Eiichi Kitazume Introduction Separation of Rare Earth Elements by High- Speed Countercurrent Chromatography Description of the Instrument Preparation of Two-Phase Solvent and Sample Solutions Separation Procedure Measurement of Partition Coefficients K T and K E Partition Efficiencies Gradient Elution of Fourteen Rare Earth Elements Analytical Capability of High-Speed Countercurrent Chromatography for Rare Earth Elements Reproducibility of Chromatogram Quantitative Determination of Cerium Impurities in Erbium Chloride Separation of Other Inorganic Elements by High-Speed Countercurrent Chromatography Separation of Ortho-and Pyrophosphate Ions Separation of Cesium and Strontium Separation of Zirconium and Hafnium Separation of Cadmium and Zinc Separation of Nickel, Cobalt, Magnesium, and Copper Separation of Copper, Cadmium, and Manganese Separation of Iron(II) and Iron(III) Preconcentration of Trace Elements from Certain Rock Macrocomponents 438 References 441 INDEX 445

Subject Index. See for options on how to legitimately share published articles.

Subject Index. See for options on how to legitimately share published articles. 232 U.S. Food and Drug Administration, 156,184,203,218 Université de Lausanne, 143 Université de Lyon 1, 16 MODERN COUNTERCURRENT CHROMATOGRAPHY University of Illinois at Urbana- Champaign, 129 Upjohn