M ETHODS IN MOLECULAR BIOLOGY

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1 M ETHODS IN MOLECULAR BIOLOGY Series Editor John M. Walker School of Life Sciences University of Hertfordshire Hatfield, Hertfordshire, AL10 9AB, UK For further volumes:

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3 Natural Products Isolation Third Edition Edited by Satyajit D. Sarker Department of Pharmacy, School of Applied Sciences, University of Wolverhampton, Wolverhampton, UK Lutfun Nahar Leicester School of Pharmacy, De Montfort University, The Gateway, Leicester, UK

4 Editors Satyajit D. Sarker, Ph.D. Department of Pharmacy School of Applied Sciences University of Wolverhampton Wolverhampton, UK Lutfun Nahar, Ph.D. Leicester School of Pharmacy De Montfort University Leicester, UK ISSN e-issn ISBN e-isbn DOI / Springer New York Dordrecht Heidelberg London Library of Congress Control Number: Springer Science+Business Media, LLC 2012 All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Humana Press, c/o Springer Science+Business Media, LLC, 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks, and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed on acid-free paper Humana Press is part of Springer Science+Business Media (

5 Dedication Dedicated to the memories of our dads.

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7 Preface The use of natural products for the treatment of various ailments can be traced back thousands of years, and many block-buster drugs that we use today have come from natural origins. Because of unique inherent chemical diversity, natural products have continued to be one of the major sources of new drug molecules still today. In recent years, there has been a remarkable resurgence of interests observed in the area of natural products research. With significant developments in the areas of chromatography and spectroscopy, natural products research has gained new momentum. Natural products and their analogs are now suitable for high-throughput screening, and have become part of major and meaningful drug discovery programs. Isolation of natural products is one of the main components in natural products research, especially in relation to drug discovery and development. Techniques for extraction and isolation of natural products from various matrices have evolved over the years, and particularly, over the last couple of decades, the advances in extraction and isolation technologies have made isolation of natural products less laborious and less time-consuming. The last two editions of this book captured most of the techniques that are generally used in natural products extraction and isolation. Since the publication of the second edition in 2005, there has been significant progress in these areas, which certainly demands the publication of this third edition to document new methods and technologies for natural products isolation. This thoroughly revised third edition has incorporated a total of 20 chapters; some are new chapters, while some others are expanded or updated version of the chapters from the second edition, using a slightly new lay-out and style. Chapters in this edition have included a number of hands on approaches and step-by-step protocols to help natural products researchers follow and implement these protocols in their own research. Like the previous editions, it is still our intention to provide substantial background information for budding natural product researchers as well as to offer reference guide to available methodologies and techniques for the more experienced researchers. Wolverhampton, UK Leicester, UK Satyajit D. Sarker Lutfun Nahar vii

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9 Contents Dedication Preface Contributors v vii xi 1 An Introduction to Natural Products Isolation Satyajit D. Sarker and Lutfun Nahar 2 Initial and Bulk Extraction of Natural Products Isolation Véronique Seidel 3 Supercritical Fluid Extraction in Natural Products Analyses Lutfun Nahar and Satyajit D. Sarker 4 Accelerated Solvent Extraction for Natural Products Isolation Mohammad A. Mottaleb and Satyajit D. Sarker 5 Microwave-Assisted Extraction in Natural Products Isolation Abbas Delazar, Lutfun Nahar, Sanaz Hamedeyazdan, and Satyajit D. Sarker 6 An Introduction to Planar Chromatography and Its Application to Natural Products Isolation Simon Gibbons 7 Isolation of Natural Products by Low-Pressure Column Chromatography Raymond G. Reid and Satyajit D. Sarker 8 Isolation of Natural Products by Ion-Exchange Methods Klaus Dragull and John J. Beck 9 Separation of Natural Products by Countercurrent Chromatography James B. McAlpine, J. Brent Friesen, and Guido F. Pauli 10 Isolation of Natural Products by Preparative High Performance Liquid Chromatography (Prep-HPLC) Zahid Latif and Satyajit D. Sarker 11 Isolation of Natural Products by Preparative Gas Chromatography Temel Özek and Fatih Demirci 12 Hyphenated Techniques and Their Applications in Natural Products Analysis Satyajit D. Sarker and Lutfun Nahar 13 Extraction of Plant Secondary Metabolites William P. Jones and A. Douglas Kinghorn 14 Isolation of Marine Natural Products Wael E. Houssen and Marcel Jaspars ix

10 x Contents 15 Isolation of Microbial Natural Products Olov Sterner 16 Extraction and Isolation of Saponins Runner R.T. Majinda 17 Extraction and Isolation of Phenolic Compounds Celestino Santos-Buelga, Susana Gonzalez-Manzano, Montserrat Dueñas, and Ana M. Gonzalez-Paramas 18 Scaling-Up of Natural Products Isolation Yash Kumarasamy 19 Follow-Up of Natural Products Isolation Richard J.P. Cannell, Satyajit D. Sarker, and Lutfun Nahar 20 Natural Products Isolation in Modern Drug Discovery Programs Alexander I. Gray, John O. Igoli, and RuAngelie Edrada-Ebel Index

11 Contributors JOHN J. BECK Plant Mycotoxin Research, USDA-ARS, WRRC, Albany, CA, USA RICHARD J.P. CANNELL (LATE) ABBAS DELAZAR School of Pharmacy and Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran FATIH DEMIRCI Department of Pharmacognosy, Anadolu University, Eskisehir, Turkey KLAUS DRAGULL Plant Mycotoxin Research, USDA-ARS, WRRC, Albany, CA, USA MONTSERRAT DUEÑAS Grupo de Investigación de Polifenoles (GIP-USAL), Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain RUANGELIE EDRADA-EBEL Natural Products Research Laboratories, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, UK J. BRENT FRIESEN Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA SIMON GIBBONS Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, UCL School of Pharmacy, London, UK SUSANA GONZALEZ-MANZANO Grupo de Investigación de Polifenoles (GIP-USAL), Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain ANA M. GONZALEZ-PARAMAS Grupo de Investigación de Polifenoles (GIP-USAL), Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain ALEXANDER I. GRAY Natural Products Research Laboratories, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, UK SANAZ HAMEDEYAZDAN School of Pharmacy and Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran WAEL E. HOUSSEN Department of Chemistry, Marine Biodiscovery Centre, University of Aberdeen, Old Aberdeen, UK JOHN O. IGOLI Natural Products Research Group, BCDD, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, UK MARCEL JASPARS Department of Chemistry, Marine Biodiscovery Centre, University of Aberdeen, Old Aberdeen, UK WILLIAM P. JONES Ingredient and Process Research, Kraft Foods, Glenview, IL, USA A. DOUGLAS KINGHORN Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA YASH KUMARASAMY School of Pharmacy, The Robert Gordon University, Aberdeen, UK ZAHID LATIF Technology Strategy Board, Swindon, UK RUNNER R.T. MAJINDA Department of Chemistry, University of Botswana, Gaborone, Botswana JAMES B. MCALPINE Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA xi

12 xii Contributors MOHAMMAD A. MOTTALEB Department of Chemistry/Physics, Center for Innovation and Entrepreneurship, Northwest Missouri State University, Maryville, MO, USA LUTFUN NAHAR Leicester School of Pharmacy, De Montfort University, The Gateway, Leicester, UK TEMEL ÖZEK Department of Pharmacognosy, Anadolu University, Eskisehir, Turkey GUIDO F. PAULI Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA RAYMOND G. REID School of Pharmacy, The Robert Gordon University, Aberdeen, UK CELESTINO SANTOS-BUELGA Grupo de Investigación de Polifenoles (GIP-USAL), Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain SATYAJIT D. SARKER Department of Pharmacy, School of Applied Sciences, University of Wolverhampton, Wolverhampton WV11LY, UK VÉRONIQUE SEIDEL Natural Products Research Laboratories, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow, UK OLOV STERNER Department of Chemistry, Lund University, Lund, Sweden