Botanical miracles : chemistry of plants that changed the world PDF
Preview Botanical miracles : chemistry of plants that changed the world
CHEMISTRY C o o p e Botanical Miracles r | D e a k in Chemistry of Plants That Changed the World “Botanical Miracles: Chemistry of Plants That Changed the World…beautifully B makes the case for how natural products have impacted on our lives, culture and o t development. Drs. Cooper and Deakin have put together a fine and highly readable a text, and it is with great confidence that this lovely book can be recommended to n those who wish to further appreciate the magnificent contributions of plants and ic natural products to our world, health, security and comfort.” a l —Prof. Simon Gibbons, from the Foreword M As the shortcomings of purely synthetic approaches to biochemical discovery i r and development are becoming more apparent, a renaissance of interest in a the chemistry of natural products as sources for new compounds is occurring. c l A unique approach to natural products chemistry, Botanical Miracles: Chemistry e of Plants That Changed the World relates applications of plant extracts to the s historical progress of civilization. It focuses on selected plants from around the C h world, connecting their stories and properties to the development of modern e m marvels such as medicinal compounds, nutrition products, beverages, perfumes Bot anic al i s and organic pigments. Each chapter describes a particular group of plant extracts t r from various perspectives, including their chemistry, interest and value to man and y o historical background. The ends of the chapters pose challenging questions. f P l a Introducing plants that are emerging into more prominent roles in human life and n t addressing current challenges, Botanical Miracles presents a fascinating point s Miracles T of entry to the chemistry of important natural products. It examines plants and h a their extracts through the key functional groups, building blocks and concepts of t C organic chemistry. This book provides, in a single source, information and learning h a opportunities of value to a wide range of individuals involved in the fields of n g chemistry, medicine, nutrition or cosmetics whether they be students, educators, e d Chemistr y of Plants researchers or those who simply wish to extend their horizons. t h e W That Changed the World o r l d K24710 Raymond Cooper | Jeffrey John Deakin 6000 Broken Sound Parkway, NW Suite 300, Boca Raton, FL 33487 711 Third Avenue New York, NY 10017 an informa business 2 Park Square, Milton Park www.crcpress.com Abingdon, Oxon OX14 4RN, UK www.crcpress.com K24710_cover.indd 1 1/5/16 11:48 AM Botanical Miracles Chemistry of Plants That Changed the World Botanical Miracles Chemistry of Plants That Changed the World Raymond Cooper | Jeffrey John Deakin Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business Botanical Miracles Chemistry of Plants That Changed the World Raymond Cooper | Jeffrey John Deakin Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2016 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Version Date: 20151231 International Standard Book Number-13: 978-1-4987-0430-4 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmit- ted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright. com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com To John B. Stuffins An inspirational teacher and a lifelong friend to us both Contents Foreword ..................................................................................................................xv Acknowledgments ..................................................................................................xvii Authors ....................................................................................................................xix Chapter 1 Introduction ..........................................................................................1 Aims and Purpose ................................................................................1 Importance and Role of Natural Products............................................1 Organic Chemistry ...............................................................................5 A Note on the Scope ........................................................................7 A Note on Nomenclature .................................................................7 A Note on Botanical Names ............................................................7 A Note on References ......................................................................7 Chapter 2 Medical Marvels .................................................................................11 Introduction ........................................................................................11 Ancient Medicine ..........................................................................11 Central America’s Humble Potato! .....................................................13 Steroids ..........................................................................................13 Ancient Forms of Contraception ...................................................13 The Search for the Modern Birth Control Pill: The Hormones, Estrogen and Progesterone ..................................14 Isolation of Natural Diosgenin from the Mexican Yam ................15 Chemical Magic in the Laboratory: Synthesis of Norethindrone ....16 Biological Studies of Progesterone to Prevent Ovulation .............17 Medical Approval and Social Acceptance ....................................17 The Profound Social, Cultural and Economic Impacts of Reliable, Oral Contraception .........................................................18 Transformation: Global Emergence of the Yam ............................18 Hydrocarbons ................................................................................19 Saturated Hydrocarbons ................................................................19 Alkanes .....................................................................................19 Cycloalkanes .............................................................................19 Crude Oil and Industrial Fractional Distillation ...........................20 Benzene and Aromatic Compounds: Physical and Chemical Properties .......................................................................................22 Theory of the Molecular Structure of Benzene .............................23 Summary of the Characteristics of Aromatic Compounds ...........24 Europe Solves a Headache! Emergence of Aspirin ............................26 Salicin and Salicyclic Acid ............................................................26 Carboxylic Acids ...........................................................................26 Phenol and Phenolic Compounds ..................................................27 vii viii Contents Acetylation of the Hydroxyl Group of Salicylic Acid to Form Aspirin ...........................................................................................28 Attacking Malaria: A South American Treasure (but Not Gold) and a Chinese Miracle ........................................................................31 Malaria ..........................................................................................31 Cinchona ........................................................................................32 Isolation of Quinine .......................................................................32 Synthesis of Quinine in the Laboratory ........................................33 Uses of Quinine .............................................................................33 Artemisinin....................................................................................34 Carbon–Oxygen Single Bonds and Oxygen–Oxygen Single Bonds in Organic Compounds ......................................................34 The Peroxide Link and the Peroxide Bridge in Artemisinin.........36 A Steroid in Your Garden ...................................................................38 The Foxglove and Digoxigenin .....................................................38 Esters Are Formed from Alcohols and Acids ...............................40 Properties and Uses of Esters ........................................................41 Introducing Cyclic Esters Known as Lactones..............................42 Lactones as Building Blocks in Nature .........................................42 Vitamins ........................................................................................42 Vitamin C, Ascorbic Acid .............................................................43 Commercial Uses of Lactones .......................................................44 Africa’s Gift to the World ...................................................................46 Discovery of the Periwinkle Plant and Its Properties ...................46 Serendipity .....................................................................................47 Angela’s Story ................................................................................48 Modern Research and Therapeutic Value .....................................48 The Alkaloids, Vincristine and Vinblastine ..................................49 Isolation of Vincristine and Vinblastine from Plants ....................50 Fractional Distillation ...............................................................50 Acid–Base Extraction ...............................................................50 Saving the Pacific Yew Tree ...............................................................52 The Nature of Paclitaxel ................................................................52 Medical Value of Paclitaxel ...........................................................53 Modern-Day Preparation of Paclitaxel ..........................................53 Terpenes and Isoprene as a Building Block in Nature ..................53 Isomers ..........................................................................................54 Isomers and Stereochemistry ........................................................54 Isomers and Chirality ....................................................................55 Nuclear Magnetic Resonance (NMR) Spectroscopy and Molecular Structure .......................................................................56 Chapter 3 Modern Miracles of Foods and Ancient Grains .................................59 Introduction ........................................................................................59 Rediscovering Traditional Grains of the Americas: Chia and Quinoa ....60
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