Overview

An exploration of the critical role of plant-derived natural products in the discovery and development of pharmaceutical agents Illustrated throughout with a rich collection of rare and historical images, Medicinal Chemistry of Plant-Derived Natural Products provides a complete overview of the role of plants in drug discovery and development. Divided into five parts on carbohydrates, polyphenols, terpenes, steroids, and alkaloids, this book contains a wealth of primary information and references, including seminal publications and contemporary reviews. Medicinal Chemistry of Plant-Derived Natural Products includes essential information covering: Antidiabetic agents and sources such as glycosides, type-II antidiabetic agents, phlorizin and related gliflozins Antitumor agents and sources including anthraquinone glycosides, podophyllum and related antitumor agents, taxanes: paclitaxel, docetaxel, and cabazitaxel, flavones and cyclin dependent-kinase (CDKs) inhibitors, triterpenes and saponins, antitumor vinca alkaloids Antimalarials such as artemisia, artemisinin and related agents Natural products and derivatives including polyphenols, balsams and oils, coumarins, chromones and furochromones, cannabis and cannabinoids Alkaloids and related drugs such as ephedra and adrenergic drugs, piperidine and pyridine alkaloids, colchicine, tropane alkaloids, atropine and anticholinergic drugs, amaryllidaceae alkaloids, galantamine, indole alkaloids, physostigmine and related carbamates Ideal for students, graduates, and researchers in academia and industry, Medicinal Chemistry of Plant-Derived Natural Products offers invaluable insights into the journey of transforming plants into pharmaceuticals.

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Author:   Enrique Ravina (University of Santiago de Compostela, Spain)
Publisher:   Wiley-VCH Verlag GmbH
Imprint:   Blackwell Verlag GmbH
ISBN:  

9783527354948

ISBN 10:   3527354948
Pages:   560
Publication Date:   10 June 2026
Audience:   College/higher education ,  Professional and scholarly ,  Tertiary & Higher Education ,  Professional & Vocational
Format:   Hardback
Publisher's Status:   Active
Availability:   Awaiting stock  
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Table of Contents

Foreword xvii Preface xxi Introduction & Historical Background xxxi Part I Carbohydrates and Natural Products related to Carbohydrates 1 1 Carbohydrates 3 1.1 Polisaccarides 3 1.1.1 Gums and Mucilages 3 1.1.2 Mucilages 6 1.2 Carbohydrates as Antidiabetic Agents 6 1.2.1 α-Glucosidase Inhibitors in Diabetes 6 A Appendix to Chapter 1 7 A.1 Non-Carbohydrates as Antidiabetic Agents 7 A.2 Type-II Antidiabetic Agents 9 A.3 Biguanides 12 2 Natural Products Related to Carbohydrates 15 2.1 Glycosides 15 2.1.1 Introduction 15 2.2 Anthraquinone Glycoside as Laxatives 16 2.3 Phenol Glycosides 19 2.3.1 Phlorizin 19 2.4 Novel Strategy in the Treatment of Type-2 Diabetes 21 2.4.1 Glycoside Type-II Antidiabetic Agents 21 2.4.2 Gliflozins 21 2.4.3 Gliflozins and Their Cardiovascular Benefits 23 References 24 Part II Polyphenols and Related Derivatives 27 3 Polyphenols and Related Derivatives 29 3.1 Introduction 29 3.1.1 Polyphenols 29 3.2 The Biosynthetic Shikimate Pathway 30 3.2.1 Aromatic Aminoacids 30 3.2.1.1 Phenyl Propanoids 30 3.2.1.2 Gallic Acid and Tannins 30 3.2.1.3 Galls 32 3.3 Phenylpropanes 33 3.3.1 Cinnamic Acid 33 3.3.2 Balsams 34 3.3.3 Cinnamon 36 3.3.4 Essential (Volatile) Oils 36 3.3.5 Vanilla 38 3.3.6 Vanillin 40 3.4 Podophyllotoxin 41 References 44 Further Reading 44 4 Benzopyrane-Based Structures 45 4.1 Coumarins, Furochromones 45 4.2 Coumarins 45 4.2.1 Anticoagulants from Sweet Clover 45 4.3 From Plant-Derived Coumarins to Modern Non Plant-Derived 47 4.3.1 Anticoagulant Therapeutic Agents 47 4.4 Furochromones 52 4.4.1 Khellin as a Source of Coronary Dilators: Calcium Channel Blockers and Other Related Derivatives 52 4.5 BIS-Chromones as Mast Cell Stabilizers 59 4.5.1 Disodium cromoglicate. Chromolyn sodium as bronchodilator 59 4.5.2 Benzofuran Antiarrythmia 60 References 61 5 Flavonoids 63 5.1 Flavones 63 5.2 Rutin (Rutoside) 68 5.3 Quercetin 70 5.4 Tea 71 5.5 Isoflavones 72 5.6 Flavone Alkaloids and Indol-based Natural Products as Cyclic-dependent Kinase Inhibitors (CDK-Inhibitors) 74 5.6.1 Flavone Alkaloid Rohituquine, Flavopiridol and Pyrimidine-related CDK Inhibitors 74 5.6.1.1 The Cell Division Cycle 74 5.6.2 Development of CDK Inhibitors 76 5.6.2.1 Non-Plant Derived CDK Inhibitors 78 5.7 Indole-based Natural Products as Cyclic Dependent Kinase Inhibitors 83 5.7.1 Indigo and Indirubine CDK Inhibitors 83 References 88 Part III Terpenes and Isoprenoids 91 6 Terpenes and Isoprenoids 93 6.1 Terpenes 93 6.1.1 Introduction 93 6.2 Monoterpenes 95 6.3 Cannabis and cannabinoids 95 6.3.1 Cannabis 95 6.3.1.1 The Long Journey of a Controversial and Paradigmatic Plant 95 6.3.2 Cultivation 97 6.3.3 Chemistry 98 6.3.4 Terpenes in Cannabis 100 6.3.5 Cannabis as a Crude Drug 101 6.3.6 Therapeutic Cannabinoids 102 6.3.7 Cannabidiol 103 6.3.8 Endocannabinoids 105 References 107 Further Reading 108 7 Sexquiterpenes (C15) and Diterpenes (C20) 109 7.1 Sexquiterpenes: Artemisia 109 7.1.1 Diterpenes: Ginkgo 109 7.2 Santonine 109 7.3 Artemisinin 110 7.3.1 From Ancient Recipes to Modern Drugs 112 7.3.1.1 Artemisinin Production 114 7.4 Diterpenes 117 7.4.1 Ginkgolides 117 References 122 8 Diterpenes II. Taxanes 125 8.1 Taxanes: Paclitaxel, Docetaxel, Cabazitaxel 125 8.1.1 Semi-Synthesis of Taxanes 128 8.1.2 Production 130 References 133 Further Reading 133 9 Triterpenes 135 9.1 Triterpenes (C30) 135 9.2 Glycoside Pentacyclic Triterpenoid Saponines 135 9.2.1 Triterpenoid Saponin Biosynthesis 137 9.2.2 Glycyrrhizin and Glycyrrhizic Acid 139 9.2.2.1 Liquorice Root 139 9.2.3 Quillaja Saponin 141 9.3 Ginseng and Ginsenosides 142 9.3.1 Ginsenoside Biosynthesis 144 9.4 Siberiang Ginseng (Eleutherococcus) 146 9.5 Triterpene Carboxylic Acids 146 9.5.1 Betulinic Acid 147 References 148 Further Reading 149 Part IV Steroids and Plant Natural products as raw materials for Steroid production. Cardioactive Glycosides 151 10 Early Steroid Chemistry. Introduction. Sexual Hormones I 153 10.1 Steroids 153 10.1.1 Introduction 153 10.1.1.1 A brief history 153 10.1.2 Five Centuries Later… 155 10.2 Nomenclature/Structural Determination/ Stereochemistry 161 10.3 Structural Determination 162 10.3.1 Primitive Methods 162 10.4 Estranes. Steroids in Which Ring a is Aromatic 164 10.4.1 Oestrogens. Oestrone. Estradiol 164 10.5 17α-Ethinyl Oestradiol 168 10.6 Early Pharmaceutical Production of Oestrogens 171 10.6.1 Progynon B Oleosum 172 10.7 Androstanes 173 10.7.1 Androgens. Androsterone. Testosterone 173 10.7.1.1 Androsterone 173 10.7.2 Testosterone 175 A Appendix to Chapter 10 179 A.1 Urinary Hormones in Medieval China 179 References 180 Further Reading 180 11 Early Steroid Chemistry. Sexual Hormones II, Progestagens. Pregnanes 181 11.1 Progesterone. The Hormone of Pregnancy, the Corpus Luteum Hormone 181 11.2 Progesterone as a Drug. Isolation of Progesterone 181 11.2.1 Progesterone: Isolation and Structural Determination 181 11.2.2 Approaches to the Synthesis of Progesterone in Germany Before WorldWar II 183 11.2.3 Progesterone as an Active Ingredient in Gestagen Formulations 185 11.2.4 Gestagens by the Oral Route: Ethistherone, the First Step 186 11.2.5 Progesterone as Prototype of Ovulation-Inhibiting Drugs: Synthetic Progesterone Analogues: Progestins 188 11.2.6 17α-hydroxyprogesterone 188 Further Reading 191 12 Steroid Chemistry III. Steroid Starting Materials 193 12.1 Phytochemicals as Raw Materials for the Semisynthesis of Steroidal Hormones 193 12.2 Mexican ‘Dioscoreas’, a Major Source of Steroids 194 12.2.1 From Saponin Diosgenin to Progesterone 194 12.2.1.1 Mexican Dioscoreas and Russell E. Marker 194 12.3 Rhizome of Mexican Dioscoreas as a Source of Steroids 198 12.4 Other Dioscoreas 201 12.5 Soya-bean Oil. A Major Source of Raw Materials for the Semisynthesis of Steroid Molecules 201 12.5.1 The Phytosterol Route: From Stigmasterol to Progesterone 201 12.5.2 Stigmasterol 202 12.5.3 Physostigmine, Stigmasterol and Percy Julian 202 12.6 Stigmasterol from Crude Soya Bean 203 12.7 Progesterone from Stigmasterol. Upjohn Process (1950s–1960s) 204 12.8 Soya-bean Seed 209 References 210 Further Reading 210 13 Steroid Chemistry IV. From Oestrone to 19-Nor Steroids 211 13.1 Contraceptive Agents 211 13.1.1 19-Nor Steroids 211 13.2 Norandrostane-based Steroids. Ethisterone 211 13.2.1 Industrial Production of Oestrone by Syntex. Production of Oestrone from Diosgenin 216 13.3 Androgenic-Anabolic Agents 219 13.3.1 Gonane-based Androgens 219 A Appendix to Chapter 13 221 A.1 19-Norsteroids 221 A.1.1 Total Synthesis 221 References 223 Further Reading 223 14 Steroid Chemistry V. Corticosteroids and Analogues. Adrenal Cortical Hormones 225 14.1 Cortisone, the Glucocorticoid Hormone. The Beginnings of the Cortisone Era 225 14.1.1 Cortisone from Bile Acids 227 14.2 Cortisone from Steroidal Sapogenins 229 14.2.1 Sarmentogenin 229 14.2.2 Hecogenin 230 14.2.3 Hecogenin from Sisal 230 14.3 Cortisone from Progesterone (1955). The Commercial Synthesis of Cortisone 232 14.3.1 17α-acetoxy Progesterone 237 14.3.2 Cortexolone Diacetate 238 14.4 Adrenal Cortical Hormones 239 14.4.1 Aldosterone, the Mineralocorticoid Hormone 239 14.5 Fluoro-Corticosteroids/Unsaturation Ring A 245 14.5.1 Fluorocorticoids: Fluodrocortisone 246 14.5.2 Methodology for Introducing Fluorine in 9α 247 14.6 Unsaturation Ring A. Prednisone, Prednisolone 248 14.7 6α-Methyl Corticosteroids 249 14.7.1 Introduction of 6α Methyl Group. 6α-Methylprednisolone 249 14.7.2 Triamcinolone 250 14.8 C-16 Methylcorticosteroids 252 14.8.1 Topical Corticosteroids 253 14.9 Corticosteroids. An Approach to an End… 256 14.10 Summary 257 References 260 Further Reading 260 15 Cardioactive Glycosides 261 15.1 Cardioactive Glycosides 261 15.1.1 Digitalis and Strophantus Glycosides 261 15.2 Introduction 261 15.2.1 Congestive Heart Failure (CHF) 264 15.3 Digitalis: Chemistry and Pharmacy 266 15.3.1 The Legal Reaction 268 15.3.2 Glycosides from Digitalis lanata 271 15.4 Glycosides from Digitalis Purpurea 271 15.5 Saponins on Digitalis Leaves 273 15.6 Strophantus 274 15.6.1 Convallaria 277 15.7 Squill (White Squill) 277 15.8 Toad Venom and Bufotoxin 279 Further Reading 280 Part V Alkaloids 281 16 Aminoalkaloids. Mescal. Ephedra 283 16.1 Drugs Affecting Adrenergic (Sympathetic) Neurotransmission 283 16.1.1 Ephedrine and Adrenergic Agents 283 16.2 Mescal. Mescaline 283 16.3 Ephedra. Drugs Affecting Adrenergic (Sympathetic) Neurotransmission. Adrenergic (Sympathomimetic) Agents 284 16.3.1 Ephedrine, Adrenaline (Epinephrine) and Related Drugs 284 16.4 ‘Ephedra’ Alkaloids and Ephedrine 286 16.4.1 Ephedra. A Brief History 288 16.5 Ephedrine versus Epinephrine (Adrenaline) 289 16.6 Adrenaline (Epinephrine) and Related Drugs. Adrenergic Agents 290 16.6.1 Adrenergic Receptors 292 16.7 Epinephrine (Adrenaline) and Ephedrine Analogues. Structure-activity Relationships 293 16.8 Short Acting β2 Adrenoreceptor Agonists (SABAs) 295 16.8.1 Selective β2 Adrenergic Agonists: Pure Bronchodilators 295 16.9 Long Acting Selective β2 Adrenoceptor Agonists (LABAs) 296 References 299 A Appendix to Chapter 16 299 A.1 Photos of Ephedra Bundles, Chart Ephedrine and Ephetonin from Merck KGaA (Darmstadt) Germany 299 17 Pyridine and Piperidine Alkaloids. Areca. Capsicum 303 17.1 Arecoline and Cholinergic Agents 303 17.2 Piperine 303 17.3 Capsaicin 305 17.4 Tropolone Alkaloids. Colchicumcapsaicin 306 17.5 Colchicine 307 References 309 A Appendix to Chapter 17 310 A.1 Acetylcholine and Cholinergic Receptors 310 18 Tropane Alkaloids I. Atropa belladonna and Datura stramonium 313 18.1 Tropane Alkaloids and Anticholinergic Drugs. Bronchodilators in Asthma and COPD 313 18.1.1 Reaction of Vitali-Morin 313 18.2 Atropine Atropine as Prototype of Anticholinergic Drugs 313 18.3 Scopolamine 319 18.3.1 Production of Alkaloids 320 18.4 Tropanol Esters. Atropine as a Prototype for the Development of Anticholinergic Drugs 322 18.4.1 Mydriatics Homatropine and Tropicamide 322 18.4.2 Antispasmodic Hioscine, Butyl Bromide 323 18.4.3 Short Acting Muscarinic Antagonists (SAMAs) 324 18.4.3.1 Synthetic Anticholinergics in Asthma and COPD 324 18.4.3.2 Long-Acting Muscarinic Antagonists (LAMAs) 325 18.5 Bronchodilators in the Treatment of Asthma and COPD (see also Chapter 16, Ephedra and Adrenergic Agents) 326 18.5.1 Dual Bronchodilator Therapy 327 18.6 Asthma/Allergic Disorders. COPD 328 References 328 19 Tropane Alkaloids II Coca Leaf (Cocae folium). Cocaine and Local Anaesthetics 331 19.1 Introduction. Historical Background 331 19.2 The Chemistry of Coca Leaves 335 19.2.1 Cocaine Hydrochloride. Cocaine an Ancient Anaesthetic 338 19.3 Synthetic Local Anaesthetics 338 19.3.1 Structural Variations on Cocaine. From Cocaine to Procaine. Amino-alcohol-type Local Anaesthetics 339 19.3.1.1 Eucaines, the First 339 19.3.2 Ortoforms, Stovaine, Benzocaine and Procaine 341 19.3.3 Anilide-type Local Anaesthetics. Lidocaine and Further Developments 342 19.3.3.1 Lidocaine 342 19.3.4 Mepivacaine, Bupivacaine, Ropivacaine 346 References 348 Further Reading 348 A Appendix to Chapter 19 348 A.1 Amide-Type Local Anaesthetics as Antiarryhtmic Drugs. Other Antiarrhythmic Drugs 348 20 Isoquinoline AlkaloidsIsoquinoline Alkaloids 351 20.1 Opium, Opium Alkaloids and Their Derivatives. Morphine. Structural Variations on Morphine 351 20.1.1 Introduction 351 20.1.2 Chemical Synthesis of Isoquinolines 351 20.1.2.1 Synthesis of Bischler-Napieralski 351 20.1.2.2 Synthesis of Pictet-Spengler 352 20.2 Opium, Opium Alkaloids and Their Derivatives 354 20.3 Opium 354 20.3.1 Divinum opus est sedare dolorem Hippocrates 354 20.3.2 Papaverine 357 20.3.3 Opium in the European Pharmacopoeia 359 20.3.4 Morphine 360 20.3.5 Codeine 361 20.3.6 Thebaine 361 20.4 Structural Variations on Morphine. Morphine Fragmentation 365 20.5 Structural Variations on Morphine I. Simple Modifications 365 20.5.1 Narcotic Antagonists 365 20.6 Structural Variations on Morphine II 367 20.6.1 Rigid Opioids: Morphinans and Benzomorphans 367 20.6.1.1 Morphinans 367 20.6.1.2 Benzomorphans 368 20.7 Structural Variations on Morphine III. Flexible Opioids 370 20.7.1 4-Phenyl Piperidines. Meperidine = Pethidine 370 20.7.2 Schaumann’s Postulate 371 20.8 Structural Variations on Morphine IV. 4-Phenyl Piperidines 372 20.8.1 From Meperidine to Butyrophenone Neuroleptics 372 20.8.1.1 Haloperidol 372 20.9 Structural Variations on Morphine V. 4-Phenyl Piperidines 374 20.9.1 Opioid-Based Antidiarrheals. Diphenoxilate. Loperamide 374 20.10 Structural Variations on Morphine VI. Flexible Opioids 376 20.10.1 4-Anilido-Piperidines 376 20.10.1.1 Fentanyls 376 20.11 Structural Variations on Morphine VII 378 20.11.1 Methadone 378 20.12 Structural Variations on Morphine VIII. Simplified Codeines. Flexible Opioids as Dual Acting Agents: Tramadol and Tapentadol 378 20.12.1 Tapentadol 380 References 382 Further Reading 382 21 Isoquinoline Alkaloids 383 21.1 Introduction and Historical Background 383 21.1.1 Natural Curares 385 21.1.1.1 Historical Background 385 21.1.2 Early Missionaries and Explorers 387 21.1.2.1 Father José Acosta S.J. 387 21.1.2.2 Father José Gumilla S.J. 387 21.1.3 Alexander von Humboldt and Aimé Bonpland 389 21.2 Eduard Friedrich Poeppig and Schomburgk brothers 390 21.2.1 Eduard Friedrich Poeppig 390 21.2.2 Schomburgk brothers, Robert and Moritz-Richard, German-born explorers and botanists 392 21.3 The First Experimental Studies 393 21.3.1 Early Classification of Curares 393 21.3.1.1 Claude Bernard 393 21.3.1.2 Rudolf Böhm 394 21.3.1.3 Tubocurare 394 21.3.1.4 Calabash Curare 394 21.4 Botanical Sources of Curares 396 21.5 Chemistry of Curares 396 21.5.1 Curare from Chondodendron. Intocostrin®, the First Pharmaceutical Formulation of a Curare Extract 396 21.5.2 Tubocurarine, the First Curare-Like Drug 398 21.5.3 Curares. Several Methods of Preparation 400 21.6 Tetrahydroisoquinoline-based Curare-like Agents. From Alkaloid Petaline to Synthetic Atracurium 403 21.7 Steroid-based Curare-like Agents. From Alkaloid Malouetine to Pancuronium and Other Curoniums 408 21.8 Reversal Agents of Neuromuscular Blockade: Cyclodextrins: Sugammadex Sodium 414 References 415 21 bis-Terpenoid Isoquinoline Alkaloids: Ipeca Alkaloids 417 21.1 Alkaloids from Ipeca 417 22 Amaryllidacea Alkaloids. Galantamine 419 22.1 Galantamine 419 22.2 Racemic Synthesis of Galantamine 423 22.2.1 Asymmetric Synthesis of (−) Galantamine 425 References 425 Further Reading 425 23 Indole Alkaloids. Introduction 427 23.1 Physostigmine 427 23.2 Alzheimer’s Disease 430 References 432 24 Terpene Indole Alkaloids. Introduction 433 24.1 Terpene Indole Alkaloids. Antitumour Vinca Alkaloids 433 24.1.1 Vinorelbine 433 24.2 Terpene Indole Alkaloids. Reserpine 434 24.2.1 Vinorelbine 438 24.3 Reserpine 439 24.4 Terpene-Indole Alkaloids. Ergot Alkaloids. Ergotamine. Ergobasine 440 24.4.1 Ergolines 444 References 445 Further Reading 445 A Appendix to Chapter 24 445 A.1 Triptans 445 25 Quinoline Alkaloids 447 25.1 Malaria. Cinchona Bark and Quinine 447 25.1.1 From Quinine to Synthetic Antimalarials 447 25.1.2 The Plasmodium Cycle 447 25.2 Cinchona Bark 449 25.2.1 Introduction and Historical Background 449 25.3 Scientific Expeditions to the NewWorld. The Spanish Enlightenment (Eighteenth Century) 451 25.4 Cinchona Bark Alkaloids. The Chemistry of Cinchona Alkaloids. An Approach 457 25.4.1 Isolation and Production of Quinine 457 25.4.2 The Quinine Structure 459 25.4.3 Synthesis deWooward-Doering 460 25.4.4 Quinine Sulphate, Today 463 25.4.5 Quinidine Sulphate 463 25.5 From Quinine to Synthetic Antimalarials 463 25.5.1 Amino-Acridines and Amino-Quinolines 463 25.5.2 Chloroquine, Antimalarial Discovered Twice 464 References and Notes 467 A Appendix to Chapter 25 468 A.1 Synthetic Antimalarials. Antifolates 468 A.1.1 Proguanil/Cycloguanil 468 A.1.2 Atovaquone 469 26 Quinoline Alkaloids 471 26.1 Camptotheca 471 26.1.1 Camptothecine and Derivatives as Anticancer Agents 471 References 477 Further Reading 478 27 Miscellaneous 479 27.1 Cephalotaxus Alkaloids: Homoharringtonine (Omacetaxine Mepesuccinate) 479 27.2 Purine Alkaloids: Xanthines 482 References 484 Index 485

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Enrique Ravina studied pharmacy at the University of Santiago de Compostela, Spain, where he obtained his PhD in 1969 and was appointed Professor of Organic Chemistry in 1975. Since 1981 he has been Professor of Medicinal and Pharmaceutical Chemistry at the same University. He is a member of the Spanish Royal Academy of Pharmacy, a founding member of the Spanish Society of Medicinal Chemistry and a member of the American Chemical Society.

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