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.

Medicinal Chemistry of Plant-Derived Natural Products includes essential information covering practically all medicinal agents from plant origins studied in both chemical and pharmacological aspects. The book incorporates a wealth of primary information and references, including seminal publications and contemporary reviews.

Among others, it includes some biosynthetic pathways, selected synthesis and /or semi-synthesis as well as pharmacological colour schemes where these drugs interact in order to cause their response(s). Chapters incorporate an historical background focusing the plant-drug prototype and its further evolution.

Ideal for students, graduates, Professors preparing their lectures and researchers in academia and industry, Medicinal Chemistry of Plant-Derived Natural Products offers invaluable insights into the journey of transforming plants into pharmaceuticals.

The book represents a complementary contribution to the author's previous volume The Evolution of Drug Discovery: From Traditional Medicine to Modern Drugs (Wiley-VCH, 2011), and deals with plant-derived drug prototypes, semisynthetic to drugs inspired by the original, natural prototype, as well as raw plant substances as starting materials for drug synthesis. Together these books represent an agile approach to medicinal and pharmaceutical chemistry organized on the basis of the origin of current drugs.

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
1.2 Carbohydrates as Antidiabetic Agents 6

2 Natural Products Related to Carbohydrates 15
2.1 Glycosides 15
2.2 Anthraquinone Glycoside as Laxatives 16
2.3 Phenol Glycosides 19
2.4 Novel Strategy in the Treatment of Type-2 Diabetes 21

Part II Polyphenols and Related Derivatives 27

3 Polyphenols and Related Derivatives 29
3.1 Introduction 29
3.2 The Biosynthetic Shikimate Pathway 30
3.3 Phenylpropanes 33
3.4 Podophyllotoxin 41

4 Benzopyrane-Based Structures 45

4.1 Coumarins, Furochromones 45
4.2 Coumarins 45
4.3 From Plant-Derived Coumarins to Modern Non Plant-Derived 47
4.4 Furochromones 52
4.5 BIS-Chromones as Mast Cell Stabilizers 59

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
5.7 Indole-based Natural Products as Cyclic Dependent Kinase Inhibitors 83

Part III Terpenes and Isoprenoids 91

6 Terpenes and Isoprenoids 93
6.1 Terpenes 93
6.2 Monoterpenes 95
6.3 Cannabis and cannabinoids 95

7 Sexquiterpenes (C15) and Diterpenes (C20) 109
7.1 Sexquiterpenes: Artemisia 109
7.2 Santonine 109
7.3 Artemisinin 110
7.4 Diterpenes 117

8 Diterpenes II. Taxanes 125
8.1 Taxanes: Paclitaxel, Docetaxel, Cabazitaxel 125

9 Triterpenes 135
9.1 Triterpenes (C30) 135
9.2 Glycoside Pentacyclic Triterpenoid Saponines 135
9.3 Ginseng and Ginsenosides 142
9.4 Siberiang Ginseng (Eleutherococcus) 146
9.5 Triterpene Carboxylic Acids 146

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
10.2 Nomenclature/Structural Determination/ Stereochemistry 161
10.3 Structural Determination 162
10.4 Estranes. Steroids in Which Ring a is Aromatic 164
10.5 17 -Ethinyl Oestradiol 168
10.6 Early Pharmaceutical Production of Oestrogens 171
10.7 Androstanes 173

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

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
12.3 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
12.6 Stigmasterol from Crude Soya Bean 203
12.7 Progesterone from Stigmasterol. Upjohn Process (1950s-1960s) 204
12.8 Soya-bean Seed 209

13 Steroid Chemistry IV. From Oestrone to 19-Nor Steroids 211
13.1 Contraceptive Agents 211
13.2 Norandrostane-based Steroids. Ethisterone 211
13.3 Androgenic-Anabolic Agents 219

14 Steroid Chemistry V. Corticosteroids and Analogues. Adrenal Cortical Hormones 225
14.1 Cortisone, the Glucocorticoid Hormone. The Beginnings of the Cortisone Era 225
14.2 Cortisone from Steroidal Sapogenins