Discovery and Development of Antidiabetic Agents from Natural Products: Natural Product Drug Discovery

333 Pages·2017·12.064 MB·English

by  Goutam Brahmachari

Discovery and Development of
Antidiabetic Agents From Natural
Products
Natural Product Drug Discovery

Discovery and
Development of
Antidiabetic Agents
From Natural Products
Natural Product Drug Discovery
Goutam Brahmachari
Department of Chemistry
Visva-Bharati (a Central University)
Santiniketan, West Bengal, India

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ISBN: 978-0-12-809450-1
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Publisher: John Fedor
Acquisition Editor: Anneka Hess
Editorial Project Manager: Anneka Hess
Production Project Manager: Paul Prasad Chandramohan
Designer: Maria Inês Cruz
Typeset by TNQ Books and Journals
Dedicated To
Natural Product Chemists of the Past, Present, and Future

Contents
List of Contributors xiii
Editor Biography xv
Foreword xvii
Preface xix
1. Andrographolide: A Molecule of Antidiabetic Promise
C. Brahmachari
1. Introduction
2. The Molecule
3. Extraction, Purification, and Characterization Data of
Andrographolide 2
3.1 Extraction and Purification of Andrographolide From
Andrographis paniculata Nees 2
3.2 Physical and Spectral Data of Andrographolide 2
4. Total Synthesis of Andrographolide 3
5. Antidiabetic Potential of Natural Andrographolide and Its
Semisynthetic Derivatives 9
5.1 Antidiabetic Studies With Natural Andrographolide and
Deoxyandrographol ide 9
5.2 Antidiabetic Studies With Semisynthetic Derivatives of
Andrographolide 11
6. Studies on Pharmacokinetics and Metabolism 16
7. Safety Aspects of Andrographolide 20
8. Concluding Remarks 22
List of Abbreviations 22
Acknowledgments 23
References 23
2. Computer-Aided Discovery of Glycogen Phosphorylase
Inhibitors Exploiting Natural Products
Joseph M. Hayes
1. Introduction 29
2. Computer-Aided Drug Design Methods 31
vii
viii Contents
3. Applications of Computation to Glycogen Phosphorylase
Inhibitor Design 35
3.1 Introduction 35
3.2 Catalytic Site 35
3.3 Allosteric Site 42
3.4 New Allosteric Site 46
3.5 Inhibitor Site 49
4. Concluding Remarks 51
List of Abbreviations 53
Acknowledgments 53
References 53
3. Identification and Extraction of Antidiabetic
Antioxidants From Natural Sources
K. Rashid and P.C. Sil
1. Introduction 63
2. Curcumin: Extraction, Identification, and Antidiabetic-
Antioxidant Potential 64
2.1 Extraction and Estimation of Curcumin 66
2.2 Curcumin as an Antioxidant 69
2.3 Curcumin as an Antidiabetic Agent 70
2.4 Curcumin as an Antiinflammatory Agent 72
2.5 Mechanism of Curcumin-lnduced Protective Action in
Diabetes 73
2.6 Clinical Impact of Curcumin on Human 79
2.7 Bioavailability of Curcumin 80
2.8 Toxicity of Curcumin 80
3. Mangiferin: Extraction, Identification, and Antidiabetic-
Antioxidant Potential 80
3.1 Extraction and Identification of Mangiferin 82
3.2 Mangiferin as an Antioxidant 84
3.3 Mangiferin as an Antidiabetic Agent 86
3.4 Utilization of Mangiferin and Its Derivatives in Diabetes 86
3.5 Mechanism of Mangiferin-lnduced Protective Action in
Diabetes 87
3.6 Clinical Impact and Practical Use of Mangiferin 90
3.7 Bioavailability of Mangiferin 90
3.8 Toxicity of Mangiferin 90
4. Arjunolic Acid: Extraction, Identification, and Antidiabetic-
Antioxidant Potential 91
4.1 Extraction and Identification of Arjunolic Acid 92
4.2 Arjunolic Acid as an Antioxidant 92
4.3 Arjunolic Acid as an Antidiabetic Agent 93
5. Concluding Remarks 95
Abbreviations 97
References 98
Contents ix
4. Glucose Transporter 4 Translocation Activators
From Nature
K. Dev, E. Ramakrishna and R. Maurya
1. Introduction 113
2. Plant Formulations With Glucose Transporter 4
Translocation Activity 114
3. Naturally Occurring Compounds With GLUT4
Translocation Activity 116
3.1 Alkaloid and Amino Acid 116
3.2 Fatty Acids 11 7
3.3 Flavonoids 117
3.4 lsoflavonoids and Chalcones 120
3.5 Coumarins 121
3.6 Anthraquinones 122
3.7 Quinones and Naphthoquinones 123
3.8 Biphenyls and Lignans 124
3.9 Steroids 124
3.10 Terpenes 125
3.11 Phenols and Polyphenol 127
3.12 lridoids 131
3.13 Polysaccharides 132
3.14 Saponins 133
3.15 Tannins 133
3.16 Sulfonated Sugars 134
3.17 Miscellaneous 135
4. Natural Product Derivatives as GLUT4 Translocation
Activators 135
4.1 Chemical Modification of Lupeol 136
4.2 Chemical Modification of 4-Hydroxyisoleucine 137
4.3 Chemical Modification of Kojic Acid 137
5. Concluding Remarks 138
List of Abbreviations 139
Acknowledgments 140
References 140
5. Carbohydrate-Based Antidiabetic Agents From Nature
S. Mishra, A.S. Singh, N. Mishra, H. Pandey and V.K. Tiwari
1. Introduction 147
2. Diabetes: Definition and Classification 149
3. Importance of Carbohydrate in Antidiabetic Drug
Development 150
4. Glycosidase Inhibitors as Antidiabetic Agents 153
4.1 Novel Carbohydrate-Based a-Glucosidase Inhibitors With
Antidiabetic Activity 154