Plant Secondary Metabolites : Physico-Chemical Properties and Therapeutic Applications

Plant secondary metabolites are plant-based natural products that display a variety of pharmacological effects. This book discusses the invaluable bioactivity and multifaceted potential of these compounds. The book describes the physico-chemical and biochemical aspects of the plant secondary metabolites along with the chemistry, therapeutics and future perspectives of these plant secondary metabolites. Moreover, the book also discusses about various sources of plant secondary metabolites, and the metabolite determination through various analytical techniques. It further describes the potential applications of plant secondary metabolites as anticancer and chemo preventive agents, their role as cosmetic ingredients and activity in skin cancer therapy. Further chapters emphasize upon the plethora of roles of plant secondary metabolites, including those as antivirals, anti-bacterial, anti-inflammatory drugs, cardioprotective agents etc. The book culminates with chapters on the impact of certain plant secondary metabolites in plant defence and human healthcare. This book is meant for researchers and students in the field of pharmacology and plant sciences. Moreover, this book is also useful for industry experts especially working in the field of herbal therapeutics. Preface Contents About the Editors 1: Plant Secondary Metabolites: An Introduction of Their Chemistry and Biological Significance with Physicochemical Aspect 1.1 Introduction 1.2 Phenolics and Polyphenolics 1.2.1 Flavonoids 1.2.2 Non-flavonoids 1.3 Nitrogen-Containing Compounds 1.3.1 Alkaloids 1.3.1.1 True Alkaloids 1.3.1.2 Protoalkaloids 1.3.1.3 Pseudoalkaoids 1.3.1.4 Polyamines Alkaloids 1.3.1.5 Peptide and Cyclopeptide Alkaloids 1.3.2 Cyanogenic Glycosides 1.3.3 Glucosinolates 1.3.4 Nonprotein Amino Acid 1.4 Terpenes/Terpenoids 1.4.1 Hemiterpenoids 1.4.2 Monoterpenoids 1.4.3 Sesquiterpenoids 1.4.4 Diterpenoids 1.4.5 Sesterterpenoids 1.4.6 Triterpenoids 1.4.7 Sesquarterpenoids 1.4.8 Tetraterpenoids 1.4.9 Polyterpenoids 1.4.10 Irregular Terpenoids 1.5 Sulfur-Containing Compounds 1.5.1 Phytochelatins 1.5.2 Glucosinolate 1.5.3 Phytoalexins 1.5.4 Defensins 1.5.5 Thionins 1.6 Physiochemical Aspect of Plant Secondary Metabolites (PSMs) 1.7 Biological Activities of Plant Secondary Metabolites (PSMs) 1.7.1 Antioxidant Effects 1.7.2 Antimicrobial Effects 1.7.3 Anticancer Effects 1.7.4 Antidiabetic Effects 1.7.5 Anti-inflammatory Effect 1.7.6 Antidepressant 1.8 Conclusion References Chapter 2: Natural Sources of Plant Secondary Metabolites and the Role of Plant Polyphenols in the Green Photosynthesis of Met... 2.1 Plant Secondary Metabolites: From Plants to Industrial Products 2.2 Plant Polyphenols 2.2.1 Flavonoids 2.2.2 Lignans 2.2.3 Stilbenes 2.2.4 Phenolic Acid 2.3 Phytosynthesis of Metallic Nanoparticles 2.4 Polyphenols in Nanoparticle Phytosynthesis 2.4.1 Nanoparticle Synthesis Methods 2.4.2 Characterization and Properties 2.4.3 Flavonoids in Nanoparticle Phytosynthesis 2.4.3.1 Platycladi cacumen Extract in Silver Nanoparticle Synthesis 2.4.3.2 Selaginella bryopteris (L.) Baker (1884) Extract in Silver Nanoparticle Synthesis 2.4.3.3 Salvia officinalis L. Extract in Silver Nanoparticle Synthesis 2.4.3.4 Chenopodium murale L. Leaf Extract in Silver Nanoparticle Synthesis 2.4.4 Phenolic Acids in Nanoparticle Phytosynthesis 2.4.4.1 Camellia sinensis (L.) Kuntze Extract in Silver Nanoparticle Synthesis 2.4.4.2 Parkia speciosa Hassk. Extract in Silver Nanoparticle Synthesis 2.4.5 Lignans in Nanoparticle Phytosynthesis 2.4.5.1 Forsythia suspensa (Thunberg) Vahl Fruit Extract in Silver Nanoparticle Synthesis 2.4.5.2 Sesamum indicum L. Extract in Silver Nanoparticle Synthesis 2.4.5.3 Streblus asper Lour. Extract in Silver Nanoparticle Synthesis 2.4.6 Stilbenes in Nanoparticle Phytosynthesis 2.5 Concluding Remarks and Perspectives References 3: Plant Secondary Metabolite Determination Through Analytical Chromatographic Techniques: Recent Trends and Advancement 3.1 Introduction 3.1.1 High-Pressure Thin-Layer Chromatography (HPTLC) 3.1.2 High-Pressure Liquid Chromatography 3.1.3 GC-MS 3.2 Conclusion References 4: Role of Plant Secondary Metabolites as Anticancer and Chemopreventive Agents 4.1 Introduction 4.2 Side Effects Associated with Cancer Treatment Regimes 4.3 Plant Secondary Metabolites as Anticancer Agents 4.3.1 Terpenoids or Terpenes 4.3.1.1 Monoterpenoids 4.3.1.2 Sesquiterpenoid 4.3.1.3 Diterpenoids 4.3.1.4 Triterpenoids 4.3.1.5 Tetraterpenoids 4.3.2 Polyphenols 4.3.2.1 Curcumin 4.3.2.2 Quercetin 4.3.2.3 Resveratrol 4.3.2.4 Flavonoids 4.3.3 Nitrogen-Containing Compounds 4.3.3.1 Alkaloids Indole Alkaloids Isoquinoline Alkaloids Phenanthroindolizidine Alkaloids Indoquinoline Alkaloids Benzophenanthridine Alkaloids 4.3.3.2 Glucosinolates 4.4 Conclusion References 5: Plant Secondary Metabolites: Natural Compounds as Cosmetic Ingredients and Their Potential Activity in Skin Cancer 5.1 Introduction 5.2 Skin Cancer Therapy 5.2.1 Basal Cell Carcinoma 5.2.2 Squamous Cell Carcinoma 5.2.3 Melanoma 5.3 Phytochemicals 5.3.1 Polyphenolic Compounds 5.3.1.1 Quercetin 5.3.1.2 Apigenin 5.3.1.3 Silymarin and Silybin 5.3.1.4 Diosmin 5.3.1.5 Fisetin 5.3.1.6 Luteolin 5.3.1.7 Catechins 5.3.1.8 Curcumin 5.3.1.9 Resveratrol 5.3.2 Polysaccharides 5.3.3 Volatile Oils 5.3.3.1 Terpin-4-Ol 5.3.3.2 Geraniol 5.3.3.3 α-Pinene 5.3.3.4 α-Santalol 5.3.3.5 Eugenol 5.3.3.6 Boswellic Acids 5.3.4 Alkaloids 5.3.4.1 Berberine 5.3.4.2 Paclitaxel 5.3.4.3 Glycoalkaloids Isolated from Solanaceae 5.3.5 Proanthocyanidins 5.3.6 Caffeic Acid Phenethyl Ester 5.3.7 Allyl Sulfides 5.3.8 Capsaicin 5.4 Conclusions References 6: Natural Remedies for a Healthy Heart: The Evidence-Based Beneficial Effects of Polyphenols 6.1 Background 6.2 Structure and Bioavailability of Vegetal Secondary Metabolites 6.2.1 Terpenes 6.2.2 Nitrogen and Sulfur-Containing Compounds 6.2.3 Phenolic Compounds 6.2.4 Polyphenols Bioavailability 6.3 The General Mechanism Responsible for the Beneficial Effects of Polyphenols in CVD 6.4 Beneficial Actions of Polyphenols Concerning Redox Homeostasis 6.4.1 Direct Antioxidant Action 6.4.2 Indirect Action Supporting Antioxidant Systems 6.4.3 Indirect Action Inhibiting Oxidative Stress-Enhancing Systems 6.4.4 Reports Regarding Antioxidant Effects in Human Studies 6.5 Protective Effects Involving Lipid Metabolism 6.5.1 Preclinical Reports 6.5.2 Clinical Evidence 6.6 Polyphenols and Platelet Function: Experimental and Preclinical Results 6.6.1 Antiplatelet Effects in Clinical Settings 6.7 Polyphenols and Inflammation 6.7.1 Experimental Studies Supporting the Effect of Polyphenols on Inflammatory Pathways 6.7.2 Anti-inflammatory Effects of Polyphenols in Preclinical and Clinical Settings 6.8 Conclusions References 7: Kauranes as Anti-inflammatory and Immunomodulatory Agents: An Overview of In Vitro and In Vivo Effects 7.1 Introduction 7.2 Chemistry of Kauranes 7.3 Anti-inflammatory Activity of Kauranes on Cells of the Immune System 7.3.1 Anti-inflammatory Effects on Neutrophils 7.3.2 Anti-inflammatory Effects on Monocytes and Macrophages 7.3.2.1 Effect of Kauranes on Monocytes and Peripheral Macrophages 7.3.2.2 Effects on Macrophages of the Central Nervous System (Microglia) 7.3.3 Anti-inflammatory Effects on Dendritic Cells 7.3.4 Anti-inflammatory Effects on CD4+ Helper T-Cell Activation and Differentiation 7.4 Other Anti-inflammatory Effects Associated with Kauranes 7.5 In Vivo Effects in Animal Models 7.5.1 Effects of Kauranes in Animal Models of Acute Inflammation 7.5.2 Effects of Kauranes in Animal Models of Rheumatoid Arthritis 7.5.3 Effects of Kauranes in Animal Models of SLE 7.5.4 Effects of Kauranes in Animal Models of IBD 7.5.5 Effects of Kauranes in Animal Models of Lung Conditions 7.5.6 Effects of Kauranes in Animal Models of Acute Liver Injury, Hepatotoxicity, and Liver Fibrosis 7.5.6.1 Acute Liver Injury 7.5.6.2 Hepatotoxicity 7.5.6.3 Liver Fibrosis 7.5.7 Effects of Kauranes in Animal Models of Neurological Diseases 7.5.7.1 Alzheimer ́s Disease 7.5.7.2 Parkinson ́s Disease 7.5.7.3 Multiple Sclerosis 7.5.7.4 Guillain-Barré Syndrome 7.5.8 Effects of Kauranes in Animal Models of Diabetes 7.5.9 Effects of Kauranes in Other Animal Models of Inflammation In Vivo 7.6 Future Perspectives 7.7 Conclusions References 8: Role of Plant Secondary Metabolites in Metabolic Disorders 8.1 Introduction 8.1.1 Physiology of Metabolism 8.1.2 Cell: The Metabolic Processing Center 8.2 Introduction to Metabolic Disorders 8.3 Association of Significant Dietary Habits with Metabolic Syndrome 8.4 Causes of Metabolic Disorders 8.5 Role of Polyphenols in Health 8.6 Polyphenols and Their Role in the Human Body 8.7 Metabolic Syndrome and Oxidative Stress 8.8 Phytotherapeutic and Metabolic Disorders 8.9 Role of Secondary Metabolites in Type 1 and Type 2 Diabetes Mellitus 8.10 Plant Metabolism and Secondary Metabolites 8.11 Importance and Main Role of Secondary Metabolites 8.12 Antioxidant Potential of Plant Phenols 8.13 Classification of Secondary Metabolites 8.14 Role of Secondary Metabolites in Thyroid Disease 8.15 Plant Polyphenols and Hepatitis 8.16 Secondary Metabolites in the Prevention of Hepatorenal Toxicity 8.17 Secondary Metabolites in Tuberculosis and Their Potency Against Tuberculosis 8.17.1 First Line Drugs 8.17.1.1 Isoniazid 8.17.1.2 Rifampicin 8.17.1.3 Ethambutol 8.17.1.4 Pyrazinamide 8.17.1.5 Streptomycin 8.17.2 Second-Line Medications 8.17.2.1 Fluoroquinolone 8.17.2.2 Aminoglycosides (Kanamycin, Amikacin, and Capreomycin) 8.17.2.3 Ethionamide and Prothionamide Ethionamide 8.17.2.4 P-Aminosalicylic Acid 8.17.2.5 Cycloserine 8.18 Therapeutic Use of Phytopolyphenols References 9: Metal Complexes of Plant Secondary Metabolites with Therapeutic Potential 9.1 Introduction 9.2 Classification 9.2.1 Terpenes 9.2.2 Nitrogen-Containing Compounds 9.2.3 Phenolics 9.2.4 Sulfur-Containing Compounds 9.3 Antioxidant Activity 9.4 Cytotoxic Activity for Cancer Therapy 9.5 Antimicrobial Activity 9.5.1 Antibacterial and Antifungal Activity 9.6 Antidiabetic Activity 9.7 Anti-inflammatory Activity 9.8 Anti-Alzheimer Activity 9.9 Other Activities 9.10 Conclusions References 10: Phytoalexins: Implications in Plant Defense and Human Health 10.1 Introduction 10.2 Chemically Diverse Nature of Phytoalexins 10.3 Biosynthesis of Phytoalexins 10.4 Distribution in Plant Families 10.5 Differential Mechanisms of Action in Phytopathogens with Different Lifestyles 10.6 De Novo Biosynthesis/Accumulation of Phytoalexins and Its Regulation 10.7 Phytoalexins from Two Model Plants 10.7.1 Arabidopsis 10.7.2 Rice 10.8 Role in Promoting Human Health 10.9 Phytoalexins as Food Preservatives 10.10 Transgenic Expression of Phytoalexins in Plants 10.11 Degradation/Detoxification of Phytoalexins 10.12 Conclusion and Future Prospects References 11: Secondary Metabolites from Plants: Role in Plant Diseases and Health Care 11.1 Introduction 11.2 Plant Disease and Resistance 11.3 Role of Phenolics in Plant Disease Resistance 11.4 Role of Terpenes in Plant Disease Resistance 11.5 Role of Alkaloids in Plant Disease Resistance 11.6 Role in Health Care 11.7 Antimicrobial Effect 11.7.1 Anticancer 11.7.2 Antioxidant Activity References 12: Plant Secondary Metabolites: Their Food and Therapeutic Importance 12.1 Introduction 12.2 Phenolics 12.3 Flavonoids 12.4 Flavonols 12.5 Flavan-3-ols 12.6 Anthocyanidins 12.7 Flavanones 12.8 Isoflavones 12.9 Simple Phenolics 12.10 Tannins 12.11 Coumarins 12.12 Flavonoids 12.13 Xanthones and Chromones 12.14 Stilbenes 12.15 Alkaloids 12.15.1 Nicotine 12.15.2 Caffeine 12.15.3 Vinblastine 12.16 Lipids 12.17 Lipid-Based Secondary Metabolites 12.17.1 Polyacetylenes 12.17.2 Phytosterols 12.17.3 Carbohydrates 12.17.3.1 Glycosides 12.17.3.2 Terpenoids 12.17.3.3 Saponins 12.18 Extraction of Plant Secondary Metabolites from Plants 12.19 Food Processing and Bioavailability of Plant Secondary Metabolites 12.20 Improvement in Delivery of Bioactive Compounds 12.21 Therapeutic Role of PSMs in Management of Chronic Health Diseases 12.21.1 Cardiovascular Disease 12.21.2 Cancer 12.21.3 Hyperlipidemia 12.21.4 Obesity 12.21.5 Diabetes 12.22 Renal Disorder 12.23 Alzheimer ́s Disease 12.24 Diarrhea 12.25 Conclusion and Future Thrust Area References 13: Role of Plant Secondary Metabolites as Modulators of Multidrug Resistance in Cancer Therapy 13.1 Introduction 13.2 Plant Secondary Metabolites (PSMs) 13.3 Multidrug Resistance (MDR) 13.4 ABC Transporters 13.5 Terpenoids 13.5.1 Monoterpenes 13.5.1.1 Citronellal and Citronellol 13.5.2 Diterpenes 13.5.2.1 Andrographolide 13.5.2.2 Jatrophane Diterpene Polyesters 13.5.2.3 Lathyrane Diterpenes 13.5.3 Triterpenes 13.5.3.1 Betulinic Acid, Pomolic Acid and Oleanolic Acid 13.5.3.2 Limonoids 13.5.3.3 Cumingianol A-F 13.5.3.4 Tormentic Acid 13.5.3.5 Glycyrrhizin 13.5.3.6 Uvaol 13.5.4 Steroids 13.5.4.1 Cardenolides 13.5.4.2 Cycloartanes 13.5.4.3 Methylprototribestin 13.5.4.4 Protopanaxatriol (Ginsenoside) 13.5.4.5 Stigmasterol and β-Sitosterol-O-Glucoside (Sterols) 13.5.4.6 Withaferin A 13.5.5 Tetraterpenes 13.5.5.1 Carotenoids 13.6 Phenolics 13.6.1 Phenylpropanoids 13.6.1.1 Chlorogenic Acid 13.6.1.2 Curcumin 13.6.2 Flavonoids and Related Polyphenols 13.6.2.1 Chrysin, Amorphigenin and Epigallocatechin 13.6.2.2 Genistein and Derivatives 13.6.2.3 Hesperidin and Neohesperidin 13.6.2.4 Mangiferin and Norathyriol 13.6.2.5 Tricin 13.6.3 Quinones, Anthraquinones and Naphthoquinones 13.6.3.1 Emodin, Aloe Emodin and Rhein 13.6.4 Lignans 13.6.4.1 Syringaresinol 13.6.5 Coumarins and Furanocoumarins 13.6.5.1 Bergamottin 13.7 Alkaloids 13.7.1 Acridone Alkaloids 13.7.1.1 Arboririne, Evoxanthine, Isogravacridone Chloride, Rutacridone and Others 13.7.2 Indole Alkaloids 13.7.2.1 Reserpine, Catharanthine, Vindoline and Others 13.7.3 Bisbenzylisoquinoline Alkaloids 13.7.3.1 Tetrandrine and Fangchinoline 13.8 Conclusion References 14: Plant Secondary Metabolites: Functions in Plants and Pharmacological Importance 14.1 Why Plants Produce Secondary Metabolites? 14.2 Selection of Plant Source and Isolation of Secondary Metabolites 14.3 Secondary Metabolites and Their Functions 14.4 General Mode of Action of SMs 14.5 Classification, Structure, and Distinctive Role of Secondary Metabolites 14.6 Pathway of Synthesis of Secondary Metabolites 14.7 Medicinal Applications of Some Important Secondary Metabolites 14.8 Conclusion References 15: Plant Secondary Metabolites in Antiviral Applications 15.1 Introduction 15.2 Alkaloids 15.2.1 Berberine 15.2.2 Hirsutine 15.2.3 Thalimonine 15.3 Phenolics 15.3.1 Flavonoids 15.3.1.1 Flavonoids as Antiviral Agents 15.3.1.2 Flavonols 15.3.1.3 Flavone 15.3.1.4 Isoflavone 15.3.1.5 Flavan 15.3.2 Coumarins 15.3.3 Tannins 15.3.4 Stilbenoids 15.4 Terpenes and Terpenoids 15.5 Carotenoids 15.6 Conclusion and Future Perspectives References