Kishan Gopal Ramawat Jean-Michel Merillon Editors

Natural

Products

Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes

Volume 1

With 1569 Figures and 307 Tables

^ Springer Reference

Contents

Volume 1 Part I

Alkaloids: General Biology and Biotechnology

1 Microbial Production of Plant Benzylisoquinoline Alkaloids ... Eitaro Matsumura, Motoki Matsuda, Fumihiko Sato, and Hiromichi Minami 2

1 3

Alkaloids of Marine Macroalgae Kasim Cemal Güven, Burak Coban, Ekrem Sezik, Hiiseyin Erdugan, and Ferda Kaleagasioglu

25

3 Neurotoxic Alkaloids from Cyanobacteria Ralf Kellmann, Olivier Ploux, and Brett A. Neilan

39

4 Bioproduction of Terpenoid Indole Alkaloids from Catharanthus roseus Cell Cultures Lorena Almagro, Mariana Sottomayor, and Maria Angeles Pedreno 5 Bioactive Alkaloids from South American Psychotria and Related Rubiaceae Helio Nitta Matsuura, Diogo Denardi Porto, and Arthur Germano Fett-Neto

85

119

6 Ecological Role of Alkaloids Shaily Goyal

149

7 Plant In Vitro Systems as Sources of Tropane Alkaloids Vasil Georgiev, Andrey Marchev, Strahil Berkov, and Atanas Pavlov

173

8 Biotechnology and Genetic Engineering for Alkaloid Production Smita Srivastava and Ashok Kumar Srivastava 9

Marine Pyrroloitninoquinone Alkaloids, Makaluvamines and Discorhabdins, and Marine Pyrrole-Imidazole Alkaloids Hiromichi Fujioka and Yasuyuki Kita

213

251

>v

Contents

X 10 Internet Natural Product Trade, Business, and Risk of Damaged and/or Contaminated Products Maria Laura Colombo, Maria Teresa Pinorini, and Ario Conti Part II

Alkaloids: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution

285

301

11 Alkaloids Derived from Lysine: Piperidine Alkaloids Eva Szoke, Eva Lemberkovics, and Läszlo Kursinszki

303

12

343

Alkaloids Derived from Ornithine: Tropane Alkaloids Stefan Philipov and Tsvetelina Doncheva

13 Alkaloids Derived From Ornithine: Pyrrolizidine Alkaloids .... Helmut Wiedenfeld 14

15

16

359

Alkaloids Derived from Lysine: Quinolizidine (a Focus on Lupin Alkaloids) Giovanna Boschin and Donatella Resta

381

Alkaloids Derived from Tyrosine: Modified Benzyltetrahydroisoquinoline Alkaloids Feroz Khan, Tabish Qidwai, Rakesh K. Shukla, and Vikrant Gupta

405

Alkaloids Derived from Tyrosine: Penethylisoquinoline (Autumnaline, Colchicine) Pijush Paul, Mihir Halder, and Sumita Jha

461

17 Amaryllidaceae Alkaloids Zhong Jin and Xiao-Hua Xu

479

18 Bioactive Alkaloids from Fungi: Psilocybin Zafar Alam Mahmood

523

19

20

Alkaloids Derived from Tryptophan: Harmine and Related Alkaloids T. D. Nikam, K. M. Nitnaware, and M. L. Ahire Alkaloids Derived from Tryptophan: Terpenoid Indole Alkaloids Shilpa Ramani, Nandadevi Patil, Suhas Nimbalkar, and Chelliah Jayabaskaran

21 Chemistry and Biology of Cinchona Alkaloids Karol Michal Kacprzak 22 Chemistry and Biology of Camptothecin and its Derivatives

553

575

605

643

Contents

xi

23 Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids Peter Mai and Shu-Ming Li 24

25

26

Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline Maria Fätima das Grabas Fernandes da Silva, Joäo Batista Fernandes, Moacir Rossi Forim, Paulo Cezar Vieira, and Israel Civico Gil de Sä

683

715

Alkaloids Derived from Histidine: Imidazole (Pilocarpine, Pilosine) Ana Paula Santos and Paulo Roberto H. Moreno

861

Alkaloids Derived by Amination Reaction: Acetate-Derived (Coniine) Rumen Binev

883

27 Ephedra Alkaloids-Alkaloids Derived by Amination Reaction: Phenylalanine Derived Ali Parsaeimehr and Elmira Sargsyan 28 Terpenoid Alkaloids Derived by Amination Reaction Krishna Prasad Devkota and Norbert Sewald

909 923

29 Purine Alkaloids, Cytokinins, and Purine-Like Neurotoxin Alkaloids Hiroshi Ashihara, Takao Yokota, and Alan Crozier

953

30

977

Aziridine Alkaloids: Origin, Chemistry and Activity Valery M. Dembitsky, Alexander O. Terent'ev, and Dmitri O. Levitsky

Volume 2 Part III

Alkaloids: Methods of Analysis

31 Methods of Analysis: Tropane Alkaloids from Plant Origin Philippe Christen, Stefan Bieri, and Strahil Berkov

1007 1009

32 Methods for Analysis of Pyrrolizidine Alkaloids Colin Crews

1049

33 Methods of Analysis of Opium Alkaloids Carmen Cruces-Blanco. Diego Airado-Rodrfeuez. and

1069

xiv

Contents

59 Flavones and Flavonols: Phytochemistry and Biochemistry Qiang Zhang, Xinhuai Zhao, and Hongbin Qiu 60 Isoflavonoids Varsha Sharma and Kishan G. Ramawat 61 Minor Flavonoids (Chalcones, Flavanones, Dihydrochalcones, and Aurones) Masayuki Ninomiya and Mamoru Koketsu

1821 1849

1867

62 Stiibenoids Tao Shen, Chun-Feng Xie, Xiao-Ning Wang, and Hong-Xiang Lou

1901

63 Phenolic Acids Marta Goleniowski, Mercedes Bonfill, Rosa Cusido, and Javier Palazon

1951

64

1975

Hydrolyzable Tannins: Gallotannins and Ellagitannins Michael Jourdes, Laurent Pouysegu, Denis Deffieux, Pierre-Louis Teissedre, and Stephane Quideau

Part Vil

Phenolics: Methods of Analysis

2011

65 Preparative Extraction and Separation of Phenolic Compounds Winny Routray and Valerie Orsat

2013

66

Mass Spectrometric Detection of Phenolic Acids Santi M. Mandal and Dipjyoti Chakraborty

2047

67

Analytical Methods of Phenolic Compounds Ioana Ignat, Irina Volf, and Valentin I. Popa

2061

68

Phenolic Compounds in Catharanthus roseus David M. Pereira, Patricia Valentäo, Mariana Sottomayor, Federico Ferreres, and Paula B. Andrade

2093

69

Flavonoids by HPLC S. W. Annie Bligh, Olumuyiwa Ogegbo, and Zheng-Tao Wang

2107

70

Polyphenol Purification by Solid Support-Free Liquid-Liquid Chromatography (CCC, CPC) Jane Hubert, Karen Ple, Mahmoud Hamzaoui, and Jean-Hugues Renault

Part VIII

Phenolics: Biological Activity and Bioavailability

71 Cellular, Molecular, and Biological Perspective of Polyphenols in Chemoprevention and Therapeutic Adjunct in Cancer Sanieev Baneriee and Paulrai Raiamani

2145

2173 2175

xv

Contents 72 Tannins and Anthocyanins of Wine: Phytochemistry and Organoleptic Properties Pierre-Louis Teissedre and Michael Jourdes 73 Grapevine Stilbenoids: Bioavailability and Neuroprotection Pierre Waffo-Teguo, Stephanie Krisa, Alison D. Pawlus, Tristan Richard, Jean-Pierre Monti, and Jean-Michel Merillon 74

Proanthocyanidins of Cocoa: Bioavailability and Biological Activities Manuel Rusconi, Maria Teresa Pinorini, and Ario Conti

2255

2275

2311

75

Polyphenols and Beer Quality Sonia Collin, Vesna Jerkovic, M. Bröhan, and D. Callemien

2333

76

Wine Polyphenols and Vascular Protective Effects Cyril Auger and Valerie B. Schini-Kerth

2361

77 Isoflavonoids and Phytoestrogenic Activity Catherine Bennetau-Pelissero 78 Phenolics in Human Nutrition: Importance of the Intestinal Microbiome for Isoflavone and Lignan Bioavailability Thomas Clavel and Job O. Mapesa 79 Bioavailability of Anthocyanins Ana Faria, Iva Fernandes, Nuno Mateus, and Concei§äo Calhau

2381

2433 2465

Volume 4 Part IX

Phenolics: Nutraceuticals and Functional Foods

80 Prospects of Functional Foods/Nutraceuticals and Markets Josep Valls, Nacho Pasamontes, Albert Pantaleon, Susana Vinaixa, Montse Vaque, Arantza Soler, Silvia Millän, and Xavier Gomez

2489 2491

81 Food Sources of Phenolics Compounds Wende Li and Trust Beta

2527

82

2559

Nutraceuticals and Antioxidants in Prevention of Diseases Neelam Jain and Kishan G. Ramawat

83 Functional Grapes Maria Isabel Fernändez-Marin, Raul F. Guerrero, Belen Puertas,

2581

xii

Contents

34

Analysis of Catharanthus Alkaloids Qinhua Chen and Zilin Chen

1121

35 Methods for Analysis of Ergot Alkaloids Colin Crews

1133

36

1153

Analysis of Alkaloids by Capillary Electrophoresis Roberto Gotti

Part IV 37

Alkaloids: Pharmacology

Pharmacology of Macroalgae Alkaloids Ferda Kaleagasioglu, Kasim Cemal Güven, Ekrem Sezik, Hüseyin Erdugan, and Burak Coban

1201 1203

38 Pharmacological Effects of Ephedrine Renata Pereira Limberger, Ana Laura Bemvenuti Jacques, Gabriela Cristina Schmitt, and Marcelo Dutra Arbo

1217

39

1239

Lycopodium Alkaloids: Pharmacology Elfn Soffia Olafsdottir, Elsa S. Halldorsdottir, N. M. Pich, and S. Omarsdottir

40 Scope of Alkaloids in Antileishmanial Drug Discovery and Development Bhuwan B. Mishra, Navneet Kishore, Rakesh K. Singh, and Vinod Kumar Tiwari 41 Pharmacological/Biological Effects of Berberine Eva M. Galvez, M. Perez, P. Domingo, D. Nunez, V. L. Cebolla, M. Matt, and J. Pardo 42

Alkaloids and Drug Discovery for Neurodegenerative Diseases Melanie-Jayne R. Howes

1263

1301

1331

43 Opioids and Pain Treatment Daniel Krashin, Andrea Trescot, and Natalia Murinova

1367

44

1383

Pyrrolizidine Alkaloid-Induced Toxicity to the Liver Manuela G. Neuman

45 Biological Activities of Pepper Alkaloids Krishnapura Srinivasan

1397

46

Antiangiogenic Alkaloids from Plants Flavia Cristine Mascia Lopes, Luis Octävio Regasini, Manuel Nuno de Magalhäes Pinheiro Algada, and Raquel Soares

1439

47

Prevention of Brain Disorders by Nicotine Karim Alkadhi, Samina Salim, and Karem Aizoubi

1469

xlii

Contents 48 Aconitum Alkaloids and Biological Activities Ainura Chodoeva, Jean-Jacques Bosc, and Jacques Robert 49

Alkaloids and Inhibitory Effects Against Enzymes Linked to Neurodegenerative Diseases (Physostigmine, Galanthamine, Huperzine, etc.) Ilkay Erdogan Orhan and F. Sezer Senol

Part V 50

Phenolics: General Biology and Biotechnology

Phenolic Compounds: Introduction Vincenzo Lattanzio

51 Metabolie Engineering for Functional Foods: Tomato Fruits and Stilbenes Giovanna Giovinazzo, Ilaria Ingrosso, Marco Taurino, and Angelo Santino

1503

1525

1541 1543

1581

52 Cocoa Cultivation, Directed Breeding and Polyphenolics Reinhard Lieberei, Daniel Kadow, and David Seigier

1599

53 Genetics of Flavonoids Ramesh Prasad Pandey and Jae Kyung Sohng

1617

54 Isoflavonoid Production by Genetically Engineered Microorganisms Brady F. Cress, Robert J. Linhardt, and Mattheos A. G. Koffas 55 Bioproduction of fra/is-Resveratrol from Grapevine Cell Cultures Lorena Almagro, Sarai Belchi-Navarro, Ana Belen Sabater-Jara, Juan Carlos Vera-Urbina, Susana Selles-Marchart, Roque Bru, and Maria Angeles Pedreno 56

Functional Foods: Genetics, Metabolome, and Engineering Phytonutrient Levels Tahira Fatima, Avtar K. Handa, and Autar K. Mattoo

1647

1683

1715

Volume 3 Part VI

Phenolics: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution

1751

57 Flavanols: Catechins and Proanthocyanidins Joana Oliveira, Nuno Mateus, and Victor de Freitas

1753

58 Anthocyanins Sonia de Pascual-Teresa, Maria Teresa Sanchez-Ballesta, and Cristina Garcia-Viguera

1803

xvi 84

Contents Potential Neuroprotective Actions of Dietary Flavonoids David Vauzour, Marcus Rattray, Robert J. Williams, and Jeremy P. E. Spencer

85 Improvement of Nutraceutical Value of Food by Plant Symbionts Manuela Giovannetti, Luciano Avio, and Cristiana Sbrana

Part X

Terpenes: General Biology and Biotechnology

2617

2641

2663

86 Terpenes: Chemistry, Biological Role, and Therapeutic Applications Priyanka P. Brahmkshatriya and Pathik S. Brahmkshatriya

2665

87

Biosynthesis of Terpenoids Nelson L. Brock and Jeroen S. Dickschat

2693

88

Biotransformation of Terpenoids and Steroids Wang-Yu Tong

2733

89

Production and Genetic Engineering of Terpenoids Production in Plant Cell and Organ Cultures Mercedes Bonfill, Sonia Malik, M. Hossein Mirjalili, Marta Goleniowski, Rosa Cusido, and Javier Palazön

2761

90 Taxol Producing Fungi Xiaoran Hao, Jiao Pan, and Xudong Zhu

2797

91 Metabolie Engineering of Isoprenoid Biosynthesis Anne Pribat, Lisa Boureau, Anne Mortain-Bertrand, Linda S. Bert, Dominique Rolin, Emeline Teyssier, and Philippe Gallusci

2813

92 Selection of Tomato Rieh in Nutritional Terpenes Jaime Cebolla-Cornejo, Salvador Rosello, and Fernando Nuez

2853

93 Volatile Oils from Marine Macroalgae Kasim Cemal Güven, Ekrem Sezik, Ferda Kaleagasioglu, Hüseyin Erdugan, Burak Coban, and Elif Karaka§

2883

94

Ecological Functions of Terpenoids in Changing Climates Jarmo K. Holopainen, Sari J. Himanen, J. S. Yuan, F. Chen, and C. Neal Stewart Jr.

2913

95

Hairy Root Culture: An Alternative Terpenoid Expression Platform Jocelvne Tremouillaux-Guiller

2941

Contents Part XI

xvii Terpenes: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution

96 Regulär Monoterpenes and Sesquiterpenes (Essential Oils) Remigius Chizzola 97 Monoterpenes: Iridoids Biswanath Dinda and Sudhan Debnath 98 Guaianolide Sesquiterpenoids: Pharmacology and Biosynthesis Henrik Toft Simonsen, Corinna Weitzel, and S0ren Br0gger Christensen 99 Biosynthesis and Production of Artemisinin: A Novel Class of Molecule Athar Ali, Mather Ali Khan, and Mailk Zainul Abdin 100

Nivalenol (Fungal Sesquiterpenes) Yoshiko Sugita-Konishi and Makoto Kimura

2971 2973 3009

3069

3099 3123

101 Taxol and Related Compounds Hojjat Sadeghi-aliabadi and Afsaneh Yegdaneh

3159

102

3173

Diterpenes for Therapeutic Use Virginia Lanzotti

103 Diterpene Sweeteners (Steviosides) Akula Ramakrishna and Gokare Aswathanarayana Ravishankar

3193

104 Triterpenoid Saponins: A Focus on Polygalaceae Marie-Aleth Lacaille-Dubois, Clement Delaude, and Anne-Claire Mitaine-Offer

3205

105 Plant Steroidal Saponins: A Focus on Open-Chain Glycosides Victoria L. Challinor and James J. De Voss 106 Tetraterpenes: Carotenoids Shinichi Takaichi

3225 3251

Volume 5 Part XII 107

Terpenes: Methods of Analysis

Essential Oils: Analytical Methods to Control the Quality of Perfumes Alberto Chisvert, Marina Löpez-Nogueroles, and

3285 3287

xviii

Contents

108 Methods for Analysis of Triterpenoid Saponins Jinlan Zhang and Feng Qu 109

Methods of Isolation and Analysis of Forskolin from Coleus forskohlii Mohamed Saleem A.

3311 < 3325

110 Quassinoids: Chemistry and Novel Detection Techniques Dipjyoti Chakraborty and Amita Pal

3345

111 Methods for Extraction and Analysis of Carotenoids Siti Machmudah and Motonobu Goto

3367

Part XIII

3413

112

Terpenes: Pharmacology and Bioavailability

Cannabinoids: Chemistry and Medicine Giovanni Appendino and Orazio Taglialatela-Scafati

3415

113 Phytosterols: Beneficial Effects Jonathan Santas, Rafael Codony, and Magda Rafecas

3437

114

Withanolides: Chemistry and Antitumor Activity M. Iqbal Choudhary, Sammer Yousuf, and Atta-ur-Rahman

3465

115

Pharmacology of Ginsenosides Kar Wah Leung

3497

116 Sesquiterpenes and Cytotoxicity Ajay Sharma, Vivek K. Bajpai, and Shruti Shukla 117 Tanshinones Against Cancer and Cardiovascular Diseases and their Biosynthesis Lixin Zhang and Xueting Liu

3515

3551

118 Strigolactones and Biological Activity Koichi Yoneyama, Xiaonan Xie, and Kaori Yoneyama

3583

119

Biological Activity of Oleuropein and its Derivatives Stefania Bulotta, Manuela Oliverio, Diego Russo, and Antonio Procopio

3605

120

Bacosides and Neuroprotection Sukanya Majumdar, Amrita Basu, Pijush Paul, Mihir Halder, and Sumita Jha

3639

121 Garlic and Cardiovascular Diseases Syed Haris Omar

3661

122

3697

Ginkgolides and Neuroprotective Effects Syed Haris Omar

Contents

*•*

123 Cardiac Glycosides and Anticancer Activity Yuan Lin, Dapeng Chen, Li Wang, and Dongmei Ye

3743

124 Terpenes and Improvement of Transdermal Drug Delivery .... 3757 Lifeng Kang, Vaddi Haranath Kumar, Perry Fung Chye Lim, Han Hui Cheong, and Sui Yung Chan 125 Quassinoids: Anticancer and Antimalarial Activities Emeline Houel, Didier Stien, Genevieve Bourdy, and Eric Deharo

3775

126 Glycyrrhizic Acid: Biological Effects on Glucose and Lipid Metabolism So Ha Ton, Chanchai Chandramouli, and Khalid BÄK

3803

127 Phytoecdysteroids: Phytochemistry and Pharmacological Activity Gert Laekeman and Arnold Vlietinck

3827

128 Brassinosteroids and their Biological Activities Jana Oklest'kovä, Lucie Rärovä, and Miroslav Strnad

3851

Part XIV

3873

Terpenes: Parapharmaceutical Uses

129 Lycopene in Cancer Prevention Kazim Sahin and Omer Kucuk

3875

130 Xanthophylls and the Eye Hannah E. Bartlett

3923

131 Triterpenoid Centellosides: Bioactivities and Uses in Healthcare Application Puziah Hashim

3959

132 Essential Oils as Antimicrobial Agents Vivek K. Bajpai, Shruti Shukla, and Ajay Sharma

3975

133 Menthol: Biological Effects and Toxicity Demetrius A. M. Araüjo, Darizy F. Silva, Humberto C. Joca, Jose H. Leal-Cardoso, and Jader S. Cruz

3989

134

4001

Eugenol as Local Anesthetic Gehoon Chung and Seog Bae Oh

135 Carotenoids as Colorants Bernardo Dias Ribeiro and Raquel Grando de Oliveira

4017

136 Oleoresins from Pine: Production and Industrial Uses Kelly Cristine da Silva Rodrigues-Correa, Jülio Cesar de

4037

xx

Contents

137 Pyrethrins and Synthetic Pyrethroids: Use in Veterinary Medicine Arturo Anadon, Irma Ares, Maria Aränzazu Martfnez, and Maria Rosa Marti'nez-Larranaga 138 Essential Oils in Insect Control Catherine Regnault-Roger 139

4061

4087

Biological Activities of Selected Mono- and Sesquiterpenes: Possible Uses in Medicine Gerhard Buchbauer and Anja Ilic

4109

Index

4161