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

1 Microbial Production of Plant Benzylisoquinoline Alkaloids ... 3 Eitaro Matsumura, Motoki Matsuda, Fumihiko Sato, and Hiromichi Minami

2 Alkaloids of Marine Macroalgae 25 Kasim Cemal Güven, Burak Coban, Ekrem Sezik, Hiiseyin Erdugan, and Ferda Kaleagasioglu

3 Neurotoxic Alkaloids from Cyanobacteria 39 Ralf Kellmann, Olivier Ploux, and Brett A. Neilan

4 Bioproduction of Terpenoid Indole Alkaloids from Catharanthus roseus Cell Cultures 85 Lorena Almagro, Mariana Sottomayor, and Maria Angeles Pedreno

5 Bioactive Alkaloids from South American Psychotria and Related Rubiaceae 119 Helio Nitta Matsuura, Diogo Denardi Porto, and Arthur Germano Fett-Neto

6 Ecological Role of Alkaloids 149 Shaily Goyal

7 Plant In Vitro Systems as Sources of Tropane Alkaloids 173 Vasil Georgiev, Andrey Marchev, Strahil Berkov, and Atanas Pavlov

8 Biotechnology and Genetic Engineering for Alkaloid Production 213 Smita Srivastava and Ashok Kumar Srivastava

9 Marine Pyrroloitninoquinone Alkaloids, Makaluvamines and Discorhabdins, and Marine Pyrrole-Imidazole Alkaloids 251 Hiromichi Fujioka and Yasuyuki Kita

>v

X Contents

10 Internet Natural Product Trade, Business, and Risk of Damaged and/or Contaminated Products 285 Maria Laura Colombo, Maria Teresa Pinorini, and Ario Conti

Part II Alkaloids: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution 301

11 Alkaloids Derived from Lysine: Piperidine Alkaloids 303 Eva Szoke, Eva Lemberkovics, and Läszlo Kursinszki

12 Alkaloids Derived from Ornithine: Tropane Alkaloids 343 Stefan Philipov and Tsvetelina Doncheva

13 Alkaloids Derived From Ornithine: Pyrrolizidine Alkaloids .... 359 Helmut Wiedenfeld

14 Alkaloids Derived from Lysine: Quinolizidine (a Focus on Lupin Alkaloids) 381 Giovanna Boschin and Donatella Resta

15 Alkaloids Derived from Tyrosine: Modified Benzyltetrahydroisoquinoline Alkaloids 405 Feroz Khan, Tabish Qidwai, Rakesh K. Shukla, and Vikrant Gupta

16 Alkaloids Derived from Tyrosine: Penethylisoquinoline (Autumnaline, Colchicine) 461 Pijush Paul, Mihir Halder, and Sumita Jha

17 Amaryllidaceae Alkaloids 479 Zhong Jin and Xiao-Hua Xu

18 Bioactive Alkaloids from Fungi: Psilocybin 523 Zafar Alam Mahmood

19 Alkaloids Derived from Tryptophan: Harmine and Related Alkaloids 553 T. D. Nikam, K. M. Nitnaware, and M. L. Ahire

20 Alkaloids Derived from Tryptophan: Terpenoid Indole Alkaloids 575 Shilpa Ramani, Nandadevi Patil, Suhas Nimbalkar, and Chelliah Jayabaskaran

21 Chemistry and Biology of Cinchona Alkaloids 605 Karol Michal Kacprzak

22 Chemistry and Biology of Camptothecin and its Derivatives 643

Contents xi

23 Alkaloids Derived from Tryptophan: A Focus on Ergot Alkaloids 683 Peter Mai and Shu-Ming Li

24 Alkaloids Derived from Anthranilic Acid: Quinoline, Acridone, and Quinazoline 715 Maria Fätima das Grabas Fernandes da Silva, Joäo Batista Fernandes, Moacir Rossi Forim, Paulo Cezar Vieira, and Israel Civico Gil de Sä

25 Alkaloids Derived from Histidine: Imidazole (Pilocarpine, Pilosine) 861 Ana Paula Santos and Paulo Roberto H. Moreno

26 Alkaloids Derived by Amination Reaction: Acetate-Derived (Coniine) 883 Rumen Binev

27 Ephedra Alkaloids-Alkaloids Derived by Amination Reaction: Phenylalanine Derived 909 Ali Parsaeimehr and Elmira Sargsyan

28 Terpenoid Alkaloids Derived by Amination Reaction 923 Krishna Prasad Devkota and Norbert Sewald

29 Purine Alkaloids, Cytokinins, and Purine-Like Neurotoxin Alkaloids 953 Hiroshi Ashihara, Takao Yokota, and Alan Crozier

30 Aziridine Alkaloids: Origin, Chemistry and Activity 977 Valery M. Dembitsky, Alexander O. Terent'ev, and Dmitri O. Levitsky

Volume 2

Part III Alkaloids: Methods of Analysis 1007

31 Methods of Analysis: Tropane Alkaloids from Plant Origin 1009 Philippe Christen, Stefan Bieri, and Strahil Berkov

32 Methods for Analysis of Pyrrolizidine Alkaloids 1049 Colin Crews

33 Methods of Analysis of Opium Alkaloids 1069 Carmen Cruces-Blanco. Diego Airado-Rodrfeuez. and

xiv Contents

59 Flavones and Flavonols: Phytochemistry and Biochemistry 1821 Qiang Zhang, Xinhuai Zhao, and Hongbin Qiu

60 Isoflavonoids 1849 Varsha Sharma and Kishan G. Ramawat

61 Minor Flavonoids (Chalcones, Flavanones, Dihydrochalcones, and Aurones) Masayuki Ninomiya and Mamoru Koketsu

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

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

64 Hydrolyzable Tannins: Gallotannins and Ellagitannins 1975 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 2013 Winny Routray and Valerie Orsat

66 Mass Spectrometric Detection of Phenolic Acids 2047 Santi M. Mandal and Dipjyoti Chakraborty

67 Analytical Methods of Phenolic Compounds 2061 Ioana Ignat, Irina Volf, and Valentin I. Popa

68 Phenolic Compounds in Catharanthus roseus 2093 David M. Pereira, Patricia Valentäo, Mariana Sottomayor, Federico Ferreres, and Paula B. Andrade

69 Flavonoids by HPLC 2107 S. W. Annie Bligh, Olumuyiwa Ogegbo, and Zheng-Tao Wang

70 Polyphenol Purification by Solid Support-Free Liquid-Liquid Chromatography (CCC, CPC) 2145 Jane Hubert, Karen Ple, Mahmoud Hamzaoui, and Jean-Hugues Renault

Part VIII Phenolics: Biological Activity and Bioavailability 2173

71 Cellular, Molecular, and Biological Perspective of Polyphenols in Chemoprevention and Therapeutic Adjunct in Cancer 2175 Sanieev Baneriee and Paulrai Raiamani

1867

1901

1951

Contents xv

72 Tannins and Anthocyanins of Wine: Phytochemistry and Organoleptic Properties 2255 Pierre-Louis Teissedre and Michael Jourdes

73 Grapevine Stilbenoids: Bioavailability and Neuroprotection 2275 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 2311 Manuel Rusconi, Maria Teresa Pinorini, and Ario Conti

75 Polyphenols and Beer Quality 2333 Sonia Collin, Vesna Jerkovic, M. Bröhan, and D. Callemien

76 Wine Polyphenols and Vascular Protective Effects 2361 Cyril Auger and Valerie B. Schini-Kerth

77 Isoflavonoids and Phytoestrogenic Activity 2381 Catherine Bennetau-Pelissero

78 Phenolics in Human Nutrition: Importance of the Intestinal Microbiome for Isoflavone and Lignan Bioavailability 2433 Thomas Clavel and Job O. Mapesa

79 Bioavailability of Anthocyanins 2465 Ana Faria, Iva Fernandes, Nuno Mateus, and Concei§äo Calhau

Volume 4

Part IX Phenolics: Nutraceuticals and Functional Foods 2489

80 Prospects of Functional Foods/Nutraceuticals and Markets 2491 Josep Valls, Nacho Pasamontes, Albert Pantaleon, Susana Vinaixa, Montse Vaque, Arantza Soler, Silvia Millän, and Xavier Gomez

81 Food Sources of Phenolics Compounds 2527 Wende Li and Trust Beta

82 Nutraceuticals and Antioxidants in Prevention of Diseases 2559 Neelam Jain and Kishan G. Ramawat

83 Functional Grapes 2581 Maria Isabel Fernändez-Marin, Raul F. Guerrero, Belen Puertas,

xii Contents

34 Analysis of Catharanthus Alkaloids 1121 Qinhua Chen and Zilin Chen

35 Methods for Analysis of Ergot Alkaloids 1133 Colin Crews

36 Analysis of Alkaloids by Capillary Electrophoresis 1153 Roberto Gotti

Part IV Alkaloids: Pharmacology 1201

37 Pharmacology of Macroalgae Alkaloids 1203 Ferda Kaleagasioglu, Kasim Cemal Güven, Ekrem Sezik, Hüseyin Erdugan, and Burak Coban

38 Pharmacological Effects of Ephedrine 1217 Renata Pereira Limberger, Ana Laura Bemvenuti Jacques, Gabriela Cristina Schmitt, and Marcelo Dutra Arbo

39 Lycopodium Alkaloids: Pharmacology 1239 Elfn Soffia Olafsdottir, Elsa S. Halldorsdottir, N. M. Pich, and S. Omarsdottir

40 Scope of Alkaloids in Antileishmanial Drug Discovery and Development 1263 Bhuwan B. Mishra, Navneet Kishore, Rakesh K. Singh, and Vinod Kumar Tiwari

41 Pharmacological/Biological Effects of Berberine 1301 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 1331 Melanie-Jayne R. Howes

43 Opioids and Pain Treatment 1367 Daniel Krashin, Andrea Trescot, and Natalia Murinova

44 Pyrrolizidine Alkaloid-Induced Toxicity to the Liver 1383 Manuela G. Neuman

45 Biological Activities of Pepper Alkaloids 1397 Krishnapura Srinivasan

46 Antiangiogenic Alkaloids from Plants 1439 Flavia Cristine Mascia Lopes, Luis Octävio Regasini, Manuel Nuno de Magalhäes Pinheiro Algada, and Raquel Soares

47 Prevention of Brain Disorders by Nicotine 1469 Karim Alkadhi, Samina Salim, and Karem Aizoubi

Contents xlii

48 Aconitum Alkaloids and Biological Activities 1503 Ainura Chodoeva, Jean-Jacques Bosc, and Jacques Robert

49 Alkaloids and Inhibitory Effects Against Enzymes Linked to Neurodegenerative Diseases (Physostigmine, Galanthamine, Huperzine, etc.) 1525 Ilkay Erdogan Orhan and F. Sezer Senol

Part V Phenolics: General Biology and Biotechnology 1541

50 Phenolic Compounds: Introduction 1543 Vincenzo Lattanzio

51 Metabolie Engineering for Functional Foods: Tomato Fruits and Stilbenes 1581 Giovanna Giovinazzo, Ilaria Ingrosso, Marco Taurino, and Angelo Santino

52 Cocoa Cultivation, Directed Breeding and Polyphenolics 1599 Reinhard Lieberei, Daniel Kadow, and David Seigier

53 Genetics of Flavonoids 1617 Ramesh Prasad Pandey and Jae Kyung Sohng

54 Isoflavonoid Production by Genetically Engineered Microorganisms 1647 Brady F. Cress, Robert J. Linhardt, and Mattheos A. G. Koffas

55 Bioproduction of fra/is-Resveratrol from Grapevine Cell Cultures 1683 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 1715 Tahira Fatima, Avtar K. Handa, and Autar K. Mattoo

Volume 3

Part VI Phenolics: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution 1751

57 Flavanols: Catechins and Proanthocyanidins 1753 Joana Oliveira, Nuno Mateus, and Victor de Freitas

58 Anthocyanins 1803 Sonia de Pascual-Teresa, Maria Teresa Sanchez-Ballesta, and Cristina Garcia-Viguera

xvi Contents

84 Potential Neuroprotective Actions of Dietary Flavonoids 2617 David Vauzour, Marcus Rattray, Robert J. Williams, and Jeremy P. E. Spencer

85 Improvement of Nutraceutical Value of Food by Plant Symbionts 2641 Manuela Giovannetti, Luciano Avio, and Cristiana Sbrana

Part X Terpenes: General Biology and Biotechnology 2663

86 Terpenes: Chemistry, Biological Role, and Therapeutic Applications 2665 Priyanka P. Brahmkshatriya and Pathik S. Brahmkshatriya

87 Biosynthesis of Terpenoids 2693 Nelson L. Brock and Jeroen S. Dickschat

88 Biotransformation of Terpenoids and Steroids 2733 Wang-Yu Tong

89 Production and Genetic Engineering of Terpenoids Production in Plant Cell and Organ Cultures 2761 Mercedes Bonfill, Sonia Malik, M. Hossein Mirjalili, Marta Goleniowski, Rosa Cusido, and Javier Palazön

90 Taxol Producing Fungi 2797 Xiaoran Hao, Jiao Pan, and Xudong Zhu

91 Metabolie Engineering of Isoprenoid Biosynthesis 2813 Anne Pribat, Lisa Boureau, Anne Mortain-Bertrand, Linda S. Bert, Dominique Rolin, Emeline Teyssier, and Philippe Gallusci

92 Selection of Tomato Rieh in Nutritional Terpenes 2853 Jaime Cebolla-Cornejo, Salvador Rosello, and Fernando Nuez

93 Volatile Oils from Marine Macroalgae 2883 Kasim Cemal Güven, Ekrem Sezik, Ferda Kaleagasioglu, Hüseyin Erdugan, Burak Coban, and Elif Karaka§

94 Ecological Functions of Terpenoids in Changing Climates 2913 Jarmo K. Holopainen, Sari J. Himanen, J. S. Yuan, F. Chen, and C. Neal Stewart Jr.

95 Hairy Root Culture: An Alternative Terpenoid Expression Platform 2941 Jocelvne Tremouillaux-Guiller

Contents xvii

Part XI Terpenes: Classes - Occurrence, Biosynthesis, Structure and Chemistry, Distribution 2971

96 Regulär Monoterpenes and Sesquiterpenes (Essential Oils) 2973 Remigius Chizzola

97 Monoterpenes: Iridoids 3009 Biswanath Dinda and Sudhan Debnath

98 Guaianolide Sesquiterpenoids: Pharmacology and Biosynthesis 3069 Henrik Toft Simonsen, Corinna Weitzel, and S0ren Br0gger Christensen

99 Biosynthesis and Production of Artemisinin: A Novel Class of Molecule 3099 Athar Ali, Mather Ali Khan, and Mailk Zainul Abdin

100 Nivalenol (Fungal Sesquiterpenes) 3123 Yoshiko Sugita-Konishi and Makoto Kimura

101 Taxol and Related Compounds 3159 Hojjat Sadeghi-aliabadi and Afsaneh Yegdaneh

102 Diterpenes for Therapeutic Use 3173 Virginia Lanzotti

103 Diterpene Sweeteners (Steviosides) 3193 Akula Ramakrishna and Gokare Aswathanarayana Ravishankar

104 Triterpenoid Saponins: A Focus on Polygalaceae 3205 Marie-Aleth Lacaille-Dubois, Clement Delaude, and Anne-Claire Mitaine-Offer

105 Plant Steroidal Saponins: A Focus on Open-Chain Glycosides 3225 Victoria L. Challinor and James J. De Voss

106 Tetraterpenes: Carotenoids 3251 Shinichi Takaichi

Volume 5

Part XII Terpenes: Methods of Analysis 3285

107 Essential Oils: Analytical Methods to Control the Quality of Perfumes 3287 Alberto Chisvert, Marina Löpez-Nogueroles, and

xviii Contents

108 Methods for Analysis of Triterpenoid Saponins 3311 Jinlan Zhang and Feng Qu

< 109 Methods of Isolation and Analysis of Forskolin from

Coleus forskohlii 3325 Mohamed Saleem A.

110 Quassinoids: Chemistry and Novel Detection Techniques 3345 Dipjyoti Chakraborty and Amita Pal

111 Methods for Extraction and Analysis of Carotenoids 3367 Siti Machmudah and Motonobu Goto

Part XIII Terpenes: Pharmacology and Bioavailability 3413

112 Cannabinoids: Chemistry and Medicine 3415 Giovanni Appendino and Orazio Taglialatela-Scafati

113 Phytosterols: Beneficial Effects 3437 Jonathan Santas, Rafael Codony, and Magda Rafecas

114 Withanolides: Chemistry and Antitumor Activity 3465 M. Iqbal Choudhary, Sammer Yousuf, and Atta-ur-Rahman

115 Pharmacology of Ginsenosides 3497 Kar Wah Leung

116 Sesquiterpenes and Cytotoxicity 3515 Ajay Sharma, Vivek K. Bajpai, and Shruti Shukla

117 Tanshinones Against Cancer and Cardiovascular Diseases and their Biosynthesis 3551 Lixin Zhang and Xueting Liu

118 Strigolactones and Biological Activity 3583 Koichi Yoneyama, Xiaonan Xie, and Kaori Yoneyama

119 Biological Activity of Oleuropein and its Derivatives 3605 Stefania Bulotta, Manuela Oliverio, Diego Russo, and Antonio Procopio

120 Bacosides and Neuroprotection 3639 Sukanya Majumdar, Amrita Basu, Pijush Paul, Mihir Halder, and Sumita Jha

121 Garlic and Cardiovascular Diseases 3661 Syed Haris Omar

122 Ginkgolides and Neuroprotective Effects 3697 Syed Haris Omar

Contents *•*

123 Cardiac Glycosides and Anticancer Activity 3743 Yuan Lin, Dapeng Chen, Li Wang, and Dongmei Ye

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 3775 Emeline Houel, Didier Stien, Genevieve Bourdy, and Eric Deharo

126 Glycyrrhizic Acid: Biological Effects on Glucose and Lipid Metabolism 3803 So Ha Ton, Chanchai Chandramouli, and Khalid BÄK

127 Phytoecdysteroids: Phytochemistry and Pharmacological Activity 3827 Gert Laekeman and Arnold Vlietinck

128 Brassinosteroids and their Biological Activities 3851 Jana Oklest'kovä, Lucie Rärovä, and Miroslav Strnad

Part XIV Terpenes: Parapharmaceutical Uses 3873

129 Lycopene in Cancer Prevention 3875 Kazim Sahin and Omer Kucuk

130 Xanthophylls and the Eye 3923 Hannah E. Bartlett

131 Triterpenoid Centellosides: Bioactivities and Uses in Healthcare Application 3959 Puziah Hashim

132 Essential Oils as Antimicrobial Agents 3975 Vivek K. Bajpai, Shruti Shukla, and Ajay Sharma

133 Menthol: Biological Effects and Toxicity 3989 Demetrius A. M. Araüjo, Darizy F. Silva, Humberto C. Joca, Jose H. Leal-Cardoso, and Jader S. Cruz

134 Eugenol as Local Anesthetic 4001 Gehoon Chung and Seog Bae Oh

135 Carotenoids as Colorants 4017 Bernardo Dias Ribeiro and Raquel Grando de Oliveira

136 Oleoresins from Pine: Production and Industrial Uses 4037 Kelly Cristine da Silva Rodrigues-Correa, Jülio Cesar de

xx Contents

137 Pyrethrins and Synthetic Pyrethroids: Use in Veterinary Medicine 4061 Arturo Anadon, Irma Ares, Maria Aränzazu Martfnez, and Maria Rosa Marti'nez-Larranaga

138 Essential Oils in Insect Control 4087 Catherine Regnault-Roger

139 Biological Activities of Selected Mono- and Sesquiterpenes: Possible Uses in Medicine 4109 Gerhard Buchbauer and Anja Ilic

Index 4161