Natural products phytochemistry botany and metabolism of alkaloids phenolics and terpenes 1

Natural Products



Kishan Gopal Ramawat
Jean-Michel Me´rillon
Editors

Natural Products
Phytochemistry, Botany
and Metabolism of Alkaloids,
Phenolics and Terpenes

With 1569 Figures and 307 Tables


Editors-in-Chief:
Kishan Gopal Ramawat
Botany Department, M.L. Sukhadia University
Udaipur 313001
India
Jean-Michel Me´rillon
Biological-Active Plant Substances Study Group
University of Bordeaux
Institute of Vine and Wine Sciences
Villenave d’Ornon
France

ISBN 978-3-642-22143-9
ISBN 978-3-642-22144-6 (eBook)

ISBN 978-3-642-22145-3 (Print and electronic bundle)
DOI 10.1007/ 978-3-642-22144-6
Springer Heidelberg New York Dordrecht London
Library of Congress Control Number: 2013934974
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Preface

We are pleased to present a five volume treatise on “Natural products:

phytochemistry, botany and metabolism”. Natural products are as diverse as plant
biodiversity and it was a herculean task to bring together several hundred leading
scientists distributed all over the world to contribute in this project.
This five volumes work on Natural Products is reference work providing
state-of-the-art knowledge composed by highly renowned scientists in their field.
The book is intended to serve the needs of graduate students, Ph.D. scholars,
researchers in the field of phytochemistry, botany, agricultural sciences, pharmacy,
nutrition, biotechnology and, industrial scientists and those involved in marketing
phytochemicals, plants and their extracts. The present reference work will
encompass the information about well established phytochemicals, biology and
biotechnology of medicinal plants or their products, their biosynthesis, novel
production strategies, demand and uses, metabolism and bioavailability. This
book is a work of tertiary literature containing digested knowledge in an easily
accessible format.
Use of medicinal plants is as old as human civilization and continuous efforts are
being made to explore new and old medicinal plants for novel bioactive molecules
or to produce these products in high amounts through modern technologies. About
200,000 natural products of plant origin are known and many more are being
identified from higher plants and micro-organisms. Some plants based drugs are
used since centuries and there are not many alternatives for some natural drugs as
cardiac glycosides or morphine. Various facets of bioactive molecules have
developed very rapidly in the last two decades particularly due to newer tools of
isolation and identification as well as refined molecular techniques to establish the
biological properties of isolated molecules. This endeavour is to timely compile this
vast data generated in recent past. This is well reflected in 139 chapters running in
over 4000 pages of text and vast literature cited in each chapter. The readers will
find comprehensive information on almost all bioactive molecules. While planning
this book our endeavour was to incorporate articles that cover the entire gamut of
bioactive molecules of all the three major classes, viz., alkaloids, phenolics and
terpenes. Each volume is further divided into sections such as General Biology and

Biotechnology; Classes - Occurrence, Biosynthesis, Structure and Chemistry,
v


vi

Preface

Distribution; Methods of Analysis; (para) Pharmacology and Bioavailability; and
Nutraceuticals and Functional Foods (in phenolics).
Some examples are sufficient to illustrate the spectrum of chapters in different
sections such as: on alkaloids (Biotechnology and genetic engineering for alkaloid
production, various classes of alkaloids e.g., Purine alkaloids, Ergot alkaloids,
Terpenoid indole alkaloids, Pharmacological effects of ephedrine, Lycopodium
alkaloids, Biological activities of pepper alkaloids, Neurotoxic alkaloids from
cyanobacteria, Prevention of brain disorders by nicotine, Opioids and pain
treatment, Ecological roles of alkaloids); on phenolics (Genetics of flavonoids,
Functional foods: Genetics, metabolome and engineering, phytonutrient levels,
Cocoa cultivation, directed breeding and polyphenolics, classes of phenolics,
Polyphenols and anticancer activity, Tannins and anthocyanins of wine:
phytochemistry and organoleptic properties, Polyphenols and beer quality, Wine
polyphenols and vascular protective effects, Isoflavonoids and phytoestrogenic
activity, Functional grapes, Potential neuroprotective actions of dietary flavonoids,
Prospects of functional foods / nutraceuticals and markets), and on terpenes (Terpenes: Chemistry, biological role and therapeutic applications, Biotransformation
of terpenoids and steroids, Production and genetic engineering of terpenoids production in plant cell cultures and organ cultures, Taxol-producing fungi, Metabolic
engineering of isoprenoids biosynthesis, classes of terpenes, Cannabinoids: Chemistry and Medicine, Phytosterols: Beneficial effects, Ginsenosides: Biological
activities, Ginkgolides and neuroprotective effects, Quassinoids: Anti-cancer and
antimalarial activities, Phytoecdysteroids: phytochemistry and pharmacological
activity, Brassinosteroids and their biological activity, and so on).
These compounds exhibit various ecological functions, provide protection

against attack by herbivores and microbes, and serve as attractants for pollinators
and seed-dispersing agents. Natural products are explored as sources of drugs,
flavouring agents, fragrances and for a wide range of therapies. Rapid progress
has been made in recent years in understanding natural product accumulation and
synthesis, and regulation and functions. It is timely to bring this information
together with contemporary advances in chemistry, plant biology, ecology, and
pharmacology and metabolism of natural products in the form of a comprehensive
treatise on natural products.
Because of the voluminous work for the treatise, this project was spread over
almost two years, from concept to print. We would like to acknowledge
cooperation, patient and support of our contributors who have put their serious
efforts to ensure the high scientific quality of this book with up to date information.
This work could not be completed without active support of Springer team who
took pains in streamlining the production process. We are particularly indebt to
Drs. Marion Hertel, Lydia Muller, Sylvia Blago and Simone Giesler for their
continuous support from very inception of the project.
March 2013

K. G. Ramawat
J.-M. Me´rillon


About the Editors

Professor (Dr.) K. G. Ramawat, Former Professor & Head Botany Department,
M.L. Sukhadia University, Udaipur, India
Professor K. G. Ramawat did his Ph.D. (1978, Plant Biotechnology) from the
University of Jodhpur, India and joined as faculty member in January 1979.
He joined M.L.Sukhadia University as Associate Professor in 1991 and became
Professor in 2001. He served as Head, Department of Botany (2001-2004,

2010-2012), In charge, Department of Biotechnology (2003-2004), member task
force on medicinal and aromatic plants, Department of Biotechnology, Government
of India, New Delhi (2002-2005) and co-ordinator UGC-DRS and DST-FIST
programmes (2002-2012). He did his Post-doctoral at the University of Tours,
France (1983-85) and subsequently worked as visiting professor at University of
Tours (1991) and University of Bordeaux2, France (1995, 1999, 2003, 2006, 2010).
He visited Poland under INSA-PAN academic exchange programme (2005).
During last 38 years of his career, he has published more than 170 peer reviewed
papers and articles. He has edited books on Biotechnology of medicinal plants,
secondary metabolites, Bioactive molecules, Herbal drugs, Plant defence:
biological control, Desert plants; published by Science Publishers Inc, Enfield,
USA and Springer Verlag, Germany. His research on recalcitrant woody legume
trees of desert (Prosopis, Zizyphus, Commiphora), production of useful metabolites
vii


viii

About the Editors

from woody plants (Comiphora, Pueraria) was funded by UGC, CSIR, ICAR, DBT
and DST, New Delhi. Works related to use of novel growth modulators and elicitors
on the production of guggulsterones, stibenes and isoflvonoids are well cited.
He has supervised doctoral thesis of 25 students. He is member of several academic
bodies, associations and editorial boards of journals.

Professeur Jean-Michel Me´rillon, Directeur de l’EA 3675 (Groupe d’Etude des
Substances Ve´ge´tales a` Activite´ Biologique + Polyphe´nols Biotech), Faculte´ de
Pharmacie, Universite´ de Bordeaux, Institut des Sciences de la Vigne et du Vin,
Villenave d’Ornon, France

Professor J.M. Me´rillon received his M.Pharma. (1979) and Ph.D. (1984) from the
University of Tours in France. He joined the University of Tours as assistant professor
in 1981, became associate professor in 1987, and a full professor in 1993 at the faculty
of Pharmacy, University of Bordeaux, France. He is currently group leader of a “study
group on biologically active plant substances” at the Institute of Vine and Wine
Sciences, which comprises 25 scientists and research students. His group has worked
for many years on phenolic compounds from vine and wine, mainly complex
stilbenes and their involvement in health. He has supervised the doctoral theses of
18 students. He has published more than 125 research papers in internationally
recognized journals. He has an H index of 29 according to the analysis of documents
published between 1996 and 2013. He has co-edited four books on secondary metabolites and biotechnology (Science Publishers, USA; Springer, Germany). He is
involved in developing teaching on plant biology, natural bioactive compounds and
biotechnology. He has traveled widely as a senior professor. Scientists from several
countries are working in his laboratory and his research is supported by funding from
the Aquitaine Regional Government, the Ministry of Higher Education and Research,
and various private companies. He founded a technology transfer unit in 2004,
Polyphenols Biotech, providing support for R&D programs for SMEs and major
groups from the cosmetic, pharmaceutical, agricultural and health-nutrition sectors.


Contents

Volume 1
Part I Alkaloids: General Biology and Biotechnology . . . . . . . . . . .

1

1

Microbial Production of Plant Benzylisoquinoline Alkaloids . . .

Eitaro Matsumura, Motoki Matsuda, Fumihiko Sato, and
Hiromichi Minami

3

2

Alkaloids of Marine Macroalgae . . . . . . . . . . . . . . . . . . . . . . . . .
Kasım Cemal G€
uven, Burak Coban, Ekrem Sezik,
H€
useyin Erdugan, and Ferda Kaleag˘asıog˘lu

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 Pedren˜o

85

Bioactive Alkaloids from South American Psychotria and Related
Rubiaceae . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
He´lio Nitta Matsuura, Diogo Denardi Porto, and Arthur Germano
Fett-Neto

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

213

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

251

5

9

ix


x

Contents

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 . . . . . . . . .
E´va Szo˝ke, E´va Lemberkovics, and La´szlo´ Kursinszki

303

12

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

343

13

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

359

14

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

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

553

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

575

21

Chemistry and Biology of Cinchona Alkaloids
Karol Michał Kacprzak

..............

605

22

Chemistry and Biology of Camptothecin and its
Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Karol Michał Kacprzak

643

15

16

20


Contents

23

24

25

xi

Alkaloids Derived from Tryptophan: A Focus on
Ergot Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Peter Mai and Shu-Ming Li
Alkaloids Derived from Anthranilic Acid: Quinoline,
Acridone, and Quinazoline . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Maria Fa´tima das Grac¸as Fernandes da Silva, Joa˜o Batista
Fernandes, Moacir Rossi Forim, Paulo Cezar Vieira, and
Israel Cı´vico Gil de Sa´

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

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

909

28

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

923

29

Purine Alkaloids, Cytokinins, and Purine-Like Neurotoxin

Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Hiroshi Ashihara, Takao Yokota, and Alan Crozier

953

26

27

30

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

.........

977

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-Rodrı´guez, and
Ana M. Garcı´a-Campan˜a


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 Kaleag˘asıog˘lu, Kasım Cemal G€
uven, Ekrem Sezik,
H€
useyin 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

Elı´n Soffı´a Olafsdo´ttir, 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. Nun˜ez, 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
Fla´via Cristine Mascia Lopes, Luis Octa´vio Regasini,
Manuel Nuno de Magalha˜es Pinheiro Alc¸ada, and Raquel Soares

47

Prevention of Brain Disorders by Nicotine . . . . . . . . . . . . . . . . . 1469
Karim Alkadhi, Samina Salim, and Karem Alzoubi


Contents

xiii

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

Metabolic 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 Seigler

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 trans-Resveratrol from Grapevine
Cell Cultures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1683
Lorena Almagro, Sarai Belchı´-Navarro, Ana Bele´n Sabater-Jara,
Juan Carlos Vera-Urbina, Susana Selle´s-Marchart,
Roque Bru, and Marı´a Angeles Pedren˜o

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 Garcı´a-Viguera


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) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1867
Masayuki Ninomiya and Mamoru Koketsu

62

Stilbenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1901
Tao Shen, Chun-Feng Xie, Xiao-Ning Wang, and
Hong-Xiang Lou

63

Phenolic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1951
Marta Goleniowski, Mercedes Bonfill, Rosa Cusido, and
Javier Palazo´n

64

Hydrolyzable Tannins: Gallotannins and Ellagitannins
Michae¨l Jourdes, Laurent Pouyse´gu, Denis Deffieux,
Pierre-Louis Teissedre, and Ste´phane Quideau

Part VII

. . . . . . . 1975

Phenolics: Methods of Analysis . . . . . . . . . . . . . . . . . . . . .

2011

65

Preparative Extraction and Separation of
Phenolic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2013
Winny Routray and Vale´rie 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, Patrı´cia Valenta˜o, 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
71

Phenolics: Biological Activity and Bioavailability . . . . . .

2173

Cellular, Molecular, and Biological Perspective of Polyphenols
in Chemoprevention and Therapeutic Adjunct in Cancer . . . . . 2175
Sanjeev Banerjee and Paulraj Rajamani


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-Te´guo, Ste´phanie Krisa, Alison D. Pawlus,
Tristan Richard, Jean-Pierre Monti, and Jean-Michel Me´rillon

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. Br€
ohan, and D. Callemien

76

Wine Polyphenols and Vascular Protective Effects . . . . . . . . . . . 2361
Cyril Auger and Vale´rie 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 Conceic¸a˜o 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 Pantaleo´n,
Susana Vinaixa, Montse Vaque´, Arantza Soler,
Silvia Milla´n, and Xavier Go´mez

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 Ferna´ndez-Marı´n, Rau´l F. Guerrero, Bele´n Puertas,
Marı´a Carmen Garcı´a-Parrilla, and Emma Cantos-Villar


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 Palazo´n

90

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

91

Metabolic 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 Rich in Nutritional Terpenes . . . . . . . . . . . . 2853
Jaime Cebolla-Cornejo, Salvador Rosello´, and Fernando Nuez

93

Volatile Oils from Marine Macroalgae . . . . . . . . . . . . . . . . . . . . 2883
Kasım Cemal G€
uven, Ekrem Sezik, Ferda Kaleag˘asıog˘lu,
H€
useyin Erdugan, Burak Coban, and Elif Karakas¸

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

Jocelyne Tre´mouillaux-Guiller


Contents

Part XI

xvii

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

2971

96

Regular 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 Søren Brøgger

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, Cle´ment 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
Shinichi Takaichi

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3251

Volume 5
Part XII
107

Terpenes: Methods of Analysis . . . . . . . . . . . . . . . . . . . . .

3285

Essential Oils: Analytical Methods to Control the Quality
of Perfumes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3287
Alberto Chisvert, Marina Lo´pez-Nogueroles, and
Amparo Salvador

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 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 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

. . . . . . . . . . . . . 3311

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
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

. . . . . . . . . 3605


Contents

xix

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 Houe¨l, Didier Stien, Genevie`ve Bourdy, and
Eric Deharo

126

Glycyrrhizic Acid: Biological Effects on Glucose and
Lipid Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3803

So Ha Ton, Chanchal Chandramouli, and Khalid BAK

127

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

128

Brassinosteroids and their Biological Activities . . . . . . . . . . . . . . 3851
Jana Oklesˇt0 kova´, Lucie Ra´rova´, 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
Deme´trius A. M. Arau´jo, 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-Correˆa, Ju´lio Ce´sar de

Lima, and Arthur Germano Fett-Neto


xx

Contents

137

Pyrethrins and Synthetic Pyrethroids: Use in
Veterinary Medicine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4061
Arturo Anado´n, Irma Are´s, Marı´a Ara´nzazu Martı´nez, and
Marı´a Rosa Martı´nez-Larran˜aga

138

Essential Oils in Insect Control
Catherine Regnault-Roger

139

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

. . . . . . . . . . . . . . . . . . . . . . . . . . 4087

Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4161

List of Contributors

Mailk Zainul Abdin Department of Biotechnology, Faculty of Science, Centre
for Transgenic Plant Development, Jamia Handard University, New Delhi, India
M. L. Ahire Department of Botany, University of Pune, Pune, MS, India
Diego Airado-Rodrı´guez Department of Analytical Chemistry, Faculty of
Sciences, University of Granada, Granada, Spain
Manuel Nuno de Magalha˜es Pinheiro Alc¸ada Department of Biochemistry
(U38/FCT), Faculty of Medicine, University of Porto, Porto, Portugal
Athar Ali Department of Biotechnology, Faculty of Science, Centre for Transgenic Plant Development, Jamia Handard University, New Delhi, India
Karim Alkadhi Department of Pharmacological and Pharmaceutical Sciences,
University of Houston, College of Pharmacy, Houston, TX, USA
Lorena Almagro Department of Plant Biology, Faculty of Biology, University of
Murcia, Murcia, Spain
Karem Alzoubi Department of Clinical Pharmacy, Faculty of Pharmacy, Jordan
University of Science and Technology, Irbid, Jordan
Arturo Anado´n Departamento de Toxicologı´a y Farmacologı´a, Facultad de
Veterinaria, Universidad Complutense de Madrid, Madrid, Spain
Paula B. Andrade REQUIMTE/Laborato´rio de Farmacognosia, Departamento de
Quı´mica, Faculdade de Farma´cia, Universidade do Porto, Porto, Portugal
Maria Angeles Pedren˜o Department of Plant Biology, Faculty of Biology,
University of Murcia, Murcia, Spain
Giovanni Appendino Dipartimento di Scienze Chimiche, Alimentari,
Farmaceutiche e Farmacologiche, Universita` del Piemonte Orientale, Novara, Italy
Deme´trius A. M. Arau´jo Departamento de Biotecnologia, Centro de
Biotecnologia, Universidade Federal da Paraı´ba, Joa˜o Pessoa, PB, Brazil
Marcelo Dutra Arbo REQUIMTE, Laborato´rio de Toxicologia, Departamento de
Cieˆncias Biolo´gicas, Universidade do Porto, Porto, Portugal
xxi

xxii

List of Contributors

Irma Are´s Departamento de Toxicologı´a y Farmacologı´a, Facultad de
Veterinaria, Universidad Complutense de Madrid, Madrid, Spain
Hiroshi Ashihara Department of Biological Sciences, Ochanomizu University,
Tokyo, Japan
Cyril Auger UMR CNRS 7213 – Laboratoire de Biophotonique et
Pharmacologie, Faculte´ de Pharmacie, Universite´ de Strasbourg, Illkirch, France
Luciano Avio Institute of Agricultural Biology and Biotechnology, CNR, Pisa,
Italy
Vivek K. Bajpai Laboratory of Plant Molecular Physiology, School of Biotechnology, Yeungnam University, Gyeongsan, Gyeongbuk, Korea
Khalid BAK School of Medicine and Health Sciences, Monash University
Sunway Campus Jalan Lagoon Selatan, Selangor Darul Ehsan, Malaysia
Sanjeev Banerjee Department of Pathology, Barbara Ann Karmanos Cancer
Institute, Wayne State University School of Medicine, Detroit, MI, USA
Hannah E. Bartlett Ophthalmic Research Group, School of Life and Health
Sciences, Aston University, Birmingham, UK
Amrita Basu Department of Genetics, University of Calcutta, Kolkata, India
Sarai Belchı´-Navarro Department of Plant Biology, University of Murcia,
Murcia, Spain
Catherine Bennetau-Pelissero Physiopathologie de la plasticite´ neuronale, U862,
Universite´ de Bordeaux, Bordeaux, France
Strahil Berkov AgroBioInstitute, Sofia, Bulgaria
Linda S. Bert Universite´ de Bordeaux 1, INRA, UMR 1332 de Biologie du Fruit
et Pathologie, Villenave d’Ornon, France
Trust Beta Department of Food Science and Richardson Centre for Functional
Foods and Nutraceuticals, University of Manitoba, Winnipeg, Manitoba, Canada

Stefan Bieri Official Food and Veterinary Control Authority of Geneva, Geneva,
Switzerland
Rumen Binev Tracia University, Stara Zagora, Bulgaria
S. W. Annie Bligh Institute for Health Research and Policy, London Metropolitan
University, London, UK
Mercedes Bonfill Laboratori de Fisiologia Vegetal, Facultat de Farma`cia,
Universitat de Barcelona, Barcelona, Spain
Jean-Jacques Bosc INSERM U916, Institut Bergonie´, Universite´ Bordeaux
Segalen, Bordeaux, France


List of Contributors

xxiii

Giovanna Boschin Department of Pharmaceutical Sciences, Universita` degli
Studi di Milano, Milan, Italy
Genevie`ve Bourdy UMR 152 (Laboratoire Pharmadev), Institut de Recherche
pour le Developpement (IRD), Universite´ de Toulouse (UPS), Toulouse, France
Lisa Boureau Universite´ de Bordeaux 1, UMR 1332 de Biologie du Fruit et
Pathologie, Villenave d’Ornon, France
Pathik S. Brahmkshatriya Institute of Organic Chemistry and Biochemistry, v.v.
i. and Gilead Sciences and IOCB Research Center, Academy of Sciences of the
Czech Republic, Prague, Czech Republic
Priyanka P. Brahmkshatriya Department of Pharmacology, L. J. Institute of
Pharmacy, Ahmedabad, Gujarat, India
M. Br€
ohan Unite´ de Brasserie et des Industries Alimentaires, Earth and Life
Institute, Universite´ catholique de Louvain, Louvain-la-Neuve, Belgium
Nelson L. Brock Institut f€

ur Organische Chemie, Technische Universit€at Braunschweig, Braunschweig, Germany
Roque Bru Department of Agrochemistry and Biochemistry, University of
Alicante, Campus Universitario de San Vicente de Raspeig, Alicante, Spain
Gerhard Buchbauer Department of Clinical Pharmacy and Diagnostics, Center
of Pharmacy, University of Vienna, Vienna, Austria
Stefania Bulotta Department of Health Sciences, University “Magna Graecia” of
Catanzaro, Catanzaro, Italy
Conceic¸a˜o Calhau Department of Biochemistry (U38-FCT), University of Porto,
Porto, Portugal
D. Callemien Unite´ de Brasserie et des Industries Alimentaires, Earth and Life
Institute, Universite´ catholique de Louvain, Louvain-la-Neuve, Belgium
Emma Cantos-Villar Instituto de Investigacio´n y Formacio´n Agraria y Pesquera
(IFAPA), Rancho de la Merced, Junta de Andalucı´a, Jerez de la Frontera, Cadiz,
Spain
V. L. Cebolla Instituto de Carboquı´mica, Consejo Superior de Investigaciones
Cientı´ficas (CSIC), Zaragoza, Spain
Jaime Cebolla-Cornejo Instituto Universitario de Conservacio´n y Mejora de
la Agrodiversidad Valenciana (COMAV), Universitat Polite`cnica de Vale`ncia,
Vale`ncia, Spain
Dipjyoti Chakraborty Department of Bioscience and Biotechnology, Banasthali
Vidyapith, Banasthali, Rajasthan, India


xxiv

List of Contributors

Victoria L. Challinor School of Chemistry and Molecular Biosciences, The
University of Queensland, Brisbane, Australia
Sui Yung Chan Department of Pharmacy, National University of Singapore,

Singapore, Republic of Singapore
Chanchal Chandramouli School of Science, Monash University Sunway
Campus Jalan Lagoon Selatan, Selangor Darul Ehsan, Malaysia
Qinhua Chen Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, Institute of Pharmaceutical Analysis and Drug Screening, Wuhan University School of Pharmaceutical Sciences, Wuhan, China
Zilin Chen Key Laboratory of Combinatorial Biosynthesis and Drug Discovery,
Ministry of Education, Institute of Pharmaceutical Analysis and Drug Screening,
Wuhan University School of Pharmaceutical Sciences, Wuhan, China
Dapeng Chen Department of Pharmacology, Dalian Medical University, Dalian,
China
F. Chen Department of Plant Sciences, University of Tennessee, Knoxville,
TN, USA
Han Hui Cheong Department of Pharmacy, National University of Singapore,
Republic of Singapore
Alberto Chisvert Department of Analytical Chemistry, University of Valencia,
Burjassot, Valencia, Spain
Remigius Chizzola Institute of Animal Nutrition and Functional Plant Compunds,
University of Veterinary Medicine Vienna, Vienna, Austria
Ainura Chodoeva INSERM U916, Institut Bergonie´, Universite´ Bordeaux
Segalen, Bordeaux, France
M. Iqbal Choudhary H.E.J. Research Institute of Chemistry, International Center
for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
Department of Biochemistry, Faculty of Sciences, King Abdulaziz University,
Jeddah, Saudi Arabia
Philippe Christen School of Pharmaceutical Sciences, EPGL, University of
Geneva, University of Lausanne, Geneva, Switzerland
Søren Brøgger Christensen Department of Drug Design and Pharmacology, The
Faculty of Health Sciences, University of Copenhagen, Copenhagen, Denmark
Gehoon Chung National Research Laboratory for Pain, Dental Research Institute
and Department of Neurobiology and Physiology, School of Dentistry, Seoul
National University, Seoul, Korea