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PHYTOCHEMICALS
MECHANISMS OF ACTION
PHYTOCHEMICALS
MECHANISMS OF ACTION

Edited by
Mark S. Meskin
Wayne R. Bidlack
Audra J. Davies
Douglas S. Lewis
R. Keith Randolph

CRC PR E S S
Boca Raton London New York Washington, D.C.
CRC Press
Taylor & Francis Group
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Boca Raton, FL 33487-2742
© 2004 by Taylor & Francis Group, LLC
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Version Date: 20130919

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 Preface
The Fourth International Phytochemical Conference, “Phytochemicals: Mechanisms
of Action,” took place on the campus of California State Polytechnic University,
Pomona on October 21 through October 22, 2002. This conference was the fourth
in a series initiated in the mid-1990s to encourage a solid research-based approach
to the exploration and development of functional foods and nutraceuticals that might
play a role in health promotion, disease prevention, and therapeutic interventions.
Phytochemical research was not new at that time, but the food industry had expressed
renewed interest in the potential of phytochemicals and the phytochemical industry
entered a rapid growth phase internationally. The first conference, held in 1996,
reflected the organizers’ conviction that a consensus was emerging among many
researchers that plant-based food constituents might provide benefits beyond their
roles as essential nutrients. Biennial conferences have continued since 1996. Con-
ference participants were updated on the latest trends in phytochemical research,
participated in discussions of research methodologies, learned about the identifica-
tion and evaluation of potentially useful plant-based chemicals, and received in-
depth information on the most promising phytochemicals. In addition to educating
participants, the other goal of these conferences was to disseminate high quality
information through a series of books based on the conference proceedings. Three
widely respected books based on the first three international phytochemical confer-
ences have been published, including Phytochemicals: A New Paradigm (1998),
Phytochemicals as Bioactive Agents (2000), and Phytochemicals in Nutrition and
Health (2002).
Compelling epidemiological evidence associates diets rich in fruits, vegetables,
and whole grains with decreased risk of chronic degenerative diseases. Research
accumulated over the past five decades has begun to identify and characterize the
effects of certain plant-derived compounds in those fruits, vegetables, and whole
grains on a variety of physiological and pathological processes. Research in this
exciting area of health promotion is rapidly evolving. Phytochemical mechanisms
of action are beginning to emerge as the pharmacokinetics and metabolic functions
of these phytochemicals are characterized.
The organizers of the Fourth International Phytochemical Conference identified
three areas of research that had not received sufficient attention in the previous
conferences and books. The first area is bioavailability and pharmacokinetics. Bio-
availability of promising biochemicals and their metabolism, tissue distribution, and
excretion rates need to be established to devise optimum diets. All too often phy-
tochemicals are hyped with theoretical health claims without bioavailability and
pharmacokinetics information. Chapter 2 covering flavonoids and Chapter 3 covering
green tea catechins provide excellent examples of the types of discussion of bio-
availability and pharmacokinetics that need to take place in order to establish the
roles phytochemicals might play in human health and disease.
The second area of research identified as high priority is the need to determine
the mechanisms of action of key phytochemicals. Associations between phytochem-
icals and chronic disease have been suggested by epidemiological studies but the
mechanisms through which these phytochemicals work at the cellular level are only
beginning to emerge. In many cases it is also possible that the secondary metabolites
of the phytochemical of interest are responsible for observed biological activity. The
title of this book was chosen to emphasize the importance of researching and
establishing mechanisms of action for promising phytochemicals. Many of the
chapters in this book share research on and provide discussions of the mechanisms
of action of phytochemicals or phytochemical classes including Chapter 1 on antho-
cyanins, Chapter 4 on polyphenols, Chapter 5 on apigenin, Chapter 6 on phyto-
polyphenols, Chapter 7 on glucosinolates, Chapter 9 on resveratrol, and Chapter 10
on curcumin.
The third priority for the conference was to engage participants in a discussion
of clinical outcomes and methodology regarding phytochemicals. In order for the
field of phytochemistry to realize its true potential, clinical data are critically impor-
tant. Three questions that need to be answered are: (1) What data are available to
demonstrate the clinical efficacy and safety of phytochemicals? (2) What are rea-
sonable biomarkers for clinical outcomes? and (3) What innovative methods to
determine clinical outcomes are being developed? Chapter 11 presents a useful
animal model for efficacy studies with carotenoids and discusses the development
of a mixture of carotenoids as a cancer chemopreventive agent. Chapter 8 is an
excellent example of a thoughtful discussion comparing dietary intake modification
vs. the addition of a phytochemical to the diet to bring about primary prevention of
coronary artery disease.
In addition to these three priority areas of research, speakers addressed gene
regulation and expression in much greater depth than in previous conferences (Chap-
ter 4 through Chapter 7) and provided in-depth coverage of compounds not previ-
ously covered in significant detail such as quercetin (Chapter 2), resveratrol (Chapter
5 and Chapter 9) and curcumin (Chapter 11).
The chapters in this book include the materials shared at the Fourth International
Phytochemical Conference as well as additional expanded information. The speak-
ers/authors were all invited because of their expertise and international reputations.
Anthocyanins are water soluble plant compounds responsible for the blue, purple
and red color of many plant tissues. The absorption and metabolism of these widely
consumed compounds as well as their potential health benefits are discussed by Prior
in Chapter 1. In Chapter 2 Williamson gives a detailed overview of the absorption,
metabolism and excretion of flavonoids including quercetin. Green tea is one of the
most popular beverages worldwide and Chow and Cai review the animal and human
pharmacokinetic research done on green tea catechins in Chapter 3. All three of
these chapters emphasize the importance of understanding the pharmacokinetics of
these phytochemicals in humans. The authors also point out the weaknesses in the
current databases.
Barnes and colleagues demonstrate the value of understanding the metabolism
of phytochemicals as they present data on polyphenols. In Chapter 4 these authors
show that it can be the metabolites of the primary compounds rather than the primary
compounds themselves that have the critical biological actions. In Chapter 5, Birt
and coworkers show that studies of phytochemical modulation of cell cycle can
be helpful in optimizing cancer prevention strategies. Their studies look at the
modulation of the cell cycle by apigenin and resveratrol. In Chapter 6 Lin looks at
the modulation of signal transduction pathways by phytopolyphenols found in green
and black teas. Knowledge of modulation of these pathways can suggest strategies
for cancer chemoprevention.
In Chapter 7, Jeffery and colleagues cover what is known about the genetic
regulation of detoxification enzymes after consumption of broccoli, a cruciferous
vegetable. The authors point out that the upregulation of detoxification enzymes can
serve as a good biomarker of exposure to cruciferous vegetables. The evidence
suggests that broccoli consumption may slow or prevent cancer.
Chapter 8 from Lewis and Matvienko offers one of the strongest arguments to
date for use of nutraceuticals in patient care. The authors methodically present the
case that diet alone is rarely effective in reducing risk for cardiovascular disease
while drug therapy for primary prevention of coronary artery disease has been
controversial. The addition of phytosterols to food is highly effective at lowering
plasma cholesterol levels. Wu and coworkers revisit the French paradox in Chapter
9. These authors also point out the weak effectiveness of dietary changes on the
reduction of risk for cardiovascular disease. The authors believe that the apparent
cardioprotection provided by red wine might be mediated by resveratrol. They
hypothesize that resveratrol may confer cardioprotection by functioning as a pleio-
tropic cellular effector.
Khachik and colleagues update and expand the ongoing discussion of carotenoids
that has taken place over the four international conferences. In Chapter 10 they
report on bioavailability studies of a multicarotenoid mixture of seven prominent
dietary carotenoids that might be hypothesized as a more effective chemopreventive
agent than a single carotenoid. Utilizing the multicarotenoid mixture, the studies
reported here test the suitability of C57BL/6J mice as a model for efficacy studies
with carotenoids. In the final chapter of the book (Chapter 11), Reddy and Rao make
a strong case for the use of curcumin as a chemopreventive agent for colon cancer
in humans. The authors discuss mechanisms of colon cancer chemoprevention and
point out that curcumin’s safety and preclinical efficacy studies suggest that curcumin
should be scheduled for human clinical trails for chemopreventive efficacy.
The material covered in this book should be of interest to a wide audience
including food scientists and food technologists, nutrition researchers and nutrition-
ists, botanists, chemists, pharmacists, and other allied health professionals. Our goal
has been to update, challenge and expand the field of phytochemical research. Our
ultimate goal is to help facilitate research that will lead to the discovery and devel-
opment of phytochemicals that can be used for health promotion and disease pre-
vention. We believe that this volume continues to promote and encourage high quality
science and that the information presented here will be an important addition to the
scientific literature on phytochemicals, functional foods and nutraceuticals.

Mark S. Meskin
 Acknowledgments
The editors and authors thank the Nutrilite Health Institute, Access Business Group,
for its support of the 2002 Fourth International Phytochemical Conference, Phy-
tochemicals: Mechanisms of Action, held in partnership with the College of Agri-
culture at the California State Polytechnic University, Pomona, October 21 and 22,
2002. The research presented at that conference led to the publication of this volume.
The editors would like to thank Eleanor Riemer for all of her support and
constant encouragement of this project. We would also like to thank editorial staff
members at CRC Press for their patience and excellent work, especially Helena
Redshaw and Marsha Hecht.
 The Editors

Mark S. Meskin, Ph.D., R.D., is professor and director of the Didactic Program in
Dietetics in the Department of Human Nutrition and Food Science, College of
Agriculture, at California State Polytechnic University, Pomona. He has been at Cal
Poly Pomona since 1996.
Dr. Meskin received his Bachelor of Arts degree in psychology from the Uni-
versity of California, Los Angeles (1976), his Master of Science degree in food and
nutritional sciences from California State University Northridge (CSUN, 1983), and
his Ph.D. degree in pharmacology and nutrition from the University of Southern
California (USC), School of Medicine (1990). In addition, he was a postdoctoral
fellow in cancer research at the Kenneth Norris Jr. Cancer Hospital and Research
Institute, Los Angeles (1990–1992). He received his academic appointment at the
USC School of Medicine (1992) and served as assistant professor of cell and
neurobiology and director of the Nutrition Education Programs (1992–1996). While
at the USC, School of Medicine, he created, developed, directed, and taught in the
Master’s Degree Program in Nutrition Science. Dr. Meskin has also served as a
faculty member of the Department of Family Environmental Sciences at CSUN and
the Human Nutrition Program at the University of New Haven, Connecticut.
Dr. Meskin has been a registered dietitian since 1984 and is also a certified
nutrition specialist (1995).
Dr. Meskin has been involved with both the local and national Institute of Food
Technologists for more than 20 years. He is a past chair of the Southern California
IFT and remains involved in SCIFT. Dr. Meskin has been an active food science
communicator for the national IFT and has been a member of the IFT/National
Academy of Sciences Liaison Committee and the IFT Expert Panel on Food Safety
and Nutrition. He is also involved in several IFT divisions, including the Nutrition
Division and the Toxicology and Safety Evaluation Division.
Dr. Meskin served a 3-year term (2000-2002) as a science advisor to the Food,
Nutrition and Safety Committee of the North American branch of the International
Life Sciences Institute. He is a long-time Advisory Board member of the Marilyn
Magaram Center for Food Science, Nutrition and Dietetics at CSUN, where he helps
guide the educational mission of the center and plan symposia. Dr. Meskin has been
involved with the Southern California Food Industry Conference for many years as
an organizer, chair, moderator, and speaker. He has also been a member of the
Medical Advisory Board of the Celiac Disease Foundation.
Dr. Meskin is regularly invited to speak to a variety of groups and writes for
several newsletters. He has been a consultant for food companies, pharmaceutical
companies, HMOs, and legal firms. He is a member of many professional and
scientific societies, including the American Dietetic Association, the American
Society for Nutritional Sciences, the American College of Nutrition, the American
Council on Science and Health, the Institute of Food Technologists, and the National
Council for Reliable Health Information.
 He has several major areas of research interest, including: (1) hepatic drug
metabolism and the effects of nutritional factors on drug metabolism and clearance,
nutrient-drug interactions; (2) the role of bioactive nonnutrients (phytochemi-
cals/herbs/botanicals/nutritional supplements) in disease prevention and health pro-
motion; (3) fetal pharmacology and fetal nutrition/maternal nutrition/pediatric nutri-
tion; (4) nutrition education; and (5) the development of educational programs for
improving science literacy and combating health fraud.
Dr. Meskin is a member of numerous honor societies including Phi Beta Kappa,
Pi Gamma Mu, Phi Kappa Phi, Omicron Nu, Omicron Delta Kappa, Phi Upsilon
Omicron, Gamma Sigma Delta, and Sigma Xi. He was elected a Fellow of the
American College of Nutrition in 1993 and was Certified as a Charter Fellow of the
American Dietetic Association in 1995. He received the Teacher of the Year Award
in the College of Agriculture in 1999 and the Advisor of the Year Award in the
College of Agriculture in 2002.

Wayne R. Bidlack, Ph.D., is dean, College of Agriculture, at California State

Polytechnic University, Pomona, and is professor in both the Department of Animal
and Veterinary Science and the Department of Nutrition and Consumer Sciences.
Dr. Bidlack received his Bachelor of Science degree in dairy science and tech-
nology from The Pennsylvania State University (1966), his Master of Science degree
from Iowa State University, Ames (1968), and his Ph.D. degree in biochemistry from
the University of California, Davis (1972). In addition, he was a postdoctoral fellow
in pharmacology at the University of Southern California School of Medicine
(1972–1974). He received his academic appointment at USC (1974), served as
assistant dean of medical student affairs (1988–1991), as professor and as interim
chair of pharmacology and nutrition (1992). Dr. Bidlack has also served as chairman
and professor of food science and human nutrition, and as director of the Center for
Designing Foods to Improve Nutrition at Iowa State University (1992–1995).
Dr. Bidlack has been a professional member of the Institute of Food Technolo-
gists (IFT) for more than 24 years. He has served as a member of the Annual Program
Committee, as a member of both the Expert Panel on Nutrition and Food Safety and
the Scientific Lectureship Committee, and as a scientific lecturer. He served as
program chairman and chairman of the IFT Toxicology and Safety Evaluation (TaSE)
Division from 1989 to 1990 and has served as a member of the Executive Committee
for both the TaSE Division and the Nutrition Division. He has served as editor of
the TaSE newsletter. For the Southern California Section of IFT, Dr. Bidlack has
served as councilor, chairman of the Scholarship Committee, program chairman and
chairman of the section from 1988 to 1989. He has also served as regional commu-
nicator for IFT in Southern California. Dr. Bidlack was elected a fellow of IFT in
June 1998 and elected counselor representative to the executive committee from
2000 to 2003. He served as co-chair of the International Union of Food Science and
Technology, XII World Congress, 2003, held in Chicago.
Dr. Bidlack is past president of the Food Safety Specialty Section of the Society
of Toxicology and has served on the International Life Sciences Institute Committee
on Nutrition and Food Safety and as a scientific advisor for the Subcommittee on
Iron and Health and the Subcommittee on Apoptosis Related to Fumonisin Toxicity.
He has also served as a member of the board for the Certification Board for Nutrition
Specialists (CBNS) and actively contributed to the creation of the national certifi-
cation exam. In addition, he is serving on the editorial board and as book editor for
the Journal of the American College of Nutrition. He served as an editor of two
books on phytochemicals published by Technomics and two others published by
CRC Press.
In 1990, Dr. Bidlack received the Meritorious Service Award from the California
Dietetic Association and the Distinguished Achievement Award from the Southern
California section of IFT. He was awarded honorary membership in the Golden Key,
national honor society in 1995 and in Gamma Sigma Delta in 1998. He also received
the Bautzer Faculty University Advancement Award for Cal Poly Pomona in 1998.
In 2002, Dr. Bidlack was awarded the CSU WANG Family Excellence Award for
Administrators. The Cal Poly Pomona Chapter of Gamma Sigma Delta awarded Dr.
Bidlack the Outstanding Faculty-Administration Award for 2003.
His research interests are varied but integrate the general areas of nutrition,
biochemistry, pharmacology and toxicology. Specifically, research projects examin-
ing the hepatic mixed function oxidase enzymes, drug and toxicant metabolism and
conjugation; isolation and characterization of retinoic acid UDP-glucuronosyl trans-
ferase; nutrient-nutrient interactions between vitamins and minerals, and nutrient-
xenobiotic toxicities. He also maintains interest in development of value-added food
products, evaluation of biologically active food components (both plant and animal)
and use of commodities for nonfood industrial uses.
Dr. Bidlack has authored more than 50 scientific publications. For these efforts
he has been elected to several national scientific societies, including the American
Institute of Nutrition (American Society of Nutritional Science), the American Col-
lege of Nutrition (Certified Nutrition Specialist), the Institute of Food Technologists,
the American Society of Pharmacology and Experimental Therapeutics, and others.
Dr. Bidlack has served as a consultant to Nestle/Carnation, Hunt–Wesson, West-
cotek, Sunkist, Excelpro, Frito–Lay, Apple Institute, International Life Sciences
Institute, Avocado Board, California Egg Commission, among others.

Audra Davies, M.S., is manager of the Department of Nutrition Science and Ser-
vices with the Nutrilite Health Institute in Buena Park, California. Her responsibil-
ities include management of the clinical research, nutrition education, and stability
programs that support the development of new products and evaluation of ingredients
for the Nutrilite product line. Davies is recognized as a global spokesperson sup-
porting the Nutrilite brand and the importance of science-based products.
Prior to joining Nutrilite in 1998, Davies was the director of product development
for an ingredient supplier to the food and dietary supplement industries. She has a
strong interest in phytochemical research and has several publications focused on
natural plant chemistry and fortified and functional foods to her credit. Through
her activities with the Nutrilite Health Institute, Davies has partnered with
California State Polytechnic University, Pomona, to coordinate a conference series
dedicated to the study and understanding of phytochemicals. Her commitment to
furthering the field of phytochemistry is reflected in her role as an editor of Phy-
tochemicals in Nutrition and Health, published by CRC Press in 2002, and the
current Phytochemicals: Mechanisms of Action. She holds a Master of Science
degree in food chemistry and nutritional biochemistry (1992) in addition to a Bach-
elor of Science degree in nutritional science (1988), both from the University of
Manitoba, Winnipeg, Canada.
Davies is a professional member of Institute of Food Technologists (IFT), Cana-
dian Institute of Food Science and Technology (CIFST), American Association of
Cereal Chemists (AACC), American Nutraceutical Association (ANA), Association
of Clinical Research Professionals (ACRP) and American Medical Writers Associ-
ation (AMWA). She is an active member of the Council for Responsible Nutrition
(CRN), serving on the Omega 3 Working Group and the Regulatory and Commu-
nication committees, among others.

Douglas S. Lewis, Ph.D., received his Bachelor of Science degree from the Uni-
versity of Georgia, Magna Cum Laude (1973) and his Ph.D. in biochemistry from
Michigan State University (1978). Following graduation, he served as a postdoctoral
fellow from 1978 to 1979 and as an assistant instructor (1980) in physiology at the
University of Texas Health Science Center, San Antonio. His research career began
in earnest as a research scientist (1980-87) and associate research scientist (1987-
1992) in the Department of Physiology and Medicine, Southwest Foundation for
Biomedical Research in San Antonio, studying nonhuman primates as a model for
the etiology of human nutrition related diseases. In 1992, he entered the academic
arena. Dr. Lewis taught in the Department of Food Science and Human Nutrition
at Iowa State University and was housed in the Center for Designing Foods to
Improve Nutrition from 1992 to 2001. Since then Dr. Lewis has been professor and
chair of the Human Nutrition and Food Science Department at Cal Poly Pomona.
His research interest is focused on identifying methods to optimize nutrition to
prevent long-term chronic disease states which are responsible for shortened life-
spans and increased days of disability. One goal is to prove that nutritious foods
such as beef and eggs, often targeted for dietary restriction, can be slightly modified
to improve nutrition and to lower plasma cholesterol. Current studies are focused
on phytosterols in nutritious foods, high and low glycemic foods, and high beta-
glucan barley. Since 1987, his research has been funded by NIH, USDA, and food
companies, Con Agra and Friskies, among them.

Keith Randolph, Ph.D., is the group leader for clinical investigations at the Nutrilite
Health Institute. His responsibilities include guiding the design and conduct of
clinical testing and the sponsorship of nutrition-oriented symposia, programs, and
distinguished lectureships. Dr. Randolph came to the Nutrilite Health Institute in
January 2000, with 17 years of combined experience in biochemical research and
development as a lipid biochemist at the State College of New York, Stony Brook,
the Medical College of Pennsylvania in Philadelphia, and the Cleveland Clinic
Research Foundation in Ohio. He holds a Bachelor of Science degree in chemistry
and biology from Wayland College, Texas, and a Ph.D. in experimental pathology
from the Bowman Gray School of Medicine of Wake Forest University, North
Carolina. Dr. Randolph is a fellow of the American College of Nutrition and holds
memberships in the American Society for Nutritional Sciences, American
Chemical Society, American Society for Molecular Biology and Biochemistry, and
the American Organization of Analytical Chemists. Aside from scientific interests,
he is an accomplished watercolor artist and has exhibited his work in New York and
California. His artistic interest is in botanicals rendered in pigments he extracts from
the plants he paints.
 Contributors
Angela Au Tracy D’Alessandro
Department of Food Science and Department of Pharmacology and
Human Nutrition Toxicology
Iowa State University University of Alabama
Ames, Iowa Birmingham, Alabama

Stephen Barnes, Ph.D. Victor M. Darley-Usmar, Ph.D.

Department of Pharmacology and Department of Pathology
Toxicology University of Alabama
University of Alabama at Birmingham Birmingham, Alabama
Birmingham, Alabama
Fumio Enjo, M.D.
Diane F. Birt, Ph.D. Strang Cancer Research Laboratory
Department of Food Science and The Rockefeller University
Human Nutrition New York, New York
Iowa State University
Ames, Iowa Junqiao Guo
New York Medical College
Brenda J. Boersma, Ph.D. Department of Biochemistry and
Department of Pharmacology and Molecular Biology
Toxicology Valhalla, New York
University of Alabama at Birmingham
Birmingham, Alabama Tze-chen Hsieh
New York Medical College
Yan Cai, Ph.D. Department of Biochemistry and
Arizona Cancer Center Molecular Biology
The University of Arizona Valhalla, New York
Tucson, Arizona
Elizabeth H. Jeffery, Ph.D.
H-H. Sherry Chow, Ph.D. Department of Food Science and
Arizona Cancer Center Human Nutrition
The University of Arizona University of Illinois
Tucson, Arizona Urbana, Illinois

Chilly Chung Yu Jiang

Department of Food Science and Department of Food Science and
Human Nutrition Human Nutrition
Iowa State University Iowa State University
Ames Iowa Ames, Iowa
Frederick Khachik, Ph.D. Nancy Paiva, Ph.D.
Department of Chemistry and Department of Food Science and
Biochemistry Human Nutrition
University of Maryland Iowa State University
College Park, Maryland Ames, Iowa

Marion C. Kirk Rakesh P. Patel, Ph.D.

Comprehensive Cancer Center Department of Pharmacology and
University of Alabama Toxicology
Birmingham, Alabama University of Alabama
Birmingham, Alabama
Douglas S. Lewis, Ph.D.
Department of Human Nutrition and Ronald L. Prior, Ph.D.
Food Science USDA-ARS
California State Polytechnic University Arkansas Children’s Nutrition Center
Pomona, California Little Rock, Arkansas

Jen-Kun Lin, Ph.D. Chinthalapally V. Rao

Institute of Biochemistry Division of Nutritional
College of Medicine Carcinogenesis
National Taiwan University American Health Foundation
Taipei, Taiwan Valhalla, New York

Martin Lipkin, M.D.

Bandaru S. Reddy, DVM, Ph.D.
Strang Cancer Research Laboratory
Division of Nutritional
The Rockefeller University
Carcinogenesis
New York, New York
American Health Foundation
Valhalla, New York
Xiaohua Lu
Department of Biochemistry and
Molecular Biology Laura Schmitt
New York Medical College Department of Food Science and
Valhalla, New York Human Nutrition
Iowa State University
Oksana Matvienko, Ph.D. Ames, Iowa
Department of Food Science and
Human Nutrition Kristin E. Stewart
Iowa State University Division of Nutritional Sciences
Ames, Iowa University of Illinois
Urbana, Illinois
Chu Won Nho
Department of Hematology and Nitin Telang, Ph.D.
Oncology Strang Cencer Research Laboratory
University of Illinois The Rockefeller University
Urbana, Illinois New York, New York
Weiqun Wang, Ph.D. Joseph M. Wu, Ph.D.
Department of Food Science and New York Medical College
Human Nutrition Department of Biochemistry and
Iowa State University Molecular Biology
Ames, Iowa Valhalla, New York

Gary Williamson, Ph.D.

Metabolic and Genetic Regulation
Nestlé Research Center
Lausanne, Switzerland
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