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List of Contributors xi
Nayana Rajan
Synthite Industries Pvt. Ltd.
Synthite Valley
Kadayiruppu
Kerala
India
Mithun Rudrapal
Department of Pharmaceutical Sciences
School of Biotechnology and
Pharmaceutical Sciences, Vignan’s Foundation
for Science, Technology & Research
Guntur
India
Sachithra Sabu
Synthite Industries Pvt. Ltd.
Synthite Valley
Kadayiruppu
Kerala
India
Rakesh Sagar
Department of Pharmacy
Shri Govindram Seksariya Institute of
Technology & Science (SGSITS)
Indore
Madhya Pradesh
India
Abhishek K. Sah
Department of Pharmacy
Shri Govindram Seksariya Institute of
Technology & Science (SGSITS)
Indore
Madhya Pradesh
India
Linson Cheruveettil Sajan
Synthite Industries Pvt. Ltd.
Synthite Valley
Kadayiruppu
Kerala
India
Puneet K. Samaiya
Department of Pharmacy
Shri Govindram Seksariya Institute of
Technology & Science (SGSITS)
Indore
Madhya Pradesh
India
Malik A. Sanusi
Department of Biochemistry and Molecular
Biology
Obafemi Awolowo University
Ile-Ife
Osun State
Nigeria
Biswatrish Sarkar
Department of Pharmaceutical Sciences and
Technology
Birla Institute of Technology
Ranchi
Jharkhand
India
Smitha Sarojam
Synthite Industries Pvt. Ltd.
Synthite Valley
Kadayiruppu
Kerala
India
Yashika Shadija
School of Biotechnology and Bioinformatics
D Y Patil Deemed to be University
Navi Mumbai
Maharashtra
India
Kanchanlata Tungare
School of Biotechnology and Bioinformatics
D Y Patil Deemed to be University
Navi Mumbai
Maharashtra
India
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List of Contributors
xii
Sugumari Vallinayagam
Department of Biotechnology
Vel Tech Rangarajan Dr. Sagunthala R and D
Institute of Science and Technology
Chennai
Tamil Nadu
Zwanden S. Yahaya
Department of Pharmaceutics and Industrial
Pharmacy
Faculty of Pharmaceutical Sciences
Kaduna State University,
Kaduna
Nigeria
Aamena Yusuf
School of Biotechnology and Bioinformatics
D Y Patil Deemed to be University
Navi Mumbai
Maharashtra
India
Kamaruz Zaman
Department of Pharmaceutical Sciences
Faculty of Science and Engineering
Dibrugarh University
Dibrugarh
Assam
India
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xiii
Preface
The book titled “Polyphenols: Food, Nutraceutical, and Nanotherapeutic Applications”
provides us with detailed information on the potential health benefits of food polyphenols against
human diseases and their therapeutic interventions as nutraceuticals and nanoformulations.
Plant-based foods, including nutraceuticals, functional foods, and dietary supplements, have grad-
ually become an area of increasing interest because of the potential health implications of polyphe-
nol-based food products available in the global market. Long-term consumption of foods rich in
polyphenols has been reported to improve conditions in diabetes, osteoporosis, cancer, neurologi-
cal disorders, and cardiovascular diseases. The market demand for polyphenol-based food prod-
ucts and nutraceutical preparations is increasing rapidly with social and economic developments
and the improvement in people’s health awareness. The beneficial effects of polyphenol-based
nutraceuticals and their nanoformulations attract more consumers. However, many polyphenols
have low oral bioavailability, which limits the application of polyphenols as nutraceuticals and in
the form of nanomedicine. This book would be a useful resource for researchers working in the
areas of dietary polyphenols, nanodelivery, and nutraceutical applications. The book chapters pro-
vide up-to-date information relating to the ongoing research on food polyphenols along with their
health and therapeutic implications as antioxidants. The chapters are described in a lucid and
consistent manner in order to aid flow, continuity, and technical presentation. In this book, the
health benefits of plant polyphenols in the prevention of various major diseases, such as cancer,
neurological disorders, central nervous system disorders, cardiovascular diseases, bacterial infec-
tions, and inflammatory disorders, are summarized. This book particularly delineates food poly-
phenols and their antioxidant potentials with special emphasis on their nutraceutical applications
and nanodeliveries. The bioavailability and pharmacokinetic issues and toxicity are also demon-
strated. This book will be useful to drug discovery scientists (R&D), pharmaceutical scientists,
biomedical scientists, food scientists, healthcare professionals, phytochemists, biochemists, clini-
cians, pharmacologists, dietician, nutritionists, research students, professors, and other research-
ers working in the field of polyphenols, nutraceuticals, and nanomedicine research.
Mithun Rudrapal
June, 2023
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1
Polyphenols: Food, Nutraceutical, and Nanotherapeutic Applications, First Edition. Edited by Mithun Rudrapal.
© 2024 John Wiley & Sons, Inc. Published 2024 by John Wiley & Sons, Inc.
1
Food Polyphenols
Antioxidant Properties and Health Benefits
Pruthvi G.R.
1
, Apoorva M.R.
1
, Anuthilakesh T.
1
, Bhargavi K.
1
, Nithish G.S.
2
, and Raghu
Ram Achar
1,
*
1
Division of Biochemistry, School of Life Sciences, JSS Academy of Higher Education and Research, Mysuru, Karnataka, India
2
Indian Institute of Science Education and Research Tirupati, C/o Sree Rama Engineering College (Transit Campus), Tirupati,
Andhra Pradesh, India
* Corresponding author
1.1 Introduction
1.1.1 Dietary Polyphenols
Polyphenols are a diverse group of naturally occurring compounds that are widely distributed in
plant-based foods such as fruits, vegetables, nuts, grains, and spices. They are characterized by
their multiple phenolic ring structures and they play a significant role in the color, flavor, and
nutritional properties of foods. Over the past few decades, research has shown that polyphenols
have various health-promoting benefits, including antioxidant, anti-inflammatory, anticancer,
and cardioprotective effects. As a result, there has been growing interest in the role of polyphenols
in human health, and they are now recognized as essential bioactive compounds in a diet. This
introduction provides a glimpse into the fascinating world of food polyphenols and their potential
health benefits.
Academic literature has documented approximately 50,000 distinct types of polyphenols, which
are secondary metabolites of plants produced via the shikimate-derived phenyl propanoic and/or
the polyketide pathways, in plants [1].
However, polyphenols can be broadly classified into four major groups: phenolic acids, flavo-
noids, phenolic amides, and other polyphenols [2].
Flavonoids
Flavonoids are a significant class of low molecular weight polyphenolic substances found widely
in the plant kingdom. Their presence is found in almost all parts of plants. These compounds have
a structural makeup of two aromatic rings with fifteen carbon atoms [3]. A three-carbon atom
chain connects the aromatic rings depending on the C ring that the B ring is linked to, its confor-
mation, and the degree of oxidation [4]. Flavonoids can be classified into different subclasses such
as chalcones, flavones, flavonols, and isoflavones [5]. Flavonoids provide the characteristic color,
flavor, and aroma of fruits and flowers, helping to attract pollinators [6].
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1 Food Polyphenols
2
Flavonoids possess a variety of biological properties favoring human health and agriculture
including anti-allergic, anti-inflammatory, antimicrobial, antioxidative, anticarcinogenic, and
antiviral properties [5].
Phenolic Acids
Phenolic acids are aromatic rings with one carboxylic group comprising phenolic acids (–COOH).
Although they are similar to alcohols, they become weak acids because of the presence of an
aromatic
ring and the hydrogen atom of the phenolic hydroxyl group [7]. They form a major group of polyphe-
nols produced by plants and play a vital role as a human dietary component. Phenolic acids have a high
antioxidant activity. Thus, a diet rich in phenolic acids helps the body cope with oxidative stress that
occurs, thereby reducing the risk of diseases related to oxidative stress. Structurally, phenolics are pre-
sent as bound forms such as amides, esters, or glycosides [8]. Phenolics are classified as hydroxybenzoic
acid and hydroxycinnamic acid. Hydroxycinnamic acids are chlorogenic, combining both caffeic and
quinic acids, whereas hydroxybenzoic acids contain a soluble C6–C1 structure that is derived from
benzoic acids [9]. Like flavonoids, phenolic compounds also possess biological properties.
Polyphenol Amides
Some polyphenols have N-containing functional substituents. These are classified as polyphenolic
amides. Capsaicinoids in chili and avenanthramides in oats are some of the major components of
common foods [10].
Other Polyphenols
The polyphenols that do not fall into the above classes are grouped under “other” and are desig-
nated as non-flavonoid polyphenols. This category includes stilbenes, lignans, and other polyphe-
nols, as shown in Figure 1.1 [10]. The classes and subclasses are listed in Table 1.1.
1.1.2 FDA-approved Antioxidant Polyphenols
FDA-approved antioxidant polyphenols are epigallocatechin, epigallocatechin-3-gallate (EGCG),
hydroxytyrosol, catechin, apigenin, anthocyanins, hydroxy-cinnamic acids, proanthocyanidin b4,
curcumin, kaempferol-3-ogalactoside, quercetin, kaempferol morin, apigenin, daidzein, ellagic
acid, gallic acid, corilagin, dihydrocaffeic acid, caffeic acid (+)-catechin, and resveratrol [11].
Figure 1.1 Classification of dietary polyphenols.
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1.1 Introduction 3
1.1.3 Polyphenols and Their Antioxidant Properties
Polyphenols are a group of organic compounds that occur naturally and are identified by the pres-
ence of multiple phenol units and their associated functional groups. The term “polyphenol” is
derived from the Greek words “polus”, which means “many” and “phenol”. Phenol refers to the
chemical structure comprising an aromatic benzene ring with a hydroxyl (–OH) group, similar to
that found in alcohols (therefore ending with the suffix -ol) [12].
The term “polyphenol” has been in existence since 1894. Although there is no clear definition of
polyphenols, it is widely accepted that they are natural compounds with a polyphenolic structure,
characterized by the presence of multiple hydroxyl (–OH) groups or other functional rings.
Polyphenols can be classified into four main classes: phenolic acids, flavonoids, stilbenes, and lig-
nans [13].
Condensed tannins, the most common type of polyphenols, can be found in nearly all plant
families. Larger polyphenols play a vital role in forest ecology by aiding in the decomposition of
forest litter and nutrient cycles, and they are often concentrated in leaf tissue, epidermis, bark lay-
ers, flowers, and fruits. The total amount of natural phenols and polyphenols, expressed as a per-
centage of the dry green leaf mass, varies between 1%–25%. The absolute quantity of total phenols
in plant tissues varies significantly depending on the assay used and the type of polyphenol, as well
as the literature source.
1.1.4 Polyphenols in Functional Foods and Nutraceuticals
Functional foods are food products that provide health benefits beyond basic nutrition, often
referred to as “rainbow color foods”. These foods can be categorized into modified or fortified func-
tional foods, and can be easily incorporated into a balanced diet. They can help bridge any gaps in
your diet, preventing nutrient deficiencies while also improving your overall health by increasing
your intake of essential nutrients such as vitamins, minerals, fiber, heart-healthy fats, and
probiotics.
Table 1.1 Classes and subclasses of dietary polyphenols.
Classes Subclasses Examples
Flavonoids ● Flavones
● Flavonols
● Isoflavones
● Flavanones
● Anthocyanins
● Luteolin, apigenin
● Quercetin, catechin
● Genistein, daidzein
● Hesperetin, naringenin
● Malvidin, cyanidin
Phenolic amides
● Avenanthramides
● Capsaicinoids
● Avenanthramide a: R = H; avenanthramide b:
R = OCH
3
; avenanthramide c: R = OH
● Capsaicin, dihydrocapsaicin
Phenolic acids
● Hydroxybenzoic acid
● Hydroxycinnamic acids
● Salicylic acid, gallic acid, vanillic acid, benzoic
acid, ellagic acid
● Caffeic acid, ferulic acid, cinnamic acid, cou-
maric acid, sinapinic acid
Other polyphenols
● Stilbenes
● Lignans
● Others including
tannins, lignins, xanthones,
chromones, anthraquinones
● Resveratrol, piceatannol
● Sesamol, pinoresinol, enterodiol
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1 Food Polyphenols
4
Conventional functional foods include a variety of fruits, such as berries, kiwi, pears, peaches,
apples, oranges, bananas, and pomegranates, as well as vegetables such as broccoli, cauliflower, kale,
zucchini, and spinach. Nuts, seeds, legumes, whole grains, seafood, fermented foods, herbs,
and
spices are also included in this category. Alternatively, modified functional foods include fortified
juices, dairy products, milk alternatives, grains, cereals, granola, eggs, and poultry. Supplements of
vitamins, minerals, botanicals, herbs, botanical compounds, amino acids, and probiotics are also
considered modified functional foods. By including these functional foods in our diets, we can fill in
any nutritional gaps and prevent deficiencies while enhancing our overall health.
1.2 Classification, Sources, and Functions
1.2.1 Hydroxybenzoic Acids, Hydroxycinnamic Acids, and Stilbenes
Polyphenols Structure Functions Sources References
Hydroxybenszoic
acid
H
H
O
O
O
These compounds
have demonstrated
potential in reducing
oxidative stress and
inflammation,
promoting better lipid
profiles, and exhibiting
anti-atherosclerotic,
anti-inflammatory,
analgesic, antibacterial,
hepatoprotective,
antiviral, and
antineoplastic effects
in both in vivo and in
vitro studies.
It is suggested that the
compound may play a
role in reversing
biochemical changes
related to cardiac
dysfunction, diabetes,
and metabolic
disorders because of its
antioxidant, anti-
inflammatory, and
antineoplastic
properties.
The therapeutic
potential of the
compound has been
noted in various
disorders including
gastrointestinal,
neuropsychological,
metabolic, and
cardiovascular
systems.
Blackberries,
cranberries,
grapefruit,
grapes,
mangos,
pomegranate,
raspberries,
rhubarb,
strawberries,
juices made
from these
fruits, tea,
red and white
wines,
chestnuts,
peanuts,
pecans,
walnuts,
wheat, select
herbs and
spices
[14–17]
Protocatechuic
acid
H
H
H
O
O
O
O
Gallic acid
H
H
H
H
O
OO
O
O
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1.2 Classification, Sources, and Functions 5
Polyphenols Structure Functions Sources References
Hydroxycinnamic
acids
H
H
H
H
O
O
O
These compounds
possess antioxidant,
anti-inflammatory,
anticollagenase,
antityrosinase
activities, UV
protective, and
anticarcinogenic
properties that make it
a promising agent for
antiaging and
anti-inflammatory
purposes, as well as for
use as a preservative
and hyperpigmentation
correcting ingredient.
Additional benefits
include antibacterial,
antiviral, anti-
atherosclerotic,
immunostimulatory,
antidiabetic,
cardioprotective,
antiproliferative,
hepatoprotective,
anticancer, and
anti-hepatocellular
carcinoma activity.
Blueberry,
kiwi, cherry,
plum,
aubergine,
apple, pear,
chicory,
artichoke,
potato, corn
flour, wheat
flour, rice
flour, oat,
cider, coffee,
wine, papaya,
onion,
strawberry,
raspberry,
sugarcane,
grape, cherry,
orange,
grapefruit,
watermelon,
blackberries,
peach,
banana
[18, 19]
Caffeic acid
Chlorogenic acid
O-Coumaric acid
H
H
H
H
O
O
O
Ferulic acid
H
H
H
H
O
O
O
O
(Continued)
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1 Food Polyphenols
6
1.2.2 Flavonoids, Flavonols, Flavones, Isoflavones, Flavanones, and Flavanols
Flavonols
H
O
O
O
Flavonoids reduce the
risk of cardiovascular
diseases, metabolic
disorders, and certain
types of cancer by
reducing oxidative
stress, inhibiting
low-density lipoprotein
oxidation and platelet
aggregation, and acting
as vasodilators in blood
vessels.
● Kaempferol inhibits
cancer cell growth
and angiogenesis,
induces cancer cell
apoptosis, and pre-
serves normal cell
viability, exerting a
protective effect.
● Myricetin has
neuroprotective ac-
tion, antidiabetic,
anticancer, im-
munomodulatory,
cardiovascular,
analgesic, and anti-
hypertensive prop-
erties, which have
been demonstrated
in preclinical stud-
ies on Alzheimer’s,
Parkinson’s and
Huntington’s dis-
eases, as well as
amyotrophic lateral
sclerosis.
Apples,
asparagus,
broccoli, chili
pepper,
Chinese
cabbage, kale,
leeks, lettuce,
onions,
spinach,
chives, dill,
fennel leaves,
oregano,
blueberry,
cherry,
cranberry,
wild leeks
(whole),
black tea, red
wine,
cranberry,
dock
sweet potato
leaves,
chard, swiss,
broad beans,
immature
seeds,
rutabagas,
garlic
blueberry,
peppers, hot
chili, green,
blackberry,
lotus root,
lemon
[20–24]
Quercetin
H
H
H
H
H
O
O
O
O
O
O
O
Kaempferol
H
H
H
H
O
O
O
O
O
O
Myricetin
H
H
H
H
H
H
O
O
O
OO
O
O
O
Flavones
O
O
● Offers protection
against various
cancer types,
including breast,
uterine, colon, lung,
ovarian-prostate,
skin, liver, and
stomach cancer.
● Demonstrates
neuroprotective
properties.
Parsley,
chamomile,
celery, vine-
spinach,
artichokes,
oregano, celery,
parsley,
broccoli, onion
leaves, carrots,
peppers,
cabbages, apple
skins,
chrysanthemum
flowers
[25, 26]
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1.2 Classification, Sources, and Functions 7
Apigenin
H
H
H
O
O
O
O
O
Luteolin
H
H
H
H
O
O
O
O
O
O
Flavanones
O
O
Hesperidin has shown
benefits for
cardiovascular
function, type II
diabetes, and
cutaneous functions.
● For skin, hes-
peridin has been
found to have
wound healing,
UV protection,
anti-inflammatory,
antimicrobial,
anti-skin cancer,
and skin lightening
properties.
● Hesperidin pro-
motes carbohy-
drate metabolism,
increases antiox-
idant defenses,
modulates immune
system activity,
and has anti-
atherogenic and
anti-inflammatory
effects by decreasing
lipid peroxidation
biomarkers and pro-
tein carbonylation.
Orange juice,
grapefruit juice,
lemon juice
[27–29]
Hesperetin
H
H
H
O
O
O
O
O
O
(Continued)
(Continued)
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