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16 Flavonoids as Nutraceuticals
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Flavonoids as Nutraceuticals. Rajesh K. Kesharwani, Deepika Saini, Raj K. Keservani, and
Anil Kumar Sharma (Eds.)
© 2024 Apple Academic Press, Inc. Co-published with CRC Press (Taylor & Francis)
CHAPTER 2
INTRODUCTION TO FLAVONOIDS
DEEPANSHU RANA,
1
NANCY GAUTAM,
2
KESHARI NANDAN,
3
and
ANKIT SINGH
4
1
Assistant Professor, Department of Microbiology, Sardar Bhagwan
Singh University, Balawala, Dehradun, Uttarakhand, India
2
Research Scholar, Department of Chemistry, Meerut College,
Meerut, Uttar Pradesh, India
3
Department of Chemistry, Gurukula Kangri (Deemed to be University),
Haridwar, Uttarakhand, India
4
Research Scholar, Department of Chemical Engineering, Rajiv Gandhi
Institute of Petroleum Technology, Jais, Amethi, Uttar Pradesh, India
ABSTRACT
Humans have been consuming plants and herbs for ages which are rich in
phytonutrient compounds synthesized within these plants and herbs. Flavo
-
noids are ubiquitous in the plant kingdom, having a characteristic flavan
nuclei, giving rise to various functions, including UV protection, defense,
auxin transport inhibition, allelopathy, and flower coloring. They are also
responsible for various biological activities in plant, animal, and bacterial
systems, and many groups have isolated and identified the structures of
flavonoids possessing antifungal, antiviral, and antibacterial activity. Apart
from this, the synergistic effects of flavonoids with existing chemothera-
peutics are also evaluated. Hence, these compounds are becoming vital for
nutraceutical, pharmaceutical, medicinal, cosmetic, and other applications.
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20 Flavonoids as Nutraceuticals
2.1 INTRODUCTION
Polyphenols are a group of chemical compounds produced during the
secondary metabolism in specific plant organs like roots, stems, leaves,
and fruits. These compounds serve as a large pool of bioactive chemicals
displaying a variety of biological functions. Out of this large group, flavo-
noids are the major compounds having wide distribution in higher as well as
lower plants (
Karak, 2019).
Flavonoids generally have a low molecular weight (Fernandez et al., 2006;
Heim et al., 2002; Karak, 2019) with an omnipresence in the photosynthesizing
cells as glycosides or methylated derivatives (Karak, 2019). Although they are
non-essential for the survival of plants still, they occur widely in the plant
kingdoms (
Buer et al., 2010; Cushnie & Lamb, 2005; Havsteen, 1983). These
compounds are also present in fruit, vegetables, nuts, tea, wine, propolis, and
honey making it an inevitable of human diet (Cushnie & Lamb, 2005; Grange
& Davey, 1990; Harborne & Baxter, 1999; Middleton & Chithan, 1993).
The avonoid research was pioneered by Albert Szent-Gyorgi in the year
1936 while he was working on lemon peels to establish the synergy between
pure vitamin C and unidentied cofactors, which he named citrin and later
vitamin P (Karak, 2019; Murray, 1998).
2.2 CHEMISTRY OF FLAVONOIDS
Flavonoids are the phytochemicals belonging to the class polyphenols which
have been used in Chinese and ayurvedic medicines since ages. As per
the Global health center, flavonoids not only exhibit antioxidant and anti-
inflammatory activity but also demonstrate skin protection, brain function,
blood sugar, and blood pressure regulation. In the year 1930, a substance
originating from oranges was designated as vitamin P but later on recognized
as flavonoid (rutin), and till now, more than 4,000 varieties have been identi
-
fied (Karak, 2019; Middleton, 1998).
In plants, avonoids can be present as glycosides, aglycones, or some-
times as methylated derivatives having structural diversity. The basic
framework in the chemical structures of these compounds is of diphenyl
propane comprising 15 carbon atoms in the primary nucleus having two
six-membered rings linked with a three-carbon unit which may or may not
be a part of a third ring (Middleton, 1984). This heterocyclic ring contains a
pyrene ring having oxygen, which is linked with two benzene rings (ring A
and ring B), referring to this as C6-C3-C6 labeled A, B, and C (Figure 2.1)
(Karak, 2019; Pietta, 2000; Rice-Evans et al., 1976).
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21 Introduction to Flavonoids
FIGURE 2.1 Basic framework of flavonoids.
As far as the naming of these magical compounds is concerned, it can be
assigned in three ways (Cushnie & Lamb, 2005; Harborne & Baxter, 1999):
1. Trivial Names: They are broadly in use and may indicate class
or plant source. For example, compounds belonging to the class
anthocyanidin names ending with 'inidin,' and 'etin' belong to the
class flavonol, whereas genera Triticum and Hypolaena contain
compounds tricin and hypolaetin, respectively.
2. Semi-Synthetic Names: This naming scheming is based on
trivial names depending on the parent structure. For example,
flavone or chalcone, e.g., 3,5,7,3,4-pentahydroxy flavone or
3,3,4,5,7-pentahydroxyflavone.
3. Synthetic Names: This method is very rare and burdensome. For
example, 3,4-dihydro-2-phenyl-2H-1-benzopyran for flavan.
Spectroscopic studies of avonoids revealed that in most avones and
avonols, absorption maxima of B ring lie in between the range of 320–385
nm while a maximum range of 250–285 nm is associated with ring A.
Different functional groups might get attached to avonoid, causing a shift in
absorption peaks viz. kaempferol (367 nm), quercetin (371 nm), and myric-
etin (374 nm) (Kumar & Pandey, 2013; Yao et al., 2004). The one thing which
distinguishes avones from avonols is the lack of 3-hydroxyl group. UV
spectra of avonones revealed the presence of a saturated heterocyclic C ring
having no association between the A and B rings (Rice-Evans et al., 1996).
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22 Flavonoids as Nutraceuticals
They exhibit maximum absorption at 270 nm because it has monosubstituted
B ring but when di-, tri-, or o-substituted B ring are there, two peaks or one
peak (258 nm) with a shoulder (272 nm) is present however anthocyanins
has two distinctive bands 450–560 nm (hydroxyl cinnamoyl system-B ring)
and 240–280 nm (benzoyl system-A ring) although, coloration of anthocya
-
nins changes with the change in position of hydroxyl groups (Wollenweber
& Dietz, 1981).
2.3 CLASSIFICATION OF FLAVONOIDS
Characterization of flavonoids is based on how the aromatic B ring is attached
to the carbon of the benzopyran C ring, its degree of unsaturation as well as
oxidation of the C ring (Panche et al., 2016). Flavonoids (2-phenylbenzo-
pyrans), isoflavonoids (3-benzopyrans), and neoflavonoids (4-benzopyrans)
are the three major classes of flavonoids depending upon the linkage of the
aromatic ring to the benzopyrano (chromano) moiety. Flavonoids may be
further sub-divided into the following groups based on the oxidation and
saturation in the heterocyclic ring: flavan, flavanone, dihydro flavonol,
flavonol, flavone, flavone-3-ol, and flavone-3,4-diol. Isoflavonoids and
neoflavonoids are further classified into different groups and there are some
minor flavonoids are also present in plants (
Table 2.1) (Samanta et al., 2011;
Stobiecki & Kachlicki, 2008). Table 2.2 comprises the data of different
classes and subclasses of flavonoids with respect to their origin in natural
sources and chemical structure (Panche et al., 2016).
TABLE 2.1 Sub-Division of Flavonoids
Isoflavonoids Neoflavonoids Minor Flavonoids
Isoflavan 4-arylcoumaril 2´-OH-chalcone
Isoflavone 3,4-dihydro-4-arylcoumarin 2´-OH-dihydrochalcone
Isoflavanone Neoflavene 2´-OH-retro-chalcone
Isoflavan-3-ene – Aurone
Isoflavanol – Auronols
Rotenoid – –
Coumestane – –
3-arylcoumarin – –
Coumaronochromene – –
Coumaronochromone – –
Pterocarpan – –
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23
TABLE 2.2 Flavonoid Classes, Structures, Subclasses, and Natural Sources
Classes
Structure Subclasses Sources Parts References
Flavones Luteolin, apigenin,
tangeritin, tageretin,
nobiletin, and
sinensetin
Flavonols Kaempferol, quer-
cetin, myricetin, rutin,
morin
Flavanones Hesperitin, naringenin,
and eriodictyol,
naringin, eriodictyol,
hesperidin
Genistin, genistein,
daidzein, glycitein,
daidzin
Isoflavonoids
Celery, parsley, red
peppers, chamomile,
mint, ginkgo biloba,
citrus fruits
Onions, kale, lettuce,
tomatoes, apples,
grapes, and berries, tea,
and red wine
Oranges, lemons, and
grapes
Leguminous plant like
soyabean, microbes
Leaves, flowers,
fruits, and fruit
peel
Fruits, vegetables
Peel
Whole plant
Manach et al. (2004)
Iwashina (2013)
Iwashina (2013)
Matthies et al.
(2008); Panche et al.
(2016)
Introduction to Flavonoids
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24
TABLE 2.2 (Continued)
Classes
Structure Subclasses Sources Parts References
Neoflavonoids
Anthocyanins
Chalcones
4-arylcoumarins
(neoflavones),
4-arylchromanes,
dalbergiones, and
Dalbergia quinols
Cyanidin, malvidin,
delphinidin, malvidin,
pelargonidin, and
peonidin
Phloretin, phloridzin,
arbutin, and
chalconaringenin
Calophyllum
inophyllum, Mesua
thwaitesii
Cranberries, black
currants, red grapes,
merlot grapes, raspber-
ries, strawberries,
blueberries, bilberries,
and blackberries
Tomatoes, pears,
strawberries, bearber
-
ries, and certain wheat
products
Seeds, bark, and
timber
Plants, flowers,
and fruits
–
Linuma et al.
(1987); Nishimuta et
al. (2000); Garazd et
al. (2003)
Iwashina (2013)
Panache et al. (2016)
Flavonoids as Nutraceuticals
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Introduction to Flavonoids 25
2.4 SIGNIFICANCE OF FLAVONOIDS IN PLANTS
2.4.1 SIGNALING MOLECULES
These chemical compounds are synthesized by the root and shoot tissues of
the plants, acting as an important signal molecule that plays a significant role
in plant-microbe interaction (
Dixon & Steele, 1999; Peer & Murphy, 2006)
and the formation of root nodule also, which ultimately leads to nitrogen
fixation (Fox et al., 2001; Sundaravarathan & Kannaiyan, 2002). Roots of
legumes secret certain chemicals which not only attract the symbionts but
also catch the attention of the pathogens. These chemicals will begin the
nodulation process begin initiated by host-specific signal molecules, while
flavonoid induction of specific pathogenicity genes and stimulation of devel
-
opment required for pathogenesis will lead to the development of infections
in plants (Straney et al., 2002;
Subramanian et al., 2007). Nodulation is
governed by the nod gene, and flavonoids act as inducers of this particular
gene accumulation of this gene will trigger flavonoid production in the root,
which again induces the nod gene (Steinkellner et al., 2007; Tsai & Phillips,
1991). Flavonoids also act as eco-sensing molecules, which accomplishes
symbiotic mutualisms (Ndakidemi & Dakora, 2003).
2.4.2 PHYTOALEXINS
Plants always encounter several pathogens, and as a defense mechanism,
they produce some chemicals known as phytoalexins mainly contain pheno
-
lics, stilbenoids, alkaloids, terpenoids, coumarins, and polyacetylenes (Fawe
et al., 1998; Iwashina, 2003; McNally et al., 2003). However, in legumes,
isoflavonoids are involved in defense response in which migration of phenyl
ring is obtained. One such compound is vesitol belonging to the class of
isoflavones synthesized in some species of lotus (Lanot & Morris, 2005).
Although aglycone rhamnetin is a flavonoid which was first reported, phyto
-
alexin isolated from cucumber was previously believed to be nonexistent
in this family (Fawe et al., 1998). Stilbene is a phytoalexin produced in the
family VItaceae and was found to be active against several phytopathogens
(Jeandet et al., 2002) because these compounds have low molecular weight
and exhibit antimicrobial activities, thus becoming a vital factor against plant
pathogens (Bajaj, 1996). Although still, there is still a scarcity availability
of data related to the role of these compounds in the interaction between
rhizobia and their legume host (Parkniske et al., 1991).
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