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Flavonoids
Dr. Louay Labban
A’Sharqiyah University
Flavonoids
• Polyphenolic compounds that are ubiquitous
in nature and are categorized, according to
chemical structure, into flavonols, flavones,
flavanones, isoflavones, catechins,
anthocyanidins and chalcones
What are flavonols?
• Flavonols are phytochemical compounds
found in high concentrations in a variety of
plant-based foods and beverages. Based on
their structure, flavonols are classified as
flavonoids and include the following
compounds: quercitin, kaempferol, and
myricetin.
• Over 4,000 flavonoids have been identified,
many of which occur in fruits, vegetables and
beverages (tea, coffee, beer, wine and fruit
drinks).
• The flavonoids have aroused considerable
interest recently because of their potential
beneficial effects on human health they have
been reported to have antiviral, antiallergic,
antiplatelet, antiinflammatory, antitumor and
antioxidant activities.
• Antioxidants are compounds that protect cells
against the damaging effects of reactive
oxygen species, such as singlet oxygen,
superoxide, peroxyl radicals, hydroxyl radicals
and peroxynitrite.
• An imbalance between antioxidants and
reactive oxygen species results in oxidative
stress, leading to cellular damage. Oxidative
stress has been linked to cancer, aging,
atherosclerosis, ischemic injury, inflammation
and neurodegenerative diseases (Parkinson's
and Alzheimer's).
• Flavonoids may help provide protection
against these diseases by contributing, along
with antioxidant vitamins and enzymes, to the
total antioxidant defense system of the human
body.
• Epidemiological studies have shown that
flavonoid intake is inversely related to
mortality from coronary heart disease and to
the incidence of heart attacks.
• The recognized dietary antioxidants are
vitamin C, vitamin E, selenium, and
carotenoids. However, recent studies have
demonstrated that flavonoids found in fruits
and vegetables may also act as antioxidants.
• Like alphatocopherol (vitamin E), flavonoids
contain chemical structural elements that may
be responsible for their antioxidant activities.
The contribution of flavonoids to the
antioxidant defense system may be substantial
considering that the total daily intake of
flavonoids can range from 50 to 800 mg.
Dosage
• Flavonoid intake depends upon the
consumption of fruits, vegetables, and certain
beverages, such as red wine, tea, and beer.
The high consumption of tea and wine may be
most influential on total flavonoid intake in
certain groups of people.
• This intake is high compared to the average
daily intake of other dietary antioxidants like:
• vitamin C (70 mg)
• vitamin E (710 mg)
• or carotenoids (23 mg).
Antioxidant flavonoids
• Quercetin (a flavonol in vegetables, fruit skins,
onions)
• Xanthohumol (a prenylated chalcone in hops
and beer)
• Isoxanthohumol (a prenylated flavanone in
hops and beer)
Hops ‫أو‬ ‫الدينار‬ ‫حشيشة‬
• Genistein (an isoflavone in soy) Prooxidant
flavonoids
• Chalconaringenin (a nonprenylated chalcone
in citrus fruits)
• Naringenin (a nonprenylated flavanone in
citrus fruits)
• The capacity of flavonoids to act as
antioxidants depends upon their molecular
structure. The position of hydroxyl groups and
other features in the chemical structure of
flavonoids are important for their antioxidant
and free radical scavenging activities.
• Quercetin, the most abundant dietary
flavonol, is a potent antioxidant because it has
all the right structural features for free radical
scavenging activity.
• The antioxidant properties of the
prenylflavonoids were compared to those of
quercetin (a flavonol), genistein (the major
isoflavone in soy), chalconaringenin (a
nonprenylated chalcone), naringenin (a
nonprenylated flavanone), and vitamin E.
• Xanthohumol, the major prenylchalcone in
hops and beer, is a more powerful antioxidant
than vitamin E or genistein. However,
xanthohumol was less potent than quercetin.
The potency of xanthohumol as an antioxidant
is markedly increased when combined with an
equivalent amount of vitamin E.
• A flavonoid chalcone (chalconaringenin) and a
flavanone (naringenin) with no prenyl groups
act as prooxidants, i.e. they promote rather
than limit the oxidation of LDL by copper.
However, adding a prenyl group to these
flavonoid molecules counteracted their
prooxidant activities.
• The specific amounts of flavonols in foods are
affected by a range of factors including plant
type and growth, season, light, degree of
ripeness, food preparation, and processing.
• Despite these variables, high concentrations
of flavonols can be found in apples, apricots,
beans, broad beans, broccoli, cherry
tomatoes, chives, cranberries, kale, leeks,
pear, onions, red grapes, sweet cherries, and
white currants .
Beneficial effects associated with
consumption of flavonols
• Consumption of flavonols has been associated
with a variety of beneficial effects including:
• Increased activity of erythrocyte superoxide
dismutase (an antioxidant enzyme found in
red blood cells)
• A decrease in lymphocyte DNA damage, a
decrease in urinary 8-hydroxy-2’-
deoxyguanosine (a marker of oxidative
damage),
• An increase in plasma antioxidant capacity
(the ability to scavenge free radicals) .
Sources
• Apples: Studies have investigated the
relationship between consumption of apples
and susceptibility to chronic diseases such as:
• Cancer
• CVD
• Asthma
• Diabetes .
• Broccoli: Cruciferous vegetables are part of
the plant family Brassicaceae, which includes:
• Broccoli
• Cabbage
• Cauliflower
• Brussels sprouts
• Turnips
• Watercress.
• Consumption of this group of plant foods has
been associated with a reduction in risk of
several cancers including:
• Lung
• Breast
• Colorectal
• Prostate
• Cranberries: Cranberries are commonly touted
as a remedy for treating urinary tract
infections. Current research has also
investigated the relationship between
consumption of cranberry products and
cancer and cardiovascular disease.
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Flavonoids

  • 2. Flavonoids • Polyphenolic compounds that are ubiquitous in nature and are categorized, according to chemical structure, into flavonols, flavones, flavanones, isoflavones, catechins, anthocyanidins and chalcones
  • 3.
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  • 5.
  • 6.
  • 7. What are flavonols? • Flavonols are phytochemical compounds found in high concentrations in a variety of plant-based foods and beverages. Based on their structure, flavonols are classified as flavonoids and include the following compounds: quercitin, kaempferol, and myricetin.
  • 8. • Over 4,000 flavonoids have been identified, many of which occur in fruits, vegetables and beverages (tea, coffee, beer, wine and fruit drinks).
  • 9. • The flavonoids have aroused considerable interest recently because of their potential beneficial effects on human health they have been reported to have antiviral, antiallergic, antiplatelet, antiinflammatory, antitumor and antioxidant activities.
  • 10. • Antioxidants are compounds that protect cells against the damaging effects of reactive oxygen species, such as singlet oxygen, superoxide, peroxyl radicals, hydroxyl radicals and peroxynitrite.
  • 11.
  • 12.
  • 13. • An imbalance between antioxidants and reactive oxygen species results in oxidative stress, leading to cellular damage. Oxidative stress has been linked to cancer, aging, atherosclerosis, ischemic injury, inflammation and neurodegenerative diseases (Parkinson's and Alzheimer's).
  • 14. • Flavonoids may help provide protection against these diseases by contributing, along with antioxidant vitamins and enzymes, to the total antioxidant defense system of the human body.
  • 15. • Epidemiological studies have shown that flavonoid intake is inversely related to mortality from coronary heart disease and to the incidence of heart attacks.
  • 16. • The recognized dietary antioxidants are vitamin C, vitamin E, selenium, and carotenoids. However, recent studies have demonstrated that flavonoids found in fruits and vegetables may also act as antioxidants.
  • 17. • Like alphatocopherol (vitamin E), flavonoids contain chemical structural elements that may be responsible for their antioxidant activities. The contribution of flavonoids to the antioxidant defense system may be substantial considering that the total daily intake of flavonoids can range from 50 to 800 mg.
  • 18. Dosage • Flavonoid intake depends upon the consumption of fruits, vegetables, and certain beverages, such as red wine, tea, and beer. The high consumption of tea and wine may be most influential on total flavonoid intake in certain groups of people.
  • 19. • This intake is high compared to the average daily intake of other dietary antioxidants like: • vitamin C (70 mg) • vitamin E (710 mg) • or carotenoids (23 mg).
  • 20. Antioxidant flavonoids • Quercetin (a flavonol in vegetables, fruit skins, onions) • Xanthohumol (a prenylated chalcone in hops and beer) • Isoxanthohumol (a prenylated flavanone in hops and beer)
  • 22. • Genistein (an isoflavone in soy) Prooxidant flavonoids • Chalconaringenin (a nonprenylated chalcone in citrus fruits) • Naringenin (a nonprenylated flavanone in citrus fruits)
  • 23. • The capacity of flavonoids to act as antioxidants depends upon their molecular structure. The position of hydroxyl groups and other features in the chemical structure of flavonoids are important for their antioxidant and free radical scavenging activities.
  • 24. • Quercetin, the most abundant dietary flavonol, is a potent antioxidant because it has all the right structural features for free radical scavenging activity.
  • 25. • The antioxidant properties of the prenylflavonoids were compared to those of quercetin (a flavonol), genistein (the major isoflavone in soy), chalconaringenin (a nonprenylated chalcone), naringenin (a nonprenylated flavanone), and vitamin E.
  • 26. • Xanthohumol, the major prenylchalcone in hops and beer, is a more powerful antioxidant than vitamin E or genistein. However, xanthohumol was less potent than quercetin. The potency of xanthohumol as an antioxidant is markedly increased when combined with an equivalent amount of vitamin E.
  • 27. • A flavonoid chalcone (chalconaringenin) and a flavanone (naringenin) with no prenyl groups act as prooxidants, i.e. they promote rather than limit the oxidation of LDL by copper. However, adding a prenyl group to these flavonoid molecules counteracted their prooxidant activities.
  • 28. • The specific amounts of flavonols in foods are affected by a range of factors including plant type and growth, season, light, degree of ripeness, food preparation, and processing.
  • 29. • Despite these variables, high concentrations of flavonols can be found in apples, apricots, beans, broad beans, broccoli, cherry tomatoes, chives, cranberries, kale, leeks, pear, onions, red grapes, sweet cherries, and white currants .
  • 30.
  • 31. Beneficial effects associated with consumption of flavonols • Consumption of flavonols has been associated with a variety of beneficial effects including: • Increased activity of erythrocyte superoxide dismutase (an antioxidant enzyme found in red blood cells)
  • 32. • A decrease in lymphocyte DNA damage, a decrease in urinary 8-hydroxy-2’- deoxyguanosine (a marker of oxidative damage), • An increase in plasma antioxidant capacity (the ability to scavenge free radicals) .
  • 33. Sources • Apples: Studies have investigated the relationship between consumption of apples and susceptibility to chronic diseases such as: • Cancer • CVD • Asthma • Diabetes .
  • 34. • Broccoli: Cruciferous vegetables are part of the plant family Brassicaceae, which includes: • Broccoli • Cabbage • Cauliflower • Brussels sprouts • Turnips • Watercress.
  • 35. • Consumption of this group of plant foods has been associated with a reduction in risk of several cancers including: • Lung • Breast • Colorectal • Prostate
  • 36. • Cranberries: Cranberries are commonly touted as a remedy for treating urinary tract infections. Current research has also investigated the relationship between consumption of cranberry products and cancer and cardiovascular disease.