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Presented by-
Pooja (L-2011-BS-65-D)
Ph.D (Microbiology)
COBS&H, PAU
Ludhiana, Punjab, India.
BIOACTIVE COMPOUNDS IN
ALCOHOLIC BEVERAGES AND THEIR
ROLE IN HUMAN HEALTH
CONTENTS
 Alcoholic beverages
 Bioactive compounds
 Wines as main source of bioactive compounds
 Important bioactive compounds in alcoholic beverages and their
synthesis
 Bioactive compounds’ role in human health
 Antioxidant (antiaging effect)
 Antiaggregation properties
 Cancer chemopreventive and chemotheraupatic agents
 Cardioprotective action
 Neurodegenerative protection
 Conclusion
 Future prespectives
 Any fermented liquor that contains ethyl
alcohol as an intoxicating agent.
Alcoholic
beverages
Beer Wine Spirit
Distilled v/s undistilled beverages
•Relatively harsh
• Don’t contain any
nutritional compounds
Distilled
beverages
•Health friendly
• Contain high amount of
nutritional constituents
Undistilled
Beverages
WINE AS MAIN SOURCE OF
BIOACTIVE COMPOUNDS
 Wine contains enormous amount of health promoting biologically
active compounds.
 In comparison to beer, wine seems to have more health benefits due
presence of various flavonoids, non-flavonoids and anthocyanins.
Bioactive
compound
Red wine White wine Beer
Flavonoids 5.9±1.6 mg/L 2.3± 1.2 mg/L 1.3±0.2 mg/L
Non-flavonoids 5.4±2.8 mg/L 2.7±1.1 mg/L 1.8±0.3 mg/L
Anthocyanins 4.7±2.6 mg/l ND ND
FRENCH PARADOX
 By Renauld and De lorgeril (1992)
 A Dutch epidemiological study showed inverse
relationship between-
“Large intake of wine lead to low mortality rate from
cardiovascular diseases among French people despite
their high consumption of saturated fats”
Flavonoids
intake
Coronary
heart
diseases
(Fernandz et al
Bioactive compounds
 Biologically active compounds
 Extra nutritional constituents
 Occur in small quantity in foods
 Health stimulating – therapeutic benefits
(Kris-Etherton et al
FLAVONOIDS
NON FLAVONOIDS
Hydroxycinnammic acids
Stilbenes
Phenolic acids
Flavonols
Anthocyani
ns
Tannins
THREE MAJOR BIOACTIVE COMPOUNDS IN
WINE
 RESVERATROL
 HYDROXYTYROSOL
 MELATONIN
A stillbene; synthesize
from phenylalanine
through shikimic acid
pathway
A phenyl ethyl alcohol;
synthesized from tyrosol
An indolamine;
synthesized from
tryptophan
(Fernandz et al
SYNTHESIS OF
RESVERATROL
 3,5,4 -trans-trihydroxystillbene
 Found in skin and seed of
grapes
Three key enzymes are
involved in this pathway:
phenylalanine ammonium
lyase, coenzyme A ligase and
stilbene synthase
Derivatives: piceid,
pterostilbene, ε-viniferin, and δ-
viniferin
 Concentration in wine -
2.7 1.5 mg/L
Bioactive compounds in alcoholic beverages and their role in human health
SYNTHESIS OF HYDROXYTYROSOL
 2-(3,4-dihydroxyphenyl)
ethanol (3,4-DHPEA)
Found in grapes seeds
and olives
Synthesized from tyrosol
and oleuropein
 Concentration in wine-
5.3 ± 0.2 mg/L
SYNTHESIS OF MELATONIN
N-acetyl-5-methoxytryptamine
Melatonin synthesized from
tryptophan via 5-
hydroxytryptophan, serotonin
and N-acetylserotonin and to be
metabolized by deacetylation to
5-methoxytryptamine .
In yeast, melatonin can also
be formed by O-methylation of
serotonin followed by N-
acetylation of 5-
methoxytryptamine.
Concentration in wine - 0.5 ±
0.4 ng/L
HEALTH PROMOTING PROPERTIES
 Antioxidant activity
 Cardioprotective capacity
 Anticancer activity
 Antiaggregation activity
 Neuroprotective activity
FREE RADICALS; REACTIVE
SPECIES
Normal cellular metabolism generates oxygen intermediates-
 Superoxide(O2
-)
 Hydrogen peroxide (H2O2)
 Hydroxyl radical (OH•)
Oxidative stress and defense
mechanism of cell
ANTIOXIDANT ACTIVITY
 Bioactive compounds act as free radical scavengers by
acting reducing agent (donating the H atom).
 Chelation of transition metal ions by bioactive compounds
diminishes the capacity of metal ions to generate reactive
oxygen radicals in Fenton reaction.
Antioxidants Mop Up Loose Free
Radicals
+ OH
OH OH
+ H2O
O O
Antioxidant Free Radical
Antioxidant Capabilities of Resveratrol
and Hydroxytyrosol
Wines ORAC value (mm TE/L)
Red wine 14.60 ± 5.76
White wine 3.37 ± 1.04
(Arranz et al 2012)
Chelation of Cu2+ ions by
polyphenols
Chelated copper
ion by
polyphenols
Resveratrol activates the Antiaging
gene
 Sirtuins; family of NAD-
dependent deacetylase.
 SIRT 1-SIRT7 promotes
stress resistance and
survival in times of
adversity and adaptability.
 Resveratrol activates the
antiaging gene Sirt1by 13
folds.
BIOACTIVE COMPOUNDS INCREASES THE
HIGH-DENSITY LIPOPROTEIN CONTENT
 HDL – required for transport of cholesterol from arteries and other body parts
back to the liver for its metabolism.
 HDL; protective against arteriosclerosis.
Resveratrol action
(Das et al 2009)
CARDIOPROTECTIVE ACTIVITY
 Bioactive compounds protects the cardiovascular
system in multidimensional way.
Resveratrol - At low concentration
• Inhibits apopotic cell death
Resveratrol – At high concentration
• Facilitates apopotic cell death
Behave as a
chemopreventiv
e alternative
ETHANOL ALSO ACTS AS A
CARDIOPROTECTIVE AGENT
Ethanol reduces the calcium influx
and release
Ethanol activates coronary vascular
smooth muscles by modulating Ca2+
metabolism
Decrease in Ca2+ influx through voltage-
dependent and receptor mediated Ca2+
channels in sarcolemmal membrane and
decrease in Ca2+ release from sarcoplasmic
reticulum.
As a result, ethanol dilates the coronary
arteries and increases the coronary flow
leading to cardioprotection
(Das et al 2009)
Resveratrol action towards
cardioprotection
Reseveratrol mediates the
vasorelaxation by-
• Endothelial-dependent pathway
• Endothelial-independent
pathway
Endothelial-dependent
• Increase in eNOS (endothelial
nitric oxidee synthase) activity
• Release of NO (Nitric) enzyme;
modulates vascular tone
Endothelial-independent
• Release of K+ ions
• Energy in form of ATP is required
ANTIINFLAMMATORY
ACTIVITY
 Arachidonic acid (stored in cell membranes of mammalian
cells) is transformed into powerful pro-inflammatory and
platelet aggregating thromboxanes through cycloygenase
(COX) and to leukotrienes through lipoxygenase (LOX)
enzymes.
 50% Inhibition concentrations (IC 5O) for both resveratrol
and quercetin are approximately 100µM.
 Other antioxidants, vitamin E and BHT are ineffective at
inhibiting platelet aggregation.
Bioactive compounds in alcoholic beverages and their role in human health
INHIBITION OF COX AND LOX
ENZYMES
Resveratro
l
Resveratr
ol
Resveratr
ol
ANTIAGGREGATION
PROPERTIES
Cell membrane phospholipids
Arachidonic acid
Prostaglandin G1
Prostaglandins H2
prostacyclins
prostaglandin
s
Cycloxygenase
Resveratrol
•Pro-infammatory
•Platelet aggregation
Thromboxane
A2
ANTICANCER ACTIVITY
By Inhibition of polymearse DNA
ornithine decarboxylase enzyme
By antiproliferative effect
By inhibition of COX enzyme
By inducing apoptosis of cancer cells
Bioactive compounds inhibit the
carcinogenesis at multiple stages-
initiation promotion progression
Contd
..
 Anti-initiation activity of bioactive compounds is because of their anti-
inflammatory and antimutagenic effects.
 Anti-promotion activity corresponds by inhibiting the action of carcinogens.
 Anti-progression activity by decreasing the MMPS (Metalloproteinases) and
VEGF(Vascular endothelial growth factor) action.
 Resveratrol induces apoptosis in human breast carcinoma and human leukemia
cells.
 Oral administration of 25µM of resveratrol and 30-32 µM of hydroxytyrosol lead
to 70% growth inhibition of cancerous cells.
(Arranz et al 2012)
NEUROPROTECTIVE
ACTIVITY
 Bioactive compounds have neuroprotective activity due to
their anti-inflammatory, estrogenic and hypolipemic
properties.
 They lowers the levels of amyloid-β peptides (formed by non-
amyloidogenic pathways) whose aggregation leads to telltale
senile plaques of Alzheimer’s disease and Parkinson’s
disease.
 Bioactive compounds stimulates the degradation of amyloid-
β peptides by proteasome; a barrel shaped multiprotein
complex that specifically digest proteins to small peptides
and amino acids.
(Fernandz et al 2012)
AMYLOID-β PEPTIDES FORMATION AND
THEIR DIGESTION BY PROTEASOME
Contd..
 Bioactive compounds are capable of crossing
blood-brain barrier and exerts strong
neuroprotection; even at low doses.
 Consumption of 500nM resveratrol/day -
needed to protect neurons.
COMMERCIAL FORMULATIONS
AVAILABLE IN THE MARKET
 Impressive progress is being made in defining the role of
bioactive compounds in reducing the risk of major
chronic diseases.
 Moderate wine consumption have antiaging, anti-
inflammatory, cardioprotective, neuroprotective
activites.
 National Institute on Alcohol Abuse and Alcoholism
(NIAAA) reported that moderate drinkers have the
greatest longevity. Drinking alcohol in moderation (1-2
drinks per day for women and 2-3 for men) was found to
reduce risk of mortality significantly.
FUTURE PRESPECTIVES
 A deep study of bioavailability and pharmacokinetics of
bioactive compounds is required in humans.
 Various oenological practices and fermentative parameters
(skin contact and maceration of grapes) need to be optimized
for effective extraction of these bioactive compounds in wines.
 Awareness amongst the people to differentiate between the
benefits of undistilled and harmful effects of distilled
beverages.
Bioactive compounds in alcoholic beverages and their role in human health

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Bioactive compounds in alcoholic beverages and their role in human health

  • 1. Presented by- Pooja (L-2011-BS-65-D) Ph.D (Microbiology) COBS&H, PAU Ludhiana, Punjab, India. BIOACTIVE COMPOUNDS IN ALCOHOLIC BEVERAGES AND THEIR ROLE IN HUMAN HEALTH
  • 2. CONTENTS  Alcoholic beverages  Bioactive compounds  Wines as main source of bioactive compounds  Important bioactive compounds in alcoholic beverages and their synthesis  Bioactive compounds’ role in human health  Antioxidant (antiaging effect)  Antiaggregation properties  Cancer chemopreventive and chemotheraupatic agents  Cardioprotective action  Neurodegenerative protection  Conclusion  Future prespectives
  • 3.  Any fermented liquor that contains ethyl alcohol as an intoxicating agent. Alcoholic beverages Beer Wine Spirit
  • 4. Distilled v/s undistilled beverages •Relatively harsh • Don’t contain any nutritional compounds Distilled beverages •Health friendly • Contain high amount of nutritional constituents Undistilled Beverages
  • 5. WINE AS MAIN SOURCE OF BIOACTIVE COMPOUNDS  Wine contains enormous amount of health promoting biologically active compounds.  In comparison to beer, wine seems to have more health benefits due presence of various flavonoids, non-flavonoids and anthocyanins. Bioactive compound Red wine White wine Beer Flavonoids 5.9±1.6 mg/L 2.3± 1.2 mg/L 1.3±0.2 mg/L Non-flavonoids 5.4±2.8 mg/L 2.7±1.1 mg/L 1.8±0.3 mg/L Anthocyanins 4.7±2.6 mg/l ND ND
  • 6. FRENCH PARADOX  By Renauld and De lorgeril (1992)  A Dutch epidemiological study showed inverse relationship between- “Large intake of wine lead to low mortality rate from cardiovascular diseases among French people despite their high consumption of saturated fats” Flavonoids intake Coronary heart diseases (Fernandz et al
  • 7. Bioactive compounds  Biologically active compounds  Extra nutritional constituents  Occur in small quantity in foods  Health stimulating – therapeutic benefits (Kris-Etherton et al
  • 9. THREE MAJOR BIOACTIVE COMPOUNDS IN WINE  RESVERATROL  HYDROXYTYROSOL  MELATONIN A stillbene; synthesize from phenylalanine through shikimic acid pathway A phenyl ethyl alcohol; synthesized from tyrosol An indolamine; synthesized from tryptophan (Fernandz et al
  • 10. SYNTHESIS OF RESVERATROL  3,5,4 -trans-trihydroxystillbene  Found in skin and seed of grapes Three key enzymes are involved in this pathway: phenylalanine ammonium lyase, coenzyme A ligase and stilbene synthase Derivatives: piceid, pterostilbene, ε-viniferin, and δ- viniferin  Concentration in wine - 2.7 1.5 mg/L
  • 12. SYNTHESIS OF HYDROXYTYROSOL  2-(3,4-dihydroxyphenyl) ethanol (3,4-DHPEA) Found in grapes seeds and olives Synthesized from tyrosol and oleuropein  Concentration in wine- 5.3 ± 0.2 mg/L
  • 13. SYNTHESIS OF MELATONIN N-acetyl-5-methoxytryptamine Melatonin synthesized from tryptophan via 5- hydroxytryptophan, serotonin and N-acetylserotonin and to be metabolized by deacetylation to 5-methoxytryptamine . In yeast, melatonin can also be formed by O-methylation of serotonin followed by N- acetylation of 5- methoxytryptamine. Concentration in wine - 0.5 ± 0.4 ng/L
  • 14. HEALTH PROMOTING PROPERTIES  Antioxidant activity  Cardioprotective capacity  Anticancer activity  Antiaggregation activity  Neuroprotective activity
  • 15. FREE RADICALS; REACTIVE SPECIES Normal cellular metabolism generates oxygen intermediates-  Superoxide(O2 -)  Hydrogen peroxide (H2O2)  Hydroxyl radical (OH•)
  • 16. Oxidative stress and defense mechanism of cell
  • 17. ANTIOXIDANT ACTIVITY  Bioactive compounds act as free radical scavengers by acting reducing agent (donating the H atom).  Chelation of transition metal ions by bioactive compounds diminishes the capacity of metal ions to generate reactive oxygen radicals in Fenton reaction.
  • 18. Antioxidants Mop Up Loose Free Radicals + OH OH OH + H2O O O Antioxidant Free Radical
  • 19. Antioxidant Capabilities of Resveratrol and Hydroxytyrosol Wines ORAC value (mm TE/L) Red wine 14.60 ± 5.76 White wine 3.37 ± 1.04 (Arranz et al 2012)
  • 20. Chelation of Cu2+ ions by polyphenols Chelated copper ion by polyphenols
  • 21. Resveratrol activates the Antiaging gene  Sirtuins; family of NAD- dependent deacetylase.  SIRT 1-SIRT7 promotes stress resistance and survival in times of adversity and adaptability.  Resveratrol activates the antiaging gene Sirt1by 13 folds.
  • 22. BIOACTIVE COMPOUNDS INCREASES THE HIGH-DENSITY LIPOPROTEIN CONTENT  HDL – required for transport of cholesterol from arteries and other body parts back to the liver for its metabolism.  HDL; protective against arteriosclerosis.
  • 24. CARDIOPROTECTIVE ACTIVITY  Bioactive compounds protects the cardiovascular system in multidimensional way. Resveratrol - At low concentration • Inhibits apopotic cell death Resveratrol – At high concentration • Facilitates apopotic cell death Behave as a chemopreventiv e alternative
  • 25. ETHANOL ALSO ACTS AS A CARDIOPROTECTIVE AGENT
  • 26. Ethanol reduces the calcium influx and release Ethanol activates coronary vascular smooth muscles by modulating Ca2+ metabolism Decrease in Ca2+ influx through voltage- dependent and receptor mediated Ca2+ channels in sarcolemmal membrane and decrease in Ca2+ release from sarcoplasmic reticulum. As a result, ethanol dilates the coronary arteries and increases the coronary flow leading to cardioprotection (Das et al 2009)
  • 27. Resveratrol action towards cardioprotection Reseveratrol mediates the vasorelaxation by- • Endothelial-dependent pathway • Endothelial-independent pathway Endothelial-dependent • Increase in eNOS (endothelial nitric oxidee synthase) activity • Release of NO (Nitric) enzyme; modulates vascular tone Endothelial-independent • Release of K+ ions • Energy in form of ATP is required
  • 28. ANTIINFLAMMATORY ACTIVITY  Arachidonic acid (stored in cell membranes of mammalian cells) is transformed into powerful pro-inflammatory and platelet aggregating thromboxanes through cycloygenase (COX) and to leukotrienes through lipoxygenase (LOX) enzymes.  50% Inhibition concentrations (IC 5O) for both resveratrol and quercetin are approximately 100µM.  Other antioxidants, vitamin E and BHT are ineffective at inhibiting platelet aggregation.
  • 30. INHIBITION OF COX AND LOX ENZYMES Resveratro l Resveratr ol Resveratr ol
  • 31. ANTIAGGREGATION PROPERTIES Cell membrane phospholipids Arachidonic acid Prostaglandin G1 Prostaglandins H2 prostacyclins prostaglandin s Cycloxygenase Resveratrol •Pro-infammatory •Platelet aggregation Thromboxane A2
  • 32. ANTICANCER ACTIVITY By Inhibition of polymearse DNA ornithine decarboxylase enzyme By antiproliferative effect By inhibition of COX enzyme By inducing apoptosis of cancer cells Bioactive compounds inhibit the carcinogenesis at multiple stages- initiation promotion progression
  • 33. Contd ..  Anti-initiation activity of bioactive compounds is because of their anti- inflammatory and antimutagenic effects.  Anti-promotion activity corresponds by inhibiting the action of carcinogens.  Anti-progression activity by decreasing the MMPS (Metalloproteinases) and VEGF(Vascular endothelial growth factor) action.  Resveratrol induces apoptosis in human breast carcinoma and human leukemia cells.  Oral administration of 25µM of resveratrol and 30-32 µM of hydroxytyrosol lead to 70% growth inhibition of cancerous cells. (Arranz et al 2012)
  • 34. NEUROPROTECTIVE ACTIVITY  Bioactive compounds have neuroprotective activity due to their anti-inflammatory, estrogenic and hypolipemic properties.  They lowers the levels of amyloid-β peptides (formed by non- amyloidogenic pathways) whose aggregation leads to telltale senile plaques of Alzheimer’s disease and Parkinson’s disease.  Bioactive compounds stimulates the degradation of amyloid- β peptides by proteasome; a barrel shaped multiprotein complex that specifically digest proteins to small peptides and amino acids. (Fernandz et al 2012)
  • 35. AMYLOID-β PEPTIDES FORMATION AND THEIR DIGESTION BY PROTEASOME
  • 36. Contd..  Bioactive compounds are capable of crossing blood-brain barrier and exerts strong neuroprotection; even at low doses.  Consumption of 500nM resveratrol/day - needed to protect neurons.
  • 38.  Impressive progress is being made in defining the role of bioactive compounds in reducing the risk of major chronic diseases.  Moderate wine consumption have antiaging, anti- inflammatory, cardioprotective, neuroprotective activites.  National Institute on Alcohol Abuse and Alcoholism (NIAAA) reported that moderate drinkers have the greatest longevity. Drinking alcohol in moderation (1-2 drinks per day for women and 2-3 for men) was found to reduce risk of mortality significantly.
  • 39. FUTURE PRESPECTIVES  A deep study of bioavailability and pharmacokinetics of bioactive compounds is required in humans.  Various oenological practices and fermentative parameters (skin contact and maceration of grapes) need to be optimized for effective extraction of these bioactive compounds in wines.  Awareness amongst the people to differentiate between the benefits of undistilled and harmful effects of distilled beverages.