PBRC 2005

Cocoa Polyphenols
Pennington Biomedical Research Center
Division of Education

Heli Roy, PhD
Shanna Lundy, BS
Phillip Brantley, PhD- Chief
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Overview

An increasing body of epidemiologic evidence supports the concept
that diets rich in fruits and vegetables promote health and attenuate,
or delay, the onset of various diseases, including cardiovascular
disease, cancer, and certain neurodegenerative disorders

Epidemiologic data has linked these health benefits, at least in part,
to the presence of certain flavonoids in fruits and vegetables
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Flavonoids are a group of polyphenolic compounds that occur widely
in fruits, vegetables, tea, red wine, and chocolate

Cocoa and chocolate products have the highest concentration of
flavonoids among commonly consumed foods

Over 10 percent of the weight of cocoa powder is flavonoids

Flavonoids
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Cocoa and chocolate products have been delicacies for
hundreds

of years

Cocoa and chocolate have only recently have they been recognized
as significant sources of phytochemicals, with healthful effects

Cocoa and chocolate are among the most concentrated sources of
the procyanidin flavonoids,

catechin and epicatechin

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Americans eat a lot of chocolate in the form of candy
(about 4.6 kg/year per person or 10 pounds), but not as
much as people in some northern European countries

In Switzerland, the country with the highest chocolate
consumption, it is estimated at 9.9 kg/year (22 pounds)
for each person

Each candy bar contains about 210 calories, 13 g fat (7
of which is saturated), 23 g of carbohydrate, and 3 g of
protein
Chocolate Candy Consumption
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Chocolate and cocoa are unique in the type of
flavonoids present

The flavonoids in cocoa/chocolate, principally
catechin

and epicatechin, exist in long polymers

They contain

two, three, or up to ten of the
catechin or epicatechin units

linked, which is fairly
distinctive, since most flavonoid-rich

foods tend to
have more catechins and epicatechins in dimers

or trimers, not pentamers, hexamers, etc

Flavonoids in Chocolate
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Also intriguing is

the chemistry of flavonoids in
cocoa which are really R-oligomers

These structural characteristics of catechin and
epicatechin represent the molecular basis for both
their hydrogen-donating (radical-scavenging)
properties and their metal-chelating antioxidant
properties


Flavonoids in Chocolate
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As with most plants, genetic and agronomic factors can
markedly influence the contents of phytochemicals

available at the time of harvest

Postharvest handling also plays

a critical role, because
most cocoas undergo

some fermentation steps, which
subject flavonoids in the cocoa

to heat and acidic
conditions

Subsequent processing steps,

such as roasting and alkali
treatment, can also reduce the flavonoid

contents

Flavonoid Content:
Is Variable
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The actual recipe for the finished food or beverage

product
determines the amount of a given cocoa (and flavonoid)

added.

Depending on harvesting and processing procedures,
as

much as 90% of the flavonoids can be lost during processing



Flavonoid Content
Is Variable
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Different types of chocolate contain varying antioxidant content

In finished products, the amount of cocoa ranges from
7% to 35% in milk chocolate and 30% to 80% in dark chocolate

Consequently, the polyphenol content varies and is generally
twice as high in dark than in milk chocolate

Also interesting is the fact that white chocolate does not contain
polyphenols
Flavonoid Content
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Recently, Joe Vinson at the University of
Scranton (PA), who has been studying total
polyphenols in foods and beverages in the
American diet, has found even higher levels of
antioxidants in chocolate

His studies have shown that on a weight basis,
the concentration of polyphenols in milk
chocolate is higher than in red wines and black
or green teas. It is 20 times higher than in
tomatoes, 2 times higher than in garlic, and over
3 times higher than in grapes.
Recent Studies
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Beverages: Tea (green and black), red wine, grape, tomato,
orange, and apple juice

Top 10 vegetables: Garlic, kale, spinach, Brussels sprouts, alfalfa
sprouts, broccoli flowers, beets,
red bell peppers, onions, and corn

Top 10 fruits: Strawberry, plum, orange, red grapes, kiwi fruit,
pink grapefruit, white grapes, banana, apple,
tomato

Foods High in Antioxidants
In addition to chocolate, the following foods and beverages are high in antioxidants:
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Numerous dietary intervention studies in humans and animals indicate
that flavanol-rich foods and beverages might exert cardioprotective
effects with respect to vascular function and platelet reactivity.
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Antioxidant Capacity
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Phenolic antioxidants have been
shown to inhibit the oxidation of low-
density lipoprotein (LDL) cholesterol,
and mounting evidence suggests
that it is the oxidized form of LDL
that leads to the buildup of fatty
plaques in arteries
Atherogenesis
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Extracts of cocoa powder have also significantly inhibited LDL
oxidation in vitro

Kondo et. Al. reported that cocoa prolongs the lag time of LDL
oxidation in a concentration-dependent manner

Cocoa phenols has shown to inhibit LDL oxidation by 75%,
whereas red wines only inhibit LDL oxidation by 37-65%

Atherogenesis
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Interestingly, cocoa powder and cocoa extracts

have been shown to
exhibit greater antioxidant capacity than

many other flavanol-rich
foods and food extracts, such as green

and black tea, red wine,
blueberry, garlic, and strawberry in vitro

However, no long-term studies have evaluated the effects of cocoa
polyphenol compounds on the oxidative modification of LDL in
humans
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Short-term human studies
Researchers set out to test whether or not these
effects shown from in vitro studies could be seen
in humans

The levels of epicatechin and catechin were
measured in humans at zero, one, two, and six
hours following consumption of a single meal of
chocolate

The concentration in plasma levels peaked at
about one hour; however, by six hours the
concentrations had almost disappeared from the
plasma

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Same Effects in Humans?
Indicated that cocoa flavonoids are absorbed and cleared
from circulation relatively quickly

Support the recommendations to consume several
servings of fruit and vegetables per day as seen in a
number of clinical trials with chocolate and other
flavonoid-rich foods,

Spacing intake of flavonoid-rich foods throughout the day
could help to provide a continuous supply
Short-term human studies
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Because there is six to seven times more epicatechin
than catechin in cocoa/chocolate, most attention has
focused on epicatechin in studies

Consistent with in vitro studies, human studies
indicate that small doses of epicatechin are effective

There is a statistically significant increase in plasma
antioxidant capacity and reduction in lipid peroxides
following cocoa/chocolate consumption
More studies
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Epicatechin and other flavonoids not only have a
direct antioxidant effect, but they may also have a
sparing effect on other antioxidants such as
Vitamins C and E
Benefits
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Although flavanol-rich cocoa and chocolate have the potential to
augment an individuals antioxidant defense system, there are other
cellular mechanisms through which these flavanol-rich foods can
affect cardiovascular health:


Inflammation
Platelet aggregation
Nitric oxide (NO)-mediated endothelial changes
Other Mechanisms
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Inflammation
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Atherosclerosis and heart failure, as well as risk factors such

as
hypertension and hypercholesterolemia, can activate several

proinflammatory enzyme systems, such as xanthine oxidase,
NADH/NADPH oxidase, and myeloperoxidase

Once activated, these enzymes

produce reactive oxygen species and
other radicals that, as

indicated above, can modify NO availability
and LDL and contribute

to endothelial dysfunction

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Flavanol-rich cocoa liquor

has been shown to stimulate NO
production and to significantly

reduce the activities of xanthine
oxidase and myeloperoxidase

after ethanol-induced oxidative stress

In addition, cocoa

flavanols and procyanidins may modulate other
mediators of inflammation

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Platelets
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In addition to its influence on oxidative defense mechanisms,
polyphenols seem to benefit cardiovascular health in other ways-
through regulation of platelet reactivity

Given the prominent role of platelets in the development and
manifestation of acute myocardial infarction, stroke, and venous
thromboembolism, antiplatelet strategies are an important
consideration

A modest decrease in platelet reactivity can be of value because it
reduces the probability of clotting


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In one study to determine whether cocoa inhibits platelet activation
and function, subjects were given either water or 300 ml of cocoa
that provided a very high amount of polyphenols

During the six hour time period following intake of cocoa, there was a
reduction in P-selectin, suggestive of less reactive platelets

This is the same response that would be seen following intake
of antiplatelet agents such as aspirin


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Endothelium
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Shear stress, ischemia and reperfusion, inflammation, and
disease

states, such as atherosclerosis, diabetes mellitus,
and hypertension,

can disrupt endothelial function

This is associated with alterations

in endothelium-derived
regulatory mediators, an inability to

regulate vascular tone,
and an overall shift toward the prothrombotic

state

Possible that flavanols, by functioning as antioxidants,

in
addition to modulating prostacylin and leukotriene
concentrations, can improve endothelial function through the
prevention

and possible reduction of oxidative damage

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Conclusions

Although in vitro studies provide strong support for the hypothesis
that flavanol-rich food consumption is associated with the reduced
risk for vascular diseases, at this time the majority of studies that
have been reported are in the form of short-term clinical trials

The health benefits of these nutrients will best be determined from
long-term, randomized, clinical trials
Keen C, et al. Dietary polyphenols and health: Proceedings of the 1
st

international conference on polyphenols and health. Amer J Clin
Nutr. 2005. 81:1 298S-303S. Available at:
http://www.ajcn.org/cgi/content/full/81/1/298S

Keen C. Chocolate: Food as medicine/medicine as food. J Amer Coll
of Nutr. 2001. 20:90005 436S-439S. Available at:
http://www.jacn.org/cgi/content/full/20/suppl_5/436S

Wan Y, et al. Effects of cocoa powder and dark chocolate on LDL
oxidative susceptibility and prostaglandin concentrations in humans.
Amer J Clin Nutr. 2001. 74:5 596-602. Available at:
http://www.ajcn.org/cgi/content/full/74/5/596
References
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http://pubs.acs.org/hotartcl/tcaw/99/jul/chocolate.html

http://sciweb.nybg.org/science2/pdfs/mb/chocolate.pdf#search='alter
native%20therapies%20sept/oct%20chocolate

References