History Of Oligomeric Proanthocyanidins (OPCs)
Other Common Names: Grape seed extract, Oligomeric Proanthocyanidins (OPCs), Procyanidolic Oligomers (PCOs), Pycnogenol, Procyanidins
During the winter of 1534, the French explorer Jacques Cartier and his crew avoided
scurvy by using Anneda, an Indian medicine probably containing ascorbic acid and
procyanidins. Four centuries later, Szent-Gyorgyi was misguided in proposing citrin [lemon
flavonoid compound] as a second antiscorbutic factor, for flavonoids are devoid of true
vitamin-like behavior. On the other hand, pycnogenols, widely found in old empirical
antiscorbutic remedies, seem more appropriate in this respect, since they are active per
os, bioavailable, linked to various living tissues, and concerned with essential metabolic
pathways. As histidine decarboxylase inhibitors, pycnogenols lower the histamine level in
the aortic endothelium and are believed to protect it against the vascular permeability
alterations occurring early in the atherogenic process.
In 1947, a student at the biological and medical faculty of the University of Bordeaux,
France named Jack Masquelier was assigned the task of determining whether or not the red
inner skin of peanuts was toxic. For his doctoral dissertation, Masquelier undertook a
series of experiments to answer this question. Fairly early in his investigations,
Masquelier was able to determine that in fact peanut skins were not toxic. In the course
of his research, however, he came upon a colorless substance in peanut skin which called
for further examination. By 1948, he had succeeded in isolating that substance, OPC, from
peanut skin, and had identified that it possessed vasoprotective (protective of blood
vessels) potential. After casting about among many possible sources, he found what he was
searching for in the bark of Landes pine trees, a waste product of the lumber industry
typically used as a mulch for gardens. This new source yielded sufficient quantifies of
OPC to be useful for manufacturing purposes.
Subsequent studies by Masquelier eventually revealed another source of OPC besides the
bark of the Landes pine. Grape seeds, which are the waste product of the winemaking
industry and are used to make grape seed oil for cooking, were found to contain even
greater amounts of the same beneficial antioxidant. Though grape seeds did not supplant
pine bark completely, they came to be the primary source of OPC for extraction. Today in
France, Flavan, from Landes pine bark, and Resivit from grape seeds, are both registered
OFC medicines for vascular protection.
Mainstream medical science now regards oxidation as a primary cause of degeneration and
ageing. Oxidation, the slow deterioration of matter as a result of chemical reactions
involving oxygen, is a familiar phenomenon found throughout nature. The rusting of metals,
the spoilage of foods, the rancidification of oils and the crumbling of rubber are
examples of the common process of oxidation. In the body oxidative reactions of many kinds
occur due to exposure to environmental toxins. In the air we breathe and the water we
drink, we are exposed to as many as 60,000 chemical toxins of different kinds, including
cigarette smoke, car exhaust vapors from cleaning fluids and solvents. Some chemical
agents, such as the trihalomethanes, are toxic in quantities almost too small to be
detected. In addition, we are subjected to a variety of chemical food additives such as
preservatives, artificial colors, flavors emulsifiers, lubricants, bleaching agents,
flavor enhancers and synthetic sweeteners. Many of these agents con
tribute to oxidative reactions in the body.
Fortunately, there are nutritional agents that help to prevent against oxidative damage
in the body and fight free radicals, and further help to repair damage that has already
occurred. Antioxidant dietary factors include nutrients such as tocopherol (vitamin E) and
ascorbate (vitamin C), as well as numerous carotenoids and a number of phenols and
flavonoids found in common foods. Dietary fruits and vegetables are the primary sources of
antioxidant dietary factors, though some antioxidants occur in grains, beans, meats,
seafood's and dairy products. But while antioxidants are available in a healthy diet it is
difficult to get enough of them to fend off the damage caused by free radicals resulting
from air and water pollution and other environmental factors.
In terms of protective value, Dr Masquelier's OPC is a superior antioxidant. OPC is
very rapidly absorbed, and is quickly distributed throughout the body as a free radical
fighter, OPC comes to the aid of the body more quickly than other antioxidants, thereby
reducing the potential for free radical damage and the ravages of aging. OPC also
possesses more reactive sites for neutralising free radicals than other known
antioxidants. Furthermore, OPC possesses nucleophilic as well as electrophilic reactive
centers, permitting reactivity with both positively charged and negatively charged free
radical species. what this means is that OPC can "scavenge" or "quench" (neutralize) a
broad variety of types of free radicals.
Considerable recent research has explored therapeutic applications of oligomeric
proanthocyanidin complexes (OPCs), naturally occurring plant metabolites widely available
in fruits, vegetables, nuts, seeds, flowers, and bark. OPCs are primarily known for their
antioxidant activity. However, these compounds have also been reported to demonstrate
antibacterial, antiviral, anticarcinogenic, anti-inflammatory, anti-allergic, and
vasodilatory actions. In addition, they have been found to inhibit lipid peroxidation,
platelet aggregation, capillary permeability and fragility, and to affect enzyme systems
including phospholipase A2, cyclooxygenase, and lipoxygenase. Based on these reported
findings, OPCs may be a useful component in the treatment of a number of conditions
including venous insufficiency, varicose veins, capillary fragility and diabetic
retinopathy. Experimental studies suggest potential benefit in arteriosclerosis, heart
disease and stroke.
Proanthocyanidins (Procyanidins) is an important therapeutic class of flavonoids
extracted from grape seeds and maritime (Landes) pine. When individual molecules bind
together, the result is collectively called procyanidolic oligomers (PCO). They have a
broad range of pharmacologic activity through increasing vitamin C levels, decreasing
capillary permeability and fragility, scavenging free radicals and inhibiting destruction
of collagen. The latter occurs through ability to cross-link collagen fibers, preventing
free-radical damage, inhibiting enzymatic cleavage of collagen, and preventing the
synthesis and release of inflammatory mediators. PCO has approximately 50 times the
anti-oxidant activity of vitamin C or vitamin E. These influences, along with other
mechanisms, explain their benefit in venous and capillary disorders, including venous
insufficiency, capillary fragility, diabetic retinopathy and macular degeneration.
Studies show that PCO also lowers cholesterol levels and can shrink arterial choles
terol deposits.
Grape seed proanthocyanidins are natural antioxidants which possess a broad spectrum of
chemoprotective properties against free radicals and oxidative stress.
There is increasing evidence to indicate cardioprotective effects of red wine
consumption. Such cardioprotective properties of wine have been attributed to certain
polyphenolic constituents of grapes. The purpose of this investigation was to examine
whether proanthocyanidins derived from grape seeds possess cardioprotective properties.
The results of our study demonstrated that proanthocyanidin-fed animals were resistant to
myocardial ischemia reperfusion injury as evidenced by improved recovery of post-ischemic
contractile functions. The proanthocyanidin-fed group revealed reduced extent of
myocardial infarction compared to the control group. Fluorimetric study demonstrated the
antioxidant property of proanthocyanidin as judged by its ability to directly scavenge
peroxyl radicals. Taken together, the results of this study showed that grape
seed-proanthocyanidins possess a cardioprotective effect against ischemia reperfusion
injury. Such cardioprotective property, at least in part, may be attributed to its
ability to directly scavenge peroxyl and hydroxyl radicals and to reduce oxidative stress
developed during ischemia and reperfusion.
Reactivities of several proanthocyanidins (monomers of condensed
tannins) and gallate esters (representing hydrolyzable tannins) with
hydroxyl radicals, azide radicals, and superoxide anions were
investigated using pulse radiolysis combined with kinetic spectroscopy.
We determined the scavenging rate constants and the decay kinetics of
the aroxyl radicals both at the wavelength of the semiquinone
absorption (275 nm) and the absorption band of the gallate ester ketyl
radical (400-420 nm). For most compounds second-order decay kinetics
were observed, which reflect disproportionation of the semiquinones. In
the case of the oligomeric hydrolysable tannins, pentagalloyl glucose
and tannic acid, the decay kinetics were more complex involving
sequential first-order and second-order reactions, which could only be
resolved by kinetic modeling. A correlation of the reaction rates with
hydroxyl radicals (k*OH) with the number of adjacent aromatic hydroxyl
groups (i.e., representing catechol and/or pyrogallol structures) was
obtained for both condensed and hydrolyzable tannins. Similar
correlation for the reactions with azide radicals and superoxide anions
are less obvious, but exist as well. We consider proanthocyanidins
superior radical scavenging agents as compared with the monomeric
flavonols and flavones and propose that these substances rather than
the flavonoids proper represent the antioxidative principle in red wine
and green tea.
The pharmacological treatment of non-complicated chronic venous insufficiency is a
current and well-debated topic. The introduction of new products with action on the venous
system, improved knowledge on the physiopathology of venous insufficiency and the
possibility provided by new analytical instruments, have given new impulse to the
consolidation of the clinical value of phlebotonics in this indication.
Methods: In light of this, 24 patients with non-complicated
chronic venous insufficiency were treated with oral administration of
Oligomeric Proanthocyanidins (Pycnogenols-OPC) 100 mg/day. To evaluate
the therapeutic efficacy of the treatment, an instrumental evaluation
by optical probe capillaroscope was employed in addition to the
traditional subjective clinical parameters: swelling, itching,
heaviness and pain. The videocapillaroscope examination was performed
at the lower third of the leg and the first toe. Edema in the
capillaroscopic field, the number of observable capillaries and the
capillary dilatation were the parameter chosen to evaluate the efficacy
of treatment. All patients completed the study with no reports of
adverse events during the period of observation.
Results: The results obtained show a positive clinical response (improved or absent
symptoms) in over 80% of patients, with significant improvement of symptoms already
evident after the first 10 days of treatment. The mechanism of action of the OPCs explains
the rapid reduction of the swelling of the lower limbs and correlated with this are the
other evaluable symptoms: heaviness and itching. Particularly striking results were
observed for itching and pain which completely disappeared during the course of therapy in
80% and 53% of the patients respectively. Noteworthy is the good correlation between the
clinical and instrumental data, with improvement in a total of 70% of patients.
Conclusions: The results obtained in the course of this
clinical experience, with evident improvement already during the first
weeks of treatment, the absence of adverse events added to the benefit
of a once-a-day administration, justify the use of OPC in the treatment
of non-complicated chronic venous insufficiency.
Other Common Names: Grape seed extract, Oligomeric Proanthocyanidins (OPCs), Procyanidolic Oligomers (PCOs), Pycnogenol, Procyanidins
During the winter of 1534, the French explorer Jacques Cartier and his crew avoided
scurvy by using Anneda, an Indian medicine probably containing ascorbic acid and
procyanidins. Four centuries later, Szent-Gyorgyi was misguided in proposing citrin [lemon
flavonoid compound] as a second antiscorbutic factor, for flavonoids are devoid of true
vitamin-like behavior. On the other hand, pycnogenols, widely found in old empirical
antiscorbutic remedies, seem more appropriate in this respect, since they are active per
os, bioavailable, linked to various living tissues, and concerned with essential metabolic
pathways. As histidine decarboxylase inhibitors, pycnogenols lower the histamine level in
the aortic endothelium and are believed to protect it against the vascular permeability
alterations occurring early in the atherogenic process.
In 1947, a student at the biological and medical faculty of the University of Bordeaux,
France named Jack Masquelier was assigned the task of determining whether or not the red
inner skin of peanuts was toxic. For his doctoral dissertation, Masquelier undertook a
series of experiments to answer this question. Fairly early in his investigations,
Masquelier was able to determine that in fact peanut skins were not toxic. In the course
of his research, however, he came upon a colorless substance in peanut skin which called
for further examination. By 1948, he had succeeded in isolating that substance, OPC, from
peanut skin, and had identified that it possessed vasoprotective (protective of blood
vessels) potential. After casting about among many possible sources, he found what he was
searching for in the bark of Landes pine trees, a waste product of the lumber industry
typically used as a mulch for gardens. This new source yielded sufficient quantifies of
OPC to be useful for manufacturing purposes.
Subsequent studies by Masquelier eventually revealed another source of OPC besides the
bark of the Landes pine. Grape seeds, which are the waste product of the winemaking
industry and are used to make grape seed oil for cooking, were found to contain even
greater amounts of the same beneficial antioxidant. Though grape seeds did not supplant
pine bark completely, they came to be the primary source of OPC for extraction. Today in
France, Flavan, from Landes pine bark, and Resivit from grape seeds, are both registered
OFC medicines for vascular protection.
Mainstream medical science now regards oxidation as a primary cause of degeneration and
ageing. Oxidation, the slow deterioration of matter as a result of chemical reactions
involving oxygen, is a familiar phenomenon found throughout nature. The rusting of metals,
the spoilage of foods, the rancidification of oils and the crumbling of rubber are
examples of the common process of oxidation. In the body oxidative reactions of many kinds
occur due to exposure to environmental toxins. In the air we breathe and the water we
drink, we are exposed to as many as 60,000 chemical toxins of different kinds, including
cigarette smoke, car exhaust vapors from cleaning fluids and solvents. Some chemical
agents, such as the trihalomethanes, are toxic in quantities almost too small to be
detected. In addition, we are subjected to a variety of chemical food additives such as
preservatives, artificial colors, flavors emulsifiers, lubricants, bleaching agents,
flavor enhancers and synthetic sweeteners. Many of these agents con
tribute to oxidative reactions in the body.
Fortunately, there are nutritional agents that help to prevent against oxidative damage
in the body and fight free radicals, and further help to repair damage that has already
occurred. Antioxidant dietary factors include nutrients such as tocopherol (vitamin E) and
ascorbate (vitamin C), as well as numerous carotenoids and a number of phenols and
flavonoids found in common foods. Dietary fruits and vegetables are the primary sources of
antioxidant dietary factors, though some antioxidants occur in grains, beans, meats,
seafood's and dairy products. But while antioxidants are available in a healthy diet it is
difficult to get enough of them to fend off the damage caused by free radicals resulting
from air and water pollution and other environmental factors.
In terms of protective value, Dr Masquelier's OPC is a superior antioxidant. OPC is
very rapidly absorbed, and is quickly distributed throughout the body as a free radical
fighter, OPC comes to the aid of the body more quickly than other antioxidants, thereby
reducing the potential for free radical damage and the ravages of aging. OPC also
possesses more reactive sites for neutralising free radicals than other known
antioxidants. Furthermore, OPC possesses nucleophilic as well as electrophilic reactive
centers, permitting reactivity with both positively charged and negatively charged free
radical species. what this means is that OPC can "scavenge" or "quench" (neutralize) a
broad variety of types of free radicals.
Considerable recent research has explored therapeutic applications of oligomeric
proanthocyanidin complexes (OPCs), naturally occurring plant metabolites widely available
in fruits, vegetables, nuts, seeds, flowers, and bark. OPCs are primarily known for their
antioxidant activity. However, these compounds have also been reported to demonstrate
antibacterial, antiviral, anticarcinogenic, anti-inflammatory, anti-allergic, and
vasodilatory actions. In addition, they have been found to inhibit lipid peroxidation,
platelet aggregation, capillary permeability and fragility, and to affect enzyme systems
including phospholipase A2, cyclooxygenase, and lipoxygenase. Based on these reported
findings, OPCs may be a useful component in the treatment of a number of conditions
including venous insufficiency, varicose veins, capillary fragility and diabetic
retinopathy. Experimental studies suggest potential benefit in arteriosclerosis, heart
disease and stroke.
Proanthocyanidins (Procyanidins) is an important therapeutic class of flavonoids
extracted from grape seeds and maritime (Landes) pine. When individual molecules bind
together, the result is collectively called procyanidolic oligomers (PCO). They have a
broad range of pharmacologic activity through increasing vitamin C levels, decreasing
capillary permeability and fragility, scavenging free radicals and inhibiting destruction
of collagen. The latter occurs through ability to cross-link collagen fibers, preventing
free-radical damage, inhibiting enzymatic cleavage of collagen, and preventing the
synthesis and release of inflammatory mediators. PCO has approximately 50 times the
anti-oxidant activity of vitamin C or vitamin E. These influences, along with other
mechanisms, explain their benefit in venous and capillary disorders, including venous
insufficiency, capillary fragility, diabetic retinopathy and macular degeneration.
Studies show that PCO also lowers cholesterol levels and can shrink arterial choles
terol deposits.
Grape seed proanthocyanidins are natural antioxidants which possess a broad spectrum of
chemoprotective properties against free radicals and oxidative stress.
There is increasing evidence to indicate cardioprotective effects of red wine
consumption. Such cardioprotective properties of wine have been attributed to certain
polyphenolic constituents of grapes. The purpose of this investigation was to examine
whether proanthocyanidins derived from grape seeds possess cardioprotective properties.
The results of our study demonstrated that proanthocyanidin-fed animals were resistant to
myocardial ischemia reperfusion injury as evidenced by improved recovery of post-ischemic
contractile functions. The proanthocyanidin-fed group revealed reduced extent of
myocardial infarction compared to the control group. Fluorimetric study demonstrated the
antioxidant property of proanthocyanidin as judged by its ability to directly scavenge
peroxyl radicals. Taken together, the results of this study showed that grape
seed-proanthocyanidins possess a cardioprotective effect against ischemia reperfusion
injury. Such cardioprotective property, at least in part, may be attributed to its
ability to directly scavenge peroxyl and hydroxyl radicals and to reduce oxidative stress
developed during ischemia and reperfusion.
Reactivities of several proanthocyanidins (monomers of condensed
tannins) and gallate esters (representing hydrolyzable tannins) with
hydroxyl radicals, azide radicals, and superoxide anions were
investigated using pulse radiolysis combined with kinetic spectroscopy.
We determined the scavenging rate constants and the decay kinetics of
the aroxyl radicals both at the wavelength of the semiquinone
absorption (275 nm) and the absorption band of the gallate ester ketyl
radical (400-420 nm). For most compounds second-order decay kinetics
were observed, which reflect disproportionation of the semiquinones. In
the case of the oligomeric hydrolysable tannins, pentagalloyl glucose
and tannic acid, the decay kinetics were more complex involving
sequential first-order and second-order reactions, which could only be
resolved by kinetic modeling. A correlation of the reaction rates with
hydroxyl radicals (k*OH) with the number of adjacent aromatic hydroxyl
groups (i.e., representing catechol and/or pyrogallol structures) was
obtained for both condensed and hydrolyzable tannins. Similar
correlation for the reactions with azide radicals and superoxide anions
are less obvious, but exist as well. We consider proanthocyanidins
superior radical scavenging agents as compared with the monomeric
flavonols and flavones and propose that these substances rather than
the flavonoids proper represent the antioxidative principle in red wine
and green tea.
The pharmacological treatment of non-complicated chronic venous insufficiency is a
current and well-debated topic. The introduction of new products with action on the venous
system, improved knowledge on the physiopathology of venous insufficiency and the
possibility provided by new analytical instruments, have given new impulse to the
consolidation of the clinical value of phlebotonics in this indication.
Methods: In light of this, 24 patients with non-complicated
chronic venous insufficiency were treated with oral administration of
Oligomeric Proanthocyanidins (Pycnogenols-OPC) 100 mg/day. To evaluate
the therapeutic efficacy of the treatment, an instrumental evaluation
by optical probe capillaroscope was employed in addition to the
traditional subjective clinical parameters: swelling, itching,
heaviness and pain. The videocapillaroscope examination was performed
at the lower third of the leg and the first toe. Edema in the
capillaroscopic field, the number of observable capillaries and the
capillary dilatation were the parameter chosen to evaluate the efficacy
of treatment. All patients completed the study with no reports of
adverse events during the period of observation.
Results: The results obtained show a positive clinical response (improved or absent
symptoms) in over 80% of patients, with significant improvement of symptoms already
evident after the first 10 days of treatment. The mechanism of action of the OPCs explains
the rapid reduction of the swelling of the lower limbs and correlated with this are the
other evaluable symptoms: heaviness and itching. Particularly striking results were
observed for itching and pain which completely disappeared during the course of therapy in
80% and 53% of the patients respectively. Noteworthy is the good correlation between the
clinical and instrumental data, with improvement in a total of 70% of patients.
Conclusions: The results obtained in the course of this
clinical experience, with evident improvement already during the first
weeks of treatment, the absence of adverse events added to the benefit
of a once-a-day administration, justify the use of OPC in the treatment
of non-complicated chronic venous insufficiency.
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1973 - Lagrue G, Oliver-Martin F, and Grillot A, A study of
the effects of procyanidol oligomers on capillary resistance in
hypertension and in certain nephropathies. Sem Hosp Paris 57,
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Das DK. Cardioprotective effects of grape seed proanthocyanidin against
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W, Michel C. Antioxidant capacity of flavanols and gallate esters:
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A, De Bernardi T, Gotti A. Clinical and capillaroscopic evaluation of
chronic uncomplicated venous insufficiency with procyanidins extracted
from vitis vinifera. Minerva Cardioangiol 1999 Jan-Feb;47(1-2):39-46
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