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Proanthocyanidin

From Wikipedia, the free encyclopedia

This article needs attention from an expert on the subject. See thetalk pagefor

details.WikiProject Natural phenols and polyphenolsmay be able to help recruit anexpert. (May 2011)

Epicatechin(EC), one of the building blocks ofproanthocyanidins

Proanthocyanidins, also known as OPCs (oligomeric proanthocyanidins) or condensedtannins, are a subgroup of theflavonoidclass ofpolyphenols. In essence, they areoligomer

chains offlavanols, such as theflavan-3-olepicatechin.[citation needed]

They were discovered in 1948 byJacques Masquelier, who developed and later patented

techniques for the extraction of proanthocyanidins from pine needles and grape seeds.[citation

needed]

Contents[hide]

1 Structure of proanthocyanidins 2 Distribution in plants 3 Analysis 4 Uses 5 Oligomeric proanthocyanidins

o 5.1 Biological signifianceo 5.2 Health benefitso 5.3 Oxidative depolymerisationo 5.4 Non oxidative chemical depolymerisationo 5.5 Grape seed oil controversy

6 See also 7 References 8 Further reading 9 External links

[edit] Structure of proanthocyanidins

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i/Proanthocyanidinhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Jacques_Masquelierhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Flavan-3-olhttp://en.wikipedia.org/wiki/Flavanolhttp://en.wikipedia.org/wiki/Oligomerhttp://en.wikipedia.org/wiki/Polyphenolshttp://en.wikipedia.org/wiki/Flavonoidhttp://en.wikipedia.org/wiki/Epicatechinhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Natural_phenols_and_polyphenolshttp://en.wikipedia.org/wiki/Talk:Proanthocyanidin

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[edit] Distribution in plants

Proanthocyanidins represent a group of condensed flavan-3-ols, such as procyanidins,

prodelphinidins and propelargonidins, that can be found in many plants, most notablyapples,

maritime pinebark, cinnamon,aroniafruit,cocoa beans, grape seed, grape skin (procyanidins

andprodelphinidins),[1]andred winesofVitis vinifera(the common grape). However,

bilberry,cranberry,black currant,green tea,black tea, and other plants also contain these

flavonoids. Cocoa beans contain the highest concentrations.[2]

Proanthocyanidins can also be

isolated fromQuercus petraeaandQ. roburheartwood (wine barreloaks).[3]

Aa oil,

obtained from the fruit of the aa palm (Euterpe oleracea), is rich in numerous procyanidin

oligomers.[4]

Apples contain on average per serving about eight times the amount of proanthocyanidin

found in wine, with some of the highest amounts found in theRed DeliciousandGranny

Smithvarieties.[5]

A patented extract ofmaritime pinebark called Pycnogenol bears 65-75 percent

proanthocyanidins (procyanidins).[6]

Thus a 100 mg serving would contain 65 to 75 mg of

proanthocyanidins (procyanidins).

Proanthocyanidinglycosidescan be isolated fromcocoa liquor.[7]

The seedtestasof field beans (Vicia faba) contain proanthocyanidins[8]

that affect the

digestibilityinpiglets[9]

and could have an inhibitory activity on enzymes.[10]

[edit] Analysis

Condensed tannins can be characterised by a number of techniques including

depolymerisation, asymmetric flow field flow fractionation or small-angle X-ray

scattering.[4]

DMACAis a dye that is particularly useful for localization of proanthocyanidin compounds

in plant histology. The use of the reagent results in blue staining.[11]

It can also be used to

titrate proanthocyanidins.

Total phenols (or antioxidant effect) can be measured using theFolin-Ciocalteu reaction.

Results are typically expressed as gallic acid equivalents (GAE).

Proanthocyanidins from field beans (Vicia faba)[12]

orbarley[13]

have been estimated using the

vanillin-HCl method, resulting in a red color of the test in the presence of catechin or

proanthcyanidins.

Proanthocyanidins can be titrated using the Procyanidolic Index (also called theBates-Smith

Assay). It is a testing method that measures the change in color when the product is mixed

with certain chemicals. The greater the color changes, the higher the OPCs content is. It must

be noted, however, that the Procyanidolic Index is a relative value that can measure well over

100. Unfortunately, a Procyanidolic Index of 95 was erroneously taken to mean 95% OPC by

some and began appearing on the labels of finished products. All current methods of analysissuggest that the actual OPC content of these products is much lower than 95%.

[14]

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ia.org/wiki/Proanthocyanidin#cite_note-10http://en.wikipedia.org/wiki/Folin-Ciocalteu_reagenthttp://en.wikipedia.org/wiki/Folin-Ciocalteu_reagenthttp://en.wikipedia.org/wiki/Folin-Ciocalteu_reagenthttp://en.wikipedia.org/wiki/Vicia_fabahttp://en.wikipedia.org/wiki/Vicia_fabahttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-11http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-11http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-11http://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Edgar_Charles_Bate-Smithhttp://en.wikipedia.org/wiki/Edgar_Charles_Bate-Smithhttp://en.wikipedia.org/wiki/Edgar_Charles_Bate-Smithhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-13http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-13http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-13http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-13http://en.wikipedia.org/wiki/Edgar_Charles_Bate-Smithhttp://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Barleyhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-11http://en.wikipedia.org/wiki/Vicia_fabahttp://en.wikipedia.org/wiki/Folin-Ciocalteu_reagenthttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-10http://en.wikipedia.org/wiki/DMACA_reagenthttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=3http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-9http://en.wikipedia.org/wiki/Piglet_%28animal%29http://en.wikipedia.org/wiki/Piglet_%28animal%29http://en.wikipedia.org/wiki/Digestibilityhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-7http://en.wikipedia.org/wiki/Vicia_fabahttp://en.wikipedia.org/wiki/Testa_%28botany%29http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-6http://en.wikipedia.org/wiki/Cocoa_liquorhttp://en.wikipedia.org/wiki/Glycosidehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline-5http://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-4http://en.wikipedia.org/wiki/Granny_Smithhttp://en.wikipedia.org/wiki/Granny_Smithhttp://en.wikipedia.org/wiki/Red_Delicioushttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-3http://en.wikipedia.org/wiki/A%C3%A7a%C3%AD_oilhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-2http://en.wikipedia.org/wiki/Oak_%28wine%29http://en.wikipedia.org/wiki/Quercus_roburhttp://en.wikipedia.org/wiki/Quercus_petraeahttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Black_teahttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Black_curranthttp://en.wikipedia.org/wiki/Cranberryhttp://en.wikipedia.org/wiki/Bilberryhttp://en.wikipedia.org/wiki/Vitis_viniferahttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-0http://en.wikipedia.org/wiki/Prodelphinidinhttp://en.wikipedia.org/wiki/Cocoa_beanhttp://en.wikipedia.org/wiki/Aroniahttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Applehttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=2

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An improved colorimetric test, called the Porter Assay or butanol-HCl-iron method, is the

most common OPC assay currently in use.[15]

The unit of measurement of the Porter Assay is

the PVU (Porter Value Unit). The Porter Assay is a chemical test to help determine the

potency of procyanidin containing compounds, such as grape seed extract. It is an acid

hydrolysis, which splits larger chain units (dimers and trimers) into single unit monomers and

oxidizes them. This leads to a colour change, which can be measured using aspectrophotometer. The greater the absorbance at a certain wavelength of light, the greater

the potency. Ranges for grape seed extract are from 25 PVU for low grade material to over

300 for premium grape seed extracts.[16]

Gel permeation chromatography(GPC) analysis allows to separate monomers from larger

OPC molecules.

Monomers of proanthocyanidins can be characterized byHPLCanalysis.Condensed tannins

can undergo acid-catalyzed cleavage in the presence of anucleophilelikephloroglucinol

(reaction called phloroglucinolysis),thioglycolic acid(thioglycolysis),benzyl mercaptanor

cysteamine(processes calledthiolysis[17]) leading to the formation of oligomers that can befurther analyzed.

[18]

[edit] Uses

This information attracted the attention of public news media, describing that red wine

consumption is associated with favorable intake of health-promoting flavonoids that correlate

positively withoxygen radical absorbance capacity(ORAC).

In red wines, total oligomeric proanthocyanidin content, includingflavan-3-ols(catechins),

was substantially higher (177.18 96.06 mg/L) than that in white wines (8.75 4.53 mg/L).A relative high correlation in red wines was found between ORAC values andmalvidin

compounds (r = 0.75, P < 0.10), and proanthocyanidins (r = 0.87, P < 0.05).[19]

In white wines, a significant correlation was found between the trimeric proanthocyanidin

fraction and peroxyl radical scavenging values (r = 0.86, P < 0.10).

A moderate drink (1 drink per day, about 140 mL) of red wine, or white wine, or wine made

from highbushblueberrycorresponded to an intake of 2.04 0.81 mmol of TE (Trolox

equivalents), 0.47 0.15 mmol of TE, and 2.42 0.88 mmol of TE of ORAC/day,

respectively.[19][20]

Proanthocyanidins are the principal vasoactive polyphenols in red wine that are linked to a

reduced risk of coronary heart disease and to lower overall mortality.[21]

Proanthocyanidins

are present at higher concentrations in wines from areas of southwestern France and Sardinia,

which are associated with increased longevity in the population. Earlier studies that attributed

this health benefit toresveratrolwere premature because of the negligible amount of

resveratrol in red wine.

Proanthocyanidins suppress production of a proteinendothelin-1that constricts blood

vessels.[21]

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These studies provide data supporting theFrench Paradoxthat hypothesizes that intake of

proanthocyanidins and other flavonoids from regular consumption of red wines prevents

occurrence of a higher disease rate (cardiovascular diseases,diabetes) in French citizens on

high-fat diets.[21]

Proanthocyanidins have antioxidant activity and they play a role in the stabilization ofcollagen and maintenance of elastintwo critical proteins in connective tissue that support

organs, joints, blood vessels, and muscle. Possibly because of their effects on blood vessels,

proanthocyanidins have been reported in double-blind research to reduce the duration of

edema after face-lift surgery from 15.9 to 11.5 days.[citation needed]

In preliminary research,

proanthocyanidins were reported to have anti-mutagenicactivity (i.e., to prevent

chromosomal mutations).[citation needed]

Common antioxidants currently used arevitamin Candvitamin E; however, studies show

that proanthocyanidins antioxidant capabilities are 20 times more powerful than vitamin C

and 50 times more potent thanvitamin E.[22]

Proanthocyanidins found in Frenchmaritime

pinebark and grape seed extract work directly to help strengthen all theblood vesselsandimprove the delivery of oxygen to the cells. Proanthocyanidins also have an affinity for cell

membranes, providing nutritional support to reduce capillary permeability and fragility.[citation

needed]Althoughflavonoidsare widespread in nature, the powerful proanthocyanidin

compound is most abundant and available from the bark of the maritime pine and in grape

seeds, or pips. In addition, the particular proanthocyanidins found in the proprietary extract of

maritime pinebark called Pycnogenol have been shown to optimize the production of nitric

oxide in the artery walls so as to relax them and allow greater blood flow and reduced

pressure.[23]

Additionally, this same preparation, Pycnogenol, has been found to normalize

platelet adhesion (aggregation) so as to facilitate normal blood flow.[24]

[edit] Oligomeric proanthocyanidins

In 1948 Jack Masquelier discovered oligomeric proanthocyanidins (OPCs) in the skin of a

peanutby accident. Oligomeric proanthocyanidins are a class offlavonoidcomplexes. OPCs

are found in most plants and thus are a part of the human diet. Especially the skin, seeds and

seed coverings of plants contain large amounts of oligomeric proanthocyanidins. They can be

found in large quantities in grape seed extract and skin, in red grapes, in the red skins of

peanuts, incoconuts, apples (dimericprocyanidin B2), in cocoa, and in the bark ofPinus

pinaster(formerly known as Pinus maritima). It can also be found insea buckthorn oil.[25]

Oligomeric proanthocyanidins can be obtained by the mean ofVaccinium pahalaein vitrocell culture.

[26]

[edit] Biological signifiance

In nature, it is possible that OPCs serve as aplant defense against herbivory.

[edit] Health benefits

Proanthocyanidins have stronganti-oxidantproperties. Foods rich in proanthocyanidins have

highoxygen radical absorbance capacity, which has been linked to numerous health benefitssuch as weight management, cell health, and cardiovascular health.

[27]Scientists continue to

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adical_absorbance_capacityhttp://en.wikipedia.org/wiki/Oxygen_radical_absorbance_capacityhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-26http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-26http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-26http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-26http://en.wikipedia.org/wiki/Oxygen_radical_absorbance_capacityhttp://en.wikipedia.org/wiki/Anti-oxidanthttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=7http://en.wikipedia.org/wiki/Plant_defense_against_herbivoryhttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=6http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-25http://en.wikipedia.org/wiki/Vaccinium_pahalaehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-24http://en.wikipedia.org/wiki/Sea_buckthorn_oilhttp://en.wikipedia.org/wiki/Pinus_pinasterhttp://en.wikipedia.org/wiki/Pinus_pinasterhttp://en.wikipedia.org/wiki/Procyanidin_B2http://en.wikipedia.org/wiki/Coconuthttp://en.wikipedia.org/wiki/Flavonoidhttp://en.wikipedia.org/wiki/Peanuthttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=5http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Third_Reference-23http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Second_Reference-22http://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Flavonoidshttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Blood_vesselshttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-21http://en.wikipedia.org/wiki/Vitamin_Ehttp://en.wikipedia.org/wiki/Vitamin_Ehttp://en.wikipedia.org/wiki/Vitamin_Chttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Mutagenichttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Corder06-20http://en.wikipedia.org/wiki/Diabeteshttp://en.wikipedia.org/wiki/Cardiovascular_diseaseshttp://en.wikipedia.org/wiki/French_Paradox

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research the relevance of proanthocyanidins' strong anti-oxidant properties in vivo for such

applications as cancer prevention and cardiovascular health.[28]

USDA does maintain a

database of proanthocyanidin content and structure for many foods, butdietary supplements

proanthocyanidin content has not been well documented.[29]

In the human body, they might act asantioxidants(free radicalscavengers).[citation needed]

OPCsmay help protect against the effects of internal and environmental stresses such as cigarette

smoking and pollution, as well as supporting normal body metabolic processes. The effects

may include depressing blood fat, emolliating blood vessels, lowering blood pressure,

preventing blood vessel scleroses, dropping blood viscidity and preventingthrombus

formation.[30]

Additionally, studies have shown that OPCs may preventcardiovascular diseasesby

counteracting the negative effects of highcholesterolon theheartandblood vessels.

A Frenchmaritime pinebark extract of OPCs, Pycnogenol, has been shown to improve

microcirculation, retinal edema and visual acuity in the early stages ofdiabeticretinopathy.

[31]Further study has shown that Pycnogenol maintainsantioxidantand anti-

inflammatory properties, selectively binds to collagen and elastin in the body, and aids in the

production of endothelial[32]

nitric oxide. Pycnogenol has also been shown to help normalize

blood glucose (sugar) levels,[33]

and delay sugar absorption.[34]

OPCs are available from fresh grapes, grape juice, andred wine. Although in milligrams per

ounce red wine may contain more OPCs than red grape juice, red grape juice contains more

OPCs per average serving size. An 8-ounce serving of grape juice averages 124 milligrams

OPCs, whereas a 5-ounce serving of red wine averages 91 milligrams.[2][35]

Many other foods

and beverages also contain high amounts of OPCs, but very few come close to the levels

found in red grape seeds and skins (which readily disperse into grape juice when crushed).[2]

[edit] Oxidative depolymerisation

This section is empty.You can help byadding to it.

[edit] Non oxidative chemical depolymerisation

The condensed tannins can nevertheless undergo acid-catalyzed cleavage in the presence of

(an excess of) anucleophile

[36]

likephloroglucinol(reaction called phloroglucinolysis),benzyl mercaptan(reaction calledthiolysis),thioglycolic acid(reaction called thioglycolysis)

orcysteamine. These techniques are generally calleddepolymerisationand give informations

such asaverage degree of polymerisationor percentage of galloylation. These areSN1

reactions, a type of substitution reaction in organic chemistry, involving acarbocation

intermediate under strongly acidic conditions in polarprotic solventslikemethanol. The

reaction leads to the formation of free and derivated monomers that can be further analyzed.

The free monomers correspond to the terminal units of the condensed tannins chains.

In general, reactions are made inmethanol, especially thiolysis, as benzyl mercaptan has a

low solubility in water. They involve a moderate (50 to 90C) heating for a few minutes.

Epimerisationmay happen.

http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-27http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-27http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-27http://en.wikipedia.org/wiki/Dietary_supplementshttp://en.wikipedia.org/wiki/Dietary_supplementshttp://en.wikipedia.org/wiki/Dietary_supplementshttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-28http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-28http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-28http://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Free_radicalhttp://en.wikipedia.org/wiki/Free_radicalhttp://en.wikipedia.org/wiki/Free_radicalhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Thrombushttp://en.wikipedia.org/wiki/Thrombushttp://en.wikipedia.org/wiki/Thrombushttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-29http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-29http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-29http://en.wikipedia.org/wiki/Cardiovascular_diseasehttp://en.wikipedia.org/wiki/Cardiovascular_diseasehttp://en.wikipedia.org/wiki/Cardiovascular_diseasehttp://en.wikipedia.org/wiki/Cholesterolhttp://en.wikipedia.org/wiki/Cholesterolhttp://en.wikipedia.org/wiki/Cholesterolhttp://en.wikipedia.org/wiki/Hearthttp://en.wikipedia.org/wiki/Hearthttp://en.wikipedia.org/wiki/Hearthttp://en.wikipedia.org/wiki/Blood_vesselhttp://en.wikipedia.org/wiki/Blood_vesselhttp://en.wikipedia.org/wiki/Blood_vesselhttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Diabetic_retinopathyhttp://en.wikipedia.org/wiki/Diabetic_retinopathyhttp://en.wikipedia.org/wiki/Diabetic_retinopathyhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-30http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-30http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-30http://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-WebMD-31http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-WebMD-31http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-WebMD-31http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-American_Diabetes_Association-32http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-American_Diabetes_Association-32http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-American_Diabetes_Association-32http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Fourth_Reference-33http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Fourth_Reference-33http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Fourth_Reference-33http://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=8http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=8http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=8http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=9http://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/wiki/Phloroglucinolhttp://en.wikipedia.org/wiki/Phloroglucinolhttp://en.wikipedia.org/wiki/Phloroglucinolhttp://en.wikipedia.org/wiki/Benzyl_mercaptanhttp://en.wikipedia.org/wiki/Benzyl_mercaptanhttp://en.wikipedia.org/wiki/Thiolysishttp://en.wikipedia.org/wiki/Thiolysishttp://en.wikipedia.org/wiki/Thiolysishttp://en.wikipedia.org/wiki/Thioglycolic_acidhttp://en.wikipedia.org/wiki/Thioglycolic_acidhttp://en.wikipedia.org/wiki/Thioglycolic_acidhttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Depolymerisationhttp://en.wikipedia.org/wiki/Depolymerisationhttp://en.wikipedia.org/wiki/Depolymerisationhttp://en.wikipedia.org/wiki/Average_degree_of_polymerisationhttp://en.wikipedia.org/wiki/Average_degree_of_polymerisationhttp://en.wikipedia.org/wiki/Average_degree_of_polymerisationhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/Carbocationhttp://en.wikipedia.org/wiki/Carbocationhttp://en.wikipedia.org/wiki/Carbocationhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Epimerisationhttp://en.wikipedia.org/wiki/Epimerisationhttp://en.wikipedia.org/wiki/File:Wiki_letter_w.svghttp://en.wikipedia.org/wiki/Epimerisationhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/Protic_solventhttp://en.wikipedia.org/wiki/Carbocationhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/SN1_reactionhttp://en.wikipedia.org/wiki/Average_degree_of_polymerisationhttp://en.wikipedia.org/wiki/Depolymerisationhttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Thioglycolic_acidhttp://en.wikipedia.org/wiki/Thiolysishttp://en.wikipedia.org/wiki/Benzyl_mercaptanhttp://en.wikipedia.org/wiki/Phloroglucinolhttp://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/wiki/Nucleophilehttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=8http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-USDAdb-1http://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Medline_Fourth_Reference-33http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-American_Diabetes_Association-32http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-WebMD-31http://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-30http://en.wikipedia.org/wiki/Diabetic_retinopathyhttp://en.wikipedia.org/wiki/Diabetic_retinopathyhttp://en.wikipedia.org/wiki/Maritime_pinehttp://en.wikipedia.org/wiki/Blood_vesselhttp://en.wikipedia.org/wiki/Hearthttp://en.wikipedia.org/wiki/Cholesterolhttp://en.wikipedia.org/wiki/Cardiovascular_diseasehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-29http://en.wikipedia.org/wiki/Thrombushttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Free_radicalhttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-28http://en.wikipedia.org/wiki/Dietary_supplementshttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-27

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Phloroglucinolysis can be used for instance for proanthocyanidins characterisation in

wine[37]

or in the grape seed and skin tissues.[38]

Thioglycolysis can be used to study proanthocyanidins[39]

or the oxidation of condensed

tannins.[40]

It is also used forligninquantitation.[41]

Reaction on condensed tannins from

Douglas firbark producesepicatechinandcatechinthioglycolates.[42]

Condensed tannins fromLithocarpus glaberleaves have been analysed through acid-

catalyzed degradation in the presence ofcysteamine.[43]

[edit] Grape seed oil controversy

A number ofgrape seed oilvendors have claimed that grape seed oil is high in OPCs.

However, independent studies have indicated that grape seed oil is actually the grape product

with the lowest concentration of OPCs. This is because OPCs arepolar molecules, which

have very low solubility innonpolarsolventssuch as oils.

[edit] See also

A type proanthocyanidin B type proanthocyanidin Tannin Polyphenol Phenolic compounds in wine Polyphenols in wine

[edit] References

1. ^Souquet, J; Cheynier, Vronique; Brossaud, Franck; Moutounet, Michel (1996)."Polymeric proanthocyanidins from grape skins". Phytochemistry43 (2): 509.

doi:10.1016/0031-9422(96)00301-9.

2. ^abcUSDA Database for the Proanthocyanidin Content of Selected Foods2004

[verification needed][page needed]

3. ^Vivas, N; Nonier, M; Pianet, I; Vivasdegaulejac, N; Fouquet, E (2006)."Proanthocyanidins from Quercus petraea and Q. robur heartwood: quantification and

structures". Comptes Rendus Chimie9: 120.doi:10.1016/j.crci.2005.09.001.

4. ^Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemicalcomposition, antioxidant properties, and thermal stability of a phytochemical enrichedoil from Acai (Euterpe oleracea Mart.)".J Agric Food Chem56 (12): 46316.

doi:10.1021/jf800161u.PMID18522407.

5. ^Hammerstone, John F.; Lazarus, Sheryl A.; Schmitz, Harold H. (August 2000)."Procyanidin content and variation in some commonly consumed foods".The Journal

of nutrition130 (8S Suppl): 2086S92S.PMID10917927. "Figure 5"

6. ^Rohdewald, P (2002). "A review of the French maritime pine bark extract(Pycnogenol), a herbal medication with a diverse clinical pharmacology".

International journal of clinical pharmacology and therapeutics40 (4): 15868.

PMID11996210.

7. ^Hatano, T; Miyatake, H; Natsume, M; Osakabe, N; Takizawa, T; Ito, H; Yoshida, T(2002). "Proanthocyanidin glycosides and related polyphenols from cacao liquor and

http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-36http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-36http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-37http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-37http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-37http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-38http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-38http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-38http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Vernhet-39http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Vernhet-39http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Vernhet-39http://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Quantitationhttp://en.wikipedia.org/wiki/Quantitationhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-40http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-40http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-40http://en.wikipedia.org/wiki/Douglas_firhttp://en.wikipedia.org/wiki/Douglas_firhttp://en.wikipedia.org/wiki/Epicatechinhttp://en.wikipedia.org/wiki/Epicatechinhttp://en.wikipedia.org/wiki/Epicatechinhttp://en.wikipedia.org/wiki/Catechinhttp://en.wikipedia.org/wiki/Catechinhttp://en.wikipedia.org/wiki/Thioglycolatehttp://en.wikipedia.org/wiki/Thioglycolatehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Hong-Keun-41http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Hong-Keun-41http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Hong-Keun-41http://en.wikipedia.org/wiki/Lithocarpus_glaberhttp://en.wikipedia.org/wiki/Lithocarpus_glaberhttp://en.wikipedia.org/wiki/Lithocarpus_glaberhttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Liang-42http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Liang-42http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Liang-42http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=10http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=10http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=10http://en.wikipedia.org/wiki/Grape_seed_oilhttp://en.wikipedia.org/wiki/Grape_seed_oilhttp://en.wikipedia.org/wiki/Grape_seed_oilhttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Nonpolarhttp://en.wikipedia.org/wiki/Nonpolarhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=11http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=11http://en.wikipedia.org/wiki/A_type_proanthocyanidinhttp://en.wikipedia.org/wiki/A_type_proanthocyanidinhttp://en.wikipedia.org/wiki/B_type_proanthocyanidinhttp://en.wikipedia.org/wiki/B_type_proanthocyanidinhttp://en.wikipedia.org/wiki/Tanninhttp://en.wikipedia.org/wiki/Tanninhttp://en.wikipedia.org/wiki/Polyphenolhttp://en.wikipedia.org/wiki/Polyphenolhttp://en.wikipedia.org/wiki/Phenolic_compounds_in_winehttp://en.wikipedia.org/wiki/Phenolic_compounds_in_winehttp://en.wikipedia.org/wiki/Polyphenols_in_winehttp://en.wikipedia.org/wiki/Polyphenols_in_winehttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=12http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=12http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-0http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-0http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2F0031-9422%2896%2900301-9http://dx.doi.org/10.1016%2F0031-9422%2896%2900301-9http://dx.doi.org/10.1016%2F0031-9422%2896%2900301-9http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-0http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-0http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-2http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-2http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-2http://www.nal.usda.gov/fnic/foodcomp/Data/PA/PA.htmlhttp://en.wikipedia.org/wiki/Wikipedia:Verifiabilityhttp://en.wikipedia.org/wiki/Wikipedia:Verifiabilityhttp://en.wikipedia.org/wiki/Wikipedia:Verifiabilityhttp://en.wikipedia.org/wiki/Wikipedia:Citing_sourceshttp://en.wikipedia.org/wiki/Wikipedia:Citing_sourceshttp://en.wikipedia.org/wiki/Wikipedia:Citing_sourceshttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-2http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-2http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2Fj.crci.2005.09.001http://dx.doi.org/10.1016%2Fj.crci.2005.09.001http://dx.doi.org/10.1016%2Fj.crci.2005.09.001http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-3http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-3http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1021%2Fjf800161uhttp://dx.doi.org/10.1021%2Fjf800161uhttp://dx.doi.org/10.1021%2Fjf800161uhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/18522407http://www.ncbi.nlm.nih.gov/pubmed/18522407http://www.ncbi.nlm.nih.gov/pubmed/18522407http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-4http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-4http://jn.nutrition.org/cgi/content/full/130/8/2086Shttp://jn.nutrition.org/cgi/content/full/130/8/2086Shttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/10917927http://www.ncbi.nlm.nih.gov/pubmed/10917927http://www.ncbi.nlm.nih.gov/pubmed/10917927http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-Medline_5-0http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-Medline_5-0http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/11996210http://www.ncbi.nlm.nih.gov/pubmed/11996210http://www.ncbi.nlm.nih.gov/pubmed/11996210http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-6http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-6http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-6http://www.ncbi.nlm.nih.gov/pubmed/11996210http://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-Medline_5-0http://www.ncbi.nlm.nih.gov/pubmed/10917927http://en.wikipedia.org/wiki/PubMed_Identifierhttp://jn.nutrition.org/cgi/content/full/130/8/2086Shttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-4http://www.ncbi.nlm.nih.gov/pubmed/18522407http://en.wikipedia.org/wiki/PubMed_Identifierhttp://dx.doi.org/10.1021%2Fjf800161uhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-3http://dx.doi.org/10.1016%2Fj.crci.2005.09.001http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-2http://en.wikipedia.org/wiki/Wikipedia:Citing_sourceshttp://en.wikipedia.org/wiki/Wikipedia:Verifiabilityhttp://www.nal.usda.gov/fnic/foodcomp/Data/PA/PA.htmlhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-2http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-1http://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-USDAdb_1-0http://dx.doi.org/10.1016%2F0031-9422%2896%2900301-9http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_ref-0http://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=12http://en.wikipedia.org/wiki/Polyphenols_in_winehttp://en.wikipedia.org/wiki/Phenolic_compounds_in_winehttp://en.wikipedia.org/wiki/Polyphenolhttp://en.wikipedia.org/wiki/Tanninhttp://en.wikipedia.org/wiki/B_type_proanthocyanidinhttp://en.wikipedia.org/wiki/A_type_proanthocyanidinhttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=11http://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Nonpolarhttp://en.wikipedia.org/wiki/Polar_moleculehttp://en.wikipedia.org/wiki/Grape_seed_oilhttp://en.wikipedia.org/w/index.php?title=Proanthocyanidin&action=edit&section=10http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Liang-42http://en.wikipedia.org/wiki/Cysteaminehttp://en.wikipedia.org/wiki/Lithocarpus_glaberhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Hong-Keun-41http://en.wikipedia.org/wiki/Thioglycolatehttp://en.wikipedia.org/wiki/Catechinhttp://en.wikipedia.org/wiki/Epicatechinhttp://en.wikipedia.org/wiki/Douglas_firhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-40http://en.wikipedia.org/wiki/Quantitationhttp://en.wikipedia.org/wiki/Ligninhttp://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-Vernhet-39http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-38http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-37http://en.wikipedia.org/wiki/Proanthocyanidin#cite_note-36

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Phytochemical Analysis, Volume 15, Issue 2, pages 9599, March/April 2004

doi:10.1002/pca.7319. ^The digestibility in piglets of faba bean (Vicia faba L.) as affected by breeding

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Agricultural and Food Chemistry52 (8): 22926.doi:10.1021/jf035311i.

PMID15080635.19.^abSnchez-Moreno, Concepcin; Cao, Guohua; Ou, Boxin; Prior, Ronald L.(2003). "Anthocyanin and Proanthocyanidin Content in Selected White and Red

Wines. Oxygen Radical Absorbance Capacity Comparison with Nontraditional Wines

Obtained from Highbush Blueberry".Journal of Agricultural and Food Chemistry51

(17): 488996.doi:10.1021/jf030081t.PMID12903941.

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Crozier, A. (2006). "Oenology: Red wine procyanidins and vascular health".Nature

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Augustin Scalbert, Brigitte Pollet, Catherine Lapierre, Catherine L. M. Herv du

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