Procyanidins are members of the

proanthocyanidin Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex ...

(or

condensed tannin Condensed tannins (proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, non-hydrolyzable tannins or flavolans) are polymers formed by the condensation of flavans. They do not contain sugar residues. They ...

s) class of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

s. They are oligomeric compounds, formed from

catechin Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic ...

and

epicatechin Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from '' catechu'', which is the tann ...

molecules. They yield

cyanidin Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (glycoside version called anthocyanin#Structure, anthocyanins). It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherr ...

when depolymerized under oxidative conditions. See the box below entitled "Types of procyanidins" for links to articles on the various types.

Distribution in plants

Procyanidins, including the lesser bioactive / bioavailable polymers (4 or more catechines), represent a group of condensed flavan-3-ols that can be found in many plants, most notably

apple An apple is a round, edible fruit produced by an apple tree (''Malus'' spp.). Fruit trees of the orchard or domestic apple (''Malus domestica''), the most widely grown in the genus, are agriculture, cultivated worldwide. The tree originated ...

maritime pine ''Pinus pinaster'', the maritime pine or cluster pine, is a pine native to the south Atlantic Europe region and parts of the western Mediterranean. It is a hard, fast growing pine bearing small seeds with large wings. Description ''Pinus pinast ...

bark,

cinnamon Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, b ...

aronia ''Aronia'' is a genus of deciduous shrubs, the chokeberries, in the family Rosaceae native to eastern North America and most commonly found in wet woods and swamps. The genus Aronia is considered to have 3 species. The most common and wide ...

fruit,

cocoa bean The cocoa bean, also known as cocoa () or cacao (), is the dried and fully fermented seed of ''Theobroma cacao'', the cacao tree, from which cocoa solids (a mixture of nonfat substances) and cocoa butter (the fat) can be extracted. Cacao tree ...

grape seed A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began approximately 8,00 ...

, grape skin, and

red wine Red wine is a type of wine made from dark-colored grape varieties - (red grapes.) The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wines and brown for older red wines. The juice fro ...

s of ''

Vitis vinifera ''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean Basin, Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern ...

'' (the common grape). However,

bilberry Bilberries () are Eurasian low-growing shrubs in the genus ''Vaccinium'' in the flowering plant family Ericaceae that bear edible, dark blue berries. They resemble but are distinct from North American blueberries. The species most often referre ...

cranberry Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus ''Oxycoccus'' of the genus ''Vaccinium''. Cranberries are low, creeping shrubs or vines up to long and in height; they have slender stems that are not th ...

black currant The blackcurrant (''Ribes nigrum''), also known as black currant or cassis, is a deciduous shrub in the family Grossulariaceae grown for its edible berries. It is native to temperate parts of central and northern Europe and northern Asia, w ...

green tea Green tea is a type of tea made from the leaves and buds of the '' Camellia sinensis'' that have not undergone the withering and oxidation process that creates oolong teas and black teas. Green tea originated in China in the late 1st millenn ...

black tea Black tea (also literally translated as red tea from various East Asian languages) is a type of tea that is more tea processing, oxidized than oolong, yellow tea, yellow, white tea, white, and green tea, green teas. Black tea is generally st ...

, and other plants also contain these flavonoids.USDA, August 2004
USDA Database for the Proanthocyanidin Content of Selected Foods
PDF summary accessed from main USDA pag

Page accessed July 31, 2015 Procyanidins can also be isolated from ''

Quercus petraea ''Quercus petraea'', commonly known as the sessile oak, Welsh oak, Cornish oak, Irish oak or durmast oak, is a species of oak tree native to most of Europe and into Anatolia and Iran. The sessile oak is the national tree of Ireland, and an un ...

'' and '' Q. robur'' heartwood (wine barrel oaks).

Açaí oil Açaí oil is obtained from the fruit of ''Euterpe oleracea'' (açaí palm), which grows in the Amazon rainforest. The oil is rich in phenolic compounds similar in profile to the pulp itself, such as vanillic acid, syringic acid, p-hydroxybenzoic ...

, obtained from the fruit of the

açaí palm The açaí palm (, , from Nheengatu ''asai''), '' Euterpe oleracea'', is a species of palm tree (Arecaceae) cultivated for its fruit (açaí berries, or simply açaí), hearts of palm (a vegetable), leaves, and trunk wood. Global demand for th ...

(''Euterpe oleracea''), is rich in numerous procyanidin

oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...

s. Apples contain on average per serving about eight times the amount of procyanidin found in wine, with some of the highest amounts found in the

Red Delicious Red Delicious is a variety of apple with a red exterior and sweet taste. Known as "the Reds" in the industry, this variety is the result of a chance seedling. It was first recognized in Madison County, Iowa, in 1872. Despite its name, it is not r ...

and

Granny Smith The Granny Smith is an List of apple cultivars, apple cultivar that originated in Australia in 1868. It is named after Maria Ann Smith, who Fruit tree propagation, propagated the cultivar from a chance seedling. The tree is thought to be a Hybri ...

varieties. The seed testas of field beans (''

Vicia faba ''Vicia faba'', commonly known as the broad bean, fava bean, or faba bean, is a species of vetch, a flowering plant in the pea and bean family Fabaceae. It is widely cultivated as a crop for human consumption, and also as a cover crop. Vari ...

'') contain procyanidins that affect the

digestibility Digestion is the breakdown of large insoluble food compounds into small water-soluble components so that they can be absorbed into the blood plasma. In certain organisms, these smaller substances are absorbed through the small intestine into th ...

in piglets and could have an inhibitory activity on

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

s. ''

Cistus salviifolius ''Cistus salviifolius'', common names sage-leaved rock-rose, salvia cistus or Gallipoli rose, is a shrub of the family Cistaceae. Etymology The genus name ''Cistus'' derives from the Ancient Greek words ''κίσθος'' (''kisthos'') meaning bas ...

'' also contains oligomeric procyanidins.

Analysis

Condensed tannin Condensed tannins (proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, non-hydrolyzable tannins or flavolans) are polymers formed by the condensation of flavans. They do not contain sugar residues. They ...

s can be characterised by a number of techniques including depolymerisation, asymmetric flow field flow fractionation or small-angle

X-ray scattering X-ray scattering techniques are a family of analytical techniques which reveal information about the crystal structure, chemical composition, and physical properties of materials and thin films. These techniques are based on observing the scatte ...

. DMACA is a dye used for localization of procyanidin compounds in plant histology. The use of the reagent results in blue staining. It can also be used to titrate procyanidins. Total phenols (or antioxidant effect) can be measured using the Folin-Ciocalteu reaction. Results are typically expressed as

gallic acid Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plant ...

equivalents (GAE). Procyanidins from field beans (''

'') or

barley Barley (), a member of the grass family, is a major cereal grain grown in temperate climates globally. It was one of the first cultivated grains; it was domesticated in the Fertile Crescent around 9000 BC, giving it nonshattering spikele ...

have been estimated using the vanillin-HCl method, resulting in a red color of the test in the presence of catechin or proanthocyanidins. Procyanidins can be titrated using the ''Procyanidolic Index'' (also called the '' Bates-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 PCOs content is. However, 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% PCO by some and began appearing on the labels of finished products. All current methods of analysis suggest that the actual PCO content of these products is much lower than 95%. An improved colorimetric test, called the ''Porter Assay'' or ''butanol-HCl-iron method'', is the most common PCO assay currently in use. 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 a spectrophotometer. 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.

Gel permeation chromatography Gel permeation chromatography (GPC) is a type of size-exclusion chromatography (SEC), that separates high molecular weight or colloidal analytes on the basis of size or diameter, typically in organic solvents. The technique is often used for the an ...

(GPC) analysis allows to separate monomers from larger PCO molecules. Monomers of procyanidins can be characterized by

HPLC High-performance liquid chromatography (HPLC), formerly referred to as high-pressure liquid chromatography, is a technique in analytical chemistry used to separate, identify, and quantify specific components in mixtures. The mixtures can origina ...

analysis.

s can undergo acid-catalyzed cleavage in the presence of a

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

phloroglucinol Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the organic synthesis, synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isom ...

(reaction called phloroglucinolysis),

thioglycolic acid Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. TGA is ...

(thioglycolysis),

benzyl mercaptan Benzyl mercaptan is an organosulfur compound with the formula C6H5CH2SH. It is a common laboratory alkylthiol that occurs in trace amounts naturally. It is a colorless, malodorous liquid. Preparation and occurrence Benzyl mercaptan can be prepare ...

cysteamine Cysteamine is an organosulfur compound with the formula . A white, water-soluble solid, it contains both an amine and a thiol functional group. It is often used as the salt of the ammonium derivative SCH2CH2NH3sup>+, including the hydrochlo ...

(processes called

thiolysis Thiolysis is a reaction with a thiol (R-SH) that cleaves one compound into two. Thiolysis involves the addition of coenzyme A to one of the products. This reaction is similar to hydrolysis, which involves water instead of a thiol. This reaction is s ...

) leading to the formation of oligomers that can be further analyzed. Phloroglucinolysis can be used for instance for procyanidins characterisation in wine or in the grape seed and skin tissues. Thioglycolysis can be used to study procyanidins or the oxidation of condensed tannins. It is also used for

lignin Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidit ...

quantitation In mathematics and empirical science, quantification (or quantitation) is the act of counting and measuring that maps human sense observations and experiences into quantities. Quantification in this sense is fundamental to the scientific method. ...

. Reaction on condensed tannins from

Douglas fir The Douglas fir (''Pseudotsuga menziesii'') is an evergreen conifer species in the pine family, Pinaceae. It is the tallest tree in the Pinaceae family. It is native to western North America and is also known as Douglas-fir, Douglas spruce, Or ...

bark produces

and

thioglycolate Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. TGA is ...

s.Douglas-Fir Bark: Characterization of a Condensed Tannin Extract, by Hong-Keun Song, A thesis submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science, December 13, 1984
/ref> Condensed tannins from ''

Lithocarpus glaber ''Lithocarpus glaber'', the Japanese oak, is a tree species in the genus ''Lithocarpus'' found in Japan, China and Taiwan. Mitami Shrine, a Shinto shrine in Sakai, Osaka Prefecture, Japan, is famous locally for its comparatively large populatio ...

'' leaves have been analysed through acid-catalyzed degradation in the presence of

Research

Procyanidin content in

dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

s has not been well documented. Pycnogenol is a dietary supplement derived from

extract An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered. The aromatic principles of ma ...

s from

bark that contains 70% procyanidins, and is marketed with claims it can treat many conditions. The medical evidence is insufficient to support its use for the treatment of seven different chronic disorders.

References

External links

"Pycnogenol: MedlinePlus Supplements"
{{Procyanidin Food chemistry Flavonoid antioxidants de:Oligomere Proanthocyanidine nl:Proanthocyanidine zh:原花色素

Distribution in plants

Analysis

Research

See also

References

External links