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09-SEPTEMBER-2008 19:33:10 - Proanthocyanidin Redirected from Proanthocyanidins Epicatechin EC, one of the possible building blocks of proanthocyanidins Epicatechin EC, one of the possible building blocks of proanthocyanidins Proanthocyanidin also known as procyanidin oligomeric proanthocyanidin OPC, pycnogenol, leukocyanidin and leucoanthocyanin is a class of flavanols. Proanthocyanidins are essentially polymer chains of flavonoids such as catechins.1 One was discovered in 1936 by Professor Jacques Masquelier and called Vitamin P, although this name did not gain official category status and has since fallen out of usage. It was Masquelier who first developed techniques for the extraction of proanthocyanidins from certain plant species. Proanthocyanidins have been sold as nutritional and therapeutic supplements in Europe since the 1980s, but their introduction to the United States market has been relatively recent. Contents 1 Distribution in plants 2 Uses 3 Oligomeric proanthocyanidins 4 See also 5 References 6 External links Distribution in plants Proanthocyanidins can be found in many plants, most notably apples, pine bark, cinnamon, grape seed, cocoa, grape skin, and red wines of Vitis vinifera. However, bilberry, cranberry, black currant, green tea, black tea, and other plants also contain these flavonoids. The berries of chokeberry, specifically black chokeberry, have the highest measured concentrations of proanthocyanidin found in any plant to date.23 4 Apples contain on average per serving about eight times the amount of proanthocyanidin found in wine, with highest amounts found in the Red Delicious and Granny Smith varieties. 5 Uses This information attracted the attention of public news media, describing that red wine consumption was associated with favorable intake of health-promoting flavonoids which correlate with oxygen radical absorbance capacity ORAC. In red wines, total oligomeric proanthocyanidin content, including 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 and malvidin compounds r = 0.75, P 0.10, and proanthocyanidins r = 0.87, P 0.05.6 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 highbush blueberry corresponded to an intake of 2.04 +/- 0.81 mmol of TE, 0.47 +/- 0.15 mmol of TE, and 2.42 +/- 0.88 mmol of TE of ORAC/day, respectively. Proanthocyanidins are the principal vasoactive polyphenols in red wine which is linked to a reduced risk of coronary heart disease and to lower overall mortality.7 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 to resveratrol were premature because of the negligible amount of resveratrol in red wine. Proanthocyanidins suppress production of a protein endothelin-1 that constricts blood vessels.8 These studies provide data supporting the French Paradox which 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.9 Proanthocyanidins have antioxidant activity and they play a role in the stabilization of collagen and maintenance of elastin - two 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 15.855468 to 11.486745222 days.citation needed In preliminary research, proanthocyanidins were reported to have anti-mutagenic activity i.e., to prevent chromosomal mutations. Common antioxidants currently used are vitamin C and vitamin E; however, studies show that proanthocyanidins antioxidant capabilities are 20 times more powerful than vitamin C and 50 times more potent than vitamin E 10. Proanthocyanidins found in pine bark and grape seed extract work directly to help strengthen all the blood vessels and improve the delivery of oxygen to the cells. Proanthocyanidins also have an affinity for cell membranes, providing nutritional support to reduce capillary permeability and fragility. Although flavonoids are 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. Proanthocyanidins reduce histamine production, and are used in the treatment of allergies. Proanthocyanidins help improve circulation by strengthening capillary walls. This is especially important for people with compromised circulatory systems, such as stroke victims, diabetics, arthritics, smokers, oral contraceptive users and people with general cardiovascular insufficiencies. Proanthocyanidins inhibit enzymes that break down collagen. Proanthocyanidins help collagen repair. The breakdown of collagen is what causes our skin to lose its elasticity which in turn causes wrinkles. Proanthocyanidins help keep skin elastic, smooth and wrinkle-free. Proanthocyanidins are also taken as an oral cosmetic to help in the prevention of wrinkles. Proanthocyanidins act as an internal sunscreen. Inhibiting the daily effects the Sun's rays have on our skin is our best defense against the aging of our skin. Proanthocyanidins cross the blood-brain barrier to protect the blood vessels in the brain. Proanthocyanidins cross the blood-brain barrier. This enables proanthocyanidins to fight free radicals in the vessels of the brain that in turn will help them remain healthy. This can result in increased mental acuity, a decreased potential for stroke, and possibly in fighting senility. Oligomeric proanthocyanidins Oligomeric proanthocyanidins or OPCs are a class of flavonoid complexes found in sea buckthorn oil11 and grape seeds and skin, that act as antioxidants free radical scavengers in the human body. In 1948 Jack Masquelier discovered oligomeric proanthocyanidins on the skin of a peanut by accident. Oligomeric proantocyanidins are found in most plants and thus are a part of the human diet. Oligomeric proanthocyanidins are found in large quantities in grape seed extract, in red grapes, in the red skins of peanuts, in coconuts, apples, and in the bark of Pinus maritima. Especially the skin, seeds and seed coverings of plants contain large amounts of oligomeric proanthocyanidins. It is possible that they serve as a plant defense. OPCs may 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 preventing thrombus formation 12. Additionally, studies have shown that OPCs may prevent cardiovascular disease by counteracting the negative effects of high cholesterol on the heart and blood vessels. A number of grape seed oil vendors 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 are polar molecules which have very low solubility in nonpolar solvents such as oils. However OPCs are available from fresh grapes, grape juice, and red 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, while a 5 ounce serving of red wine averages 91 milligrams.1314 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.13 See also Polyphenol References ^ PhenolicsInterm. www.herbalchem.net. Retrieved on 2008-03-17. ^ Wu, X., Gu, L., Prior, R. L., McKay, S. 2004. Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia and Sambucus and their antioxidant capacity. J Agric Food Chem. 52 26: 7846-7856. ^ Liwei Gu et al.Concentrations of Proanthocyanidins in Common Foods and Estimations of Normal Consumption. J. Nutr. 134:613-617, March 2004 ^ Gu, L et al. Procyanidin and catechin contents and antioxidant capacity of cocoa and chocolate products. J Agric Food Chem. 2006 May 31;5411:4057-61. ^ Hammerstone J. F. et al http://jn.nutrition.org/cgi/content/full/130/8/2086S Journal of Nutrition. 2000;130:2086S-2092S Figure 5 ^ Sanchez-Moreno, C., G. Cao, B. Ou R.L. Prior 2003. Anthocyanin and proanthocyanidin content in selected white and red wines. Oxygen radical absorbance capacity comparison with nontraditional wines obtained from highbush blueberry. J Agric Food Chem. 2003 Aug 13;5117:4889-96. ^ Corder, R., W. Mullen, N.Q. Khan, S.C. Marks, E. G. Wood, M.J. Carrier A. Crozier 2006. Oenology: Red wine proanthocyanidins and vascular health., Nature vol. 444, p. 566; 30 November 2006. ^ Corder et al. ^ Corder et al. ^ Shi,J. et al.,2003. Polyphenolics in grape seeds-biochemistry and functionality. J Med Food.64:291-9. ^ Rosch D, Mugge C, Fogliano V, Kroh LW 2004-11-03. Antioxidant oligomeric proanthocyanidins from sea buckthorn Hippophae rhamnoides Pomace. Retrieved on 2007-02-08. ^ Murphy, KJ et al.,2003.Dietary flavanols and procyanidin oligomers from cocoa Theobroma cacao inhibit platelet function. American Journal of Clinical Nutrition. 776: 1466-1473 ^ a b USDA Database for the Proanthocyanidin Content of Selected Foods - 2004 http://www.nal.usda.gov/fnic/foodcomp/Data/PA/PA.html ^ Grape Juice Beats Wine in New Antioxidant Tests http://www.medicalnewstoday.com/medicalnews.php?newsid=15553 Prof. Jack Masquelier - A Lifetime Devoted to Science Oligomeric Proanthocyanidins Information Campagna P. Farmaci vegetali. Minerva Medica ed. Torino, 2008 External links Prof. Jack Masquelier - A Lifetime Devoted to Science OPC Antioxidant Reference Guide Analysis of Proanthocyanidins in Grape Seed Extracts, Health Foods and Grape Seed Oils, J.Health Sci., 491, 45-54, 2003 Oligomeric Proanthocyanidin Complexes: History, Structure, and Phytopharmaceutical Applications. Altern Med Rev 2000;52:144-151. USDA Database for the Proanthocyanidin Content of Selected Foods - 2004 Grape seed extract halts cell cycle, checking growth of colorectal tumors in mice v d e Types of Flavonoids Flavones: Apigenin | Luteolin | Tangeritin Synthetics: Diosmin | Flavoxate Isoflavones: Biochanin A | Coumestrol | Daidzein | Daidzin | Formononetin | Genistein | Puerarin Flavonols: Fisetin | Isorhamnetin | Kaempferol | Myricetin | Pachypodol | Quercetin | Rhamnazin Flavanones: Eriodictyol | Hesperetin | Homoeriodictyol | Naringenin 3-Hydroxyflavanones: Dihydrokaempferol | Dihydroquercetin Flavan-3-ols: Catechins | Epicatechins | Epigallocatechin Anthocyanidins: Cyanidin | Delphinidin | Malvidin | Pelargonidin | Peonidin | Petunidin Misc: List of phytochemicals and foods in which they are prominent Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Proanthocyanidin Categories: Flavonoids | Food science | Phenols | Phytochemicals | Dietary antioxidantsHidden categories: All articles with statements | Articles with statements since August 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Nederlands 中文 This page was last modified on 25 August 2008, at 04:2
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