Richard Beliveau, Ph.D. and Denis Gingras, Ph.D. See book keywords and concepts | PROANTHOCYANIDIN CONTENT OF SELECTED FOODS
Food
Proanthocyanidin content (mg/100 g)
Cinnamon
8,108
Cocoa powder
1,373
Red beans
563
Hazelnuts
501
Cranberries
418
Wild blueberries
329
Strawberries
145
Apples (Red Delicious with peel)
128
Grapes
81
Red wine
62
Raspberries
30
Cranberry juice
13
Grapeseed oil
0
Source: USDA Database for the proanthocyanidin Content of Selected Foods
Table 14
As for cancer prevention: studies on the anticancer potential of proanthocyanidins are just beginning, but the results obtained so far are encouraging. | | The other berries discussed in this chapter contain much less, although the proanthocyanidin content of strawberries may be favourably compared to that of other foods rich in these compounds. It is also important to note that cranberry juice has a much lower proanthocyanidin content than does the whole fruit, and can thus not be considered a significant source of these molecules.
The proanthocyanidins are known primarily for their exceptional antioxidant power. | Tori Hudson, N.D. See book keywords and concepts | One of these, proanthocyanidin, has especially good cardiovascular effect. Hawthorn preparations are modestly effective in reducing blood pressure,323 in the prevention and treatment of atherosclerosis, lowering cholesterol, and preventing the oxidation of LDL.324 Hawthorn preparations improve the blood supply to the heart by dilating the coronary arteries, increase the force of contraction of the heart muscle, and regulate cardiac rhythm. | David W. Grotto, RD, LDN See book keywords and concepts | Studies show that the predominant antioxidant, proanthocyanidin, has twenty times greater antioxidant power than vitamin E and fifty times greater than vitamin C. Resveratrol, a key phytonutrient found mainly in the skins of grapes, has anti-inflammatory and anticarcinogenic properties. Grapes are also high in flavonoids. Red grapes contain the carotenoid ly-copene, which may help in fighting breast and prostate cancer.
Home Remedies
The juice of green grapes that is combined with water, alum, and salt has been reported to lessen the scars of acne when applied to the face. | David Hoffman, FNIMH, AHG See book keywords and concepts | When two proanthocyanidin molecules are linked together, the result is called a dimer; a linkage of three forms is a trimer and four a tetramer. Collectively, mixtures of proanthocyanidin dimers, trimers, tetramers, and larger molecules are known as oligomeric procyanidins (OPCs).
Fruit-bearing plants are high in oligomeric procyanidins, and heartwood and bark are rich sources of unusual proanthocyanidins. OPCs, called "pycnogenols" in the commercial supplement market, are available in extracts of grape seeds and the bark of the maritime pine. | | The name proanthocyanidin is used alternatively for condensed tannins because, on treatment with hot acid, some of the carbon-carbon linking bonds are broken, and an-thocyanidin monomers may be formed.
When two proanthocyanidin molecules are linked together, the result is called a dimer; a linkage of three forms is a trimer and four a tetramer. Collectively, mixtures of proanthocyanidin dimers, trimers, tetramers, and larger molecules are known as oligomeric procyanidins (OPCs). | Erich Grotewold See book keywords and concepts | A major recent breakthrough has been the isolation of genes encoding two key enzymes—anthocyanidin reductase (ANR) and leucoanthocyanidin reductase (LAR)—that provide the initiating and extension units for proanthocyanidin biosynthesis (Figure 3.1).
ANR was initially identified through characterization of the banyuls locus in Arabidopsis (Devic et al., 1999). The gene and enzyme now have been studied in detail in both Arabidopsis and Medicago (Xie et al., 2003, 2004a) and the enzyme activity has been described in Camellia sinensis and a number of other plant species (Punyasiri et al. | | Dihydroflavonol Reductase
In contrast to ANR, DFR has long been known to contribute to both anthocyanidin and proanthocyanidin biosynthesis (Heller et al., 1985; Reddy et al, 1987). Recently, Shimada et al. (2004) reported the characterization of DFR enzymes from Spinachia oleracea and Phytolacca americana. As with most other members of the order Caryophyllales, anthocyanins are entirely replaced in these plants by betalain pigments, which are derived from tyrosine via dihydroxyphenylalanine by a pathway unrelated to flavonoid metabolism (Strack et al, 2003). | | Although we have moved much closer to an understanding of this pathway with the cloning and characterization of ANR and LAR, the mechanism by which the extension units are incorporated into proanthocyanidin polymers remains unknown (Dixon et al., 2005). ho oh oh oh anthocyanidin:
2,3-c/s-2r,3r-flavan-3-ol: r1=r2=h, (-)-epiafzelechin
Ri = R2 = H, pelargonidin Rl=OH, R 2=H, cyanidin Ri = R2=OH, delphinidin
Ri=OH, R2=H, (-)-epicatechin Ri=R2=OH, (-)-epigallocatechin
Figure 3.3 Reaction catalyzed by anthocyanidin reductase (ANR) (Xie et al, 2003).
3.2. | | LAR generates (2,3-trans) catechin from leucoanthocyanidin, competing with ANS/LDOX for substrate to produce an alternative initiating unit for proanthocyanidin biosynthesis. Interestingly, LAR does not appear to exist in Arabidopsis, consistent with the presence of only 2,3-cis initiating and extension units in this species (Abrahams et al., 2003; Tanner et al., 2003). | | Another possibility is that the DFR enzymes in these plants have lost the ability to interact with other components of a flavonoid enzyme complex, so that only flavonols are synthesized in tissues where enzymes of the proanthocyanidin pathway, such as ANS/LDOX, ANR, or LAR, are not present. More work is needed on this interesting system to assess the specific role(s) of the DFR enzymes in these species and how the flavonoid and betalain pathways have evolved in the Caryophyllales.
3.3. | David W. Grotto, RD, LDN See book keywords and concepts | They contain a variety of phytochemical antioxidants such as proanthocyanidin, epicatechin, gallic, and p-coumaric acids. One study found persimmons to be higher in soluble and insoluble dietary fibers, total phenols, and many minerals than apples.
Home Remedies
The leaves of the persimmon have been used in Chinese medicine for a variety of conditions: as a poultice for snakebites and skin irritations, as a beverage made from boiled leaves for hypertension, for reducing blood clotting, and to fight cancer.
Throw Me a Lifesaver! | Tori Hudson, N.D. See book keywords and concepts | Mixtures of proanthocyanidin molecules are referred to as procyanidolic oligomers (PCO). These commercially prepared extracts of grape seeds and pine bark, or PCO extracts, possess potent antioxidant activity that is far stronger than even vitamin E or vitamin C. In animal studies, PCO extracts have been shown to prevent damage to the arterial lining, lower blood cholesterol levels, and shrink cholesterol deposits in the arteries. | Richard Beliveau, Ph.D. and Denis Gingras, Ph.D. See book keywords and concepts | It is also important to note that cranberry juice has a much lower proanthocyanidin content than does the whole fruit, and can thus not be considered a significant source of these molecules.
The proanthocyanidins are known primarily for their exceptional antioxidant power. This quality is discernible in the story of the French explorer Jacques Cartier's second voyage to America, during which his crew, forced to winter in what is now Quebec, was stricken with scurvy. | Thomson Healthcare, Inc. See book keywords and concepts | Hepatoprotective Effects: proanthocyanidin has been shown to significantly attenuate acetaminophen-induced hepatic DNA damage, apoptopic and necrotic cell death of liver cells. The component also antagonizes acetaminophen induced changes in bcl-Xl expression (Ray, 1999).
Ischemia Preventive Effects: Maintenance of microvascular injury by procyanidins occurs through the scavenger effect of reactive oxygen species (Maffei Facino, 1994). Procyanidins also reduce ventricular contraction in a dose-dependent fashion. | | Mice fed Grape Seed proanthocyanidin extract (GSPE) had a decrease in 12-O-tetradecanoylphorbol-13-acetate (TPA) induced production of reactive oxygen species, DNA fragmentation in hepatic and brain tissues and lipid peroxidation. GSPE was a better scavenger of free radicals and inhibitor of oxidative tissue damage than yitamin C, vitamin E succinate, or a combination of these vitamins and beta-carotene in the doses studied (Bagchi et al, 1998). | | A novel proanthocyanidin IH636 Grape Seed extract increases in vivo Bcl-XL expression and prevents acetaminophen-induced programmed and unprogrammed cell death in mouse liver. Arch Biochem Biophy s Sep 1;369(1):42-58. 1999.
Robert L; Godeau G; Gavignet-Jeannin C et al. The effect of procyanidolic oligomers on vascular permeability. A study using quantitative morphology. Pathol Biol (Paris) Jun;38(6):608-16. 1990.
Saito M, Hosoyama Ft, Ariga T et al. Antiulcer activity of Grape Seed extract and procyanidins. J Agric Food Chem; 46:1460-1464. 1998.
Sevanian A & Ursini F. | | The cytotoxic effects of a novel Grape Seed proanthocyanidin extract on cultured human cancer cells (abstract 1549). Proc Am Assoc Cancer Res; 39:227. 1998. .
Karim M, Kappagoda T & German B. Endothelium dependent vasorelaxing activity of polymeric phenolics (flavonoids) present in Grape Seed extract (abstract 2218). FASEB J; 12(4):A382. 1998.
Kern W, List PH, Horhammer L (Hrsg.), Hagers Handbuch der Pharmazeutischen Praxis, 4. Aufl., Bde 1-8: Springer Verlag Berlin, Heidelberg, New York, 1969.
Lagrue G, Oliver-Martin F & Grillot A. | Erich Grotewold See book keywords and concepts | Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis, Plant Physiol 130: 561-
576.
Aharoni, A., De Vos, C. PL, Wein, M., Sun, Z, Greco, R., Kroon, A., Mol, J. N., and O'Connell, A. P.,
2001, The strawberry FaMYBl transcription factor suppresses anthocyanin and flavonol accumulation in transgenic tobacco, Plant J'28: 319-332. Alfenito, M. R., Souer, E., Goodman, C. D., Buell, R., Mol, J., Koes, R., and Walbot, V. | Thomson Healthcare, Inc. See book keywords and concepts | Beneficial effects of a novel IH636 Grape Seed proanthocyanidin extract in the treatment of chronic pancreatitis. Digestion; 63(3):203-206. 2001.
Baruch. the effects of Endotelon in postoperative edema. Results of a double-blind study versus placebo in 32 female patients. Ann Chir Plast Estfie?;29(4):393-395. 1984.
Bavaresco L; Fregoni C; Cantu E; Trevisan M. Stilbene compounds: from the grapevine to wine. Drugs Exp Clin Res; 25(2-3):57-63. 1999.
Boissin JP; Corbe C; Siou A. Chorioretinal circulation and dazzling: use of procyanidol oligomers (Endotelon). | Joerg Gruenwald, Ph.D. See book keywords and concepts | Hartisch C et al., proanthocyanidin pattern in Hamamelis virginiana. In: PM 62, Abstracts of the 44th Ann Congress of GA, 119. 1996.
Hartisch C et al., Study on the localisation and composition of the volatile fraction of Hamamelis virginiana. In: PM 62, Abstracts of the 44th Ann Congress of GA, 133. 1996.
Knoch HG, (1991) Hamorrhoiden I. Grades, Wirksamkeit einer Salbe auf pflanzlicher Basis. Munch Med Wschr 31/32: 481-484.
Knoch HG, Klug W, Hiibner WD (1992) Salbenbehandlung von Hamorrhoiden ersten Grades. | C. P. Khare See book keywords and concepts | Active principles and pharmacology
Stem yielded gutta (a linear isomer of natural rubber), dulcitol and proanthocyanidin consisting of a dimer of leucopelargonidin.
Leaves yielded proanthocyanidins and also gutta.
Roots gave proanthocyanidins consisting of monomeric leucopelargonidin, its monomer, dimer and tetramer.
Rootbark contains triterpenoids, mangiferine, phlobatannin, glycosidal tannins and a triterpene ether.
On the experimental level, both infusion and decoction of the rootbark exhibited hypoglycaemic activity. In 1 g/kg p.o. | Thomson Healthcare, Inc. See book keywords and concepts | In one study, the antioxidant effect of proanthocyanidin was more potent compared to vitamin C and vitamin E succinate (Bagchi, 1999,1997). The compound also inhibits peroxidation of phosphatidylcholine liposomes (Plumb, 1998). In one study, Grape Seed extract trapped free radicals and inhibited their production, markedly delayed the onset of lipid peroxidation, and inhibited the damaging effects of the enzymes that can degrade connective tissue structures. | Joseph E. Mario See book keywords and concepts | Counter urinary infections with Proanthocyanidins and Flavonols in Cranberries; neutralize free radicals with Pycnogenol/Pronogenol from Pine bark, or take advantage ofthe more active antioxidant proanthocyanidin B2-3-0 Gallate from Grape seed extract. | The Life Extension Editorial Staff See book keywords and concepts | The bioflavonoids work not only with vitamin C but also on behalf of vitamin C, pteventing the breakdown of ascorbate. The proanthocyanidin bioflavonoids work by binding to collagen, increasing elasticity and flexibility. The proanthocyanidins are considered a powerful antioxidant, defending the collagen matrix against free-radical attack and guarding it against enzymatic breakdown through the enhanced delivery of oxygen and blood to the eye.
Rutin, a bioflavonoid from the citms family, has demonstrated the ability to lower IOP when used in conjunction with standard drugs. | | Today pycnogenols are tecognized by terms such as proanthocyanidins, oligo-meric proanthocyanidin complexes (OPCs), or procy-anidolic oligomers (PCOs). In the United States, Pycnogenol is a registered trademark for Horphag Ltd. of Switzerland, identifying a PCO derived from French maritime pine trees.
Much discussion as to whether pine bark or grape seed extract delivers the most medicinal advantage still leaves the question unresolved. Dr. | Stephen T., M.D. Sinatra See book keywords and concepts | The proanthocyanidins go by popular names such as Pycnoge-nol and OPC (oligomeric proanthocyanidin) which are trademarks. While Pycnogenol was patented by a French researcher in 1987, for centuries Native Americans have used as a remedy a tea made from the bark and needles of certain evergreen trees. Currently, Pycnogenol is often made from the Pinus maritima tree.
Proanthocyanidins such as Pycnogenol contain many bioflavonoids such as catechins and epicatechins, as well as organic acids. | by Michael Murray, N.D. and Joseph Pizzorno, N.D. See book keywords and concepts | | The anthocyanidins and PCOs (short for proanthocyanidin oligomers) are the blue or purple pigments found in grapes, blueberries, and other foods. They can also be extracted from pine bark. These substances increase vitamin C levels within our cells, decrease the leakiness and breakage of small blood vessels, protect against free-radical damage, and help prevent destruction of collagen, an important protein for healthy skin and connective tissue. Extracts of grape seeds and pine bark are popular supplements that provide anthocyanidins and PCOs. | Sheldon Saul Hendler and David Rorvik See book keywords and concepts | In one study, a grape seed proanthocyanidin extract more potently protected brain and hepatic tissues from the damage of experimentally induced reactive oxygen species damage than did other antioxidants (vitamin C, vitamin E succinate and beta-carotene). In other in vitro experiments, grape seed proanthocyanidins have strongly inhibited reactive oxygen species activities implicated in microvascular injury.
Acetaminophen-induced programmed and unprogrammed liver-cell death was dramatically prevented and reduced in mice treated with a grape seed proanthocyanidin extract. | David Hoffman, FNIMH, AHG See book keywords and concepts | Proanthocyanidins may contain 2 to 50 or more flavonoid units; proanthocyanidin polymers have complex structures because the flavonoid units can differ for some substituents and because the sites for interflavan bonds vary.
Interactions with Other Macromolecules
Tannins have a major impact on animal nutrition because of their ability to form complexes with numerous types of molecules. |
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