Procyanidins polyphenolic

Procyanidins (polyphenolic oligomers) Vitis vinifera (Vitaceae) Collagenase (38 pM) [87, 96]... 

Kandhare, A.D., Bodhankar, S.L., Singh, V., Mohan, V., and Thakurdesai P.A. 2013. Antiasthmatic effects of type-A procyanidine polyphenols from cinnamon bark in ovalbumin-induced airway hyperresponsiveness in laboratory animals. Biomedicine Aging Pathology, 3 23-30. 

The effects of catechin, epicatechin, procyanidin B2, caffeic acid, / -coumaric acid, myricetrin, and quercetrin on the color intensity and stability of malvidin 3-glucoside at a molar ratio of 1 1 under conditions similar to red wine were evaluated. " Flavan 3-ols appeared to have the lowest protective effects and flavonols the highest strong color changes were visually perceptible. " In the complexation of malvin chloride and natural polyphenols, flavonol glycosides by far exerted the best protector effect. ... 

Thousands of polyphenols from fruits (grapes, apples, etc.), vegetables (horse beans), and teas have been identified, many having good coloring properties, especially anthocyanins and some flavonoids. Well-documented reviews discuss the coloring capacities of some polyphenols including procyanidins. - Detailed presentations of anthocyanin and flavonoid properties and analysis are included in Sections 2.3, 4.3, and 6.3. The soluble proanthocyanidins of the colored horse bean Viciafaba L. seed coats were isolated and separated by solvent partition. 

Kusuda M, Inada K, Ogawa TO, Yoshida T, Shiota T, Shiota S, Tsuchiya T, Hatano T. (2006) Polyphenolic constituents structures of Zanthoxylum piper-itum fruit and the antibacterial effects of its polymeric procyanidin on methicillin-resistant Staphylococcus aureus. Biosci Biotechnol Biochem 70 1423-1431. 

Shen, Z. et ah, Procyanidins and polyphenols of Larix gmelini bark. Phytochemistry 25, 2629, 1986. 

Glories, Y. et al., Identification et dosage de la procyanidine A2 dans les raisin et les vins de Vitis vinifera L.C. V. merlot noir, cabernet sauvignon et cabernet franc. In Polyphenols Communications 96 (eds J. Vercauteren, C. Cheze, M. Dumon, and J.-F. Weber), Groupe Polyphenols, Bordeaux, 1996, p. 153. 

Hatano and Hemingway used NOE studies to assess the association of catechin and procyanidin B-3 with oligopeptides (see also relevant results in Refs. 253-256). The observed intermolecular NOEs indicating the preferred sites in the association of catechin and procyanidin B-3 with the tetrapeptide Gly-Pro-Gly-Gly are shown in 232 and 233, respectively. The molecular shapes of both the polyphenol and polypeptide are important features as far as selectivity is concerned. 

Tuckmantel, W., Kozikowski, A.P., and Romanczyk, L.J. Jr., Studies in polyphenol chemistry and bioactivity. 1. Preparation of building blocks from (+)-catechin. Procyanidin formation. Synthesis of the cancer cell growth inhibitor, 3-0-galloyl-(2R,3R)-epicatechin-4(3,8-[3,0-galloyl-(2R,3R)-epicatechin], J. Am. Chem. Soc., 121, 12073, 1999. 

Kozikowski, A.P., Tuckmantel, W., and George, C., Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an 0-alkylated derivative of procyanidins B2 to (R)-(—)-2,4-diphenylbutyric acid, J. Org. Chem., 65, 5371, 2000. 

This step is optional, depending on how critical it is to separate anthocyanins from other polyphenolics in subsequent analysis. The ethyl acetate fraction is enriched in polypheno-lics such as flavonols, procyanidins, and cinnamates. If analysis of this fraction is desired, a cleaner isolate will be obtained if residual water is removed by passing a nitrogen gas stream through the cartridge for 2 to 3 min before applying ethyl acetate. 

Figure 11.3.2 HPLC chromatogram of neutral polyphenolics found in Niagara grapes detected at 280 nm. Retention time 8.599 min, procyanidin B3 9.781 min, procyanidin B1 13.409 min, catechin 16.138 min, procyanidin B2 20.781 min, epicatechin 22.281 min, catechin-catechin-gallate 23.925 min, catechin-catechin-gallate isomer 28.955 min, catechin-gallate. AU, absorbance units. Reproduced from Lee and Jaworski (1987) with permission from the American Society for Enology and Viticulture.

Figure 11.3.12 HPLC chromatograms of polyphenolics in Concord grape extract detected at 280 nm. (A) All polyphenolics, including anthocyanins. (B) Nonanthocyanin polyphenolics after fractionation. Peak identification 1, cis-caftaric acid 2, frans-caftaric acid 3, procyanidin B3 4, c/s-coutaric acid 5, frans-coutaric acid 6, epicatechin 7, quercetin galactoside 8, quercetin glucoside. Reproduced from Oszmianski and Lee (1990) with permission from the American Society for Enology and Viticulture.

The determination of polyphenolics may result in interference due to co-elution of phenolic acids and procyanidins. This problem can be eliminated by fractionation of polyphenolics into acidic and neutral polyphenolics prior to sample injection into the HPLC system. Because the fractionation techniques effectively improve the resolution of many polyphenolic peaks in the reversed-phase HPLC system, it is suggested that further characterization and identification of unknown peaks be conducted by additional methods such as mass spectrometry and nuclear magnetic resonance. 

Beart, J.E., Lilley, T.H., and Haslam, E. 1985. Polyphenol interactions. Part 2. Covalent binding of procyanidins to proteins during acid-catalysed decomposition observations on some pol ymeri c proanthocyanidins../. Chem. Soc. Perkin Trans. II 1439-1443. 

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