The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Vitisinol     2-(3,4-dihydroxyphenyl)-2-[2- (3,4...

Synonyms: Procyanidin, amurensisin, AC1Q7ACM, LS-39919, AR-1C7081, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of BRN 1675863


High impact information on BRN 1675863

  • Because mutations at Asp-309, Ser-378, and His-480 of aromatase significantly affected the binding of the procyanidin B dimer, these active site residues are thought to be important residues that interact with this phytochemical [1].
  • These in vitro and in vivo studies demonstrated that procyanidin B dimers in red wine and grape seeds could be used as chemopreventive agents against breast cancer by suppressing in situ estrogen biosynthesis [1].
  • Thus, in this study we investigated the capacity of a hexameric procyanidin fraction (Hex) isolated from cocoa to protect Caco-2 cells from deoxycholic (DOC)-induced cytotoxicity, cell oxidant increase, and loss of monolayer integrity [6].
  • The procyanidin-rich maritime pine bark extract Pycnogenol has well-documented antioxidant and anti-inflammatory activity [7].
  • OBJECTIVE: This study sought to evaluate whether 28 d of supplementation with cocoa flavanols and related procyanidin oligomers would modulate human platelet reactivity and primary hemostasis and reduce oxidative markers in vivo [8].

Chemical compound and disease context of BRN 1675863


Biological context of BRN 1675863

  • Fractions V-VIII, however, caused significant growth inhibition and apoptosis with the highest activity present in the later fractions that contained procyanidin trimers and GA esters of dimers and trimers [12].
  • In addition, the position of linkage between inter-flavan units also influences lipid peroxidation activity; procyanidin isomers with a 4-6 linkage showed stronger inhibitory activity than isomers with a 4-8 linkage [13].
  • In contrast, procyanidin trimers, pentamers and DRW inhibited the platelet activation in response to epinephrine [14].
  • In the presence of PHA, gene expression also seemed to be most affected by the larger procyanidin fractions [15].
  • For the purpose of examining the hair-growing mechanisms of procyanidin B-3, we examined its relationship to the TGF-beta signal pathway, which is known to be a regulator of catagen induction [16].

Anatomical context of BRN 1675863


Associations of BRN 1675863 with other chemical compounds

  • A sharp increase in the inhibition of epidermal lipid peroxidation was also evident when a gallate group was linked at the 3'-hydroxy position of a procyanidin dimer [13].
  • This paper describes the characterization of procyanidin mixtures by acid depolymerization in the presence of cysteine (thiolysis with cysteine) and micellar electrokinetic chromatography (MEKC) [21].
  • The above data support the theories that in healthy adults, 1) a positive relationship exists between procyanidin consumption and plasma procyanidin concentration and 2) the rise in plasma epicatechin contributes to the ability of plasma to scavenge free radicals and to inhibit lipid peroxidation [22].
  • Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin [23].
  • By means of mass spectrometry, 1H-NMR, and 13C-NMR analyses, one substance was revealed to be procyanidin B-3 and the other substance was identified as (+)-catechin [16].

Gene context of BRN 1675863


Analytical, diagnostic and therapeutic context of BRN 1675863

  • Using UV absorbance analysis, high-performance liquid chromatography profiling, accurate mass-mass spectrometry, and nanospray tandem mass spectrometry, most of the compounds in our red wine fraction were identified as procyanidin B dimers that were shown to be aromatase inhibitors [1].
  • Procyanidin oligomers eluting in HPLC Fractions 2 and 3 were obtained in larger quantities by separating GSE into eight fractions (I-VIII) on a gel filtration column [12].
  • The MEKC procedures here reported, are cheap, reliable and fast, and their potential in the determination of the size and composition in procyanidin mixtures has been shown [21].
  • Perfusion of isolated small intestine with the procyanidin dimers B2 and B5 extracted from cocoa indicated that both forms of dimer are transferred to the serosal side of enterocytes but only to a very small extent (<1% of the total transferred flavanol-like compounds) [20].
  • Using the patch-clamp technique, we measured the effects of Crataegus extract (10 mg/l; flavonoid content: 2.25%, total procyanidin content: 11.3 +/- 0.4%) on the inward rectifier and the delayed rectifier potassium current in isolated guinea pig ventricular myocytes [27].


  1. Suppression of estrogen biosynthesis by procyanidin dimers in red wine and grape seeds. Eng, E.T., Ye, J., Williams, D., Phung, S., Moore, R.E., Young, M.K., Gruntmanis, U., Braunstein, G., Chen, S. Cancer Res. (2003) [Pubmed]
  2. Solar ultraviolet-induced erythema in human skin and nuclear factor-kappa-B-dependent gene expression in keratinocytes are modulated by a French maritime pine bark extract. Saliou, C., Rimbach, G., Moini, H., McLaughlin, L., Hosseini, S., Lee, J., Watson, R.R., Packer, L. Free Radic. Biol. Med. (2001) [Pubmed]
  3. Procyanidin trimers to pentamers fractionated from apple inhibit melanogenesis in B16 mouse melanoma cells. Shoji, T., Masumoto, S., Moriichi, N., Kobori, M., Kanda, T., Shinmoto, H., Tsushida, T. J. Agric. Food Chem. (2005) [Pubmed]
  4. Induction of apoptosis by three types of procyanidin isolated from apple (Rosaceae Malus pumila) in human stomach cancer KATO III cells. Hibasami, H., Shohji, T., Shibuya, I., Higo, K., Kanda, T. Int. J. Mol. Med. (2004) [Pubmed]
  5. Cytotoxicity of bioactive polymeric fractions from grape cell culture on human hepatocellular carcinoma, murine leukemia and non-cancerous PK15 kidney cells. Jo, J.Y., de Mejia, E.G., Lila, M.A. Food Chem. Toxicol. (2006) [Pubmed]
  6. Procyanidins protect Caco-2 cells from bile acid- and oxidant-induced damage. Erlejman, A.G., Fraga, C.G., Oteiza, P.I. Free Radic. Biol. Med. (2006) [Pubmed]
  7. Antioxidant activity and inhibition of matrix metalloproteinases by metabolites of maritime pine bark extract (pycnogenol). Grimm, T., Schäfer, A., Högger, P. Free Radic. Biol. Med. (2004) [Pubmed]
  8. Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Murphy, K.J., Chronopoulos, A.K., Singh, I., Francis, M.A., Moriarty, H., Pike, M.J., Turner, A.H., Mann, N.J., Sinclair, A.J. Am. J. Clin. Nutr. (2003) [Pubmed]
  9. Influence of cocoa flavanols and procyanidins on free radical-induced human erythrocyte hemolysis. Zhu, Q.Y., Schramm, D.D., Gross, H.B., Holt, R.R., Kim, S.H., Yamaguchi, T., Kwik-Uribe, C.L., Keen, C.L. Clin. Dev. Immunol. (2005) [Pubmed]
  10. Inhibitory effects of cocoa flavanols and procyanidin oligomers on free radical-induced erythrocyte hemolysis. Zhu, Q.Y., Holt, R.R., Lazarus, S.A., Orozco, T.J., Keen, C.L. Exp. Biol. Med. (Maywood) (2002) [Pubmed]
  11. Polyphenolic constituent structures of Zanthoxylum piperitum fruit and the antibacterial effects of its polymeric procyanidin on methicillin-resistant Staphylococcus aureus. Kusuda, M., Inada, K., Ogawa, T.O., Yoshida, T., Shiota, S., Tsuchiya, T., Hatano, T. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  12. Fractionation of grape seed extract and identification of gallic acid as one of the major active constituents causing growth inhibition and apoptotic death of DU145 human prostate carcinoma cells. Veluri, R., Singh, R.P., Liu, Z., Thompson, J.A., Agarwal, R., Agarwal, C. Carcinogenesis (2006) [Pubmed]
  13. Anti-tumor-promoting activity of a polyphenolic fraction isolated from grape seeds in the mouse skin two-stage initiation-promotion protocol and identification of procyanidin B5-3'-gallate as the most effective antioxidant constituent. Zhao, J., Wang, J., Chen, Y., Agarwal, R. Carcinogenesis (1999) [Pubmed]
  14. Cocoa and wine polyphenols modulate platelet activation and function. Rein, D., Paglieroni, T.G., Pearson, D.A., Wun, T., Schmitz, H.H., Gosselin, R., Keen, C.L. J. Nutr. (2000) [Pubmed]
  15. Cocoa procyanidins and human cytokine transcription and secretion. Mao, T., Van De Water, J., Keen, C.L., Schmitz, H.H., Gershwin, M.E. J. Nutr. (2000) [Pubmed]
  16. Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1. Kamimura, A., Takahashi, T. Exp. Dermatol. (2002) [Pubmed]
  17. Chocolate procyanidins decrease the leukotriene-prostacyclin ratio in humans and human aortic endothelial cells. Schramm, D.D., Wang, J.F., Holt, R.R., Ensunsa, J.L., Gonsalves, J.L., Lazarus, S.A., Schmitz, H.H., German, J.B., Keen, C.L. Am. J. Clin. Nutr. (2001) [Pubmed]
  18. Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo. Takahashi, T., Kamiya, T., Hasegawa, A., Yokoo, Y. J. Invest. Dermatol. (1999) [Pubmed]
  19. Activity of monomeric, dimeric, and trimeric flavonoids on NO production, TNF-alpha secretion, and NF-kappaB-dependent gene expression in RAW 264.7 macrophages. Park, Y.C., Rimbach, G., Saliou, C., Valacchi, G., Packer, L. FEBS Lett. (2000) [Pubmed]
  20. Epicatechin is the primary bioavailable form of the procyanidin dimers B2 and B5 after transfer across the small intestine. Spencer, J.P., Schroeter, H., Shenoy, B., Srai, S.K., Debnam, E.S., Rice-Evans, C. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  21. Micellar electrokinetic chromatography estimation of size and composition of procyanidins after thiolysis with cysteine. Herrero-Martínez, J.M., Ràfols, C., Rosés, M., Bosch, E., Lozano, C., Torres, J.L. Electrophoresis (2003) [Pubmed]
  22. A dose-response effect from chocolate consumption on plasma epicatechin and oxidative damage. Wang, J.F., Schramm, D.D., Holt, R.R., Ensunsa, J.L., Fraga, C.G., Schmitz, H.H., Keen, C.L. J. Nutr. (2000) [Pubmed]
  23. Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin. Wellmann, F., Griesser, M., Schwab, W., Martens, S., Eisenreich, W., Matern, U., Lukacin, R. FEBS Lett. (2006) [Pubmed]
  24. Potentiation of apple procyanidin-triggered apoptosis by the polyamine oxidase inactivator MDL 72527 in human colon cancer-derived metastatic cells. Gossé, F., Roussi, S., Guyot, S., Schoenfelder, A., Mann, A., Bergerat, J.P., Seiler, N., Raul, F. Int. J. Oncol. (2006) [Pubmed]
  25. Inhibitory effect of procyanidin oligomer from elm cortex on the matrix metalloproteinases and proteases of periodontopathogens. Song, S.E., Choi, B.K., Kim, S.N., Yoo, Y.J., Kim, M.M., Park, S.K., Roh, S.S., Kim, C.K. J. Periodont. Res. (2003) [Pubmed]
  26. Procyanidin oligomers counteract TGF-beta1- and TGF-beta2-induced apoptosis in hair epithelial cells: an insight into their mechanisms. Kamimura, A., Takahashi, T., Morohashi, M., Takano, Y. Skin pharmacology and physiology. (2006) [Pubmed]
  27. Crataegus extract blocks potassium currents in guinea pig ventricular cardiac myocytes. Müller, A., Linke, W., Klaus, W. Planta Med. (1999) [Pubmed]
WikiGenes - Universities