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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

epiafzelechin     (2S,3R)-2-(4- hydroxyphenyl)chroman- 3,5,7...

Synonyms: epi-Afzelechin, SPECTRUM202178, CHEMBL159303, SureCN557061, BSPBio_003210, ...
 
 
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High impact information on C12128

 

Biological context of C12128

 

Anatomical context of C12128

 

Associations of C12128 with other chemical compounds

  • We confirmed by HPLC/DAD and LC/ESI-MS analyses that some of these anthocyanin pigments generated in rosé cider during vinification corresponded to those formed in model cider containing anthocyanin and flavan-3-ol in the presence of acetaldehyde [13].
  • Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments [14].
  • A new flavone xyloside and two new flavan-3-ol glucosides from Juniperus communis var. depressa [15].
 

Gene context of C12128

  • Retention of the investigated compounds by the SDS micelles is affected by (i) the stereochemistry of the heterocycle of the flavan-3-ol skeleton, (ii) the molecular size, the number and position of free phenolic hydroxy groups, and (iii) the type of acyl residues attached at the C-3 hydroxy function [16].
  • Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus [17].
  • Dietary flavonoids including (-)-epicatechin, a major flavan-3-ol in cocoa products, grapes and wine, are substrates of MPO as well as potent inhibitors of LPO in LDL at micromolar concentrations [18].
 

Analytical, diagnostic and therapeutic context of C12128

  • Data presented in this work confirm the great utility of atmospheric pressure-ionisation electrospray mass spectrometry coupled to HPLC for analysis of phenolic compounds, under negative mode in the case of low-molecular mass phenols, and under both positive and negative modes in flavan-3-ol compounds [19].
  • These flavan-3-ol metabolites were not detected in plasma from the control group [20].

References

  1. Neuroprotective effects of green and black teas and their catechin gallate esters against beta-amyloid-induced toxicity. Bastianetto, S., Yao, Z.X., Papadopoulos, V., Quirion, R. Eur. J. Neurosci. (2006) [Pubmed]
  2. Catechin is metabolized by both the small intestine and liver of rats. Donovan, J.L., Crespy, V., Manach, C., Morand, C., Besson, C., Scalbert, A., Rémésy, C. J. Nutr. (2001) [Pubmed]
  3. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods. Gu, L., Kelm, M.A., Hammerstone, J.F., Zhang, Z., Beecher, G., Holden, J., Haytowitz, D., Prior, R.L. Journal of mass spectrometry : JMS. (2003) [Pubmed]
  4. Flavan-3-ols isolated from some medicinal plants inhibiting COX-1 and COX-2 catalysed prostaglandin biosynthesis. Noreen, Y., Serrano, G., Perera, P., Bohlin, L. Planta Med. (1998) [Pubmed]
  5. Inhibition of platelet activation and endothelial cell injury by flavan-3-ol and saikosaponin compounds. Chang, W.C., Hsu, F.L. Prostaglandins Leukot. Essent. Fatty Acids (1991) [Pubmed]
  6. Percutaneous absorption of flavan-3-ol conjugates from plant procyanidins. Alonso, C., Ramón, E., Lozano, C., Parra, J.L., Torres, J.L., Coderch, L. Drugs under experimental and clinical research. (2004) [Pubmed]
  7. Inhibitory effects of oolong tea polyphenols on pancreatic lipase in vitro. Nakai, M., Fukui, Y., Asami, S., Toyoda-Ono, Y., Iwashita, T., Shibata, H., Mitsunaga, T., Hashimoto, F., Kiso, Y. J. Agric. Food Chem. (2005) [Pubmed]
  8. Adsorption of phenolic compounds and browning products in white wines by yeasts and their cell walls. Razmkhab, S., Lopez-Toledano, A., Ortega, J.M., Mayen, M., Merida, J., Medina, M. J. Agric. Food Chem. (2002) [Pubmed]
  9. Activities of plant-derived phenols in a fibroblast cell culture model. Koganov, M.M., Dueva, O.V., Tsorin, B.L. J. Nat. Prod. (1999) [Pubmed]
  10. The absorption, metabolism and excretion of flavan-3-ols and procyanidins following the ingestion of a grape seed extract by rats. Tsang, C., Auger, C., Mullen, W., Bornet, A., Rouanet, J.M., Crozier, A., Teissedre, P.L. Br. J. Nutr. (2005) [Pubmed]
  11. The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells. Chang, J.J., Chen, T.H., Chan, P., Chen, Y.J., Hsu, F.L., Lo, M.Y., Lin, J.Y. Pharmacology (2001) [Pubmed]
  12. Effect of flavan-3-ol tannins purified from Camellia sinensis on lipid peroxidation of rat heart mitochondria. Hong, C.Y., Wang, C.P., Lo, Y.C., Hsu, F.L. Am. J. Chin. Med. (1994) [Pubmed]
  13. Characterization and structures of anthocyanin pigments generated in rosé cider during vinification. Shoji, T., Goda, Y., Toyoda, M., Yanagida, A., Kanda, T. Phytochemistry (2002) [Pubmed]
  14. Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates. van Rensburg, W.J., Ferreira, D., Malan, E., Steenkamp, J.A. Phytochemistry (2000) [Pubmed]
  15. A new flavone xyloside and two new flavan-3-ol glucosides from Juniperus communis var. depressa. Iida, N., Inatomi, Y., Murata, H., Inada, A., Murata, J., Lang, F.A., Matsuura, N., Nakanishi, T. Chem. Biodivers. (2007) [Pubmed]
  16. Separations of Flavan-3-ols and Dimeric Proanthocyanidins by Capillary Electrophoresis. Kreimeyer, J., Petereit, F., Nahrstedt, A. Planta Med. (1998) [Pubmed]
  17. Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus. Hwang, B.Y., Kim, H.S., Lee, J.H., Hong, Y.S., Ro, J.S., Lee, K.S., Lee, J.J. J. Nat. Prod. (2001) [Pubmed]
  18. Myeloperoxidase-induced lipid peroxidation of LDL in the presence of nitrite. Protection by cocoa flavanols. Schewe, T., Sies, H. Biofactors (2005) [Pubmed]
  19. Various applications of liquid chromatography-mass spectrometry to the analysis of phenolic compounds. Pérez-Magariño, S., Revilla, I., González-SanJosé, M.L., Beltrán, S. Journal of chromatography. A. (1999) [Pubmed]
  20. The influence of moderate red wine consumption on antioxidant status and indices of oxidative stress associated with CHD in healthy volunteers. Tsang, C., Higgins, S., Duthie, G.G., Duthie, S.J., Howie, M., Mullen, W., Lean, M.E., Crozier, A. Br. J. Nutr. (2005) [Pubmed]
 
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