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Chemical Compound Review

Distylin     (2S,3R)-2-(3,4- dihydroxyphenyl)-3,5,7...

Synonyms: TAXIFOLIN, Taxifoliol, TAXIFOLIN-(+), CHEMBL66, SureCN39786, ...
 
 
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Disease relevance of Catechin hydrate

 

High impact information on Catechin hydrate

 

Biological context of Catechin hydrate

 

Anatomical context of Catechin hydrate

  • Much smaller dosages of taxifolin were required in primary keratinocytes compared to HaCaT (immortalized cell) to achieve similar levels of inhibition in the inducible ICAM-1 expression [7].
  • Prevention of macrophage adhesion molecule-1 (Mac-1)-dependent neutrophil firm adhesion by taxifolin through impairment of protein kinase-dependent NADPH oxidase activation and antagonism of G protein-mediated calcium influx [11].
  • Production of both ROS and NO by leukocytes and microglial cells was significantly antagonized by taxifolin [2].
  • Taxifolin protected peroxy radical-damaged mitochondria with no effect on enzyme activity [3].
 

Associations of Catechin hydrate with other chemical compounds

 

Gene context of Catechin hydrate

  • Among the flavonoids tested, taxifolin was the most potent in inhibiting interferon gamma (IFN gamma)-induced ICAM-1 protein as well as mRNA expression in human keratinocytes [7].
  • Flavonoids without a C2-C3 double bond like eriodictyol, taxifolin and catechin did not inhibit GS-X pump activity [17].
  • In summary, taxifolin reduced apoB secretion by limiting TG availability via DGAT and MTP activity [18].
  • In conclusion, we propose that impairment of ROS production by NADPH oxidase through interfering with p38 MAPK- and/or PKC-dependent signals, and antagonism of G protein-mediated calcium influx may account for the inhibition of Mac-1-dependent neutrophil firm adhesion that confers taxifolin the anti-inflammatory activity [11].
  • Taxifolin inhibited leukocyte infiltration, and COX-2 and iNOS expressions in CI/R-injured brain [2].
 

Analytical, diagnostic and therapeutic context of Catechin hydrate

  • Taxifolin was shown by ELISA to markedly reduce apoB secretion under basal and lipid-rich conditions up to 63% at 200 micromol/L [18].
  • Structural elucidation was carried out by spectroscopic methods, and the absolute configurations of C-2 and C-3 in taxifolin 3-O-arabinosides were determined on the basis of circular dichroism [19].
  • The results indicated that some compounds, such as taxifolin (2) and its tetramethylated derivative (4) exhibited potent and dose-dependent antinociceptive action against acetic acid-induced abdominal constriction when administered intraperitoneally or orally [20].

References

  1. Structurally related antitumor effects of flavanones in vitro and in vivo: involvement of caspase 3 activation, p21 gene expression, and reactive oxygen species production. Shen, S.C., Ko, C.H., Tseng, S.W., Tsai, S.H., Chen, Y.C. Toxicol. Appl. Pharmacol. (2004) [Pubmed]
  2. Taxifolin ameliorates cerebral ischemia-reperfusion injury in rats through its anti-oxidative effect and modulation of NF-kappa B activation. Wang, Y.H., Wang, W.Y., Chang, C.C., Liou, K.T., Sung, Y.J., Liao, J.F., Chen, C.F., Chang, S., Hou, Y.C., Chou, Y.C., Shen, Y.C. J. Biomed. Sci. (2006) [Pubmed]
  3. Protection against oxidative damage by dihydroflavonols in Engelhardtia chrysolepis. Haraguchi, H., Mochida, Y., Sakai, S., Masuda, H., Tamura, Y., Mizutani, K., Tanaka, O., Chou, W.H. Biosci. Biotechnol. Biochem. (1996) [Pubmed]
  4. Structure-property studies on the antioxidant activity of flavonoids present in diet. Teixeira, S., Siquet, C., Alves, C., Boal, I., Marques, M.P., Borges, F., Lima, J.L., Reis, S. Free Radic. Biol. Med. (2005) [Pubmed]
  5. Modulation of hepatic lipoprotein synthesis and secretion by taxifolin, a plant flavonoid. Theriault, A., Wang, Q., Van Iderstine, S.C., Chen, B., Franke, A.A., Adeli, K. J. Lipid Res. (2000) [Pubmed]
  6. Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity. Boerboom, A.M., Vermeulen, M., van der Woude, H., Bremer, B.I., Lee-Hilz, Y.Y., Kampman, E., van Bladeren, P.J., Rietjens, I.M., Aarts, J.M. Biochem. Pharmacol. (2006) [Pubmed]
  7. Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action. Bito, T., Roy, S., Sen, C.K., Shirakawa, T., Gotoh, A., Ueda, M., Ichihashi, M., Packer, L. FEBS Lett. (2002) [Pubmed]
  8. An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers. Schutte, M.E., Freidig, A.P., van de Sandt, J.J., Alink, G.M., Rietjens, I.M., Groten, J.P. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  9. Differential inhibition of proliferation of human squamous cell carcinoma, gliosarcoma and embryonic fibroblast-like lung cells in culture by plant flavonoids. Kandaswami, C., Perkins, E., Drzewiecki, G., Soloniuk, D.S., Middleton, E. Anticancer Drugs (1992) [Pubmed]
  10. Assessing estrogenic activity of phytochemicals using transcriptional activation and immature mouse uterotrophic responses. Jefferson, W.N., Padilla-Banks, E., Clark, G., Newbold, R.R. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2002) [Pubmed]
  11. Prevention of macrophage adhesion molecule-1 (Mac-1)-dependent neutrophil firm adhesion by taxifolin through impairment of protein kinase-dependent NADPH oxidase activation and antagonism of G protein-mediated calcium influx. Wang, Y.H., Wang, W.Y., Liao, J.F., Chen, C.F., Hou, Y.C., Liou, K.T., Chou, Y.C., Tien, J.H., Shen, Y.C. Biochem. Pharmacol. (2004) [Pubmed]
  12. Myeloperoxidase/nitrite-mediated lipid peroxidation of low-density lipoprotein as modulated by flavonoids. Kostyuk, V.A., Kraemer, T., Sies, H., Schewe, T. FEBS Lett. (2003) [Pubmed]
  13. The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. Awad, H.M., Boersma, M.G., Boeren, S., van Bladeren, P.J., Vervoort, J., Rietjens, I.M. Chem. Res. Toxicol. (2002) [Pubmed]
  14. Simultaneous quantification of five major bioactive flavonoids in Rhizoma Smilacis Glabrae by high-performance liquid chromatography. Chen, L., Yin, Y., Yi, H., Xu, Q., Chen, T. Journal of pharmaceutical and biomedical analysis (2007) [Pubmed]
  15. Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate. Lee, K.G., Shibamoto, T., Takeoka, G.R., Lee, S.E., Kim, J.H., Park, B.S. J. Agric. Food Chem. (2003) [Pubmed]
  16. Transgenic rice lines expressing maize C1 and R-S regulatory genes produce various flavonoids in the endosperm. Shin, Y.M., Park, H.J., Yim, S.D., Baek, N.I., Lee, C.H., An, G., Woo, Y.M. Plant Biotechnol. J. (2006) [Pubmed]
  17. Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells. van Zanden, J.J., Geraets, L., Wortelboer, H.M., van Bladeren, P.J., Rietjens, I.M., Cnubben, N.H. Biochem. Pharmacol. (2004) [Pubmed]
  18. Inhibitory activity of diacylglycerol acyltransferase (DGAT) and microsomal triglyceride transfer protein (MTP) by the flavonoid, taxifolin, in HepG2 cells: potential role in the regulation of apolipoprotein B secretion. Casaschi, A., Rubio, B.K., Maiyoh, G.K., Theriault, A.G. Atherosclerosis (2004) [Pubmed]
  19. Structural studies of zoospore attractants from Trachelospermum jasminoides var. pubescens: taxifolin 3-O-glycosides. Hosoi, S., Shimizu, E., Ohno, K., Yokosawa, R., Kuninaga, S., Coskun, M., Sakushima, A. Phytochemical analysis : PCA. (2006) [Pubmed]
  20. Antinociceptive and anti-oedematogenic properties of astilbin, taxifolin and some related compounds. Cechinel-Filho, V., Vaz, Z.R., Zunino, L., Calixto, J.B., Yunes, R.A. Arzneimittel-Forschung. (2000) [Pubmed]
 
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