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Chemical Compound Review

Caffeate     (Z)-3-(3,4- dihydroxyphenyl)prop-2-enoic acid

Synonyms: Caffeicacid, Lopac-C-0625, SureCN3682144, CHEBI:17395, HMDB01964, ...
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Disease relevance of Caffeate

  • We report crystallographic analyses of unliganded Rhodobacter sphaeroides tyrosine ammonia-lyase (RsTAL) and RsTAL bound to p-coumarate and caffeate [1].
  • Inhibition of tumor metastasis by sodium caffeate and its effect on angiogenesis [2].
  • Chemiosmotic energy conservation with Na(+) as the coupling ion during hydrogen-dependent caffeate reduction by Acetobacterium woodii [3].
  • In an appropriate genetic background, it was possible to select for an Acinetobacter strain that had lost the ability to grow with caffeate, a commonly occurring hydroxycinnamate [4].
  • In conclusion, we demonstrate that a novel potent antioxidant, octyl caffeate, significantly ameliorates circulatory failure of endotoxemia in vivo by a mechanism involving suppression of iNOS expression through inactivation of mitogen-activated protein kinases in RASMCs [5].

High impact information on Caffeate


Chemical compound and disease context of Caffeate


Biological context of Caffeate

  • Octyl caffeate (0.1-1.0 microM) exerted a concentration-dependent inhibition of iron-catalyzed lipid peroxidation in rat brain homogenates [5].
  • The sodium ionophore ETH2120, but not protonophores, stimulated hydrogen-dependent caffeate reduction by 280%, indicating that caffeate reduction is coupled to the buildup of a membrane potential generated by primary Na(+) extrusion [3].
  • Caffeic acid, methyl caffeate, rosmarinic acid, and luteolin 7-O-glucuronide-6"-methyl ester were isolated as active constituents from the extract of the typical strain of P. frutescens, and their IC50 values for PDGF-induced mesangial cell proliferation were estimated as 26 microM, 2.6 microM, 1.8 microM, and 4.1 microM, respectively [9].
  • Both copper and iron enhanced the radical intensity of ascorbates, but slightly reduced the radical intensity of gallate and caffeate, suggesting that radical intensity is not the sole determinant of apoptosis induction [10].
  • Copper also stimulated the gallate or caffeate-induced apoptotic cell death, whereas iron was inhibitory [10].

Anatomical context of Caffeate


Associations of Caffeate with other chemical compounds


Gene context of Caffeate

  • These results suggest that ROS generated through activation of NADPH oxidase may play an essential role in the apoptosis induced by CA and FA in HepG2 cells [14].


  1. Structural determinants and modulation of substrate specificity in phenylalanine-tyrosine ammonia-lyases. Louie, G.V., Bowman, M.E., Moffitt, M.C., Baiga, T.J., Moore, B.S., Noel, J.P. Chem. Biol. (2006) [Pubmed]
  2. Inhibition of tumor metastasis by sodium caffeate and its effect on angiogenesis. Xu, F., Song, D., Zhen, Y. Oncology (2004) [Pubmed]
  3. Chemiosmotic energy conservation with Na(+) as the coupling ion during hydrogen-dependent caffeate reduction by Acetobacterium woodii. Imkamp, F., Müller, V. J. Bacteriol. (2002) [Pubmed]
  4. Genes for chlorogenate and hydroxycinnamate catabolism (hca) are linked to functionally related genes in the dca-pca-qui-pob-hca chromosomal cluster of Acinetobacter sp. strain ADP1. Smith, M.A., Weaver, V.B., Young, D.M., Ornston, L.N. Appl. Environ. Microbiol. (2003) [Pubmed]
  5. A novel antioxidant, octyl caffeate, suppression of LPS/IFN-gamma-induced inducible nitric oxide synthase gene expression in rat aortic smooth muscle cells. Hsiao, G., Shen, M.Y., Chang, W.C., Cheng, Y.W., Pan, S.L., Kuo, Y.H., Chen, T.F., Sheu, J.R. Biochem. Pharmacol. (2003) [Pubmed]
  6. Field and pulping performances of transgenic trees with altered lignification. Pilate, G., Guiney, E., Holt, K., Petit-Conil, M., Lapierre, C., Leplé, J.C., Pollet, B., Mila, I., Webster, E.A., Marstorp, H.G., Hopkins, D.W., Jouanin, L., Boerjan, W., Schuch, W., Cornu, D., Halpin, C. Nat. Biotechnol. (2002) [Pubmed]
  7. 5-hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation, a new view of monolignol biosynthesis in angiosperms. Li, L., Popko, J.L., Umezawa, T., Chiang, V.L. J. Biol. Chem. (2000) [Pubmed]
  8. Toxicity caused by hydroxycinnamoyl-coenzyme A thioester accumulation in mutants of Acinetobacter sp. strain ADP1. Parke, D., Ornston, L.N. Appl. Environ. Microbiol. (2004) [Pubmed]
  9. Inhibitory effect of Perilla frutescens and its phenolic constituents on cultured murine mesangial cell proliferation. Makino, T., Ono, T., Muso, E., Honda, G. Planta Med. (1998) [Pubmed]
  10. Copper, but not iron, enhances apoptosis-inducing activity of antioxidants. Satoh, K., Kadofuku, T., Sakagami, H. Anticancer Res. (1997) [Pubmed]
  11. Dehydrodimers of caffeic acid in the cell walls of suspension-cultured Mentha. Yang, J.G., Uchiyama, T. Biosci. Biotechnol. Biochem. (2000) [Pubmed]
  12. Sodium caffeate induces endothelial cell apoptosis and inhibits VEGF expression in cancer cells. Xu, F., Ou-Yang, Z.G., Zhang, S.H., Song, D.Q., Shao, R.G., Zhen, Y.S. Yao Xue Xue Bao (2006) [Pubmed]
  13. Purification and properties of a feruloyl esterase involved in lignocellulose degradation by Aureobasidium pullulans. Rumbold, K., Biely, P., Mastihubová, M., Gudelj, M., Gübitz, G., Robra, K.H., Prior, B.A. Appl. Environ. Microbiol. (2003) [Pubmed]
  14. Role of NADPH oxidase-mediated generation of reactive oxygen species in the mechanism of apoptosis induced by phenolic acids in HepG2 human hepatoma cells. Lee, Y.S. Arch. Pharm. Res. (2005) [Pubmed]
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