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Chemical Compound Review

SureCN987261     (1S,3R,4R,5R)-3-[3-(3,4...

Synonyms: AG-J-75937, KBioSS_002357, SPBio_001836, SPBio_002353, NSC70861, ...
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Disease relevance of CHLOROGENIC ACID


Psychiatry related information on CHLOROGENIC ACID


High impact information on CHLOROGENIC ACID


Chemical compound and disease context of CHLOROGENIC ACID

  • Thus, we report the bimodal occurrence of hippuric acid and chlorogenic acid metabolites in a genetically homogeneous population of rats maintained under identical conditions, which may have significance in relation to the understanding of the consequences of biochemical variation in animals used for drug toxicity testing [11].
  • Among them, caffeic acid exhibited the strongest activity against HSV-1 (EC50=15.3 microg/ml, SI=671), HSV-2 (EC50=87.3 microg/ml, SI=118) and ADV-3 (EC50=14.2 microg/ml, SI=727), whereas chlorogenic acid possessed the strongest anti-ADV-11 (EC50=13.3 microg/ml, SI=301) activity [12].
  • The aim of this study was to investigate the effects of different pure polyphenols [quercetin, chlorogenic acid, and (-)-epicatechin] and natural fruit extracts (strawberry and plum) on viability or apoptosis of human hepatoma HepG2 cells [13].
  • We suggested that the protective effect of the stem bark of A. senticosus on gastric ulcer may be partially due to those of chlorogenic acid and syringaresinol di-o-beta-D-glucoside [14].
  • Paraquat in the diet markedly decreased the liver triacylglycerol and phospholipid concentrations, as well as the food intake and body weight gain, while chlorogenic acid protected against these decreases [15].

Biological context of CHLOROGENIC ACID


Anatomical context of CHLOROGENIC ACID

  • Effects of acute inhibition of glucose-6-phosphatase activity by the chlorogenic acid derivative S4048 on hepatic carbohydrate fluxes were examined in isolated rat hepatocytes and in vivo in rats [16].
  • Tobacco glycoprotein (TGP) purified from flue-cured tobacco leaves, tar-derived material (TAR), the water soluble, nondialyzable, delipidized extract of cigarette smoke condensate, rutin-bovine serum albumin conjugates, quercetin, and chlorogenic acid are mitogenic for bovine aortic smooth-muscle cells, but not adventitial fibroblasts [20].
  • Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (Gl-6-P translocase) of this enzyme system in microsomes of rat liver [18].
  • Chlorogenic acid and its metabolites were estimated in the stomach, small intestine and cecal contents as well as in bladder urine and plasma by HPLC with coulometric detection at several time points (1.5, 3, 4.5, and 7 h) after the beginning of the meal [21].
  • Chlorogenic acid and caffeic acid appeared early (at 1.5 h) in plasma and urine, suggesting an absorption of chlorogenic acid into the upper part of the gastrointestinal tract [21].

Associations of CHLOROGENIC ACID with other chemical compounds


Gene context of CHLOROGENIC ACID


Analytical, diagnostic and therapeutic context of CHLOROGENIC ACID


  1. Chlorogenic acid inhibits Bcr-Abl tyrosine kinase and triggers p38 mitogen-activated protein kinase-dependent apoptosis in chronic myelogenous leukemic cells. Bandyopadhyay, G., Biswas, T., Roy, K.C., Mandal, S., Mandal, C., Pal, B.C., Bhattacharya, S., Rakshit, S., Bhattacharya, D.K., Chaudhuri, U., Konar, A., Bandyopadhyay, S. Blood (2004) [Pubmed]
  2. Coffee, diabetes, and weight control. Greenberg, J.A., Boozer, C.N., Geliebter, A. Am. J. Clin. Nutr. (2006) [Pubmed]
  3. Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H-NMR spectroscopy and multivariate data analysis. Choi, Y.H., Tapias, E.C., Kim, H.K., Lefeber, A.W., Erkelens, C., Verhoeven, J.T., Brzin, J., Zel, J., Verpoorte, R. Plant Physiol. (2004) [Pubmed]
  4. Chlorogenic acid attenuates hypertension and improves endothelial function in spontaneously hypertensive rats. Suzuki, A., Yamamoto, N., Jokura, H., Yamamoto, M., Fujii, A., Tokimitsu, I., Saito, I. J. Hypertens. (2006) [Pubmed]
  5. 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]
  6. Effects of chlorogenic Acid and its metabolites on spontaneous locomotor activity in mice. Ohnishi, R., Ito, H., Iguchi, A., Shinomiya, K., Kamei, C., Hatano, T., Yoshida, T. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  7. Engineering plants with increased levels of the antioxidant chlorogenic acid. Niggeweg, R., Michael, A.J., Martin, C. Nat. Biotechnol. (2004) [Pubmed]
  8. Increased disease susceptibility of transgenic tobacco plants with suppressed levels of preformed phenylpropanoid products. Maher, E.A., Bate, N.J., Ni, W., Elkind, Y., Dixon, R.A., Lamb, C.J. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Huang, M.T., Lysz, T., Ferraro, T., Abidi, T.F., Laskin, J.D., Conney, A.H. Cancer Res. (1991) [Pubmed]
  10. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Huang, M.T., Smart, R.C., Wong, C.Q., Conney, A.H. Cancer Res. (1988) [Pubmed]
  11. Directly coupled high-performance liquid chromatography and nuclear magnetic resonance spectroscopic with chemometric studies on metabolic variation in Sprague--Dawley rats. Gavaghan, C.L., Nicholson, J.K., Connor, S.C., Wilson, I.D., Wright, B., Holmes, E. Anal. Biochem. (2001) [Pubmed]
  12. Antiviral activity of Plantago major extracts and related compounds in vitro. Chiang, L.C., Chiang, W., Chang, M.Y., Ng, L.T., Lin, C.C. Antiviral Res. (2002) [Pubmed]
  13. Comparative effects of food-derived polyphenols on the viability and apoptosis of a human hepatoma cell line (HepG2). Ramos, S., Alía, M., Bravo, L., Goya, L. J. Agric. Food Chem. (2005) [Pubmed]
  14. Protective effects of Acanthopanax senticosus Harms from Hokkaido and its components on gastric ulcer in restrained cold water stressed rats. Fujikawa, T., Yamaguchi, A., Morita, I., Takeda, H., Nishibe, S. Biol. Pharm. Bull. (1996) [Pubmed]
  15. Protective effects of chlorogenic acid on paraquat-induced oxidative stress in rats. Tsuchiya, T., Suzuki, O., Igarashi, K. Biosci. Biotechnol. Biochem. (1996) [Pubmed]
  16. Acute inhibition of hepatic glucose-6-phosphatase does not affect gluconeogenesis but directs gluconeogenic flux toward glycogen in fasted rats. A pharmacological study with the chlorogenic acid derivative S4048. van Dijk, T.H., van der Sluijs, F.H., Wiegman, C.H., Baller, J.F., Gustafson, L.A., Burger, H.J., Herling, A.W., Kuipers, F., Meijer, A.J., Reijngoud, D.J. J. Biol. Chem. (2001) [Pubmed]
  17. Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. Feng, R., Lu, Y., Bowman, L.L., Qian, Y., Castranova, V., Ding, M. J. Biol. Chem. (2005) [Pubmed]
  18. Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase. Hemmerle, H., Burger, H.J., Below, P., Schubert, G., Rippel, R., Schindler, P.W., Paulus, E., Herling, A.W. J. Med. Chem. (1997) [Pubmed]
  19. Inhibition of DNA methylation by caffeic acid and chlorogenic acid, two common catechol-containing coffee polyphenols. Lee, W.J., Zhu, B.T. Carcinogenesis (2006) [Pubmed]
  20. Tobacco constituents are mitogenic for arterial smooth-muscle cells. Becker, C.G., Hajjar, D.P., Hefton, J.M. Am. J. Pathol. (1985) [Pubmed]
  21. Chlorogenic Acid is absorbed in its intact form in the stomach of rats. Lafay, S., Gil-Izquierdo, A., Manach, C., Morand, C., Besson, C., Scalbert, A. J. Nutr. (2006) [Pubmed]
  22. Salivary uric acid at the acidic pH of the stomach is the principal defense against nitrite-derived reactive species: Sparing effects of chlorogenic acid and serum albumin. Pietraforte, D., Castelli, M., Metere, A., Scorza, G., Samoggia, P., Menditto, A., Minetti, M. Free Radic. Biol. Med. (2006) [Pubmed]
  23. Cytoprotective effects of heme oxygenase-1 induction by 3-O-caffeoyl-1-methylquinic acid. Kweon, M.H., Jung, M.J., Sung, H.C. Free Radic. Biol. Med. (2004) [Pubmed]
  24. Deviceless decoupled electrochemical detection of catecholamines in capillary electrophoresis using gold microband array electrodes. Klett, O., Nischang, I., Nyholm, L. Electrophoresis (2002) [Pubmed]
  25. Abnormal accumulation of sugars and phenolics in tobacco roots expressing the Agrobacterium T-6b oncogene and the role of these compounds in 6b-induced growth. Clément, B., Perot, J., Geoffroy, P., Legrand, M., Zon, J., Otten, L. Mol. Plant Microbe Interact. (2007) [Pubmed]
  26. CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway. Schoch, G., Goepfert, S., Morant, M., Hehn, A., Meyer, D., Ullmann, P., Werck-Reichhart, D. J. Biol. Chem. (2001) [Pubmed]
  27. Effects of blue honeysuckle (Lonicera caerulea L.) extract on lipopolysaccharide-induced inflammation in vitro and in vivo. Jin, X.H., Ohgami, K., Shiratori, K., Suzuki, Y., Koyama, Y., Yoshida, K., Ilieva, I., Tanaka, T., Onoe, K., Ohno, S. Exp. Eye Res. (2006) [Pubmed]
  28. Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide. Iwahashi, H., Nishizaki, K., Takagi, I. Biochem. J. (2002) [Pubmed]
  29. Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. Schwab, D., Herling, A.W., Hemmerle, H., Schubert, G., Hagenbuch, B., Burger, H.J. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  30. Chlorogenic acid and caffeic acid are absorbed in humans. Olthof, M.R., Hollman, P.C., Katan, M.B. J. Nutr. (2001) [Pubmed]
  31. Determination of chlorogenic acid in rat blood by microdialysis coupled with microbore liquid chromatography and its application to pharmacokinetic studies. Tsai, T.H., Chen, Y.F., Shum, A.Y., Chen, C.F. Journal of chromatography. A. (2000) [Pubmed]
  32. A comparative genotoxicity study of chlorogenic acid (3-0-caffeoylquinic acid). Stich, H.F., Rosin, M.P., Wu, C.H., Powrie, W.D. Mutat. Res. (1981) [Pubmed]
  33. Cholinomimetic compound distinct from caffeine contained in coffee. II: Muscarinic actions. Tse, S.Y. Journal of pharmaceutical sciences. (1992) [Pubmed]
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