Caffeic acid derivatives, analogs and applications: a patent review (2009 – 2013)

Bibliography

• Razzaghi N, Garrido J, Khazraei H, et al. Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships. Curr Med Chem 2013;20:4436-50
   PubMedGoogle Scholar
• D’Archivio M, Filesi C, Di Benedetto R, et al. Polyphenols, dietary sources and bioavailability. Ann Ist Super Sanita 2007;43:348-61
   PubMedGoogle Scholar
• Russell WR, Labat A, Scobbie L, et al. Phenolic acid content of fruits commonly consumed and locally produced in Scotland. Food Chem 2009;113:100-4
   Google Scholar
• Mattila P, Hellström J. Phenolic acids in potatoes, vegetables, and some of their products. J Food Comp Anal 2007;20:152-60
   Web of Science ®Google Scholar
• Benfeito S, Oliveira C, Soares P, et al. Antioxidant therapy: still in search of the ’magic bullet’. Mitochondrion 2013;13:427-35
   PubMed Web of Science ®Google Scholar
• Upadhyay R, Mohan Rao LJ. An outlook on chlorogenic acids-occurrence, chemistry, technology, and biological activities. Crit Rev Food Sci Nutr 2013;53:968-84
   PubMed Web of Science ®Google Scholar
• Konishi Y, Kobayashi S. Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers. J Agric Food Chem 2004;52:2518-26
   PubMed Web of Science ®Google Scholar
• Konishi Y, Hitomi Y, Yoshioka E. Intestinal absorption of p-coumaric and gallic acids in rats after oral administration. J Agric Food Chem 2004;52:2527-32
   PubMed Web of Science ®Google Scholar
• Konishi Y, Kobayashi S, Shimizu M. Transepithelial transport of p-coumaric acid and gallic acid in Caco-2 cell monolayers. Biosci Biotechnol Biochem 2003;67:2317-24
   PubMed Web of Science ®Google Scholar
• Lafay S, Morand C, Manach C, et al. Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Br J Nutr 2006;96:39-46
   PubMed Web of Science ®Google Scholar
• El-Seedi HR, El-Said AM, Khalifa SA, et al. Biosynthesis, natural sources, dietary intake, pharmacokinetic properties, and biological activities of hydroxycinnamic acids. J Agric Food Chem 2012;60:10877-95
   PubMed Web of Science ®Google Scholar
• Ito H, Gonthier MP, Manach C, et al. Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr 2005;94:500-9
   PubMed Web of Science ®Google Scholar
• Silva FA, Borges F, Guimaraes C, et al. Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J Agric Food Chem 2000;48:2122-6
   PubMed Web of Science ®Google Scholar
• Sroka Z, Cisowski W. Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem Toxicol 2003;41:753-8
   PubMed Web of Science ®Google Scholar
• Borges F, Guimaraes C, Lima JL, et al. Potentiometric studies on the complexation of copper(II) by phenolic acids as discrete ligand models of humic substances. Talanta 2005;66:670-3
   PubMedGoogle Scholar
• Zhang M, Zhou J, Wang L, et al. Caffeic acid reduces cutaneous tumor necrosis factor alpha (TNF-alpha), IL-6 and IL-1beta levels and ameliorates skin edema in acute and chronic model of cutaneous inflammation in mice. Biol Pharm Bull 2014;37:347-54
   PubMed Web of Science ®Google Scholar
• Gopalakrishnan A, Tony Kong AN. Anticarcinogenesis by dietary phytochemicals: cytoprotection by Nrf2 in normal cells and cytotoxicity by modulation of transcription factors NF-kappa B and AP-1 in abnormal cancer cells. Food Chem Toxicol 2008;46:1257-70
   PubMed Web of Science ®Google Scholar
• Yeh CT, Ching LC, Yen GC. Inducing gene expression of cardiac antioxidant enzymes by dietary phenolic acids in rats. J Nutr Biochem 2009;20:163-71
   PubMed Web of Science ®Google Scholar
• Landete JM. Updated knowledge about polyphenols: functions, bioavailability, metabolism, and health. Crit Rev Food Sci Nutr 2012;52:936-48
   PubMed Web of Science ®Google Scholar
• Scalbert A, Manach C, Morand C, et al. Dietary polyphenols and the prevention of diseases. Crit Rev Food Sci Nutr 2005;45:287-306
   PubMed Web of Science ®Google Scholar
• Visioli F, De La Lastra CA, Andres-Lacueva C, et al. Polyphenols and human health: a prospectus. Crit Rev Food Sci Nutr 2011;51:524-46
   PubMed Web of Science ®Google Scholar
• Touaibia M, Jean-Francois J, Doiron J. Caffeic Acid, a versatile pharmacophore: an overview. Mini Rev Med Chem 2011;11:695-713
   PubMed Web of Science ®Google Scholar
• Desay UR, Henry BL, Liang A, et al. Cinnamic acid-based oligomers and uses thereof. US20120027691A1; 2013
   Google Scholar
• Liu J, Du Y. Caffeic acid derivatives and their use in improving neuronal cell viability. WO2012068038A2; 2012
   Google Scholar
• Csermely P, Agoston V, Pongor S. The efficiency of multi-target drugs: the network approach might help drug design. Trends Pharmacol Sci 2005;26:178-82
   PubMed Web of Science ®Google Scholar
• Geldenhuys WJ, Van der Schyf CJ. Rationally designed multi-targeted agents against neurodegenerative diseases. Curr Med Chem 2013;20:1662-72
   PubMed Web of Science ®Google Scholar
• Aprile G, Macerelli M, Giuliani F. Regorafenib for gastrointestinal malignancies : from preclinical data to clinical results of a novel multi-target inhibitor. BioDrugs 2013;27:213-24
   PubMedGoogle Scholar
• Youdim MB, Oh YJ. Promise of neurorestoration and mitochondrial biogenesis in Parkinson’s Disease with multi target drugs: an alternative to stem cell therapy. Exp Neurobiol 2013;22:167-72
   PubMedGoogle Scholar
• Rennie RP. Current and future challenges in the development of antimicrobial agents. Handb Exp Pharmacol 2012(211):45-65
   PubMedGoogle Scholar
• Andrae-Marobela K, Ghislain FW, Okatch H, et al. Polyphenols: a diverse class of multi-target anti-HIV-1 agents. Curr Drug Metab 2013;14:392-413
   PubMedGoogle Scholar
• Baz M, Abed Y, Papenburg J, et al. Emergence of oseltamivir-resistant pandemic H1N1 virus during prophylaxis. N Engl J Med 2009;361:2296-7
   PubMed Web of Science ®Google Scholar
• Wong CH, Fang JM, Liu KC, et al. Enhanced anti-influenza agents conjugated with anti-inflammatory activity. WO2013155375A1; 2013
   Google Scholar
• Thefaceshop Korea Co., Ltd. Caffeic acid derivative and composition containing the same. EP0339671B1; 2010
   Google Scholar
• Okombi S, Rival D, Boumendjel A, et al. Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions. US20070183996A1; 2013
   Google Scholar
• Lee YS, Kwak SY, Seo HS, et al. Derivative of hydroxycinnamic acid in which a peptide has been bonded, production method for same, and cosmetic composition comprising the same. WO2011014025A2, WO2011014025A3; 2011
   Google Scholar
• Kwak SY, Yang JK, Choi HR, et al. Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant. Bioorg Med Chem Lett 2013;23:1136-42
   PubMed Web of Science ®Google Scholar
• Kwak SY, Lee S, Yang JK. Antioxidative activities of caffeoyl-proline dipeptides. Food Chem 2012;130:847-52
   Web of Science ®Google Scholar
• Kwak SY, Lee S, Choi HR. Dual effects of caffeoyl-amino acidyl-hydroxamic acid as an antioxidant and depigmenting agent. Bioorg Med Chem Lett 2011;21:5155-88
   PubMedGoogle Scholar
• Seo HS, Kwak SY, Lee YS. Antioxidative Activities of Histidine Containing Caffeic acid-dipeptides. Bioorg Med Chem Lett 2010;20:4266-72
   PubMed Web of Science ®Google Scholar
• Scarpati ML, Oriente G. Chicoric acid (dicaffeyltartic acid): its isolation from chicory (Chicorium intybus) and synthesis. Tetrahedron 1958;4:43-8
   Google Scholar
• Park CM, Jin KS, Lee YW, et al. Luteolin and chicoric acid synergistically inhibited inflammatory responses via inactivation of PI3K-Akt pathway and impairment of NF-kappaB translocation in LPS stimulated RAW 264.7 cells. Eur J Pharmacol 2011;660:454-9
   PubMed Web of Science ®Google Scholar
• Reinke RA, Lee DJ, McDougall BR, et al. L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology 2004;326:203-19
   PubMedGoogle Scholar
• Azay-Milhau J, Ferrare K, Leroy J, et al. Antihyperglycemic effect of a natural chicoric acid extract of chicory (Cichorium intybus L.): a comparative in vitro study with the effects of caffeic and ferulic acids. J Ethnopharmacol 2013;150:755-60
   PubMed Web of Science ®Google Scholar
• Muthusamy VS, Saravanababu C, Ramanathan M, et al. Inhibition of protein tyrosine phosphatase 1B and regulation of insulin signalling markers by caffeoyl derivatives of chicory (Cichorium intybus) salad leaves. Br J Nutr 2010;104:813-23
   PubMed Web of Science ®Google Scholar
• Tousch D, Lajoix AD, Hosy E, et al. Chicoric acid, a new compound able to enhance insulin release and glucose uptake. Biochem Biophys Res Commun 2008;377:131-5
   PubMed Web of Science ®Google Scholar
• Andary C. Anti-diabetes composition containing chicoric acid and/or one of the metabolites thereof. US8404746B2; 2013
   Google Scholar
• Aybar MJ, Sanchez Riera AN, Grau A, et al. Hypoglycemic effect of the water extract of Smallantus sonchifolius (yacon) leaves in normal and diabetic rats. J Ethnopharmacol 2001;74:125-32
   PubMed Web of Science ®Google Scholar
• Takenaka M, Yan X, Ono H, et al. Caffeic acid derivatives in the roots of yacon (Smallanthus sonchifolius). J Agric Food Chem 2003;51:793-6
   PubMed Web of Science ®Google Scholar
• Terada S, Itoh K, Noguchi N, et al. Functional food containing sodium tricaffeoylaldarate. US8372890B2; 2013
   Google Scholar
• Terada S, Ito K, Taka M, et al. alpha-Glucosidase inhibitory active components and glucose level lowering effect of yacon aerial part extract. Nat Med 2003;57:89-94
   Google Scholar
• Wagh VD. Propolis: a wonder bees product and its pharmacological potentials. Adv Pharmacol Sci 2013;2013:308249
   PubMedGoogle Scholar
• Abdel-Latif MM, Windle HJ, Homasany BS, et al. Caffeic acid phenethyl ester modulates Helicobacter pylori-induced nuclear factor-kappa B and activator protein-1 expression in gastric epithelial cells. Br J Pharmacol 2005;146:1139-47
   PubMed Web of Science ®Google Scholar
• Shen H, Yamashita A, Nakakoshi M, et al. Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus. PLoS One 2013;8:e82299
   PubMed Web of Science ®Google Scholar
• Bai H, Liu R, Chen HL, et al. Enhanced antioxidant effect of caffeic acid phenethyl ester and trolox in combination against radiation induced-oxidative stress. Chem Biol Interact 2014;207:7-15
   PubMed Web of Science ®Google Scholar
• Hassan NA, El-Bassossy HM, Mahmoud MF, et al. Caffeic acid phenethyl ester, a 5-lipoxygenase enzyme inhibitor, alleviates diabetic atherosclerotic manifestations: effect on vascular reactivity and stiffness. Chem Biol Interact 2014;213:28-36
   PubMedGoogle Scholar
• Zhao WX, Wang L, Yang JL, et al. Caffeic acid phenethyl ester attenuates pro-inflammatory and fibrogenic phenotypes of LPS-stimulated hepatic stellate cells through the inhibition of NF-kappaB signaling. Int J Mol Med 2014;33:687-94
   PubMedGoogle Scholar
• Nam JH, Shin DH, Zheng H, et al. Inhibition of store-operated Ca2+ entry channels and K+ channels by caffeic acid phenethylester in T lymphocytes. Eur J Pharmacol 2009;612:153-60
   PubMedGoogle Scholar
• Omene C, Kalac M, Wu J, et al. Propolis and its active component, caffeic acid phenethyl ester (CAPE), modulate breast cancer therapeutic targets via an epigenetically mediated mechanism of action. J Cancer Sci Ther 2013;5:334-42
   PubMedGoogle Scholar
• Wu J, Omene C, Karkoszka J, et al. Caffeic acid phenethyl ester (CAPE), derived from a honeybee product propolis, exhibits a diversity of anti-tumor effects in pre-clinical models of human breast cancer. Cancer Lett 2011;308:43-53
   PubMed Web of Science ®Google Scholar
• Omene C, O’Connor O, Frenkel K. Propolis and caffeic acid phenethyl ester and uses thereof. WO2013012477A1; 2013
   Google Scholar
• Iwamoto M, Friedman EJ, Sandhu P, et al. Clinical pharmacology profile of vorinostat, a histone deacetylase inhibitor. Cancer Chemother Pharmacol 2013;72:493-508
   PubMed Web of Science ®Google Scholar
• Sova M. Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini Rev Med Chem 2012;12:749-67
   PubMed Web of Science ®Google Scholar
• De P, De K, Veau D, et al. Recent advances in the development of cinnamic-like derivatives as antituberculosis agents. Exp Opin Ther Pat 2012;22:155-68
   PubMed Web of Science ®Google Scholar
• De P, Baltas M, Bedos-Belval F. Cinnamic acid derivatives as anticancer agents-a review. Curr Med Chem 2011;18:1672-703
   PubMed Web of Science ®Google Scholar
• Teixeira J, Gaspar A, Garrido EM, et al. Hydroxycinnamic acid antioxidants: an electrochemical overview. BioMed Res Int 2013;2013:251754
   PubMedGoogle Scholar
• Teixeira J, Silva T, Andrade PB, et al. Alzheimer’s disease and antioxidant therapy: how long how far? Curr Med Chem 2013;20:2939-52
   PubMed Web of Science ®Google Scholar
• Benfeito S, Oliveira C, Soares P, et al. Antioxidant therapy: still in search of the ’magic bullet’. Mitochondrion 2013;13:427-35
   PubMed Web of Science ®Google Scholar
• Teixeira J, Silva T, Benfeito S, et al. Exploring nature profits: development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids. Eur J Med Chem 2013;62:289-96
   PubMed Web of Science ®Google Scholar
• Razzaghi-Asl N, Garrido J, Khazraei H, et al. Antioxidant properties of hydroxycinnamic acids: a review of structure- activity relationships. Curr Med Chem 2013;20(36):4436-50
   PubMed Web of Science ®Google Scholar
• Bolognesi ML. Polypharmacology in a single drug: multitarget drugs. Curr Med Chem 2013;20:1639-45
   PubMed Web of Science ®Google Scholar
• Chen Z, Han L, Xu M, et al. Rationally designed multitarget anticancer agents. Curr Med Chem 2013;20:1694-714
   PubMed Web of Science ®Google Scholar
• Chegaev K, Riganti C, Rolando B, et al. Doxorubicin-antioxidant co-drugs. Bioorg Med Chem Lett 2013;23:5307-10
   PubMed Web of Science ®Google Scholar
• Chao X, He X, Yang Y, et al. Design, synthesis and pharmacological evaluation of novel tacrine-caffeic acid hybrids as multi-targeted compounds against Alzheimer’s disease. Bioorg Med Chem Lett 2012;22:6498-502
   PubMed Web of Science ®Google Scholar
• Chen X, Decker M. Multi-target compounds acting in the central nervous system designed from natural products. Curr Med Chem 2013;20:1673-85
   PubMed Web of Science ®Google Scholar