Exploring nature profits: Development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 289-296

  Teixeira, José ^a   Silva, Tiago ^a   Benfeito, Sofia ^a   Gaspar, Alexandra ^a   Garrido, E Manuela ^a,b   Garrido, Jorge ^a,b   Borges, Fernanda ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b INSTITUTO SUPERIOR DE ENGENHARIA DO PORTO   (Portugal)

Author keywords

Antioxidant activity; Cinnamic acid; Drug like properties; Gallic acid; Hybrid antioxidants; Redox potential; SPAR

Indexed keywords

CAFFEIC ACID; CINNAMIC ACID; GALLIC ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; CORRELATION ANALYSIS; ELECTROCHEMISTRY; HUMAN; LIPOPHILICITY; MEMBRANE; OXIDATION REDUCTION POTENTIAL; PARTITION COEFFICIENT; SYNTHESIS;

ANTIOXIDANTS; CAFFEIC ACIDS; GALLIC ACID; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE;

EID: 84873030904     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.12.049     Document Type: Article

References (40)

1. B. Halliwell Antioxidants in human health and disease Annu. Rev. Nutr. 16 1996 33 50
2. B. Uttara, A.V. Singh, P. Zamboni, and R.T. Mahajan Oxidative stress and neurodegenerative diseases: a review of upstream and downstream antioxidant therapeutic options Curr. Neuropharmacol. 7 2009 65 74
3. B. Frank, and S. Gupta A review of antioxidants and Alzheimer's disease Ann. Clin. Psychiatr. 17 2005 269 286
4. P. Fresco, F. Borges, C. Diniz, and M.P. Marques New insights on the anticancer properties of dietary polyphenols Med. Res. Rev. 26 2006 747 766
5. S.C. Thomasset, D.P. Berry, G. Garcea, T. Marczylo, W.P. Steward, and A.J. Gescher Dietary polyphenolic phytochemicals-promising cancer chemopreventive agents in humans? A review of their clinical properties Int. J. Cancer 120 2007 451 458
6. S. Quideau, D. Deffieux, C. Douat-Casassus, and L. Pouysegu Plant polyphenols: chemical properties, biological activities, and synthesis Angew. Chem. Int. Ed. Engl. 50 2011 586 621
7. O.I. Aruoma, A. Murcia, J. Butler, and B. Halliwell Evaluation of the antioxidant and prooxidant actions of gallic acid and its derivatives J. Agric. Food Chem. 41 1993 1880 1885
8. P. Fresco, F. Borges, M.P. Marques, and C. Diniz The anticancer properties of dietary polyphenols and its relation with apoptosis Curr. Pharm. Des. 16 2010 114 134
9. C.A. Gomes, T.G. Girão Da Cruz, J.L. Andrade, N. Milhazes, F. Borges, and M.P.M. Marques Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study J. Med. Chem. 46 2003 5395 5401
10. S.M. Fiuza, C. Gomes, L.J. Teixeira, M.T. Girão Da Cruz, M.N.D.S. Cordeiro, N. Milhazes, F. Borges, and M.P.M. Marques Phenolic acid derivatives with potential anticancer properties-a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids Bioorg. Med. Chem. 12 2004 3581 3589
11. C. Siquet, F. Paiva-Martins, J.L. Lima, S. Reis, and F. Borges Antioxidant profile of dihydroxy- and trihydroxyphenolic acids-a structure-activity relationship study Free Radic. Res. 40 2006 433 442
12. J.C. Menezes, S.P. Kamat, J.A. Cavaleiro, A. Gaspar, J. Garrido, and F. Borges Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates Eur. J. Med. Chem. 46 2011 773 777
13. A. Gaspar, M. Martins, P. Silva, E.M. Garrido, J. Garrido, O. Firuzi, R. Miri, L. Saso, and F. Borges Dietary phenolic acids and derivatives. Evaluation of the antioxidant activity of sinapic acid and its alkyl esters J. Agric. Food Chem. 2010
14. M. Esteves, C. Siquet, A. Gaspar, V. Rio, J.B. Sousa, S. Reis, M.P. Marques, and F. Borges Antioxidant versus cytotoxic properties of hydroxycinnamic acid derivatives-a new paradigm in phenolic research Arch. Pharm. (Weinheim) 341 2008 164 173
15. N.F. Machado, R. Calheiros, S.M. Fiuza, F. Borges, A. Gaspar, J. Garrido, and M.P. Marques Phenolic esters with potential anticancer activity-the structural variable J. Mol. Model. 13 2007 865 877
16. F. Borges, J.L.F.C. Lima, I. Pinto, S. Reis, and C. Siquet Application of a potentiometric system with data-analysis computer programs to the quantification of metal-chelating activity of two natural antioxidants: caffeic acid and ferulic acid Helv. Chim. Acta 86 2003 3081 3087
17. J.H. Chen, and C.T. Ho Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds J. Agric. Food Chem. 45 1997 2374 2378
18. M.C. Figueroa-Espinoza, and P. Villeneuve Phenolic acids enzymatic lipophilization J. Agric. Food Chem. 53 2005 2779 2787
19. P. Cos, P. Rajan, I. Vedernikova, M. Calomme, L. Pieters, A.J. Vlietinck, K. Augustyns, A. Haemers, and D. Vanden Berghe In vitro antioxidant profile of phenolic acid derivatives Free Radic. Res. 36 2002 711 716
20. J. Vaya, P.A. Belinky, and M. Aviram Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation Free Radic. Biol. Med. 23 1997 302 313
21. S. Gao, and M. Hu Bioavailability challenges associated with development of anti-cancer phenolics Mini-Rev. Med. Chem. 10 2010 550 567
22. A. Crozier, I.B. Jaganath, and M.N. Clifford Dietary phenolics: chemistry, bioavailability and effects on health Nat. Prod. Rep. 26 2009 1001 1043
23. F.M. Roleira, C. Siquet, E. Orru, E.M. Garrido, J. Garrido, N. Milhazes, G. Podda, F. Paiva-Martins, S. Reis, R.A. Carvalho, E.J. Silva, and F. Borges Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties Bioorg. Med. Chem. 18 2010 5816 5825
24. J. Garrido, A. Gaspar, E.M. Garrido, R. Miri, M. Tavakkoli, S. Pourali, L. Saso, F. Borges, and O. Firuzi Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress Biochimie 94 2012 961 967
25. V.D. Kancheva, P.V. Boranova, J.T. Nechev, and I.I. Manolov Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants Biochimie 92 2010 1138 1146
26. J. Milde, E.F. Elstner, and J. Grassmann Synergistic effects of phenolics and carotenoids on human low-density lipoprotein oxidation Mol. Nutr. Food Res. 51 2007 956 961
27. F.A. Silva, F. Borges, C. Guimaraes, J.L. Lima, C. Matos, and S. Reis Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters J. Agric. Food Chem. 48 2000 2122 2126
28. R. Fumeaux, C. Menozzi-Smarrito, A. Stalmach, C. Munari, K. Kraehenbuehl, H. Steiling, A. Crozier, G. Williamson, and D. Barron First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption Org. Biomol. Chem. 8 2010 5199 5211
29. N. Sharma, U.K. Sharma, R. Kumar, N. Katoch, and A.K. Sinha First bovine serum albumin-promoted synthesis of enones, cinnamic acids and coumarins in ionic liquid: an insight into the role of protein impurities in porcine pancreas lipase for olefinic bond formation Adv. Synth. Catal. 353 2011 871 878
30. A. Gaspar, E.M. Garrido, M. Esteves, E. Quezada, N. Milhazes, J. Garrido, and F. Borges New insights into the antioxidant activity of hydroxycinnamic acids: synthesis and physicochemical characterization of novel halogenated derivatives Eur. J. Med. Chem. 44 2009 2092 2099
31. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans Antioxidant activity applying an improved ABTS radical cation decolorization assay Free Radic. Biol. Med. 26 1999 1231 1237
32. W. Brand-Williams, M.E. Cuvelier, and C. Berset Use of a free radical method to evaluate antioxidant activity LWT-Food Sci. Technol. 28 1995 25 30
33. B. Halliwell, and J.M. Gutteridge Free Radicals in Biology and Medicine 2007 Oxford University Press Oxford
34. C.A. Collins, F.H. Fry, A.L. Holme, A. Yiakouvaki, A. Al-Qenaei, C. Pourzand, and C. Jacob Towards multifunctional antioxidants: synthesis, electrochemistry, in vitro and cell culture evaluation of compounds with ligand/catalytic properties Org. Biomol. Chem. 3 2005 1541 1546
35. B. Yang, A. Kotani, K. Arai, and F. Kusu Relationship of electrochemical oxidation of catechins on their antioxidant activity in microsomal lipid peroxidation Chem. Pharm. Bull. (Tokyo) 49 2001 747 751
36. B. Reis, M. Martins, B. Barreto, N. Milhazes, E.M. Garrido, P. Silva, J. Garrido, and F. Borges Structure-property-activity relationship of phenolic acids and derivatives. Protocatechuic acid alkyl esters J. Agric. Food Chem. 58 2010 6986 6993
37. S. Gunckel, P. Santander, G. Cordano, J. Ferreira, S. Munoz, L.J. Nunez-Vergara, and J.A. Squella Antioxidant activity of gallates: an electrochemical study in aqueous media Chem. Biol. Interact 114 1998 45 59
38. R. Abdel-Hamid, and E.F. Newair Electrochemical behavior of antioxidants: I. Mechanistic study on electrochemical oxidation of gallic acid in aqueous solutions at glassy-carbon electrode J. Electroanal. Chem. 657 2011 107 112
39. J. Teixeira, P. Soares, S. Benfeito, A. Gaspar, J. Garrido, M.P. Murphy, and F. Borges Rational discovery and development of a mitochondria-targeted antioxidant based on cinnamic acid scaffold Free Radic. Res. 46 2012 600 611
40. S. Teixeira, C. Siquet, C. Alves, I. Boal, M.P. Marques, F. Borges, J.L. Lima, and S. Reis Structure-property studies on the antioxidant activity of flavonoids present in diet Free Radic. Biol. Med. 39 2005 1099 1108