Antioxidant phenolic esters with potential anticancer activity: A Raman spectroscopy study

Journal of Raman Spectroscopy

Volumn 39, Issue 1, 2008, Pages 95-107

  Calheiros, R ^a   Machado, N F L ^a   Fiuza, S M ^a   Gaspar, A ^a   Garrido, J ^a,b   Milhazes, N ^a,c   Borges, F ^a,d   Marques, M P M ^a,e  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b INSTITUTO SUPERIOR DE ENGENHARIA DO PORTO   (Portugal)

^c UNIVERSITY INSTITUTE OF HEALTH SCIENCES IUCS   (Portugal)

^d UNIVERSITY OF PORTO   (Portugal)

^e UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Anticancer; Caffeates; Ferulates; Gallates; Phenolic esters; Raman spectroscopy

Indexed keywords

ANTIOXIDANTS; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; RAMAN SPECTROSCOPY; SPECTROSCOPIC ANALYSIS;

ANTICANCER; ANTICANCER ACTIVITIES; ANTICANCER PROPERTIES; ANTIOXIDANT PROPERTIES; CAFFEATE; FERULATES; GALLATE; PHENOLIC ESTERS; RAMAN STUDIES; RING SUBSTITUENTS;

ESTERS;

EID: 38549148538     PISSN: 03770486     EISSN: 10974555     Source Type: Journal    
DOI: 10.1002/jrs.1822     Document Type: Article

References (56)

1. Natella F, Nardini M, Di Felice M, Scaccini C. J. Agric. Food Chem. 1999; 47: 1453.
2. Mattila P, Hellstrom J, Torronen R. J.Agric.Food Chem. 2006; 54: 7193.
3. Lin J-Y, Tang C-Y. Food Chem. 2007; 101: 140.
4. Podsdek A. Food Sci. Technol. 2007; 40: 1.
5. Teixeira S, Siquet C, Alves C, Boal I, Marques MPM, Borges F, Lima JLFC, Reis S. Free Radic. Biol. Med. 2005; 39: 1099.
6. Lee Y-T, Don M-J, Liao C-H, Chiou H-W, Chen C-F, Ho L-K. Clin. Chim. Acta 2005; 352: 135.
7. Suzuki A, Yamamoto N, Jokura H, Yamamoto M, Fujii A, Tokimitsu I, Saito I. J. Hypertens. 2006; 6: 1065.
8. Khanduja KL, Avti PK, Kumar S, Mittal N, Sohi KK, Pathak CM. Biochim. Biophys. Acta 2006; 283: 1760.
9. Siquet C, Paiva-Martins F, Milhazes N, Lima JLFC, Reis S, Borges F. Free Radic. Res. 2006; 40: 433.
10. Cárdenas M, Marder M, Blank VC, Roguin LP. Bioorg. Med. Chem. 2006; 14: 2966.
11. Fresco P, Borges F, Diniz C, Marques MPM. Med. Res. Rev. 2006; 26: 747.
12. Ferguson PJ, Kurowska E, Feeman DJ, Chambers AF, Koropatnick DJ. J. Nutr. 2004; 134: 1529.
13. Wenzel U, Herzog A, Kuntz S, Daniel H. Proteomics 2004; 4: 2160.
14. Yoshimizu N, Otani Y, Saikawa Y, Kubota T, Yoshida M, Furukawa T, Kumai K, Kameyama K, Fujii M, Yano M, Sato T, Ito A, Kitajima M. Aliment. Pharmacol. Ther. 2004; 20: 95.
15. Kintzios S. Crit. Rev. Plant Sci. 2006; 25: 79.
16. Kelloff GJ. Adv. Cancer Res. 2000; 78: 199.
17. Manach C, Sealbert A, Morand C, Rémésy C, Jiménez L. Am. J. Clin. Nutr. 2004; 79: 727.
18. Sousa JB, Calheiros R, Rio V, Borges F, Marques MPM. J. Mol. Struct. 2006; 783: 135.
19. Chung WY, Jung YJ, Surh YJ, Lee SS, Park KK. Mutat. Res. 2001; 496: 199.
20. Krasowska A, Stasiuk M, Oswiecimska M, Kozubek A, Bien M, Witek S, Sigler K. Z. Naturforsch. 2001; 56: 878.
21. Silva FAM, Borges F, Ferreira M. J. Agric. Food Chem. 2001; 49: 3936.
22. Gomes CA, Girãda Cruz T, Andrade JL, Milhazes N, Borges F, Marques MPM. J. Med. Chem. 2003; 46: 5395.
23. Fiuza SM, Van Besien E, Milhazes N, Borges F, Marques MPM. Bioorg. Med. Chem. 2004; 12: 3581.
24. Chung TW, Moon SK, Chang YC, Ko JH, Lee YC, Ch G, Kim JG, Kim CH. FASEB J. 2004; 18: 1670.
25. Marques MPM, Borges F, Sousa JB, Calheiros R, Garrido J, Gaspar A, Antunes F, Diniz C, Fresco P. Lett. Drug Des. Discov. 2006; 3: 316.
26. Graf E. Free Radic. Biol. Med. 1992; 13: 435.
27. Mathew S, Abraham TE. Crit. Rev. Biotechnol. 2004; 24: 59.
28. Wang BH, Ou-Yang JP. Cardiovasc. Drug Rev. 2005; 23: 161.
29. Van Besien E, Marques MPM. THEOCHEM 2003; 625: 265.
30. Fiuza SM, Van Besien E, Milhazes N, Borges F, Marques MPM. J. Mol. Struct. 2004; 693: 103.
31. Machado NFL, Calheiros R, Fiuza SM, Borges F, Gaspar A, Garrido J, Marques MPM. J. Mol. Model. 2007; 13: 865.
32. Borges MFM, Pinto MMM. J. Liq. Chromatogr. 1994; 17: 1125.
33. Silva FAM, Borges F, Guimarães C, Lima JLFC, Matos C, Reis S. J. Agric. Food Chem. 2000; 48: 2122.
34. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr., Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision B. 04. Gaussian: Pittsburgh, 2003.
35. Lee C, Yang W, Parr RG. Phys. Rev. 1988; B37: 785.
36. Miehlich B, Savin A, Stoll H, Preuss H. Chem. Phys. Lett. 1989; 157: 200.
37. Becke AJ. Phys. Rev. 1988; A38: 3098.
38. Becke AJ. J. Chem. Phys. 1993; 98: 5648.
39. Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J. J. Chem. Phys. 1988; 89: 2193.
40. Peng C, Ayala PY, Schlegel HB, Frisch MJ. J. Comput. Chem. 1996; 17: 49.
41. Scott AP, Radom L. J. Phys. Chem. 1996; 100: 16502.
42. Batista de Carvalho LAE, Marques MPM, Teixeira-Dias JJC. J. Chem. Soc., Perkin Trans. 1999; 2: 2507.
43. Vueba ML, Pina ME, Veiga F, Sousa JJ, Batista de Carvalho LAE. Int. J. Pharm. 2006; 307: 56.
44. Wilson EB Jr. Phys. Rev. 1934; 45: 706.
45. Varsáyi G. Assignments for Vibrational Spectra of Seven Hundred Benzene Derivates. Akdémiai Kiadó, Budapest/Adam Hilger Limited: London, 1974.
46. Steiner T. Angew. Chem. Int. Ed. 2002; 41: 48.
47. Ribeiro-Claro PJA, Batista de Carvalho LAE, Amado AM. J. Raman Spectrosc. 1997; 28: 867.
48. Kiss JT, Felfoldi K, Kortvelyesi T, Palinko L. Vib. Spectrosc. 2000; 22: 63.
49. Sánchez-Cortés S, García-Ramos JV. Spectrochim. Acta 1999; A55: 2935.
50. Sánchez-Cortés S, García-Ramos JV. Appl. Spectrosc. 2000; 54: 230.
51. Sánchez-Cortés S, García-Ramos JV. J. Colloid Interface Sci. 2000; 231: 98.
52. Bell EJ, Burns DT, Dennis AC, Matchett LJ, Speers JS. The Analyst 2000; 125: 1811.
53. Sägmüller B, Schwarze B, Brehm G, Schneider S. The Analyst 2001; 126: 2066.
54. Faulds K, Smith WE, Graham D, Lacey RJ. The Analyst 2002; 127: 282.
55. Milhazes N, Borges F, Calheiros R, Marques MPM. The Analyst 2004; 129: 1106.
56. Milhazes N, Calheiros R, Marques MPM, Garrido J, Natália M, Cordeiro DS, Rodrigues C, Quinteira S, Novais C, Peixe L, Borges F. Bioorg. Med. Chem. 2006; 14: 4078.