Theoretical investigation on antioxidant activity of bromophenols from the marine red alga Rhodomela confervoides: H-atom vs electron transfer mechanism

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 7, 2013, Pages 1534-1541

  Javan, Ashkan Jebelli ^a   Javan, Marjan Jebeli ^b   Tehrani, Zahra Aliakbar ^b  

^a SEMNAN UNIVERSITY   (Iran)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

bond dissociation energy; bromophenol; DFT study; radical scavenging activity; Rhodomela confervoides

Indexed keywords

BOND DISSOCIATION ENERGIES; BROMOPHENOLS; DFT STUDY; RADICAL SCAVENGING ACTIVITY; RHODOMELA CONFERVOIDES;

AGENTS; BOND STRENGTH (CHEMICAL); ELECTRON TRANSPORT PROPERTIES; FREE RADICAL REACTIONS; IONIZATION POTENTIAL;

ELECTRON TRANSITIONS;

PHENOL DERIVATIVE; SCAVENGER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; ELECTRON TRANSPORT; PHYSIOLOGY; RED ALGA; THEORETICAL MODEL;

ELECTRON TRANSPORT; ELECTRONS; FREE RADICAL SCAVENGERS; MODELS, THEORETICAL; MOLECULAR STRUCTURE; PHENOLS; RHODOPHYTA;

EID: 84874051565     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf304926m     Document Type: Article

References (47)

1. Diplok, A. T. Free Radical Damage and its Control, New Comprehensive Biochemistry; Rice-Evans, C., Burdon, R. H. A., Eds.; Elsevier: Amsterdam, The Netherlands, 1994; pp 23-64.
2. Larson, R. A. Naturally Occurring Antioxidants; Lewis Publishers, CRC Press LLC.: Boca Raton, FL, 1997; pp 256-291.
3. Kamkar, A.; Jebelli Javan, A.; Asadi, F.; Kamalinejad, M. The antioxidative effect of Iranian Mentha pulegium extracts and essential oil in sunflower oil Food Chem. Toxicol. 2010, 48, 1796-1800
4. Zheng, W. S.; Wang, Y. Antioxidant activity and phenolic compounds in selected herbs J. Agric. Food. Chem. 2001, 49, 5165-5170
5. Jebelli Javan, A.; Ghazvinian, K.; Mahdavi, A.; Javaheri Vayeghan, A.; Steji, H.; Ghaffari Khaligh, S. The effect of dietary Zataria Multiflora Boiss essential oil supplementation on microbial growth and lipid peroxidation of Broiler Nreast fillets during refrigerated storage. J. Food Process. Preserv. 2012, in press.
6. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 1996, 20, 933-956
7. Ito, N.; Hirose, M.; Fukushima, S.; Tsuda, H.; Shirai, T.; Tatematsu, M. Studies on antioxidants: Their carcinogenic and modifying effects on chemical carcinogenesis Food Chem. Toxicol. 1986, 24, 1071-1082
8. Williams, G. M.; Iatropoulos, M. J.; Whysner, J. Safety assessment of butylated hydroxyanisole and butylated hydroxytoluene as antioxidant food additives J. Food Chem. Toxicol. 1999, 37, 1027-1038
9. Li, Y. X.; Li, Y.; Lee, S. H.; Qian, Z. J.; Kim, S. K. Inhibitors of oxidation and matrix metalloproteinases, floridoside, and d -isofloridoside from marine red alga Laurencia undulate J. Agric. Food Chem. 2010, 58, 578-586
10. Li, K.; Li, X. M.; Ji, N. Y.; Gloer, J. B.; Wang, B. G. Urceolatin, a structurally unique bromophenol from Polysiphonia urceolata Org. Lett. 2008, 10, 1429-1432
11. Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G. Natural bromophenols from the marine red alga Polysiphonia urceolata (Rhodomelaceae): Structural elucidation and DPPH radical-scavenging activity Bioorg. Med. Chem. 2007, 15, 6627-6631
12. Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G. Bromophenols from the marine red alga Polysiphonia urceolata with DPPH radical scavenging activity J. Nat. Prod. 2008, 71, 28-30
13. Duan, X. J.; Li, X. M.; Wang, B. G. Highly brominated mono and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity J. Nat. Prod. 2007, 70, 1210-1213
14. Kurihara, H.; Mitani, T.; Kawabata, J.; Takahashi, K. Two new bromophenols from the red alga Odonthalia corymbifera J. Nat. Prod. 1999, 62, 882-884
15. Kurata, K.; Taniguchii, K.; Takashima, K.; Hayashi, I.; Suzuki, M. Feeding-deterrent bromophenols from Odonthalia corymbifera Phytochemistry 1997, 45, 485-487
16. Wiemer, D. F.; Idler, D. D.; Fenical, W. V. New anti-inflammatory bromophenols from the caribbean marine red alga Yidalia obtusaloba Experientia 1991, 47, 851-853
17. Ma, M.; Zhao, J. L.; Wang, S. J.; Li, S.; Yang, Y. C.; Shi, J. G.; Fan, X.; He, L. Bromophenols coupled with nucleoside bases and brominated tetrahydroisoquinolines from the red alga Rhodomela confervoides J. Nat. Prod. 2007, 70, 337-341
18. Zhao, J.; Fan, X.; Wang, S.; Li, S.; Shang, S.; Yang, Y.; Xu, N.; Lu, Y.; Shi, J. Bromophenol derivatives from the red alga Rhodomela confervoides J. Nat. Prod. 2004, 67, 1032-1035
19. Li, K.; Li, X.; Gloer, J. B.; Wang, B. Isolation, characterization, and antioxidant activity of bromophenols of the marine red alga Rhodomela confervoides J. Agric. Food Chem. 2011, 59, 9916-9921
20. Wright, J. S.; Johnson, E. R.; Di Labio, G. A. Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants J. Am. Chem. Soc. 2001, 123, 1173-1183
21. Zhu, Q.; Zhang, X. M.; Fry, A. Bond dissociation energies of antioxidants Polym. Degrad. Stab. 1997, 57, 43-50
22. Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols J. Am. Chem. Soc. 1985, 107, 7053-7065
23. Lucarini, M.; Pedulli, G. F.; Cipollone, M. Bond dissociation enthalpy of alpha-tocopherol and other phenolic antioxidants J. Org. Chem. 1994, 59, 5063-5070
24. 3 bond dissociation energies in phenol and anisole J. Org. Chem. 1996, 61, 7904
25. Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Cabiddu, S.; Fattuoni, C. Bond dissociation energies of O-H bonds in substituted phenols from equilibration studies J. Org. Chem. 1996, 61, 9259-9263
26. Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. 5-Pyrimidinols: Novel chain-breaking antioxidants more effective than phenols J. Am. Chem. Soc. 2001, 123, 4625-4626
27. Valgimigli, L.; Brigati, G.; Pedulli, G. F.; DiLabio, G. A.; Mastragostino, M.; Arbizzani, C.; Pratt, D. A. The effect of ring nitrogen atoms on the homolytic reactivity of phenolic compounds: Understanding the radical-scavenging ability of 5-pyrimidinols Chem.-Eur. J. 2003, 9, 4997-5010
28. Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. 6-Amino-3-pyridinols: Towards diffusion-controlled chain-breaking antioxidants Angew. Chem., Int. Ed. 2003, 42, 4370-4373
29. Nenadis, N.; Zhang, H. Y.; Tsimidou, M. Z. Structure-antioxidant activity relationship of ferulic acid derivatives: Effect of carbon side chain characteristic groups J. Agric. Food Chem. 2003, 51, 1874-1879
30. Zhang, H. Y.; Sun, Y. M.; Wang, X. L. Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants Chem.-Eur. J. 2003, 9, 502-508
31. Ji, H. F.; Tang, G. Y.; Zhang, H. Y. A theoretical study on the structure-activity relationships of metabolites of folates as antioxidants and its implications for rational design of antioxidants Bioorg. Med. Chem. 2005, 13, 1031-1036
32. Foti, M. C.; Johnson, E. R.; Vinqvist, M. R.; Wright, J. S.; Barclay, L. R. C.; Ingold, K. U. Naphthalene diols: A new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals J. Org. Chem. 2002, 67, 5190-5196
33. Chen, W.; Song, J.; Guo, P.; Cao, W.; Bian, J. Exploring a possible way to synthesize novel better antioxidants based on vitamin E: A DFT study Bioorg. Med. Chem. Lett. 2006, 16, 5874-5877
34. Becke, A. D. Density functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5656
35. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
36. Spartan '06V102'; Wavefunction, Inc., Irvine, CA.
37. Reed, A. E.; Weinstock, R. B.; Weinhold, F. Natural population analysis J. Chem. Phys. 1985, 83, 735-747
38. Reed, A. E.; Weinhold, F. Natural localized molecular orbitals J. Chem. Phys. 1985, 83, 1736-1741
39. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 1988, 88, 899-926
40. Reed, A. E.; Schleye, P. R. Chemical bonding in hypervalent molecules. The dominance of ionic bonding and negative hyperconjugation over d-orbital participation J. Am. Chem. Soc. 1990, 112, 1434-1445
41. Fan, X.; Xu, N. J.; Shi, J. G. Bromophenols from the red alga Rhodomela confervoides J. Nat. Prod. 2003, 66, 455-458
42. Ma, M.; Zhao, J. L; Wang, S. J.; Li, S.; Yang, Y. C.; Shi, J. G.; Fan, X.; He, L. Bromophenols coupled with methyl γ-ureidobutyrate and bromophenol sulfates from the red alga Rhodomela confervoides J. Nat. Prod. 2006, 69, 206-210
43. Zhao, J.; Fan, X.; Wang, S.; Li, S.; Shang, S.; Yang, Y.; Xu, N.; Lu, Y.; Shi, J. Bromophenol derivatives from the red alga Rhodomela confervoides J. Nat. Prod. 2004, 67, 1032-1035
44. Kurata, K.; Taniguchii, K.; Takashima, K.; Hayashi, I.; Suzuki, M. Feeding-deterrent bromophenols from Odonthalia corymbifera Phytochemistry 1997, 45, 485-487
45. Katsui, N.; Suzuki, Y.; Kitamura, S.; Irie, T. 5,6- Dibromoprotocatechualdehyde and 2,3-dibromo-4,5-dihydroxybenzyl methyl ether: New dibromophenols from Rhodomela larix Tetrahedron 1967, 23, 1185-1188
46. Lee, J. H.; Lee, T. K.; Kang, R. S.; Shin, H. J.; Lee, H. S. The in vitro antioxidant activities of the bromophenols from the red alga Tichocarpus crinitus and phenolic derivatives J. Korean Magn. Reson. Soc. 2007, 11, 56-63
47. Chaillou, L. L.; Nazareno, M. A. New method to determine antioxidant activity of polyphenols J. Agric. Food Chem. 2006, 54, 8397-8402