Spectroscopic properties of quercetin derivatives, quercetin-3-O-rhamnoside and quercetin-3-O-rutinoside, in hydro-organic mixed solvents

Photochemistry and Photobiology

Volumn 85, Issue 4, 2009, Pages 934-942

  Liu, Hai Bo ^a   Yu, Daun ^a   Shin, Sung Chul ^a   Park, Hyoung Ryun ^b   Park, Jong Keun ^a   Bark, Ki Min ^a  

^a Gyeongsang National University   (South Korea)

^b Chonnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; QUERCETIN; SOLVENT;

ARTICLE; CHEMISTRY; METHODOLOGY; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

QUERCETIN; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 67650945228     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2009.00550.x     Document Type: Article

References (43)

1. Hertog, M. G. L., P. C. H. Hollman B. van de Putte (1993) Content of potentially anticarcinogenic flavonoids of tea infusions, wines and fruit juices. J. Agric. Food. Chem. 41, 1242 1246.
2. Iwashina, T. (2000) The structure and distribution of the flavonoids in plants. J. Plant. Res. 113, 287 299.
3. Rice-Evans, C. A., N. J. Miller, P. G. Bolwell, P. M. Bramley J. B. Pridham (1994) The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radic. Res. 22, 375 383.
4. Arai, Y., S. Watanabe, M. Kimira, K. Shimoi, R. Mochizuki N. Kinae (2000) Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration. J. Nutr. 130, 2243 2250. (Pubitemid 30682743)
5. Tikkanen, M. J. H. Adlercreutz (2000) Dietary soy-derived is oflavone phytoestrogens - Could they have a role in coronary heart disease prevention? Biochem. Pharmacol. 60, 1 5. (Pubitemid 30243079)
6. Han, K. K., J. M. Soares, M. A. Haidar, G. R. de Lima F. C. Baracat (2002) Benefits of soy isoflavone therapeutic regimen on menopausal symptoms. Obstet. Gynecol. (N. Y.) 99, 389 394. (Pubitemid 34188398)
7. Mercedes, J. G. C. Francisco (1999) Oxidation of the flavonol quercetin by polyphenol oxidase. J. Agric. Food. Chem. 47, 56 60.
8. Rothwell, J. A., A. J. Day M. R. A. Morgan (2005) Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J. Agric. Food. Chem. 53, 4355 4360. (Pubitemid 40855457)
9. Cornard, J. P., A. C. Boudet J. C. Merlin (1999) Theoretical investigation of the molecular structure of the isoquercitrin molecule. J. Mol. Struct. 508, 37 49. (Pubitemid 29444681)
10. Smith, G. J., S. J. Thomsen, K. R. Markham, C. Andary D. Cardon (2000) The photostabilities of naturally occurring 5-hydroxyflavones, flavonols, their glycosides and their aluminium complexes. J. Photochem. Photobiol. 136, 87 91.
11. Smith, G. J. K. R. Markham (1998) Tautomerism of flavonol glucosides: Relevance to plant UV protection and flower colour. J. Photochem. Photobiol. 118, 99 105. (Pubitemid 128346936)
12. Liu, W. G. Rong (2006) Interaction of flavonoid, quercetin with organized molecular assemblies of nonionic surfactant. Colloids Surf. A Physiochem. 274, 192 199. (Pubitemid 43129431)
13. Russo, N., M. Toscano N. Uccella (2000) Semiempirical molecular modeling into quercetin reactive site: Structural, conformational, and electronic features. J. Agric. Food. Chem. 48, 3232 3237. (Pubitemid 30681021)
14. Jovanovic, S. V., S. Steenken, M. Tosic, B. Marjanovic M. G. Simic (1994) Flavonoids as antioxidants. J. Am. Chem. Soc. 116, 4846 4851. (Pubitemid 24255827)
15. Zare, H. R., M. Namazian N. Nasirizadeh (2005) Electrochemical behavior of quercetin: Experimental and theoretical studies. J. Electroanal. Chem. 584, 77 83. (Pubitemid 41394181)
16. Baranac, J. M., N. A. Petranović M. M. D. Jasmina (1997) Spectrophotometric study of anthocyan copigmentation reactions. 2. Malvin and the nonglycosidized flavone quercetin. J. Agric. Food. Chem. 45, 1694 1697. (Pubitemid 127485605)
17. Torreggiani, A., M. Tamba, A. Trinchero S. Bonora (2005) Copper(II)-quercetin complexes in aqueous solutions: Spectroscopic and kinetic properties. J. Mol. Struct. 744-747, 759 766. (Pubitemid 40717437)
18. Rossi, M., L. F. Rickles W. A. Halpin (1986) The crystal and molecular structure of quercetin: A biologically active and naturally occurring flavonoid. Bioorg. Chem. 14, 55 69. (Pubitemid 16124326)
19. Erkoc, S., F. Erkoc N. Keskin (2003) Theoretical investigation of quercetin and its radical isomers. J. Mol. Struct. 631, 141 146.
20. Falkovskaia, E., P. K. Sengupta M. Kasha (1998) Photophysical induction of dual fluorescence of quercetin and related hydroxyflavones upon intermolecular H-bonding to solvent matrix. Chem. Phys. Lett. 297, 109 114. (Pubitemid 128340744)
21. Zhang, J. F. V. Bright (1991) Nanosecond reorganization of water within the interior of reverse micelles revealed by frequency-domain fluorescence spectroscopy. J. Phys. Chem. 95, 7900 7907.
22. Karukstis, K. K., A. A. Frazier, D. S. Martula J. A. Whiles (1996) Characterization of the microenvironments in AOT reversed micelles using multidimensional spectral analysis. J. Phys. Chem. 100, 11133 11138. (Pubitemid 126788833)
23. Park, H. R., H. C. Lee, T. H. Kim, J. K. Lee, K. Yang K. M. Bark (2000) Spectroscopic properties of fluoroquinolone antibiotics and nanosecond solvation dynamics in aerosol-OT reverse micelles. Photochem. Photobiol. 71 (3 281 293.
24. Barbosa, J., R. Bergés, I. Toro V. Sanz-Nebot (1997) Dissociation constants and preferential solvation of fluoroquinolones in hydro-organic mixtures used in LC. Int. J. Pharm. 149, 213 225. (Pubitemid 27193407)
25. Barbosa, J., I. Fonrodona, V. Marqués, V. Sanz-Nebot I. Toro (1997) Solvent effects on protonation equilibria of peptides and quinolones by factor analysis applied to the correlation between dissociation constants and solvatochromic parameters in acetonitrile-water mixtures. Anal. Chim. Acta 351, 397 405. (Pubitemid 27512486)
26. Barbosa, J., R. Bergés, I. Toro V. Sanz-Nebot (1997) Protonation equilibria of quinolone antibacterials in acetonitrile-water mobile phases used in LC. Talanta 44, 1271 1283. (Pubitemid 27249309)
27. Bilski, P., L. J. Martinez, E. B. Koker C. F. Chignell (1998) Influence of solvent polarity and proticity on the photochemical properties of norfloxacin. Photochem. Photobiol. 68 (1 20 24. (Pubitemid 128472327)
28. Park, H. R., C. H. Oh, H. C. Lee, S. R. Lim, K. Yang K. M. Bark (2004) Spectroscopic properties of various quinolone antibiotics in aqueous-organic solvent mixtures. Photochem. Photobiol. 80 (8 554 564. (Pubitemid 40174485)
29. Park, H. R., C. H. Oh, H. C. Lee, J. K. Lee, K. Yang K. M. Bark (2002) Spectroscopic properties of fluoroquinolone antibiotics in water-methanol and water-acetonitrile mixed solvents. Photochem. Photobiol. 75 (3 237 248.
30. Park, H. J., H. S. Young, K. Y. Park S. H. Rhee (1991) Flavonoids from the whole plants of Orostachys japonicus. Arch. Pharm. Res. 14, 167 171.
31. Jang, S. H., S. G. Lee, J. H. Kang, J. C. Park S. C. Shin (2006) Determination of phenolic acids and flavonol aglycone constants in Orostachys japonicus A. Berger grown under various cultivation conditions. Korean J. Med. Crop Sci. 14 (5 311 316.
32. Lahiri, S. C. S. Aditya (1974) Measurement of hydrogen ion concentration in mixed solvents. J. Indian Chem. Soc. 51 (1 319 323.
33. Barbosa, J., S. Hernández-Cassou, V. Sanz-Nebot I. Toro (1997) Variation of acidity constants of peptides in acetonitrile-water mixtures with solvent composition: Effect of preferential salvation. J. Pept. Res. 50 (1 14 24. (Pubitemid 27345444)
34. Reichardt, C. (1988) Solvents and Solvent Effects in Organic Chemistry, pp. 372 384. VCH, Weinheim, Germany.
35. O'Conner, D. V., W. R. Ware J. C. Andre (1979) Deconvolution of fluorescence decay curves. A critical comparison of techniques. J. Phys. Chem. 83 (10 1333 1343.
36. Bark, K. M. R. K. Forcé (1989) Observation of dual fluorescence for fluoranthene in the vapor phase. J. Phys. Chem. 93, 7985 7988.
37. Lakowicz, J. R. (1999) Principles of Fluorescence Spectroscopy, pp. 95 140. Kluwer Academic/Plenum Publishers, New York.
38. Frish, M. J., G. W. Trucks, M. H. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. R. L. Gonzalez, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart J. A. Pople (2003) Gaussian 03. Gaussian Inc., Pittsburgh, PA.
39. Cornard, J. P., J. C. Merlin, A. C. Boudet L. Vrielynck (1997) Structural study of quercetin by vibrational and electronic spectroscopies combined with semiempirical calculations. Biospectroscopy 3, 183 193. (Pubitemid 127778606)
40. Hochstrasser, R. M. C. Marzzacco (1968) Perturbations between electronic states in aromatic and heteroaromatic molecules. J. Chem. Phys. 49 (3 971 984.
41. Sengupta, P. K. M. Kasha (1979) Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin. Chem. Phys. Lett. 68, 382 385.
42. Michiya, I., Y. Fujiwara, M. Sumitani K. Yoshihara (1986) Mechanism of intramolecular excited-state proton transfer and relaxation processes in the ground and excited states of 3-hydroxyflavone and related compounds. J. Phys. Chem. 90, 5672 5678.
43. Moog, R. S., N. A. Burozski, M. M. Desai, W. R. Good, C. D. Silvers, P. A. Thompson J. D. Simon (1991) Solution photophysics of 1- and 3-aminofluorenone: The role of inter- and intramolecular hydrogen bonding in radiationless deactivation. J. Phys. Chem. 95 (22 8466 8473.