Specific deuteration in patuletin and related flavonoids via keto - Enol tautomerism: Solvent- and temperature-dependent 1H-NMR studies

Helvetica Chimica Acta

Volumn 93, Issue 3, 2010, Pages 466-481

  Faizi, Shaheen ^a   Siddiqi, Humaira ^a   Naz, Aneela ^a   Bano, Samina ^a   Lubna, ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MATRIXES; CHRYSIN; DEUTERATED DERIVATIVES; DEUTERATIONS; DONOR SOLVENTS; FLAVONOIDS; GALANGIN; H/D EXCHANGE; KAEMPFEROL; KETO-ENOL TAUTOMERISM; MYRICETIN; NMR STUDIES; PHARMACOLOGICAL ACTIVITY; TEMPERATURE DEPENDENT;

FATTY ACIDS; NUCLEAR MAGNETIC RESONANCE; PHENOLS; RATE CONSTANTS;

DEUTERIUM;

APIGENIN; CHRYSIN; FLAVONE DERIVATIVE; FLAVONOID; GALANGIN; KAEMPFEROL; LUTEOLIN; MORIN; MYRICETIN; QUERCETIN; SOLVENT;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; KETO ENOL TAUTOMERISM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; TEMPERATURE;

EID: 77949521194     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900249     Document Type: Article

References (45)

1. B. H. Havsteen, Pharmacol. Therapeut. 2002, 96, 67;
2. N. C. Veitch, R. J. Grayer, Nat. Prod. Rep. 2008, 25, 555.
3. J. B. Harborne, C. A. Williams, Phytochemistry 2000, 55, 481.
4. P.-G. Pietta, J. Nat. Prod. 2000, 63, 1035.
5. K. E. Heim, A. R. Tagliaferro, D. J. Bobilya, J. Nutr. Biochem. 2002, 13, 572.
6. Ø. M. Andersen, K. R. Markham, 'Flavonoids: Chemistry, Biochemistry and Applications', Taylor& Francis, 2006;
7. G. M. V. Júnior, C. M. de. M. Sousa, A. J. Cavalheiro, J. H. G. Lago,M. H. Chaves, Helv. Chim. Acta 2008, 91, 2159.
8. T. P. T. Cushnie,A. J. Lamb, Int. J. Antimicrob. Agents 2005, 26, 343;
9. J. Lameira, I. G. Medeiros, M. Reis, A. S. Santos, C. N. Alves, Bioorg. Med. Chem. 2006, 14, 7105.
10. I. Parejo, O. Jáuregui, F. Viladomat, J. Bastida, C. Codina, Rapid Commun. Mass Spectrom. 2004, 18, 2801.
11. A. Atha, 'The Ultimate Herb Book', Collins & Brown Ltd., London, 2001, p. 301.
12. Y. R. Chadha, in 'The Wealth of India', Publication & Information Directorate, CSIR, New Delhi, 1976, Vol. 10, pp. 109-112.
13. J. Kagan, in 'Progress in the Chemistry of Organic Natural Products', Eds. W. Herz, H. Grisebach, G.W. Kirby, and C. Tamm, Springer-Verlag, Wien - New York, 1991, pp. 87-169.
14. S. Faizi, A. Naz, Tetrahedron 2002, 58, 6185.
15. R. Saleem, M. Ahmad, A. Naz, H. Siddiqi, S. I. Ahmad, S. Faizi, Arch. Pharm. Res. 2004, 27, 1037.
16. S. Faizi, A. Naz, Helv. Chim. Acta 2004, 87, 46.
17. N. A. Kaloshina, A. V. Mazulin, Khim. Prir. Soedin. 1983, 1, 104.
18. S. N. Garg, R. Charles, S. Kumar, Fitoterapia 1999, 70, 472.
19. E. J. Park, Y. Kim, J. Kim, J. Nat. Prod. 2000, 63, 34;
20. G. R. Ickes, H. H. S. Fong, P. L. Schiff, R. E. Perdue, N. R. Farnsworth, J. Pharm. Sci. 1973, 62, 1009.
21. L. R. A. De Israilev, P. Seeligmann, Biochem. System. Ecol. 1994, 22, 431.
22. S. Faizi, H. Siddiqi, S. Bano, A. Naz, Lubna, K. Mazar, S. Nasim, T. Riaz, S. Kamal, A. Ahmad, S. A. Khan, Pharm. Biol. 2008, 46, 309;
23. S. Faizi, A. Dar, H. Siddiqi, S. Naqvi, A. Naz, S. Bano, Lubna, Pharm. Biol. 2009, (submitted).
24. D. Amić, D. Davidović-Amić, D. Bešlo, N. Trinajstić, Croat. Chem. Acta 2003, 76, 55.
25. S. Faizi, S. Zikr-ur-Rehman, M. Ali, A. Naz, Magn. Reson. Chem. 2006, 44, 838.
26. K. Wähälä, S. Rasku, K. Parikka, J. Chromatogr., B 2002, 777, 111;
27. S. Rasku, K. Wähälä, Tetrahedron 2000, 56, 913;
28. H. Kagawa, T. Takahashi, M. Uno, S. Ohta, Y. Harigaya, Chem. Pharm. Bull. 2004, 52, 953.
29. P. Sykes, in 'A Guide Book to Mechanism in Organic Chemistry', JohnWiley& Sons Inc., New York, 1986, pp. 46.
30. G. W. Gribble, R. B. Nelson, J. L. Johnson, G. C. Levy, J. Org. Chem. 1975, 40, 3720.
31. J. Clayden, N. Greeves, S. Warren, P. Wothers, in 'Organic Chemistry', Oxford University Press Inc., New York, 2001, p. 547.
32. Y. Wang, M. Hamburger, J. Gueho, K. Hostettmann, Phytochemistry 1989, 28, 2323.
33. a) 'Carbon-13 NMR of Flavonoids', Ed. P. K. Agrawal, Elsevier, 1989, p. 128, 132, 134, 140, 152, 154, 340, and 341;
34. b) C. Burns, D. A. Ellis, R. E. March, Magn. Reson. Chem. 2007, 45, 835.
35. a) P. S. Kiuru, K. Wähälä, Steroids 2006, 71, 54;
36. b) E. Leppälä, M. Pohjoispää, J. Koskimies, K. Wähälä, J. Lab. Comp. Radiopharm. 2008, 51, 407;
37. c) K. Parikka, K. Wähälä, J. Lab. Comp. Radiopharm. 2008, 51, 12.
38. A. Kale, S. Gawande, S. Kotwal, Phytother. Res. 2008, 22, 567.
39. E. Tripoli, M. L. Guardia, S. Giammanco,D. D. Majo,M. Giammanco, Food Chem. 2007, 104, 466;
40. G. Cao, E. Sofic, R. L. Prior, Free Radical Biol. Med. 1997, 22, 749.
41. V. Koleckar, E. Brojerova, Z. Rehakova, K. Kubikova, F. Cervenka, K. Kuca, D. Jun, M. Hronek, V. Opletalova, L. Opletal, Drug Chem. Toxicol. 2008, 31, 27.
42. G. J. Smith, K. R. Markham, J. Photochem. Photobiol., A 1998, 118, 99.
43. M. Fiorani, A. Accorsi, M. Blasa, G. Diamantini, E. Piatti, J. Agric. Food Chem. 2006, 54, 8328;
44. J. L. Torres, C. Lozano, L. Juliá, F. J. Sánchez-Baeza, J. M. Anglada, J. J. Centelles, M. Cascante, Bioorg. Med. Chem. 2002, 10, 2497.
45. V. N. Belov, S. M. Korneev, J. Angerer, A. de Meijere, Eur. J. Org. Chem. 2008, 4417.