Structural evidence for the inhibition of grape dihydroflavonol 4-reductase by flavonols

Acta Crystallographica Section D: Biological Crystallography

Volumn 64, Issue 8, 2008, Pages 883-891

  Trabelsi, Nadia ^a,b   Petit, Pierre ^a,c   Manigand, Claude ^a   Langlois D'Estaintot, Béatrice ^a   Granier, Thierry ^a   Chaudière, Jean ^a   Gallois, Bernard ^a  

^a CNRS   (France)

^b CENTRE DE BIOTECHNOLOGIE DE BORJ CÉDRIA   (Tunisia)

^c Centre National de la Recherche Scientifique   (France)

Author keywords

Enzyme ligand complexes; Flavonoid biosynthesis; Flavonols; Short chain dehydrogenase reductases

Indexed keywords

ALCOHOL DEHYDROGENASE; DIHYDROFLAVANOL 4 REDUCTASE; DIHYDROFLAVANOL 4-REDUCTASE; FLAVONOID; MYRICETIN; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; QUERCETIN; VEGETABLE PROTEIN;

ARTICLE; BINDING SITE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GRAPE; X RAY CRYSTALLOGRAPHY;

ALCOHOL OXIDOREDUCTASES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; FLAVONOIDS; MODELS, MOLECULAR; NADP; PLANT PROTEINS; QUERCETIN; VITIS;

VITACEAE; VITIS VINIFERA;

EID: 47749095943     PISSN: 09074449     EISSN: 13990047     Source Type: Journal    
DOI: 10.1107/S0907444908017769     Document Type: Article

References (45)

1. Almeida, J. R. M., D'Amico, E., Preuss, A., Carbone, F., Ric de Vos, C. H., Deiml, B., Mourgues, F., Perrotta, G., Fischer, T. C., Bovy, A. G., Martens, S. & Rosati, C. (2007). Arch. Biochem. Biophys. 465, 61-71.
2. Asen, S., Stewart, R. N. & Norris, K. H. (1972). Phytochemistry, 11, 1139-1144.
3. Boss, P. K., Davies, C. & Robinson, S. P. (1996). Plant Physiol. 111, 1059-1066.
4. Burbulis, I. E., Pelletier, L. K., Cain, C. C. & Shirley, B. W. (1996). SAAS Bull. Biochem. Biotechnol. 9, 29-36.
5. Burbulis, I. E. &Winkel-Shirley, B. (1999). Proc. Natl Acad. Sci. USA, 96, 12929-12934.
6. Collaborative Computational Project, Number 4 (1994). Acta Cryst. D50, 760-763.
7. Dédaldéchamp, F. & Uhel, C. (1999). Enzyme Microb. Technol. 25, 316-321.
8. DeLano, W. L. (2002). The PyMOL Molecular Graphics System. http://www.pymol.org.
9. Downey, M. O., Harvey, J. S. & Robinson, S. P. (2003). Aust. J. Grape Wine Res. 9, 110-121.
10. Eldik, G. J. van, Reijnen, W. H., Ruiter, R. K., van Herpen, M. M., Schrauwen, J. A. & Wullems, G. J. (1997). Plant J. 11, 105-113.
11. Emsley, P. & Cowtan, K. (2004). Acta Cryst. D60, 2126-2132.
12. Engh, R. A. & Huber, R. (1991). Acta Cryst. A47, 392-400.
13. Evans, P. R. (1997). Jnt CCP4/ESRF-EACBM Newsl. Protein Crystallogr. 33, 22-24.
14. Ferrer, J.-L., Jez, J. M., Bowman, M. E., Dixon, R. A. & Noel, J. P. (1999). Nature Struct. Biol. 6, 775-784.
15. Flint, S. D., Jordan, P. W. & Caldwell, M. M. (1985). Photochem. Photobiol. 41, 95-99.
16. Fujita, A., Goto-Yamamoto, N., Aramaki, I. & Hashizume, K. (2006). Biosci. Biotechnol. Biochem. 70, 632-638.
17. Gould, K. S., McKelvie, J. & Markham, K. R. (2002). Plant Cell Environ. 25, 1261-1269.
18. Halliwell, B., Rafter, J. & Jenner, A. (2005). Am. J. Clin. Nutr. 81, 268-276.
19. Harbone, J. B. & Williams, C. A. (2000). Phytochemistry, 55, 481-504.
20. Harrison, D. H. T., Bohren, K. M., Petsko, G. A., Ringe, D. & Gabbay, K. H. (1997). Biochemistry, 36, 16134-16140.
21. Hertog, M. G., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Fidanza, F., Giampaoli, S., Jansen, A., Menotti, A. & Nedejikovic, S. (1995). Arch. Intern. Med. 155, 381-386.
22. Hrazdina, G. & Wagner, G. J. (1985). Arch. Biochem. Biophys. 237, 88-100.
23. Iwashina, T. (2003). Biol. Sci. Space, 17, 24-44.
24. Jaakola, L., Määttä, K., Pirttilä, A. M., Törrönen, R., Kärenlampi, S. & Hohtola, A. (2002). Plant Physiol. 130, 729-739.
25. Jez, J. M., Bowman, M. E., Dixon, R. A. & Noel, J. P. (2000). Nature Struct. Biol. 7, 786-791.
26. Jin, G.-Z., Yamagata, Y. & Tomita, K. (1990). Acta Cryst. C46, 310-313.
27. Kleywegt, G. J. & Jones, T. A. (1998). Acta Cryst. D54, 1119-1131.
28. Laskowski, R. A., MacArthur, M. W., Moss, D. S. & Thornton, J. M. (1993). J. Appl. Cryst. 26, 283-291.
29. Leslie, A. G. W. (1992). Jnt CCP4/ESF-EACBM Newsl. Protein Crystallogr. 26.
30. Li, Y., Fanq, H. & Xu, W. (2007). Mini Rev. Med. Chem. 7, 663-678.
31. Murshudov, G. N., Vagin, A. A. & Dodson, E. J. (1997). Acta Cryst. D53, 240-255.
32. Navaza, J., Panepucci, E. H. & Martin, C. (1998). Acta Cryst. D54, 817-821.
33. Offen, W., Martinez-Fleites, C., Yang, M., Kiat-Lim, E., Davis, B. G., Tarling, C. A., Ford, C. M., Bowles, D. J. & Davies, G. J. (2006). EMBO J. 25, 1396-1405.
34. Petit, P., Granier, T., Langlois d'Estaintot, B., Manigand, C., Bathany, K., Schmitter, J. M., Lauvergeat, V., Hamdi, S. & Gallois, B. (2007). J. Mol. Biol. 368, 1345-1357.
35. Ross, J. A. & Kasum, C. M. (2002). Annu. Rev. Nutr. 22, 19-34.
36. Rossi, M., Rickles, L. F. & Halpin, W. A. (1986). Bioorg. Chem. 14, 55-69.
37. Scheffeldt, P. & Hrazdina, G. (1978). J. Food Sci. 43, 517-520.
38. Selivanova, I. A., Tyukavkina, N. A., Kolesnik, Y. A., Nesterov, V. N., Kuleshova, L. N., Khutoryanskii, V. A., Bazhenov, B. N. & Saibotalov, M. Y. (1999). Pharm. Chem. J. 33, 222-224.
39. Stafford, H. A. & Lester, H. H. (1982). Plant. Physiol. 70, 695-698.
40. Vagin, A. & Teplyakov, A. (1997). J. Appl. Cryst. 30, 1022-1025.
41. Vaguine, A. A., Richelle, J. & Wodak, S. J. (1999). Acta Cryst. D55, 191-205.
42. Vriend, G. & Sander, C. (1993). J. Appl. Cryst. 26, 47-60.
43. Wilmouth, R. C., Turnbull, J. J., Welford, R. W., Clifton, I. J., Prescott, A. G. & Schoefield, C. J. (2002). Structure, 10, 93-103.
44. Xie, D.-Y., Sharma, S. B. & Dixon, R. A. (2004). Arch. Biochem. Biophys. 422, 91-102.
45. Xu, Z., Liu, B., Ning, Z. & Zhang, Y. (2007). Acta Cryst. E63, o4384.