Cloning, characterization, and activity analysis of a flavonol synthase gene FtFLS1 and its association with flavonoid content in tartary buckwheat

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 20, 2012, Pages 5161-5168

  Li, Chenglei ^a   Bai, Yuechen ^a   Li, Shuangjiang ^a   Chen, Hui ^a   Han, Xueyi ^a   Zhao, Haixia ^a   Shao, Jirong ^a   Park, Sang Un ^b   Wu, Qi ^a  

^a SICHUAN AGRICULTURAL UNIVERSITY   (China)

^b Chungnam National University   (South Korea)

Author keywords

biosynthetic pathways; Fagopyrum tataricum; flavonoids; flavonol synthase; functional expression; tartary buckwheat

Indexed keywords

BIOSYNTHETIC PATHWAY; FAGOPYRUM TATARICUM; FLAVONOL SYNTHASE; FUNCTIONAL EXPRESSION; TARTARY BUCKWHEAT;

ALCOHOLS; BIOCHEMISTRY; BIOSYNTHESIS; CLONING; ESCHERICHIA COLI; FLAVONOIDS; PLANTS (BOTANY); RECOMBINANT PROTEINS;

GENES;

FLAVONOID; FLAVONOL SYNTHASE; OXIDOREDUCTASE; RECOMBINANT PROTEIN; RUTOSIDE; VEGETABLE PROTEIN;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; ESCHERICHIA COLI; FAGOPYRUM; GENE EXPRESSION; GENETICS; METABOLISM; MOLECULAR CLONING;

CLONING, MOLECULAR; ESCHERICHIA COLI; FAGOPYRUM; FLAVONOIDS; GENE EXPRESSION; OXIDOREDUCTASES; PLANT PROTEINS; RECOMBINANT PROTEINS; RUTIN;

ESCHERICHIA COLI; FAGOPYRUM TATARICUM;

EID: 84861442911     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf205192q     Document Type: Article

References (40)

1. Fabjan, N.; Rode, J.; Košir, I. J.; Wang, Z.; Zhang, Z.; Kreft, I. Tartary buckwheat (Fagopyrum tataricum Gaertn.) as a source of dietary rutin and quercitrin J. Agric. Food Chem. 2003, 51 (22) 6452-6455
2. Conesa, C. M.; Ortega, V. V.; GascoÌn, M. J. Y.; Baños, M. A.; Jordana, M. C.; Benavente-GarciÌa, O.; Castillo, J. Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin J. Agric. Food Chem. 2005, 53 (17) 6791-6797
3. Harborne, J. B.; Williams, C. A. Advances in flavonoid research since 1992 Phytochemistry 2000, 55 (6) 481-504
4. Hagmann, M. L.; Heller, W.; Grisebach, H. Induction and characterization of a microsomal flavonoid 3â-hydroxylase from parsley cell cultures Eur. J. Biochem. 1983, 134 (3) 547-554
5. Kaltenbach, M.; Schröder, G.; Schmelzer, E.; Lutz, V.; Schröder, J. Flavonoid hydroxylase from Catharanthus roseus: cDNA, heterologous expression, enzyme properties and cell-type specific expression in plants Plant J. 1999, 19 (2) 183-193
6. Holton, T. A.; Brugliera, F.; Tanaka, Y. Cloning and expression of flavonol synthase from Petunia hybrida Plant J. 1993, 4 (6) 1003-1010
7. Turnbull, J. J.; Nakajima, J.; Welford, R. W.; Yamazaki, M.; Saito, K.; Schofield, C. J. Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis: anthocyanidin synthase, flavonol synthase, and flavanone 3Î-hydroxylase J. Biol. Chem. 2004, 279, 1206-1216
8. Britsch, L.; Heller, W.; Grisebach, H. Conversion of flavanone to flavone, dihydroflavonol and flavonol with an enzyme system from cell culture of parsley Z. Naturforsch. 1981, 36 (9/10) 742-750
9. Pelletier, M. K.; Burbulis, I. E.; Winkel-Shirley, B. Disruption of specific flavonoid genes enhances the accumulation of flavonoid enzymes and end-products in Arabidopsis seedlings Plant Mol. Biol. 1999, 40 (1) 45-54
10. Preuß, A.; Stracke, R.; Weisshaar, B.; Hillebrecht, A.; Matern, U.; Martens, S. Arabidopsis thaliana expresses a second functional flavonol synthase FEBS Lett. 2009, 583 (12) 1981-1986
11. Ferreyra, M. L. F.; Rius, S.; Emiliani, J.; Pourcel, L.; Feller, A.; Morohashi, K.; Casati, P.; Grotewold, E. Cloning and characterization of a UV-B-inducible maize flavonol synthase Plant J. 2010, 62 (1) 77-91
12. Kim, B. G.; Joe, E. J.; Ahn, J. H. Molecular characterization of flavonol synthase from poplar and its application to the synthesis of 3- O -methylkaempferol Biotechnol. lett. 2010, 32 (4) 579-584
13. Wellmann, F.; Lukačin, R.; Moriguchi, T.; Britsch, L.; Schiltz, E.; Matern, U. Functional expression and mutational analysis of flavonol synthase from Citrus unshiu Eur. J. Biochem. 2002, 269 (16) 4134-4142
14. Gupta, N.; Sharma, S. K.; Rana, J. C.; Chauhan, R. S. Expression of flavonoid biosynthesis genes vis-aÌ-vis rutin content variation in different growth stages of Fagopyrum species J. Plant Physiol. 2011, 168 (17) 2117-2123
15. Li, X.; Park, N. I.; Xu, H.; Woo, S. H.; Park, C. H.; Park, S. U. Differential expression of flavonoid biosynthesis genes and accumulation of phenolic compounds in common buckwheat (Fagopyrum esculentum) J. Agric. Food Chem. 2010, 58 (23) 12176-12181
16. Park, N. I.; Li, X.; Suzuki, T.; Kim, S. J.; Woo, S. H.; Park, C. H.; Park, S. U. Differential expression of anthocyanin biosynthetic genes and anthocyanin accumulation in tartary buckwheat cultivars 'Hokkai T8' and 'Hokkai T10' J. Agric. Food Chem. 2011, 59 (6) 2356-2361
17. Geourjon, C.; Deleage, G. SOPM: a self-optimized method for protein secondary structure prediction Protein Eng. 1994, 7 (2) 157-164
18. Arnold, K.; Bordoli, L.; Kopp, J.; Schwede, T. The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling Bioinformatics 2006, 22 (2) 195-201
19. Kumar, S.; Tamura, K.; Nei, M. MEGA: molecular evolutionary genetics analysis software for microcomputers Comput. Appl. Biosci. 1994, 10 (2) 189-191
20. Chua, C. S.; Biermann, D.; Goo, K. S.; Sim, T. S. Elucidation of active site residues of Arabidopsis thaliana flavonol synthase provides a molecular platform for engineering flavonols Phytochemistry 2008, 69 (1) 66-75
21. Sedmak, J. J.; Grossberg, S. E. A rapid, sensitive, and versatile assay for protein using Coomassie brilliant blue G250 Anal. Biochem. 1977, 79 (1-2) 544-552
22. Prescott, A. G.; John, P. Dioxygenases: molecular structure and role in plant metabolism Annu. Rev. Plant Biol. 1996, 47 (1) 245-271
23. Wu, Q.; Li, C.; Chen, H.; Shao, J.; Zhao, H.; Gou, L. Molecular structure characterization of Fagopyrum tataricum chalcone synthase and its tissue-specific expression during florescence Chin. J. Biochem. Mol. Biol. 2010, 26 (12) 1151-1160
24. Liu, B.; Zhu, Y. Extraction of flavonoids from flavonoid-rich parts in tartary buckwheat and identification of the main flavonoids J. Food Eng. 2007, 78 (2) 584-587
25. Kim, B. G.; Kim, J. H.; Kim, J.; Lee, C.; Ahn, J. Accumulation of flavonols in response to ultraviolet-B irradiation in soybean is related to induction of flavanone 3-Î-hydroxylase and flavonol synthase Mol. Cells 2008, 25 (2) 247-252
26. Wilmouth, R. C.; Turnbull, J. J.; Welford, R. W. D.; Clifton, I. J.; Prescott, A. G.; Schofield, C. J. Structure and mechanism of anthocyanidin synthase from Arabidopsis thaliana Structure 2002, 10 (1) 93-103
27. Owens, D. K.; Alerding, A. B.; Crosby, K. C.; Bandara, A. B.; Westwood, J. H.; Winkel, B. S. J. Functional analysis of a predicted flavonol synthase gene family in Arabidopsis Plant Physiol. 2008, 147 (3) 1046-1061
28. Lin, G. Z.; Lian, Y. J.; Ryu, J. H.; Sung, M. K.; Park, J. S.; Park, H. J.; Park, B. K.; Shin, J. S.; Lee, M. S.; Cheon, C. I. Expression and purification of His-tagged flavonol synthase of Camellia sinensis from Escherichia coli Protein Express. Purif. 2007, 55 (2) 287-292
29. Moriguchi, T.; Kita, M.; Ogawa, K.; Tomono, Y.; Endo, T.; Omura, M. Flavonol synthase gene expression during Citrus fruit development Physiol. Plant. 2002, 114 (2) 251-258
30. Lukačin, R.; Britsch, L. Identification of strictly conserved histidine and arginine residues as part of the active site in Petunia hybrida flavanone 3Î-hydroxylase Eur. J. Biochem. 1997, 249 (3) 748-757
31. Pelletier, M. K.; Murrell, J. R.; Shirley, B. W. Characterization of flavonol synthase and leucoanthocyanidin dioxygenase genes in Arabidopsis (further evidence for differential regulation of "early" and "late" genes) Plant Physiol. 1997, 113 (4) 1437-1445
32. Stracke, R.; Ishihara, H.; Huep, G.; Barsch, A.; Mehrtens, F.; Niehaus, K.; Weisshaar, B. Differential regulation of closely related R2R3-MYB transcription factors controls flavonol accumulation in different parts of the Arabidopsis thaliana seedling Plant J. 2007, 50 (4) 660-677
33. Stracke, R.; Jahns, O.; Keck, M.; Tohge, T.; Niehaus, K.; Fernie, A. R.; Weisshaar, B. Analysis of production of flavonol glycosides-dependent flavonol glycoside accumulation in Arabidopsis thaliana plants reveals MYB11-, MYB12- and MYB111-independent flavonol glycoside accumulation New Phytol. 2010, 188 (4) 985-1000
34. Jiang, P.; Burczynski, F.; Campbell, C.; Pierce, G.; Austria, J. A.; Briggs, C. J. Rutin and flavonoid contents in three buckwheat species Fagopyrum esculentum, F. tataricum, and F. homotropicum and their protective effects against lipid peroxidation Food Res. Int. 2007, 40 (3) 356-364
35. Kim, S. J.; Zaidul, I. S. M.; Suzuki, T.; Mukasa, Y.; Hashimoto, N.; Takigawa, S.; Noda, T.; Matsuura-Endo, C.; Yamauchi, H. Comparison of phenolic compositions between common and tartary buckwheat (Fagopyrum) sprouts Food Chem. 2008, 110 (4) 814-820
36. Zhao, J.; Dixon, R. A. The 'ins' and 'outs' of flavonoid transport Trends Plant Sci. 2010, 15 (2) 72-80
37. Buer, C. S.; Muday, G. K.; Djordjevic, M. A. Implications of long-distance flavonoid movement in Arabidopsis thaliana Plant Signal. Behav. 2008, 3 (6) 415-417
38. Saslowsky, D. E.; Warek, U.; Winkel, B. S. J. Nuclear localization of flavonoid enzymes in Arabidopsis J. Biol. Chem. 2005, 280 (25) 23735-23740
39. Alfenito, M. R.; Souer, E.; Goodman, C. D.; Buell, R.; Mol, J.; Koes, R.; Walbot, V. Functional complementation of anthocyanin sequestration in the vacuole by widely divergent glutathione S -transferases Plant Cell 1998, 10 (7) 1135-1150
40. Kitamura, S.; Shikazono, N.; Tanaka, A. Transparent testa 19 is involved in the accumulation of both anthocyanins and proanthocyanidins in Arabidopsis Plant J. 2004, 37 (1) 104-114