Characterization of hydroxycinnamoyltransferase from rice and its application for biological synthesis of hydroxycinnamoyl glycerols

Phytochemistry

Volumn 76, Issue , 2012, Pages 25-31

  Kim, In A ^a   Kim, Bong Gyu ^a   Kim, Mihyang ^a   Ahn, Joong Hoon ^a  

^a Konkuk University   (South Korea)

Author keywords

Gramineae; Hydroxycinnamic acid; Hydroxycinnamic acid transferase; Oryza sativa; Rice

Indexed keywords

ACYL COENZYME A; ACYLGLYCEROL; ACYLTRANSFERASE; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; COENZYME A TRANSFERASE; COUMARIC ACID; DRUG DERIVATIVE; FERULIC ACID; GLUTATHIONE TRANSFERASE; GLYCEROL; HYBRID PROTEIN; PLANT RNA; SHIKIMIC ACID; VEGETABLE PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; ENZYME ASSAY; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; ESTERIFICATION; GENETIC TRANSFORMATION; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MOLECULAR CLONING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYLOGENY; PLANT GENE; RICE;

ACYL COENZYME A; ACYLTRANSFERASES; CAFFEIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLONING, MOLECULAR; COENZYME A-TRANSFERASES; COUMARIC ACIDS; ENZYME ASSAYS; ESCHERICHIA COLI; ESTERIFICATION; GENES, PLANT; GLUTATHIONE TRANSFERASE; GLYCERIDES; GLYCEROL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORYZA SATIVA; PHYLOGENY; PLANT PROTEINS; RECOMBINANT FUSION PROTEINS; RNA, PLANT; SHIKIMIC ACID; SUBSTRATE SPECIFICITY; TRANSFORMATION, GENETIC;

ESCHERICHIA COLI; NICOTIANA TABACUM; ORYZA SATIVA; POACEAE;

EID: 84862831270     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.12.015     Document Type: Article

References (34)

1. A. Bayer, X. Ma, and J. Stöckigt Acetyltransfer in natural product biosynthesis-functional cloning and molecular analysis of vinorine synthase Bioorgan. Med. Chem. 12 2004 2787 2795
2. A.S. Chawla, M. Singh, M.S. Murthy, M.P. Gupta, and H. Singh Anti-inflammatory action of ferulic acid and its esters in carrageenan induced rat paw edema model Indian J. Exp. Biol. 25 1987 187 189
3. M.N. Clifford Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden J. Sci. Food Agric. 79 1999 362 372
4. C. Comino, S. Lanteri, E. Portis, A. Acquadro, A. Romani, A. Hehn, R. Larbat, and F. Bourguard Isolation and functional characterization of cDNA coding a hydroxycinnamoyltransferase involved in phenylpropanoid biosynthesis in Cynara cardunculus L. BMC Plant Biol. 7 2007 14
5. D.L. Compton, J.A. Laszlo, and M.A. Berhow Lipase-catalyzed synthesis of ferulate esters J. Am. Oil Chem. Soc. 77 2000 513 519
6. R. Croteau, T.M. Kutchan, and N.G. Lewis Natural products (secondary metabolites) B.B. Buchanan, W. Gruissem, R.L. Jones, Biochemistry and Molecular Biology of Plants 2000 American Society of Plant Physiologists Rockville, MD 1250 1318
7. J.C. D'Auria Acyltransferases in plant: a good time to be BAHD Curr. Opin. Plant Biol. 9 2006 331 340
8. P.M. Dewick Medicinal Natural Products: A Biosynthetic Approach second ed. 2002 Wiley Chichester
9. T. Goujon, R. Sibout, B. Pollet, B. Maba, L. Nussaume, N. Bechtold, F. Lu, J. Ralph, I. Mila, Y. Barriere, C. Lapierre, and L. Jouanin A new Arabidopsis thaliana mutant deficient in the expression of O-methyltransferase impacts lignins and sinapoyl esters Plant Mol. Biol. 51 2003 973 989
10. X.-Z. He, and R.A. Dixon Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4′-O-methylated isoflavonoid phytoalxeins and disease resistance in alfalfa Plant Cell 12 2000 1689 1702
11. L. Hoffmann, S. Maury, F. Martz, P. Geoffroy, and M. Legrand Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism J. Biol. Chem. 278 2003 95 103
12. J.M. Humphreys, and C. Chapple Rewriting the lignin roadmap Curr. Opin. Plant Biol. 5 2002 224 229
13. D.-Z. Jin, Z.-D. Min, G.C.Y. Chiou, M.I. Iinuma, and T. Tanaka Two p-coumaroyl glycerides from Juncus effusu Phytochemistry 41 1996 545 547
14. H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi Antioxidant properties of ferulic acid and its related compounds J. Agric. Food Chem. 50 2002 2161 2168
15. B.G. Kim, I.-A. Kim, and J.-H. Ahn Characterization of hydroxycinnamoyl-coenzyme A shikimate hydroxycinnamoyltransferase from Populus euramericana J. Kor. Soc. Appl. Biol. Chem. 54 2011 817 821
16. S.-K. Kim, D.H. Kim, B.G. Kim, Y.M. Jeon, B.S. Hong, and J.-H. Ahn Cloning and characterization of the UDP glucose/galactose epimerases of Oryza sativa J. Kor. Soc. Appl. Biol. Chem. 52 2009 315 320
17. B.G. Kim, J.H. Kim, S.Y. Min, K.H. Shin, J.H. Kim, H.I. Kim, S.N. Ryu, and J.-H. Ahn Anthocyanin content in rice is related to expression level of anthocyanin biosynthetic genes J. Plant Biol. 50 2007 156 160
18. B.G. Kim, Y. Lee, H.-G. Hur, Y. Lim, and J.-H. Ahn Flavonoid 3′-O-methyltransferase from rice. cDNA cloning, characterization and functional expression Phytochemistry 67 2006 387 394
19. J.H. Ko, B.G. Kim, J.H. Kim, H. Kim, C.E. Lim, J. Lim, C. Lee, Y. Lim, and J.-H. Ahn Four glucosyltransferases from rice. cDNA cloning, expression, and characterization J. Plant Physiol. 165 2008 435 444
20. K.M. Ku, J.N. Choi, J. Kim, J.K. Kim, L.G. Yoo, S.J. Lee, Y.-S. Hong, and C.H. Lee Metabolomics analysis reveals the compositional differences of shade grown tea (Camellia sinensis L.) J. Agric. Food Chem. 58 2010 418 426
21. K.W. Lee, and H.J. Lee The roles of polyphenols in cancer chemoprevention Biofactors 26 2006 105 121
22. Y.J. Lee, Y. Jeon, J.S. Lee, B.G. Kim, C.H. Lee, and J.-H. Ahn Enzymatic synthesis of phenolic CoAs using 4-coumarate:coenzyme A ligase (4CL) from rice Bull. Kor. Chem. Soc. 28 2007 365 366
23. L. Mondolot, P. La Fisca, B. Buatois, E. Talansier, A. De Kochko, and C. Campa Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development Ann. Bot. 98 2006 33 40
24. I. Muzac, J. Wang, D. Anzellotti, H. Zhang, and R.K. Ibrahim Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3′-O- methyltransferase and characterization of the gene product Arch. Biochem. Biophys. 375 2000 385 388
25. H. Nakashima, T. Murakami, N. Yamamoto, T. Naoe, Y. Kawazoe, K. Konno, and H. Sakagami Lignified materials as medicinal resources. V. Anti-HIV activity of some synthetic lignins Chem. Pharm. Bull. 40 1992 2102 2105
26. R. Niggeweg, A. Michael, and C. Martin Engineering plants with increased levels of the antioxidant chlorogenic acid Nat. Biotechnol. 22 2004 746 754
27. M. Peterson, Y. Abdullah, J. Benner, D. Eberle, K. Gehlen, S. Hücherig, V. Janiak, K.H. Kim, M. Sander, C. Weitzel, and S. Wolters Evolution of rosmarinic acid biosynthesis Phytochemistry 70 2009 1663 1679
28. S. Pervaiz Resveratrol: from grapevines to mammalian biology FASEB J. 17 2003 1975 1985
29. E.C.A. Rice, N.J. Miller, and G. Paganga Structure antioxidant activity relationships of flavonoids and phenolic acids Free Rad. Biol. Med. 20 1996 933 956
30. B. St Pierre, and V. De Luca Evolution of acyltransferase genes: origin and diversification of the BAHD superfamily of acyltransferases involved in secondary metabolism J.T. Romeo, R. Ibrahim, L. Varin, V. De Luca, Evolution of Metabolic Pathways Recent Advances in Phytochemistry vol. 34 2000 Elsevier Science Ltd. 285 315
31. S. Tian, K. Nakamura, T. Cui, and H. Kayahara High-performance liquid chromatographic determination of phenolic compounds in rice J. Chromatogr. A 1063 2005 121 128
32. M. Tsuchiyama, T. Sakamoto, S. Tanimori, S. Murata, and H. Kawasaki Enzymatic synthesis of hydroxycinnamic acid glycerol esters using type A feruloyl esterase from Aspergillus niger Biosci. Biotechnol. Biochem. 71 2007 2606 2609
33. Y. Woo, D. Koh, and Y. Lim Complete assignments of NMR data of salens and their cobalt (III) complexes Magn. Reson. Chem. 47 2009 184 189
34. Z. Zhao, and M.H. Moghadasian Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies Phytochem. Rev. 9 2010 133 145