Cloning and functional characterization of a 4-coumarate CoA ligase from liverwort Plagiochasma appendiculatum

Phytochemistry

Volumn 111, Issue , 2015, Pages 48-58

  Gao, Shuai ^a   Yu, Hai Na ^a   Xu, Rui Xue ^a   Cheng, Ai Xia ^a   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

4 Coumarate: coenzyme; A ligase; Aytoniaceae; Bis bibenzyls; Flavonoids; Liverwort; Marchantiales; Phenylpropanoids; Plagiochasma appendiculatum

Indexed keywords

AYTONIACEAE; BRYOPHYTA; CHLOROPHYTA; EMBRYOPHYTA; ESCHERICHIA COLI; GYMNOSPERMAE; MAGNOLIOPHYTA; MARCHANTIALES; MARCHANTIOPHYTA; PLAGIOCHASMA APPENDICULATUM;

4-COUMARATE-COA LIGASE; 4-COUMARIC ACID; ACETIC ACID DERIVATIVE; BIBENZYL DERIVATIVE; COUMARIC ACID; CYCLOPENTANE DERIVATIVE; FLAVONOID; JASMONIC ACID METHYL ESTER; LONG CHAIN FATTY ACID COENZYME A LIGASE; OXYLIPIN; PHENYLPROPIONIC ACID DERIVATIVE; RECOMBINANT PROTEIN;

CHEMISTRY; CLONING; ENZYMOLOGY; GENETICS; KINETICS; LIVERWORT; METABOLISM; MOLECULAR GENETICS;

ACETATES; BIBENZYLS; CLONING, ORGANISM; COENZYME A LIGASES; COUMARIC ACIDS; CYCLOPENTANES; FLAVONOIDS; HEPATOPHYTA; KINETICS; MOLECULAR SEQUENCE DATA; OXYLIPINS; PHENYLPROPIONATES; RECOMBINANT PROTEINS;

EID: 84922705763     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.12.017     Document Type: Article

References (51)

1. S.M. Allina, A. Pri-Hadash, D.A. Theilmann, B.E. Ellis, and C.J. Douglas 4-Coumarate: coenzyme A ligase in hybrid poplar properties of native enzymes, cDNA cloning, and analysis of recombinant enzymes Plant Physiol. 116 1998 743 754
2. A.M. Anterola, J.-H. Jeon, L.B. Davin, and N.G. Lewis Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism J. Biol. Chem. 277 2002 18272 18280
3. K. Arnold, L. Bordoli, J. Kopp, and T. Schwede The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling Bioinformatics 22 2006 195 201
4. Y. Asakawa Terpenoids and aromatic compounds with pharmacological activity from bryophytes Bryophytes their Chemistry and Chemical Taxonomy 1990 Clarendon Press Oxford 369 410
5. Y. Asakawa Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis(bibenzyl)s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts Phytochemistry 56 2001 297 312
6. Y. Asakawa, and A. Ludwiczuk Distribution of cyclic and acyclic bis-bibenzyls in the Marchantiophyta (liverworts), ferns and higher plants and their biological activities, biosynthesis, and total synthesis Heterocycles 86 2012 891 917
7. T. Beuerle, and E. Pichersky Enzymatic synthesis and purification of aromatic coenzyme A esters Anal. Biochem. 302 2002 305 312
8. E. Bramucci, A. Paiardini, F. Bossa, and S. Pascarella PyMod: sequence similarity searches, multiple sequence-structure alignments, and homology modeling within PyMOL BMC Bioinformatics 13 2012 S2:1-S2:6
9. A. Cheng, L. Wang, Y. Sun, and H. Lou Identification and expression analysis of key enzymes of the terpenoids biosynthesis pathway of a liverwort Plagiochasma appendiculatum by EST analysis Acta Physiol. Plant. 35 2013 107 118
10. M.E.K. Chowdhury, B. Choi, B.K. Cho, J.B. Kim, S.U. Park, S. Natarajan, H.S. Lim, and H. Bae Regulation of 4CL, encoding 4-coumarate: coenzyme A ligase, expression in kenaf under diverse stress conditions Plant Omics 6 2013 254 262
11. M.A. Costa, D.L. Bedgar, S.G.A. Moinuddin, K.W. Kim, C.L. Cardenas, F.C. Cochrane, J.M. Shockey, G.L. Helms, Y. Amakura, H. Takahash, J.K. Milhollan, L.B. Davin, J. Browse, and N.G. Lewis Characterization in vitro and in vivo of the putative multigene 4-coumarate:CoA ligase network in Arabidopsis: syringyl lignin and sinapate/sinapyl alcohol derivative formation Phytochemistry 66 2005 2072 2091
12. L. Deluc, F. Barrieu, C. Marchive, V. Lauvergeat, A. Decendit, T. Richard, J.-P. Carde, J.-M. Mérillon, and S. Hamdi Characterization of a grapevine R2R3-MYB transcription factor that regulates the phenylpropanoid pathway Plant Physiol. 140 2006 499 511
13. R.A. Dixon, and N.L. Paiva Stress-induced phenylpropanoid metabolism Plant Cell 7 1995 1085 1097
14. R.A. Dixon, and C.L. Steele Flavonoids and isoflavonoids - a gold mine for metabolic engineering Trends Plant Sci. 4 1999 394 400
15. R.A. Dixon, L. Achnine, P. Kota, C.J. Liu, M. Reddy, and L. Wang The phenylpropanoid pathway and plant defence - a genomics perspective Mol. Plant Pathol. 3 2002 371 390
16. J. Ehlting, D. Büttner, Q. Wang, C.J. Douglas, I.E. Somssich, and E. Kombrink Three 4-coumarate: coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms Plant J. 19 1999 9 20
17. J. Espiñeira, E. Novo Uzal, L. Gómez Ros, J. Carrión, F. Merino, A. Ros Barceló, and F. Pomar Distribution of lignin monomers and the evolution of lignification among lower plants Plant Biol. 13 2011 59 68
18. S. Friederich, U.H. Maier, B. Deus-Neumann, Y. Asakawa, and M. H Zenk Biosynthesis of cyclic bis(bibenzyls) in Marchantia polymorpha Phytochemistry 50 1999 589 598
19. M.M. Gaid, D. Sircar, A. Müller, T. Beuerle, B. Liu, L. Ernst, R. Hänsch, and L. Beerhues Cinnamate: CoA ligase initiates the biosynthesis of a benzoate-derived xanthone phytoalexin in Hypericum calycinum cell cultures Plant Physiol. 160 2012 1267 1280
20. G. Gambino, I. Perrone, and I. Gribaudo A rapid and effective method for RNA extraction from different tissues of grapevine and other woody plants Phytochem. Anal. 19 2008 520 525
21. G.G. Gross, and M.H. Zenk Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissue of Forsthia Eur. J. Biochem. 42 1974 453 459
22. J. Gui, J. Shen, and L. Li Functional characterization of evolutionarily divergent 4-coumarate: coenzyme A ligases in rice Plant Physiol. 157 2011 574 586
23. B. Hamberger, and K. Hahlbrock The 4-coumarate: CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes Proc. Natl. Acad. Sci. U.S.A. 101 2004 2209 2214
24. Y. Hu, Y. Gai, L. Yin, X. Wang, C. Feng, L. Feng, D. Li, X.-N. Jiang, and D.-C. Wang Crystal structures of a Populus tomentosa 4-coumarate: CoA ligase shed light on its enzymatic mechanisms Plant Cell 22 2010 3093 3104
25. M. Kaneko, Y. Ohnishi, and S. Horinouchi Cinnamate: coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3 (2) J. Bacteriol. 185 2003 20 27
26. S.-J. Kim, M.-R. Kim, D.L. Bedgar, S.G. Moinuddin, C.L. Cardenas, L.B. Davin, C. Kang, and N.G. Lewis Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis Proc. Natl. Acad. Sci. U.S.A. 101 2004 1455 1460
27. K.W. Kim, S.G.S. Moinuddin, K.M. Atwell, M.A. Costa, L.B. Davin, and N.G. Lewis Opposite stereoselectivities of dirigent proteins in Arabidopsis and Schizandra species J. Biol. Chem. 287 2012 33957 33972
28. K.-H. Knobloch, and K. Hahlbrock Isoenzymes of p-coumarate: CoA ligase from cell suspension cultures of Glycine max Eur. J. Biochem. 52 1975 311 320
29. A. Kumar, and B.E. Ellis 4-Coumarate: CoA ligase gene family in Rubus idaeus: cDNA structures, evolution, and expression Plant Mol. Biol. 31 2003 327 340
30. H.-X. Lou, G.-Y. Li, and F.-Q. Wang A cytotoxic diterpenoid and antifungal phenolic compounds from Frullania muscicola steph J. Asian Nat. Prod. Res. 4 2002 87 94
31. T. Lüderitz, G. Schatz, and H. Grisebach Enzymic synthesis of lignin precursors. Purification and properties of 4-coumarate: CoA ligase from cambial sap of spruce (Picea dies L.) Eur. J. Biochem. 123 1982 583 586
32. H. Meng, and W.H. Campbell Facile enzymic synthesis of caffeoyl CoA Phytochemistry 44 1997 605 608
33. A.S. Mildvan Inverse thinking about double mutants of enzymes Biochemistry 43 2004 14517 14520
34. A.S. Mildvan, D.J. Weber, and A. Kuliopulos Quantitative interpretations of double mutations of enzymes Arch. Biochem. Biophys. 294 1992 327 340
35. T. Nakatsu, S. Ichiyama, J. Hiratake, A. Saldanha, N. Kobashi, K. Sakata, and H. Kato Structural basis for the spectral difference in luciferase bioluminescence Nature 440 2006 372 376
36. N. Obel, and H.V. Scheller Enzymatic synthesis and purification of caffeoyl-CoA, p-coumaroyl-CoA, and feruloyl-CoA Anal. Biochem. 286 2000 38 44
37. S. Porebski, L.G. Bailey, and B.R. Baum Modification of a CTAB DNA extraction protocol for plants containing high polysaccharide and polyphenol components Plant Mol. Biol. Rep. 15 1997 8 15
38. A. Rani, K. Singh, P. Sood, S. Kumar, and P.S. Ahuja p-Coumarate: CoA ligase as a key gene in the yield of catechins in tea [Camellia sinensis (L.) O. Kuntze] Funct. Integr. Genomics 9 2009 271 275
39. K. Schneider, K. Hövel, K. Witzel, B. Hamberger, D. Schomburg, E. Kombrink, and H.-P. Stuible The substrate specificity-determining amino acid code of 4-coumarate: CoA ligase Proc. Natl. Acad. Sci. U.S.A. 100 2003 8601 8606
40. M.V. Silber, H. Meimberg, and J. Ebel Identification of a 4-coumarate: CoA ligase gene family in the moss, Physcomitrella patens Phytochemistry 69 2008 2449 2456
41. J. Stöckigt, and M. Zenk Chemical syntheses and properties of hydroxycinnamoyl-coenzyme A derivatives Z Naturforsch C Biosci. 30 1974 352 358
42. Y. Sun, Y. Wu, Y. Zhao, X. Han, H. Lou, and A. Cheng Molecular cloning and biochemical characterization of two cinnamyl alcohol dehydrogenases from a liverwort Plagiochasma appendiculatum Plant Physiol. Biochem. 70 2013 133 141
43. K. Tamura, J. Dudley, M. Nei, and S. Kumar MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0 Mol. Biol. Evol. 24 2007 1596 1599
44. D.G. Vassão, K.-W. Kim, L.B. Davin, and N.G. Lewis Lignans (neolignans) and allyl/propenyl phenols: biogenesis, structural biology, and biological/human health considerations L. Mander, H.-W. Lui, Comprehensive Natural Products II Chemistry and Biology vol. 1 2010 Elsevier Oxford 815 928
45. T. Vogt Phenylpropanoid biosynthesis Mol. Plant. 3 2010 2 20
46. A. Wagner, L. Donaldson, H. Kim, L. Phillips, H. Flint, D. Steward, K. Torr, G. Koch, U. Schmitt, and J. Ralph Suppression of 4-coumarate-CoA ligase in the coniferous gymnosperm Pinus radiata Plant Physiol. 149 2009 370 383
47. J.K. Weng, and C. Chapple The origin and evolution of lignin biosynthesis New Phytol. 187 2010 273 285
48. R. Whetten, and R. Sederoff Lignin biosynthesis Plant Cell 7 1995 1001 1013
49. H. Xu, N.I. Park, X. Li, Y.K. Kim, S.Y. Lee, and S.U. Park Molecular cloning and characterization of phenylalanine ammonia-lyase, cinnamate 4-hydroxylase and genes involved in flavone biosynthesis in Scutellaria baicalensis Bioresour. Technol. 101 2010 9715 9722
50. H. Xu, F. Zhang, B. Liu, D.V. Huhman, L.W. Sumner, R.A. Dixon, and G. Wang Characterization of the formation of branched short-chain fatty acid: CoAs for bitter acid biosynthesis in hop glandular trichomes Mol. Plant 6 2013 1301 1317
51. H.-N. Yu, X.-Y. Liu, S. Gao, X.-J. Han, A.-X. Cheng, and H.-X. Lou Molecular cloning and functional characterization of a phenylalanine ammonia-lyase from liverwort Plagiochasma appendiculatum Plant Cell Tissue Organ Cult. 117 2014 265 277