Advertisement

Journal of Plant Biology

, Volume 49, Issue 1, pp 55–60 | Cite as

Caffeic acid o-methyltransferase fromPopulus deltoides: functional expression and characterization

  • Bong Gyu Kim
  • Yoon Jung Lee
  • Younghee Park
  • Yoongho Lim
  • Joong-Hoon Ahn
Article

Abstract

Enzymatic O-methylation, catalyzed by S-adenosyl-L-methionine (SAM)-dependent O-methyltranferases (OMTs), is a ubiquitous reaction, occurring in almost all living organisms. Plant OMTs are involved in the methylation of secondary metabolites, including phenylpropanoid and flavonoid compounds. Here, we used RT-PCR to isolate and characterizePOMT-2 fromPopulus deltoides. This OMT comprises a 1095-b open reading frame that encodes a 39.7-kDa protein. BLAST results showed 87% identities to an OMT fromPrunus dulcis and a caffeic acid OMT fromRosa chinensis. POMT-2 was expressed inEscherichia coli as a glutathione S-transferase fusion protein, and was purified by affinity chromatography. POMT-2 transferred a methyl group of SAM to caffeic acid and 6,7-dihydroxyflavone, but showed low activities toward quercetin and kaempferol. According to itsin vitro substrate preference and composition of phenolic compounds in poplar, thein vivo function of POMT-2 is probably the methylation of caffeic acid and an involvement in lignin biosynthesis.

Keywords

caffeic acid flavonoids O-methyltransferase 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. Chappie C (1998) Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenase. Annu Rev Plant Physiol Plant Mol Biol49: 311–343CrossRefGoogle Scholar
  2. Frick S, Kutchan TM (1999) Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J17: 329–339PubMedCrossRefGoogle Scholar
  3. Gauthier A, Gulick PJ, Ibrahim RK (1998) Characterization of two cDNA clones which encode O-methyltransferases for the methylation of both flavonoid and phenylpropanoid compounds. Arch Biochem Biophys351: 243–249PubMedCrossRefGoogle Scholar
  4. Goujon T, Sibout R, Pollet B, Maba B, Nussaume L, Bechtold N, Lu F, Ralph J, Mila I, Barriere Y, Lapierre C, Jouanin L (2003) A newArabidopsis thaliana mutant deficient in the expression of O-methyltransferase impacts lignins and sinapoyl esters. Plant Mol Biol51: 973–989PubMedCrossRefGoogle Scholar
  5. Ibrahim RK, Bruneau A, Bantignies B (1998) Plant O-methyltransferases: Molecular analysis, common signature and classification. Plant Mol Biol36: 1–10PubMedCrossRefGoogle Scholar
  6. Inoue K, Parvathi K, Dixon RA (2000) Substrate preferences of caffeic acid/5 hydroxyferulic acid 3/5-O-methyltransferases in developing stems of alfalfa (Medicago sativa L). Arch Biochem Biophys375: 175–182PubMedCrossRefGoogle Scholar
  7. Kim BG, Kim DH, Hur H-G, Lim J, Lim Y, Ahn J-H (2005) O-Methyltransferases fromArabidopsis thaliana. Agric Chem Biotechnol48: 113–119Google Scholar
  8. Kim BG, Kim SY, Song HS, Lee C, Hur HG, Kim SI, Ahn J-H (2003) Cloning and expression of the isoflavone synthase gene fromTrifolium pratense. Mol Cells15: 301–306PubMedGoogle Scholar
  9. Kim DH, Kim BG, Lee Y, Ryu JY, Lim Y, Hur H-G, Ahn J-H (2005) Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed inEscherichia coli. J Biotech119: 155–162CrossRefGoogle Scholar
  10. Kota P, Guo D, Zubieta C, Noel J, Dixon RA (2004) O-Methylation of benzaldehyde derivatives by “lignin specific” caffeic acid 3-O-methyltransferase. Phytochem65: 837–846CrossRefGoogle Scholar
  11. Muzac I, Wang J, Anzellotti D, Zhang H, Ibrahim RK (2000) Functional expression of anArabidopsis cDNA clone encoding a flavonol 3′-O-methyltransferase and characterization of the gene product. Arch Biochem Biophys375: 385–388PubMedCrossRefGoogle Scholar
  12. Neish AC (1968) Monomeric intermediates in the biosynthesis of lignin,In K Freudenberg, AC Neish, eds, Constitution and Biosynthesis of Lignin. Springer-Verlag, Berlin, pp 243Google Scholar
  13. Park HJ, Min BM, Cha HC (2003) Flavonoid analysis ofHeloniopsis orientalis (Thunb.) by high performance liquid chromatography. J Plant Biol46: 250–254CrossRefGoogle Scholar
  14. Warren JM, Bassman JH, Fellman JK, Martinson DS, Eigenbrode S (2003) Ultraviolet-B radiation alters phenolic salicylate and flavonoid composition ofPopulus trichocarpa leaves. Tree Physiol23: 527–535PubMedGoogle Scholar
  15. Whetten RW, Mackay JJ, Sederoff RR (1998) Recent advances in understanding lignin biosynthesis. Annu Rev Plant Physiol Plant Mol Biol49: 585–609PubMedCrossRefGoogle Scholar
  16. Yang DH, Chung BY, Kim JS, Kim JH, Yun PY, Lee YK, Lim YP, Lee C (2005) cDNA cloning and sequence analysis of the rice cinnamate-4-hydroxylase gene, a cytochrome P450-dependent monooxygenase involved in the general phenylpropanoid pathway. J Plant Biol48: 311–318CrossRefGoogle Scholar
  17. Ye ZH, Zhong R, Morrison WH III, Himmelsbach DS (2001) Caffeoyl coenzyme A O-methyltransferase and lignin biosynthesis. Phytochem57: 1177–1185CrossRefGoogle Scholar
  18. Zubieta C, He XZ, Dixon RA, Noel JP (2001) Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases. Nat Struct Biol8: 271–279PubMedCrossRefGoogle Scholar
  19. Zubieta C, Kota P, Ferer J-L, Dixon RA, Noel JP (2002) Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase. Plant Cell14: 1265–1277PubMedCrossRefGoogle Scholar

Copyright information

© The Botanical Society of Korea 2006

Authors and Affiliations

  • Bong Gyu Kim
    • 1
  • Yoon Jung Lee
    • 1
  • Younghee Park
    • 1
  • Yoongho Lim
    • 1
  • Joong-Hoon Ahn
    • 1
  1. 1.Bio/Molecular Informatics CenterKonkuk UniversitySeoulKorea

Personalised recommendations