Skip to main content
SpringerLink
Log in

Cation dependent O-methyltransferases from rice

  • Original Article
  • Published:
Planta Aims and scope Submit manuscript

Abstract

Two lower molecular mass OMT genes (ROMT-15 and -17) were cloned from rice and expressed in Escherichia coli as glutathione S-transferase fusion proteins. ROMT-15 and -17 metabolized caffeoyl-CoA, flavones and flavonols containing two vicinal hydroxyl groups, although they exhibited different substrate specificities. The position of methylation in both luteolin and quercetin was determined to be the 3′ hydroxyl group and myricetin and tricetin were methylated not only at 3′ but also at 5′ hydroxyl groups. ROMT-15 and -17 are cation-dependent and mutation of the predicted metal binding sites resulted in the loss of the enzyme activity, indicating that the metal ion has a critical role in the enzymatic methylation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Abbreviations

AdoMet:

S-adenosyl methionine

CCoA:

Caffeoyl-CoA

CCoAOMT:

Caffeoyl coenzyme A OMT

GST:

Gluthathione S-transferase

5HFA:

5-Hydroxyferulic acid

OMT:

O-methyltransferase

References

  • Bichoff EM, Livingston AL, Booth AN (1964) Tricin from alfalfa: isolation and physiological activity. J Pharm Sci 53:1411–1412

    Article  Google Scholar 

  • Cacace S, Schröder G, Wehinger GE, Strack D, Schmidt J, Schröder J (2003) A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations. Phytochemistry 62:127–137

    Article  PubMed  CAS  Google Scholar 

  • Cai H, Hudson EA, Mann P, Verschoyle RD, Greaves P, Manson MM, Stepward WP, Gescher AJ (2004) Growth-inhibitory and cell cycle-arresting properties of the rice bran constituent in human-derived breast cancer cells in vitro and in nude mice in vivo. Br J Cancer 91:1364–1371

    Article  PubMed  CAS  Google Scholar 

  • Civardi L, Rigau J, Puigdomenech P (1999) Nucleotide sequence of two cDNAs for caffeoyl-coenzyme A O-methyltransferase (CCoAOMT) and study of their expression in Zea mays (Accession Nos. AJ242980 and AJ242981). Plant Physiol 120:1206

    Google Scholar 

  • Dixon RA, Paiva NC (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085–1097

    Article  PubMed  CAS  Google Scholar 

  • Ferrer F-L, Zubieta C, Dixon RA, Noel JP (2005) Crystal structures of alfalfa caffeoyl coenzyme A 3-O-methyltransferase. Plant Physiol 137:1009–1017

    Article  PubMed  CAS  Google Scholar 

  • Hibasami H, Mitani A, Katsuzaki H, Imai K, Yoshioka K, Komiya T (2005) Isolation of five types of flavonol from seabuckthorn (Hippophae rhamnoides) and induction of apoptosis by some of the flavonols in human promyelotic leukemia HL-60 cells. Int J Mol Med 15:805–809

    PubMed  CAS  Google Scholar 

  • Horner L, Teichmann KH, Weber KH, Geyer E (1965) O-Quinones. XXV. Preparation and properties of O-quinones with electrophilic substituents. Chem Ber 98:1233–1245

    Article  CAS  Google Scholar 

  • Hudson EA, Dinh PA, Kokubun T, Simmonds MSJ, Gescher A (2000) Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Cancer Epidemiol Biomarkers Prev 9:1163–1170

    PubMed  CAS  Google Scholar 

  • Ibdah M, Zhang X-H, Schnot J, Vogt T (2003) A novel Mg2+-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum. J Biol Chem 278:43961–43972

    Article  PubMed  CAS  Google Scholar 

  • Ibrahim RK, Anzellotti D (2003) The enzymatic basis of flavonoid biodiversity. In: Romeo JT (ed) Integrative phytochemistry: from ethnobotany to molecular ecology. Pergamon, New York, pp 1–36

    Google Scholar 

  • Ibrahim RK, De Luca V, Khouri H, Latchinian L, Brisson L, Charest PM (1987) Enzymology and compartmentation of polymethylated flavonol glucosides in Chrysosplenium americanum. Phytochemistry 26:1237–1245

    Article  Google Scholar 

  • Ibrahim RK, Bruneau A, Bantignies B (1998) Plant O-methyltransferase: molecular analysis, common signature and classification. Plant Mol Biol 36:1–10

    Article  PubMed  CAS  Google Scholar 

  • Joshi CP, Chiang VL (1998) Conserved sequence motifs in plant S-adenosyl-l-methionine-dependent methyltransferases. Plant Mol Biol 37:663–674

    Article  PubMed  CAS  Google Scholar 

  • Kim BG, Ko JH, Min SY, Ahn JH (2005a) Classification and expression profiling of putative R2R3 MYB genes in rice. Agric Chem Biotechnol 48:127–132

    CAS  Google Scholar 

  • Kim DH, Kim BG, Lee Y, Ryu JY, Lim Y, Hur H-G, Ahn J-H (2005b) Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. J Biotechnol 138:155–162

    Article  CAS  Google Scholar 

  • Kim BG, Lee Y, Hur H-G, Lim Y, Ahn J-H (2006a) Flavonoid 3′-O-methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry 67:387–394

    Article  PubMed  CAS  Google Scholar 

  • Kim JH, Kim BG, Park Y, Han JH, Lim Y, Ahn J-H (2006b) Production of 5,7-dihydroxy, 3′,4′,5′- trimethoxyflavone from 5,7,3′,4′,5′-pentahydroxyflavone using two O-methyltransferases expressed in Escherichia coli. Agric Chem Biotechnol 49:114–116

    CAS  Google Scholar 

  • Kumar S, Tamura K, Nei M (2004) MEGA3: integrated software for molecular evolutionary genetics analysis and sequence alignment. Brief Bioinform 5:150–163

    Article  PubMed  CAS  Google Scholar 

  • Laskowski RA, MacArthur MW, Moss DS, Thornton JM (1993) PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Crystallogr 26:283–291

    Article  CAS  Google Scholar 

  • Lee YJ, Kim BG, Park Y, Lim Y, Hur H-G, Ahn J-H (2006) Biotransformation of flavonoids with O-methyltransferase from Bacillus cereus. J Microbiol Biotechnol 16:1090–1096

    CAS  Google Scholar 

  • Lee YJ, Jeon Y, Lee JS, Kim BG, Lee CH, Ahn J-H (2007) Enzymatic synthesis of phenolic CoAs using 4-coumarate:coenzyme A ligase (4CL) from rice. Bull Korean Chem Soc 28:365–366

    Article  CAS  Google Scholar 

  • Lin F, Yamano G, Hasegawa M, Anzai H, Kawasaki S, Kodama O (2006) Cloning and functional analysis of caffeic acid 3-O-methyltransferase from rice (Oryza sativa). J Pestic Sci 31:47–53

    Article  CAS  Google Scholar 

  • Markham KR, Tanner GJ, Caasi-List M, Whiecross MI, Nayudu M, Mitchell KA (1998) Possible protective role for 3′,4′-dihydroxyflavones induced by enhanced UV-B in a UV-tolerant rice cultivar. Phytochemistry 49:1913–1919

    Article  CAS  Google Scholar 

  • Nathan RG, Stermitz FR (2000) Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans. J Nat Prod 63:1140–1145

    Article  CAS  Google Scholar 

  • Vogt R (2004) Regiospecificity and kinetic properties of a plant natural product O-methyltransferase are determined by its N-terminal domain. FEBS Lett 561:159–162

    Article  PubMed  CAS  Google Scholar 

  • Yoon Y, Yi YS, Lee Y, Kim S, Kim BG, Ahn J-H, Lim Y (2005) Characterization of O-methyltransferase ScOMT1 cloned from Streptomyces coelicolor A3(2). Biochim Biophys Acta 1730:85–95

    PubMed  CAS  Google Scholar 

  • Zhou J-M, Gold ND, Martin VJJ, Wollenweber E, Ibrahim RK (2006a) Sequential O-methylation of tricetin by a single gene product in wheat. Biochim Biophys Acta 1760:1115–1124

    PubMed  CAS  Google Scholar 

  • Zhou J-M, Fukushi Y, Wang X, Ibrahim RK (2006b) Characterization of a novel flavone O-methyltransferase gene in rice. Nat Prod Commun 1:981–984

    Article  CAS  Google Scholar 

  • Zhu BT, Ezell EL, Liehr JG (1994) Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo. J Biol Chem 269:292–299

    PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a grant from the Biogreen 21 Program, Rural Development Administration, Republic of Korea and partially by grant KRF-2006-005-J03401and the second Brain Korea 21 (Ministry of Education).

Author information

Authors and Affiliations

  1. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, 143-701, South Korea

    Yoon Jung Lee, Bong Gyu Kim, Youhoon Chong, Yoongho Lim & Joong-Hoon Ahn

Authors
  1. Yoon Jung Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bong Gyu Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Youhoon Chong
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yoongho Lim
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Joong-Hoon Ahn
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Joong-Hoon Ahn.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lee, Y.J., Kim, B.G., Chong, Y. et al. Cation dependent O-methyltransferases from rice. Planta 227, 641–647 (2008). https://doi.org/10.1007/s00425-007-0646-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00425-007-0646-4

Keywords

Search

Navigation