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Bioscience, Biotechnology, and Biochemistry Volume 65, 2001 - Issue 10
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Original Articles

Purification and Characterization of a O-Methyltransferase Capable of Methylating 2-Hydroxy-3-alkylpyrazine from Vitis vinifera L. (cv. Cabernet Sauvignon)

Katsumi HASHIZUMENational Research Institute of Brewing
,
Kazuyuki TOZAWANational Research Institute of Brewing
,
Yoshikazu HIRAGADepartment of Chemistry, Graduate School of Science, Hiroshima University
&
Isao ARAMAKINational Research Institute of Brewing
Pages 2213-2219 | Received 30 Mar 2001, Accepted 19 Jun 2001, Published online: 22 May 2014

  • 1) Rizzi, G.P., The biogenesis of food-related pyrazines. Food Reviews International, 4, 375-400 (1988).
  • 2) Seifert, R.M., Buttery, R.G., Guadagni, D.G., Black, D.R., and Harris, J.G., Synthesis of some 2-methoxy-3-alkylpyrazines with strong bell pepper-like odors. J. Agric. Food Chem., 18, 246-249 (1970).
  • 3) Murray, K.E. and Whitfield, F.B., The occurrence of 3-alkyl-2-methoxypyrazines in raw vegetables. J. Sci. Fd Agric., 26, 973-986 (1975).
  • 4) Allen, M.S., Lacey, M.J., Harris, R.L.N., and Brown, W.V., Contribution of methoxypyrazines to Sauvignon blanc wine aroma., Am. J. Enol. Vitic., 42, 109-112 (1991).
  • 5) Allen, M.S., Lacey, M.J., and Boyd, S., Determination of methoxypyrazines in red wines by stable isotope dilution gas chromatography-mass spectrometry. J. Agric. Food Chem., 42, 1734-1738 (1994).
  • 6) Hashizume, K. and Umeda, N., Methoxypyrazine content of Japanese red wines. Biosci. Biotechnol. Biochem., 60, 802-805 (1996).
  • 7) Allen, M., What level of methoxypyrazines is desired in red wines? The flavour perspective of the classic red wines of Bordeaux. Aust. Grapegrower Winemaker, 381, 7-9 (1995).
  • 8) Hashizume, K. and Samuta, T., Green odorants of grape cluster stem and their ability to cause a wine stemmy flavor. J. Agric. Food Chem., 45, 1333-1337 (1997).
  • 9) McIver, R.C. and Reineccius, G.A., Synthesis of 2-methoxy-3-alkylpyrazines by Pseudomonas perolens. In “ACS Symposium Series 317”, eds. Parliament, T.H. and Croteau, R., Am. Chem. Soc. Washington, pp. 266-274 (1986).
  • 10) Gallois, A., Kergomard, A., and Adda, J., Study of the biosynthesis of 3-isopropyl-2-methoxypyrazine produced by Pseudomonas taetrolens. Food Chemistry, 28, 299-309 (1988).
  • 11) Rizzi, G.P., Formation of methoxypyrazines in reaction of 2(1H)-pyrazinones with naturally occurring methylating agents. J. Agric. Food Chem., 38, 1941-1944 (1990).
  • 12) Hashizume, K., Tozawa, K., Endo, M., and Aramaki, I., S-Adenosyl-L-methionine-dependent O-Methylation of 2-Hydroxy-3-alkylpyrazine in Wine Grapes: A Putative Final step of Methoxypyrazine Biosynthesis. Biosci. Biotechnol. Biochem., 65, 795-801 (2001).
  • 13) Fauman, E.B., Blumenthal, R.M., and Cheng, X., Structure and evolution of AdoMet-dependent methyltransferase. In “S-adenosylmethionine-dependent methyltranferase: structure and functions”. Eds. Cheng, X. and Blumenthal, R.M., World Scientific, Singapore, pp. 1-38 (1999).
  • 14) Bradford, M.M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72, 248-354 (1976).
  • 15) Ibrahim, R.K., Bruneau, A., and Bantignies, B., Plant O-methyltransferase: molecular analysis, common signature and classification. Plant Molecular Biology, 36, 1-10 (1998).
  • 16) Mbeguie-A-Mbeguie, D., Gomez, R.-M., and Fils-Lycaon, B., Sequence of an O-Methyltransferase from Apricot Fruit (Accession No. U82011). Gene Expression during Fruit Ripening. Plant Physiol., 114, 1569 (1997).
  • 17) Li, L., Popko, J.L., Zhang, X., Osakabe, K,. Tsai, C., Joshi C.P., and Chiang, V.L., A novel multifunctional O-methyltransferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. Proc. Natl. Acad. Sci. USA, 94, 5461-5466 (1997).
  • 18) Moyle, R., Wagner, A., and Water, C., Nucleotide Sequence of a Caffeic Acid O-Methyltransferase Gene (Accession No. F119225) from Pinus radiata. Plant Pysiol., 119, 1147 (1999).
  • 19) Hermann, C., Legrand, M., Geoffroy, P., and Fritig, B., Enzymatic synthesis of lignin: purification to homogeneity of the three O-methyltransferase of tobacco and production of specific antibodies. Arch. Biochem. Biophys., 253, 367-376 (1987).
  • 20) Preisig, C.L., Matthews, D.E., and VanEtten H.D., Purification and characterization of S-adenosyl-L-methionine: 6a-hydroxymaackiain 3-O-methyltransferase from Pisum sativum. Plant Physiol., 91, 559-566 (1989).
  • 21) Frenzel, T. and Zenk, M.H., S-Adenosyl-L-methionine: 3'-hydroxy-N-methyl-(S)-coclaurin-4'-O-methyltransferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway. Phytochemistry, 29, 3505-3511 (1990).
  • 22) Maxwell, C.A., Edwards, R., and Dixon, R.A., Identification, purification, and characterization of S-adenosyl-L-methionine: isoliquiritigenin 2'-O-methyltransferase from alfalfa (Medicago sativa L.). Arch. Biochem. Biophys., 293, 158-166 (1992).
  • 23) Sato, F., Takeshita, N., Fitchen, J.H., Fujiwara, H., and Yamada, Y., S-Adenosyl-L-methionine:scoulerine-9-O-methyltransferase from cultured Coptis japonica cells. Phytochemistry, 32, 659-664 (1993).
  • 24) Sato, F., Tsujita, T., Katagiri, Y., Yosida, S., and Yamada, Y., Purification and characterization of S-Adenosyl-L-methionine: norcoclaurine 6-O-methyltransferase from cultured Coptis japonica cells. Eur. J. Biochem., 225, 125-131 (1994).
  • 25) Pakusch, A.E., Matern, U., and Schiltz, E,. Elicitorinducible caffeoyl-coenzyme A 3-O-methyltransferase from Petroselium crispum cell suspensions. Plant Physiol., 95, 137-143 (1991).
  • 26) Liu, J., Benedict, C.R., Stipanovic, R.D., and Bell, A.A., Purification and Characterization of S-Adenosyl-L-Methionine: Desoxyhemigossypol-6-O-Methyltransferase from Cotton Plants. An Enzyme Capable of Methylating the Defense Terpenoids of Cotton. Plant Physiol., 121, 1017-1024 (1999).
  • 27) Meng, H. and Campbell, W.H., Characterization and Site-Directed Mutagenesis of Aspen Lignin-Specific O-methyltransferase Expressed in Escherichia coli. Arch. Biochem. Biophys., 330, 329-341 (1996).
  • 28) Doorsselaere, J.V., Dumas, B., Baucher, M., Fritig, B., Legrand, M., Montagu, M.V., and Inze, D., One-step purification and characterization of a lignin-specific O-methyltransferase from poplar. Gene, 133, 213-217 (1993).
  • 29) Chiron, H., Drouet, A., Claudot, A.-C, Eckerskorn, C., Trost, M., Heller, W,. Ernst, D., and Sandermann Jr, H., Molecular cloning and functional expression a stress-induced multifunctional O-methyltransferase with pinosylvin methyltransferase activity from Scots pine (Pinus sylvestris L.). Plant Molecular Biology, 44, 733-745 (2000).
  • 30) Joshi, C.P. and Chang, V.L., Conserved sequence motifs in plant S-Adenosyl-L-Methionine-dependent O-methyltransferases. Plant Molecular Biology, 37, 663-674 (1998).
  • 31) Ebel, J., Hahlbrock, K., and Grisebach, H., Purification and properties of an o-dihydriphenol meta-O-methyltransferase from cell suspension cultures of parsley and its relation to flavonoid biosynthesis. Biochim. Biophys. Acta, 269, 313-326 (1972).
  • 32) Poulton, J.E., Hahlbrock, K., and Grisebach, H., O-Methylation of flavonoid substrates by a partially purified enzyme from soybean cell suspension cultures. Arch. Biochem. Biophys., 180, 543-549 (1977).
  • 33) Pakusch, A.E., Kneusel, R.E., and Matern, U., S-Adenosyl-L-Methionine:trans-Caffeoyl-coenzyme A 3-O-Methyltransferase from Elicitor-Treated Parsley Cell Suspension Cultures. Arch. Biochem. Biophys., 271, 488-494 (1989).
  • 34) Attieh, J.M., Hanson, A.D., and Saini, H.S., Purification and characterization of a novel methyltransferase responsible for biosynthesis of halomethanes and methanethiol in Brassia oleracea. J. Biol. Chem., 270, 9250-9257 (1995).

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