Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis

Journal of Bioscience and Bioengineering

Volumn 96, Issue 2, 2003, Pages 119-128

  Wu, Shuiqin ^a   Watanabe, Naoharu ^a   Mita, Satoru ^a   Ueda, Yoshihiro ^b   Shibuya, Masaaki ^c   Ebizuka, Yutaka ^c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

1,3,5 trimethoxybenzene; Isomethyleugenol; Methyleugenol; O methyltransferase; Rosa chinensis var. spontanea

Indexed keywords

BENZENE; ENZYMES; RNA; TISSUE;

HOMOLOGY;

BIOSYNTHESIS;

CAFFEIC ACID; CATECHOL METHYLTRANSFERASE; EUGENOL; ISOEUGENOL; METHYLTRANSFERASE; RNA;

ARTICLE; COMPARATIVE STUDY; ENZYME ACTIVITY; ENZYME CHEMISTRY; FLOWER; METHYLATION; ODOR; PETAL; PRUNUS; RNA TRANSCRIPTION; ROSE; SCREENING TEST; VARIETAS; VOLATILIZATION;

PRUNUS; PRUNUS DULCIS; ROSA; ROSA CHINENSIS; ROSA CHINENSIS VAR. SPONTANEA;

EID: 0041876084     PISSN: 13891723     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1389-1723(03)90113-7     Document Type: Article

References (37)

1. Rehder, A.: Manual of cultivated trees and shrubs hardy in North America, 2nd ed., p. 426-451. MacMillan, New York (1940).
2. Cairns, T.: Modern roses XI. Academic Press, San Diego (2000).
3. Wylie, A. P.: The history of garden roses (part I). J. R. Hort. Soc., 79, 555-571 (1954).
4. Rougetel, H. L.: A heritage of roses, p. 42-50. Unwin Hyman, London (1988).
5. Ogisu, M.: Some thoughts on the history of China roses. New Plantsman, 3, 152-157 (1996).
6. Yomogida, K.: Scent of modern roses. Kouryo, 175, 65-89 (1992).
7. Watanabe, N., Washio, H., Straubinger, M., Knapp, H., and Winterhalter, P.: Occurrence of a glucosidic progenitor of rose oxide in rose flowers, Rosa damascena Mill. Nat. Prod. Lett., 12, 5-10 (1998).
8. Lavid, N., Wang, J., Shalit, M., Guterman, I., Bar, E., Beuerle, T., Menda, N., Shafir, S., Zamir, D., Adam, Z., Vainstein, A., Weiss, D., Pichersky, E., and Lewinsohn, E.: O-Methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Plant Physiol., 129, 1899-1907 (2002).
9. Scalliet, G., Journot, N., Jullien, F., Baudino, S., Magnard, J. L., Channeliere, S., Vergne, P., Durmas, C., Bendahmane, M., Cock, J. M., and Hugueney, P.: Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases. FEBS Lett., 523, 113-118 (2002).
10. Hahlbrock, K. and Scheel, D.: Physiology and molecular biology of phenylpropanoid metabolism. Annu. Rev. Plant Physiol. Plant Mol. Biol., 40, 347-369 (1989).
11. Obeng-Ofori, D. and Reichmuth, C.: Bioactivity of eugenol, a major component of essential oil of Ocimum suave (Wiild.) against four species of stored product Coleoptera. Int. J. Pest. Manage., 43, 89-94 (1997).
12. Shukla, R. and Prasad, V.: Population fluctuations of the oriental fruit fly, Dacus dorsalis Hendel. In relation to hosts and abiotic factors. Trop. Pest. Manage., 31, 273-275 (1985).
13. Gowri, G., Bugos, R. C., Campbell, W. H., Maxwell, C. A., and Dixon, R. A.: Stress responses in alfalfa (Medicago sativa L.) X. Molecular cloning and expression of S-adenosyl-L-methionine: caffeic acid 3-O-methyltransferase, a key enzyme of lignin biosynthesis. Plant Physiol., 97, 7-14 (1991).
14. Ye, Z. H. and Varner, J. E.: Differential expression of two O-methyltransferases in lignin biosynthesis in Zinnia elegans. Plant Physiol., 108, 459-467 (1995).
15. Inoue, K., Sewalt, V. J. H., Ballance, G. M., Ni, W., Sturzer, C., and Dixon, R. A.: Developmental expression and substrate specificities of alfalfa caffeic acid 3-O-methyltransferase and caffeoyl coenzyme A 3-O-methyltransferase in relation to lignification. Plant Physiol., 117, 761-770 (1998).
16. Wu, Q., Preisig, C. L., and VanEtten, H. D.: Isolation of the cDNAs encoding (+)6a-hydroxymaackiain 3-O-methyltransferase, the terminal step for the synthesis of the phytoalexin pisatin in Pisum satvium. Plant Mol. Biol., 35, 551-560 (1997).
17. Christensen, A. B., Gregersen, P. L., Olsen, C. E., and Collinge, D. B.: A flavonoid 7-O-methyltransferase is expressed in barley leaves in response to pathogen attack. Plant Mol. Biol., 36, 219-227 (1998).
18. Wang, J., Dudareva, N., Bhakta, S., Raguso, R. A., and Pichersky, E.: Floral scent production in Clarkia breweri (onagraceae). II. Localization and developmental modulation of the enzyme S-adenosyl-L-methionine: (iso)eugenol O-methyltransferase and phenylpropanoid emission. Plant Physiol., 114, 213-221 (1997).
19. Lewinsohn, E., Ziv-Raz, I., Dudai, N., Tadmor, Y., Lastochkin, E., Larkov, O., Chaimovitsh, D., Ravid, U., Putievsky, E., Pichersky, E., and Shoham, Y.: Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L.). Developmental and chemotypic association of allyphenol O-methyltransferase activities. Plant Sci., 160, 27-35 (2000).
20. Gang, D. R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J. P., and Pichersky, E.: Characterization of phenylpropene O-methyltransferases from sweet basil: facil change of substrate specificity and convergent evolution within a plant O-methyltrasferase family. Plant Cell, 14, 505-519 (2002).
21. Ross, J. R., Nam, K. H., D'Auria, J. C., and Pichersky, E.: S-Adenosyl-L-methionine: salicylic acid carboxyl methyltransferase, an enzyme involved in floral scent production and plant defense, represents a new class of plant methyltransferases. Arch. Biochem. Biophys., 367, 9-16 (1999).
22. Dudareva, N., Raguso, R. A., Wang, J., Ross, J. R., and Pichersky, E.: Floral scent production in Clarkia breweri (onagraceae). III. Enzymatic synthesis and emission of benzenoid esters. Plant Physiol., 116, 599-604 (1998).
23. Dudareva, N., Murfitt, L. M., Mann, C. J., Gorenstein, N., Kolosova, N., Kish, C. M., Bonham, C., and Wood, K.: Developmental regulation of methyl benzoate biosynthesis and emission in snapdragon flowers. Plant Cell, 12, 949-961 (2000).
24. Ibrahim, R. K., Bruneau, A., and Bantignies, B.: Plant O-methyltransferases: molecular analysis, common signature and classification. Plant Mol. Biol., 36, 1-10 (1998).
25. 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).
26. Gauthier, A., Gulick, P. J., and Ibrahim, R. K.: Characterization of two cDNA clones which encode O-methyltransferases for the methylation of both flavonoid and phenylpropanoid compounds. Arch. Biochem. Biophys., 351, 243-249 (1998).
27. Kagan, R. M. and Clarke, S.: Widespread occurrence of three sequence motifs in diverse S-adenosylmethionine-dependent methyltransferases suggests a common structure for these enzymes. Arch. Biochem. Biophys., 310, 417-427 (1994).
28. Zubieta, C., He, X. Z., Dixon, R. A., and Noel, J. P.: Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferase. Nat. Struct. Biol., 8, 271-279 (2001).
29. Schroder, G., Wehinger, E., and Schroder, J.: Predicting the substrates of cloned plant O-methyltransferases. Phytochemistry, 59, 1-8 (2002).
30. Oka, N., Ohishi, H., Hatano, T., Hornberger, M., Sakata, K., and Watanabe, N.: Aroma evolution during flower opening in Rosa damascena Mill. Z. Naturforsch., 54c, 889-895 (1999).
31. Frohman, M. A., Dush, M. K., and Martin, G. R.: Rapid production of full-length cDNAs from rare transcripts: amplification using a single gene-specific oligonucleotide primer. Proc. Natl. Acad. Sci. USA, 85, 8998-9002 (1988).
32. Wang, J. and Pichersky, E.: Characterization of S-adenosyl-L-methionine: (iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri. Arch. Biochem. Biophys., 349, 153-160 (1998).
33. 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, 248-254 (1976).
34. Yokoi, H., Natsuyama, S., Iwai, M., Noda, Y., Mori, T., Mori, K. J., Fujita, K., Nakayama, H., and Fujita, J.: Non-radioisotopic quantitative RT-PCR to detect changes in mRNA levels during early mouse embryo development. Biochem. Biophys. Res. Commun., 195, 769-775 (1993).
35. Dobson, H. E. M., Bergstroem, G., and Groth, I.: Differences in fragrance chemistry between flower parts of Rosa rugosa Thunb (Rosaceae). Isr. J. Bot., 39, 143-156 (1990).
36. Wein, M., Lavid, N., Lunkenbein, S., Lewinsoln, E., Schwab, W., and Kaldenolf, R.: Isolation, cloning and expression of a multifunctional O-methyltransferase capable of forming 2,5-dimethyl-4-methoxy-3(2H)-furanone, one of the key aroma compounds in strawberry fruits. Plant J., 31, 755-765 (2002).
37. Suelves, M. and Puigdomenech, P.: Specific mRNA accumulation of a gene coding for an O-methyltransferase in almond (Prunus amygdalus, Batsch) flower tissues. Plant Sci., 134, 79-88 (1998).