(R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy

Plant Journal

Volumn 36, Issue 6, 2003, Pages 808-819

  Ounaroon, Anan ^a,c   Decker, Gabriele ^b   Schmidt, Jürgen ^a   Lottspeich, Friedrich ^b   Kutchan, Toni M ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

^c NARESUAN UNIVERSITY   (Thailand)

Author keywords

(R,S) reticuline 7 O methyltransferase; Alkaloid biosynthesis; Norcoclaurine 6 O methyltransferase; Opium poppy; Papaver somniferum

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; MASS SPECTROMETRY; PLANTS (BOTANY); PROTEINS; REACTION KINETICS; RNA;

METHYLATION; PROTEOMIC ANALYSIS;

ENZYME KINETICS;

ALKALOID; COMPLEMENTARY DNA; METHYLTRANSFERASE; OPIATE; PEPTIDE FRAGMENT; RECOMBINANT PROTEIN; S ADENOSYL L METHIONINE (R,S) RETICULINE 7 O METHYLTRANSFERASE; S ADENOSYL L METHIONINE NORCOCLAURINE 6 O METHYLTRANSFERASE; S-ADENOSYL-L-METHIONINE (R,S)-RETICULINE 7-O-METHYLTRANSFERASE; S-ADENOSYL-L-METHIONINE-NORCOCLAURINE 6-O-METHYLTRANSFERASE;

AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; CHEMISTRY; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PAPAVER; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY;

ALKALOIDS; AMINO ACID SEQUENCE; CLONING, MOLECULAR; CONSERVED SEQUENCE; DNA, COMPLEMENTARY; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; METHYLTRANSFERASES; MOLECULAR SEQUENCE DATA; OPIUM; PAPAVER; PEPTIDE FRAGMENTS; RECOMBINANT PROTEINS; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY, AMINO ACID;

ANIMALIA; COPTIS; COPTIS JAPONICA; JAPONICA; PAPAVER; PAPAVER SOMNIFERUM; SPODOPTERA; SPODOPTERA FRUGIPERDA; THALICTRUM; THALICTRUM TUBEROSUM; UNIDENTIFIED BACULOVIRUS; VECTORS;

EID: 0347317979     PISSN: 09607412     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-313X.2003.01928.x     Document Type: Article

References (30)

1. Antoun, M.D. and Roberts, M.F. (1975a) Some enzymes of general metabolism in the latex of Papaver somniferum. Phytochemistry, 14, 909-914.
2. Antoun, M.D. and Roberts, M.F. (1975b) Enzymic studies with Papaver somniferum. Part 5. The occurrence of methyltransferase enzymes in poppy latex. Planta Med. 28, 6-11.
3. Bracher, D. and Kutchan, T.M. (1992) Strictosidine synthase from Rauvolfia serpentina. Analysis of a gene involved in indole alkaloid biosynthesis. Arch. Biochem. Biophys. 294, 717-723.
4. Cacace, S., Schröder, G., Wehinger, E., Strack, D., Schmidt, J. and Schröder, J. (2003) A flavonol O-methyltransferase from Catharanthus roseus performing two sequencial methylations. Phytochemistry, 62, 127-137.
5. Decker, G., Wanner, G., Zenk, M.H. and Lottspeich, F. (2000) Characterization of the proteins in latex of the opium poppy (Papaver somniferum) using two-dimensional gel electrophoresis and microsequencing. Electrophoresis, 21, 3500-3516.
6. Dittrich, H. and Kutchan, T.M. (1991) Molecular cloning, expression and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack. Proc. Natl. Acad. Sci. USA, 88, 9969-9973.
7. Facchini, P.J., Penzes, C., Johnson, A.G. and Bull. D. (1996) Molecular characterization of berberine bridge enzyme genes from opium poppy. Plant Physiol. 112, 1669-1677.
8. Frick, S. and Kutchan, T.M. (1999) Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J. 17, 329-339.
9. Gamborg, O.L., Miller, R.A. and Ojina, K. (1968) Nutrient requirements of suspension cultures of soybean root cells. Exp. Cell. Res. 50, 151-158.
10. Gang, D.R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J.P. and Pichersky, E. (2002) Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of a substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell, 14, 505-519.
11. Ghosal, S., Majumdar, S.K. and Chakraborti, A. (1971) Erythrina alkaloids. Part III. Occurrence of N-norprotosinomenine and other alkaloids in Erythrina lithosperma (Leguminosae). Aust. J. Chem. 24, 2733-2735.
12. Grothe, T., Lenz, R. and Kutchan, T.M. (2001) Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem. 276, 30717-30723.
13. Huang, F.-C. and Kutchan, T.M. (2000) Distribution of morphinan and benzophenanthridine alkaloid gene transcript accumulation in the opium poppy Papaver somniferum. Phytochemistry, 53, 555-564.
14. Ibrahim, R.K., Bruneau, A. and Bantignies, B. (1998) Plant O-methyltransferases: molecular analyses, common signature and classification. Plant Mol. Biol. 36, 1-10.
15. Joshi, C.P. and Chiang, V.L. (1998) Conserved sequence motifs in plant S-adenosyl-L-methionine-dependent methyltransferases. Plant Mol. Biol. 37, 663-674.
16. Kutchan, T.M. (1998) Molecular genetics of plant alkaloid biosynthesis. In The Alkaloids, Vol. 50 (Cordell, G., ed.). San Diego: Academic Press, pp. 257-316.
17. Kutchan, T.M., Bock, A. and Dittrich, H. (1994) Heterologous expression of strictosidine synthase and berberine bridge enzyme in insect cell culture. Phytochemistry, 35, 353-360.
18. Lavid, N., Wang, J., Shalit, M. et al. (2002) O-Methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Plant Physiol. 129, 1899-1907.
19. Li, L, Popko, J.L., Zhang, X.-H., Osakabe, K., Tsai, C.J., Joshi, C.P. and Chiang, V.L. (1997) 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.
20. Maury, S., Geoffroy, P. and Legrand, M. (1999) Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns. Plant Physiol. 121, 215-223.
21. Morishige, T., Tsujita, T., Yamada, Y. and Sato, F. (2000) Molecular characterization of the S-adenosyl-L-methionine: 3′-hydroxy-N- methylcoclaurine 4′-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica. J. Biol. Chem. 275, 23398-23405.
22. Pauli, H.H. and Kutchan, T.M. (1998) Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcocolaurine 3′-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450 dependent monooxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J. 13, 793-801.
23. Roberts, M.F., McCarthy, D., Kutchan, T.M. and Coscia, C.J. (1983) Localization of enzymes and alkaloidal metabolites in Papaver latex. Arch. Biochem. Biophys. 222, 599-609.
24. Rosco, A., Pauli, H.H., Priesner, W. and Kutchan, T.M. (1997) Cloning and heterologous expression of cytochrome P450 reductases from the Papaveraceae. Arch. Biochem. Biophys. 348, 369-377.
25. Rüffer, M., Nagakura, N. and Zenk, M.H. (1983a) Partial purification and properties of S-adenosylmethionine:(R,S)-norlaudanosoline 6-O-methyltransferase from Argemone platyceras cell cultures. Planta Med. 49, 131-137.
26. Rüffer, M., Nagakura, N. and Zenk, M.H. (1983b) A highly specific O-methyltransferase for nororientaline synthesis isolated from /Argemone platyceras cell cultures. Planta Med. 49, 196-198.
27. Schröder, G., Wehinger, E. and Schröder, J. (2002) Predicting the substrates of cloned plant O-methyltransferases. Phytochemistry, 59, 1-8.
28. 14C-labeled S-adenosyl-L-methionine in presence of mammalian catechol O-methyltransferase. Helv. Chim. Acta, 73, 426-432.
29. Small, L.F. and Lutz, R.E. ( 1932) Chemistry of the Opium Alkaloids. Supplement No. 103, Public Health Reports of the United States Treasury Department. Washington: Oxford University Press, p. 34.
30. Unterlinner, B., Lenz, R. and Kutchan, T.M. (1999) Molecular cloning and functional expression of codeinone reductase - the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J. 18, 465-475.