Characterization of a multifunctional methyltransferase from the orchid Vanilla planifolia

Plant Cell Reports

Volumn 22, Issue 12, 2004, Pages 959-966

  Pak, F E ^a   Gropper, S ^a   Dai, W D ^a   Havkin Frenkel, D ^a   Belanger, F C ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

3,4 Dihydroxybenzaldehyde; Caffeic acid methyltransferase; Vanillin

Indexed keywords

ALDEHYDES; BIOSYNTHESIS; DNA; ENZYMES; GENETIC ENGINEERING; METHANOL;

RECOMBINANT ENZYMES; TISSUE DISTRIBUTION;

PLANT CELL CULTURE;

VANILLA PLANIFOLIA;

EID: 3242714209     PISSN: 07217714     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00299-004-0795-x     Document Type: Article

References (44)

1. Angiosperm Phylogeny Group (1998) An ordinal classification for the families of flowering plants. Ann Mo Bot Gard 85:531-553
2. Attieh JM, Hanson AD, Saini HS (1995) Characterization of a novel methyltransferase responsible for biosynthesis of halomethanes and methanethiol in Brassica oleracea. J Biol Chem 270:9250-9257
3. Bout S, Vermerris W (2003) A candidate-gene approach to clone the sorghum brown midrib gene encoding caffeic acid O-methltransferase. Mol Genet Genomics 269:205-214
4. Bugos RC, Chiang VL, Campbell WH (1991) cDNA cloning, sequence analysis and seasonal expression of lignin-bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase of aspen. Plant Mol Biol 17:1203-1215
5. Collazo P, Montoliu L, Puigdomenech P, Rigau J (1992) Structure and expression of the lignin O-methyltransferase gene from Zea mays L. Plant Mol Biol 20:857-867
6. Dignum MJW, Kerler J, Verpoorte R (2001) Vanilla production: technological, chemical, and biosynthetic aspects. Food Rev Int 17:199-219
7. Dixon RA, Chen F, Guo D, Parvathi K (2001) The biosynthesis of monolignols: a "metabolic grid", or independent pathways to guaiacyl and syringyl units? Phytochemistry 57:1069-1084
8. Don RH, Cox PT, Wainwright BJ, Baker K, Mattick JS (1991) "Touchdown" PCR to circumvent spurious priming during gene amplification. Nucleic Acids Res 19:4008
9. Frick S, Kutchan TM (1999) Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J 17:329-339
10. Gang DR, Lavid N, Zubieta C, Chen F, Beuerle T, Lewinsohn E, Noel JP, Pichersky E (2002) Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell 14:505-519
11. Garcia-Mas J, Messeguer R, Arus P, Puigdomenech P (1995) The caffeic acid O-methyltransferase from Prunus amygdalus (GenBank X83217). Plant Physiol 108:1341
12. Gowri G, Bugos RC, Campbell WH, Maxwell CA, Dixon RA (1991) Stress responses in alfalfa (Medicago sativa L.) X. Molecular cloning and expression of S-adenosyl-L-methioninexaffeic acid 3-O-methyltransferase, a key enzyme of lignin biosynthesis. Plant Physiol 97:7-14
13. Guo D, Chen F, Inoue K, Blount JW, Dixon RA (2001) Down-regulation of caffeic acid 3-O-methyltransferase and caffeoyl CoA3-O-methyltransferase in transgenic alfalfa: impacts on lignin structure and implications for the biosynthesis of G and S lignin. Plant Cell 13:73-88
14. Havkin-Frenkel D, Podstolski A, Knorr D (1996) Effect of light on vanillin precursors formation by in vitro cultures of Vanilla planifolia. Plant Cell Tissue Organ Cult 46:169-170
15. Havkin-Frenkel D, Podstolski A, Witkowska E, Molecki P, Mlkolajczyk M (1999) Vanillin biosynthetic pathways: an overview. In: Fu TJ, Singh G, Curtis WR (eds) Plant cell and tissue culture for the production of food ingredients. Kluwer/Plenum, Dordrecht/New York, pp 35-43
16. Havkin-Frenkel D, French JC, Graft NM, Joel DM, Pak FE, Frenkel C (2003) Interrelation of curing and botany in vanilla (Vanilla planifolia) bean. Acta Hortic 629:93-102
17. Herz LE (2000) Dynamics and regulatory control of the vanillin biosynthetic pathway in V. planifolia embryo cultures. PhD thesis, Rutgers University, N.J.
18. Ibrahim RK, Bruneau A, Bantignies B (1998) Plant O-methyltransferases: molecular analysis, common signature and classification. Plant Mol Biol 36:1-10
19. Jaeck E, Martz F, Stiefel V, Fritig B, Legrand M (1996) Expression of class I O-methyltransferase in healthy and TMV-infected tobacco. Mol Plant Microbe Interact 9:681-688
20. Jang CS, Kim JY, Haam JW, Lee MS, Kim DS, Li YW, Seo YW (2003) Expressed sequence tags from a wheat-rye translocation line (2BS/2RL) infested by larvae of Hessian fly [Mayetiola destructor (Say)]. Plant Cell Rep 22:150-158
21. Joel DM, French JC, Graft N, Kourteva G, Dixon RA, Havkin-Frenkel D (2003) A hairy tissue produces vanillin. Isr J Plant Sci 51:157-159
22. Knorr D, Caster C, Dorneburg H, Dorn R, Graf S, Havkin-Frenkel D, Podstolski A, Werrman T (1993) Biosynthesis and yield improvement of food ingredients from plant cell and tissue cultures. Food Technol 47:57-63
23. Kuhl JC, Cheung F, Yuan Q, Martin W, Zewdie Y, McCallum J, Catanach A, Rutherford P, Sink KC, Jenderek M, Prince J, Town CD, Havey MJ (2004) A unique set of 11,008 onion expressed sequence tags reveals expressed sequence and genomic differences between the monocot orders Asparagales and Poales. Plant Cell 16:114-125
24. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685
25. Li L, Popko JL, Umezawa T, Chiang VL (2000) 5-Hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation, a new view of monolignol biosynthesis in angiosperms. J Biol Chem 275:6537-6545
26. Maury S, Geoffroy P, Legrand M (1999) Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methltransferse and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns. Plant Physiol 121:215-223
27. McAlister FM, Jenkins CLD, Watson JM (1998) Sequence and expression of a stem-abundant caffeic acid O-methyltransferase cDNA from perennial ryegrass (Lolium perenne). Aust J Plant Physiol 25:225-235
28. Osakabe K, Tsao CC, Li L, Popko JL, Umezawa T, Carraway DT (1999) Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms. Proc Natl Acad Sci USA 96:8955-8960
29. Parvathi K, Chen F, Guo D, Blount JW, Dixon RA (2001) Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols. Plant J 25:193-202
30. Podstolski A, Havkin-Frenkel D, Malinowski J, Blount JW, Kourteva G, Dixon RA (2002) Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry 61:611-620
31. Poeydomenge O, Boudet AM, Grima-Pettenati J (1994) A cDNA encoding S-adenosyl-L-methionine:caffeic acid 3-O-methyltransferase from Eucalyptus. Plant Physiol 105:749-750
32. Rao SR, Ravishankar GA (2000) Vanilla flavour: production by conventional and biotechnological routes. J Sci Food Agric 80:289-304
33. Schroder G, Wehinger E, Schroder J (2002) Predicting the substrates of cloned plant O-methyltransferases. Phytochemistry 59:1-8
34. Schwab W (2003) Metabolome diversity: too few genes, too many metabolites? Phytochemistry 62:837-849
35. Selman-Housein G, Lopez M, Hernandez D, Civardi L, Miranda F, Rigau J, Puigdomenech P (1999) Molecular cloning of cDNAs coding for three sugarcane enzymes involved in lignification. Plant Sci 143:163-171
36. Short U, Fernandez JM, Sorge JA, Huse WD (1988) λZAP: a bacteriophage λ expression vector with in vivo excision properties. Nucleic Acids Res 16:7583-7599
37. Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505-515
38. Wang J, Pichersky E (1997) Nucleotide sequence of S-adenosyl-L- methioninexaffeic acid 3-O-methyltransferase from Clarkia breweri (accession no. AF006009). Plant Physiol 114:1567
39. Wang J, Pichersky E (1998) Characterization of S-adenosyl-L-methionine: (iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri. Arch Biochem Biophys 349:153-160
40. Wang J, Dudareva N, Bhakta S, Raguso RA, Pichersky E (1997) 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
41. Wang J, Dudareva N, Kish CM, Simon JE, Lewinsohn E, Pichersky E (1999) Nucleotide sequences of two cDNAs encoding caffeic acid O-methyltransferases (accession nos. AF154917 and AF154918) from sweet basil (Ocimum basilicum). Plant Physiol 120:1205
42. Wein M, Lavid N, Lunkenbein S, Lewinsohn E, Schwab W, Kaldenhoff R (2002) 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 32:755-765
43. Xue Z-T, Brodelius PE (1998) Kinetin-induced caffeic acid O-methyltransferases in cell suspension cultures of Vanilla planifolia Andr. and isolation of caffeic acid O-methyltransferase cDNAs. Plant Physiol Biochem 36:779-788
44. Zubieta C, Kota P, Ferrer 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 Cell 14:1265-1277