Scent evolution in Chinese roses

Proceedings of the National Academy of Sciences of the United States of America

Volumn 105, Issue 15, 2008, Pages 5927-5932

  Scalliet, Gabriel ^a,e   Piola, Florence ^b   Douady, Christophe J ^b   Rety, Stéphane ^c   Raymond, Olivier ^a   Baudino, Sylvie ^d   Bordji, Karim ^a,c   Bendahmane, Mohammed ^a   Dumas, Christian ^a   Cock, J Mark ^a,f   Hugueney, Philippe ^a,g  

^a UNIVERSITÉ DE LYON   (France)

^b UNIVERSITÉ LYON 1   (France)

^c CNRS   (France)

^d UNIVERSITÉ JEAN MONNET   (France)

^e SYNGENTA CROP PROTECTION AG   (Switzerland)

^f STATION BIOLOGIQUE DE ROSCOFF   (France)

^g UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Dimethoxytoluene; Flower; Hybrid tea; Volatiles

Indexed keywords

ELEMICIN;

ARTICLE; BINDING SITE; BIOSYNTHESIS; CHEMICAL STRUCTURE; GENETIC POLYMORPHISM; METHYLATION; MULTIGENE FAMILY; ODOR; PRIORITY JOURNAL; ROSE;

ROSA; ROSA ARKANSANA; ROSA CHINENSIS; ROSA ODORATA;

EID: 44449132589     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0711551105     Document Type: Article

References (43)

1. Krüssmann G (1982) in Roses (B. T. Batsford, London), English ed.
2. Flament I, Debonneville C, Furrer A (1993) Volatile constituents of roses: Characterization of cultivars based on the headspace analysis of living flower emissions. Bioactive Volatile Compounds from Plants, eds Teranishi R, Buttery RG, Sugisawa H (Am Chem Soc, Washington, DC), pp 269-281.
3. Joichi A, Yomogida K, Awano K, Ueda Y (2005) Volatile components of tea-scented modern roses and ancient Chinese roses. Flavour Fragr J 20:152-157.
4. Nakamura S (1987) Scent and component analysis of the hybrid tea rose. Perfum Flavor 12:43-45.
5. Guterman I, et al. (2002) Rose scent: Genomics approach to discovering novel floral fragrance-related genes. Plant Cell 14:2325-2338.
6. Channelière S, et al. (2002) Analysis of gene expression in rose petals using expressed sequence tags. FEBS Lett 515:35-38.
7. Shalit M, et al. (2003) Volatile ester formation in roses: Identification of an acetylcoenzyme A-Geraniol/Citronellol acetyltransferase in developing rose petals. Plant Physiol 131:1868-1876.
8. Kaminaga Y, et al. (2006) Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation. J Biol Chem 281:23357-23366.
9. Lavid N, et al. (2002) O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Plant Physiol 129:1899-1907.
10. Scalliet G, et al. (2002) Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases. FEBS Lett 523:113-118.
11. Scalliet G, et al. (2006) Role of petal-specific orcinol O-methyltransferases in the evolution of rose scent. Plant Physiol 140:18-29.
12. Zubieta C, He XZ, Dixon RA, Noel JP (2001) Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases. Nat Struct Biol 8:271-279.
13. Zubieta C, Kota P, Ferrer JL, 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.
14. Zubieta C, et al. (2003) Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family. Plant Cell 15:1704-1716.
15. Ferrer JL, Zubieta C, Dixon RA, Noel JP (2005) Crystal structures of alfalfa caffeoyl coenzyme A 3-O-methyltransferase. Plant Physiol 137:1009-1017.
16. Gang DR, et al. (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.
17. Pott MB, et al. (2004) Biochemical and structural characterization of benzenoid carboxyl methyltransferases involved in floral scent production in Stephanotis floribunda and Nicotiana suaveolens. Plant Physiol 135:1946-1955.
18. Pichersky E, Gang DR (2000) Genetics and biochemistry of secondary metabolites in plants: An evolutionary perspective. Trends Plant Sci 5:439-445.
19. Zhang J (2003) Evolution by gene duplication: An update. Trends Ecol Evol 18:292-298.
20. Dudareva N, Cseke L, Blanc VM, Pichersky E (1996) Evolution of floral scent in Clarkia: Novel patterns of S-linalool synthase gene expression in the C. breweri flower. Plant Cell 8:1137-1148.
21. Noel JD, Dixon RA, Pichersky E, Zubieta C, Ferrer J (2003) Structural, functional and evolutionary basis for methylation of plant small molecules. Recent Advances in Phytochemistry, ed Romeo JT (Elsevier Science Ltd, Oxford), Vol 37, pp 253-283.
22. Wang J, Pichersky E (1999) Identification of specific residues involved in substrate discrimination in two plant O-methyltransferases. Arch Biochem Biophys 368:172-180.
23. Kapteyn J, et al. (2007) Evolution of cinnamate/p-coumarate carboxyl methyltransferases and their role in the biosynthesis of methylcinnamate. Plant Cell 19:3212-3229.
24. Barkman TJ (2003) Evidence for positive selection on the floral scent gene isoeugenol O-methyltransferase. Mol Biol Evol 20:168-172.
25. Barkman TJ, Martins TR, Sutton E, Stout JT (2007) Positive selection for single amino acid change promotes substrate discrimination of a plant volatile-producing enzyme. Mol Biol Evol 24:1320-1329.
26. Wissemann V, Ritz CM (2005) The genus Rosa (Rosoideae, Rosaceae) revisited: Molecular analysis of nrITS-1 and atpB-rbcL intergenic spacer (IGS) versus conventional taxonomy. Bot J Linn Soc 147:275-290.
27. Schröder G, Wehinger E, Schröder J (2002) Predicting the substrates of cloned plant O-methyltransferases. Phytochemistry 59:1-8.
28. Shalit M, et al. (2004) Volatile compounds emitted by rose cultivars: Fragrance perception by man and honeybees. Isr J Plant Sci 52:245-255.
29. Wright GA, Lutmerding A, Dudareva N, Smith BH (2005) Intensity and the ratios of compounds in the scent of snapdragon flowers affect scent discrimination by honeybees (Apis mellifera). J Comp Physiol A 191:105-114.
30. Rix M (1999) China roses. Historic Roses Journal No. 17, ed Foster R (Royal National Rose Society, St. Albans, Hertfordshire, England), pp 8-12.
31. Wu S, et al. (2004) The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1,3,5-trimethoxybenzene. Plant Physiol 135:1-8.
32. Gang DR (2005) Evolution of flavors and scents. Annu Rev Plant Biol 56:301-325.
33. Wu S, et al. (2003) Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis. J Biosci Bioeng 96:119-128.
34. Yokoyama S (2002) Evaluating adaptive evolution. Nat Genet 30:350-351.
35. Sali A, Blundell TL (1993) Comparative protein modelling by satisfaction of spatial restraints. J Mol Biol 234:779-815.
36. Kleywegt GJ, Jones TA (1998) Databases in protein crystallography. Acta Crystallogr D 54:1119-1131.
37. Sippl MJ (1993) Recognition of errors in three-dimensional structures of proteins. Proteins 17:355-362.
38. Morris GM, et al. (1998) Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J Comput Chem 19:1639-1662.
39. Thompson JD, Higgins DG, Gibson TJ (1994) CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680.
40. Huelsenbeck JP, Ronquist F (2001) MRBAYES: Bayesian inference of phylogenetic trees. Bioinformatics 17:754-755.
41. Swofford DL (2002) PAUP*: Phylogenetic Analysis Using Parsimony (*and Other Methods) (Sinauer Associates, Sunderland, MA), Version 4.
42. Akaike H (1974) A new look at the statistical model identification. IEEE Trans Autom Contr 19:716-723.
43. Posada D, Crandall KA (1998) MODELTEST: Testing the model of DNA substitution. Bioinformatics 14:817-818.