Profiling of phenylpropanoids in transgenic low-sinapine oilseed rape (Brassica napus)

Phytochemistry

Volumn 71, Issue 10, 2010, Pages 1076-1084

  Wolfram, Karina ^a   Schmidt, Jürgen ^a   Wray, Victor ^b   Milkowski, Carsten ^a   Schliemann, Willibald ^a   Strack, Dieter ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

Brassica napus; Brassicaceae; Gene suppression; Glucosyltransferase; Phenylpropanoids; Sinapate esters; Structure elucidation

Indexed keywords

PHENYLPROPIONIC ACID DERIVATIVE;

ARTICLE; BRASSICA; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT SEED; PRENATAL DEVELOPMENT; TRANSGENIC PLANT; EMBRYOLOGY;

BRASSICA; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PHENYLPROPIONATES; PLANTS, GENETICALLY MODIFIED; SEEDS;

BRASSICA NAPUS; BRASSICACEAE;

EID: 77952546832     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.04.007     Document Type: Article

References (38)

1. F. Abe, Y. Iwase, T. Yamauchi, S. Yahara, and T. Nohara Flavonol sinapoyl glycosides from leaves of Thevetia peruviana Phytochemistry 40 1995 577 581
2. A. Baumert, C. Milkowski, J. Schmidt, M. Nimtz, V. Wray, and D. Strack Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family? Phytochemistry 66 2005 1334 1345
3. J.M. Bell Factors affecting the nutritional value of canola meal: a review Can. J. Anim. Sci. 73 1993 679 697
4. C. Böttcher, E. von Roepenack-Lahaye, J. Schmidt, S. Clemens, and D. Scheel Analysis of phenolic choline esters from seeds of Arabidopsis thaliana and Brassica napus by capillary liquid chromatography/electrospray - tandem mass spectrometry J. Mass Spectrom. 44 2009 466 476
5. C. Böttcher, E. von Roepenack-Lahaye, J. Schmidt, C. Schmotz, S. Neumann, D. Scheel, and S. Clemens Metabolome analysis of biosynthetic mutants reveals a diversity of metabolic changes and allows identification of a large number of new compounds in Arabidopsis Plant Physiol. 147 2008 2107 2120
6. S. Clausen, O. Olsen, and H. Sörensen Separation of aromatic choline esters by high-performance liquid chromatography J. Chromatogr. 260 1983 193 199
7. R. Dauwe, K. Morreel, G. Goeminne, B. Gielen, A. Rohde, J. Van Beeumen, J. Ralph, A.-M. Boudet, J. Kopka, S.F. Rochange, C. Halpin, E. Messens, and W. Boerjan Molecular phenotyping of lignin-modified tobacco reveals associated changes in cell-wall metabolism, primary metabolism, stress metabolism and photorespiration Plant J. 52 2007 263 285
8. FAO/WHO, 2000. Safety Aspects of Genetically Modified Foods of Plant Origin. WHO Geneva.
9. G.R. Fenwick The assessment of a new protein source - rapeseed Proc. Nutr. Soc. 41 1982 277 288
10. A. Hüsken, A. Baumert, D. Strack, H.C. Becker, C. Möllers, and C. Milkowski Reduction of sinapate ester content in transgenic oilseed rape (Brassica napus) by dsRNAi-based suppression of BnSGT1 gene expression Mol. Breed. 16 2005 127 138
11. T. Ishikawa, Y. Sega, and J. Kitajima Water-soluble constituents of ajowan Chem. Pharm. Bull. 49 2001 840 844
12. Kozlowska, H., Naczk, M., Shahidi, F., Zadernowski, R., 1990. Phenolic acids and tannins in rapeseed and canola. In: Shadidi, F. (Ed.) Canola and Rapeseed. Production, Chemistry, Nutrition and Processing Technology. Van Nostrand Reinhold, New York, pp. 193-210.
13. M. Kritsanida, P. Magiatis, A.L. Skaltsounis, and J.P. Stables Phytochemical investigation and anticonvulsant activity of Paeonia parnassica radix Nat. Prod. Commun. 2 2007 351 356
14. L.G. Landry, C.C. Chapple, and R.L. Last Arabidopsis mutants lacking phenolic sunscreens exhibit enhanced ultraviolet-B injury and oxidative damage Plant Physiol. 109 1995 1159 1166
15. B.J. Li, B.C. Gao, S.L. Peng, X. Liao, and L.S. Ding Chemical constituents of Acanthochlamys bracteata Chin. J. Chem. 23 2005 933 936
16. A. Martinez-Sanchez, A. Gil-Izquierdo, M.I. Gil, and F. Ferreres A comparative study of flavonoid compounds, vitamin C, and antioxidant properties of baby leaf Brassicaceae species J. Agric. Food Chem. 56 2008 2330 2340
17. A. Martinez-Sanchez, R. Llorach, M.I. Gil, and F. Ferreres Identification of new flavonoid glycosides and flavonoid profiles to characterize rocket leafy salads (Eruca vesicaria and Diplotaxis tenuifolia) J. Agric. Food Chem. 55 2007 1356 1363
18. N. Matsui, F. Chen, S. Yasuda, and K. Fukushima Conversion of guaiacyl to syringyl moieties on the cinnamyl alcohol pathway during the biosynthesis of lignin in angiosperms Planta 210 2000 831 835
19. D. Meißner, A. Albert, C. Böttcher, D. Strack, and C. Milkowski The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana Planta 228 2008 663 674
20. H. Meyermans, K. Morreel, C. Lapierre, B. Pollet, A. De Bruyn, R. Busson, P. Herdewijn, B. Devreese, J. Van Beeumen, J.M. Marita, J. Ralph, C. Chen, B. Burggraeve, M. Van Montagu, E. Messens, and W. Boerjan Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzym A O-methyltransferase, an enzyme involved in lignin biosynthesis J. Biol. Chem. 275 2000 36899 36909
21. Y. Mikanagi, M. Yokoi, Y. Ueda, and N. Saito Flower flavonol and anthocyanin distribution in subgenus Rosa Biochem. Syst. Ecol. 23 1995 183 200
22. C. Milkowski, A. Baumert, D. Schmidt, L. Nehlin, and D. Strack Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation Plant J. 38 2004 80 92
23. C. Milkowski, A. Baumert, and D. Strack Cloning and heterologous expression of a rape cDNA encoding UDP-glucose:sinapate glucosyltransferase Planta 211 2000 883 886
24. J. Mittasch, D. Strack, and C. Milkowski Secondary product glycosyltransferases in seeds of Brassica napus Planta 225 2007 515 522
25. M. Naczk, R. Amarowicz, A. Sullivan, and F. Shahidi Current research developments on polyphenolics of rapeseed/canola: a review Food Chem. 62 1998 489 502
26. Ohlson, R., 1978. Functional properties of rapeseed oil and protein product. In: Proceedings of Fifth International Rapeseed Congress, Malmö, pp. 152-167.
27. K. Orlovius Fertilizing for high yield and quality oilseed rape E.A. Kirby, IPI-Bulletin No. 16 2003 International Potash Institute Basel 1 130
28. J. Rabaté, and J. Dussy Etude biochimique des fruits de Sophora japonica L. II.-Sur le présence de rutinoside et de sophoraflavonoloside dans des fruits verts de Sophora japonica Bull. Soc. Chim. Biol. 20 1938 459 466
29. S. Rangaswami, and T.R. Seshadri Crystalline chemical components of the flowers of Adhatoda vascia Curr. Sci. 40 1971 84 85
30. F. Sanchez-Rabaneda, O. Jauregui, R.M. Lamuela-Raventos, F. Viladomat, J. Bastida, and C. Codina Qualitative analysis of phenolic compounds in apple pomace using liquid chromatography coupled to mass spectrometry in tandem mode Rapid Commun. Mass Sp. 18 2004 553 563
31. F.S. Santamour, and L.G.H. Riedel A new name for Sophora japonica J. Arboricult. (USA) 23 1997 166 167
32. W. Schliemann, B. Schneider, V. Wray, J. Schmidt, M. Nimtz, A. Porzel, and H. Böhm Flavonols and an indole alkaloid skeleton bearing identical acylated glycosidic groups from yellow petals of Papaver nudicaule Phytochemistry 67 2006 191 201
33. F. Shahidi Natural Antioxidants from Oilseeds 1995 International Conference on Food Factors: Chemistry and Cancer Prevention Hamamatsu pp. 299-303
34. F. Shahidi, and M. Naczk An overview of the phenolics of canola and rapeseed: chemical, sensory and nutritional significance J. Am. Oil Chem. Soc. 69 1992 917 924
35. J.J. Sheahan Sinapate esters provide greater UV-B attenuation than flavonoids in Arabidopsis thaliana (Brassicaceae) Am. J. Bot. 83 1996 679 686
36. D. Strack Sinapine as a supply of choline for the biosynthesis of phosphatidylcholine in Raphanus sativus seedlings Z. Naturforsch. 36c 1981 215 221
37. V. Vrchovska, C. Sousa, P. Valentao, F. Ferreres, J.A. Pereira, R.M. Seabra, and P.B. Andrade Antioxidative properties of tronchuda cabbage (Brassica oleracea L. Var. costata DC) external leaves against DPPH, superoxide radical, hydroxyl radical and hypochlorous acid Food Chem. 98 2006 416 425
38. Zhou, Y., Zhou, Z., Cao, P., Tan, X., Ding, L., 2003. Chemical constituents of Idesia polycarpa var. vestita Diels. Tianran Chanwu Yanjiu Yu Kaifa 15(13-14), 17.