Metabolic profiling of flavonoids in Lotus japonicus using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry

Phytochemistry

Volumn 69, Issue 1, 2008, Pages 99-111

  Suzuki, Hideyuki ^a   Sasaki, Ryosuke ^a   Ogata, Yoshiyuki ^a   Nakamura, Yukiko ^b,d   Sakurai, Nozomu ^a   Kitajima, Mariko ^c   Takayama, Hiromitsu ^c   Kanaya, Shigehiko ^b   Aoki, Koh ^a   Shibata, Daisuke ^a   Saito, Kazuki ^c  

^a KAZUSA DNA RESEARCH INSTITUTE   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c CHIBA UNIVERSITY   (Japan)

^d Ehime Women's College   (Japan)

Author keywords

Flavonoids; FT MS; LC FTICR MS; Leguminoseae; Lotus japonicus; Metabolite profiling

Indexed keywords

3-METHYLQUERCETIN; FLAVONOID; FLAVONOL DERIVATIVE; GLYCOSIDE; GOSSYPETIN; NITROGEN; QUERCETIN 3 METHYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CYCLOTRON; FOURIER ANALYSIS; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LOTUS; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; PLANT; ULTRAVIOLET SPECTROPHOTOMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOTRONS; FLAVONOIDS; FLAVONOLS; FOURIER ANALYSIS; GLYCOSIDES; LOTUS; MASS SPECTROMETRY; NITROGEN; PLANT COMPONENTS, AERIAL; SPECTROPHOTOMETRY, ULTRAVIOLET;

LOTUS CORNICULATUS VAR. JAPONICUS;

EID: 37249035287     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.06.017     Document Type: Article

References (35)

1. Aharoni A., Ric de Vos C.H., Verhoeven H.A., Maliepaard C.A., Kruppa G., Bino R., and Goodenowe D.B. Nontargeted metabolome analysis by use of Fourier Transform Ion Cyclotron Mass Spectrometry. Omics 6 (2002) 217-234
2. Asamizu E., Kato T., Sato S., Nakamura Y., Kaneko T., and Tabata S. Structural analysis of a Lotus japonicus genome. IV. Sequence features and mapping of seventy-three TAC clones which cover the 7.5 mb regions of the genome. DNA Res. 10 (2003) 115-122
3. Asamizu E., Nakamura Y., Sato S., and Tabata S. Characteristics of the Lotus japonicus gene repertoire deduced from large-scale expressed sequence tag (EST) analysis. Plant Mol. Biol. 54 (2004) 405-414
4. Endo M., Matsubara H., Kokubun T., Masuko H., Takahata Y., Tsuchiya T., Fukuda H., Demura T., and Watanabe M. The advantages of cDNA microarray as an effective tool for identification of reproductive organ-specific genes in a model legume, Lotus japonicus. FEBS Lett. 514 (2002) 229-237
5. Farag M.A., Huhman D.V., Lei Z., and Sumner L.W. Metabolic profiling and systematic identification of flavonoids and isoflavonoids in roots and cell suspension cultures of Medicago truncatula using HPLC-UV-ESI-MS and GC-MS. Phytochemistry 68 (2007) 342-354
6. Graham T.L. Flavonoid and isoflavonoid distribution in developing soybean seedling tissues and in seed and root exudates. Plant Physiol. 95 (1991) 594-603
7. Hall R.D. Plant metabolomics: from holistic hope, to hype, to hot topic. New Phytol. 169 (2006) 453-468
8. Harborne J.B. Gossypetin and herbacetin as taxonomic markers in higher plants. Phytochemistry 8 (1969) 177-183
9. Hirai M.Y., Klein M., Fujikawa Y., Yano M., Goodenowe D.B., Yamazaki Y., Kanaya S., Nakamura Y., Kitayama M., Suzuki H., Sakurai N., Shibata D., Tokuhisa J., Reichelt M., Gershenzon J., Papenbrock J., and Saito K. Elucidation of gene-to-gene and metabolite-to-gene networks in arabidopsis by integration of metabolomics and transcriptomics. J. Biol. Chem. 280 (2005) 25590-25595
10. Hirai M.Y., Yano M., Goodenowe D.B., Kanaya S., Kimura T., Awazuhara M., Arita M., Fujiwara T., and Saito K. Integration of transcriptomics and metabolomics for understanding of global responses to nutritional stresses in Arabidopsis thaliana. Proc. Natl. Acad. Sci. USA 101 (2004) 10205-10210
11. Huhman D.V., and Sumner L.W. Metabolic profiling of saponins in Medicago sativa and Medicago truncatula using HPLC coupled to an electrospray ion-trap mass spectrometer. Phytochemistry 59 (2002) 347-360
12. Jay M., Hasan A., Voirin B., and Viricel M.R. Les flavonoides du Lotus corniculatus. Phytochemistry 17 (1978) 827-829
13. Kaneko T., Asamizu E., Kato T., Sato S., Nakamura Y., and Tabata S. Structural analysis of a Lotus japonicus genome. III. Sequence features and mapping of sixty-two TAC clones which cover the 6.7 Mb regions of the genome. DNA Res. 10 (2003) 27-33
14. Kato T., Sato S., Nakamura Y., Kaneko T., Asamizu E., and Tabata S. Structural analysis of a Lotus japonicus genome. V. Sequence features and mapping of sixty-four TAC clones which cover the 6.4 mb regions of the genome. DNA Res. 10 (2003) 277-285
15. Kawaguchi M., Motomura T., Imaizumi-Anraku H., Akao S., and Kawasaki S. Providing the basis for genomics in Lotus japonicus: the accessions Miyakojima and Gifu are appropriate crossing partners for genetic analyses. Mol. Genet. Genomics 266 (2001) 157-166
16. Kind T., and Fiehn O. Metabolomic database annotations via query of elemental compositions: mass accuracy is insufficient even at less than 1 ppm. BMC Bioinformatics 7 (2006) 234
17. Kouchi H., Shimomura K., Hata S., Hirota A., Wu G.J., Kumagai H., Tajima S., Suganuma N., Suzuki A., Aoki T., Hayashi M., Yokoyama T., Ohyama T., Asamizu E., Kuwata C., Shibata D., and Tabata S. Large-scale analysis of gene expression profiles during early stages of root nodule formation in a model legume, Lotus japonicus. DNA Res. 11 (2004) 263-274
18. Lazar G., and Goodman H.M. MAX1, a regulator of the flavonoid pathway, controls vegetative axillary bud outgrowth in Arabidopsis. Proc. Natl. Acad. Sci. USA 103 (2006) 472-476
19. Martens S., and Mithofer A. Flavones and flavone synthases. Phytochemistry 66 (2005) 2399-2407
20. Masuko H., Endo M., Saito H., Hakozaki H., Park J.I., Kawagishi-Kobayashi M., Takada Y., Okabe T., Kamada M., Takahashi H., Higashitani A., and Watanabe M. Anther-specific genes, which expressed through microsporogenesis, are temporally and spatially regulated in model legume, Lotus japonicus. Genes Genet. Syst. 81 (2006) 57-62
21. Murch S.J., Rupasinghe H.P., Goodenowe D., and Saxena P.K. A metabolomic analysis of medicinal diversity in Huang-qin (Scutellaria baicalensis Georgi) genotypes: discovery of novel compounds. Plant Cell Rep. 23 (2004) 419-425
22. Nakamura Y., Kaneko T., Asamizu E., Kato T., Sato S., and Tabata S. Structural analysis of a Lotus japonicus genome. II. Sequence features and mapping of sixty-five TAC clones which cover the 6.5-mb regions of the genome. DNA Res. 9 (2002) 63-70
23. Nesi N., Debeaujon I., Jond C., Stewart A.J., Jenkins G.I., Caboche M., and Lepiniec L. The TRANSPARENT TESTA16 locus encodes the ARABIDOPSIS BSISTER MADS domain protein and is required for proper development and pigmentation of the seed coat. Plant Cell 14 (2002) 2463-2479
24. Oikawa A., Nakamura Y., Ogura T., Kimura A., Suzuki H., Sakurai N., Shinbo Y., Shibata D., Kanaya S., and Ohta D. Clarification of pathway-specific inhibition by fourier transform ion cyclotron resonance/mass spectrometry-based metabolic phenotyping studies. Plant Physiol. 142 (2006) 398-413
25. Pfenninger A., Karas M., Finke B., and Stahl B. Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nano-electrospray MS(n) (part 2: application to isomeric mixtures). J. Am. Soc. Mass Spectrom. 13 (2002) 1341-1348
26. Pourcel L., Routaboul J.M., Kerhoas L., Caboche M., Lepiniec L., and Debeaujon I. TRANSPARENT TESTA10 encodes a laccase-like enzyme involved in oxidative polymerization of flavonoids in Arabidopsis seed coat. Plant Cell 17 (2005) 2966-2980
27. Reynaud J., and Lussignol M. The flavonoids of Lotus corniculatus. Lotus Newsletter 35 (2005) 75-82
28. Sato S., Kaneko T., Nakamura Y., Asamizu E., Kato T., and Tabata S. Structural analysis of a Lotus japonicus genome. I. Sequence features and mapping of fifty-six TAC clones which cover the 5.4 mb regions of the genome. DNA Res. 8 (2001) 311-318
29. Seshadri T.R., and Thakur R.S. Constitution of gossytrin, a new glycoside from the flower petals of Hibiscus sabdariffa. J. Indian Chem. Soc. 38 (1961) 649-651
30. Shimada N., Aoki T., Sato S., Nakamura Y., Tabata S., and Ayabe S. A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus. Plant Physiol. 131 (2003) 941-951
31. Shimada N., Sasaki R., Sato S., Kaneko T., Tabata S., Aoki T., and Ayabe S. A comprehensive analysis of six dihydroflavonol 4-reductases encoded by a gene cluster of the Lotus japonicus genome. J. Exp. Bot. 56 (2005) 2573-2585
32. Springob K., Nakajima J., Yamazaki M., and Saito K. Recent advances in the biosynthesis and accumulation of anthocyanins. Nat. Prod. Rep. 20 (2003) 288-303
33. Tohge T., Nishiyama Y., Hirai M.Y., Yano M., Nakajima J., Awazuhara M., Inoue E., Takahashi H., Goodenowe D.B., Kitayama M., Noji M., Yamazaki M., and Saito K. Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor. Plant J. 42 (2005) 218-235
34. Yergey J.A. A general approach to calculating isotopic distributions for mass spectrometry. Int. J. Mass Spectrom. Ion Phys. 52 (1983) 337-349
35. Zaia J., Li X.Q., Chan S.Y., and Costello C.E. Tandem mass spectrometric strategies for determination of sulfation positions and uronic acid epimerization in chondroitin sulfate oligosaccharides. J. Am. Soc. Mass Spectrom. 14 (2003) 1270-1281