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

Phytochemistry. 2008 Jan;69(1):99-111. doi: 10.1016/j.phytochem.2007.06.017. Epub 2007 Jul 31.

Abstract

Flavonoids detected from a model legume plant, Lotus japonicus accessions Miyakojima MG-20 and Gifu B-129, were profiled using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry (LC-FTICR/MS). Five flavonols and two anthocyanidins were detected as aglycones. LC-FTICR/MS facilitated simultaneous detection of 61 flavonoids including compounds that have not been reported previously. Chemical information of the peaks such as retention time, lambdamax, m/z value of the quasi-molecular ion, m/z value of MS/MS fragment ions, and relative intensity of MS/MS fragments was obtained, along with the molecular formulas and conjugate structures. Fourteen were completely identified by comparison with authentic compounds. The high accuracy of m/z values, being 0.081 ppm between observed and theoretical values, allowed prediction of molecular formulas of unknown compounds with the help of isotope peak information for determination of chemical composition. Based on a predicted elemental composition, the presence of a novel nitrogen-containing flavonoid was proposed. A comparison of flavonoid profiles in flowers, stems, and leaves demonstrated that the flowers yielded the most complex profile, containing 30 flower-specific flavonoids including gossypetin glycosides and isorhamnetin glycosides. A comparison of flavonoid profiles between MG-20 and B-129 grown under the same conditions revealed that the accumulation of anthocyanins was higher in B-129 than MG-20, particularly in the stem. Developmental changes in the flavonoid profiles demonstrated that kaempferol glycosides increased promptly after germination. In contrast, quercetin glycosides, predominant flavonoids in the seeds, were not detectable in growing leaves.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyclotrons*
  • Flavonoids / analysis*
  • Flavonoids / chemistry
  • Flavonoids / metabolism*
  • Flavonols / chemistry
  • Fourier Analysis*
  • Glycosides / analysis
  • Lotus / chemistry*
  • Lotus / growth & development
  • Lotus / metabolism*
  • Mass Spectrometry / methods*
  • Nitrogen / chemistry
  • Plant Components, Aerial / chemistry
  • Plant Components, Aerial / growth & development
  • Quercetin / analogs & derivatives
  • Spectrophotometry, Ultraviolet

Substances

  • Flavonoids
  • Flavonols
  • Glycosides
  • 3-methylquercetin
  • Quercetin
  • Nitrogen
  • gossypetin