Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography-mass spectrometry analysis

被引:16
作者
de Souza, Lauro M. [1 ,2 ]
Dartora, Nessana [2 ]
Scoparo, Camila T. [2 ]
Gorin, Philip A. J. [2 ]
Iacomini, Marcello [2 ]
Sassaki, Guilherme L. [2 ]
机构
[1] Fac Pequeno Principe, Inst Pesquisa Pere Pequeno Principe, BR-80250200 Curitiba, Parana, Brazil
[2] Univ Fed Parana, Dept Bioquim & Biol Mol, BR-81531980 Curitiba, Parana, Brazil
关键词
Glycoside isomers; UHPLC-MS; Isopropylidene; Multiple-stage mass spectrometry; Maytenus ilicifolia; MAYTENUS-ILICIFOLIA; GLYCOSIDES; IDENTIFICATION; DISSOCIATION; COMPLEXATION; INHIBITION;
D O I
10.1016/j.chroma.2016.03.069
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Flavonol glycosides are important components of leaves from vascular plants. A lot of isomers of these compounds are produced by plants, making their analysis very difficult and causing many structural misinterpretations. Galactosides and glucosides as mono- or oligosaccharides yield many diastereoisomers, hindering the analysis by mass spectrometry. In order to enable the mass spectrometric distinctions of these isomers, in this work we combine an isopropylidene based chemical derivatization with liquid chromatography with multiple-stage mass spectrometry (LC-MSn) analysis. The isomers of flavonol triglycosides, after the reaction, yielded products with different molecular weight, therefore, they were no longer isomers, allowing their identification by MS1 analysis. However, to the 4 isomers of flavonol diglycosides, only one yielded, after isopropylidenation, a product with different molecular weight. To the other 3 species, the incorporation of 2 isopropylidene groups retained them in the isomeric form. For such species, chromatographic separation and MSn detection targeting the lithium adducts of 3,4-O-isopropylidene-galactosyl or 4,6-O-isopropylidene-glucosyl residues (m/z 209.099) provided specific MS profile. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:64 / 71
页数:8
相关论文
共 22 条
  • [1] Flavonoid-rich fraction of Maytenus ilicifolia Mart. ex. Reiss protects the gastric mucosa of rodents through inhibition of both H+,K+-ATPase activity and formation of nitric oxide
    Baggio, Cristiane Hatsuko
    Freitas, Cristina Setim
    Otofuji, Glducia de Martini
    Cipriani, Thales Ricardo
    de Souza, Lauro Mera
    Sassaki, Guilherme Lanzi
    Iacomini, Marcello
    Andrade Marques, Maria Consuelo
    Mesia-Vela, Sonia
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 2007, 113 (03) : 433 - 440
  • [2] Muscarinic-dependent inhibition of gastric emptying and intestinal motility by fractions of Maytenus ilicifolia Mart ex. Reissek
    Baggio, Cristiane Hatsuko
    Freitas, Cristina Setim
    Mayer, Barbara
    dos Santos, Ana Cristina
    Twardowschy, Andre
    Potrich, Francine Bittencourt
    Cipriani, Thales Ricardo
    de Souza, Lauro Mera
    Sassaki, Guilherme Lanzi
    Lacomini, Marcello
    Andrade Marques, Maria Consuelo
    Mesia-Vela, Sonia
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 2009, 123 (03) : 385 - 391
  • [3] Identification of a dicaffeoylquinic acid isomer from Arctium lappa with a potent anti-ulcer activity
    Carlotto, Juliane
    da Silva, Luisa M.
    Dartora, Nessana
    Maria-Ferreira, Daniele
    Sabry, Diego de A.
    Filho, Arquimedes P. S.
    de Paula Werner, Maria F.
    Sassaki, Guilherme L.
    Gorin, Philip A. J.
    Iacomini, Marcello
    Cipriani, Thales R.
    de Souza, Lauro M.
    [J]. TALANTA, 2015, 135 : 50 - 57
  • [4] A potent and nitric oxide-dependent hypotensive effect induced in rats by semi-purified fractions from Maytenus ilicifolia
    Crestani, Sandra
    Rattmann, Yanna D.
    Cipriani, Thales R.
    de Souza, Lauro M.
    Iacomini, Marcello
    Kassuya, Candida A. L.
    Marques, Maria C. A.
    Eduardo da Silva-Santos, J.
    [J]. VASCULAR PHARMACOLOGY, 2009, 51 (01) : 57 - 63
  • [5] Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules
    Cuyckens, F
    Claeys, M
    [J]. JOURNAL OF MASS SPECTROMETRY, 2005, 40 (03): : 364 - 372
  • [6] LC-MSn methods for saccharide characterization of monoglycosyl flavonoids using postcolumn manganese complexation
    Davis, BD
    Brodbelt, JS
    [J]. ANALYTICAL CHEMISTRY, 2005, 77 (06) : 1883 - 1890
  • [7] Analysis of flavonol glycoside isomers from leaves of Maytenus ilicifolia by offline and online high performance liquid chromatography-electrospray mass spectrometry
    de Souza, Lauro M.
    Cipriani, Thales R.
    Serrato, Rodrigo V.
    da Costa, Denise E.
    Iacomini, Marcello
    Gorin, Philip A. J.
    Sassaki, Guilherme L.
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2008, 1207 (1-2) : 101 - 109
  • [8] Comprehensive analysis of mate (Ilex paraguariensis) compounds: Development of chemical strategies for matesaponin analysis by mass spectrometry
    de Souza, Lauro M.
    Dartora, Nessana
    Scoparo, Camila T.
    Cipriani, Thales R.
    Gorin, Philip A. J.
    Iacomini, Marcello
    Sassaki, Guilherme L.
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2011, 1218 (41) : 7307 - 7315
  • [9] Heart-cutting two-dimensional (size exclusion x reversed phase) liquid chromatography-mass spectrometry analysis of flavonol glycosides from leaves of Maytenus ilicifolia
    de Souza, Lauro M.
    Cipriani, Thales R.
    Sant'Ana, Carolina F.
    Iacomini, Marcello
    Gorin, Philip A. J.
    Sassaki, Guilliernie L.
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2009, 1216 (01) : 99 - 105
  • [10] A SYSTEMATIC NOMENCLATURE FOR CARBOHYDRATE FRAGMENTATIONS IN FAB-MS MS SPECTRA OF GLYCOCONJUGATES
    DOMON, B
    COSTELLO, CE
    [J]. GLYCOCONJUGATE JOURNAL, 1988, 5 (04) : 397 - 409