Analysis of flavonol glycoside isomers from leaves of Maytenus ilicifolia by offline and online high performance liquid chromatography-electrospray mass spectrometry

被引:40
作者
de Souza, Lauro M. [1 ]
Cipriani, Thales R. [1 ]
Serrato, Rodrigo V. [1 ]
da Costa, Denise E. [1 ]
Iacomini, Marcello [1 ]
Gorin, Philip A. J. [1 ]
Sassaki, Guilherme L. [1 ]
机构
[1] Univ Fed Parana, Dept Bioquim & Biol Mol, BR-81531980 Curitiba, Parana, Brazil
关键词
Liquid chromatography-mass spectrometry; Maytenus ilicifolia; Flavonol glycosides isomers; Kaempferol; Quercetin; Radical aglycone;
D O I
10.1016/j.chroma.2008.08.032
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Flavonol glycosides present in leaves of Maytenus ilicifolia, were examined after fractionation on silica-gel column. Flavonol mono-, di-, tri-, and tetraglycosides, containing kaempferol, quercetin or myricetin were identified by offline electrospray mass spectrometry. Increasing the cone energy induced to adducts variation, from H+ to Na+. Protonated ions were characteristically fragmented by sequentially removing the monosaccharide residues, whereas in the sodiated ions, the aglycone was firstly removed. Online high performance liquid chromatography-mass spectrometry, with simple gradients of water, acetonitrile and acetic acid indicated the presence of several isomers, which were further identified by gas chromatography-mass spectrometry as containing galactose or glucose. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:101 / 109
页数:9
相关论文
共 40 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 [J].
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 .
JOURNAL OF ETHNOPHARMACOLOGY, 2007, 113 (03) :433-440
[2]   A polysaccharide from a tea (infusion) of Maytenus ilicifolia leaves with anti-ulcer protective effects [J].
Cipriani, Thales R. ;
Mellinger, Caroline G. ;
de Souza, Lauro M. ;
Baggio, Cristiane H. ;
Freitas, Cristina S. ;
Marques, Maria C. A. ;
Gorin, Philip A. J. ;
Sassaki, Guilherme L. ;
Iacomini, Marcello .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (07) :1018-1021
[3]   A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES [J].
CIUCANU, I ;
KEREK, F .
CARBOHYDRATE RESEARCH, 1984, 131 (02) :209-217
[4]   Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of electrospray-generated deprotonated and sodiated molecules [J].
Cuyckens, F ;
Claeys, M .
JOURNAL OF MASS SPECTROMETRY, 2005, 40 (03) :364-372
[5]  
Cuyckens F, 2004, J MASS SPECTROM, V39, P1, DOI [10.1002/jms.585, 10.1002/jms.622]
[6]   Direct stereochemical assignment of hexose and pentose residues in flavonoid O-glycosides by fast atom bombardment and electrospray ionization mass spectrometry [J].
Cuyckens, F ;
Shahat, AA ;
Pieters, L ;
Claeys, M .
JOURNAL OF MASS SPECTROMETRY, 2002, 37 (12) :1272-1279
[7]   Optimization of a liquid chromatography method based on simultaneous electrospray ionization mass spectrometric and ultraviolet photodiode array detection for analysis of flavonoid glycosides [J].
Cuyckens, F ;
Claeys, M .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2002, 16 (24) :2341-2348
[8]   Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry [J].
Cuyckens, F ;
Rozenberg, R ;
de Hoffmann, E ;
Claeys, M .
JOURNAL OF MASS SPECTROMETRY, 2001, 36 (11) :1203-1210
[9]   HPLC/ESI-MS and NMR analysis of flavonoids and tannins in bioactive extract from leaves of Maytenus ilicifolia [J].
de Souza, Lauro M. ;
Cipriani, Thales R. ;
Iacomini, Marcello ;
Gorin, Philip A. J. ;
Sassaki, Guilherme L. .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2008, 47 (01) :59-67
[10]   FAB-MASS SPECTROMETRY OF CARBOHYDRATES [J].
DELL, A .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1987, 45 :19-72