Mass spectrometry in the structural analysis of flavonoids

Journal of Mass Spectrometry

Volumn 39, Issue 1, 2004, Pages 1-15

  Cuyckens, Filip ^a   Claeys, Magda ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Collision induced dissociation; Electrospray ionization; Flavonoid glycosides; Liquid chromatography; Mass spectrometry; Tandem mass spectrometry

Indexed keywords

BIOMARKERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANTS (BOTANY);

FLAVONOIDS;

METABOLITES;

BIOLOGICAL MARKER; FLAVONOID; FUNCTIONAL GROUP; GLYCOSIDE;

ACYLATION; ANALYTIC METHOD; CHEMICAL STRUCTURE; CHEMOTAXONOMY; CONTROLLED STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; PLANT; PRIORITY JOURNAL; QUALITY CONTROL; RELIABILITY; REVIEW; SAMPLING; SENSITIVITY AND SPECIFICITY; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

FLAVONOIDS; GLYCOSIDES; MASS SPECTROMETRY; PLANTS;

EID: 1142303819     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.585     Document Type: Review

References (128)

1. Smith H. In Phytochrome, Mitrakos K, Shropshire W (eds), Academic Press: London 1972; 433.
2. Iwashina T. The structure and distribution of the flavonoids in plants. J. Plant Res. 2000; 113: 287.
3. Di Carlo G, Mascolo N, Izzo AA, Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999; 65:337.
4. Nijveldt RJ, van Nood E, van Hoorn DEC, Boelens PG, van Norren K, van Leeuwen PAM. Flavonoids: a review of probable mechanisms of actions and potential applications. Am. J. Clin. Nutr. 2001; 74: 418.
5. Pietta PG. Flavonoids as antioxidants. J. Nat. Prod. 2000; 63: 1035.
6. Cos P, Calomme M, Sindambiwe JB, De Bruyne T, Cimanga K, Pieters L, Vlietinck AJ, Vanden Berghe D. Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids. Planta Med. 2001;67:515.
7. van Acker SABE, Tromp MNJL, Haenen GRMM, van der Vijgh WJF, Bast A. Flavonoids as scavengers of nitric oxide radical. Biochem. Biophys. Res. Commun. 1995; 214: 755.
8. Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Vanden Berghe D. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J. Nat. Prod. 1998; 61: 71.
9. Ferrali M, Signorini C, Caciotti B, Sugherini L, Ciccoli L, Giachetti D, Comporti M. Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity. FEBS Lett. 1997; 416: 123.
10. Le Marchand L. Cancer preventive effects of flavonoids. Biomed. Pharmacother. 2002; 56: 296.
11. Commenges D, Scotet V, Renaud S, Jacqmin-Gadda H, Barberger-Gateau P, Dartigues JF. Intake of flavonoids and risk of dementia. Eur. J. Epidemiol. 2000; 16: 357.
12. Aviram M, Fuhrman B. Wine flavonoids protect against LDL oxidation and atherosclerosis. Ann. NY Acad. Sci. 2002; 957:146.
13. Hertog MGL, Feskens EJM, Hollman PCH, Katan MB, Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart-disease - The Zutphen elderly study. Lancet 1993;342:1007.
14. Mojzisova G, Kuchta M. Dietary flavonoids and risk of coronary heart disease. Physiol. Res. 2001; 50: 529.
15. Kim HP, Mani I, Iversen L, Ziboh VA. Effects of naturally occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase from guinea-pigs. Prostag. Leukotr. Ess. 1998; 58: 17.
16. You KM, Jong HG, Kim HP. Inhibition of cyclooxygenase/lipoxygenase from human platetelets by polyhydroxylated/methoxylated flavonoids isolated from medicinal plants. Arch. Pharm. Res. 1999; 22: 18.
17. Pelzer LE, Guardia T, Juarez AO, Guerreiro E. Acute and chronic antiinflammatory effects of plant flavonoids. Farmaco 1998; 53:421.
18. Hollman PCH, Katan MB. Absorption, metabolism and health effects of dietary flavonoids in man. Biomed. Pharmacother. 1997; 51: 305.
19. Hollman PCH. Evidence for health benefits of plant phenols: local or systemic effects? J. Sci. Food Agric. 2001; 81: 842.
20. Day AJ, Mellon F, Barron D, Sarrazin G, Morgan MRA, Williamson G. Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. Free Rad. Res. 2001; 35: 941.
21. Day AJ, Williamson G. Biomarkers for exposure to dietary flavonoids: a review of the current evidence for identification of quercetin glycosides in plasma. Br. J. Nutr. 2001; 86: S105.
22. Nemeth K, Plumb GW, Berrin JG, Juge N, Jacob R, Naim HY, Williamson G, Swallow DM, Kroon PA. Deglycosylation by small intestinal epithelial cell β-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur. J. Nutr. 2003; 42: 29.
23. Hollman PCH, Arts ICW. Havonols, flavones and flavanols - nature, occurrence and dietary burden. J. Sci. Food Agric. 2000; 80: 1081.
24. Rice-Evans C. Flavonoid antioxidants. Curr. Med. Chem. 2001; 8: 797.
25. Scalbert A, Williamson G. Dietary intake and bioavailability of polyphenols. J. Nutr. 2000; 130: 2073S.
26. Justesen U, Knuthsen P, Leth T. Determination of plant polyphenols in Danish foodstuffs by HPLC-UV and LC-MS detection. Cancer Lett. 1997; 114: 165.
27. Crozier A, Burns J, Aziz AA, Stewart AJ, Rabiasz HS, Jenkins GI, Edwards CA, Lean MEJ. Antioxidant flavonols from fruits, vegetables and beverages: measurements and bioavailability. Biol. Res. 2000; 33: 79.
28. Stobiecki M. Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry 2000; 54: 237.
29. Harborne JB, Mabry TJ. The Flavonoids: Advances in Research. Chapman and Hall: London, 1982.
30. Markham KR. Techniques of Flavonoid Identification. Academic Press: London, 1982.
31. Jay M. In The Flavonoids: Advances in Research Since 1986, Harborne JB (ed). Chapman and Hall: London, 1994.
32. Tura D, Robards K. Sample handling strategies for the determination of biophenols in food and plants. J. Chromatogr. A 2002; 975: 71.
33. Robards K. Strategies for the determination of bioactive phenols in plants, fruits and vegetables. J. Chromatogr. A 2003; 1000: 657.
34. Robards K, Li X, Antolovich M, Boyd S. Characterization of Citrus by chromatographic analysis of flavonoids. J. Sci. Food Agric. 1997; 75: 87.
35. Merken HM, Beecher GR. Measurement of food flavonoids by high performance liquid chromatography: a review. J. Agric. Food Chem. 2000; 48: 577.
36. Rouseff RL, Martin SF, Youtsey CD. Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in Citrus. J. Agric. Food Chem. 1987; 35: 1027.
37. Oliveira EJ, Watson DG. Chromatographic techniques for the determination of putative dietary anticancer compounds in biological fluids. J. Chromatogr. B 2001; 764: 3.
38. Li QM, Dillen L, Claeys M. Positive-ion FAB analysis of flavonoid glycosides-simple procedures for desalting and control of sodium-salt contamination. Biol. Mass Spectrom. 1992; 21: 408.
39. Moraes MDLL, Vilegas JHY, Lancas FM. Supercritical fluid extraction of glycosylated flavonoids from Passiflora leaves. Phytochem. Anal. 1997; 8: 257.
40. Lin MC, Tsai MJ, Wen KC. Supercritical fluid extraction of flavonoids from Scutellariae radix. J. Chromatogr. A 1999; 830: 387.
41. Alonso-Salces RM, Korta E, Barranco A, Berrueta LA, Gallo B, Vicente F. Pressurized liquid extraction for the determination of polyphenols in apple. J. Chromatogr. A 2001; 933: 37.
42. Papagiannopoulos M, Mellenthin A. Automated sample preparation by pressurized liquid extraction-solid-phase extraction for the liquid chromatography - mass spectrometric investigation of polyphenols in the brewing process. J. Chromatogr. A 2002; 976: 345.
43. Satterfield M, Black DM, Brodbelt JS. Detection of the isoflavone aglycones genistein and daidzein in urine using solid-phase microextraction-high-performance liquid chromatography - electrospray ionization mass spectrometry. J. Chromatogr. B 2001; 759: 33.
44. Sparr Eskilsson C, Björklund E. Analytical-scale microwave assisted extraction. J. Chromatogr. A 2000; 902: 227.
45. Carabias-Martínez R, Rodríguez-Gonzalo E, Moreno-Cordero B, Pérez-Pavón JL, García-Pinto C, Fernández Laespada E. Surfactant cloud point extraction and preconcentration of organic compounds prior to chromatography and capillary electrophoresis. J. Chromatogr. A 2000; 902: 251.
46. Smith RM. Before the injection - modern methods of sample preparation for separation techniques. J. Chromatogr. A 2003; 1000: 3.
47. Saito Y, Jinno K. Miniaturized sample preparation combined with liquid phase separations. J. Chromatogr. A 2003; 1000: 53.
48. McGhie TK, Markham KR. Separation of flavonols by capillary electrophoresis: the effect of structure on electrophoretic mobility. Phytochem. Anal. 1994; 5: 121.
49. Aramendia MA, Boráu V, García I, Jiménez C, Lafont F, Marinas JM, Porras A, Urbano FJ. Determination of isoflavones by capillary electrophoresis/electrospray ionization mass spectrometry. J. Mass Spectrom. Rapid Connnun. Mass Spectrom. 1995; S153.
50. Constant HL, Beecher CWW. A method for the dereplication of natural product extracts using electrospray HPLC/MS. Nat. Prod. Lett. 1995; 6: 193.
51. Rauha JP, Vuorela H, Kostiainen R. Effect of eluent on the ionization efficiency of flavonoids by ion spray, atmospheric pressure chemical ionization, and atmospheric pressure photoionization mass spectrometry. J. Mass Spectrom. 2001; 36: 1269.
52. Barnes S, Kirk M, Coward L. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J. Agric. Food Chem. 1994; 42: 2466.
53. n for the dereplication of flavonoids and related compounds in crude plant extracts. Analusis 2000; 28: 895.
54. de Rijke E, Zappey H, Ariese F, Gooijer C, Brinkman UATh. Liquid chromatography with atmospheric pressure chemical ionization and electrospray ionization mass spectrometry of flavonoids with triple-quadrupole and ion-trap instruments. J. Chromatogr. A. 2003; 984: 45.
55. Swatsitang P, Tucker G, Robards K, Jardine D. Isolation and identification of phenolic compounds in Citrus sinensis. Anal. Chim. Acta 2000; 417: 231.
56. Robards K, Antolovich M. Analytical chemistry of fruit bioflavonoids: a review. Analyst 1997; 122: 11R.
57. Cuyckens F, Claeys M. Optimization of a liquid chromatography method based on simultaneous electrospray ionization mass spectrometric and ultraviolet photodiode array detection for analysis of flavonoid glycosides. Rapid Commun. Mass Spectrom. 2002; 16: 2341.
58. Apffel A, Fischer S, Goldberg G, Goodley PC, Kuhlmann FE. Enhanced sensitivity for peptide mapping with electrospray liquid chromatography-mass spectrometry in the presence of signal suppression due to trifluoroacetic acid-containing mobile phases. J. Chromatogr. A 1995; 712: 177.
59. Becchi M, Fraisse D. Fast atom bombardment and fast atom bombardment collision-activated dissociation/mass-analysed ion kinetic energy analysis of C-glycosidic flavonoids. Biomed. Mass Spectrom. 1989; 18: 122.
60. Sägesser M, Deinzer M. HPLC-ion spray-tandem mass spectrometry of flavonol glycosides in hops. J. Am. Soc. Brew. Chem. 1996; 54: 129.
61. Careri M, Elviri L, Mangia A. Validation of a liquid chromatography ionspray mass spectrometry method for the analysis of flavanones, flavones and flavonols. Rapid Commun. Mass Spectrom. 1996; 13: 2399.
62. Mauri PL, Iemoli L, Gardana C, Riso P, Simonetti P, Porrini M, Pietta PG. Liquid chromatography/electrospray ionization mass spectrometric characterization of flavonol glycosides in tomato extracts and human plasma. Rapid Commun. Mass Spectrom. 1999; 13: 924.
63. Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol and flavanone aglycones by negative ion LC-ES ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001; 12: 707.
64. Tian Q, Li D, Patil BS. Identification and determination of flavonoids in buckwheat (Fagopyrum esculentum Moench, Polygonaceae) by high-performance liquid chromatography with electrospray ionisation mass spectrometry and photodiode array ultraviolet detection. Phytochem. Anal. 2002; 13: 251.
65. Harborne JB, Boardley M. Use of high-performance liquid chromatography in the separation of flavonol glycosides and flavonol sulphates. J. Chromatogr. 1984; 299: 377.
66. Greenham J, Williams C, Harborne JB. Identification of lipophilic flavonols by a combination of chromatographic and spectral techniques. Phytochem. Anal. 1995; 6: 211.
67. Schieber A, Keller P, Streker P, Klaiber I, Carle R. Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. 'Brettacher') by HPLC-PDA and HPLC-APCI-MS/MS. Phytochem. Anal. 2002; 13: 87.
68. Crozier A, Jensen E, Lean MEJ, McDonald MS. Quantitative analysis of flavonoids by reversed-phase high-performance liquid chromatography. J. Chromatogr. A 1997; 761: 315.
69. Watson DG, Pitt AR. Analysis of flavonoids in tablets and urine by gas chromatography/mass spectrometry and liquid chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 1998; 12: 153.
70. Mauri P, Pietta P. High performance liquid chromatography/electrospray mass spectrometry of Hypericum perforatum extracts. Rapid Commun. Mass Spectrom. 2000; 14: 95.
71. Huck CW, Buchmeiser MR, Bonn GK. Fast analysis of flavonoids in plant extracts by liquid chromatography-ultraviolet absorbance detection on poly(carboxylic acid)-coated silica and electrospray ionization tandem mass spectrometric detection. J. Chromatogr. A 2001; 943: 33.
72. Hansen SH, Jensen AG, Cornett C, Bjømsdottir I, Taylor S, Wright B, Wilson ID. High-performance liquid chromatography on-line coupled to high-field NMR and mass spectrometry for structure elucidation of constituents of Hypericum perforatum L. Anal. Chem. 1999; 71: 5235.
73. Lommen A, Godejohann M, Venema DP, Hollman PCH, Spraul M. Application of directly coupled HPLC-NMR-MS to the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel. Anal. Chem. 2000; 72: 1793.
74. Mabry TJ, Markham KR. In The Flavonoids, Harborne JB (ed). Academic Press: New York, 1975; 197.
75. Mabry TJ, Ulubelen A. In Biochemical Applications of Mass Spectrometry, Walker GR, Dermer O (eds). Wiley: New York, 1980; 1131.
76. Hedin PA, Philips VA. Electron-impact mass-spectral analysis of flavonoids. J. Agric. Food Chem. 1992; 40: 607.
77. Ma YL, Li QM, Van den Heuvel H, Claeys M. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1997; 11: 1357.
78. Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj. J. 1988; 5: 397.
79. Takayama M, Fukai T, Hann Y, Nomura T. Mass spectrometry of prenylated flavonoids. Heterocycles 1992; 33: 405.
80. Takayama M, Fukai T, Ichikawa K, Nomura T. Identification of prenylated flavonoids using fast-atom bombardment mass spectrometry. Rapid Commun. Mass Spectrom. 1991; 5: 67.
81. Stevens JF, Ivancic M, Hsu VL, Deinzer ML. Prenylflavonoids from Humulus lupulus. Phytochemistry 1997; 44: 1575.
82. Hughes RJ, Croley TR, Metcalfe CD, March RE. A tandem mass spectrometric study of selected characteristic flavonoids. Int. J. Mass Spectrom. 2001; 210/211: 371.
83. Cuyckens F, Ma YL, Pocsfalvi G, Claeys M. Tandem mass spectral strategies for the structural characterization of flavonoid glycosides. Analusis 2000; 28: 888.
84. Justesen U. Collision-induced fragmentation of deprotonated methoxylated flavonoids, obtained by electrospray ionization mass spectrometry. J. Mass Spectrom. 2001; 36:169.
85. Li QM, Claeys M. Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 1994; 23: 406.
86. Wolfender JL, Maillard M, Marston A, Hostettmann K. Mass spectrometry of underivatized naturally occuring glycosides. Phytochem. Anal. 1992; 3:193.
87. Constant HL, Slowing K, Graham JG, Pezzuto JM, Cordell GA, Beecher CWW. A general method for the dereplication of flavonoid glycosides utilizing high performance liquid chromatography/mass spectrometric analysis. Phytochem. Anal. 1997; 8:176.
88. Hvattum E. Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode array detection. Rapid Commun. Mass Spectrom. 2002; 16: 655.
89. Hvattum E, Ekeberg D. Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. J. Mass Spectrom. 2003; 38: 43.
90. Kéki S, Deák G, Zsuga M. Fragmentation study of rutin, a naturally occurring flavone glycoside cationized with different alkali metal ions, using post-source decay matrix-assisted laser desorption/ionization mass spectrometry. J. Mass Spectrom. 2001; 36: 1312.
91. Ma YL, Van den Heuvel H, Vedernikova I, Claeys M. Internal glucose residue loss in protonated O-cliglycosyl flavonoids upon low-energy collision-induced dissociation. J. Am. Soc. Mass Spectrom. 2000; 11: 136.
92. Cuyckens F, Rozenberg R, de Hoffmann E, Claeys M. Structure characterization of flavonoid O-cliglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry. J. Mass Spectrom. 2001; 36: 1203.
93. Kováčik V, Pätoprstý V, Havliček V, Kováč P. Matrix-assisted laser desorption/ ionization and electrospray ionization mass spectrometry: sodium-cationized oligosaccharides do not exhibit 'internal-residue loss' rearrangement. Eur. Mass Spectrom. 1998; 4: 417.
94. Brüll LP, Kováčik V, Thomas-Oates JE, Heerma W, Haverkamp J. Sodium-cationized oligosaccharides do not appear to undergo 'internal residue loss' rearrangement processes on tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1998; 12: 1520.
95. Ma YL, Cuyckens F, Van den Heuvel H, Claeys M. Mass spectrometric methods for the characterisation and differentiation of isomeric O-diglycosyl flavonoids. Phytochem. Anal. 2001; 12: 159.
96. Sakushima A, Nishibe S, Brandenberger H. Negative ion desorption chemical ionization spectrometry of flavonoid glycosides. Biomed. Environ. Mass Spectrom. 1989; 18: 809.
97. Satterfield M, Brodbelt JS. Structural characterization of flavonoid glycosides by collisionally activated dissociation of metal complexes. J. Am. Soc. Mass Spectrom. 2001; 12: 537.
98. Satterfield M, Brodbelt JS. Enhanced detection of flavonoids by metal complexation and electrospray ionization mass spectrometry. Anal. Chem. 2000; 72: 5898.
99. Sakushima A, Nishibe S, Takeda T, Ogihara Y. Positive and negative ion mass spectra of flavonoid glycosides by fast atom bombardment. Mass Spectrosc. 1988; 36: 71.
100. Grayer RJ, Kite GC, Abou-Zaid M, Archer LJ. The application of atmospheric pressure chemical ionisation liquid chromatography - mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum. Phytochem. Anal. 2000; 11: 257.
101. Geiger H, Schwinger G. Felddesorptions-massenspektrometrie und thermische fragmentierung von flavonoidglykosiden. Phytochemistry 1980; 19: 897.
102. Claeys M, Li QM, Van den Heuvel H, Dillen L. In Applications of Modern Mass Spectrometry in Plant Sciences, Newton RP, Walton TJ (eds). Clarendon Press: Oxford 1996; 182.
103. Chen X, Wang H, Du Y, Zhong D. Quantification of the flavonoid wogonin and its major metabolite wogonin-7β-D-glucuronide in rat plasma by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B 2002; 775: 169.
104. Cuyckens F, Shahat AA, Pieters L, Claeys M. Direct stereochemical assignment of hexose and pentose residues in flavonoid β-glycosides by fast atom bombardment and electrospray ionization mass spectrometry. J. Mass Spectrom. 2002; 12: 1272.
105. Li QM, Van den Heuvel H, Dillen L, Claeys M. Differentiation of 6-C and 8-C-glycosidic flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 1992; 21: 213.
106. Sńchez-Rabaneda F, Jáuregui O, Casals I, Andrés-Lacueva C, Izquierdo-Pulido M, Lamuela-Raventós RM. Liquid chromatography/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). J. Mass Spectrum. 2003; 38: 35.
107. Bylka W, Franski R, Stobiecki M. Differentiation between isomeric acacetin-6-C-(6″-O-malonyl)glucoside and acacetin-8-C-(6″-O-malonyl)glucoside by using low-energy CID mass spectra. J. Mass Spectrom. 2002; 37: 648.
108. Waridel P, Wolfender JL, Ndjoko K, Hobby KR, Major HJ, Hostettmann K. Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J. Chromatogr. A 2001; 926: 29.
109. Rath G, Touré A, Nianga M, Wolfender JL, Hostettmann K. Characterization of C-glycosylflavones from Dossotis rotundifolia by liquid chromatography - UV diode array detection - tandem mass spectrometry. Chromatographia 1995; 41: 332.
110. Li QM, Van den Heuvel H, Delorenzo O, Corthout J, Pieters LAC, Vlietinck AJ, Claeys M. Mass spectral characterization of C-glycosidic flavonoids isolated from a medicinal plant (Passiflora incarnata). J. Chromatogr. B 1991; 562: 435.
111. Cuyckens F, Shahat AA, Van den Heuvel H, Abdel-Shafeek KA, El-Messiry MM, Seif-El Nasr MM, Pieters L, Vlietinck AJ, Claeys M. The application of liquid chromatography-electrospray ionization mass spectrometry and collision-induced dissociation in the structural characterization of acylated flavonol O-glycosides from the seeds of Carrichtera annua. Eur. J. Mass Spectrom. 2003; 9: 409.
112. Haribal M, Renwick JAA, Attygalle A. A new sinapoyl derivative of isovitexin 6″-O-β-D-glucopyranoside from Alliaria petiolata. J. Nat. Prod. 1999; 62: 179.
113. Glässgen WE, Seitz HU, Metzger JW. High-performance liquid chromatography/electrospray mass spectrometry and tandem mass spectrometry of anthocyanins from plant tissues and cell cultures of Daucus carota L. Biol. Mass Spectrom. 1992; 21: 271.
114. Fossen T, Øvstedal DO, Slimestad R, Andersen ØM. Anthocyanins from a Norwegian potato cultivar. Food Chem. 2003; 81: 433.
115. Damu AG, Jayaprakasam B, Gunasekar D, Blond A, Bodo B. Two acylated flavone glucosides from Andrographis serpyllifolia. Phytochemistry 1999; 52: 147.
116. Dougall DK, Baker DC, Gakh EG, Redus MA, Whittemore NA. Anthocyanins from wild carrot suspension cultures acylated with supplied carboxylic acids. Carbohydr. Res. 1998; 310: 177.
117. Lin LZ, He XG, Lindenmaier M, Nolan G, Yang J, Cleary M, Qiu SX, Cordell GA. Liquid chromatography - electrospray ionization mass spectrometry study of the flavonoids of the roots of Astragalus mongholicus and A. membranaceus. J. Chromatogr. A 2000; 876: 87.
118. de Rijke E, Zafra-Gómez A, Ariese F, Brinkman UATh, Gooijer C. Determination of isoflavone glucoside malonates in Trifolium pratense L. (red clover) extracts: quantification and stability studies. J. Chromatogr. A 2001; 932: 55.
119. Slimestad R, Hostettmann K. Characterisation of phenolic constituents from juvenile and mature needles of Norway spruce by means of high performance liquid chromatography-mass spectrometry. Phytochem. Anal. 1996; 7: 42.
120. Klejdus B, Vitamvásová-Štěrbová D, Kubáň V. Identification of isoflavone conjugates in red clover (Trifolium pratense) by liquid chromatography-mass spectrometry after two-dimensional solid-phase extraction. Anal. Chim. Acta 2001; 450: 81.
121. Stobiecki M, Malosse C, Kerhoas L, Wojlaszek P, Einhorn J. Detection of isoflavonoids and their glycosides by liquid chromatography/electrospray ionization mass spectrometry in root extracts of Lupin (Lupinus albus). Phytochem. Anal. 1999; 10: 198.
122. Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA. LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). J. Agric. Food Chem. 2000; 48: 354.
123. Ducrey B, Wolfender JL, Marston A, Hostettmann K. Analysis of flavonol glycosides of thirteen Epilobium species (Onagraceae) by LC-UV and thermospray LC-MS. Phytochemistry 1995; 38: 129.
124. Gariboldi E, Mascetti D, Galli G, Caballion P, Bosisio E. LC-UV-electrospray-MS-MS mass spectrometry analysis of plant constituents inhibiting xanthine oxidase. Pharm. Res. 1998; 15: 936.
125. Mahmoud II, Marzouk MSA, Moharram FA, El-Gindi MR, Hassan AMK. Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemishy 2001; 58: 1239.
126. Wang H, Race EJ, Shrikhande J. Characterization of anthocyanins in grape juices by ion trap liquid chromatography-mass spectrometry. J. Agric. Food Chem. 2003; 51: 1839.
127. Tamura H, Hayashi Y, Sugisawa H, Kondo T. Structure determination of acylated anthocyanins in muscat baily A grapes by homonuclear Hartmann-Hahn (HOHAHA) spectroscopy and liquid chromatography-mass spectrometry. Phytochem. Anal. 1994; 5: 190.
128. dos Santos LC, Piacente S, Pizza C, Toro R, Sano PT, Vilegas W. 6-methoxyquercetin-3-O-(6″-E-feruloyl)-β-D-glucopyranoside from Paepalanthus polyanthus (Eriocaulaceae). Biochem. Syst. Ecol. 2002; 30: 451.