Characterization of Organic Natural Dyes by Electrospray Mass Spectrometry Coupled with HPLC and/or Capillary Electrophoresis

Organic Mass Spectrometry in Art and Archaeology

Volumn , Issue , 2009, Pages 363-388

  Lech, Katarzyna ^a   Połeć Pawlak, Katarzyna ^a   Jarosz, Maciej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Anthraquinones and flavonoids in plants as polar glycosides; Atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI); Blue violet dye analysis; Capillary electrophoresis (CE) with selective detection units; HPLC ESI MS tool in non anthraquinone red dyestuff analysis; Organic natural dye characterization; Red dyes analysis; Sample preparation; Yellow and brown dye analysis

Indexed keywords

EID: 84889326395     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470741917.ch13     Document Type: Chapter

References (64)

1. A.P. Bruins, T.R. Covey and J.D. Henion, Ionspray interface for combined liquid chromatography/atmospheric pressure ionization mass spectrometry, Anal. Chem., 59,2642-2646(1987).
2. G. Hopfgartner, T. Wachs, K. Bean and J. Henion, High-flow ion spray liquid chromatography/mass spectrometry, Anal. Chem., 65,439-446(1993).
3. I. Zadrozna, K. Połeć-Pawlak, I.Głuch, M.A. Ackacha, M. Mojski, J. Witowska-Jarosz and M. Jarosz, Oldmaster paintings-a fruitful field of activity for analysts: targets, methods, outlook, J. Sep. Sci., 26,996-1004(2003).
4. E. Rosenberg, Characterisation of historical organic dyestuffs by liquid chromatography-mass spectrometry, Anal. Bioanal. Chem., 391,33-57(2008).
5. R. Blanc, T. Espejo, A. López-Montes, D. Torres, G. Crovetto, A. Navalón and J.L.Vílchez, Samplingand identification of natural dyes in historical maps and drawings by liquid chromatography with diode-array detection, J. Chromatogr. A, 1112,105-113(2006).
6. X. Zhang and R.A. Laursen, Developmentof mild extraction methods for the analysis of natural dyes in textiles of historical interest using LC-diode array detector-MS, Anal. Chem., 77,2022-2025(2005).
7. X. Zhang, R. Boytner, J.L. Cabrera and R. Laursen, Identificationof yellow dye types in pre-Columbian Andean textiles, Anal. Chem., 79,1575-1582(2007).
8. L. Rafaëlly, S. Héron, W. Nowik and A. Tchapla, Optimisationof ESI-MS detection for the HPLC of anthraquinone dyes, Dyes and Pigments, 77,191-203(2008).
9. J.K. Prasain, C.H. Wang and S. Barnes, Massspectrometric methods for the determination of flavonoids in biological samples, Free Radic. Biol. Med., 37,1324-1350(2004).
10. S.F.Y. Li, CapillaryElectrophoresis: Principles, Practice and Applications, Elsevier, Amsterdam (1992).
11. P. Jandik and G. Bonn, CapillaryElectrophoresis of Small Molecules and Ions, VCH Publishers, New York (1993).
12. R. Weinberger, PracticalCapillary Electrophoresis, Academic Press, San Diego (1993).
13. S.C. Beale, Capillaryelectrophoresis, Anal. Chem., 70,279R-300R (1998).
14. P. Schmitt-Kopplin, CapillaryElectrophoresis. Methods and Protocols, Humana Press, Neuherberg (2008).
15. M. Trojanowicz, L. Wójcik and K. Urbaniak-Walczak, Identificationof natural dyes in historical Coptic textiles by capillary electrophoresis with diode array detection, Chem. Anal. (Warsaw), 48,607-620(2003).
16. M. Zougagh, B.M. Simonet, A. Ríos and M. Valcárcel, Useof non-aqueous capillary electrophoresis for the quality control of commercial saffron samples, J. Chromatogr., A, 1085,293-298(2005).
17. Y. Li, S. Qi, X. Chen and Z. Hu, Separationand determination of the anhraquinones in Xanthophytum attopvensis pierre by nonaqueous capillary electrophoresis, Talanta, 65,15-20(2005).
18. A. López-Montes, R.B. García, T. Espejo, J.F. Huertas-Perez, A. Navalón and J.L. Vílchez, Simultaneousidentification of natural dyes in the collection of drawings and maps from The Royal Chancellery Archives in Granada (Spain) by CE, Electrophoresis, 28,1243-1251(2007).
19. M.A. Ackacha, K. Połeć-Pawlak and M. Jarosz, Identification of anthraquinone coloring matters in natural red dyestuffs by high performance liquid chromatography with ultraviolet and electrospray mass spectrometric detection, J. Sep. Sci., 26,1028-1034(2003).
20. M. Puchalska, M. Orlińska, M.A. Ackacha, K. Połeć-Pawlak and M. Jarosz, Identification of anthraquinone coloring matters in natural red dyes by electrospray mass spectrometry coupled to capillary electrophoresis, J. Mass Spectrom., 38,1252-1258(2003).
21. D. Cristea, I. Bareau and G.Vilarem, Identification and quantitative HPLC analysis of the main flavonoids present in weld (Reseda luteola L.), Dyes and Pigments, 57,267-272(2003).
22. P.A. Tarantilis, G. Tsoupras and M. Polissiou, Determination of saffron (Crocus sativus L.) components in crude plant extract using high-performance liquid chromatography-UV-visible photodiode-array detection-mass spectrometry, J. Chromatogr. A, 699,107-118(1995).
23. X.G. He, L.Z. Lin, L.Z. Lian and M. Lindenmaier, Liquid chromatography-electrospray mass spectrometric analysis of curcuminoids and sesquiterpenoids in turmeric (Curcuma longa), J. Chromatogr., A, 818,127-132(1998).
24. P. Lozano, M.R. Castellar, M.J. Simancas and J.L. Iborra, Quantitative high-performance liquid chromatographic method to analyse commercial saffron (Crocus sativus L.) products, J. Chromatogr., A, 830,477-483(1999).
25. H. Jiang, B.N. Timmermann and D.R. Gang, Use of liquid chromatography-electrospray ionization tandem mass spectrometry to identify diarylheptanoids in turmeric (Curcuma longa L.) rhizome, J. Chromatogr. A, 1111,21-31(2006).
26. H. Jiang, A. Somogyl, N.E. Jacobsen, B.N. Timmermann and D.R. Gang, Analysis of curcuminoids by positive and negative electrospray ionization and tandem mass spectrometry, Rapid Commun. Mass Spectrom., 20,1001-1012(2006).
27. S. Häkkinen and S. Auriola, High-performance liquid chromatography with electrospray ionization mass spectrometry and diode array ultraviolet detection in the identification of flavonol aglycones and glycosides in berries, J. Chromatogr. A, 829,91-100(1998).
28. P. Novotná, V. Pacáková, Z. Bosáková and K. Stulík, High-performance liquid chromatographic determination of some anthraquinone and naphthoquinone dyes occurring in historical textiles, J. Chromatogr. A, 863,235-241(1999).
29. E.S.B. Ferreira, A. Quye, H. McNab, A.N. Hulme, J. Wouters and J.J. Boon, Development of analytical techniques for the study of natural yellow dyes in historic textiles, Dyes in History and Archaeology, 16/17,179-186(2001).
30. E.S.B. Ferreira, A. Quye, H. McNab and A.N. Hulme, Photo-oxidation products of quercetin and morin as markers for the characterisation of natural flavonoid yellow dyes in ancient textiles, Dyes in History and Archaeology, 18,63-72(2002).
31. B. Szostek, J. Orska-Gawryś, I. Surowiec and M. Trojanowicz, Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection, J. Chromatogr. A, 1012,179-192(2003).
32. M. Trojanowicz, J. Orska-Gawryś, I. Surowiec, B. Szostek, K. Urbaniak-Walczak, J. Kehl and M. Wróbel, Chromatographic investigation of dyes extracted from Coptic textiles from the National Museum in Warsaw, Stud. Conserv., 49,115-130(2004).
33. G.G. Balakina, V.G. Vasiliev, E.V. Karpova and V.I. Mamatyuk, HPLC and molecular spectroscopic investigations of the red dye obtained from an ancient Pazyryk textile, Dyes and Pigments, 71,54-60(2006).
34. I. Karapanagiotis and Y. Chryssoulakis, Investigation of red natural dyes used in historical objects by HPLC-DAD-MS, Annal. Chim., 96,75-84(2006).
35. I. Surowiec, A. Quye and M. Trojanowicz, Liquid chromatography determination of natural dyes in extracts from historical Scottish textiles excavated from peat bogs, J. Chromatogr. A, 1112,209-217(2006).
36. I. Karapanagiotis, L. Valianou, S. Daniilia and Y. Chryssoulakis, Organic dyes in Byzantine and post-Byzantine icons from Chalkidiki (Greece), J. Cult. Herit., 8,294-298(2007).
37. I. Surowiec, B. Szostek and M. Trojanowicz, HPLC-MS of anthraquinoids, flavonoids, and their degradation products in analysis of natural dyes in archeological objects, J. Sep. Sci., 30,2070-2079(2007).
38. G.C.H. Derksen, H.A.G. Niederländer and T.A. van Beek, Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection, J. Chromatogr. A, 978,119-127(2002).
39. G.C.H. Derksen, M. Naayer, T.A. van Beek, A. Capelle, I.K. Haaksman, H.A. van Doren and Æ. Groot, Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots, Phytochem. Anal., 14,137-144(2003).
40. G.C.H. Derksen, G.P. Lelyveld, T.A. van Beek, A. Capelle and Æ. Groot, Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars, Phytochem. Anal., 15,397-406(2004).
41. J. Sanyova and J. Reisse, Development of a mild method for the extraction of anthraquinones from their aluminum complexes in madder lakes prior to HPLC analysis, J. Cult. Herit., 7,229-235(2006).
42. I. Boldizsár, Z. Szucs, Z. Füzfai and I. Molnár-Perl, Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography, J. Chromatogr. A, 1133,259-274(2006).
43. I. Karapanagiotis, Identification of indigoid natural dyestuffs used in art objects by HPLC coupled to APCI-MS, Am. Lab., 38,36-40(2006).
44. M. Puchalska, K. Połeć-Pawlak, I. Zadrozna, H. Hryszko and M. Jarosz, Identification of indigoid dyes in natural organic pigments used in historical art objects by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry, J. Mass Spectrom., 39,1441-1449(2004).
45. K. Pawlak, M. Puchalska, A. Miszczak, E. Rosłoniec and M. Jarosz, Blue natural organic dyestuffs-from textile dyeing to mural painting. Separation and characterization of coloring matters present in elderberry, logwood and indigo, J. Mass Spectrom., 41,613-622(2006).
46. T. Maugard, E. Enaud, P. Choisy and M.D. Legoy, Identification of an indigo precursor from leaves of Isatis tinctoria (Woad), Phytochemistry, 58,897-904(2001).
47. A.N. Assimopoulou, I. Karapanagiotis, A. Vasiliou, S. Kokkini and V.P. Papageorgiou, Analysis of alkannin derivatives from Alkanna species by high-performance liquid chromatography/photodiode array/mass spectrometry, Biomed. Chromatogr., 20,1359-1374(2006).
48. J.P. Salminen, V. Ossipov, J. Loponen, E. Haukioja and K. Pihlaja, Characterisation of hydrolysable tannins from leaves of Batula pubescens by high-performance liquid chromatographymass spectrometry, J. Chromatogr. A, 864,283-291(1999).
49. M. Carmona, A.M. Sánchez, F. Ferreres, A. Zalacain, F. Tomás-Barberán and G.L. Alonso, Identification of the flavonoid fraction in saffron spice by LC/DAD/MS/MS: comparative study of samples from different geographical origins, Food Chem., 100,445-450(2007).
50. G.C.H. Derksen , T.A. van Beek, Æ. Groot and A. Capelle, High-performance liquid chromatographic method for the analysis of anthraquinone glycosides and aglycones in madder root (Rubia tinctorum L.), J. Chromatogr. A, 816,277-281(1998).
51. J. Wouters, The dye of Rubia peregrina, Dyes in History and Archaeology, 16/17,145-157(2001).
52. J. Méndez, M. González, M.G. Lobo and A. Carnero, Color quality of pigments in cochineals (Dactylopius coccus Costa). Geographical origin characterization using multivariate statistical analysis, J. Agric. Food Chem., 52,1331-1337(2004).
53. M. González, M.G. Lobo, J. Méndez and A. Carnero, Detection of colour adulteration in cochineals by spectrophotometric determination of yellow and red pigment groups, Food Control, 16,105-112(2005).
54. R. White and J. Kirby, Preliminary research into lac lake pigments using HPLC/electrospray mass spectrometry, Dyes in History and Archaeology, 16/17,167-178(2001).
55. F.L. Liu, C.Y.W. Ang, T.M. Heinze, J.D. Rankin, R.D. Beger, J.P. Freeman and J.O. Lay Jr, Evaluation of major active components in St. John's Wort dietary supplements by highperformance liquid chromatography with photodiode array detection and electrospray mass spectrometric confirmation, J. Chromatogr. A, 888,85-92(2000).
56. V. Carbone, P. Montoro, N. de Tommasi and C. Pizza, Analysis of flavonoids from Cyclanthera pedata fruits by liquid chromatography/electrospray mass spectrometry, J. Pharmaceut. Biomed., 34,295-304(2004).
57. M.-J. Dubber, V. Sewram, N. Mshicileli, G.S. Shephard and I. Kanfer, The simultaneous determination of selected flavonol glycosides and aglycones in Ginkgo biloba oral dosage forms by high-performance liquid chromatography-electrospray ionization-mass spectrometry, J. Pharmaceut. Biomed., 37,723-731(2005).
58. S. Kazuno, M. Yanagida, N. Shindo and K. Murayama, Mass spectrometric identification and quantification of glycosyl flavonoids, including dihydrochalcones with neutral loss scan mode, Anal. Biochem., 347,182-192(2005).
59. N. Li, G. Lin, Y.W. Kwan and Z.D. Min, Simultaneous quantification of five major biologically active ingredients of saffron by high-performance liquid chromatography, J. Chromatogr. A, 849,349-355(1999).
60. J. Wouters and N. Rosario-Chirinos, Dye analysis of pre-Columbian Peruvian textiles with highperformance liquid chromatography and diode array detection, J. Am. Inst. Conserv., 31,237-255(1992).
61. K.G. Gilbert, D.J. Hill, C. Crespo, A. Mas, M. Lewis, B. Rudolph and D.T. Cooke, Qualitative analysis of indigo precursors from woad by HPLC and HPLC-MS, Phytochem. Anal., 11,18-20(2000).
62. B.C. Liau, T.T. Jong, M.R. Lee and S.S. Chen, LC-APCI-MS method for detection and analysis of tryptanthrin, indigo, and indirubin in daqingye and banlangen, J. Pharm. Biomed. Anal., 43,346-351(2007).
63. A.R.S. Ross, M.G. Ikonomou and K.J. Orians, Characterization of dissolved tannins and their metal-ion complexes by electrospray ionization mass spectrometry, Anal. Chim. Acta, 411,91-102(2000).
64. Y.Y. Soong and P.J. Barlow, Isolation and structure elucidation of phenolic compounds from longan (Dimocarpus longan Lour.) seed by high-performance liquid chromatographyelectrospray ionization mass spectrometry, J. Chromatogr. A, 1085,270-277(2005).