Optimisation of ESI-MS detection for the HPLC of anthraquinone dyes

Rafaëlly, L.; Héron, Sylvie; Nowik, Witold; Tchapla, Alain

doi:10.1016/j.dyepig.2007.05.007

Cited by 92 publications

(65 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…There are many literature references that have separated the compounds in madder using an HPLC apparatus and several others that have used an older method of DCCC (droplet counter current chromatography) (Hostettmann, 1980;Derksen et al, 1998;Derksen and van Beek, 2002;Rafaëlly et al, 2008;Bechtold, 2009;Slyshova et al, 2010). The amount of pure dye compounds recovered by these processes is in the magnitude of several milligrams; with this recovery being so low, limited analysis work has been performed on anthraquinone glycosides.…”

Section: Figure 1 Anthraquinone Structures Found In Rubia Tinctorummentioning

confidence: 99%

Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation

2013

View full text Add to dashboard Cite

Madder (Rubia tinctorum L.) has been used as a dye for over 2000 years with alizarin and purpurin the major natural dyes analysed from extractions undertaken. The use of ethanol as the solvent in the extraction process produced an extract that yielded four anthraquinone compounds lucidin primeveroside, ruberythric acid, alizarin and lucidin--ethyl ether.Gravitational separation of the extract was used to record the first crystal structure of lucidin primeveroside and the first ever known crystal structure of a glycoside containing anthraquinone moiety. The crystal structure along with 1 H and 13 C NMR helped elucidate and confirm the structure of this overlooked natural dye which has been shown to be a major compound in Rubia tinctorum L.

show abstract

Section: Figure 1 Anthraquinone Structures Found In Rubia Tinctorummentioning

confidence: 99%

Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation

2013

View full text Add to dashboard Cite

show abstract

“…Dye analysis is usually performed by liquid chromatography with a diode array detector [6][7][8][9][10][11], but nowadays, mass detection is becoming increasingly important [12][13][14][15][16][17][18][19][20]. A successful approach to identify natural dyes requires that, prior to the chromatographic analysis, an adequate analytical methodology is used for their extraction from the textile fibres.…”

Section: Introductionmentioning

confidence: 99%

Extracting natural dyes from wool—an evaluation of extraction methods

et al. 2011

View full text Add to dashboard Cite

The efficiency of eight different procedures used for the extraction of natural dyes was evaluated using contemporary wool samples dyed with cochineal, madder, woad, weld, brazilwood and logwood. Comparison was made based on the LC-DAD peak areas of the natural dye's main components which had been extracted from the wool samples. Among the tested methods, an extraction procedure with Na 2 EDTA in water/DMF (1:1, v/v) proved to be the most suitable for the extraction of the studied dyes, which presented a wide range of chemical structures. The identification of the natural dyes used in the making of an eighteenth century Arraiolos carpet was possible using the Na 2 EDTA/DMF extraction of the wool embroidery samples and an LC-DAD-MS methodology. The effectiveness of the Na 2 EDTA/DMF extraction method was particularly observed in the extraction of weld dye components. Nine flavone derivatives previously identified in weld extracts could be identified in a single historical sample, confirming the use of this natural dye in the making of Arraiolos carpets. Indigo and brazilwood were also identified in the samples, and despite the fact that these natural dyes were referred in the historical recipes of Arraiolos dyeing, it is the first time that the use of brazilwood is confirmed. Mordant analysis by ICP-MS identified the widespread use of alum in the dyeing process, but in some samples with darker hues, high amounts of iron were found instead.

show abstract

“…The positive mode is the most commonly used for spectra acquisition in MALDI because the protonation generally creates mono-charged species and the mass spectra obtained are characterized by a higher reproducibility in comparison to negative mode ones [32,33].…”

Section: Maldi-tof-msmentioning

confidence: 99%

A Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Method for the Identification of Anthraquinones: the Case of Historical Lakes

Sabatini

Lluveras‐Tenorio

Degano

et al. 2016

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Abstract. This study deals with the identification of anthraquinoid molecular markers in standard dyes, reference lakes, and paint model systems using a micro-invasive and nondestructive technique such as matrix-assisted laser desorption/ionization time-of-flight-mass spectrometry (MALDI-ToF-MS). Red anthraquinoid lakes, such as madder lake, carmine lake, and Indian lac, have been the most widely used for painting purposes since ancient times. From an analytical point of view, identifying lakes in paint samples is challenging and developing methods that maximize the information achievable minimizing the amount of sample needed is of paramount importance. The employed method was tested on less than 0.5 mg of reference samples and required a minimal sample preparation, entailing a hydrofluoric acid extraction. The method is fast and versatile because of the possibility to re-analyze the same sample (once it has been spotted on the steel plate), testing both positive and negative modes in a few minutes. The MALDI mass spectra collected in the two analysis modes were studied and compared with LDI and simulated mass spectra in order to highlight the peculiar behavior of the anthraquinones in the MALDI process. Both ionization modes were assessed for each species. The effect of the different paint binders on dye identification was also evaluated through the analyses of paint model systems. In the end, the method was successful in detecting madder lake in archeological samples from Greek wall paintings and on an Italian funerary clay vessel, demonstrating its capabilities to identify dyes in small amount of highly degraded samples.

show abstract

Optimisation of ESI-MS detection for the HPLC of anthraquinone dyes

Cited by 92 publications

References 18 publications

Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation

Isolation and extraction of lucidin primeveroside from Rubia tinctorum L. and crystal structure elucidation

Extracting natural dyes from wool—an evaluation of extraction methods

A Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Method for the Identification of Anthraquinones: the Case of Historical Lakes

Contact Info

Product

Resources

About