Identification of orcein and selected natural dyes in 14th and 15th century liturgical paraments with high-performance liquid chromatography coupled to the electrospray ionization tandem mass spectrometry (HPLC-ESI/MS/MS)

Witkowski, Bartłomiej; Ganeczko, Monika; Hryszko, Helena; Stachurska, Monika; Gierczak, Tomasz; Biesaga, Magdalena

doi:10.1016/j.microc.2017.03.049

Cited by 31 publications

(18 citation statements)

References 43 publications

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“…Most HPLC methods published to date have been dedicated to identifying specific groups of colorants, such as anthraquinones from madder and scale insects [ 7 , 8 , 9 , 10 , 11 , 14 , 17 , 18 , 19 , 20 , 21 , 22 , 30 , 31 ] or indigoids [ 5 , 7 , 8 , 9 , 11 , 12 , 13 , 14 , 15 , 16 , 20 , 21 , 32 ], whereas only one was about orchil colorants [ 33 , 34 , 35 ]. However, it appears that there are no reports devoted to sandalwood colorants.…”

Section: Introductionmentioning

confidence: 99%

A Mass Spectrometry-Based Approach for Characterization of Red, Blue, and Purple Natural Dyes

Lech

Fornal

2020

Molecules

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Effective analytical approaches for the identification of natural dyes in historical textiles are mainly based on high-performance liquid chromatography coupled with spectrophotometric detection and tandem mass spectrometric detection with electrospray ionization (HPLC-UV-Vis-ESI MS/MS). Due to the wide variety of dyes, the developed method should include an adequate number of reference color compounds, but not all of them are commercially available. Thus, the present study was focused on extending of the universal analytical HPLC-UV-Vis-ESI MS/MS approach to commercially unavailable markers of red, purple, and blue dyes. In the present study, HPLC-UV-Vis-ESI MS/MS was used to characterize the colorants in ten natural dyes (American cochineal, brazilwood, indigo, kermes, lac dye, logwood, madder, orchil, Polish cochineal, and sandalwood) and, hence, to extend the analytical method for the identification of natural dyes used in historical objects to new compounds. Dye markers were identified mostly on the basis of triple quadrupole MS/MS spectra. In consequence, the HPLC-UV-Vis-ESI MS/MS method with dynamic multiple reaction monitoring (dMRM) was extended to the next 49 commercially unavailable colorants (anthraquinones and flavonoids) in negative ion mode and to 11 (indigoids and orceins) in positive ion mode. These include protosappanin B, protosappanin E, erythrolaccin, deoxyerythrolaccin, nordamnacanthal, lucidin, santalin A, santalin B, santarubin A, and many others. Moreover, high-resolution QToF MS data led to the establishment of the complex fragmentation pathways of α-, β-, and γ- aminoorceins, hydroxyorceins, and aminoorceinimines extracted from wool dyed with Roccella tinctoria DC. The developed approach has been tested in the identification of natural dyes used in 223 red, purple, and blue fibers from 15th- to 17th-century silk textiles. These European and Near Eastern textiles have been used in vestments from the collections of twenty Krakow churches.

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Section: Introductionmentioning

confidence: 99%

A Mass Spectrometry-Based Approach for Characterization of Red, Blue, and Purple Natural Dyes

Lech

Fornal

2020

Molecules

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“…However, indirubin is absent, and indigotin with trace isatin are detected in sample 3. According to Witkowski (), this result relates to the plant species of indigo and indicates that the blue dye probably originates from woad ( Isatis tinctoria L.).…”

Section: Resultsmentioning

confidence: 98%

Characterizations of palace lantern tassels preserved in The Palace Museum, Beijing, by UPLC‐ESI‐Q‐TOF

et al. 2020

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Palace lanterns were important and highly visible decorations in the imperial palace in Beijing, China, during the Qing dynasty (1636-1912. Most lanterns had colourful tassels made of fibres. The study performed a comprehensive investigation of the materials and dyes used for palace lantern tassels preserved in The Palace Museum, Beijing. Eight samples with different colours, including yellow, green and red, from five palace lanterns were analysed. By using ultra-performance liquid chromatography combined with time-of-flight mass spectrometry, the compositions of the dyes were identified quickly, and thus the dyes' origins were explored. A Xray fluorescence spectrometer assisted in the detection of whether a mordant was used during the dyeing process. As a result, the tassels were all made of silk, discovered through the use of microscopic observation and micro-Fourier transform infrared spectrometry analysis. Different dyeing techniques were found in these tassels: yellow tassels were dyed by cork tree or turmeric by a direct dyeing method; greens were dyed by pagoda bud with an iron mordant, or by the combination of cork tree and indigo using multi-dyeing method; and red tassels were coloured with different acid red industrial dyes. These results provide valuable data for the conservation of ancient textile tassels and contribute to the investigation of other hanging tags.

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“…Postcolumn complexation of anthraquinone dyes with gallium ions has been used in their determination in extracts from Coptic textiles [134,174] and with zirconyl ions in extracts from th century tapestry from Aubusson (Table 5) [175]. ESI is the most important soft ionization technique in the analysis of anthraquinone dyes due to their polar nature [32,51,141,147,151,[177][178][179][180][181], though APCI has also been used in few reports [50,127,177]. In particular, ESI in an LC-tandem MS configuration that is widely used in detection and structural characterization of anthraquinone dyes from reference compounds, dyed samples and historical textiles [145,152,[178][179][180].…”

Section: Fluorescence Detectionmentioning

confidence: 99%

“…ESI is the most important soft ionization technique in the analysis of anthraquinone dyes due to their polar nature [32,51,141,147,151,[177][178][179][180][181], though APCI has also been used in few reports [50,127,177]. In particular, ESI in an LC-tandem MS configuration that is widely used in detection and structural characterization of anthraquinone dyes from reference compounds, dyed samples and historical textiles [145,152,[178][179][180]. Anthraquinone detection has been reported in both positive and negative ion modes, however negative ion mode is reported to be more sensitive and typically preferred [54,151].…”

Section: Fluorescence Detectionmentioning

confidence: 99%

Analytical methods for determination of anthraquinone dyes in historical textiles: A review

Shahid

Wertz

Degano

et al. 2019

Analytica Chimica Acta

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Historical and archaeological textiles are among the most crucial and vulnerable records of our social and cultural history. Analysis of organic colorants found in these materials is unquestionably one of the most powerful tools to understand historical developments, cultural exchanges, and progress in science and technology. Natural anthraquinones represent the most commonly used natural colorants for textile dyeing until the late 19 th century. The identification of anthraquinones in cultural heritage objects is a challenging task due to the small size of historical samples, diversity of potential dye sources, variable extraction procedures and dyeing methods, complex chemical constitution, structurally analogous chromophores, and possible presence of degradation products and contaminants. Developments in dye analysis of historical interest have originated and expanded along with the general advances in analytical science. In the last few decades, a close cooperation between science and cultural heritage disciplines contributed enormously to this field. The topic of historical dyes and their analysis in textiles, artworks, archaeological objects and cultural heritage materials has been reviewed several times in the last fifteen years. However, no review has been published to-date exclusively on the analysis of anthraquinone colorants in historical and archaeological textiles. Overall, liquid chromatography (LC)-based techniques have been the most widely used method for anthraquinone dye analysis. Owing to increasing demand of minimally invasive/non-invasive techniques, recent developments of novel techniques have resulted in the availability of many alternative/complementary methods to LC-based analysis. This review begins with a short overview of sources, chemistry and importance of natural anthraquinone dyes found in historical textiles before turning to a detailed discussion on developments involving established and emerging analytical techniques of anthraquinone dye analysis for textile cultural heritage materials. To illustrate the state-of-the-art, representative examples of analytical techniques highlighting their advantages, limitations and applicability are also presented.

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Identification of orcein and selected natural dyes in 14th and 15th century liturgical paraments with high-performance liquid chromatography coupled to the electrospray ionization tandem mass spectrometry (HPLC-ESI/MS/MS)

Cited by 31 publications

References 43 publications

A Mass Spectrometry-Based Approach for Characterization of Red, Blue, and Purple Natural Dyes

A Mass Spectrometry-Based Approach for Characterization of Red, Blue, and Purple Natural Dyes

Characterizations of palace lantern tassels preserved in The Palace Museum, Beijing, by UPLC‐ESI‐Q‐TOF

Analytical methods for determination of anthraquinone dyes in historical textiles: A review

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