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Hairy root culture of plants is a considerable way for the in vitro production of valuable metabolites because of genetic stability, rapid growth rate, biochemical stability, and high capacity in the synthesis of secondary metabolites. Alizarin is an anthraquinone derived from the roots of madder (Rubia tinctorum) and has been used since ancient times as a natural red dye and exhibits various pharmacological and biological activities including anticancer, antioxidant, and anti-microbial activity. The influence of two factors including explant (leaf, internode, cotyledon) and strains of A. rhizogenes (15834, 2656, MSU, R1000) was tested on hairy root production of madder. All explants produced hairy roots with acceptable frequencies but leaf explants produced the highest number of roots per explant followed by cotyledons. The highest root induction rate (100%) and the highest number of hairy roots per explant were obtained from leaf explants inoculated with 15834 and R 1000. Analysis of the PCR products showed the presence of a 403 bp amplicon related to the specific reproduction of rolA gene in transgenic roots. Anthraquinone production was documented in transgenic roots but there was a significant difference between roots from different bacterial strains. As a brief result, the use of suitable bacterial strains and explants were effective factors for hairy root induction in madder. [ABSTRACT FROM AUTHOR]

High Performance Liquid Chromatography coupled to a Diode-Array-Detector (HPLC-DAD) is used to investigate samples which were extracted from ancient Egyptian textiles (4th–5th c. AD) of the Museum of Faculty of Archaeology, Cairo University. Madder is identified in several samples. According to semi-quantitative results, which are obtained from HPLC peak areas measured at 254 nm, madder that is rich in purpurin and poor in alizarin is identified in samples which were treated (i) only with madder and (ii) with madder and either indigo/woad (Indigofera species and other/Isatis tinctoria L.) or weld (Reseda luteola L.). The madder dye used in these samples could have been originated from Rubia peregrina L. However, the possible use of Rubia tinctorum L. (or other plants of the Rubiaceae family) by the Egyptian dyers cannot be ruled out, particularly if methods were developed by the ancient dyers to affect and control the relative composition of madder dye. The HPLC peak area ratio of alizarin versus purpurin is very high (>2.2) for samples which were treated with madder (probably originated from R. tinctorum) and a tannin source. Finally, in some samples, only indigoid dyes (indigo/woad) are identified. [ABSTRACT FROM AUTHOR]

The long history of madder as a source of red dyes and pigments is presented. The variety of plant sources and the range of anthraquinone components discovered over a long period are addressed. Topics such as analysis, industrial uses, biological staining, red bone staining in live animals and toxicity are outlined briefly. The contributions of many chemists are acknowledged. [ABSTRACT FROM AUTHOR]

The Privilegium maius is one of the most famous and spectacular forgeries in medieval Europe. It is a set of charters made in the 14th century upon commitment by Duke Rudolf IV, a member of the Habsburg family, to elevate the rank and the prestige of his family. These five charters, now kept at the Österreichisches Staatsarchiv in Vienna, have been subjected to a thorough interdisciplinary study in order to shed light on its controversial story. The charters are composed of pergamenaceous documents bound to wax seals with coloured textile threads. The present contribution concerns the characterisation of the inks used for writing and of the dyes used to colour to the threads: Are they compatible with the presumed age of the charters? Though showing only a part of the whole story of the charters, dyes analysis could contribute in assessing their complex history from manufacturing to nowadays. The dyes were characterised with non-invasive in situ measurements by means of fibre optic (FORS) and with micro-invasive measurements by means of Surface Enhanced Raman Spectroscopy (SERS) and High-Performance Liquid Chromatography with Mass Spectrometry (HPLC-MS) analysis. The results showed that the threads of four of the charters (three dyed with madder, one with orchil) were apparently coloured at different dyeing stages, then re-dyed in the 19−20th century.

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Madder has been used as a textile dye and pigment in works of art since antiquity. Madder dyes from different botanical species are characterized by different series of anthraquinone derivatives. The occurrence of one or more of these compounds in various relative amounts may provide a useful indication of the plant species used to obtain the dye. In this work, surface-enhanced Raman spectroscopy (SERS) was applied to the analysis of textile fibers dyed with madder from two different botanical species, Oldenlandia umbellata L. and Rubia tinctorum L. The resulting SERS spectra were interpreted in light of the actual composition of the madder dyes as determined by high-performance liquid chromatography. Interestingly, the SERS spectra were found to exhibit very distinctive spectral features depending on the different anthraquinone derivatives present in the dyes. In particular, the SERS spectrumof O. umbellata L. was found to match the spectrum of alizarin, while the SERS spectrum of R. tinctorum L. was surprisingly dominated by signals due to the less studied anthraquinone compound pseudopurpurin. With this study, we demonstrate that SERS spectra may offer valuable information regarding the major coloring constituents present in different madder species. Moreover, our work shows that not only can SERS be used successfully to differentiate among closely related anthraquinone derivatives, but also that this technique is particularly suitable for the detection of pseudopurpurin, leading to the identification of this compound in a number of works of art. [ABSTRACT FROM AUTHOR]

Madder ( Rubia tinctorum L.) has been exploited as a dye throughout history. The roots of the plant are very rich in the highly coloured glycosidic compounds ruberythric acid and lucidin primeveroside, alongside the corresponding aglycons which can be readily formed by deglycosylation, particularly during extraction. Supported by 1 H and 13 C NMR data, the conclusive X-ray crystal structure of the natural dye ruberythric acid is presented for the first time. The solid state structure revealed extensive intermolecular hydrogen bonding interactions between the sugar moieties in the unit cell, but only intramolecular hydrogen bonding through the hydroxyquinone groups. There is also some additional π–π stacking from the anthraquinone moiety. [ABSTRACT FROM AUTHOR]

Highlights: [•] We extract and identify four compounds from Rubia tinctorum L. [•] Anthraquinone compounds identified are lucidin primeveroside, ruberythric acid, alizarin and lucidin-ω-ethyl ether. [•] We provide first known crystal structure of lucidin primeveroside. [•] We provide the first ever known crystal structure of an anthraquinone glycoside. [•] We demonstrate flaws in previous analysis of madder phytochemicals. [Copyright &y& Elsevier]

n important issue connected with conservation chemistry is how to improve the storage and exposure conditions in order to suppress the fading and degradation of dyes and other components of paintings. Although the oxygen-free exposure cassettes are commonly known in museums, there is still lack of information in the literature about the effect of anoxic conditions on the degradation of dyes. This study is an attempt to start a database formation on the dyes degradation. Five commercial dyes (indigo, dragon's blood, curcumin, madder, carminic acid) were submitted to accelerated ageing by exposure to intensive light in the visible range in both oxygen-free (anoxia) and -rich conditions. Degradation of the samples was investigated by several analytical techniques (attenuated total reflectance infrared spectroscopy, Raman spectroscopy, reflectance UV-Vis spectroscopy, X-ray fluorescence spectroscopy and optical microscopy). The conclusions are based on the estimators (derived from the determination of colour differences from Vis spectra and from the changes in FTIR and Raman vibrational bands intensity). According to them, only indigo, dragon's blood and curcumin show greater stability in anoxic conditions in comparison with oxygen-rich ones while madder, carminic acid undergo greater degradation. [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]

Abstract: A reverse phase liquid chromatography-photodiode array detection method is developed for the characterization of ancient samples of madder. In the past, modifications of the madder chemical composition were carried out by hydrolysing the plant dye precursors in order to increase its red power, the aim of this transformation being to concentrate the red colour of the matter. After extraction of madder dyes in a water-methanol mixture, different anthraquinonic compounds were identified through the chemical constituents present in a garancine sample and in the two madder species growing in the Mediterranean area: Rubia tinctorum and R. peregrina. These two species comprise alizarin, purpurin, lucidin, rubiadin and pseudopurpurin for aglycones and, lucidin primeveroside, ruberythric acid, galiosin and rubiadin primeveroside for heterosidic precursors. These compounds were identified through retention times and UV spectra in comparison with pure standards. Six ancient materials belonging to the collection of the Roure Museum in Avignon (France) and dating from the nineteenth century are characterized as hydrolysed madder (garancine), synthetic alizarin and R. tinctorum roots. A colorimetric study is performed to compare the colour of each sample according to its chemical composition. [Copyright &y& Elsevier]

Abstract: Natural anthraquinonoid dyes (alizarin and purpurin) were used as platform chemicals to synthesise sustainable alternatives to existing synthetic dyes by alkylation of hydroxy groups in the 1- and 2-positions. In comparison with the parent compounds, the derivatised dyes were insensitive to pH change, insoluble in alkali and the λmax for the mono-alkylated derivatives was unchanged and that of the bis-alkylated derivatives was reduced by 53–54 nm. Melting points decreased with derivatisation as the ability of the dyes to form inter-molecular interactions decreased. Dye exhaustion and colour strength values for dyeings on PET were relatively high for the parent and mono-alkylated derivatives and lower for the larger bis-alkylated derivatives. Mono-alkylation with methyl-4-butanoate groups improved the dyeing properties of the dyes on PLA. All dyeings displayed excellent wash fastness and the light fastness was improved in the case of the mono-alkylated derivatives owing to the removal of the photo-sensitive 2-hydroxy group. [ABSTRACT FROM AUTHOR]

A reversed phase HPLC method has been developed for the identification and quantification of madder applied to an old textile. An isocratic method was used for the identification of alizarin and purpurin, the main pigments in the madder plant, which were identified and quantified in cotton and wool reference samples and in the unknown textile. FTIR-spectroscopy was also used for the identification of pigment and fiber of the unknown sample. [ABSTRACT FROM AUTHOR]

The effect of two elicitor types prepared from three different fungi on the alizarin content and the ultrastructure of Rubia tinctorum cells was studied. The de novo alizarin synthesis took place predominantly during the first day of treatment then it was followed by a constant release of alizarin into the medium. The alkalinization of the medium was similar in every treatment. The number of the living cells did not changed during 24-h elicitor treatments, but it decreased significantly after 96 h. The appearance of vacuolar bodies, and the change of the plasmalemmasome structure from vesiculo-reticular to reticulo-lamellar were the most typical morphological syndromes due to elicitation. Phytium elicitor proved to be the least effective, and Botrytis elicitor seemed to be the most effective. [ABSTRACT FROM AUTHOR]

The Privilegium maius is one of the most famous and spectacular forgeries in medieval Europe. It is a set of charters made in the 14th century upon commitment by Duke Rudolf IV, a member of the Habsburg family, to elevate the rank and the prestige of his family. These five charters, now kept at the Österreichisches Staatsarchiv in Vienna, have been subjected to a thorough interdisciplinary study in order to shed light on its controversial story. The charters are composed of pergamenaceous documents bound to wax seals with coloured textile threads. The present contribution concerns the characterisation of the inks used for writing and of the dyes used to colour to the threads: Are they compatible with the presumed age of the charters? Though showing only a part of the whole story of the charters, dyes analysis could contribute in assessing their complex history from manufacturing to nowadays. The dyes were characterised with non-invasive in situ measurements by means of fibre optic (FORS) and with micro-invasive measurements by means of Surface Enhanced Raman Spectroscopy (SERS) and High-Performance Liquid Chromatography with Mass Spectrometry (HPLC-MS) analysis. The results showed that the threads of four of the charters (three dyed with madder, one with orchil) were apparently coloured at different dyeing stages, then re-dyed in the 19–20th century. [ABSTRACT FROM AUTHOR]