Theoretical studies of structure, energetics and properties of Ca2+ complexes with alizarin glucoside

Toczek, D.; Kubas, Karolina; Turek, Michał; Roszak, Szczepan; Gancarz, Roman

doi:10.1007/s00894-013-1841-9

Cited by 5 publications

(3 citation statements)

References 33 publications

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“…The calculation of these spectra for well-defined chemical compositions can provide this understanding, enhancing the ability to interpret difficult experimental spectra obtained from natural mixed systems. Indeed, several dispersion-corrected DFT studies have been performed on calcium oxalate whereby the IR and Raman vibrational spectra were successfully predicted for the three different polyhydrates of calcium oxalate [12,[43][44][45][46][47].…”

Section: Characterization Of Calcium Oxalatesmentioning

confidence: 99%

Opportunities given by density functional theory in pathological calcifications

Tielens¹,

Vekeman²,

Bazin³

et al. 2022

Comptes Rendus. Chimie

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Density Functional Theory has made the study of biomaterials feasible in the past years leading to better understanding of causes and possible treatments of related pathologies. Although it has been successfully applied in many fields, it has not yet consistently found its way into the field of pathological calcifications. An overview will be given of the studies where this technique has been applied in order to outline the important contributions that it can bring in the field of biomineralization. More specifically, studies on DFT calcifications from calcium oxalates and calcium phosphates, with relevance to bone formation and kidney stones, will be reviewed. Finally, a short outlook on silica mineralization will be presented as well.

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Section: Characterization Of Calcium Oxalatesmentioning

confidence: 99%

Opportunities given by density functional theory in pathological calcifications

Tielens¹,

Vekeman²,

Bazin³

et al. 2022

Comptes Rendus. Chimie

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“…This method requires only addition of lithium acetate to the analyte solution. It is well-known that carbohydrates have a high affinity for metal cations, − and hexoses are no exception. For this reason, the protonated species [M+H] + is usually not observed in an ESI mass spectrum, and instead [M+Na] + is formed with ambient sodium.…”

mentioning

confidence: 99%

Distinguishing Biologically Relevant Hexoses by Water Adduction to the Lithium-Cationized Molecule

et al. 2017

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A method to distinguish the four most common biologically relevant underivatized hexoses, d-glucose, d-galactose, d-mannose, and d-fructose, using only mass spectrometry with no prior separation/derivatization step has been developed. Electrospray of a solution containing hexose and a lithium salt generates [Hexose+Li]. The lithium-cationized hexoses adduct water in a quadrupole ion trap. The rate of this water adduction reaction can be used to distinguish the four hexoses. Additionally, for each hexose, multiple lithiation sites are possible, allowing for multiple structures of [Hexose+Li]. Electrospray produces at least one structure that reacts with water and at least one that does not. The ratio of unreactive lithium-cationized hexose to total lithium-cationized hexose is unique for the four hexoses studied, providing a second method for distinguishing the isomers. Use of the water adduction reaction rate or the unreactive ratio provides two separate methods for confidently (p ≤ 0.02) distinguishing the most common biologically relevant hexoses using only femtomoles of hexose. Additionally, binary mixtures of glucose and fructose were studied. A calibration curve was created by measuring the reaction rate of various samples with different ratios of fructose and glucose. The calibration curve was used to accurately measure the percentage of fructose in three samples of high fructose corn syrup (<4% error).

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“…Much of the research on metal complexes with dyes has been carried out with the aglycons alizarin and purpurin; however, it is also important to consider the coordination mechanisms of the glycosides in madder root as saccharide moieties possess many –OH functions able to act as electron donors to metals, hence it is likely that they are involved in complexation. Some theoretical work has been done on the coordination of alizarin glycoside with Ca 2+ , which suggests that glycosylation increases binding affinity to the metal . Stereochemistry is important in the ability of a saccharide moiety to coordinate to a metal ion; the sugar must have three adjacent hydroxyl groups in axial‐equatorial‐axial positions in chair form , and the terminal xylose and glucose of the primeveroside‐group present in both lucidin primeveroside and ruberythric acid have the ability to coordinate in this way.…”

Section: Metal Complexes Formed In Mordant Dyeing With Maddermentioning

confidence: 99%

Natural dyes in madder (Rubiaspp.) and their extraction and analysis in historical textiles

Blackburn

2017

Coloration Technology

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Textiles coloration using extracts from the roots of various madder species (Rubia spp.) has been performed for centuries. To date, 68 anthraquinone colorants have been detected in Rubia spp. used to dye textiles. Many of these dyes are sensitive to hydrolysis and degradation from enzymes, extraction chemicals and processing temperatures, and are often overlooked as colorants in historical textiles. Conclusions in literature of the past 30 years concerning colorants present in planta and, particularly, in madder‐dyed artefacts are being challenged as new analysis methods are developed. The recent advent of ‘soft’ extraction techniques has demonstrated that anthraquinone glycosides and other sensitive molecules, such as carboxylated compounds, need to be preserved; this valuable chemical information embedded in the dye structure may be lost if extraction and analysis is too harsh. Some compounds thought to be present in madder and madder‐dyed artefacts are in fact degradation products resultant from the extraction process, and degradation pathways have been developed to better understand the reactivity and stability of these compounds. Detailed analysis of dyes in textile artefacts can reveal important cultural and heritage information concerning historical textiles relative to the specific dye species, the area of the world where this may have grown, how and where it was dyed, and, perhaps, where it was traded. Understanding the precise molecular structure of these dyes and their chemical reactivity is important to provide knowledge of their interactions with physical substrates, such as textile fibres, which could be used to develop superior techniques for analysis of artefacts.

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Theoretical studies of structure, energetics and properties of Ca2+ complexes with alizarin glucoside

Cited by 5 publications

References 33 publications

Opportunities given by density functional theory in pathological calcifications

Opportunities given by density functional theory in pathological calcifications

Distinguishing Biologically Relevant Hexoses by Water Adduction to the Lithium-Cationized Molecule

Natural dyes in madder (Rubiaspp.) and their extraction and analysis in historical textiles

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