Series Of Anthraquinone Derivatives Research Articles

Surface‐enhanced Raman spectroscopy of various madder species on wool fibers: the role of pseudopurpurin in the interpretation of the spectra

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 spectrum of 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. Copyright © 2015 John Wiley & Sons, Ltd.

Statistical Analysis of Ionization Energy Correlations and of Integral Quantum Characteristics in the Series of Anthraquinone Derivatives

The classes of anthraquinone derivatives, containing OC6H4?(??3)3 and NC5H10 groups have been investigated. Quantum-chemical calculations with the help of semiempirical method PM3 and absorption spectra in the visible and UV-areas have been carried out. With the use of single factor regression and correlation analysis, the linear correlations between the vertical ionization potentials and the integral strength of the oscillator have been ascertained. This fact indicates strong electron correlation between the highest and the low electron levels of molecules. The errors for the ionization potentials have been calculated.

Covalent Chemical Modification of Single-walled Carbon Nanotubes Using Azide Functionalised Anthraquinone Derivatives for Pseudocapacitor Application.

ABSTRACTElectrodes made of single-walled carbon nanotubes (SWCNTs) chemically modified by a series of anthraquinone derivatives (AQ) have been prepared and characterized by cyclic voltammetry in 0.1M H2SO4, using the standard 3 electrode set-up and by Raman spectroscopy. It has been demonstrated that a AQ modified SWCNT electrode provided between 114 to 220% higher specific capacitance, compared to pristine SWCNT electrode, depending on the length of the spacer between SWCNT and AQ.

ChemInform Abstract: Novel Anthraquinone Derivatives with Redox-Active Functional Groups Capable of Producing Free Radicals by Metabolism: Are Free Radicals Essential for Cytotoxicity?

The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones.

Anti-angiogenic effects of rhubarb and its anthraquinone derivatives

Ethnopharmacological relevance Rhubarb root (Dahuang) is often included as an ingredient in traditional Chinese compound prescriptions for the treatment of inflammatory diseases. This application may possibly be mediated through anti-angiogensis and thus would shed light on its potential value in cancer therapy. Aim of the study To elucidate the anti-angiogenic properties of rhubarb root, we tested the inhibitory effects of different fractions and a series of anthraquinone derivatives against vessel formation in zebrafish embryos. Materials and methods The 95% ethanol extract and four subsequent fractions ( n-hexane, ethyl acetate, n-butanol and aqueous fractions) of rhubarb root and five anthraquinone derivatives were investigated on zebrafish model by quantitative endogenous alkaline phosphatase assay and staining assay. Results Ethyl acetate fraction showed the strongest inhibition of vessel formation by 52%. Three anthraquinones (aloe-emodin, emodin and rhein) displayed potent anti-angiogenic activities. Conclusions The angiogenic properties of rhubarb root may partly account for its use in inflammatory diseases. The anthraquinones with acidic or polar, hydrophilic substitution at C-6 or C-3 positions played a substantial role in inhibiting angiogenesis. The value of the zebrafish angiogenic model is further supported.

Thermodynamic properties of anthraquinone derivatives

The enthalpies of solution of a series of anthraquinone derivatives in dioxane at various dilutions were determined by isothermal calorimetry.

Isolation and Structure Elucidation of Anthraquinones from Barleria eranthemoides (Acanthaceae)

Barleria eranthemoides R. Br. (Acanthaceae) is used in traditional medicine in the Bunda district, Tanzania. Root decoctions or infusions of pounded leaves are drunk for treatment of dysentery and against infectious diseases. Whereas phytochemical and biological investigations on the 80% methanolic extract of roots of B. eranthemoides are still in progress, a series of anthraquinone derivatives have been obtained from the n-hexane extract, which was investigated for its antiprotozoal activity. In addition to barleriaquinone (1), reported before from Barleria buxifolia, and the other known anthraquinones chrysophanol (2), isochrysophanol (3), digitopurpone (4), and 2-methoxy-7-methylanthraquinone (5), a new unusual anthraquinone derivative containing an epoxide moiety (6) was obtained. Structures were elucidated by means of 1D (1H, 13C, DEPT) and 2D (COSY, HSQC and HMBC) NMR and mass spectroscopy.

Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?

The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones.