The 2,2 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS •+ ) radical cation-based assays are among the most abundant antioxidant capacity assays, together with the 2,2-diphenyl-1picrylhydrazyl (DPPH) radical-based assays according to the Scopus citation rates. The main objective of this review was to elucidate the reaction pathways that underlie the ABTS/potassium persulfate decolorization assay of antioxidant capacity. Comparative analysis of the literature data showed that there are two principal reaction pathways. Some antioxidants, at least of phenolic nature, can form coupling adducts with ABTS •+ , whereas others can undergo oxidation without coupling, thus the coupling is a specific reaction for certain antioxidants. These coupling adducts can undergo further oxidative degradation, leading to hydrazindyilidene-like and/or imine-like adducts with 3-ethyl-2-oxo-1,3-benzothiazoline-6-sulfonate and 3-ethyl-2-imino-1,3-benzothiazoline-6-sulfonate as marker compounds, respectively. The extent to which the coupling reaction contributes to the total antioxidant capacity, as well as the specificity and relevance of oxidation products, requires further in-depth elucidation. Undoubtedly, there are questions as to the overall application of this assay and this review adds to them, as specific reactions such as coupling might bias a comparison between antioxidants. Nevertheless, ABTS-based assays can still be recommended with certain reservations, particularly for tracking changes in the same antioxidant system during storage and processing.
This report explores the antioxidant interaction of combinations of flavonoid–glutathione with different ratios. Two different 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical (ABTS•+)-based approaches were applied for the elucidation of the antioxidant capacity of the combinations. Despite using the same radical, the two approaches employ different free radical inflow systems: An instant, great excess of radicals in the end-point decolorization assay, and a steady inflow of radicals in the lag-time assay. As expected, the flavonoid–glutathione pairs showed contrasting results in these two approaches. All the examined combinations showed additive or light subadditive antioxidant capacity effects in the decolorization assay. This effect showed slight dilution dependence and did not change when the initial ABTS•+ concentration was two times as high or low. However, in the lag-time assay, different types of interaction were detected, from subadditivity to considerable synergy. Taxifolin–glutathione combinations demonstrated the greatest synergy, at up to 112%; quercetin and rutin, in combination with glutathione, revealed moderate synergy in the 30–70% range; while morin–glutathione appeared to be additive or subadditive. In general, this study demonstrated that, on the one hand, the effect of flavonoid–glutathione combinations depends both on the flavonoid structure and molar ratio; on the other hand, the manifestation of the synergy of the combination strongly depends on the mode of inflow of the free radicals.
Taxifolin, also known as dihydroquercetin, is the major flavonoid in larch wood. It is well known as an antioxidant and a bioactive substance. Taxifolin as an active pharmaceutical ingredient is produced industrially in crystalline form during the processing of larch wood. Some information is available on nano-and microstructured particles of taxifolin. This paper reports on the generation of a new form of taxifolin as microtubes. These self-assembled tubes were obtained from raw taxifolin by crystal engineering with urea at ambient temperature and pressure. The parameters of temperature, pH value, molar ratio of taxifolin and urea, and time duration were optimized for yield enhancement of the microtubes. The water solubility and melting point of the new form of taxifolin were established. The microtubes were characterized by X-ray diffraction, X-ray powder diffraction, microscopy, mass spectrometry, 1 H NMR spectroscopy, UV spectroscopy and Fourier transform infrared spectroscopy methods. The experimental results demonstrate that the microtubes and raw taxifolin both exist in crystalline form with the same structure of the crystal unit. However, they are characterized by different morphological and physicochemical properties. Computer simulation was performed to explain the mechanism of the selfassembly process. research papers Acta Cryst. (2019). B75, 175-182 Roman P. Terekhov et al. Taxifolin tubes: crystal engineering and characteristics 181 Figure 6 Molecular surface of taxifolin nanoparticle model: (a) nanoparticle surface and (b) cross-sectional view.
Computer modeling is a method that is widely used in scientific investigations to predict the biological activity, toxicity, pharmacokinetics, and synthesis strategy of compounds based on the structure of the molecule. This work is a systematic review of articles performed in accordance with the recommendations of PRISMA and contains information on computer modeling of the interaction of classical flavonoids with different biological targets. The review of used computational approaches is presented. Furthermore, the affinities of flavonoids to different targets that are associated with the infection, cardiovascular, and oncological diseases are discussed. Additionally, the methodology of bias risks in molecular docking research based on principles of evidentiary medicine was suggested and discussed. Based on this data, the most active groups of flavonoids and lead compounds for different targets were determined. It was concluded that flavonoids are a promising object for drug development and further research of pharmacology by in vitro, ex vivo, and in vivo models is required.
A large amount of the current literature dedicated to solid states of active pharmaceutical ingredients (APIs) pays special attention to polymorphism of flavonoids. Taxifolin (also known as dihydroquercetin) is an example of a typical flavonoid. Some new forms of taxifolin have been reported previously, however it is still unclear whether they represent polymorphic modifications. In this paper, we tried to answer the question about the taxifolin polymorphism. Taxifolin microtubes and taxifolin microspheres were synthesized from raw taxifolin API using several methods of crystal engineering. All forms were described with the help of spectral methods, scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), and thermal analysis (TA). SEM reveals that the morphology of the solid phase is very specific for each sample. Although XRPD patterns of raw taxifolin and microtubes look similar, their TA profiles differ significantly. At the same time, raw taxifolin and microspheres have nearly identical thermograms, while XRPD shows that the former is a crystalline and the latter is an amorphous substance. Only the use of complex analyses allowed us to put the puzzle together and to confirm the polymorphism of taxifolin. This article demonstrates that taxifolin microtubes are a pseudopolymorphic modification of raw taxifolin.
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