Inhibition of human cytochrome CYP1B1 by anthraquinone compounds,chrysophanol and physcion

The in vitro inhibitory effects of chrysophanol and physcion on CYP1B1 were explored,utilizing ethoxyresorufin as the substrate.The inhibition kinetics of CYP1B1 by these compounds were assessed with escalating doses of ethoxyresorufin.Both chrysophanol(IC_(50)(0.47±0.01)μmol·L^(-1))and physcion(IC_(50)(0.35±0.02)μmol·L^(-1))significantly reduce the catalytic efficiency of CYP1B1.The V_(max)and K_(m)values are determined to be(51.9912±10.0547)pmol·μg^(-1)(protein)·min^(-1) and(0.9663±0.2987)nmol·L^(-1)for chrysophanol,and(45.4227±1.9978)pmol·μg^(-1)(protein)·min^(-1) and(0.4367±0.0386)nmol·L^(-1)for physcion,respectively.Kinetic analysis reveals that chrysophanol and physcion exert mixed inhibitory effects on CYP1B1.This mixed inhibition is primarily characterized by the compounds’ability to competitively bind to the active sites of CYP1B1,as well as potentially through non-competitive mechanisms,thereby reducing the enzyme’s catalytic efficiency.Molecular docking studies are conducted to elucidate the interaction between anthraquinone derivatives and CYP1B1,indicating that these compounds may inhibit CYP1B1 activity by binding to their active sites.The demonstrated capacity of chrysophanol and physcion to inhibit CYP1B1 enzymatic function unveils a potential anticancer mechanism,advancing our comprehension of how the structure of anthraquinone derivatives correlates with CYP1B1 inhibition and paving the way for developing innovative cancer treatments.

Three Anthraquinones Isolated from Aster tataricus L.f

The roots and rhizomes of Aster tataricus L. f (Zi-wan) is a traditionalChinese medicine, which has been used for relieving cough and resolving phlegm. Previousinvestigation of the species resulted in the isolation and identification of triterpenes,triterpenoid saponins, cyclic pentapeptides, and oligopeptides. We have also reported thepolyphenols and a dipeptide isolated from the species. In this paper, the isolation and structureelucidation of three anthraquinones, chrysophanol (1), physciori (2), and emodin (3), are described.Chrysophanol and physcion were isolated from family Composi-tae for the first time.

The Action of Aloe Anthraquinones in Protecting the Growth of Soybean from Ultraviolet Radiation Stress

In order to investigate the protective effect of aloe anthraquinones on growth and development of soybean against ultraviolet B radiation stress from the morphological structure and physio-chemical indices. The results showed that, stressed by the enhanced ultraviolet b radiation, the soybean gave a dwarfed plant, shrunken leaf area and decreased photosynthetic pigment, while an ascended MDA content. Spraying aloe anthraquinones effectively relieved the reductions of chloro- phyll content and biomass and decreased the production of MDA under the radia- tion of UV-B. Moreover, under the UV-B radiation, waxy substances on epidermal cells increased remarkably and the stomas showed obvious subsidence, while spraying aloe anthraquinones could maintain the structure and shape of cells similar to that under natural light, and the stomas subsidence as well.

Organ specific differences in alteration of aquaporin expression in rats treated with sennoside A,senna anthraquinones and rhubarb anthraquinones

OBJECTIVE Senna and rhubarb are classified as stimulative laxatives,and known to have similar effective constituents,the anthraquinones.Being protected by theβ-glucoside bond,the anthraquinones can reach the intestines where they are degraded into complex metabolites by enzymes secreted from the intestinal microbiome.It is these complex metabolites that produce the laxative effects.Then the similarities and differences of action between the anthraquinones require further elucidation.METHODS Here,we studied metabolites of senna anthraquinones(SAQ),rhubarb anthraquinones(RAQ)and their chemical marker,sennoside A(SA),in a rat diarrhea model.In the in vitro biotransformation experiments,SAQ,RAQ and SA were incubated with rat fecal flora solution and the metabolites produced were analyzed using HPLC.In the in vivo studies,the same compounds were investigated for purgation induction,with measurement of histopathology and multiple aquaporins(Aqps)gene expression in six organs.RESULTS SAQ and RAQ had similar principal constituents but could be degraded into different metabolites.A similar profile of Aqps down-regulation for all compounds was seen in the colon,suggesting a similar mechanism of action for purgation.However,in the kidneys and livers of the diarrhea-rats,down-regulation of Aqps was found in the RAQ-rats whereas up-regulation of Aqps was seen in the SAQ-rats.Furthermore,the RAQ-rats showed lower aquaporin 2(Aqp2)protein expression in the kidneys,whilst the SA-rats and SAQ-rats had higher Aqp2 protein expression in the kidneys.This may have implications for side effects of SAQ or RAQ in patients with chronic kidney or liver diseases.CONCLUSION SAQ and RAQ showed similar laxative actions with a similar mechanism,they could display different actions in rat kidneys and livers.We suggest that the clinical usage of senna or rhubarb products should be clarified for patients having chronic kidney or liver diseases.

Determination of Total Anthraquinone and Free Anthraquinone in Different Processed Products of Rhubarb

[Objectives]The content of total anthraquinone and 5 free anthraquinones in different processed products of rhubarb were determined.[Methods]Using emodin as the reference,the concentration of 1%magnesium acetate methanol solution was used for color development,and the absorbance was measured at 516 nm wavelength;the mobile phase was methanol-0.1%phosphoric acid(76∶24)aqueous solution,the detection wavelength was set at 256 nm,the flow rate was 1.0 mL/min,the column temperature was 30℃,and the sample size was 10μL.[Results]The content of total anthraquinones in rhubarb was determined by UV spectrophotometry.The linear range was 0.98-23.52μg/mL,R2=0.9993,the average recoveries were 100.12%,99.66%and 99.15%,with RSDs of 1.58%,0.94%and 1.41%,respectively.The linear ranges of emodin,emodin,emodin,chrysophanol and emodin methyl ether were 0.0207-0.414(R2=0.9999),0.1721-3.442(R2=0.9996),0.0203-0.406(R2=0.9999),0.148-2.96(R2=0.9998)and 0.164-3.28(R2=0.9993),respectively.[Conclusions]The contents of total anthraquinones and free anthraquinones in different processed products of rhubarb were determined by UV spectrophotometry and HPLC.The method can be used for quality control of rhubarb and its different processed products.

Three New Anthraquinones from Polygonum cillinerve

Three new anthraquinones, emodin-8-β-D-（2＂-O-coumarate）glucoside 1, emodin-8-β-D-（6＇-O-acetyl）glucoside 2 and physicon-8-β-D-（6＇-O-acetyl）glucoside 3, were isolated from the roots of Polygonum cillinerve and their structures were established by spectroscopic methods. The biological activity indicated that compound 1 had the scavenging activity on 1,1-diphenyl-2-picrylhydrazyl （DPPH） radicals （the IC50 = 8.5 μmol/L）, and compound 1-3 showed no activities against HL-60 and BCJC-823 cells by MTT method in vitro.

Determination of anthraquinone prodrug and its hydrolytically active compounds using RP-HPLC

In order to study the hydrolytic characterization of an anti-inflammatory prodrug （ RI-1 ） in vitro, an effective, accurate and reliable method for the simultaneous determination of the prodrug and its two hydrolytic active compounds is developed using reverse phase high-performance liquid chromatography （RP-HPLC）. The chromatographic separation is performed on an ODS-2 C18 column （250 mm × 4. 6 mm, 5.0 μm particle size） with a simple elution program. The mobile phase is V（ methanol） ： V（0. 1% phosphoric acid solution） =90：10 （adjust pH to 2. 3）. A wavelength of 225 nm and a mobile phase flow rate of 1.0 mL/min are utilized for the quantitative analysis. Excellent linear behaviors over the investigated concentration ranges are observed with values of R2 higher than 0. 999 for all the analytes. The validated method is successfully applied to the simultaneous determination of the prodrug and its active components can be used to detect hydrolytic characterization in vitro.

A new anthraquinone glycoside from seeds of Cassia obtusifolia

A new anthraquinone glycoside 1, along with a known anthraquinone glycoside aurantio-obmsin-6-O-β-D-glucopyranoside 2, were isolated from the seeds of Cassia obtusifolia. On the basis of spectral and chemical evidences, the structure of 1 was established as 1-demethylaurantio-obtusin-2-O-β-D-glucopyranoside. Moreover, the 13C NMR of 2 was assigned totally and correctly for the first time based on the two-dimensional NMR.

New anthraquinone derivatives from the roots of Berchemia floribunda

A new naphthoquinone-anthraquinone dimer named floribundiquinone E （1） and a new anthraquinone 2-acetylphyscion （2） were isolated from the roots of Berchemia floribunda Brongn. Their structures were elucidated on the basis of spectroscopic methods.

Treatment of anthraquinone dye wastewater by hydrolytic acidification-aerobic process

Experiment on microbial degradation with two kinds of biological process, hydrolytic acidification-aerobic process and aerobic process was conducted to treat the anthraquinone dye wastewater with COD Cr concentration of 400 mg/L and chroma 800. The experimental result demonstrated that the hydrolytic-aerobic process could raise the biodegradability of anthraquinone dye wastewater effectively. The effluent COD Cr can reach 120170 mg/L and chroma 150 which is superior to that from simple aerobic process.

Simultaneous determination of flavonoids and anthraquinones in chrysanthemum by capillary electrophoresis with amperometry detection

A high-performance capillary electrophoresis with amperometry detection method （CE-AD） has been developed for the analysis of flavonoids and anthraquinones （emodin, kaempferol, apigenin, luteolin and rhein） in chrysanthemum. Under optimum conditions, these five analytes were base-line separated within 17 min using a borate-phosphate running buffer （1.5 ×10^-2 mol/L borate-3× 10^-2 mol/L phosphate running buffer, pH 9.0） at a working potential of ＋0.90 V （vs. SCE） and a separation voltage of 19 kV. The linear relationship between concentration and current response was obtained with detection limits （S/N = 3） ranging from 1.0 × 10^-7 to 2.1 × 10^-7 g/mL for all analytes. This proposed method was successfully used in the analysis of four kinds of chrysanthemum with relatively simple extraction procedures, the assay results were satisfactory.

Improving extraction yield of humic substances from lignite with anthraquinone in alkaline solution

Based on the characteristics of the lignite sample, effects of assistant anthraquinone （AQ） on extraction yield of humic substances （HS） and the action mechanisms of AQ in alkaline condition were studied by Fouvier transform infrared （FT-IR） spectroscopy. The results indicate that assistant AQ can not only increase the extraction yield of HS but also reduce the alkali dosage （NaOH） as well as the extraction temperature and extraction time. Under the optimal conditions of alkali dosage of 9%, AQ dosage of 0.75%, extraction temperature of 80 ℃, extraction time of 30 min, stirring speed of 600 r/min and solid-to-liquid ratio of 1：3, the extraction yield of HS reaches 80.08%, which is increased by more than 20% compared with the conventional extraction. FT-IR spectra show that AQ is able to prevent dissolved HS from being destroyed into undissolved substance by alkali and 1-IS obtained in the presence of AQ possesses more groups of COOR and --COOH than that obtained without AQ.

Effects of Cerium Dopant on Ni-B Amorphous Alloy Catalysts Used in 2-Ethylanthraquinone Hydrogenation

A series of Ce-doped Ni-B amorphous alloy catalysts were prepared by a KBH_4 reduction method, characterized by ICP, BET, XRD, H_2-chemisorption, H_2-TPD, etc., and tested in the hydrogenation of 2-ethylanthraquinone. The results of characterization show that with the addition of Ce the amount of H_2-chemisorption and H_2-TPD areas first increases markedly and then decreases with the maximum appears at the atomic ratio of Ce to Ni of 0.036. The hydrogenation activity also shows the same trend. The effects of Ce are attributed to its dispersion of Ni particles, resulting in the formation of more surface Ni centers. However, much higher Ce contents may result in the decrease of the surface Ni contents. After heat treatment at higher temperatures, the amorphous structure of Ni-B is destroyed.

Electrooxidative Degradation of an Anthraquinone Dye with in-situ Electrogenerated Active Chlorine in a Divided Flow Cell

The purpose of this paper was to investigate the possibility of treating C. I. Reactive Blue 19 wastewater by electrochemical oxidation via electrogenerated active chlorine, using metallic oxide coatings （dimensional stable anode, DSA） as anode. The electrolysis for the simulated wastewater was conducted at a constant current. Absorbances at 592 nm and 255 nm were measured to follow the decolorization of the dye and the degradatin of its aromatic ring. After 4 h of electrolysis under the experimental conditions： current density of 15 A·m^-2, 0.2 mol·L^-1 NaCl, 0.1 mol·L^-1 Na2SO4, 0.1 mmol·L^-1 dye, initial pH=6.4 and T=30℃, 100% decolorization of the dye and about 45% degradation of its aromatic ring were achieved, while no obvious change of total organic carbon was observed. The experimental results suggest that the decolorization of the dye and degradation of its aromatic ring were directly affected by current density, temperature, concentrations of the dye and sodium chloride, while slightly affected by initial pH and sodium sulfate concentration; the decolorization of the dye and degradation of its aromatic ring followed pseudo-first-order kinetics; and indirect electrooxidation, using electrogenerated active chlorine, predominated in the electrochemical oxidation.

Decolorization of Anthraquinone dye by Rhodopseudomonas XL-1

Rhodopseudomonas XL 1 gained from textile wastewater can effectively decolorize anthraquinone dye. Under anaerobic condition, 93 percent of the anthraquinone dye is decolorized , which is higher than that under aerobic condition. The optimum pH is 6～9 and the optimum temperature is 20～40℃ for the anthraquinone dye decolorization by XL 1 . XL 1 can not decolorize the anthraquinone dye when it is the sole carbon source. Microbial cometabolism and decolorization of the dye take place in the presence of some other carbon source(0.2～0.4g/100ml)called cometabolic substrate. The cometabolic substrate can be peptone, glucose, sodium acetate, beef extract, amylum, etc. The change of molecular structure of the dye before and after decolorized by XL 1 is studied by UV Vis absorption spectrum. The results indicate that its molecular structure is changed evidently.

Anti-inflammatory Effects and Mechanisms of Rhein, an Anthraquinone Compound, and Its Applications in Treating Arthritis: A Review

Inflammation is a defensive response of living tissues to damaging agents,which exists in two forms,acute inflammation and chronic inflammation,and chronic inflammation is closely related to arthritis.Currently,the commonly prescribed anti-inflammatory medications are greatly limited by high incidence of gastrointestinal erosions in the clinical applications.Rhein,a bioactive constituent of anthraquinone,exhibits excellent anti-inflammatory activities and therapeutic effects on arthritis with less gastrointestinal damages.Although there are numbers of studies on anti-inflammatory effects and mechanisms of rhein in the last few decades,to the best of our knowledge,only a few review articles pay attention to the interactive relationships of rhein on multiple inflammatory signaling pathways and cellular processes from a comprehensive perspective.Herein,we summarized anti-inflammatory effects and mechanisms of rhein and its practical applications in the treatment of arthritis,thereby providing a reference for its basic researches and clinical applications.

Antitumor and Antioxidant Activities of the New Anthraquinone Derivatives: Synthesis, DPPH, ABTS, Biological and DFT Investigations

In the given research,for the first time the molecular structures of four new anthraquinone derivatives have been predicted and investigated by using Density Functional Theory(DFT/M052X/MidiX)in water.After quantum-chemical calculations the title compounds have been synthesized.The M052X/MidiX method has been employed to obtain Bond Dissociation Enthalpy(BDE),Mulliken Charges,NBO analysis,Ionization Potential(IP),Electron Affinities(EA),HOMO and LUMO energies,Hardness(η),Softness(S),Electronegativity(μ),Electrophilic Index(ω),Electron Donating Power(ω^-),Electron Accepting Power(ω^+)and Energy Gap(Eg) in order to infer scavenging activity of the four new synthesized anthraquinone derivatives(Sm-3,Sm-4,Sm-7,Sm-10).Comparative analysis of BDE of Sm-3,4,7,10 indicates the weal antioxidant potential of these structures.These molecules have high antioxidant potential due to the planarity and formation of intramolecular hydrogen bonds.Experimental investigations establish high antioxidant and antitumor activities of the synthesized anthraquinone derivatives.

Anthraquinone derivative as high-performance anode material for sodium-ion batteries using ether-based electrolytes

Organic materials, especially the carbonyl compounds, are promising anode materials for room temperature sodium-ion batteries owing to their high reversible capacity, structural diversity as well as eco-friendly synthesis from bio-mass. Herein, we report a novel anthraquinone derivative, C_(14)H_6 O_4 Na_2 composited with carbon nanotube(C_(14)H_6 O_4 Na_2-CNT), used as an anode material for sodium-ion batteries in etherbased electrolyte. The C_(14)H_6 O_4 Na_2-CNT electrode delivers a reversible capacity of 173 mAh g^(-1) and an ultra-high initial Coulombic efficiency of 98% at the rate of 0.1 C. The capacity retention is 82% after 50 cycles at 0.2 C and a good rate capability is displayed at 2 C.Furthermore, the average Na insertion voltage of 1.27 V vs. Na^+/Na makes it a unique and safety battery material, which would avoid Na plating and formation of solid electrolyte interface. Our contribution provides new insights for designing developed organic anode materials with high initial Coulombic efficiency and improved safety capability for sodium-ion batteries.

2-Ethyl-9,10-anthraquinone assisted sol–gel synthesis of Pd/γ-Al2O3 nanorods with enhanced catalytic performance in 2-ethyl-9,10-anthraquinone hydrogenation

A series of nanorod-like porous Pd/γ-Al2 O3 catalysts with controllable textural properties and enhanced catalytic performance in 2-ethyl-9,10-anthraquinone(eAQ) hydrogenation for H2 O2 preparation were successfully prepared via a facile sol-gel method using aluminum isopropoxide as aluminum precursor and eAQ as structure directing agent,sequential calcination and impregnation process with Na2 PdCl4 solution.The physicochemical properties of the catalysts obtained with different addition amounts of eAQ.were comparatively characterized by XRD,TG-DSC,BET,TEM,CO-TPR,H2-TPR and H2-O2 titration.The results show that addition of eAQ can not only effectively control the textural properties(surface area,pore volume and average pore size) of the catalysts,but also lower their reduction temperature of active metal.Importantly,the catalyst obtained with an addition amount of 4 wt% eAQ shows the highest hydrogenation efficiency of 10.28 g·L^-1,which is 37.3% higher than 7.49 g·L^-1 of the catalyst obtained without eAQ.

Hydrogenation of Alkylanthraquinone Over Pore-Expanded and Channel-Shortened Pd/SBA-15

SBA-15 silica was synthesized by adding normal paraffin and alkyl benzene as swelling agents and using a low-temperature gelation procedure.Pd was then impregnated on SBA-15,yielding a catalyst.Characterizations of the catalyst by X-ray diffraction,N2 adsorption/desorption,scanning electron microscopy,transmission electron micrographs,X-ray photoelectron spectroscopy,in situ FTIR,and a hydrogenation test of 2-ethyl-anthraquinone reveal that the addition of C6-C9 normal paraffin and 1,3,5-triisopropylbenzene could enlarge the pore diameter without a significant loss of ordered structure.Moreover,the length of SBA-15 pore channels decreased significantly.However,the sizes of Pd particles increase as the pore diameter is enlarged.The largest pore size(13.6 nm)and short length of pore channels(ca.0.35μm)are achieved by adding n-hexane.As a result,this catalyst exhibits the highest hydrogenation activity with an approximately 100%improvement,compared with a conventionally synthesized catalyst in the absence of a swelling agent.