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.

Determination of Emodin and Chrysophanol Contents in Callus of Cassia tora L. Leaf

[ Objective] Through inductive culture, emodin and chrysophanol contents in cassia seed were increased. [ Method ] MS culture medium was used to bourgeon seedlings of cassia seed and to induce cotyledon callus of cassia seed while HPLC method was adopted to determine emodin and ehrysophanol eontents.[ Result] Emedin and chrysophanol contents in cotyledon callus were 0. 099% and 0. 312%, respectively, while they were 0.029% and 0. 190% respectively in cassia seed. [ Conclusion] The method of inducing cotyledon callus was helpful for increasing emodin coment in cassia seed.

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.

Advances in the production technology of hydrogen peroxide

This article mainly summarizes various aspects of hydrogen peroxide(H2O2)production through the anthraquinone route,including hydrogenation catalysts,working solution,regeneration technique,hydrogenation reactors,and environmental protection.The advances and breakthrough of SINOPEC in the production of H2O2 through the anthraquinone route is presented in this review,highlighting recent innovative technology on these aspects developed independently.The technical prospect and scientific challenges associated with the direct synthesis method from hydrogen and oxygen are also briefly discussed.

“Melanosis” in the small and large intestine

Deposition of pigment in the intestinal mucosa is commonly observed by the endoscopist, especially within the colon, and particularly during investigations for constipation. Pigment may also be detected in the small intestine. Although labeled as melanosis, electron microscopy and X-ray analytical methods have provided evidence that this pigment is not melanin at all, but lipofuscin. Often, herbal remedies or anthracene containing laxatives are often historically implicated, and experimental studies in both humans and animal models have also confirmed the intimate relationship with these pharmacological or pseudo-pharmacological remedies. The appearance of melanosis coli during colonoscopy is largely due to pigment granule deposition in macrophages located in the colonic mucosa. The pigment intensity is not uniform, being more intense in the cecum and proximal colon compared to the distal colon. Possibly, this reflects higher luminal concentrations of an offending agent in the proximal compared to distal colon, differential absorption along the length of the colon, or finally, differences in macrophage distribution within the colon. Mucosal lymphoid aggregates normally display a distinct absence of pigment producing a "starry sky" appearance, especially in the rectosigmoid region. Interestingly, some focal, usually sessile, colonic mucosal neoplastic lesions, rather than submucosal lesions, may be better appreciated as pigment deposition may be absent or limited. If detected, removal and further histopathologic analysis of the polyp may be facilitated.

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.

Allelochemicals of Panax notoginseng and their effects on various plants and rhizosphere microorganisms

Panax notoginseng(Araliaceae)is an important ginseng herb with various health benefits and a history of cultivation in southwestern China over 400 years.In recent years?.notoginseng has faced serious continuous-cropping obstacles due to its large-scale cultivation.In this study,we aim to explore the allelochemicals of P.notoginseng and their interactions with various plants and rhizosphere microor-ganisms.The chemical constituents of the soil cultivated with 3-year-old P.notoginseng were studied by column chromatography,spectroscopic and GC-MS analyses.We identified 13 volatile components and isolated six triterpenes(1-4,6-7)and one anthraquinone(5).Compounds 1-7 were tested for their effects on seed germination and root elongation in P.notoginseng,corn,wheat,turnip,water spinach and Arabidopsis thaliana.We also examined the effect of compounds 1-7on the growth of ten rhizosphere microorganisms of P.notoginseng.At a concentration of 1.0 ug mL',compounds 3 and 5-7 caused the death of P.notoginseng root cells and compounds 2,6 and 7 induced the death of root cells of A.thaliana.Compounds 1-5and 7 inhibited elongation of A.thaliana root tip cells at a concentration of 10.0μg mL^-1.Moreover,at a concentration of 0.1 mg mL^-1,compounds 3,4,6 and 7 inhibited the growth of probiotics and promoted the growth of pathogens of P.notoginseng.These results suggest that these isolated ursane-type triterpenoid acids and anthraquinone are potential allelochemicals that contribute to continuous-cropping obstacles of P.notoginseng.

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.

Natural hydroxyanthraquinoid pigments as potent food grade colorants:an overview

Natural pigments and colorants are widely used in the world in many industries such as textile dying,food processing or cosmetic manufacturing.Among the natural products of interest are various compounds belonging to carotenoids,anthocyanins,chlorophylls,melanins,betalains...The review emphasizes pigments with anthraquinoid skeleton and gives an overview on hydroxyanthraquinoids described in Nature,the first one ever published.Trends in consumption,production and regulation of natural food grade colorants are given,in the current global market.The second part focuses on the description of the chemical structures of the main anthraquinoid colouring compounds,their properties and their biosynthetic pathways.Main natural sources of such pigments are summarized,followed by discussion about toxicity and carcinogenicity observed in some cases.As a conclusion,current industrial applications of natural hydroxyanthraquinoids are described with two examples,carminic acid from an insect and Arpink red^(™)from a filamentous fungus.

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.

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.

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.

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.

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.

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.

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.

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.