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Anti-inflammatory mechanism of rhein in treating asthma based on network pharmacology

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Journal of Traditional Chinese Medicine 2022年第2期42卷 296-303页

作者： FENG Junfang CHEN Ou WANG Yibiao Department of Pediatrics the Second HospitalCheeloo College of MedicineShandong UniversityJinan 250033China School of Nursing Cheeloo College of MedicineShandong UniversityJinan 250012China

OBJECTIVE:To predict the anti-inflammatory targets and related pathways of rhein in the treatment of asthma by using network pharmacology,and to further explore its potential mechanism in asthma.METHODS:The corresponding targets of rhein were obtained from the Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform(TCMSP),and the rhein-target network was constructed with Cytoscape 3.7.1 software.The Genbank and Drugbank databases were used to collect and screen asthma targets,and the rhein-target-disease interaction network was constructed.A target protein-protein interaction(PPI)network was constructed using the STRING database to screen key targets.Finally,Kyoto Encyclopedia of Genes and Genomes(KEGG)enrichment analysis was used to identify biological processes and signaling pathways.The anti-asthmatic effects of rhein were tested in vitro,and the expression levels of proteins in the mitogen-activated protein kinase/nuclear factor kappa-B(MAPK/NF-κB)signaling pathway were assessed by western blot analysis.RESULTS:Altogether,83 targets of rhein were screened in the relevant databases,989 targets of asthma were obtained in the National Center for Biotechnology Information(NCBI)GENE Database.PPI network analysis and KEGG pathway enrichment analysis predicted that rhein could regulate the epidermal active growth factor receptor(EGFR),mitogen-activated protein kinase 14(MAPK14),tumour necrosis factor receptor superfamily member 1A(TNFRSF1A),receptor tyrosineprotein kinase erb B-2(ERBB2),and other signaling pathways.Furthermore,we selected the MAPK signaling pathway to determine the anti-inflammatory effects of rhein.Consistently,further in vitro experiments demonstrated that rhein was shown to inhibit HBE cells inflammation.CONCLUSION:The anti-inflammatory mechanism of rhein in the treatment of asthma may be related to EGFR,MAPK14,TNFRSF1A and ERBB2 as well as their signaling pathways.To prevent the exacerbation of asthma,instead of targeting a single pathway or a single target,all these tar

关键词： asthma rhein anti-inflammatory agents pharmacology drug development

Potential Medicinal Value of rhein for Diabetic Kidney Disease

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中国结合医学杂志:英文版 2023年第10期29卷 951-960页

作者： MAO Xi XU Ding-qiao YUE Shi-jun FU Rui-jia ZHANG Sai TANG Yu-ping Key Laboratory of Shaanxi Administration of Traditional Chinese Medicine for TCM Compatibility Shaanxi University of Chinese MedicineXi’an712046China

Diabetic kidney disease(DKD)is the primary cause of mortality among diabetic patients.With the increasing prevalence of diabetes,it has become a major concern around the world.The therapeutic effect of clinical use of drugs is far from expected,and therapy choices to slow the progression of DKD remain restricted.Therefore,research on new drugs and treatments for DKD has been a hot topic in the medical field.It has been found that rhein has the potential to target the pathogenesis of DKD and has a wide range of pharmacological effects on DKD,such as anti-nephritis,decreasing blood glucose,controlling blood lipids and renal protection.In recent years,the medical value of rhein in the treatment of diabetes,DKD and renal disease has gradually attracted worldwide attention,especially its potential in the treatment of DKD.Currently,DKD can only be treated with medications from a single symptom and are accompanied by adverse effects,while rhein improves DKD with a multi-pathway and multi-target approach.Therefore,this paper reviews the therapeutic effects of rhein on DKD,and proposes solutions to the limitations of rhein itself,in order to provide valuable references for the clinical application of rhein in DKD and the development of new drugs.

关键词： rhein diabetic kidney disease rhein derivatives toxicity bioavailability

Structural landscape on a series of rhein:Berberine cocrystal salt solvates:The formation,dissolution elucidation from experimental and theoretical investigations

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Chinese Chemical Letters 2022年第6期33卷 3207-3211页

作者： Dezhi Yang Hongjuan Wang Qiwen Liu Penghui Yuan Ting Chen Li Zhang Shiying Yang Zhengzheng Zhou Yang Lu Guanhua Du Beijing City Key Laboratory of Polymorphic Drugs Center of Pharmaceutical PolymorphsInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China Department of Hygiene Inspection and Quarantine Science School of Public HealthSouthern Medical University(Guangdong Provincial Key Laboratory of Tropical Disease ResearchNMPA Key Laboratory for Safety Evaluation of Cosmetics)Guangzhou 510515China Beijing City Key Laboratory of Drug Target and Screening Research National Center for Pharmaceutical ScreeningInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

The specific crystalline form of a compound remarkably affects its physicochemical properties.Therefore,a detailed analysis of the structural features and intermolecular interactions of a multi-component crystal is feasible to understand the relationships among the structure,physicochemical properties and the formation mechanism.In the present study,three novel cocrystal salt solvates of rhein and berberine were reported for the first time.Various solid characterizations and theoretical computations based on density functional theory(DFT)were carried out to demonstrate the intermolecular interactions.The theoretical computation shows that the strongest interaction existed between berberine cation and rhein anion,and the electrostatic interaction play a dominant role.However,no salt bond was observed between them.Further intrinsic dissolution rate analysis in water shows that the monohydrate exhibits 17 times enhancement in comparison with rhein.The rhein and berberine combined in ionic state in cocrystal salt is the main reason for the solubility improvement.This paper suggests that the interactions between the different components can be visualized and qualitatively and quantitatively analyzed by theoretical computation,which is helpful to understand the relationship between stereochemical structure and physicochemical properties of multi-component complex.

关键词： Cocrystal rhein Berberine Theoretical computation Energy decomposition analysis Solubility

rhein inhibits transforming growth factor β1 induced plasminogen activator inhibitor-1 in endothelial cells

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Chinese Medical Journal 2003年第3期116卷 35-40页

作者：朱加明刘志红黄海东陈朝红黎磊石 Research Institute of Nephrology Jinling Hospital Nanjing University School of Medicine Nanjing 210002 China

Objectives To investigate the effect of rhein on endothelial plasminogen activator inhibitor-1 (PAI-1) mRNA expression and protein production induced by transforming growth factor β1 (TGFβ1), and to explore the mechanism of the protective action of rhein on endothelial cells. Methods A human umbilical endothelium derived cell line (ECV-304) from ATCC was used in this study. The PAI-1 mRNA expression and protein synthesis in the endothelial cells were detected by Northern blot and flow cytometry analysis, respectively. The activity of phospho-p44/p42 MAP kinase induced by TGFβ1 was determined by immunoprecipitation analysis and western blot. Results TGFβ1 rapidly increased PAI-1 mRNA expression in the endothelial cells, and this effect lasted at least 24 hours. The upregulation of PAI-1 mRNA expression induced by TGFβ1 in endothelial cells was inhibited by rhein in a dose-dependent manner. In addition, rhein inhibited endothelial PAI-1 protein production. Further study revealed that rhein had a significant inhibitory effect on the activity of phospho-p44/p42 MAP kinase induced by TGFβ1 in human endothelial cells. Conclusions Our results showed that rhein may have a protective effect on the endothelial dysfunction by inhibiting overexpression of PAI-1, indicating a way for the treatment of vascular diseases.

关键词： rhein endothelial cells plasminogen activator inhibitor-1

Nano Calcium-Deficient Hydroxyapatite/O-carboxymethyl Chitosan-CaCl_(2) Microspheres Loadedwith rheinforBone Defect Repair

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Journal of Bionic Engineering 2022年第4期19卷 1087-1099页

作者： Zhenzhen Tian Yuanyuan Guo Xiuying Yang Kebing Guo Jingou Ji Shilei Hao School of Chemistry and Chemical Engineering Chongqing UniversityNo.55University City South RoadShapingba DistrictChongqing 401331China Key Laboratory of Biorheological Science and Technology Ministry of EducationCollege of BioengineeringChongqing UniversityChongqing 400030China Guizhou KingMed Center for Clinical Laboratory Co. LtdGuizhou 550001China

Glutaraldehyde(GA),the most widely used crosslinking agent for biomaterials,is cytotoxic.CaCl_(2) is of particular interest due to its non-toxic nature.rhein can chelate Ca^(2+)and promote bone growth.Here we reported a novel nano calcium-deficient hydroxyapatite/O-carboxymethyl chitosan-CaCl_(2) microspheres loaded with rhein(RH-nCDHA/OCMC-CaCl_(2) microspheres)using CaCl_(2) as crosslinking agent for bone defect repair.The obtained microspheres were characterized by X-ray diffraction(XRD),scanning electron microscopy(SEM),thermogravimetric analysis(TG)and Fourier transform infrared spectroscopy(FT-IR).The surface of the obtained microspheres is rough with quite a few voids.The nano calcium-deficient hydroxyapatite(nCDHA)accounts for about 70% of the total weight of the microspheres,which is equivalent to the proportion of inorganic substances in human bones.A high encapsulation efficiency(EE)and loading capacity(LC)of the microspheres loaded with rhein was 90.20±0.60% and 11.03±0.30%,respectively.For microspheres using CaCl_(2) in simulated body fluid(SBF)after 14 days,the drug released continuously and bone-like apatite formed like layer.The cells on the surface of the RH-nCDHA/OCMC-CaCl_(2) microspheres grew better comparing with nCDHA/OCMC-GA microspheres and the skull defects of rats after landfill can be almost repaired after 8 weeks,which revealed the potential of the microspheres for bone repair.

关键词： Nano calcium-deficient hydroxyapatite O-carboxymethyl chitosan rhein Microspheres Bone repair

Advanced Oxidation Protein Products Regulate the Pharmacokinetics of Aloe-emodin,Emodin,rhein,and Chrysophanol in Chronic Kidney Disease Rats

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Clinical Complementary Medicine and Pharmacology 2023年第3期3卷 8-18页

作者： Tianrong Xun Xiaokang Wang Jingqian Zhao Zhufen Lin Haixing Feng Liqian Mo Xixiao Yang Department of Pharmacy Shenzhen HospitalSouthern Medical UniversityShenzhen 518100GuangdongChina Department of Pharmacy Shenzhen Longhua District Central HospitalShenzhen 518100GuangdongChina Department of Pharmacy Nanfang HospitalSouthern Medical UniversityGuangzhou 510515GuangdongChina

Background:As accelerators and products of the progression of chronic kidney disease(CKD),advanced oxidation protein products(AOPPs)affect the function of the liver.Huang Gan granules(HGGs)are commonly used to prevent the progression of CKD,but the pharmacokinetics of aloe-emodin,emodin,rhein,and chrysophanol in HGGs in CKD remain unknown.Objective:To investigate the influence and its molecular mechanism of AOPPs on the in vivo pharmacokinetics of aloe-emodin,emodin,rhein,and chrysophanol in HGGs.Methods:We constructed 5/6 nephrectomised(5/6 nx),adenine-induced(adenine)and AOPP-treated rat models.After oral administration of HGG,the concentrations of aloe-emodin,emodin,rhein,and chrysophanol in the plasma samples were detected by high-performance liquid chromatography(HPLC),and their pharmacokinetics were analysed with the PKSolver software.The plasma concentrations of IL-6 and TNF-αare detected by enzyme linked immunosorbent assay(ELISA).The RT-PCR was performed in the HepG2 cells to explore the effect of TNF-αand IL-6 on the mRNA expression of CYP1A2 and CYP3A4.Result:The results showed that the method was suitable for the quantification of four anthraquinones in plasma and excreta samples with satisfactory linear(R R^(2)>0.9931),precision(rhein,and chryso-phanol were,respectively,significantly increased and correlated with the concentration of AOPPs.In AOPPs-treated rats,the concentration of AOPPs was significantly increased and the pharmacokinetic parameters of four anthraquinones were also increased.Conclusion:In summary,inflammatory cytokine production may be one of the important causes in AOPPs’regulat-ing the pharmacokinetic of aloe-emodin,emodin,rhein,and chrysophanol in the CKD rats.Studies of aloe-emodin,emodin,rhein,and chrysophanol in CKD facilitate the appropriate prescriptio

关键词： Advanced oxidation protein products(AOPPs) Chronic kidney disease(CKD) Huang Gan granules(HGGs) Aloe-emodin Emodin rhein Chrysophanol

Protective effects of catalpol and rhein in murine experimental autoimmune encephalomyelitis via regulation of T helper (Th)1, Th2,Th17, and regulatory T cell responses

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Journal of Traditional Chinese Medicine 2019年第6期39卷 809-817页

作者： Wei Mingyan Yang Tao Li Qian Zhou Dongdong Du Zongpan Fan Yongping Department of Traditional Chinese Medicine Beijing Tiantan HospitalCapital Medical UniversityBeijing 100050China Beijing Tongrentang Traditional Chinese Medicine Hospital Beijing 100051China Department of Traditional Chinese Medicine Beijing Tiantan HospitalCapital Medical UniversityBeijing 100070China Beijing Integrative Medicine on Encephalopathy Research Institution Beijing 100070China Center for Integrative Medicine Beijing Ditan HospitalCapital Medical UniversityBeijing 100015China Department of Neurology Beijing Daxing District Hospital of Integrated Chinese and Western MedicineBeijing 100076China

OBJECTIVE:To examine the effects of catalpol and rhein on pro-and anti-inflammatory responses in C57 BL/6 mice with experimental autoimmune encephalomyelitis(EAE),a model of multiple sclerosis.METHODS:Female C57 BL/6 mice were randomly divided into four groups(n=30):(a)normal salinecontrol,(b)EAE control,(c)EAE+prednisone acetate(PA,6 mg/kg),and(d)EAE+catalpol(40 mg/kg)and rhein(5 mg/kg).EAE was induced by injection of myelin oligodendrocyte glycoprotein 35-55 plus pertussis toxin.Treatments were orally administered daily for 40 d.Disease progression and neurological function were assessed using a semi-quantitative scale of tail and limb paralysis.Brains and spinal cords were collected on Days 6,20,and 40 and assessed for histopathological changes by hematoxylin and eosin staining.Production of interleukin(IL)-2,IL-4,IL-10,and IL-17 A protein was measured by enzyme-linked immunosorbent assay.Expression of the T helper(Th)1-,Th2-,Th17-,and regulatory T cell(Treg)-specific transcription factors T-bet,GATA3,ROR-γt,and Foxp3,respectively,were analyzed by quantitative reverse-transcription polymerase chain reaction and western blot analysis.RESULTS:Combination treatment with catalpol and rhein significantly alleviated the clinical disability and neurological dysfunction of mice with EAE.Catalpol and rhein treatment also reduced the infiltration of pro-inflammatory T cells into pathological lesions;significantly increased the expression of the anti-inflammatory factors GATA3,Foxp3,IL-4,and IL-10;and significantly decreased the expression of the pro-inflammatory factors T-bet,ROR-γt,IL-2,and IL-17 A.CONCLUSION:Catalpol and rhein reduced the neurological disabilities of mice with EAE,at least in part by rebalancing the pro-and anti-inflammatory environment in the brains and spinal cords.

关键词： Multiple sclerosis Encephalomyelitis Autoimmunity Catalpol rhein Th1-Th2 balance Th17 cells

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

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Natural Products and Bioprospecting 2020年第6期10卷 445-452页

作者： Hongjuan Wang Dezhi Yang Li Li Shiying Yang Guanhua Du Yang Lu Beijing Key Laboratory of Polymorphic Drugs Center of Pharmaceutical PolymorphsInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China Beijing Key Laboratory of Drug Targets Identification and Drug Screening National Center for Pharmaceutical ScreeningInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

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.

关键词： rhein Anthraquinone Anti-inflammatory Arthritis

An innovative rhein-matrine cocrystal: Synthesis, characterization,formation mechanism and pharmacokinetic study

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Chinese Chemical Letters 2023年第2期34卷 546-549页

作者： Hongjuan Wang Dezhi Yang Wen Zhang Junke Song Ningbo Gong Mingchao Yu Shiying Yang Baoxi Zhang Qiwen Liu Guanhua Du Yang Lu Beijing Key Laboratory of Polymorphic Drugs Center of Pharmaceutical PolymorphsInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China Beijing Key Laboratory of Drug Targets Identification and Drug Screening National Center for Pharmaceutical ScreeningInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

rhein(Rhe), an anthraquinone derivative, exhibits excellent anti-inflammatory effects and other pharmacological activities, but its clinical application remains limited due to poor solubility. The present work aims at the improvement of solubility and oral bioavailability of Rhe through cocrystal formation. For this purpose, Rhe and matrine(Mat) were selected as pharmaceutical ingredient(API) and cocrystal former(CCF), respectively, and the Rhe-Mat cocrystal was synthesized and characterized by single crystal X-ray diffraction(SXRD), powder X-ray diffraction(PXRD), thermogravimetric analysis(TGA), differential scanning calorimetry(DSC). The formation mechanism of Rhe-Mat cocrystal was elucidated by molecular surface electrostatic potential(MSEP). It is worth mentioning that the 50-fold increment of dissolution in vitro was observed in pure water in the form of Rhe-Mat cocrystal. Furthermore, the in vivo studies revealed that Rhe-Mat cocrystal indicated the faster absorption rate and the higher peak blood concentration than the pure Rhe. Hence, it can be concluded that current study successfully improved the solubility and oral bioavailability of Rhe.

关键词： rhein Matrine Cocrystal Poor solubility Molecular surface electrostatic potential