Ellagic Acid, a Dietary Polyphenol, Inhibits Tautomerase Activity of Human Macrophage Migration Inhibitory Factor and Its Pro-inflammatory Responses in Human Peripheral Blood Mononuclear Cells.

Ellagic acid (EA), a phenolic lactone, inhibited tautomerase activity of human macrophage migration inhibitory factor (MIF) noncompetitively (Ki = 1.97 ± 0.7 μM). The binding of EA to MIF was determined by following the quenching of tryptophan fluorescence. We synthesized several EA derivatives, and their structure-activity relationship studies indicated that the planar conjugated lactone moiety of EA was essential for MIF inhibition. MIF induces nuclear translocation of NF-κB and chemotaxis of peripheral blood mononuclear cells (PBMCs) to promote inflammation. We were interested in evaluating the effect of EA on nuclear translocation of NF-κB and chemotactic activity in human PBMCs in the presence of MIF. The results showed that EA inhibited MIF-induced NF-κB nuclear translocation in PBMCs, as evident from confocal immunofluorescence microscopic data. EA also inhibited MIF-mediated chemotaxis of PBMCs. Thus, we report MIF-inhibitory activity of EA and inhibition of MIF-mediated proinflammatory responses in PBMCs by EA.

[1]  A. Adedapo,et al.  Antioxidant, antinociceptive and anti-inflammatory properties of the aqueous and ethanolic leaf extracts of Andrographis paniculata in some laboratory animals , 2015, Journal of basic and clinical physiology and pharmacology.

[2]  B. Hahn,et al.  Elevated circulating levels of the pro-inflammatory cytokine macrophage migration inhibitory factor in individuals with acute spinal cord injury. , 2015, Archives of physical medicine and rehabilitation.

[3]  Zhongkai Wu,et al.  Ellagic acid prevents monocrotaline-induced pulmonary artery hypertension via inhibiting NLRP3 inflammasome activation in rats. , 2015, International journal of cardiology.

[4]  L. Soares,et al.  Quantification of polyphenols and evaluation of antimicrobial, analgesic and anti-inflammatory activities of aqueous and acetone-water extracts of Libidibia ferrea, Parapiptadenia rigida and Psidium guajava. , 2014, Journal of ethnopharmacology.

[5]  J. Choi,et al.  Protective effect of ellagic acid on concanavalin A-induced hepatitis via toll-like receptor and mitogen-activated protein kinase/nuclear factor κB signaling pathways. , 2014, Journal of agricultural and food chemistry.

[6]  H. Paik,et al.  Investigation on Antibacterial and Antioxidant Activities, Phenolic and Flavonoid Contents of Some Thai Edible Plants as an Alternative for Antibiotics , 2014, Asian-Australasian journal of animal sciences.

[7]  P. Oteiza,et al.  The anthocyanin metabolites gallic acid, 3‐O‐methylgallic acid, and 2,4,6‐trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro‐oncogenic signals , 2014, Molecular carcinogenesis.

[8]  M. Vinayak,et al.  Ellagic Acid Induces Novel and Atypical PKC Isoforms and Promotes Caspase-3 Dependent Apoptosis by Blocking Energy Metabolism , 2014, Nutrition and cancer.

[9]  A. Galano,et al.  Ellagic acid: an unusually versatile protector against oxidative stress. , 2014, Chemical research in toxicology.

[10]  R. Rodrigo,et al.  Polyphenols in disease: from diet to supplements. , 2014, Current pharmaceutical biotechnology.

[11]  Y. Hseu,et al.  Toona sinensis Inhibits LPS-Induced Inflammation and Migration in Vascular Smooth Muscle Cells via Suppression of Reactive Oxygen Species and NF-κB Signaling Pathway , 2014, Oxidative medicine and cellular longevity.

[12]  S. Cannistraro,et al.  Binding of azurin to cytochrome c 551 as investigated by surface plasmon resonance and fluorescence , 2014, Journal of molecular recognition : JMR.

[13]  U. Bandyopadhyay,et al.  Nonsteroidal anti-inflammatory drug induces proinflammatory damage in gastric mucosa through NF-κB activation and neutrophil infiltration: anti-inflammatory role of heme oxygenase-1 against nonsteroidal anti-inflammatory drug. , 2013, Free radical biology & medicine.

[14]  Yong-Beom Park,et al.  Gallic acid, a natural polyphenolic acid, induces apoptosis and inhibits proinflammatory gene expressions in rheumatoid arthritis fibroblast-like synoviocytes. , 2013, Joint, bone, spine : revue du rhumatisme.

[15]  H. Bessler,et al.  Role of Peripheral Blood Mononuclear Cells in the Predisposition of Obese Individuals to Inflammation and Infection , 2013, Obesity Facts.

[16]  Jianbo Xiao,et al.  A Review on Structure–Activity Relationship of Dietary Polyphenols Inhibiting α-Amylase , 2013, Critical reviews in food science and nutrition.

[17]  M. Vinayak,et al.  Ellagic acid checks lymphoma promotion via regulation of PKC signaling pathway , 2013, Molecular Biology Reports.

[18]  T. Hagemann,et al.  Cancer-Related Inflammation , 2012, Journal of Clinical Immunology.

[19]  U. Farooq,et al.  Antioxidant, Antimicrobial, and Free Radical Scavenging Potential of Aerial Parts of Periploca aphylla and Ricinus communis , 2012, ISRN pharmacology.

[20]  U. Bandyopadhyay,et al.  Impact of Intravascular Hemolysis in Malaria on Liver Dysfunction , 2012, The Journal of Biological Chemistry.

[21]  U. Bandyopadhyay,et al.  Novel Anti-inflammatory Activity of Epoxyazadiradione against Macrophage Migration Inhibitory Factor , 2012, The Journal of Biological Chemistry.

[22]  Hai-bin Luo,et al.  Ellagic acid, a phenolic compound, exerts anti-angiogenesis effects via VEGFR-2 signaling pathway in breast cancer , 2012, Breast Cancer Research and Treatment.

[23]  U. Bandyopadhyay,et al.  Synthesis and bio-evaluation of human macrophage migration inhibitory factor inhibitor to develop anti-inflammatory agent. , 2011, Bioorganic & medicinal chemistry.

[24]  U. Bandyopadhyay,et al.  Tryptamine-Gallic Acid Hybrid Prevents Non-steroidal Anti-inflammatory Drug-induced Gastropathy , 2011, The Journal of Biological Chemistry.

[25]  P. Maity,et al.  Translocation of Heme Oxygenase-1 to Mitochondria Is a Novel Cytoprotective Mechanism against Non-steroidal Anti-inflammatory Drug-induced Mitochondrial Oxidative Stress, Apoptosis, and Gastric Mucosal Injury* , 2011, The Journal of Biological Chemistry.

[26]  Aurélien Grosdidier,et al.  Fast docking using the CHARMM force field with EADock DSS , 2011, J. Comput. Chem..

[27]  D. Martins,et al.  Gastroprotective and ulcer-healing mechanisms of ellagic acid in experimental rats. , 2011, Journal of agricultural and food chemistry.

[28]  P. Maity,et al.  Cysteine-3 and cysteine-4 are essential for the thioredoxin-like oxidoreductase and antioxidant activities of Plasmodium falciparum macrophage migration inhibitory factor. , 2011, Free radical biology & medicine.

[29]  Aurélien Grosdidier,et al.  SwissDock, a protein-small molecule docking web service based on EADock DSS , 2011, Nucleic Acids Res..

[30]  A. Salminen,et al.  Control of p53 and NF-κB signaling by WIP1 and MIF: role in cellular senescence and organismal aging. , 2011, Cellular signalling.

[31]  Julia L. Gregory,et al.  Macrophage Migration Inhibitory Factor and CD74 Regulate Macrophage Chemotactic Responses via MAPK and Rho GTPase , 2011, The Journal of Immunology.

[32]  Rajbir Kaur,et al.  Antimutagenic and Antioxidant Characteristics of Chukrasia tabularis A Juss Extracts , 2011, International journal of toxicology.

[33]  Kwanghee Kim,et al.  Anti-inflammatory function of arctiin by inhibiting COX-2 expression via NF-κB pathways , 2011, Journal of Inflammation.

[34]  Y. Chuang,et al.  Macrophage migration inhibitory factor regulates interleukin-6 production by facilitating nuclear factor-kappa B activation during Vibrio vulnificus infection , 2010, BMC Immunology.

[35]  P. Maity,et al.  Gallic acid prevents nonsteroidal anti-inflammatory drug-induced gastropathy in rat by blocking oxidative stress and apoptosis. , 2010, Free radical biology & medicine.

[36]  I. Boušová,et al.  Binding of naturally occurring hydroxycinnamic acids to bovine serum albumin , 2010 .

[37]  Kirk W. Johnson,et al.  Allosteric inhibition of macrophage migration inhibitory factor revealed by ibudilast , 2010, Proceedings of the National Academy of Sciences.

[38]  S. Truant,et al.  Autocrine induction of invasive and metastatic phenotypes by the MIF-CXCR4 axis in drug-resistant human colon cancer cells. , 2010, Cancer research.

[39]  T. Lawrence.  The nuclear factor NF-kappaB pathway in inflammation. , 2009, Cold Spring Harbor perspectives in biology.

[40]  E. Dahl,et al.  Dual role of macrophage migration inhibitory factor (MIF) in human breast cancer , 2009, BMC Cancer.

[41]  D. DiMaio,et al.  High-Throughput Cell-Based Screen for Chemicals That Inhibit Infection by Simian Virus 40 and Human Polyomaviruses , 2009, Journal of Virology.

[42]  C. Stalikas.  Extraction, separation, and detection methods for phenolic acids and flavonoids. , 2007, Journal of separation science.

[43]  E. Dahl,et al.  Macrophage migration inhibitory factor (MIF) promotes cell survival by activation of the Akt pathway and role for CSN5/JAB1 in the control of autocrine MIF activity , 2007, Oncogene.

[44]  Aurélien Grosdidier,et al.  EADock: Docking of small molecules into protein active sites with a multiobjective evolutionary optimization , 2007, Proteins.

[45]  R. Bucala,et al.  Macrophage migration inhibitory factor: a probable link between inflammation and cancer. , 2007, Immunity.

[46]  S. Welford,et al.  HIF1α delays premature senescence through the activation of MIF , 2006 .

[47]  Irfan Rahman,et al.  Regulation of inflammation and redox signaling by dietary polyphenols. , 2006, Biochemical pharmacology.

[48]  L. Leng,et al.  CD44 is the signaling component of the macrophage migration inhibitory factor-CD74 receptor complex. , 2006, Immunity.

[49]  H. Alakomi,et al.  Berry Phenolics: Antimicrobial Properties and Mechanisms of Action Against Severe Human Pathogens , 2006, Nutrition and cancer.

[50]  S. Welford,et al.  HIF1alpha delays premature senescence through the activation of MIF. , 2006, Genes & development.

[51]  Xiaofeng Ma,et al.  Structure-activity relationship of polyphenols that inhibit fatty acid synthase. , 2005, Journal of biochemistry.

[52]  Michael Bacher,et al.  ISO-1 Binding to the Tautomerase Active Site of MIF Inhibits Its Pro-inflammatory Activity and Increases Survival in Severe Sepsis* , 2005, Journal of Biological Chemistry.

[53]  J. Garai,et al.  Plant-derived anti-inflammatory compounds affect MIF tautomerase activity. , 2005, International immunopharmacology.

[54]  M. Dell’Agli,et al.  In vitro studies on the mechanism of action of two compounds with antiplasmodial activity: ellagic acid and 3,4,5-trimethoxyphenyl(6'-O-aalloyl)-beta-D-glucopyranoside. , 2003, Planta medica.

[55]  Hong-Wei Sun,et al.  Macrophage Migration Inhibitory Factor Interactions with Glutathione and S-Hexylglutathione* , 1998, The Journal of Biological Chemistry.

[56]  N. D. Buniatian,et al.  [The protective action of ellagic acid in experimental myocarditis]. , 1998, Eksperimental'naia i klinicheskaia farmakologiia.

[57]  G. Stoner,et al.  Structure-function relationships of the dietary anticarcinogen ellagic acid. , 1996, Carcinogenesis.