α-Dihydroxychalcone-glycoside (α-DHC) isolated from the heartwood of Pterocarpus marsupium inhibits LPS induced MAPK activation and up regulates HO-1 expression in murine RAW 264.7 macrophage

Toxicology and Applied Pharmacology

Volumn 277, Issue 1, 2014, Pages 95-107

  Chakraborty, Prarthana ^a   Saraswat, Ghungroo ^a   Kabir, Syed N ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

Antioxidants; ARE regulated genes; Cytotoxicity; Inflammation; MAPKs; Phenolic glycosides

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); ALPHA DIHYDROXYCHALCONE GLYCOSIDE; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; FREE RADICAL; GLYCOSIDE; HEME OXYGENASE 1; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1BETA; INTERLEUKIN 6; KELCH LIKE ECH ASSOCIATED PROTEIN 1; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE P38; NITRIC OXIDE; PLANT EXTRACT; STRESS ACTIVATED PROTEIN KINASE; SUPEROXIDE; TRANSCRIPTION FACTOR NRF2; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DOWN REGULATION; ENZYME ACTIVATION; GENE OVEREXPRESSION; IMMUNOFLUORESCENCE; KINO; MACROPHAGE; MOUSE; MTT ASSAY; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PROTEIN DEGRADATION; PROTEIN PHOSPHORYLATION; PTEROCARPUS; UPREGULATION;

ANTIOXIDANTS; ARE REGULATED GENES; CYTOTOXICITY; INFLAMMATION; MAPKS; PHENOLIC GLYCOSIDES;

ANIMALS; ANTIOXIDANTS; BLOTTING, WESTERN; CELL LINE; CELL SURVIVAL; CYTOKINES; DOSE-RESPONSE RELATIONSHIP, DRUG; DOWN-REGULATION; FREE RADICAL SCAVENGERS; GLYCOSIDES; INFLAMMATION MEDIATORS; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MITOGEN-ACTIVATED PROTEIN KINASES; PLANT EXTRACTS; POLYMERASE CHAIN REACTION; PTEROCARPUS; UP-REGULATION;

EID: 84898482559     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2014.03.011     Document Type: Article

References (76)

1. Abraham N.G., Kappas A. Pharmacological and clinical aspects of heme oxygenase. Pharmacol. Rev. 2008, 60:79-127.
2. Achari B., Dutta P.K., Roy S.K., Chakraborty P., Sengupta J., Bandyopadhyay D., Maity J.K., Khan I.A., Ding Y., Ferreira D. Fluorescent pigment and phenol glucosides from the heartwood of Pterocarpus marsupium. J. Nat. Prod. 2012, 75:655-660.
3. Alley M.C., Scudiero D.A., Monks A., Hursey M.L., Czerwinski M.J., Fine D.L., Abbott B.J., Mayo J.G., Shoemaker R.H., Boyd M.R. Feasibility of drug screening with panels of human tumour cell lines using a microculture tetrazolium assay. Cancer Res. 1988, 48:589-601.
4. Amarowicz R., Pegg R.B., Moghaddam P.R., Barl B., Weil J.A. Free-radical scavenging capacity and antioxidant activity of selected plant species from the Canadian prairies. Food Chem. 2004, 84:551-562.
5. Bach F.H., Hancock W.W., Ferran C. Protective genes expressed in endothelial cells: a regulatory response to injury. Immunol. Today 1997, 18:483-486.
6. Baeuerle P.A., Baltimore D. NF-kB: ten years after. Cell 1996, 87:13-20.
7. Balázs V. Anti-inflammatory role of natural polyphenols and their degradation products. Severe Sepsis and Septic Shock - Understanding a Serious Killer 2012, InTech, (Available from: http://www.intechopen.com/books/severe-sepsis-and-septic-shockunderstanding-a-serious-killer/anti-inflammatory-role-of-natural-polyphenolic-compounds). R. Fernandez (Ed.).
8. Ban H.S., Suzuki K., Lim S.S., Jung H., Lee S., Ji J., Lee H.S., Lee Y.S., Shin K.H., Ohuchi K. Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide synthase and tumor necrosis factor-α by 2'-hydroxychalcone derivatives in RAW 264.7 cells. Biochem. Pharmacol. 2004, 67:1549-1557.
9. Beckman J.S., Koppenol W.H. Nitric oxide, superoxide and peroxynitrite: the good, the bad, and ugly. Am. J. Physiol. 1996, 271:C1424-C1437.
10. Beutler B., Rietschel E.T. Innate immune sensing and its roots: the story of endotoxin. Nat. Rev. Immunol. 2003, 3:169-176.
11. Blanca H., Hsieh C., Lumen B.O. Antioxidant and anti-inflammatory properties of cancer preventive peptide lunasin in RAW 264.7 macrophages. Biochem. Biophys. Res. Commun. 2009, 390:803-808.
12. Caivano M. Role of MAP kinase cascades in inducing arginine transporters and nitric oxide synthetase in RAW 264 macrophages. FEBS Lett. 1998, 429:249-253.
13. Chakravarthy B.K., Gupta S., Gambhir S.S., Gode K.D. Pancreatic beta-cell regeneration - a novel antidiabetic mechanism of Pterocarpus marsupium, Roxb. Indian J. Pharmacol. 1980, 12:123-127.
14. Cobb M.H., Goldsmith E.J. How MAP kinases are regulated. J. Biol. Chem. 1995, 270:14843-14846.
15. Dannhardt G., Kiefer W. Cyclooxygenase inhibitors - current status and future prospects. Eur. J. Med. Chem. 2001, 36:109-126.
16. Dewhirst F.E. Structure-activity relationships for inhibition of prostaglandin cyclooxygenase by phenolic compounds. Prostaglandins 1980, 20:209-222.
17. Dinkova-Kostova A.T., Talalay P. Direct and indirect antioxidant properties of inducers of cytoprotective proteins. Mol. Nutr. Food Res. 2008, 52:128-138.
18. Dinkova-Kostova A.T., Abeygunawardana C., Talalay P. Chemoprotective properties of phenylpropenoids, bis (benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers. J. Med. Chem. 1998, 41:5287-5296.
19. Dinkova-Kostova A.T., Cheah J., Samouilov A., Zweier J.L., Bozak R.E., Hicks R.J., Talalay P. Phenolic Michael reaction acceptors: combined direct and indirect antioxidant defenses against electrophiles and oxidants. Med. Chem. 2007, 3:261-268.
20. Du Y., Guo H., Lou H. Grape seed polyphenols protect cardiac cells from apoptosis via induction of endogenous antioxidant enzymes. J. Agric. Food Chem. 2007, 55:1695-1701.
21. Dulley J.R., Grieve P.A. A simple technique for eliminating interference by detergents in the Lowry method of protein determination. Anal. Biochem. 1975, 64:136-141.
22. Fujimura T., Ohta T., Oyama K., Miyashita T., Miwa K. Role of cyclooxygenase-2 in the carcinogenesis of gastrointestinal tract cancers: a review and report of personal experience. World J. Gastroenterol. 2006, 12:1336-1345.
23. Gautam R., Srivastava A., Jachak S.M., Saklani A. Anti-inflammatory, cyclooxygenase (COX)-2, COX-1 inhibitory and antioxidant effects of Dysophylla stellata Benth. Fitoterapia 2010, 81:45-49.
24. Gilroy D.W., Lawrence T., Perretti M., Rossi A.G. Inflammatory resolution: new opportunities for drug discovery. Nat. Rev. Drug Discov. 2004, 3:401-416.
25. Girotti A.W. Lipid hydroperoxide generation, turnover, and effector action in biological systems. J. Lipid Res. 1998, 39:1529-1542.
26. Goldman R., Stoyanovsky D.A., Day B.W., Kagan V.E. Reduction of phenoxyl radicals by thioredoxin results in selective oxidation of its SH-groups to disulfides. An antioxidant function of thioredoxin. Biochemistry 1995, 34:4765-4772.
27. Hougee S., Faber J., Sanders A., Jong R.B., Berg W.B.V.D., Garssen J., Hoijer M.A., Smit H.F. Selective COX-2 inhibition by a Pterocarpus marsupium extract characterized by pterostilbene, and its activity in healthy human volunteers. Planta Med. 2005, 71:387-392.
28. Jahromi M.A.F., Ray A.B., Chansouria J.P.N. Antihyperlipidemic effect of flavonoids from Pterocarpus marsupium. J. Nat. Prod. 1993, 56:989-994.
29. Jain D., Patel N., Somani R. Anti-diarrhoeal activity of ethanolic heartwood extract of Pterocarpus marsupium. Pharmacologyonline 2011, 1:552-559.
30. Jin X.Y., Lee S.H., Park P., Hur J., Kim S., Kim H.S., Sohn D.H. 2'-Methoxy-4'6'-bis(methoxymethoxy)chalcone inhibits nitric oxide production in lipopolysaccharide-stimulated raw 264.7 macrophages. Basic Clin. Pharmacol. Toxicol. 2010, 106:454-460.
31. John J.A., Shahidi F. Phenolic compounds and antioxidant activity of Brazil nut (Bertholletia excelsa). J. Funct. Foods 2010, 2:196-209.
32. Joshi M.C., Dorababu M., Prabha T., Kumar M.M., Goel R.K. Effects of Pterocarpus marsupium on NIDDM-induced rat gastric ulceration and mucosal offensive and defensive factors. Indian J. Pharmacol. 2004, 36:296-302.
33. Kanoff M.E., Smith P.D. Isolation of whole mononuclear cells from peripheral blood and cord blood. Curr. Protoc. Immunol. 1996, (Supplement 19: 7.1.1-7.1.7), John Wiley & Sons, Inc., New York, (1997).
34. Karin M. The beginning of the end: IκB kinase (IKK) and NF-κB activation. J. Biol. Chem. 1999, 274:27339-27342.
35. Kim A.R., Lee M.S., Shin T.S., Hua H., Jang B.C., Choi J.S., Byun D.S., Utsuki T., Ingram D., Kim H.R. Phlorofucofuroeckol A inhibits the LPS-stimulated iNOS and COX-2 expressions in macrophages via inhibition of NF-κB, Akt, and p38 MAPK. Toxicol. in Vitro 2011, 25:1789-1795.
36. Kirtikar K.R., Basu B.D. Indian Medicinal Plants 2012, vol. 1:828. International Book Distributors, New Delhi. 2nd ed.
37. Kumar K.S., Ganesan K., Rao P.V.S. Antioxidant potential of solvent extracts of Kappaphycus alvarezii (Doty) Doty - an edible seaweed. Food Chem. 2008, 107:289-295.
38. LaDuca J.R., Gaspari A.A. Targeting tumor necrosis factor alpha. New drugs used to modulate inflammatory diseases. Dermatol. Clin. 2001, 19:617-635.
39. Lee J., Surh Y. Nrf2 as a novel molecular target for chemoprevention. Cancer Lett. 2005, 224:171-184.
40. Lee J., Jung H.S., Giang P.M., Jin X., Lee S., Son P.T., Lee D., Hong Y., Lee K., Lee J.J. Blockade of nuclear factor-κB signaling pathway and anti-inflammatory activity of cardamomin, a chalcone analog from Alpinia conchigera. J. Pharm. Exp. Ther. 2006, 316:271-278.
41. Lee I.K., Kim Y.S., Jang Y.W., Jung J.Y., Yun B.S. New antioxidant polyphenols from the medicinal mushroom Inonotus obliquus. Bioorg. Med. Chem. 2007, 17:6678-6681.
42. Li Q., Verma I.M. NF-κB regulation in the immune system. Nat. Rev. Immunol. 2002, 2:725-734.
43. Liew F.Y. The role of innate cytokines in inflammatory response. Immunol. Lett. 2003, 85:131-134.
44. _)-epigallocatechin-3-gallate, and propyl gallate. J. Agric. Food Chem. 2000, 48:2736-2743.
45. Liu Y., Nair M.G. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. J. Nat. Prod. 2010, 73:1193-1195.
46. Liu H., Chang A.S., Teng C., Chen C., Tsai A., Yang C. Potent anti-inflammatory effects of denbinobin mediated by dual inhibition of expression of inducible NO synthase and cyclooxygenase 2. Shock 2011, 35:191-197.
47. Long L.H., Clement M.V., Halliwell B. Artifacts in cell culture: rapid generation of hydrogen peroxide on addition of (-)-epigallocatechin, (-)-epigallocatechin gallate, (+)-catechin, and quercetin to commonly used cell culture media. Biochem. Biophys. Res. Commun. 2000, 273:50-53.
48. Lu Y., Foo L.Y. Antioxidant activities of polyphenols from sage (Salvia officinalis). Food Chem. 2001, 75:197-202.
49. Mackeen M.M., Ali A.M., Lajis N.H., Kawazu K., Hassan Z., Amran M. Antimicrobial, antioxidant, antitumor-promoting and cytotoxic activities of different plant part extracts of Garcinia atroviridis Griff ex. T. Anders. J Ethnopharmacol. 2000, 72:395-402.
50. Mankani K.L., Krishna V., Manjunatha B.K., Vidya S.M., Singh S.D.J., Manohara Y.N., Raheman A., Avinash K.R. Evaluation of hepatoprotective activity of stem bark of Pterocarpus marsupium Roxb. Indian J. Pharmacol. 2005, 37:165-168.
51. Manpreet K., Harminder P., Anon E. Wealth of India 2003, vol. 7:302-305. CSIR, New Delhi.
52. Mohan R., Birari R., Karmase A., Jagtap S., Bhutani K.K. Antioxidant activity of a new phenolic glycoside from Lagenaria siceraria Stand. fruits. Food Chem. 2012, 132:244-251.
53. Morgan M.M., Clayton C.C., Heinricher M.M. Dissociation of hyperalgesia from fever following intracerebroventricular administration of interleukin-1β in the rat. Brain Res. 2004, 1022:96-100.
54. Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem. 2007, 42:125-137.
55. Padhye S., Ahmad A., Oswal N., Sarkar F.H. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs. J. Haematol. Oncol. 2009, 2:38. 10.1186/1756-8722-2-38.
56. Pan M., Lin-Shiau S., Lin J. Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down-regulation of IκB kinase and NFκB activation in macrophages. Biochem. Pharmacol. 2000, 60:1665-1676.
57. Pandey M.K., Sandur S.K., Sung B., Sethi G., Kunnumakkara A.B., Aggarwal B.B. Butein, a tetrahydroxychalcone, inhibits nuclear factor NF-κB and NF-κB regulated gene expression through direct inhibition of IκB-α kinase β on cysteine 179 residue. J. Biol. Chem. 2007, 282:17340-17350.
58. Remsberg C.M., Yáñez J.A., Ohgami Y., Vega-Villa K.R., Rimando A.M., Davies N.M. Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity. Phytother. Res. 2008, 22:169-179.
59. Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20:933-956.
60. Samuel J.B., Stanley J.A., Princess R.A., Shanthi P., Sebastian M.S. Gestational cadmium exposure-induced ovotoxicity delays puberty through oxidative stress and impaired steroid hormone levels. J. Med. Toxicol. 2011, 7:195-204.
61. Shin E.M., Zhou H.Y., Guo L.Y., Kim J.A., Lee S.H., Merfort I., Kang S.S., Kim H.S., Kim S., Kim Y.S. Anti-inflammatory effects of glycyrol isolated from Glycyrrhiza uralensis in LPS-stimulated RAW264.7 macrophages. Int. Immunopharmacol. 2008, 8:1524-1532.
62. Silverman N., Maniatis T. NF-κB signaling pathways in mammalian and insect innate immunity. Genes Dev. 2001, 15:2321-2342.
63. Sivakumar P.M., Prabhakar P.K., Doble M. Synthesis, antioxidant evaluation and quantitative structure-activity relationship studies of chalcones. Med. Chem. Res. 2010, 19:1-17.
64. Smith W.L., DeWitt D.L., Garavito R.M. Cyclooxygenases: structural, cellular, and molecular biology. Annu. Rev. Biochem. 2000, 69:145-182.
65. Song Y., Connor D.T., Doubleday R., Sorensen R.J., Sercel A.D., Unangst P.C., Roth B.D., Gilbertsen R.B., Chan K., Schrier D.J., Guglietta A., Bornemeier D.A., Dyer R.D. J. Med. Chem. 1999, 42:1151-1160.
66. Strober W. Trypan blue exclusion test of cell viability. Curr. Protoc. Immunol. 1997, John Wiley & Sons, Inc., New York, (Supplement 21; A.3B.1-A.3B.2).
67. Surh Y.J. Cancer chemoprevention with dietary phytochemicals. Nat. Rev. Cancer 2003, 3:768-780.
68. Surh Y.J., Na H.K. NF-kB and Nrf2 as prime targets for chemoprevention and cytoprotection with anti-inflammatory and antioxidant phytonutrients. Genes Nutr. 2008, 2:313-317.
69. Surh Y.J., Kundu J.K., Na H.K. Nrf2 as a master redox switch in turning on the cellular signaling involved in the induction of cytoprotective genes by some chemopreventive phytochemicals. Planta Med. 2008, 74:1526-1539.
70. Tanifuji S., Aizu-Yokota E., Funakoshi-Tago M., Sonoda Y., Inoue H., Kasahara T. Licochalcones suppress degranulation by decreasing the intracellular Ca2+ level and tyrosine phosphorylation of ERK in RBL-2H3 cells. Int. Immunopharmacol. 2010, 10:769-776.
71. Tsao R. Chemistry and biochemistry of dietary polyphenols. Nutrients. 2010, 2:1231-1246.
72. Ulevitch R.J., Tobias P.S. Receptor-dependent mechanisms of cell stimulation by bacterial endotoxin. Annu. Rev. Immunol. 1995, 13:437-457.
73. Wiseman H., Halliwell B. Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer. Biochem. J. 1996, 313:17-29.
74. Xing Z., Gauldie J., Cox G., Baumann H., Jordana M., Lei X., Achong M.K. IL-6 is an antiinflammatory cytokine required for controlling local or systemic acute inflammatory responses. J. Clin. Invest. 1998, 101:311-320.
75. Yadav V.R., Prasad S., Sung B., Aggarwal B.B. The role of chalcones in suppression of NF-κB mediated inflammation and cancer. Int. Immunopharmacol. 2011, 11:295-309.
76. Yen G., Duh P., Huang D., Hsu C., Fu T.Y. Protective effect of pine (Pinus morrisonicola Hay.) needle on LDL oxidation and its anti-inflammatory action by modulation of iNOS and COX-2 expression in LPS-stimulated RAW 264.7 macrophages. Food Chem. Toxicol. 2008, 46:175-185.