Is nitric oxide decrease observed with naphthoquinones in LPS stimulated RAW 264.7 macrophages a beneficial property?

PLoS ONE

Volumn 6, Issue 8, 2011, Pages

  Pinho, Brígida R ^a   Sousa, Carla ^a   Valentão, Patrícia ^a   Andrade, Paula B ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; 1,4 NAPHTHOQUINONE; 1,4 NAPHTHOQUINONE DERIVATIVE; 3 NITROTYROSINE; 4 HYDROQUINONE; ANTIINFLAMMATORY AGENT; DEXAMETHASONE; DIOSQUINONE; INTERLEUKIN 6; JUGLONE; LIPOPOLYSACCHARIDE; MENADIONE; NAPHTHAZARIN; NITRIC OXIDE; PEROXYNITRITE; PLUMBAGIN; SUPEROXIDE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; CYTOKINE; NAPHTHOQUINONE;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; MACROPHAGE ACTIVATION; MACROPHAGE FUNCTION; MOUSE; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; ANIMAL; BIOSYNTHESIS; DOWN REGULATION; DRUG EFFECT; MACROPHAGE; METABOLISM;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CYTOKINES; DOWN-REGULATION; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MACROPHAGE ACTIVATION; MACROPHAGES; MICE; NAPHTHOQUINONES; NITRIC OXIDE; OXIDATIVE STRESS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 80052053783     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0024098     Document Type: Article

References (40)

1. Babula P, Adam V, Havel L, Kizek R, (2009) Noteworthy secondary metabolites naphthoquinones - their occurrence, pharmacological properties and analysis. Curr Pharm Anal 5: 47-68.
2. Mallavadhani UV, Panda AK, Rao YR, (1998) Pharmacology and chemotaxonomy of Diospyros. Phytochemistry 49: 901-951.
3. Costa MA, Alves AC, Seabra RM, Andrade PB, (1998) Naphthoquinones of Diospyros chamaethamnus. Planta Med 64: 391.
4. Adeniyi BA, Fong HHS, Pezzuto JM, Luyengi L, Odelola HA, (2000) Antibacterial activity of diospyrin, isodiospyrin and bisisodiospyrin from the root of Diospyros piscatorial (Gurke) (Ebenaceae). Phytother Res 14: 112-117.
5. Theerachayanan T, Sirithunyalug B, Piyamongkol S, (2007) Antimalarial and antimycobacterial activities of dimeric naphthoquinones from Diospyros glandulosa and Diospyros rhodocalyx. CMU J Nat Sci 6: 253-259.
6. Hernández-Pérez M, Rabanal RM, de la Torre MC, Rodríguez B, (1995) Analgesic, anti-inflammatory, antipyretic and haematological effects of aethiopinone, an o-naphthoquinone diterpenoid from Salvia aethiopis roots and two hemisynthetic derivatives. Planta Med 61: 505-509.
7. Chakrabarty S, Roy M, Hazra B, Bhattacharya RK, (2002) Induction of apoptosis in human cancer cell lines by diospyrin, a plant-derived bisnaphthoquinonoid, and its synthetic derivatives. Cancer Lett 188: 85-93.
8. O'Brien PJ, (1991) Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact 80: 1-41.
9. Kuke C, Williamson EM, Roberts MF, Watt R, Hazra B, et al. (1998) Antiinflammatory activity of binaphthoquinones from Diospyros species. Phytother Res 12: 155-158.
10. Checker R, Sharma D, Sandur SK, Khanem S, Poduval TB, (2009) Anti-inflammatory effects of plumbagin are mediated by inhibition of NF-kappaB activation in lymphocytes. Int Immunopharmacol 9: 949-958.
11. Subbaramaiah K, Bulic P, Li Y, Dannenberg AJ, Parco DS, (2001) Development and use of a gene promoter-based screen to identify novel inhibitors of cyclooxygenase-2 transcription. J Biomol Screen 6: 101-110.
12. Wang JP, Raung SL, Chang LC, Kuo SC, (1995) Inhibition of hind-paw edema and cutaneous vascular plasma extravasation in mice by acetylshikonin. Eur J Pharmacol 272: 87-95.
13. Cheng YW, Chang CY, Lin KL, Hu CM, Lin CH, et al. (2008) Shikonin derivatives inhibited LPS-induced NOS in RAW 264.7 cells via downregulation of MAPK/NF-κB signaling. J Ethnopharmacol 120: 264-271.
14. Han A-R, Min H-Y, Nam J-W, Lee N-Y, Wiryawan A, et al. (2008) Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Chem Pharm Bull 56: 1314-1316.
15. Moncada S, Plamer RMJ, Higgs EA, (1991) Nitric oxide: physiology, pathophysiology and pharmacology. Pharmacol Rev 43: 109-142.
16. Swett MJ, Hume DA, (1996) Endotoxin signal transduction in macrophages. J Leukoc Biol 60: 8-26.
17. Andreakos ET, Foxwell BM, Brennan FM, Maini RN, Feldmann M, (2002) Cytokines and anti-cytokine biological in autoimmunity: present and future. Cytokine Growth Factor Rev 13: 299-313.
18. El-Omar EM, Carrington M, Chow W-H, Kenneth EL, McColl KEL, et al. (2000) Interleukin-1 polymorphisms associated with increased risk of gastric cancer. Nature 404: 398-402.
19. Stein B, Sutherland MSK, (1998) IL-6 as a drug discovery target. Drug Discov Today 3: 202-2013.
20. Maeda S, Omata M, (2008) Inflammation and cancer: Role of nuclear factor-kappaB activation. Cancer Sci 99: 836-842.
21. Laskin DL, Pendino KJ, (1995) Macrophages and inflammatory mediators in tissue injury. Ann Rev Pharmacol Toxicol 35: 655-677.
22. Alves AC, Costa MA, Paul MI, (1983) Naphthoquinones of Diospyros batocana. Planta Med 47: 121-124.
23. Lobner D, (2000) Comparison of the LDH and MTT assays for quantifying cell death: validity for neuronal apoptosis? J Neurosci Methods 96: 147-152.
24. Sousa C, Pontes H, Carmo H, Dinis-Oliveira RJ, Valentão P, et al. (2009) Water extracts of Brassica oleracea var. costata potenciate paraquat toxicity to rat hepatocytes in vitro. Toxicol in Vitro 23: 1131-1138.
25. Moreira-Gonçalves D, Henriques-Coelho T, Fonseca H, Ferreira RM, Amado F, et al. (2011) Moderate exercise training provides left ventricular tolerance to acute pressure overload. Am J Physiol Heart Circ Physiol 300: H1044-1052.
26. Adams DO, Hamiltonm TA, (1984) The cell biology of macrophage activation. Ann Rev Immunol 2: 283-318.
27. Nathan CF, Hibbs JB Jr, (1991) Role of nitric oxide synthesis in macrophage antimicrobial activity. Curr Opinion Immunol 3: 65-70.
28. De Vera ME, Taylor BS, Wang Q, Shapiro RA, Billiar TR, et al. (1997) Dexamethasone suppresses iNOS gene expression by upregulating IkB-α and inhibiting NF-κB. Am J Physiol Gastrointest Liver Physiol 273: 1290-1296.
29. Sun Z, Andersson R, (2002) NF-κB activation and inhibition: a review. Shock 18: 99-106.
30. Sandur SK, Ichikawa H, Sethi G, Ahn KS, Aggarwal BB, (2006) Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) suppresses NF-κB activation and NF-κB-regulated gene products through modulation of p65 and IκBα kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. J Biol Chem 281: 17023-17033.
31. Fotakis G, Timbrell JA, (2005) In vitro cytotoxicity assays: Comparison of LDH, neutral red, MTT and protein assay in hepatoma cells lines following exposure to cadmium chloride. Toxicol Lett 160: 171-177.
32. Chia JKS, Pollack M, Guelde G, Koles NL, Miller M, (1989) Lipopolysaccharide (LPS)- Reactive monoclonal antibodies fail to inhibit LPS-induced tumor necrosis factor secretion by mouse-derived macrophages. J Infect Dis 159: 872-880.
33. Klaus V, Hartmann T, Gambini J, Graf P, Stahl W, et al. (2010) 1,4-Naphthoquinones as inducers of oxidative damage and stress signalling in HaCaT human keratinocytes. Arch Biochem Biophys 496: 93-100.
34. Murakami K, Haneda M, Iwata S, Yoshino M, (2010) Effect of hydroxyl substituent on the prooxidant action of naphthoquinone compounds. Toxicol in Vitro 24: 905-909.
35. Inbaraj JJ, Chignell CF, (2004) Cytotoxic action of juglone and plumbagin: A mechanistic study using HaCaT keratinocytes. Chem Res Toxicol 17: 55-62.
36. Liu X, Chuman H, (2005) Determination of solute lipophilicity by reversed-phase high-performance liquid chromatography (RP-HPLC). J Med Invest 52: 293-294.
37. Gryglewski RJ, Palmer RMJ, Moncada S, (1986) Superoxide anion is involved in the breakdown of endothelium-derived vascular relaxing factor. Nature 320: 454-456.
38. Mallozzi C, Di Stasi AMM, Minetti M, (1997) Peroxynitrite modulates tyrosine-dependent signal transduction pathway of human erythrocyte band 3. FASEB J 11: 1281-1290.
39. Pfeiffer S, Mayer B, (1998) Lack of tyrosine nitration by peroxynitrite generated at physiological pH. J Biol Chem 273: 27280-27285.
40. Pfeiffer S, Schmidt K, Mayer B, (2000) Dityrosine formation outcompetes tyrosine nitration at low steady-state concentrations of peroxynitrite. J Biol Chem 275: 6346-6352.