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Synthesis, characterization, and anti-inflammatory activities of rare earth metal complexes of luteolin

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Abstract

Twelve as yet, unreported complexes of luteolin were synthesized with various rare earth ions through refluxing in ethanol. The characterization of these complexes by elemental analysis, infrared spectra, and differential scanning calorimeter demonstrated that luteolin coordinated the various rare earth ions in a similar manner. Experiments designed to study the anti-inflammatory activities of these rare earth-luteolin complexes indicated that they had a significant inhibitory effect on xylene-induced ear edema in mice. Five complexes containing La3+, Ho3+, Yb3+, Lu3+, and Y3+ were equally effective as luteolin and dexamethasone (DXM). However, their inhibitory effects on carrageenan-induced paw edema in mice, although significant, were weaker than that of either luteolin alone or DXM.

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References

  • Alagarsamy V, Murugesan S, Sheorey RV (2008) Synthesis and pharmacological investigation of novel 3-(benzyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents. Med Chem Res 17:564–577. doi:10.1007/s00044-008-9098-z

    Article  CAS  Google Scholar 

  • Amir M, Javed SA, Kumar H (2009) Design and synthesis of 3-[3-(substituted phenyl)-4-piperidin-1-ylmethyl-4-morpholin-4-ylmethyl-4,5-dihydro-isoxazol-5-yl]-1H-indoles as potent anti-inflammatory agents. Med Chem Res. doi:10.1007/s00044-009-9194-8

  • Kim J-H, Jin Y-R, Park B-S et al (2005) Luteolin prevents PDGF-BB-induced proliferation of vascular smooth muscle cells by inhibition of PDGF β-receptor phosphorylation. Biochem Pharm 69:1715–1721. doi:10.1016/j.bcp.2005.04.002

    Article  CAS  PubMed  Google Scholar 

  • Lee Y, Howard LR, Villalón B (1995) Flavonoids and antioxidant activity of fresh pepper (Capsicum annuum) cultivars. J Food Sci 60(3):473–476. doi:10.1111/j.1365-2621.1995.tb09806.x

    Article  CAS  Google Scholar 

  • Lu HW, Sugahara K, Sagara Y et al (2001) Effect of three flavonoids, 5, 7, 3′, 4′-tetrahydroxy-3-methoxy flavone, luteolin, and quercetin, on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophil. Arch Biochem Biophys 393(1):73–77. doi:10.1006/abbi.2001.2457

    Article  CAS  PubMed  Google Scholar 

  • Lv P-C, Li H-Q, Xue J-Y et al (2009) Synthesis and biological evaluation of novel luteolin derivatives as antibacterial agents. Eur J Med Chem 44:908–914. doi:10.1016/j.ejmech.2008.01.013

    Article  CAS  PubMed  Google Scholar 

  • Maccà C, Soldà L, Favaro G et al (2007) A pH-stat study of the reaction of some transition metal cations with disodium ethylenedinitrilotetraacetate (EDTA) and its analytical application. Talanta 72:655–662. doi:10.1016/j.talanta.2006.11.035

    Article  PubMed  Google Scholar 

  • Petrov AR, Rufanov KA, Harms K et al (2009) Re-investigation of ortho-metalated N, N-dialkylbenzylamine complexes of rare-earth metals. First structurally characterized arylates of neodymium and gadolinium Li[LnAr4]. J Organomet Chem 694:1212–1218. doi:10.1016/j.jorganchem.2008.12.020

    Article  CAS  Google Scholar 

  • Phosrithong N, Ungwitayatorn J (2009) Molecular docking study on anticancer activity of plant-derived natural products. Med Chem Res. doi:10.1007/s00044-009-9233-5

  • Srinivasan K, Govindarajan S, Harrison WTA (2009) Divalent metal complexes of formylhydrazine: syntheses and crystal structures of M(CH4N2O)2(H2O)2·2NO3 (M = Zn, Co). Inorg Chem Commun 12:619–621. doi:10.1016/j.inoche.2009.05.002

    Article  CAS  Google Scholar 

  • Tsai F-S, Peng W-H, Wang W-H et al (2007) Effects of luteolin on learning acquisition in rats: involvement of the central cholinergic system. Life Sci 80:1692–1698. doi:10.1016/j.lfs.2007.01.055

    Article  CAS  PubMed  Google Scholar 

  • Venezia M, Alonzo G, Palmisano L (2008) EDTA excess Zn (II) back-titration in the presence of 4-(2-pyridylazo)-resorcinol indicator and naphthol green β as inert dye for determining Cr(III) as Cr(III)/EDTA complex: application of the method to a leather industry wastewater. J Hazard Mater 151:356–363. doi:10.1016/j.jhazmat.2007.05.081

    Article  CAS  PubMed  Google Scholar 

  • Yoo DR, Jang YH, Jeon YK et al (2009) Proteomic identification of anti-cancer proteins in luteolin-treated human hepatoma Huh-7 cells. Cancer Lett 282:48–54. doi:10.1016/j.canlet.2009.02.051

    Article  CAS  PubMed  Google Scholar 

  • Zhou J, Wang L-F, Wang J-Y et al (2001) Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes. J Inorg Biochem 83(1):41–48

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

This work was supported by the Natural Science Foundation of Zhejiang Province (Y205706).

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Correspondence to Lisheng Wang.

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Li, J., Wang, L., Bai, H. et al. Synthesis, characterization, and anti-inflammatory activities of rare earth metal complexes of luteolin. Med Chem Res 20, 88–92 (2011). https://doi.org/10.1007/s00044-009-9289-2

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  • DOI: https://doi.org/10.1007/s00044-009-9289-2

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