A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties

Rocha, Reginaldo C.; Alexiou, Anamaria D.P.; Decandio, Carla C.; Almeida, Sabrina da N.; Ferreira, Marcelo J.P.; Romoff, Paulete

doi:10.3390/molecules20046310

Title: A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties

Abstract

A new trinuclear oxo-centered chromium(III) complex with formula [Cr₃O(CH₃CO₂)₆(L)(H₂O)₂] (L = 5-hydroxyflavone, known as primuletin) was synthetized and characterized by ESI mass spectrometry, thermogravimetry, and ¹H-NMR, UV-Vis, and FTIR spectroscopies. In agreement with the experimental results, DFT calculations indicated that the flavonoid ligand is coordinated to one of the three Cr(III) centers in an O,O-bidentate mode through the 5-hydroxy/4-keto groups. In a comparative study involving the uncoordinated primuletin and its corresponding complex, systematic reactions with the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed that antiradical activity increases upon complexation.

Authors:

Rocha, Reginaldo C. ^[1]; Alexiou, Anamaria D.P. ^[2]; Decandio, Carla C. ^[2]; Almeida, Sabrina da N. ^[2]; Ferreira, Marcelo J.P. ^[3]; Romoff, Paulete ^[2]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Univ. Presbiteriana Mackenzie, Sao Paulo (Brazil)
Univ. de Sao Paulo, Sao Paulo (Brazil)

Publication Date:: Fri Apr 10 00:00:00 EDT 2015

Research Org.:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1208875

Grant/Contract Number:: AC52-06NA25396

Resource Type:: Accepted Manuscript

Journal Name:: Molecules

Additional Journal Information:: Journal Volume: 20; Journal Issue: 4; Journal ID: ISSN 1420-3049

Publisher:: MDPI

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; antiradical activity; chromium(III) complexes; flavonoids; metal-oxo cluster; primuletin

Citation Formats


                    Rocha, Reginaldo C., Alexiou, Anamaria D.P., Decandio, Carla C., Almeida, Sabrina da N., Ferreira, Marcelo J.P., and Romoff, Paulete. A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties.  United States: N. p., 2015. 
Web.  doi:10.3390/molecules20046310.

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                    Rocha, Reginaldo C., Alexiou, Anamaria D.P., Decandio, Carla C., Almeida, Sabrina da N., Ferreira, Marcelo J.P., & Romoff, Paulete. A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties.  United States.  https://doi.org/10.3390/molecules20046310

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                    Rocha, Reginaldo C., Alexiou, Anamaria D.P., Decandio, Carla C., Almeida, Sabrina da N., Ferreira, Marcelo J.P., and Romoff, Paulete. Fri .  
"A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties".  United States.  https://doi.org/10.3390/molecules20046310.  https://www.osti.gov/servlets/purl/1208875.

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@article{osti_1208875,

  title        = {A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties},

  author       = {Rocha, Reginaldo C. and Alexiou, Anamaria D.P. and Decandio, Carla C. and Almeida, Sabrina da N. and Ferreira, Marcelo J.P. and Romoff, Paulete},

  abstractNote = {A new trinuclear oxo-centered chromium(III) complex with formula [Cr₃O(CH₃CO₂)₆(L)(H₂O)₂] (L = 5-hydroxyflavone, known as primuletin) was synthetized and characterized by ESI mass spectrometry, thermogravimetry, and ¹H-NMR, UV-Vis, and FTIR spectroscopies. In agreement with the experimental results, DFT calculations indicated that the flavonoid ligand is coordinated to one of the three Cr(III) centers in an O,O-bidentate mode through the 5-hydroxy/4-keto groups. In a comparative study involving the uncoordinated primuletin and its corresponding complex, systematic reactions with the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed that antiradical activity increases upon complexation.},

  doi          = {10.3390/molecules20046310},

  journal      = {Molecules},

  number       = 4,

  volume       = 20,

  place        = {United States},

  year         = {Fri Apr 10 00:00:00 EDT 2015},

  month        = {Fri Apr 10 00:00:00 EDT 2015}

}

Copy to clipboard

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Synthesis and Characterization of Some New Complexes of Magnesium (II) and Zinc (II) with the Natural Flavonoid Primuletin
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Uivarosi, Valentina; Badea, Mihaela; Olar, Rodica
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Raman and surface-enhanced Raman spectra of flavone and several hydroxy derivatives
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1H and13C-NMR data of hydroxyflavone derivatives
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Park, Younghee; Moon, Byoung-Ho; Lee, Eunjung
Magnetic Resonance in Chemistry, Vol. 45, Issue 8
DOI: 10.1002/mrc.2010

Breakdown kinetics of the tri-chromium(III) oxo acetate cluster ([Cr3O(OAc)6]+) with some ligands of biological interest
journal, February 2007

Chaudhary, Shveta; Van Horn, J. David
Journal of Inorganic Biochemistry, Vol. 101, Issue 2
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Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals
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Chemical Methods To Evaluate Antioxidant Ability
journal, October 2010

Liu, Zai-Qun
Chemical Reviews, Vol. 110, Issue 10
DOI: 10.1021/cr900302x

Predicting How Polyphenol Antioxidants Prevent DNA Damage by Binding to Iron
journal, July 2008

Perron, Nathan R.; Hodges, James N.; Jenkins, Michael
Inorganic Chemistry, Vol. 47, Issue 14
DOI: 10.1021/ic7022727

Crystal Structures of the Isomorphous Prototypic Oxo-Centered Trinuclear Complexes [Cr ₃ O(OOCCH ₃ ) ₆ (H ₂ O) ₃ ]Cl·6H ₂ O and [Fe ₃ O(OOCCH ₃ ) ₆ (H ₂ O) ₃ ]Cl·6H ₂ O
journal, March 1997

Anson, C. E.; Bourke, J. P.; Cannon, R. D.
Inorganic Chemistry, Vol. 36, Issue 6
DOI: 10.1021/ic960960f

Antioxidant properties of complexes of flavonoids with metal ions
journal, April 2004

de Souza, Rubens F. V.; De Giovani, Wagner F.
Redox Report, Vol. 9, Issue 2
DOI: 10.1179/135100004225003897

Synthesis and Characterization of Some New Complexes of Magnesium (II) and Zinc (II) with the Natural Flavonoid Primuletin
journal, July 2013

Uivarosi, Valentina; Badea, Mihaela; Olar, Rodica
Molecules, Vol. 18, Issue 7
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Works referencing / citing this record:

Metal-ligand coordination and antiradical activity of a trichromium(III) complex with the flavonoid naringenin
journal, May 2017

Alexiou, Anamaria D. P.; Decandio, Carla C.; Almeida, Sabrina da N.
Journal of Coordination Chemistry, Vol. 70, Issue 12
DOI: 10.1080/00958972.2017.1328735

Metal-ligand coordination and antiradical activity of a trichromium(III) complex with the flavonoid naringenin
text, January 2017

Alexiou, Anamaria D. P.; Decandio, Carla C.; Almeida, Sabrina Da N.
Taylor & Francis
DOI: 10.6084/m9.figshare.5182795.v1

Metal-ligand coordination and antiradical activity of a trichromium(III) complex with the flavonoid naringenin
text, January 2017

Alexiou, Anamaria D. P.; Decandio, Carla C.; Almeida, Sabrina Da N.
Taylor & Francis
DOI: 10.6084/m9.figshare.5182795

Determination of Anticancer Zn(II)–Rutin Complex Structures in Solution through Density Functional Theory Calculations of ¹H NMR and UV–VIS Spectra
journal, February 2020

Da Silva, Haroldo C.; De Souza, Leonardo A.; Dos Santos, Hélio F.
ACS Omega, Vol. 5, Issue 6
DOI: 10.1021/acsomega.9b04174

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Title: A trinuclear oxo-chromium(III) complex containing the natural flavonoid primuletin: Synthesis, characterization, and antiradical properties

Abstract

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