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:
-
- 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:
- 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.
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
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.
@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}
}
Web of Science
Works referenced in this record:
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
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
Synthesis, Characterization, Antioxidative Activity and DNA Binding Properties of the Copper(II), Zinc(II), Nickel(II) Complexes with 1,2-Di(4′-iminonaringenin)ethane
journal, January 2008
- Li, Yong; Yang, Zheng-yin; Li, Tian-rong
- CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 56, Issue 11
Reactivity of Chromium(III) Nutritional Supplements in Biological Media: An X-Ray Absorption Spectroscopic Study
journal, May 2008
- Nguyen, Annie; Mulyani, Irma; Levina, Aviva
- Inorganic Chemistry, Vol. 47, Issue 10
µ 3 -Oxotrimetal acetato-complexes of chromium, manganese, iron, cobalt, rhodium, and iridium
journal, January 1973
- Uemura, Sakae; Spencer, Alwyn; Wilkinson, Geoffrey
- J. Chem. Soc., Dalton Trans., Issue 23
The use of conductivity measurements in organic solvents for the characterisation of coordination compounds
journal, October 1971
- Geary, W. J.
- Coordination Chemistry Reviews, Vol. 7, Issue 1
1H and13C-NMR data of hydroxyflavone derivatives
journal, January 2007
- Park, Younghee; Moon, Byoung-Ho; Lee, Eunjung
- Magnetic Resonance in Chemistry, Vol. 45, Issue 8
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
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
Raman and surface-enhanced Raman spectra of flavone and several hydroxy derivatives
journal, January 2007
- Teslova, Tatyana; Corredor, Charlie; Livingstone, Richard
- Journal of Raman Spectroscopy, Vol. 38, Issue 7
Syntheses of 5-Hydroxyflavone-Transition Metal Complexes
journal, August 1978
- Hiraki, Katsuma; Onishi, Masayoshi; Ikeda, Tsuyoshi
- Bulletin of the Chemical Society of Japan, Vol. 51, Issue 8
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
Chemical Methods To Evaluate Antioxidant Ability
journal, October 2010
- Liu, Zai-Qun
- Chemical Reviews, Vol. 110, Issue 10
Antioxidant property of quercetin–Cr(III) complex: The role of Cr(III) ion
journal, January 2009
- Chen, Weijun; Sun, Shaofang; cao, Wei
- Journal of Molecular Structure, Vol. 918, Issue 1-3
Raman and surface-enhanced Raman spectra of flavone and several hydroxy derivatives
journal, January 2007
- Teslova, Tatyana; Corredor, Charlie; Livingstone, Richard
- Journal of Raman Spectroscopy, Vol. 38, Issue 7
1H and13C-NMR data of hydroxyflavone derivatives
journal, January 2007
- Park, Younghee; Moon, Byoung-Ho; Lee, Eunjung
- Magnetic Resonance in Chemistry, Vol. 45, Issue 8
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
Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals
journal, March 2001
- Afanas’eva, Igor B.; Ostrakhovitch, Elena A.; Mikhal’chik, Elena V.
- Biochemical Pharmacology, Vol. 61, Issue 6
Chemical Methods To Evaluate Antioxidant Ability
journal, October 2010
- Liu, Zai-Qun
- Chemical Reviews, Vol. 110, Issue 10
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
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
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
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
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
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
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
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