Medicinal Chemistry Research

, Volume 21, Issue 7, pp 1341–1346 | Cite as

Antioxidant activities and transition metal ion chelating studies of some hydroxyl Schiff base derivatives

Original Research

Abstract

Several hydroxyl Schiff base (HSB) compounds (110) with good radical scavenging activity (RSA) were designed. Compounds 6, 7, and 10 showed better RSAs than the common synthetic antioxidant 2,6-diter-butyl-4-methylphenol (BHT) in DPPH and ABTS assays. To probe whether these HSB compounds may exert their antioxidant effect through transition metal ion chelation, the copper and ferrous chelating abilities of them were investigated. It was found by fluorescence quenching spectra that the binding constants K a were in the range of 0.85×103–7.30×104 M−1. Further study was carried out by the complexation of a representative compound 5 with ferrous ion in mass spectrum. A 2:1 5-ferrous complex was readily formed in a methanol–water solution (v:v, 8:2), which confirmed that the chelation happened when the HSB compounds were treated with transition metal ions. The above results indicated that the transition metal ion chelation play an important role in their antioxidant abilities.

Keywords

Hydroxyl Schiff base derivatives Antioxidants activity Transition metal ion chelation Radical scavenging activity 

Notes

Acknowledgments

This study was supported by the National Natural Science Foundation of China (No. 20762001), the Project of the Key Laboratory of Medicinal Chemical Resources and Molecular Engineering, Guangxi Normal University, China (No.0630006-5D09), and the Guangxi Department of Education research project (No. 200807MS075, 200807MS076, 200911MS281, 200911MS282).

References

  1. Eftink MR (1991) Fluorescence quenching reactions. In: Dewey TG (ed) Biophysical and biochemical aspects of fluorescence spectroscopy. Plenum Press, New York, pp 1–44Google Scholar
  2. Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine. Oxford University Press, OxfordGoogle Scholar
  3. Hipkiss AR (2005) Glycation, ageing and carnosine: are carnivorous diets beneficial. Mech Ageing Dev 126:1034–1039PubMedCrossRefGoogle Scholar
  4. Lakowica JR, Weber G (1973) Quenching of fluorescence by oxygen. A probe for structural fluctuations in macromolecules. Biochemistry 12:4161–4170CrossRefGoogle Scholar
  5. Lakowicz JR (1999) Principles of fluorescence spectroscopy. Plenum Press, New YorkGoogle Scholar
  6. Lee YL, Yen MT, Mau JL (2007) Antioxidant properties of various extracts from Hypizigus marmoreus. Food Chem 104:1–9CrossRefGoogle Scholar
  7. Maurice RE, Camillo AG (1981) Fluorescence quenching studies with proteins. Anal Biochem 114:199–212CrossRefGoogle Scholar
  8. Pan YM, Zhu JC, Wang HS, Zhang XP, Zhang Y, He CH, Ji XW, Li HY (2007) Antioxidant activity of ethanolic extract of Cortex fraxini and use in peanut oil. Food Chem 103:913–918CrossRefGoogle Scholar
  9. Pan YM, He CH, Wang HS, Ji XW, Wang K, Liu PZ (2010) Antioxidant activity of microwave-assisted extract of Buddleia officinalis and its major active component. Food Chem 121:497–502CrossRefGoogle Scholar
  10. Papadopoulou A, Green RJ, Frazier RA (2005) Interaction of flavonoids with bovine serum albumin: a fluorescene quenching study. J Agric Food Chem 53:158–163PubMedCrossRefGoogle Scholar
  11. Perez CA, Wei Y, Guo M (2009) Iron-binding and anti-Fenton properties of baicalein and baicalin. J Inorg Biochem 103:326–332PubMedCrossRefGoogle Scholar
  12. Tang YZ, Liu ZQ (2007) Free-radical-scavenging effect of carbazole derivatives on DPPH and ABTS radicals. Cell Biochem Funct 25:149–158PubMedCrossRefGoogle Scholar
  13. Wang HX, Tang YZ, Liu ZQ (2007) Ability of Schiff bases with hydroxyl-substituent to scavenge radicals. Chin J Synth Chem 24:1105–1108Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringSouth Central UniversityHunanPeople’s Republic of China
  2. 2.Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry & Chemical EngineeringGuangxi Normal UniversityGuilinPeople’s Republic of China
  3. 3.Department of Chemistry and Engineering TechnologyGuilin Normal CollegeGuilinPeople’s Republic of China

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