Planta Med 2001; 67(6): 515-519
DOI: 10.1055/s-2001-16472
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

Cytotoxicity and Lipid Peroxidation-Inhibiting Activity of Flavonoids

Paul Cos, Mario Calomme, Jean-Bosco Sindambiwe, Tess De Bruyne, Kanyanga Cimanga, Luc Pieters, Arnold J. Vlietinck, Dirk Vanden Berghe
  • Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
Further Information

Publication History

August 18, 2000

November 5, 2000

Publication Date:
17 August 2001 (online)

Abstract

Thirty-five flavonoids of seven different types, namely isoflavonoids, chalcones, dihydroflavonols, flavanols, flavanones, flavones, and flavonols were investigated for their ability to inhibit ascorbate-induced microsomal lipid peroxidation and their cytotoxicity. For each activity a structure-activity relationship was established. Subsequently, an antioxidant selectivity index, i. e., the maximal non-toxic dose divided by the IC50 value for lipid peroxidation, was introduced. Kaempferol showed the highest antioxidant selectivity index of all flavonoids tested.

References

  • 1 King A, Young G. Characteristics and occurrence of phenolic phytochemicals.  Journal of the American Dietetic Association. 1999;  99 213-8
  • 2 Diplock A T, Charleux J -L, Crozier-Willi G, Kok F J, Rice-Evans C, Roberfroid M, Stahl W, Vina-Ribes J. Functional food science and defence against reactive oxygen species.  British Journal of Nutrition. 1998;  80 S77-112
  • 3 Steinmetz K A, Potter J D. Vegetables, fruits, and cancer. I.  Epidemiology.. Cancer Causes and Control. 1991;  2 325-57
  • 4 Hertog M G, Bueno-de-Mesquita H B, Fehily A M, Sweetnam P M, Elwood P C, Kromhout D. Fruit and vegetable consumption and cancer mortality in the Caerphilly study, Cancer Epidemiology, Biomarkers and Prevention.  1996;  5 673-7
  • 5 Bravo L. Polyphenols : Chemistry, dietary sources, metabolism, and nutritional significance.  Nutrition Reviews. 1998;  56 (11) 317-33
  • 6 Croft K D. The chemistry and biological effects of flavonoids and phenolic acids.  Annals New York Academy of Sciences. 1998;  854 435-42
  • 7 Hertog M G, Hollman P C, Katan M B, Kromhout D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands.  Nutrition and Cancer. 1993;  20 21-9
  • 8 Mylonas C, Kouretas D. Lipid peroxidation and tissue damage.  In Vivo. 1999;  13 295-310
  • 9 Laughton M J, Halliwell B, Evans P J, Hoult J RS. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin.  Biochemical Pharmacology. 1989;  38 2859-65
  • 10 Sanz M J, Ferrandiz M L, Cejudo M, Terencio M C, Gil B, Bustos G, Ubeda A, Gunasegaran R, Alcaraz M J. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress.  Xenobiotica. 1994;  24 689-99
  • 11 Moran J F, Klucas R V, Grayer R J, Abian J, Becana M. Complexes of iron with phenolic compounds from soybean nodules and other legume tissues: Prooxidant and antioxidant properties.  Free Radical Biology & Medicine. 1997;  22 861-70
  • 12 Ernster L, Nordenbrand K. In: Estabrook RW, Pullman ME, editors Methods in Enzymology. Vol. 10 New York; Academic Press 1967: 574-80
  • 13 Bradford M M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.  Analytical Biochemistry. 1976;  72 248-54
  • 14 Duniec Z, Robak J, Gryglewski R. Antioxidant properties of some chemicals vs their influence on cyclooxygenase and lipoxidase activities.  Biochemical Pharmacology. 1983;  32 2283-6
  • 15 Mosmann T. Rapid colorimetric assay for cellular growth and survival.  Journal of Immunological Methods. 1983;  65 55-63
  • 16 Rice-Evans C A, Miller N J, Paganga G. Structure-antioxidant relationships of flavonoids and phenolic acids.  Free Radical Biology & Medicine. 1996;  20 933-56
  • 17 Cos P, Calomme M, Pieters L, Vlietinck A J, Vanden Berghe D. Structure-activity relationship of flavonoids as antioxidant and pro-oxidant compounds. In: Atta-ur-Rahman, editor Studies in Natural Products Chemistry. Vol 22 Amsterdam; Elsevier Science Publishers 2000: 307-41
  • 18 Zucco F, De Angelis I, Stammati A. Cellular models for in vitro toxicity testing. In: Clynes M, editor Animal Cell Culture Techniques Berlin; Springer-Verlag 1998: 395-422

Prof. Dr. D. Vanden Berghe

Department of Pharmaceutical Sciences

University of Antwerp

Universiteitsplein 1

2610 Antwerp

Belgium

Email: microfar@uia.ua.ac.be

Fax: (32) 3 820 25 44