Abstract
Biological activities of flavonoids have been extensively reviewed in literature. The biochemical profile of afzelin, kaempferitrin, and pterogynoside acting on reactive oxygen species was investigated in this paper. The flavonoids were able to act as scavengers of the superoxide anion, hypochlorous acid and taurine chloramine. Although flavonoids are naturally occurring substances in plants which antioxidant activities have been widely advertised as beneficial, afzelin, kaempferitrin, and pterogynoside were able to promote cytotoxic effect. In red blood cells this toxicity was enhanced, depending on flavonoids concentration, in the presence of hypochlorous acid, but reduced in the presence of 2,2′-azo-bis(2-amidinopropane) free radical. These flavonoids had also promoted the death of neutrophils, which was exacerbated when the oxidative burst was initiated by phorbol miristate acetate. Therefore, despite their well-known scavenging action toward free radicals and oxidants, these compounds could be very harmful to living organisms through their action over erythrocytes and neutrophils.
Similar content being viewed by others
References
Babior, B.M. 2000. Phagocytes and oxidative stress. American Journal of Medicine 109(1): 33–44.
Banerjee, A., A. Kunwar, B. Mishra, and K.I. Priyadarsini. 2008. Concentration dependent antioxidant/pro-oxidant activity of curcumin studies from AAPH induced hemolysis of RBCs. Chemico-Biological Interactions 174(2): 134–139.
Ben Sghaier, M., I. Skandrani, N. Nasr, M.G. Franca, L. Chekir-Ghedira, and K. Ghedira. 2011. Flavonoids and sesquiterpenes from Tecurium ramosissimum promote antiproliferation of human cancer cells and enhance antioxidant activity: A structure-activity relationship study. Environmental Toxicology and Pharmacology 32(3): 336–348.
Benedí, J., R. Arroyo, C. Romero, S. Martín-Aragón, and A.M. Villar. 2004. Antioxidant properties and protective effects of a standardized extract of Hypericum perforatum on hydrogen peroxide-induced oxidative damage in PC12 cells. Life Scences 75(10): 1263–1276.
Buonocore, G., S. Perrone, and M.L. Tataranno. 2010. Oxygen toxicity: Chemistry and biology of reactive oxygen species. Seminars in Fetal and Neonatal Medicine 15(4): 186–190.
Carvalho, P.R., D.H. Silva, V.S. Bolzani, and M. Furlan. 2005. Antioxidant quinonemethide triterpenes from Salacia campestris. Chemistry & Biodiversity 2(3): 367–372.
Castor, L.R., K.A. Locatelli, and V.F. Ximenes. 2010. Pro-oxidant activity of apocynin radical. Free Radical Biology and Medicine 48(12): 1636–1643.
Chan, T., G. Galati, and P.J. O’Brien. 1999. Oxygen activation during peroxidase catalysed metabolism of flavones or flavanones. Chemical-Biological Interactions 122(1): 15–25.
Cui, Y., D.S. Kim, and K.C. Park. 2005. Antioxidant effect of Inonotus obliquus. Journal of Ethnopharmacology 96(1–2): 79–85.
da Costa, M., V.F. Ximenes, and L.M. da Fonseca. 2004. Hypochlorous acid inhibition by acetoacetate: implications on neutrophil functions. Biological and Pharmaceutical Bulletin 27(8): 1183–1187.
Eaton, J.W. 1993. Defenses against hypochlorous acid: parrying the neutrophil's rapier thrust. Journal of Laboratory and Clinical Medicine 121(2): 197–208.
Galati, G., T. Chan, B. Wu, and P.J. O’Brien. 1999. Glutathione-dependent generation of reactive oxygen species by the peroxidase-catalyzed redox cycling of flavonoids. Chemical Research in Toxicology 12(6): 521–525.
Galati, G., M.Y. Moridani, T.S. Chan, and P.J. O’Brien. 2001. Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation. Free Radical Biology and Medicine 30(4): 370–382.
Halliwell, B., M. Wasil, and M. Grootveld. 1987. Biologically significant scavenging of the myeloperoxidase-derived oxidant hypochlorous acid by ascorbic acid. Implications for antioxidant protection in the inflamed rheumatoid joint. FEBS Letters 213(1): 15–17.
Hubinger, S.Z., L.C. Cefali, J.C.R. Vellosa, H.R.N. Salgado, V.L.B. Isaac, and R.R.D. Moreira. 2010. Dimorphandra mollis: Uma alternativa como fonte de flavonóides de ação antioxidante. Latin American Journal of Pharmacy 29(2): 161–320.
Kakkar, P., B. Das, and P.N. Viswanathan. 1984. A modified spectrophotometric assay of superoxide dismutase. Indian Journal of Biochemestry and Biophysics 21(2): 130–132.
Lapenna, D., and F. Cuccurullo. 1996. Hypochlorous acid and its pharmacological antagonism: an update picture. General Pharmacology 27(7): 1145–1147.
MacMicking, J., Q.W. Xie, and C. Nathan. 1997. Nitric oxide and macrophage function. Annual Review Immunology 15: 323–350.
Metodiewa, D., A. Kochman, and S. Karolczak. 1997. Evidence for antiradical and antioxidant properties of four biologically active N, N-diethylaminoethyl ethers of flavanone oximes: a comparison with natural polyphenolic flavonoid (rutin) action. Biochemestry and Molecular Biology International 41(5): 1067–1075.
Mian, M.F., C. Kang, S. Lee, J.H. Choi, S.S. Bae, S.H. Kim, Y.H. Kim, et al. 2008. Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis. Chemico-Biologycal Interactions 171(1): 57–66.
Pereira, A.M.S., A.H. Januário, M.E.E. Queiroz, R. Biondo, and S.C. França. 2005. Evaluation of Maytenus aquifolia Mart. and Maytenus ilicifolia Mart. chemotypes fortannins, total phenols and triterpenes. Revista Brasileira de Plantas Medicinais 8(1): 13–17.
Regasini, L.O., J.C. Vellosa, D.H. Silva, M. Furlan, O.M. de Oliveira, N.M. Khalil, I.L. Brunetti, M.C. Young, E.J. Barreiro, and V.S. Bolzani. 2008. Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors. Phytochemistry 69(8): 1739–1744.
Scott, M.D., J.J. van den Berg, T. Repka, P. Rouyer-Fessard, R.P. Hebbel, Y. Beuzard, and B.H. Lubin. 1993. Effect of excess alpha-hemoglobin chains on cellular and membrane oxidation in model beta-thalassemic erythrocytes. Journal of Clinical Investigation 91(4): 1706–1712.
Thomas, E.L., M.B. Grisham, and M.M. Jefferson. 1986. Preparation and characterization of chloramines. Methods in Enzymology 132: 569–585.
Vellosa, J.C.R., N.M. Khalil, V.O. Gutierres, V.A.F.F.M. dos Santos, M. Furlan, I.L. Brunetti, and O.M.M.F. Oliveira. 2007. Profile of Maytenus aquifolium action over free radicals and reactive oxygen species. Revista Brasileira de Ciências Farmacêuticas 43(3): 447–453.
Vellosa, J.C.R., N.M. Khalil, V.O. Gutierres, V.A.F.F.M. dos Santos, M. Furlan, I.L. Brunetti, and O.M.M.F. Oliveira. 2009. Salacia campestris root bark extract: Peroxidase inhibition, antioxidant and antiradical profile. Brazilian Journal of Pharmaceutical Sciences 45(1): 99–107.
Vellosa, J.C.R., L.O. Regasini, N.M. Khalil, V.S. Bolzani, O.A.K. Khalil, F.A. Manente, H.P. Netto, and O.M.M.F. Oliveira. 2011. Antioxidant and cytotoxic studies for kaempferol, quercetin and isoquercitrin. Eclética Química 36(2): 07–20.
Vissers, M.C., A.C. Carr, and A.L. Chapman. 1998. Comparison of human red cell lysis by hypochlorous and hypobromous acids: insights into the mechanism of lysis. Biochemical Journal 330(Pt 1): 131–138.
Weiss, S.J. 1989. Tissue destruction by neutrophils. The New England Journal of Medicine 320(6): 365–376.
Yang, H.L., S.C. Chen, N.W. Chang, J.M. Chang, M.L. Lee, P.C. Tsai, H.H. Fu, et al. 2006. Protection from oxidative damage using Bidens pilosa extracts in normal human erythrocytes. Food and Chemical Toxicology 44(9): 1513–1521.
Zhu, Q.Y., R.R. Holt, S.A. Lazarus, T.J. Orozco, and C.L. Keen. 2002. Inhibitory effects of cocoa flavanols and procyanidin oligomers on free radical-induced erythrocyte hemolysis. Experimental Biology and Medicine 227(5): 321–329.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Vellosa, J.C.R., Regasini, L.O., Belló, C. et al. Preliminary in vitro and ex vivo evaluation of afzelin, kaempferitrin and pterogynoside action over free radicals and reactive oxygen species. Arch. Pharm. Res. 38, 1168–1177 (2015). https://doi.org/10.1007/s12272-014-0487-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-014-0487-1