Inhibitory activity of flavonoids fromPrunus davidiana and other flavonoids on total ROS and hydroxyl radical generation
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Since reactive oxygen species (ROS) and hydroxyl radicals (OH) play an important role in the pathogenesis of many human degenerative diseases, much attention has focused on the development of safe and effective antioxidants. Preliminary experiments have revealed that the methanol (MeOH) extract of the stem ofPrunus davidiana exerts inhibitory/scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, total ROS and peroxynitrites (ONOO-). In the present study, the antioxidant activities of this MeOH extract and the organic solvent-soluble fractions, dichloromethane (CH2CI2), ethyl acetate (EtOAc), and n-butanol (n-BuOH), and the water layer ofP. davidiana stem were evaluated for the potential to inhibit OH and total ROS generation in kidney homogenates using 2′,7′-dichlorodihydrofluorescein diacetate (DCHF-DA), and for the potential to scavenge authentic ONOO-. We also evaluated the inhibitory activity of seven flavonoids isolated fromP. davidiana stem, kaempferol, kaempferol 7-O-β-D-glucoside, (+)-catechin, dihydrokaempferol, hesperetin 5-O-β-D-glucoside, naringenin and its 7-O-β-D-glucoside, on the total ROS, OH and ONOO- systems. For the further elucidation of the structure-inhibitory activity relationship of flavonoids on total ROS and OH generation, we measured the antioxidant activity of sixteen flavonoids available, including three active flavonoids isolated fromP. davidiana, on the total ROS and OH systems. We found that the inhibitory activity on total ROS generation increases in strength with more numerous hydroxyl groups on their structures. Also, the presence of anortho-hydroxyl group, whether on the A-ring or B-ring, and a 3-hydroxyl group on the C-ring increased the inhibitory activity on both total ROS and OH generation.
Key wordsPrunus davidiana Antioxidant activity Total reactive oxygen species (ROS) Peroxynitrite (ONOO-) Hydroxyl radical (OH) Flavonoids
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- Choi, J. S., Chung, H. Y, Kang, S. S., Jung, M. J., Kim, J. W., No, J. K. and Jung, H. A., The structure-activity relationship of flavonoids as scavengers of peroxynitrite.Phytochem. Res., 16, 232–235 (2002).Google Scholar
- Choi, J. S., Young, H. S., Lee, T. W., Woo, W. S., and Lee, E. B., Chemistry and anti-inflammatory activity ofPrunus davidiana stems.Yakhak Hoeji, 36, 115–119 (1992).Google Scholar
- Choi, J. S., Lee, H. J., Park, H. J., and Kim, H. G., Screening of plants and marine algae and its active principles fromPrunus davidiana.Kor. J. Pharmacogn., 24, 299–303 (1993).Google Scholar
- Cos, P., Ying, L, Calomme, M., Hu, J. P., Cimanga, K., Poel, B. V., Pieters, L., Vlietinck, A. J., and Berghe, D., Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.J. Nat. Prod., 61, 71–76 (1998).PubMedCrossRefGoogle Scholar
- Lee, W. R., Shen, S. C., Lin, H. Y., Hou, W. C., Yang, L. L., and Chen, Y C., Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca2+-dependent endonuclease.Biochem. Pharmacol., 63, 225–236 (2002).PubMedCrossRefGoogle Scholar
- Morel, I., Lescoat, G., Cognel, P., Sergent, O., Pasdelop, N., Brissot, P., Cillard, P., and Cillard, J., Antioxidant and iron-chelating activities of the flavonoids, catechin, quercetin and diosmetin, on iron-loaded rat hepatocyte cultures.Biochem. Pharmacol., 45, 13–19 (1993).PubMedCrossRefGoogle Scholar
- Pincemail, J. J., Free radicals and antioxidants in human diseases. In Favier, A. E., Cadet, J., Kalyanaraman, B., Fontecave, M., and Pierre, J.-L.,Analysis of Free radicals in Biological Systems. Birkhauser Verlag, Berlin, pp. 83–98, (1995).Google Scholar
- Singh, A., Chemical and biochemical aspects of activated oxygen: singlet oxygen, superoxide anion, and related species, In Miquel, J., Quintanilha, A. T, and Weber, H. (Eds).CRC Handbook of free radicals and antioxidants in Biomedicine. CRC Press, Inc., Boca Raton, Florida, Vol. 1, pp. 17–28, (1989).Google Scholar