Abstract
In the course of the investigations of natural antioxidants, we examined the antioxidant activities of the methanol (MeOH) extracts of some selectedPrunus species, includingP. buergeriana, P. davidiana, P. padus, P. pendula for.ascendens, P. sargentii, P. serrulata var. spontanea andP. yedoensis by three methods as represented by the 1,1-diphenyl-2-picrylhy-drazyl (DPPH) radical, total ROS (reactive oxygen species) and the peroxynitrite (ONOO-) scavenging activity tests. We also evaluated the activities of the organic solvent-soluble fractions, including the dichloromethane (CH2CI2), ethyl acetate (EtOAc),n-butanol (n-BuOH) fractions and the water (H2O) layer ofP. serrulata var.spontanea leaves. By means of bioassay-directed fractionation, we isolated eleven known flavonoids (1–11) from the EtOAc soluble fraction of the MeOH extract of thePrunus serrulata var.spontanea leaves, exhibiting strong antioxidant activity and characterized as prunetin (1), genistein (2), quercetin (3), prunetin 4′-O-β-glucopyranoside (4), kaempferol 3-O-β-arabinofuranoside (5), prunetin 5-O-β-glucopyranoside (6), kaempferol 3-O-β-xylopyranoside (7), genistin (8), kaempferol 3-O-β-glucopyranoside (9), quercetin 3-O-β-glucopyranoside (10) and kaempferol 3-O-β-xylopyranosyl-(1→2)-β-glucopyr-anoside (11). Compounds3 and10 showed good activities in all tested model systems. Compounds2 and8 showed scavenging activities in the DPPH and ONOCr tests, while compounds5,7,9 and11 were active in the ONOO- and ROS tests. On the other hand, compounds1,4 and6 did not show any activities in the tested model systems.
Similar content being viewed by others
References
Agrawal, P. K., NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.Phytochem., 31, 3307–3330 (1992).
Ames, B. N., Shigenaga, M. K., and Hage, T. M., Oxidants, antioxidants and the degenerative diseases of aging.Proc. Natl. Acad. Sci. USA, 90, 7915–7922 (1993).
Aruoma, O. I., Assessment of potential prooxidant and antioxidant actions.J. Am. Oil Chem. Soc., 73 (12), 1617–1625 (1996).
Balavoine G. G. and Genleti, Y. V., Peroxynitrite scavenging by different antioxidants, Part I: convenient assay.Nitric Oxide, 3, 40–54 (1999).
Beckman, J. S., Beckman, T. W., Chen, J., Marshell, P. A., and Freeman, B. A., Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide.Proc. Natl. Acad. Sci., USA, 87, 1620–1624 (1990).
Beninger, C. W., Hosfield, G. L. and Nair, M. G., Flavonol glycosides from the seed coat of a new manteca-type dry bean (Phaseolus vulgaris L).J. Agric. Food Chem., 46, 2906–2910 (1998).
Blois, M. S., Antioxidant determination by the use of a stable free radical.Nature, 181, 1199–1202 (1958).
Branen, A. L., Toxicology and biochemistry of butylated hydr-oxyanisole and butylated hydroxytoluene.J. Am. Oil Chem. Soc., 52, 59–63 (1975).
Choi, H. R., Choi, J. S., Han, Y. N., Bae, S. J., and Chung, H. Y., Peroxynitrite scavenging activity of herb extracts.Phytother. Res., 16, 364–367 (2002).
De Almeida, A. P., Miranda, M. M. F. S., Simoni, I. C., Wigg, M. D., Lagrota, M. H. C., and Costa, S. S., Flavonol monoglyco-sides isolated from the antiviral fractions o.Persea Americana (Lauraceae) leaf infusion.Phytother. Res., 12, 562–567 (1998).
Donovan, J. L., Meyer, A. S., and Waterhouse, A. L., Phenolic composition and antioxidant activity of prunes and prunes juice (Prunus domestica).J. Agric. Food Chem., 46, 1247–1252 (1998).
Dreher, D. and Junod, F., Role of oxygen free radicals in cancer development.Eur. J. Cancer, 32A(1), 30–38 (1996).
Farkas, L., Nogradi, M., Antus, S., and Gottsegen, A., About the existence of padmakastein and padmakastin.Tetrahedron, 25, 1013–1019 (1969).
Geibel, M. and Feucht, W., Flavonoid 5-glucosides fro.Prunus cerasus bark and their characteristic weak glucosidic bonding.Phytochem., 30, 1519–1521 (1991).
Geibel, M., Geiger, H., and Treuter, D., Tectochrysn 5- and geni-stein 5-glucosides from the bark o.Prunus cerasus.Phytochem., 29, 1351–1353 (1990).
Griffiths, H. R. and Lunec, J., The C1q binding activity of IgG is modified in vitro by reactive oxygen species: implications for rhematinoid arthritis.FEBS Lett., 388, 161–164 (1996).
Jung, H. A., Park, J. C., Chung, H. Y., Kim, J., and Choi, J. S., Antioxidant flavonoids and chlorogenic acid from the leaves ofEriobotrya japonica.Arch. Pharmacol. Res., 22, 213–218, (1999).
Kayano, S.-I., Kikuzaki, H., Fukutsuka, N., Mitani, T., and Nakatani, N., Antioxidant activity of prune (Prunus domestica L.) constituents and a new synergist.J. Agric. Food Chem., ASAP., Accepted April 10 (2002).
Khalid, S. A., Gellert, M., Szendrei, K., and Duddeck, H., Prunetin 5-O-β-D-glucopyranoside, an isoflavone from the peduncle ofPrunus avium andP. cerasus.Phytochem., 28 (5), 1560–1561 (1989).
Kim, H. J., Woo, E. R., and Park, H. K., A novel lignan and flavonoids fro.Polygonum aviculare.J. Nat. Prod., 57, 581–586 (1994).
Kim, J. G.,Illustrated Natural Drugs Encyclopedia (color edition), Namsandang, Korea, Vol. I, pp. 437, (1997).
Kim, T. J., InKorean Resources Plants, Seoul National University Publisher, Seoul, Korea, Vol. II, pp. 171, (1996).
Kooy, N. W., Royall, J. A., Ischiropoulos, H., and Beckman, J. S., Peroxynitrite-mediated oxidation of dihydrorhodamine 123.Free Radic. Biol. Med., 16, 149–156 (1994).
Kritikar, K. R. and Basu, B. D., InIndian Medicinal Plants, M/S Periodical Experts, New Delhi, Vol. II, pp. 951, (1974).
Label, C. P. and Bondy, S. C., Sensitive and rapid quantitation of oxygen reactive species formation in rat synaptosomes.Neurochem. Int., 17, 435–441 (1990).
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 catechins, quercetin and diosmetin on iron-loaded rat hepatocyte cultures.Biochem. Pharmacol., 45, 13–19 (1993).
Nakatani, N., Kayano, S.-I., Kikuzaki, H., Sumino, K., Katagiri, K., and Mitani, T., Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L).J. Agric. Food Chem., 48, 5512–5516 (2000).
Oshima, H., Yoshie, Y., Auriol, S., and Gillbert, I., Antioxidant and pro-oxidant actions of flavonoids: Effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion.Free Radic. Biol. Med., 25, 1057–1065 (1998).
Park, H. J., Young, H. S., Park, K. Y., Rhee, S. H., Chung, H. Y., and Choi, J. S., Flavonoids from the whole plants o.Orosta-chysjaponicus.Arch. Pharm. Res., 14, 167–171 (1991).
Pincemail, J. J., Free radicals and antioxidants in human diseases. In Favier, A. E., Cadet, J., Kalyanaraman, B., Fontecave, M., Pierre, J.-L.,Analysis of Free radicals in Biological Systems. Birkhauser Verlag, Berlin, pp. 83–98, (1995).
Rice-Evans, C. A., Miller, N., and Paganga, G., Structure-anti-oxidant activity relationships of flavonoids and phenolic acids.Free Radic. Biol. Med., 20, 933–956 (1996).
Sagar, S., Kallo, I. J., Kaul, N., Ganguly, N. K. and Sharma, B. K., Oxygen free radicals in essential hypertension.Mol. Cell Biochem., 111, 103–108 (1992).
Salah, N., Miller, N. J., Paganga, G., Tijburg, L., Bolwell, G. P. and Rice-Evans, C. A., Polyphenols flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants.Arch. Biochem. Biophys., 322, 339–346 (1995).
Sang, S., Lapsley, K., Jeong, W.-S., Lachance, P. A. Ho, C.-T., and Rosen, R. T., Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch).J. Agric. Food Chem., 50, 2459–2463 (2002).
Sawa, T., Akaike, T., and Maeda, H., Tyrosine nitration by peroxynitrite formed nitric oxide and superoxide generated by xanthine oxidase.J. Biol. Chem., 275 (42), 32467–32474 (2000).
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).
Sohal, R. S., Role of oxidative stress and protein oxidation in the aging process.Free Radic. Biol. Med., 33 (1), 37–44 (2002).
Squadrito, G. L. and Pryor, W. A., Oxidative chemistry of nitric oxide: the role of superoxide, peroxynitrite, and carbon dioxide.Free Radic. Biol. Med., 25, 392–403 (1998).
Talukadar, A. C., Jain, N., De, S., Krishnamurty, H. G., An isoflavone fro.Myristica malabarica, Phytochem., 53, 155–157 (2000).
Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M., and Gray, J. I., Antioxidant polyphenols from tart cherries (Prunus cerasus).J. Agric. Food Chem., 47, 840–844 (1999a).
Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M. and Gray, J. I., Novel antioxidant compounds from tart cherries (Prunus cerasus).J. Nat. Prod., 62, 86–88 (1999b).
Young, H. S., Park, J. C., Park, H. J., Lee, J. H., and Choi, J. S., Phenolic compounds of the leaves o.Eucommia ulmoides.Arch. Pharm. Res., 14 (2), 114–117 (1991).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jung, H.A., Kim, A.R., Chung, H.Y. et al. In vitro antioxidant activity of some selectedprunus species in Korea. Arch Pharm Res 25, 865–872 (2002). https://doi.org/10.1007/BF02977006
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02977006