Abstract
Bioassay-guided fractionation of methanol extract ofReynoutria sachalinensis flower using DPPH assay has led to the isolation of three anthraquinones and three flavonoids. Their structures were identified as emodin (1), emodin-8-O-β-D-glucopyranoside (2), physcion-8-O-β-D-glucopyranoside (3), quercetin-3-O-α-L-arabinofuranoside (4), quercetin-3-O-α-D-galactopyranoside (5), and quercetin-3-O-β-D-glucuronopyranoside (6) by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for antioxidant activities with free radical 1, 1-diphenyl-2-picrylhydrazyl (DPPH) scavenging, superoxide radical scavenging and Cu2+-mediated low density lipoprotein (LDL) oxidation assay. The results demonstrated that three flavonoids,4, 5, and6 had remarkable antioxidant activities with the IC50 values of 64.3, 54.7, and 46.2 μM (DPPH scavenging), the IC50 values of 6.0, 6.7, and 4.4 μM (superoxide radical scavenging) and the IC50 values of 3.8, 3.2, and 5.4 μM against LDL oxidation, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Andrew, J. B., and Edward, D. H., A quantitative test for copper using bicinchoninic acid.Analytical Biochemistry, 226, 80–84 (1995).
Bae, K., The Medicinal Plants of Korea, Kyo-Hak Publishing Co., Seoul, p. 98, (1999).
Bouktaib, M., Atmani, A., and Rolando, C., Regio- and stereo-selective synthesis of the major metabolite of quercetin, quercetin-3-O-β-D-glucuronide.Tetrahedron Lett., 43, 6263–6266 (2002).
Cohen, P. A. and Towers, G. H. N., The anthraquinones ofHeterodermia obscurata.Phytochemistry, 40, 911–915 (1995).
Coskun, M., Satake, T., Hori, K., Saiki, Y., and Tanker, M., Anthraquinone glycoside fromRhamnus libanoticus.Phytochemistry, 29, 2018–2020 (1990).
Demirezer, L. Ö., KuruÜzÜm, A., Bergere, I., Schiewe, H. J., and Zeeck, A., The structures of antioxidant and cytotoxic agents from natural source: anthraquinones and tannins from roots ofRumex patientia.Phytochemistry, 58, 1213–1217 (2001).
Diaz, M. N., Frei, B., Vita, J. A., and Keaney, J. F., Antioxidants and atherosclerotic heart disease.N. Engl. J. Med., 337, 408–416 (1997).
Fuhrman, B. and Aviram, M., Flavonoids protect LDL from oxidation and attenuate atherosclerosis.Curr. Opi. Lipid, 12, 41–48 (2001).
Hou, L. F., Zhou, B., Yang, L., and Liu, Z. L., Inhibition of human low density lipoprotein oxidation by flavonols and their glycosides.Chemistry and Physics of Lipids, 129, 209–219 (2004).
Hua, Y., Zhou, J. Y., Ni, W., and Chen, C. X., Studies on the constituents ofReynoutria japonica Houtt.Tianran Chanwu Yanjiu Yu Kaifa, 13, 16–18 (2001).
Kang, S. S. and Woo, W. S., Anthraquinones from the leaves ofPolygonum sachalinense.Kor. J. Pharmacogn., 13, 7–9 (1982a).
Kang, S. S. and Woo, W. S., Flavonoids from the leaves ofPolygonum sachalinense Fr. Schm. (I).Kor. J. Pharmacogn., 12, 208–210 (1981).
Kang, S. S. and Woo, W. S., A flavonoid glycoside from the leaves ofPolygonum sachalinense (II).Arch. Pharm. Res., 5, 13–15 (1982b).
Kerry, N. and Abbey, M., The isoflavone genistein inhibits copper and peroxyl radical mediated low density lipoprotein oxidationin vitro.Atherosclerosis, 140, 341–347 (1998).
Li, J. L., Wang, A. Q., Li, J. S., He, W. Y., and Kong, M., Anthraquinones of Hotao Rhubarb (Pheum hotaoense).China Traditional and Herbal Drugs, 31, 321–324 (2000).
Lu, Y. R. and Foo, L. Y., Identification and quantification of major polyphenols in apple pomace.Food Chemistry, 59, 187–194 (1997).
Lusis, A. J., Atherosclerosis.Nature, 407, 233–241 (2000).
Masaki, H., Sakaki, S., Atsumi, T., and Sakurai, H., Active oxygen scavenging activity of plant extracts.Biol. Pharm. Bull., 18, 162–166 (1995).
Moon, J. H., Tsushida, T., Nakahara, K., and Terao, J., Identification of quercetin 3-O-β-D-glucuronide as an anti-oxidative metabolite in rat plasma after oral anministration of quercetin.Free Radical Biology and Medicine, 30, 1274–1285 (2001).
Na, M. K., An, R. B., Jin, W. Y., Min, B. S., Yoo, J. K., Kim, Y. H., and Bae, K., Antioxidant effects of plant extracts on free radicals and lipid peroxidation.Nat. Prod. Sci., 9, 226–231 (2003).
Paya, M., Halliwell, B., and Hoult, R. S., Interactions of a series of coumarins with reactive oxygen species.Biochem. Pharm., 44, 205–214 (1992).
Pharmacopia Commission of PRC, Pharmacopoeia of the Peoples Republic of China Vol. 1, 202, (1997).
Price, K. R., Colquhoun, I. J., Barnes, K. A., and Rhodes, M. J. C., Composition and content of flavonol glycosides in green beans and their fate during processing.J. Agric. Food Chem., 46, 4898–4903 (1998).
Vastano, B. C., Chen, Y., Zhu, N. Q., Ho, C. T., Zhou, Z. Y., and Rosen, R. T., Isolation and identification of stilbenes in two varieties ofPolygonum Cuspidatum.J. Agric. Food Chem., 48 (2), 253–256 (2000).
Wang, X. S., Greilberger J., Ledinski, G., Kager, G., Paigen, B., and Jurgens, G., The hypolipidemic natural productCommiphora mukul and its component guggulsterone inhibit oxidative modification of LDL.Atherosclerosis, 172, 239–246 (2004).
Wang, J. X., Wang, X. L., and Shi, J., Study on the chemical constituents ofPyrola atropurpurea.China Traditional and Herbal Drugs, 34, 113–115 (2003).
Xiang, L., Zheng, J. H., Guo, D. A., Kou, J. P., Fan, G. Q., Duan, Y. P., and Qin, C., Studies on anthraquinone constituents inRheum sublanceolatum.China Traditional and Herbal Drugs, 32, 395–397 (2001).
Xiao, K., Xuan, L. J., and Xu, Y. M., Contituents fromPolygonum cuspidatum.Chem. Pharm. Bull., 50, 605–608 (2002).
Xiao, K., Xuan, L. J., and Xu, Y. M., Stilbene glycoside sulfates fromPolygonum cuspidatum.J. Nat. Prod., 63, 1373 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhang, X., Thuong, P.T., Jin, W. et al. Antioxidant Activity of Anthraquinones and Flavonoids from Flower ofReynoutria sachalinensis . Arch Pharm Res 28, 22–27 (2005). https://doi.org/10.1007/BF02975130
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02975130