Browse > Article

Antioxidant Activity of Anthraquinones and Flavonoids from Flower of Reynoutria sachalinensis  

Zhang Xinfeng (College of Pharmacy, Chungnam National University)
Thuong Phuong Thien (College of Pharmacy, Chungnam National University)
Jin WenYi (College of Pharmacy, Chungnam National University)
Su Nguyen Duy (College of Pharmacy, Chungnam National University)
Sok Dai Eun (College of Pharmacy, Chungnam National University)
Bae KiHwan (College of Pharmacy, Chungnam National University)
Kang Sam Sik (National Products Research Institute, Seoul National University)
Publication Information
Archives of Pharmacal Research / v.28, no.1, 2005 , pp. 22-27 More about this Journal
Abstract
Bioassay-guided fractionation of methanol extract of Reynoutria 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-$\beta$-D-glucopyranoside (2), physcion-8-O-$\beta$-D­glucopyranoside (3), quercetin-3-O-$\alpha$-L-arabinofuranoside (4), quercetin-3-O-$\beta$-D-galactopyra­noside (5), and quercetin-3-O-$\beta$-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 $Cu^{2+}$-mediated low density lipoprotein (LDL) oxidation assay. The results demonstrated that three flavonoids, 4, 5, and 6 had remarkable antioxidant activities with the $IC_{50}$ values of 64.3, 54.7, and 46.2${\mu}M$ (DPPH scavenging), the $IC_{50}$ values of 6.0, 6.7, and $4.4{\mu}M$ (superoxide radical scavenging) and the $IC_{50}$ values of 3.8, 3.2, and 5.4${\mu}M$ against LDL oxidation, respectively.
Keywords
Reynoutria sachalinensis; Polygonaceae; Anthraquinones; Flavonoids; Antioxidant; DPPH; Superoxide radical; LDL oxidation;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 18  (Related Records In Web of Science)
Times Cited By SCOPUS : 24
연도 인용수 순위
1 Cohen, P. A. and Towers, G. H. N., The anthraquinones of Heterodermia obscurata. Phytochemistry, 40, 911-915 (1995)   DOI   ScienceOn
2 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)
3 Pharmacopia Commission of PRC, Pharmacopoeia of the Peoples Republic of China Vol. 1, 202, (1997)
4 Xiao, K., Xuan, L. J., and Xu, Y. M., Contituents from Polygonum cuspidatum. Chem. Pharm. Bull., 50, 605-608 (2002)   DOI   ScienceOn
5 Kerry, N. and Abbey, M., The isoflavone genistein inhibits copper and peroxyl radical mediated low density lipoprotein oxidation in vitro. Atherosclerosis, 140, 341-347 (1998)   DOI   ScienceOn
6 Hua, Y., Zhou, J. Y., Ni, W., and Chen, C. X., Studies on the constituents of Reynoutria japonica Houtt. Tianran Chanwu Yanjiu Yu Kaifa, 13, 16-18 (2001)
7 Bouktaib, M., Atmani, A., and Rolando, C., Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-${\beta}$-D-glucuronide. Tetrahedron Lett., 43, 6263- 6266 (2002)   DOI   ScienceOn
8 Paya, M., Halliwell, B., and Hoult, R. S., Interactions of a series of coumarins with reactive oxygen species. Biochem. Pharm., 44, 205-214 (1992)   DOI   ScienceOn
9 Bae, K., The Medicinal Plants of Korea, Kyo-Hak Publishing Co., Seoul, p. 98, (1999)
10 Kang, S. S. and Woo, W. S., Anthraquinones from the leaves of Polygonum sachalinense. Kor. J. Pharmacogn., 13, 7-9 (1982a)
11 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)   DOI   ScienceOn
12 Lusis, A. J., Atherosclerosis. Nature, 407, 233-241 (2000)   DOI   PUBMED   ScienceOn
13 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)   DOI   ScienceOn
14 Masaki, H., Sakaki, S., Atsumi, T., and Sakurai, H., Active oxygen scavenging activity of plant extracts. Biol. Pharm. Bull., 18, 162-166 (1995)   DOI   ScienceOn
15 Coskun, M., Satake, T., Hori, K., Saiki, Y., and Tanker, M., Anthraquinone glycoside from Rhamnus libanoticus. Phytochemistry, 29, 2018-2020 (1990)   DOI   ScienceOn
16 Kang, S. S. and Woo, W. S., A flavonoid glycoside from the leaves of Polygonum sachalinense (II). Arch. Pharm. Res., 5, 13-15 (1982b)   DOI   ScienceOn
17 Fuhrman, B. and Aviram, M., Flavonoids protect LDL from oxidation and attenuate atherosclerosis. Curr. Opi. Lipid, 12, 41-48 (2001)   DOI   ScienceOn
18 Wang, J. X., Wang, X. L., and Shi, J., Study on the chemical constituents of Pyrola atropurpurea. China Traditional and Herbal Drugs, 34, 113-115 (2003)
19 Wang, X. S., Greilberger J., Ledinski, G., Kager, G., Paigen, B., and Jurgens, G., The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL. Atherosclerosis, 172, 239-246 (2004)   DOI   ScienceOn
20 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)   DOI   ScienceOn
21 Xiang, L., Zheng, J. H., Guo, D. A., Kou, J. P., Fan, G. Q., Duan, Y. P., and Qin, C., Studies on anthraquinone constituents in Rheum sublanceolatum. China Traditional and Herbal Drugs, 32, 395-397 (2001)
22 Demirezer, L. O., KuruUzUm, A., Bergere, I., Schiewe, H. J., and Zeeck, A., The structures of antioxidant and cytotoxic agents from natural source: anthraquinones and tannins from roots of Rumex patientia. Phytochemistry, 58, 1213- 1217 (2001)   DOI   ScienceOn
23 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 of Polygonum Cuspidatum. J. Agric. Food Chem., 48 (2), 253-256 (2000)   DOI   ScienceOn
24 Andrew, J. B. and Edward, D. H., A quantitative test for copper using bicinchoninic acid. Analytical Biochemistry, 226, 80-84 (1995)   DOI   ScienceOn
25 Lu, Y. R. and Foo, L. Y., Identification and quantification of major polyphenols in apple pomace. Food Chemistry, 59, 187-194 (1997)   DOI   ScienceOn
26 Xiao, K., Xuan, L. J., and Xu, Y. M., Stilbene glycoside sulfates from Polygonum cuspidatum. J. Nat. Prod., 63, 1373 (2000)
27 Kang, S. S. and Woo, W. S., Flavonoids from the leaves of Polygonum sachalinense Fr. Schm. (I). Kor. J. Pharmacogn., 12, 208-210 (1981)
28 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)
29 Moon, J. H., Tsushida, T., Nakahara, K., and Terao, J., Identification of quercetin 3-O-${\beta}$-D-glucuronide as an antioxidative metabolite in rat plasma after oral anministration of quercetin. Free Radical Biology and Medicine, 30, 1274- 1285 (2001)   DOI   ScienceOn