Browse > Article
http://dx.doi.org/10.4062/biomolther.2010.18.2.191

Antioxidant Flavonoids from the Twigs of Stewartia koreana  

Lee, Sa-Im (College of Pharmacy, Kyung Hee University)
Yang, Jae-Heon (College of Pharmacy, Woosuk University)
Kim, Dae-Keun (College of Pharmacy, Woosuk University)
Publication Information
Biomolecules & Therapeutics / v.18, no.2, 2010 , pp. 191-196 More about this Journal
Abstract
In the course of screening for antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl- 2-picrylhydrazyl (DPPH), a total extract of the twigs of Stewartia koreana (Theaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of six phenolic compounds, ampelopsin (1), catechin (2), proanthocyanidin-A2 (3), fraxin (4), (2R, 3R)-taxifolin-3-${\beta}$-D-glucopyranoside (5), and (2S, 3S)-taxifolin-3-${\beta}$-D-glucopyranoside (6), as active principles. Their structures were elucidated by spectroscopic studies. Compounds 1-6 were isolated for the first time from this plant. Among them, three compounds 1-3 showed the significant antioxidative effects on DPPH, and riboflavin originated superoxide quenching activity. In riboflavin-nitrobluetetrazolium (NBT)-light system, compound 1 showed better superoxide quenching activity than vitamin C.
Keywords
Stewartia koreana; Theaceae; Phenolic compounds; DPPH; Superoxide quenching activity;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 3
연도 인용수 순위
1 Branen, A. L. (1975). Toxicology and biochemistry of butylated hydroxyanisole and butylated hydroxytoluene. J. Am. Oil. Chem. Soc. 52, 59-63.   DOI
2 Choi, D. S., Kim, S. J. and Jung, M. Y. (2001). Inhibitory activity of berberine on DNA strand cleavage induced by hydrogen peroxide and cytochrome c. Biosci. Biotechnol. Biochem. 65, 452-455.   DOI
3 Dembinska-Kiec, A., Mykkänen, O., Kiec-Wilk, B. and Mykkanen, H. (2008). Antioxidant phytochemicals against type 2 diabetes. Br. J. Nutr. 99 (E Suppl 1), ES 109-117.
4 Ginnopolitis, C. N. and Ries, S. K. (1977). Superoxide dismutase. I. Occurrence in higher plants. Plant Physiol. 59, 309-314.   DOI
5 Ma, Y. Q., Ye, X. Q., Fang, Z. X., Chen, J. C., Xu, G. H. and Liu, D. H. (2008). Phenolic compounds and antioxidant activity of extracts from ultrasonic treatment of Satsuma Mandarin (Citrus unshiu Marc.) peels. J. Agric. Food Chem. 56, 5682-5690.   DOI
6 Kim, Y., Min, H. Y., Park, H. J., Lee, E. J., Park, E. J., Hwang, H. J., Jin, C., Lee, Y. S. and Lee, S. K. (2004). Suppressive effects of nitric oxide production and inducible nitric oxide synthase (iNOS) gene expression by Calystegia soldanella methanol extract on lipopolysaccharide-activated RAW 264.7 cells. Eur. J. Cancer Prev. 13, 419-424.   DOI
7 Liu, F. and Ng, T. B. (2000). Antioxidative and free radical scavenging activities of selected medicinal herbs. Life Sciences 66, 725-735.   DOI
8 Lee, T. H., Kwak, H. B., Kim, Kim H. H., Lee, Z. H., Chung, D. K., Baek, N. I. and Kim, J. (2007). Methanol extracts of Stewartia koreana inhibit cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) gene expression by blocking $NF-{\kappa}B$ transactivation in LPS-activated RAW 264.7 cells. Mol. Cells 23, 398-404.
9 Lee, T. H., Lee, G. W., Kim, C. W., Bang, M. H., Baek, N. I., Kim, S. H., Chung, D. K. and Kim, J. (2010). Stewartia koreana extract stimulates proliferation and migration of human endothelial cells and induces neovasculization in vivo. Phytother. Res. 24, 20-25.   DOI
10 Li, D. L., Li, X. M., Peng, Z. Y. and Wang, B. G. (2007). Flavanol derivatives from Rhizophora stylosa and their DPPH radical scavenging activity. Molecules 12, 1163-1169.   DOI
11 Luo, G. Q., Zeng, S. and Liu, D. Y. (2006). Inhibitory effects of ampelopsin on angiogenesis. Zhong Yao Cai 29, 146-150.
12 Shi, S. H., Chen, H. H. and Kong, L. Y. (2007). Studies on chemical constituents in Chrozophora sabulosa Kar. Chin. Pharm. J. 252-255.
13 Yoshida, T., Mori, K., Hatano, T., Okumura, T., Uehara, L., Komagoe, K., Fujita, Y. and Okuda, T. (1989). Studies on inhibition mechanism of autooxidation by tannins and flavonoids. V. Radical scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37, 1919-1921.   DOI
14 Moure, A., Cruz, J. M., Franco, D., Dominguez, J. M., Sineiro, J., Dominguez, H., Nunez, M. J. and Parajo, J. C. (2001). Natural antioxidants from residual sources. Food Chemistry 72, 145-171.   DOI
15 Murakami, T., Miyakoshi, M., Araho, D., Mizutani, K., Kambara, T., Ikeda, T., Chou, W. H., Inukai, M., Takenaka, A. and Igarashi, K. (2004). Hepatoprotective activity of tocha, the stems and leaves of Ampelopsis grossedentata, and ampelopsin. Biofactors 21, 175-178.   DOI
16 Park, C. K., Kim, H. J., Kwak, H. B., Lee, T. H., Bang, M. H., Kim, C. M., Lee, Y., Chung, D. K., Baek, N. I., Kim, J., Lee, Z. H. and Kim, H. H. (2007). Inhibitory effects of Stewartia koreana on osteoclast differentiation and bone resorption. Int. Immunopharmacol. 7, 1507-1516.   DOI
17 Sakushima, A., Ohno, K., Coskun, M., Seki, K. I. and Ohkura, K. (2002). Separation and identification of taxifolin-3-O-glucoside isomers from Chamaecyparis obtusa (Cupressaceae). Nat. Prod. Lett. 16, 383-387.   DOI
18 Xia, L. (1995). Studies on the chemical constituents of Agrimonia pilosa Ledeb. J. Beijing Med. Univ. 27, 60-61.
19 Ye, J., Guan, Y., Zeng, S. and Liu, D. (2008). Ampelopsin prevents apoptosis induced by $H_2O_2$ in MT-4 lymphocytes. Planta Med. 74, 252-257.   DOI
20 Yeo, H. S., Park, J. C. and Choi, J. S. (1992). Phytochemical studies on the constituents of Filipendula glaberrima. Kor. J. Pharmacogn. 23, 121-125.   과학기술학회마을
21 Jacques, D. and Haslam, E. (1974). Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives. J. Chem. Soc. Perkin Trans. 1, 2663-2671.
22 Yeom, S. H., Kim, M. K., Kim, H. J., Shim, J. G., Lee, J. H. and Lee, M. W. (2003). Phenolic compounds from seeds of Astragalus sinicus and its antioxidative activities. Kor. J. Pharmacogn. 34, 344-351.   과학기술학회마을
23 Zeng, S., Liu, D., Ye, Y., Wang, L. and Wang, W. (2004). Anti-tumor effects of ampelopsin on human lung cancer GLC-82 implanted in nude mice. Zhong Yao Cai 27, 842-845.