DOI QR코드

DOI QR Code

Antioxidant Flavonoids from the Twigs of Stewartia koreana

  • Received : 2010.01.30
  • Accepted : 2010.04.07
  • Published : 2010.04.30

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

References

  1. Branen, A. L. (1975). Toxicology and biochemistry of butylated hydroxyanisole and butylated hydroxytoluene. J. Am. Oil. Chem. Soc. 52, 59-63. https://doi.org/10.1007/BF02901825
  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. https://doi.org/10.1271/bbb.65.452
  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. https://doi.org/10.1104/pp.59.2.309
  5. Jacques, D. and Haslam, E. (1974). Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives. J. Chem. Soc. Perkin Trans. 1, 2663-2671.
  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. https://doi.org/10.1097/00008469-200410000-00010
  7. 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.
  8. 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. https://doi.org/10.1002/ptr.2851
  9. 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. https://doi.org/10.3390/12051163
  10. Liu, F. and Ng, T. B. (2000). Antioxidative and free radical scavenging activities of selected medicinal herbs. Life Sciences 66, 725-735. https://doi.org/10.1016/S0024-3205(99)00643-8
  11. Luo, G. Q., Zeng, S. and Liu, D. Y. (2006). Inhibitory effects of ampelopsin on angiogenesis. Zhong Yao Cai 29, 146-150.
  12. 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. https://doi.org/10.1021/jf072474o
  13. 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. https://doi.org/10.1016/S0308-8146(00)00223-5
  14. 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. https://doi.org/10.1002/biof.552210136
  15. 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. https://doi.org/10.1016/j.intimp.2007.07.016
  16. 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. https://doi.org/10.1080/10575630290033141
  17. Shi, S. H., Chen, H. H. and Kong, L. Y. (2007). Studies on chemical constituents in Chrozophora sabulosa Kar. Chin. Pharm. J. 252-255.
  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. https://doi.org/10.1055/s-2008-1034317
  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.
  21. 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.
  22. 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. https://doi.org/10.1248/cpb.37.1919
  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.

Cited by

  1. Phenolic Compounds from the Leaves of Stewartia pseudocamellia Maxim. and their Whitening Activities vol.23, pp.3, 2015, https://doi.org/10.4062/biomolther.2014.140
  2. Anti-inflammatory activity of sulfate-containing phenolic compounds isolated from the leaves of Myrica rubra vol.92, 2014, https://doi.org/10.1016/j.fitote.2013.10.007
  3. The comparison of DPPH-scavenging capacity and anti-inflammatory effects of phenolic compounds isolated from the stems ofStewartia koreanaNakai vol.28, pp.17, 2014, https://doi.org/10.1080/14786419.2014.905560
  4. Phenylacylphenol derivatives with anti-melanogenic activity from Stewartia pseudocamellia vol.39, pp.5, 2016, https://doi.org/10.1007/s12272-016-0717-9
  5. The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity vol.7, pp.1, 2017, https://doi.org/10.3390/plants7010001
  6. Stewartiacids A-N, C-23 carboxylated triterpenoids from Chinese Stewartia and their inhibitory effects against ATP-citrate lyase and NF-κB vol.10, pp.6, 2020, https://doi.org/10.1039/c9ra09542j
  7. Anti-Inflammatory Effect of Cudrania tricuspidata Extract and Stewartia koreana Extract Mixture in a Collagen-Induced Arthritis Mouse Model vol.11, pp.14, 2021, https://doi.org/10.3390/app11146660
  8. Acylated saponins and flavonoid glycosides from the fruits of Stewartia koreana vol.193, pp.None, 2010, https://doi.org/10.1016/j.phytochem.2021.112980