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http://dx.doi.org/10.5352/JLS.2018.28.5.509

Inhibitory Effects of Flavonoids Isolated from the Leaves of Stewartia koreana on Nitric-oxide Production in LPS-stimulated RAW 264.7 Cells  

Lee, Seung-Su (Skin Biotechnology Center, Kyung Hee University)
Bang, Myun-Ho (Skin Biotechnology Center, Kyung Hee University)
Park, Se-Ho (Institute of Natural Science, Keimyung University)
Chung, Dae-kyun (Skin Biotechnology Center, Kyung Hee University)
Yang, Seun-Ah (Department of Food Science and Technology, Keimyung University)
Publication Information
Journal of Life Science / v.28, no.5, 2018 , pp. 509-516 More about this Journal
Abstract
Five phenolic compounds were isolated from the ethyl acetate fraction of leaves from Stewartia koreana, and their nitric-oxide (NO) inhibitory activities were measured to identify the major active constituents responsible for the efficacy of the extract against inflammatory reactions. These five compounds were quercetin (1), quercitrin (2), hyperin (3), quercetin-3-O-(6"-O-galloyl)-${\beta}$-D-galactopyranoside (4), and kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside (5). Among the separated compounds in the EtOAc fraction, compounds 4 and 5 were isolated for the first time, and no study has yet reported their anti-inflammatory effects. The compounds were identified by spectroscopic analysis, and the isolated compounds showed significant NO inhibitory effects in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Compound 5 showed the most potent inhibitory effect (63.35% inhibition) against LPS-induced NO production compared to that of compound 1 (17.17%), compound 2 (5.0%), compound 3 (3.92%), and compound 4 (6.32%) at $10{\mu}g/ml$ concentration. NO production was inhibited by suppressing the protein expression of inducible nitric-oxide synthase in LPS-stimulated RAW 264.7 macrophages. These results indicate that kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside might be the major active compound responsible for the anti-inflammatory effects of S. koreana.
Keywords
Glucopyranoside; kaempferol-3-o-[2'',6''-di-o-(trans-p-coumaroyl)]-${\beta}$-D-; macrophage; nitric oxide; phenolic compounds; Stewartia koreana Nakai;
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1 Lee, J. M., Kim, H. M., Lee, S., Han, S., Cho, S. H. and Lee, S. 2010. Determination of hyperin in the fruits of Acanthopanax species by high performance liquid chromatography. Nat. Prod. Sci. 16, 39-42.
2 Lee, T. H., Kwak, H. B., Kim, H. H., Lee, Z. H., Chung, D. K., Baek, N. I. and Kim, J. 2007. Methanol extracts of Stewartia koreana inhibit cycloocygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) gene expression by blocking NF-kappaB transactivation in LPS-activated RAW 264.7 cells. Mol. Cells 23, 398-404.
3 Alderton, W. K., Cooper, C. E. and Knowles, R. G. 2001. Nitric oxide synthases: structure, function and inhibition. Biochem. J. 357, 593-615.   DOI
4 Garcia-Mediavilla, V., Crespo, I., Collado, P. S., Esteller, A., Sanchez-Campos, S., Tunon, M. J. and Gonzalez-Gallego, J. 2007. The anti-inflammatory flavones quercetin and kaempferol cause inhibition of inducible nitric oxide synthase, cuclooxygenase-2 and reactive C-protein, and down-regulation of the nuclear factor kappaB pathway in Chang liver cells. Eur. J. Pharmacol. 557, 221-229.   DOI
5 Lee, T. H., Lee, G. W., Kim, C. W., Bang, M. H., Beak, N. I., Kim, S. H., Chung, D. H. and Kim, J. Y. 2010. Stewartia koreana extract stimulates proliferation and migration of human endothelial cells and induces neovasculization in vivo. Phytother. Res. 24, 20-25.   DOI
6 Lee, T. H., Lee, G. W., Park, K. H., Mohamed, M. A., Bang, M. H., Baek, Y. S., Son, Y., Chung, D. K., Baek, N. I. and Kim, J. 2014. The stimulatory effects of Stewartia koreana extract on the proliferation and migration of fibroblasts and the wound healing activity of the extract in mice. Int. J. Mol. Med. 34, 145-152.   DOI
7 Lee, T. H., Lee, S. M., Lee, D. Y., Son, Y., Chung, D. K., Baek, N. I. and Kim, J. 2011. A glycosidic spinasterol from Koreana stewartia promotes procollagen production and inhibits matrix metalloproteinase-1 expression in UVB-irradiated human dermal fibroblasts. Biol. Pharm. Bull. 34, 768-773.   DOI
8 Ha, S., Choi, Y., Jeon, Y., Kang, S., Zee, O. and Kwak, J. 2013. Phenolic compounds from the flower of Stewartia pseudo-camellia and their inhibitory effects on the release of ${\beta}$-hexosaminidase in RBL-2H3 cells. Planta Med. 79, PJ20.
9 Hossen, M. J., Jeon, S. H., Kim, S. C., Kim, J. H., Jeong, D., Sung, N. Y., Yang, S., Baek, K. S., Kim, J. H., Yoon, D. H., Song, W. O., Yoon, K. D., Cho, S. H., Lee, S., Kim, J. H. and Cho, J. Y. 2015. In vitro and in vivo anti-inflammatory activity of Phyllanthus acidus methanolic extract. J. Ethnophamacol. 168, 217-228.   DOI
10 Jeong, R. H., Lee, D. Y., Cho, J. G., Lee, S. M., Kang, H. C., Seo, W. D., Kang, H. W., Kim, J. Y. and Baek, N. I. 2011. A new flavonolignan from the aerial parts of Oryza sativa L. inhibits nitric oxide production in RAW 264.7 macrophage cells. J. Appl. Biol. Chem. 54, 865-870.
11 Kim, M. H., Jang, J. H., Oh, M. H., Heo, J. H. and Lee, M. W. 2014. The comparison of DPPH-scavenging capacity and anti-inflammatory effects of phenolic compounds isolated from the stem of Stewartia koreana Nakai. Nat. Prod. Res. 28, 1409-1412.   DOI
12 Kim, S. K., Kim, H. J., Choi, S. E., Park, K. H., Choi, H. K. and Lee, M. W. 2008. Anti-oxidative and inhibitory activities on nitric oxide (NO) and prostaglandin E2 (COX-2) production of flavonoids from seeds of Prunus tomentosa Thunberg. Arch. Pharm. Res. 31, 424-428.   DOI
13 Hamalainen, M., Nieminen, R., Vuorela, P., Heinonen, M. and Moilanen, E. 2007. Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kB activations, whereas flavones, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Mediators Inflamm. 2007, 45673.
14 Mosmann, T. 1985. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotocixity assay. J. Immunol. Methods 65, 55-63.
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.   DOI
16 Roh, H. J., Noh, H. J., Na, C. S., Kim, C. S., Kim, K. H., Hong, C. Y. and Lee, K. R. 2015. Phenolic compounds from the leaves of Stewartia pseudocamellia Maxim and their whitening activities. Biomol. Ther. 23, 283-289.   DOI
17 Yang, Z. G., Jia, L. N., Shen, Y., Ohmura, A. and Kitanaka, S. 2011. Inhibitory effects of constituents from Euphorbia lunulata on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells. Molecules 16, 8305-8318.   DOI
18 Statti, G. A., Conforti, F., Menichini, F., Marrelli, M., Gangale, C., Tundis, R., Loizzo, M. R., Bonesi, M. and Menichini, F. 2011. Protective effect of Hypericum calabricum Sprengel on oxidative damage and its inhibition of nitric oxide in lipopolysaccharide-stimulated RAW264.7 macrophages. Biol. Res. 44, 213-218.   DOI
19 Tracey, K. J. and Cerami, A. 1993. Tumor necrosis factor, other cytokines and disease. Annu. Rev. Cell Biol. 9, 317-343.   DOI
20 Yamashita, N., Etoh, H., Sakata, K., Yahi, A., Ina, H. and Ina, K. 1989. An acylated kaempferol glucoside isolated from Quercus dentate as a repellent against the blue mussel Mytilus edulis. Agr. Biol. Chem. 53, 1383-1385.
21 Zhang, Z., Li, S., Ownby, S., Wang, P., Yuan, W., Zhang, W. and Scott Beasley, R. 2008. Phenolic compounds and rare polyhydroxylated triterpenoid saponins from Eryngium yuccifolium. Phytochemistry 69, 2070-2080.   DOI
22 Zhou, Y. J., Xu, S. X., Che, Q. M. and Sun, Q. S. 2001. Flavonoids from the leaves of Quercus dentate. Indian J. Chem. 40B, 394-398.