Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Anti-inflammatory Activity of Flavonoids from Populus davidiana

  • Published : 2006.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the stem bark of Populus davidiana showed considerable inhibitory activity against cyclooxygenase (COX-1, COX-2). Continuous phytochemical study of the MeOH extract of this plant led to the isolation of ten flavonoids; sakuranetin (1), rhamnocitrin (2), 7-O-methylaromadendrin (3), naringenin (4), eriodictyol (5), aromadendrin (6), kaempferol (7), neosakuranin (8), sakuranin (9) and sakurenetin-5,4'-di-${\beta}$-D-glucopyranoside (10). Their structures were identified on the basis of their physicochemical and spectroscopic analyses. The isolated compounds, 1-10, were tested for their inhibitory activities against COX-1 and COX-2. Compound 7 was found to have potent inhibitory effect on COX-1 and a moderate effect on COX-2, meanwhile, compounds 1-6 showed moderate inhibition against COX-1 only. Moreover, compounds 5-8 exhibited suppressive effects on xanthine oxidase (XO). These results may explain, in part, the traditional uses of P. davidiana in ethnomedicine.

Keywords

References

  1. Bae, K., The medicinal plants of Korea. Kyo-Hak Publishing Co., Seoul, p. 98, (1999)
  2. Borne, R. F., Nonsteroidal anti-inflammatory drugs. Principles of medicinal chemistry. Williams & Wilkins, U.S.A., Fourth edition, p. 535–580 (1995)
  3. Cos, P., Ying, L., Calomme, M., Hu, J. P., Cimanga, K., Van Poel, B., Pieters, L., Vlietinck, A. J., and Vanden Berghe, D., Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J. Nat. Prod., 61, 71-76 (1998) https://doi.org/10.1021/np970237h
  4. El-Sohly, H. N., Joshi, A., Li, X. C., and Ross, S. A., Flavonoids from Maclura tinctoria. Phytochemistry, 52, 141-145 (1999) https://doi.org/10.1016/S0031-9422(99)00126-0
  5. Emery, P., COX-1, COX-2: So what? Scand. J. Rheumatol., 28, 6-9 (1999) https://doi.org/10.1080/03009749950155715
  6. Fujimoto, Y., Uno, E., and Sakuma, S., Effects of reactive oxygen and nitrogen species on cyclooxygenase-1 and -2 activities. Prostaglandins, Leukot. Essent. Fatty acids, 71, 335-340 (2004) https://doi.org/10.1016/j.plefa.2004.06.002
  7. Jang, D. S., Cuendet, M., Pawlus, A. D., Kardono, L. B.S., Kawanishi, K., Farnsworth, N. R., Fong, H. H. S., Pezzuto, J. M., and Kinghorn, A. D., Potential cancer chemopreventive constituents of the leaves of Macaranga triloba. Phytochemistry, 65, 345-350 (2004) https://doi.org/10.1016/j.phytochem.2003.10.026
  8. Kim, J. E., Jung, M. J., Jung, H. A., Woo, J. J., Cheigh, H. S., Chung, H. Y., and Choi, J. S., A new kaempferol 7-Otriglucoside from the leaves of Brassica juncea L. Arch. Pharm. Res., 25, 621-624 (2002) https://doi.org/10.1007/BF02976932
  9. Lee, E. H., Kim, H. J., Song, Y. S., Jin, C., Lee, K. T., Cho, J., and Lee, Y. S., Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Arch. Pharm. Res., 26, 1018-1023 (2003) https://doi.org/10.1007/BF02994752
  10. Leiro, J. M., Alvarez, E., Arranz, J. A., Cano, E., and Orallo, F., Antioxidant activity and inhibitory effects of hydralazine on inducible NOS/COX-2 gene and protein expression in rat peritoneal macrophages. Int. Immunopharmacol., 4, 163-177 (2004) https://doi.org/10.1016/j.intimp.2003.10.004
  11. Lin, J. H., Chiou, Y. N., and Lin, Y. L., Phenolic glycosides from Viscum angulatum. J. Nat. Prod., 65, 638-640 (2002) https://doi.org/10.1021/np010548z
  12. Marnett, L. J., Goodwin, D. C., Rowlinson, S. W., Kalgutkar, A. S., and Landino, L. M., Structure, function, and inhibition of prostaglandin endoperoxide synthases. Compr. Nat. Prod. Chem., 5, 225-261 (1999)
  13. Min, B. S., Na, M. K., Oh, S. R., Ahn, K. S., Jeong, G.. S., Li, G., Lee, S. K., Joung, H., and Lee, H. K., New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica. J. Nat. Prod., 67, 1980-1984 (2004) https://doi.org/10.1021/np040113m
  14. Nguyen, M. T. T., Awale, S., Tezuka Y., Ueda, J. Y., Tran, Q. L., and Kadota, S., Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense. Planta Med., 72, 46-51 (2006) https://doi.org/10.1055/s-2005-873181
  15. Noreen, Y., Ringbom, T., Perera, P., Danielson, H., and Bohlin, L., Development of a radiochemical cyclooxygenase-1 and - 2 in vitro assay for identification of natural products as inhibitors of prostaglandin biosynthesis. J. Nat. Prod., 61, 2-7 (1998) https://doi.org/10.1021/np970343j
  16. Parejo, I., Viladomat, F., Bastida, J., Guiliermo, S. H., Burillo, J., and Codina, C., Bioguided isolation and identification of the nonvolatile antioxidant compounds from Fennel (Foeniculum vulgare Mill.) waste. J. Agric. Food Chem., 52, 1890-1897 (2004) https://doi.org/10.1021/jf030717g
  17. Reichel, L. and Freytag, D., Chemistry and biochemistry of plant constituents. XXVI. Syntheses of methoxy-substituted chalcone and flavanone derivatives under mild conditions. Justus Liebigs Annalen der Chemie, 729, 225-230 (1969) https://doi.org/10.1002/jlac.19697290128
  18. Ryu, J. H., Ahn, H., Kim, J. Y., and Kim, Y. K., Inhibitory activity of plant extracts on nitric oxide synthesis in LPS-activated macrophages. Phytother. Res., 17, 485-489 (2003) https://doi.org/10.1002/ptr.1180
  19. S. Ibrahim, A. R., Sulfation of naringenin by Cunninghamella elegans. Phytochemistry, 53, 209-212 (2003) https://doi.org/10.1016/S0031-9422(99)00487-2
  20. Scio, E., Ribeiro, A., Alves, T. M. A., Romanha, A. J., Dias de Souza Filho, J., Cordell, G. A., and Zani, C. L., Diterpenes from Alomia myriadenia (Asteraceae) with cytotoxic and trypanocidal activity. Phytochemistry, 64, 1125-1131 (2003) https://doi.org/10.1016/S0031-9422(03)00529-6
  21. Star, V. L. and Hochberg, M. C., Prevention and management of gout. Drugs, 45, 212–222 (1993) https://doi.org/10.2165/00003495-199345020-00004
  22. Thapliyal, R. P., Bahuguna, R. P., Constituents of Prunus cerasoides. Fitoterapia, 64, 473 (1993)
  23. Valentao, P., Fernandes, E., Carvalho, F., Andrade, P. B., Seabra, R. M., Seabra, R. M., and De Lourdes Bastos, M., Studies on the antioxidant activity of Lippia citriodora infusion: scavenging effect on superoxide radical, hydroxyl radical and hypochlorous acid. Biol. Pharm. Bull., 25, 1324- 1327 (2002) https://doi.org/10.1248/bpb.25.1324
  24. Vasconcelos, J. M. J., Silva, A. M. S., and Cavaleiro, J. A. S., Chromones and flavanones from Artemisia campestris Subsp. Maritima. Phytochemistry, 49, 1421-1424 (1998) https://doi.org/10.1016/S0031-9422(98)00180-0
  25. Wang, X., Wang, Q., and Wang, H., Chemical constituents in the bark of Populus davidiana. Chinese traditional and herbal drugs, 31, 891-892 (2000)
  26. Wang, X., Wang, Q., Xu, G. J., and Xu, L. S., Advances in the research of constituents and pharmacology of Populus L.. Tianran Chanwu Yanjiu Yu Kaifa, 11, 65-74 (1999)
  27. Wu, L., Smythe, A. M., Stinson, S. F., Mullendore, L. A., Monks, A., Scudiero, D. A., Paull, K. D., Koutsoukos, A. D., Rubinstein, L. V., Boyd, M. R., and Shoemaker, R. H., Multidrug-resistant phenotype of disease-oriented panels of human tumor cell lines used for anticancer drug screening. Cancer Res., 52, 3029-3034 (1992)
  28. Yoshinari, K., Shimazaki, N., Sashida, Y., and Mimaki, Y., Flavanone xyloside and lignans from Prunus jamasakura bark. Phytochemistry, 29, 1675-1678 (1990) https://doi.org/10.1016/0031-9422(90)80144-6
  29. Zhong Hua Ben Cao, Shanghai Science and Technology Publishing Co., Vol. 2, p. 389 (1999)
  30. Zhou, Sh., Lin, M., Wang, Y. H., and Liu, X., Study on the chemical constituents of Populus davidiana Dode. Tianran Chanwu Yanjiu Yu Kaifa, 14, 43-45 (2002)