Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Inhibitory Effect on TNF-${\alpha}$-Induced IL-8 Production in the HT29 Cell of Constituents from the Leaf and Stem of Weigela subsessilis

  • Thuong Phuong Thien (College of Pharmacy, Chungnam National University) ;
  • Jin WenYi (College of Pharmacy, Chungnam National University) ;
  • Lee JongPill (Korea Food & Drug Administration) ;
  • Seong RackSeon (Korea Food & Drug Administration) ;
  • Lee Young-Mi (Department of Oriental Pharmacy, College of Pharmacy, Wonkwang University) ;
  • Seong YeonHee (College of Agriculture and Life Science, Kyungbuk National University) ;
  • Song KyungSik (College of Veterinary Medicine, Chungbuk National University) ;
  • Bae KiHwan (College of Pharmacy, Chungnam National University)
  • Published : 2005.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

Twelve compounds were isolated from the MeOH extract of the leaf and stem of the Korean endemic plant Weigela subsessilis L. H. Bailey. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. These compounds were identified as three sterols, ${\beta}$-sitosterol acetate (2), ${\beta}$-sitosterol (3), daucosterol (11), eight triterpenoids, squalene (1), ursolic acid (4), ilekudinol A (5), corosolic acid (6), ilekudinol B (7), esculentic acid (8), pomolic acid (9), asiatic acid (10), and one iridoid glycoside, alboside I (12). This is the first report pertaining to the isolation of these compounds from Weigela subsessilis L. H. Bailey. In addition, three compounds 7, 9, and 12 were found to display a strong inhibitory effect on the production of IL-8 in the HT29 cells stimulated by TNF-${\alpha}$.

Keywords

References

  1. Adnyana, I. K., Tezuka, Y., Banskota, A. H., Tran, K. Q., and Kadota, S., Hepatoprotective constituents of the seeds of Combretum quadrangulare. Biol. Pharm. Bull., 23, 1328-1332 (2000) https://doi.org/10.1248/bpb.23.1328
  2. Ahmad, V. U., Bano, S., and Bano, N., A triterpene acid from Nepeta hindostana. Phytochemistry, 25, 1487-1488 (1986) https://doi.org/10.1016/S0031-9422(00)81318-7
  3. Burger, B. V., Le, R. M., Spies, H. S. C., Truer, V., and Bigalke, R. C., Mammalian pheromone studies. III. (E,E)-7,11,15-trimethyl-3-methylenehexadeca-1,6,10,14-tetraene, a new diterpene analog of $\beta$-farnesene from the dorsal gland of the springbok Antidorcas marsupialis. Tetrahedron Lett., 52, 5221-5224 (1978) https://doi.org/10.1016/S0040-4039(01)85855-X
  4. Carbonezi, C. A., Martins, D., Young, M. C. M., Lopes, M. N., Furlan, M., Filho, E. R., and Bolzani, V. S., Iridoid and secoiridoid glucosides from Chiococca alba (Rubiaceae). Phytochemistry, 51, 781-785 (1999) https://doi.org/10.1016/S0031-9422(99)00105-3
  5. Chang, C. S., Flavonoids chemistry of Weigela (Caprifoliaceae) in Korea. J. Plant Res., 110, 275-281 (1997) https://doi.org/10.1007/BF02509316
  6. Chang, I. M., Yun, H. S., and Yamasaki, K., Revision of $^{13}C-NMR$ assignments of $\beta$-sitosterol and $\beta$-sitosteryl-3-O-$\beta$-glucopyranoside isolated from Plantago asiatica seed. Kor. J. Pharmacog., 12, 12-14 (1981)
  7. Chaturvedula, V. S. P., Schilling, J. K., Miller, J. S., Andriantsiferana, R., Rasamison, V. E., and Kingston, D. G. I., New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar rainforest. J. Nat. Prod., 67, 895-898 (2004) https://doi.org/10.1021/np0303512
  8. Cheng, D. L. and Cao, X. P., Pomolic acid derivatives from the root of Sanguisorba officinalis. Phytochemistry, 31, 1317-1320 (1992) https://doi.org/10.1016/0031-9422(92)80499-5
  9. Furuya, T., Orihara, Y., and Hayashi, C., Studies on plant tissue culture. Part 48. Triterpenoids from Eucalyptus perriniana cultured cells. Phytochemistry, 26, 715-719 (1987) https://doi.org/10.1016/S0031-9422(00)84771-8
  10. Iwagawa, T. and Hase, T., Constituents of the leave of Weigela coraeensis. Kagoshima Daigaku Rigakubu Kiyo, Sugaku, Butsurigaku, Kagaku, 21, 81-87 (1988)
  11. Judy, W. V., Hari, S. P., Stogsdill, W. W., Judy J. S., Naguib, Y. M. A., and Passwater, R., Antidiabetic activity of a standardized extract (Glucosol) from Lagerstroemia speciosa leaves in Type II diabetics. A dose-dependence study. J. Ethnopharmacol., 87, 115-117 (2003) https://doi.org/10.1016/S0378-8741(03)00122-3
  12. Kashiwada, Y., Wang, H. K., Nagao, T., Kitanaka, S., Yasuda, I., Fujioka, T., Yamagishi, T., Cosentino, L. M., Kozuka, M., Okabe, H., Ikeshiro, Y., Hu, C. Q., Yeh, E., and Lee, K. H., Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J. Nat. Prod., 61, 1090-1095 (1998) https://doi.org/10.1021/np9800710
  13. Kim, J. A., Kim, D. K., Tae, J., Kang, O. H., Choi, Y. A., Choi, S. C., Kim, T. H., Nah, Y. H., Choi, S. J., Kim, Y. H., Bae, K. H., and Lee, Y. M., Acanthoic acid inhibits IL-8 production via MAPKs and $NF-\kappaB$ in a TNF-a-stimulated human intestinal epithelial cell line. Clin. Chim. Acta, 342, 193-202 (2004a) https://doi.org/10.1016/j.cccn.2004.01.004
  14. Kim, M. Y., Korean Endemic Plants. Solkwahak, Seoul, pp. 168-169, 339 (2004b)
  15. Liu, J., Liu, Y., Mao, Q., and Klaassen, C. D., The effects of 10 triterpenoid compounds on experimental liver injury in mice. Fundam. Appl. Toxicol., 22, 34-40 (1994) https://doi.org/10.1006/faat.1994.1005
  16. Miura, T., Itoh, Y, Kaneko, T., Ueda, N., Ishida, T., Fukushima, M., Matsuyama, F., and Seino, Y., Corosolic acid induces GLUT4 translocation in genetically type 2 diabetic mice. Biol. Pharm. Bull., 27, 1103-1105 (2004) https://doi.org/10.1248/bpb.27.1103
  17. Na, M. K., An, R. B., Min, B. S., Lee, S. M., Kim, Y. H., and Bae, K. H., Chemical constituents from Sorb us commixta. Nat. Prod. Sci., 8, 62-65 (2002)
  18. Nishimura, K., Fukuda, T., Miyase, T., Noguchi, H., and Chen, X. M., Activity-guided isolation of triterpenoid acyl CoA cholesteryl acyl transferase (ACAT) inhibitors from llex kudincha. J. Nat. Prod., 62, 1061-1064 (1999) https://doi.org/10.1021/np990019j
  19. Oh, S. R., Kinjo, J., Shii, Y., Ikeda, T., Nohara, T., Ahn, K. S., Kim, J. H., and Lee, H. K., Effects of triterpenoids from Pueraria lobata on immunohemolysis: B-D-glucuronic acid plays an active role in anticomplementary activity in vitro. Planta Med., 66, 506-510 (2000) https://doi.org/10.1055/s-2000-8614
  20. Rajic, A., Akihisa, T., Ukiya, M., Yasukawa, K., Sandeman, R. M., Chandler, D., S., and Polya, G. M., Inhibition of trypsin and chymotrypsin by anti-inflammatory triterpenoids from Compositae flowers. Planta Med., 67, 599-604 (2001) https://doi.org/10.1055/s-2001-17350
  21. Taniguchi, S., Imayoshi, Y., Kobayashi, E., Takamatsu, Y., lto, H., Hatano, T., Sakagami, H., Tokuda, H., Nishino, H., Sugita, D., Shimura, S., and Yoshida, T., Production of bioactive triterpenes by Eriobotrya japonica calli. Phytochemistry, 59, 315-323 (2002) https://doi.org/10.1016/S0031-9422(01)00455-1
  22. Thuong, P. T., Na, M. K., Su, N. D., Seong, R. S., Lee, Y. M., Sok, D. E., and Bae, K. H., Inhibitory effect of coumarins from Weigela subsessilis on low density lipoprotein oxidation. Biol. Pharm. Bull., 28, 1095-1097 (2005) https://doi.org/10.1248/bpb.28.1095
  23. Won, H. M., Kwon, Y. S., Lee, J. H., and Kim, C. M., Chemical constituents of the leaves of Weigela subsessillis. Kor. J. Pharmacog., 35, 1-5 (2004)