Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Inhibition of IL-6 Production in TNF-$\alpha$ Stimulated MG-63 by the Triterpenoids Isolated from Aucuba japonica

식나무 뿌리에서 분리한 트리테르페노이드계 화합물의 IL-6 저해효과

  • Received : 2010.04.27
  • Accepted : 2010.05.17
  • Published : 2010.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Six triterpenoid compounds, friedelin (1), $3{\alpha}$-hydroxy-2-friedelanone (2), canophyllol (3), oleanolic aldehyde acetate (4), ursolic acid (5), and pachysandiol A (6) were isolated from the methylene chloride soluble fraction of the roots of A. japonica. The chemical structures of compounds 1-6 were determined by the basis of physico-chemical properties and spectroscopic methods such as 1D and 2D NMR. These compounds were isolated from this plant for the first time. For the isolated compounds (1-3), the inhibitory effect of IL-6 production in TNF-$\alpha$ stimulated MG-63 was examined. Among the isolates, $3{\alpha}$-hydroxy-2-friedelanone (2) showed potent inhibitory effect on IL-6 production in TNF-$3{\alpha}$ stimulated MG-63.

Keywords

References

  1. 김태정 (1996) 한국의 자원식물 III, p. 205. 서울대학교출판부, 서울
  2. 배기환 (2000) 원색도감. 한국의 자연시리즈 13 한국의 약용식물, p. 359. 교학사, 서울.
  3. Bernini, R., Iavarone, C. and Trogolo, C. (1984) 1-O-${\beta}$-D-Glucopyranosyleucommol, an Iridoid glucoside from Aucuba Japonica. Phytochemistry 23: 1431. https://doi.org/10.1016/S0031-9422(00)80480-X
  4. Mysliwice, J., Kretowski, A., Topolska, J., Stepien, A. and Kinalska, I. (2002) The influence of corticosteroids on IL-6/IL-6R system in patients with graves ophthalmopathy. Pol. Arch. Med. Wewn. 108: 739.
  5. Ragab, A. A., Nalepka, J. L., Bi, Y. and Breenfield, E. M. (2002) Cytokine synergistically induce osteoclast differentiation: support by immortalized or normal calvarial cells. Am. J. Physiol. Cell. Physiol. 283: 679. https://doi.org/10.1152/ajpcell.00421.2001
  6. Skehan, P., Storeng, R., Scudiero, D. A., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H. and Kenny, S. (1990) A new colorimetric cytotoxicity assay for anticancer drug screening. J Natl. Cancer Inst. 82: 1107. https://doi.org/10.1093/jnci/82.13.1107
  7. Joo, S. S., Kang, H. C., Lee, M. W., Choi, Y. W. and Lee, D. I. (2003) Inhibition of IL-1beta and IL-6 in osteoblast-like cell by isoflavones extracted from Sophorae fructus. Arch Pham Res. 26: 1029. https://doi.org/10.1007/BF02994754
  8. Liu, Q. H., Jeong, J.-E., Choi, E. J., Moon, Y. H. and Woo, E.-R. (2006) A new furofuran lignan from Geranium thunbergii. Arch. Pharm. Res. 29: 1109. https://doi.org/10.1007/BF02969300
  9. Lee, S., Paek, S. H., Kim, S.-K., Kim, B.-K. and Shin, K. H. (2004) Triterpenoids from Orostachys japonicus. Natural Product Sciences 10: 306.
  10. Ali, M. S., Mahmud, S., Perveen, S., Ahmad, V. U. and Rizwani, G. H. (1999) Epimers from the leaves of Calophyllum inophyllum. Phytochemistry 50: 1385. https://doi.org/10.1016/S0031-9422(98)00480-4
  11. Leslie Gunatilaka, A. A., Jasmin De Silva, A. M. Y., Sotheeswaran, S., Balasubramaniam, S., Mohamed, I. M. and Wazeer, M. I. M. (1984) Terpenoid and biflavonoid constituents of Calophyllum Calaba and Garcinia Spicata from Sri Lanka. Phytochemistry 23: 323. https://doi.org/10.1016/S0031-9422(00)80326-X
  12. Guo, W. J., Guo, S. X., Yang ,J. S., Chen, X. M. and Xiao, P. G. (2007) Triterpenes and steroids from Armillaria melea Vahl. ex Fr. Biochemical Systematics and Ecology 35: 790. https://doi.org/10.1016/j.bse.2007.03.017
  13. Li, L., Huang, X., Sattler, I., Fu, H., Grabley, S. and Lin, W. (2006) Structure elucidation of a new friedelane triterpene from the mangrove plant Hibiscus tiliaceus. Magnetic Resonance in Chemistry 44: 624. https://doi.org/10.1002/mrc.1802
  14. Ngouamegne, E. T., Fongang, R. S., Ngouela, S., Boyom, F. F., Rohmer, M., Tsamo, E., Gut, J. and Rosenthal, P. J. (2008) Endodesmiadiol, a Friedelane Triterpenoid, and Other Anti-plasmodial Compounds from Endodesmia calophylloides. Chem. Pharm. Bull. 56: 374. https://doi.org/10.1248/cpb.56.374
  15. Nozaki, H., Suzuki, H., Hirayama, T., Kasai, R., Wu, R. Y. and Lee, K. H. (1986) Antitumour triterpenes of Maytenus Diversifolia. Phytochemistry 25: 479. https://doi.org/10.1016/S0031-9422(00)85505-3
  16. Kim, M. R., Lee, H. H., Hahm, K. S., Moon, Y. H. and Woo, E. R. (2004) Pentacyclic triterpenoids and their cytotoxicity from the Stem Bark of Styrax japonica S. et Z. Arch. Pharm. Res. 27: 283. https://doi.org/10.1007/BF02980060
  17. Nomura, M., Tokoroyama, T. and Kubota, T. (1981) Biarylheptanids and other comstituents from wood of Alnus japonica. Phytochemistry 20: 1097. https://doi.org/10.1016/0031-9422(81)83035-X
  18. Kircher, H. W. (1980) Triterpenes in organ pipe cactus. Phytochemistry 19: 2707. https://doi.org/10.1016/S0031-9422(00)83947-3
  19. Ibrahim, A., Khalifa, S. I., Khafagi, I., Youssef, D. T., Khan, S., Mesbah, M. and Khan, I. (2008) Microbial Metabolism of Biologically Active Secondary Metabolites from Nerium oleander L. Chem. Pharm. Bull. 56: 1253. https://doi.org/10.1248/cpb.56.1253
  20. Jaki, B. U., Franzblau, S. G., Chadwick, L. R., Lankin, D. C., Zhang, F., Wang, Y. and Pauli, G. F. (2008) Purity Activity Relationships of Natural Products: The Case of Anti-TB Active Ursolic Acid. J. Nat. Prod. 71: 1742. https://doi.org/10.1021/np800329j
  21. Moiteiro, C., Justino, F., Tacares, R., Marcelo-Curto, M. J., Florencio, M. H., Nascimento, M. S. J., Pedro, M., Cerqueira, F. and Pinto, M. M. (2001) Synthetic secofriedelane and friedelane derivatives as inhibitors of human lymphocyte proliferation and growth of human cancer cell lines in vitro. J. Nat. Prod. 64: 1273. https://doi.org/10.1021/np010217m
  22. Qu, L., Chen, X., Lu, J., Yuan, J. and Zhao, Y. (2005) Chemical components of Leptopus chinensis. Chemistry of Natural Compounds 40: 565.