Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Cytotoxic and COX-2 Inhibitory Constituents from the Aerial Parts of Aralia cordata

  • Lee, Ik-Soo (College of Pharmacy, Chungnam National University) ;
  • Jin, Wen-Yi (College of Pharmacy, Chungnam National University) ;
  • Zhang, Xin-Feng (College of Pharmacy, Chungnam National University) ;
  • Hung, Tran-Manh (College of Pharmacy, Chungnam National University) ;
  • Song, Kyung-Sik (College of Agriculture and Life Science, Kyungpook National University) ;
  • Seong, Yeon-Hee (College of Veterinary Medicine and Research Institute of Veterinary Medicine, Chungbuk National University) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Published : 2006.07.01
Download PDF
⟨ Previous Next ⟩

Abstract

Three diterpenes (1, 8, and 9), three triterpenes (3, 4, and 7), one saponin (11), four sterols (2, 5, 6, and 12), and one cerebroside (10) were isolated from the EtOH extract of the aerial parts of Aralia cordata by repeated silica gel column chromatography. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for their cytotoxicity against L1210, K562, and LLC tumor cell lines using MTT assay. Of which, $3{\beta},5{\alpha}-dihydroxy-6{\beta}-methoxyergosta-7,22-diene$ (6) showed a potent cytotoxicity against all cell lines with $IC_{50}$ values of 11.7, 11.9, and $15.1\;{\mu}M$, respectively, while compounds 1, 5, and 11 showed a moderate or weak cytotoxicity. These isolates were also examined for their inhibitory activity against COX-1 and COX-2. Although most compounds, except for 2, 10, and 12, showed a strong inhibitory activity against COX-1, they exhibited a moderate or weak inhibitory activity against COX-2.

Keywords

References

  1. Cai, X. F., Shen, G., Dat, N. T., Kang, O. H., Lee, Y. M., Lee, J. J., and Kim, Y. H., Inhibitory effect of kaurane type diterpenoids from Acanthopanax koreanum on TNF-${\alpha}$ secretion from trypsin-stimulated HMC-1 cells. Arch. Pharm. Res., 9, 731-734 (2003)
  2. Cambie, R. C., Burfitt, I. E., Goodwin, T. E., and Wenkert, E., The structure of hallol, J. Org. Chem., 40, 3789-3791 (1975) https://doi.org/10.1021/jo00913a042
  3. Dang, N. H., Zhang, X. F., Zheng, M. S., Son, K. H., Chang, H. W., Kim, H. P., Bae, K. H., and Kang, S. S., Inhibitory Constituents against Cyclooxygenases from Aralia cordata Thunb. Arch. Pharm. Res., 28, 28-33 (2005) https://doi.org/10.1007/BF02975131
  4. Han, B. H., Han, Y. N., Han, L. A., Park, M. H., and Lee, E. O., Studies on the anti-inflammatory activity of Aralia continentalis (I). Arch. Pharm. Res., 6, 17-23 (1983) https://doi.org/10.1007/BF02855697
  5. Hirokazu, K., Ryosuke, K., Toshimi, S., Takashi, M., Toshihiko, H., and Takuji, N., Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry, 27, 2777-2779 (1988) https://doi.org/10.1016/0031-9422(88)80662-9
  6. Hung, C. Y. and Yen, G. C., Extraction and identification of antioxidative components of Hsian-tsao (Mesona procumbens Hemsl.). Lebensm.-Wiss. u.-Technol., 34, 306-311 (2001) https://doi.org/10.1006/fstl.2001.0775
  7. Ito, T., Tsukiji, K., and Odagiri, S., Constituents of the Head Space Gas of Udo (Aralia cordata Thunb.). Nippon Nogeikagaku Kaishi, 52, 223-224 (1978) https://doi.org/10.1271/nogeikagaku1924.52.5_223
  8. Jares, E. A., Tettamanzi, M. C., and Pomilio, A. B., Sitosterol 3-O-${\beta}$-D-glucuronopyranoside from Senecio bonariensis. Phytochemistry, 29, 340-341 (1990) https://doi.org/10.1016/0031-9422(90)89069-L
  9. Kang, S. S., Kim, J. S., Xu, Y. N., and Kim, Y. H., Isolation of a new cerebroside from the root bark of Aralia elate. J. Nat. Prod., 62, 1059-1060 (1999) https://doi.org/10.1021/np990018r
  10. Kwon, H. C. and Lee, K. R., Phytochemical Constituents of Artemisia japonica ssp. littoricola. Arch. Pharm. Res., 24, 194-197 (2001) https://doi.org/10.1007/BF02978255
  11. Kwon, H. C., Zee, S. D., Cho, S. Y., Choi, S. U., and Lee, K. R., Cytotoxic ergosterols from Paecilomyses sp. J300. Arch. Pharm. Res., 25, 851-855 (2002) https://doi.org/10.1007/BF02977003
  12. Lee, K. R., Peroxide Constituents in the Natural Product Research. Kor. J. Pharmacogn., 22, 145-155 (1991)
  13. Mosmann, T. J., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicicity assays. J. Immunol. Methods, 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  14. Okuyama, E., Nishimura, S., and Yamazaki, M., Analgesic principles from Aralia cordata Thunb. Chem. Pharm. Bull., 39, 405-407 (1991) https://doi.org/10.1248/cpb.39.405
  15. Park, S. H., Oh, S. R., Jung, K. Y., Lee, I. M., Ahn, K. S., Kim, J. G., Lee, J. J., and Lee, H. K., Anticomplement activities of oleanolic acid monodesmosides and bisdesmosides isolated from Tiarella polyphylla. Arch. Pharm. Res., 22, 428-431 (1999) https://doi.org/10.1007/BF02979071
  16. Park, S. Y. and Kim, J. W., Cytotoxic Polyacetylenes from Aralia cordata. Yakhak Hoeji, 39, 681-688 (1995)
  17. Perry, L. M., Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses; The MIT Press, Cambridge, p. 41 (1980)
  18. Sakurai, N., Yaguchi, Y., and Inoue, T., Triterpenoids from Myrica rubra. Phytochemistry, 26, 217-219 (1987) https://doi.org/10.1016/S0031-9422(00)81515-0
  19. Sam, N., San-Miguel, B. Arreguy, Taran, M., and Delmond, B., Synthesis and rearrangement of methyl 8,14${\beta}$-epoxypimarate on the route to cassane diterpene skeleton. Tetrahedron, 47, 9187-9194 (1991) https://doi.org/10.1016/S0040-4020(01)96206-4
  20. Sati, O. P., Uniyal, S. K., Bahuguna, S., and Kikuchi, T., Clematoside-S, A triterpenoid saponin from the roots of Clematis grata. Phytochemistry, 29, 3676-3678 (1990) https://doi.org/10.1016/0031-9422(90)85304-X
  21. Sawamura, M., Kim, M. S., Shichiri, K., Tsuji, T., and Machida, K., Volatile constituents of Japanese and Korean Udo (Aralia cordata Thunb.) and Butterbur (Petasites japonicus Miq.). Research Reports of the Kochi University, 38, 49-60 (1989)
  22. Shim, J. S., Park, K. M., Chung, J. Y., and Hwang, J. K., Antibacterial activity of oleanolic acid from Physalis angulata against oral pathogens. Nutraceuticals & Food, 7, 215- 218 (2002) https://doi.org/10.3746/jfn.2002.7.2.215
  23. Sugiyama, S., Honda, M., Higuchi, R., and Komori T., Stereochemistry of the Four Diastereomers of Ceramide and Ceramide Lactoside. Liebigs Ann. Chem., 349-356 (1991)
  24. Sy, L. K. and Brown, G. D., Abietane diterpenes from Illicium angustisepalum. J. Nat. Prod., 61, 907-912 (1998) https://doi.org/10.1021/np980054a
  25. Ylva, N., Therese, R., Premila, P., Helena, D., and Lars, B., Development of a radiochemical cyclooxygenase-1 and 2 in vitro assay for identification of natural products as inhibitor of prostaglandin biosynthesis. J. Nat. Prod., 61, 2-7 (1998) https://doi.org/10.1021/np970343j
  26. Yoshihara, K. and Hirose, Y., Terpenes from Aralia Species. Phytochemistry, 12, 468 (1973) https://doi.org/10.1016/0031-9422(73)80044-5