Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Topoisomerase I and II Inhibitory Activities and Cytotoxic Constituents from the Barks of Tilia amurnesis

  • Received : 2011.06.02
  • Accepted : 2011.08.23
  • Published : 2011.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Eight compounds, squalene (1), friedelin (2), ${\beta}$-sitosterol (3), ${\beta}$-sitosterol-3-O-glucoside (4), ${\alpha}$-tocopherol (5), betulinic acid (6), trilinolein (7) and 1-O-(9Z,12Z-Octadecadienoyl)-3-nonadecanoyl glycerol (8), were isolated from the barks of Tilia amurensis. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in the literature. These isolated compounds were examined for their inhibitory activities against topoisomerase I and II. Compound 7 showed significant inhibition of DNA topoisomerase I and II activities, with percent decreases in activity of 87 and 95%, respectively at a concentration of $100\;{\mu}M$. Compound 6 exhibited cytotoxicity against the human colon adenocarcinoma cell line (HT-29), the human breast adenocarcinoma cell line (MCF-7) and the human liver hepatoblastoma cell line (HepG-2), with $IC_{50}$ values of 20, 59 and $16\;{\mu}M$, respectively.

Keywords

References

  1. Ahn, D.K., Illustrated Book of Korean Medicinal Herbs, Kyohak Publishing Co., Ltd., Seoul, 2003, pp. 56.
  2. Ali, M.S., Mahmud, S., Perveen, S., Ahmad, V.U., and Rizwani, G.H., Epimers from the leaves of Calophyllum inophyllum, Phytochemistry, 50(8), 1385-1389 (1999). https://doi.org/10.1016/S0031-9422(98)00480-4
  3. Aydin, S., Ozturk, Y., Baser, K.H.C., Kirimer, N., and Kurtarozturk, N., Effects of Alcea pallid L (A) and Tilia argentea Desf Ex Dc infusions on swimming performance in mice. Phytother. Res., 6, 219-220 (1992). https://doi.org/10.1002/ptr.2650060411
  4. Chatterjee, P., Pezzuto, J.M., and Kouzi, S.A., Glucosidation of betulinic acid by Cunninghamella species, J. Nat. Prod., 62(5), 761-763 (1999). https://doi.org/10.1021/np980432b
  5. Hickok, L.G. and Anway, J.C., A morphological and chemical analysis of geographical variation in Tilia L. of eastern North America. Brittonia, 24, 2-8 (1972). https://doi.org/10.2307/2805542
  6. Kim, C.M., Kang, S.S., Park, Y.S., and Kim, E.Y., Studies on the chemical constituents of Tilia plants in Korea (I). On the chemical constituents of the stem-bark of Tilia mandsurica. Kor. J. Pharmacogn., 19(3), 174-176 (1988).
  7. Kim, D.K., Lim, J.P., Kim, J.W., Park, H.W., and Eun, J.S., Antitumor and anti-inflammatory constituents from Celtis sinensis, Arch. Pharm. Res., 28(1), 39-43 (2005). https://doi.org/10.1007/BF02975133
  8. Kitajima, J., Kimizuka, K., Arai, M., and Tanaka, Y., Constituents of Ficus pumila Leaves, Chem. Pharm. Bull., 46(10), 1647-1649 (1998). https://doi.org/10.1248/cpb.46.1647
  9. Klass, J., Tinto, W.F., Mclean, S., and Reynolds, W.F., Friedlane triterpenoids from Peritassa compta: complete $^{1}H$ and $^{13}C$ assignments by 2D NMR spectroscopy, J. Nat. Prod., 55(11), 1626-1630 (1992). https://doi.org/10.1021/np50089a010
  10. Ngnokam, D., Massiot, G., Nuzillard, J.M., Connolly, J.D., Tsamo, E., and Morin, C., Sapelenins A, B and C, acyclic triterpenoids from the stem bark of Entandrophragma cylindricum, Phytochemistry, 34(6), 1603-1607 (1993). https://doi.org/10.1016/S0031-9422(00)90854-9
  11. Nick, A., Wright, A.D., Rali, T., and Sticher, O., Antibacterial treterpenoids from Dillenia papuana and their structure-activity relationships, Phytochemistry, 40(6), 1691-1695 (1995). https://doi.org/10.1016/0031-9422(95)00491-O
  12. Nishiyama, Y., Moriyasu, M., Ichimaru, M., Tachibana, Y., Kato, A., Mathenge, S.G., Nganga, J.N., and Juma, F.D., Acyclic triterpenoids from Ekebergia capensis, Phytochemistry, 42(3), 803-807 (1996). https://doi.org/10.1016/0031-9422(96)00004-0
  13. Nozawa, M., Takahashi, K., Kato, K., and Akita, H., Enantioselective synthesis of (2R,4'R,8'R)- $\alpha$-tocopherol (vitamin E) based on enzymatic function, Chem. Pharm. Bull., 48(2), 272-277 (2000). https://doi.org/10.1248/cpb.48.272
  14. Ma, C.Y., Liu, W.K., and Che, C.T., Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J. Nat. Prod., 65, 206-209 (2002). https://doi.org/10.1021/np010073b
  15. Mannina, L., Luchinat, C., Emanuele, M.C., and Segre, A., Acyl positional distribution of glycerol tri-esters in vegetable oils: a 13C NMR study. Chem.Phys. Lipids, 103, 47-55 (1999). https://doi.org/10.1016/S0009-3084(99)00092-4
  16. Matsuda, H., Ninomiya, K., Shimoda, H., and Yoshikawa, M., Hepatoprotective principles from the flowers of Tilia argentea (Linden): Structure requirements of tiliroside and mechanism of action. Bioorg. Med. Chem., 10, 707-712 (2002). https://doi.org/10.1016/S0968-0896(01)00321-2
  17. Park, J.H., Medicinal Plants of Korea, Shinil Book Co., Seoul, 2004, pp. 896-900.
  18. Pietta, P., High-performance liquid chromatography and micellar electrokinetic chromatography of flavonol glycosides from Tilia. J. Chromatogr., 638, 357-361 (1993). https://doi.org/10.1016/0021-9673(93)83449-3
  19. Rubinstein, L.V., Shoemaker, R.H., Paul, K.D., Simon, R.M., Tosini, S., Skehan, P., Scudiero, D.A., Monks, A., and Boyd, M.R., Comparison of in vitro anticancer-drug-screening data generated with a lines. J. Nat. Cancer Inst., 82, 1113-1118 (1990). https://doi.org/10.1093/jnci/82.13.1113
  20. Sakamoto, T., Tomita, K., Yanagi, M., Ozawa, T., and Kajiwara, M., Biological resolution of (2RS)-tocopherol and (2RS)-tocopheryl acetate, Chem. Pharm. Bull., 39(1), 130-132 (1991). https://doi.org/10.1248/cpb.39.130
  21. Toker, G., Kupeli, E., Memisoglu, M., and Yesilada, E., Flavonoids with antinociceptive and anti-inflammatory activities from the leaves of Tilia argentea (silver linden). J. Ethnopharmacol., 95, 393-397 (2004). https://doi.org/10.1016/j.jep.2004.08.008
  22. Viola, H., Wolfman, C., Destein, M.L., Wasowski, C., Pena, C., Medina, J.H., and Paladine, A.C., Isolation of pharmacologically active benzodiazepine receptor ligands from Tilia tomentosa (Tiliceae). J. Ethnopharmacol., 44, 47-53 (1994). https://doi.org/10.1016/0378-8741(94)90098-1
  23. Yu, Y.P., Kang, S.S. and Kim, C.M., A study on the chemical constituents of Tilia Koreana Nakai. Kor. J. Pharmacogn., 21(4), 265-269 (1990).