ent-Kaurane- and ent-Pimarane-Type Diterpenoids from Siegesbeckia pubescens and Their Cytotoxicity in Caki Cells

  • Lee Sanghyun (Biohealth Products Research Center, Inje University) ;
  • Noh Eun Jung (Natural Products Research Institute, Seoul National University) ;
  • Kim Jung Sook (Biohealth Products Research Center, Inje University) ;
  • Son Eun Mi (Biohealth Products Research Center, Inje University) ;
  • Pan Xu (Biohealth Products Research Center, Inje University) ;
  • Kim Yeong Shik (Natural Products Research Institute, Seoul National University) ;
  • Kim Bak-Kwang (College of Pharmacy, Seoul National University) ;
  • Lee Burm-Jong (Biohealth Products Research Center, Inje University)
  • Published : 2005.06.01

Abstract

ent-Kaurane- and ent-pimarane-type diterpenoids were isolated from the methanol extract of Siegesbeckia pubescens by column chromatography. Their structures were elucidated as ent-16$\alpha$H,17-hydroxy-kau­ran-19-oic acid (1), ent-4,17-dihydroxy-16$\alpha$-methyl-kau­ran-19-oic acid (2), ent-16$\beta$,17-dihydroxy-kauran-19-oic acid (3), kirenol (4) and ent-16$\beta$,17,18-trihydroxy-kauran­19-oic acid (5) by spectral analysis. The cytotoxicity of these compounds in Caki cells was assayed by a cell counting kit. Only one group treated with kirenol (4), an entpimarane-type diterpenoid, showed the inhibition of the cell growth in Caki cells.

Keywords

References

  1. Ahn, D K., S. I. Lee, and H C. Kim 1998. Antihypertensive effects of crude and steamed with alcohol Siegesbeckiae Herba on the spontaneous hypertensive rats. Kor J Herbol. 13 . 53-58
  2. Dong, X. Y., M. Chen, W. Jin, D. X Huang, S. M. Shen, and H. T. Li.1989. Studies on antifertility constituents of Siegesbeckia glabrescens Mak. Acta Pharmaceut. Sin. 24 . 833-836
  3. Giang, P. M., P. T Son, and H. Otsuka. 2005 ent-Pimarane-type diterpenoids from Siegesbeckia orientalis L. Chem. Pharm. Bull. 53 : 232-234 https://doi.org/10.1248/cpb.53.232
  4. Guo, D. A., Z. G. Zhang, G. Q. Ye, and Z. C. Lou. 1997. Studies on liposoluble constituents from the aerial parts of Siegesbeckia orzentalis L. Acta Pharmaceut. Sin. 32 : 282-285
  5. Han, K. D, J.H. Kim, and S J.O h. 1975 Chemistry and pharmacology of diterpenoids of Siegesbeckia pubescens. Yakhak Hoeji 19: 129-143
  6. Han, K. D., J H. Kim, and S. J. Oh. 1973a. Studies on the diterpenes from Siegesbeckia pubescens Makmo (IV), A diterpene with kaurane skeleton Kor J Pharmacogn. 4 : 63-65
  7. Han, K. D., J. H Kim, and S. J. Oh 1973b. Studies on the diterpenes from Siegesbcekia pubescens Makino (V),Chemical structure of diterpenoid with kaurane skeleton. Kor. J. Pharmacogn. 4 205-207 https://doi.org/10.1295/polymj.4.205
  8. Hwang, W. J., E. J. Park, C. H. Jang, S. W. Han, G. J. Oh, N. S. Kim, and H. M. Kim. 2001. InhIbitory effect of immunoglobulin E production by Jin-deuk-chal (Siegesbeckia orientalis ). Immunopharmacol. Immunotoxicol. 23 . 555-563 https://doi.org/10.1081/IPH-100108601
  9. Jiang, X., in Yunbao, and X. Yunlong. 1992. Diterpenoids from Siegesbeckia pubescens. Phytochemistry 31 : 917-921 https://doi.org/10.1016/0031-9422(92)80039-H
  10. Kang, B. K., E. H. Lee, and H M. Kun 1997. Inhibitory effects of Korean folk medicine 'Hi-Chum' on histamine release from mast cells In vivo and in vitro. J. Ethnopharmacol. 57 : 73-79 https://doi.org/10.1016/S0378-8741(97)00047-0
  11. Kim, H. M. 1997. Effects of Siegesbeckia pubescens on Immediate hypersensitivity reaction. Am. J. Chin. Med 25 : 163-167 https://doi.org/10.1142/S0192415X97000184
  12. Kim, H. M., C. Y. Kim, M. H. Kwon, T. Y. Shin. and E. J. Lee. 1997 Suppression of anaphylactic reaction in mirine by Siegesbeckia pubescens. Arch. Pharm. Res. 20 : 122-127 https://doi.org/10.1007/BF02973998
  13. Kim, H. M., J. H. Lee, J. H. Won, E. J Park, H. J. Chae, H. R. Kim, C H. Kim, and S. H. Baek 2001. Inhibitory effect on Immunoglobulin E production In vivo and Invitro by Siegesbeckia glabrescens. Phytother. Res. 15 : 572-576 https://doi.org/10.1002/ptr.749
  14. Kim, I. Y. 1980. A study on the diueretic action of Slegesbeckiae Herba ethanol extract in dogs. J. Kor. Pharm. Sci 10 . 5-13
  15. Kim, J H 1972. A new diterpenic glucoside of Siegesbeckia pubecens. Kor J. Pharmacogn 3 : 21-22 https://doi.org/10.1295/polymj.3.21
  16. Kim, J. H., and K. D. Han 1974. Diterpenoids of Siegesbeckia pubescens Makino. Kor. J. Pharmacogn. 5 : 17-29
  17. Kim, J. H., K D. Han, K.Yamasaki, and O. Tanaka. 1979. Darutoside, a diterpenoid from Siegesbeckia pubescens and its structure revision. Phytochemistry 18 : 894-895 https://doi.org/10.1016/0031-9422(79)80045-X
  18. Kim, J. H, J. C Yu, I. M Chang, J. H. Lee, and J. S. Kim. 1980 Antihypertensive activities of diterpenoid ($16, 17-dihydroxy-16{\beta}-(-)-kaurane-19-oic acid$) in Siegesbeckiae pubescens against Okamoto-spontaneously hyperterisive rats. Kor J. Pharmacogn. 11 : 61-65
  19. Krrn, S. H., and B. J. Ahn. 1988. Pubetalin, the cytotoxic principle of Siegesbeckia pubescens Makino against 1210 cell. Kor. J. Pharmacogn. 17 : 251-255
  20. Murakami, T, T lsa, and T. Satake 1973 Eine neuuntersuchung der inhaltsstoffe von Siegesbeckia pubescens Makino. Tetrahedron Lett. 14: 4491-4494
  21. Oh, S. J. 1973. Studies on steroids of Siegesbeckia pubescens Makino. Kor. J. Pharmacogn. 4 . 95-99
  22. Xiang, Y., H Zhang, C. Q. Fan, and J. M. Yue 2004. Novel diterpenoids and diterpenoid glycosides from Siegesbeckia orientalis. J. Nat. Prod. 67 : 1517-1521 https://doi.org/10.1021/np0400407
  23. Zdero, C., F. Bohlmann, R. M. King, and H. Robinson. 1991. Sesquiterpene lactones and other constituents from Siegesbeckia orientalis and Guizotia scabra. Phytochemistry 30 . 1579-1584 https://doi.org/10.1016/0031-9422(91)84212-B