Browse > Article

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)
Publication Information
KOREAN JOURNAL OF CROP SCIENCE / v.50, no.2, 2005 , pp. 147-150 More about this Journal
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
Siegesbeckia pubescens; compositae; diterpenoid; cytotoxicity; Caki cell;
Citations & Related Records
연도 인용수 순위
  • Reference
1 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
2 Jiang, X., in Yunbao, and X. Yunlong. 1992. Diterpenoids from Siegesbeckia pubescens. Phytochemistry 31 : 917-921   DOI
3 Kim, H. M. 1997. Effects of Siegesbeckia pubescens on Immediate hypersensitivity reaction. Am. J. Chin. Med 25 : 163-167   DOI   PUBMED   ScienceOn
4 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   DOI   ScienceOn
5 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
6 Murakami, T, T lsa, and T. Satake 1973 Eine neuuntersuchung der inhaltsstoffe von Siegesbeckia pubescens Makino. Tetrahedron Lett. 14: 4491-4494
7 Giang, P. M., P. T Son, and H. Otsuka. 2005 ent-Pimarane-type diterpenoids from Siegesbeckia orientalis L. Chem. Pharm. Bull. 53 : 232-234   DOI   ScienceOn
8 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   DOI   ScienceOn
9 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   DOI   ScienceOn
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   DOI   ScienceOn
11 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
12 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
13 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   DOI   ScienceOn
14 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   DOI   ScienceOn
15 Oh, S. J. 1973. Studies on steroids of Siegesbeckia pubescens Makino. Kor. J. Pharmacogn. 4 . 95-99
16 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
17 Kim, J H 1972. A new diterpenic glucoside of Siegesbeckia pubecens. Kor J. Pharmacogn 3 : 21-22   DOI   ScienceOn
18 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
19 Kim, I. Y. 1980. A study on the diueretic action of Slegesbeckiae Herba ethanol extract in dogs. J. Kor. Pharm. Sci 10 . 5-13
20 Kim, J. H., and K. D. Han 1974. Diterpenoids of Siegesbeckia pubescens Makino. Kor. J. Pharmacogn. 5 : 17-29
21 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   DOI   ScienceOn
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   DOI   ScienceOn
23 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