Archives of Pharmacal Research

  • 제28권3호
  • /
  • Pages.280-284
  • /
  • 2005
  • /
  • 0253-6269(pISSN)
  • /
  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Sesquiterpenes from Syneilesis palmata and Their Cytotoxicity Against Human Cancer Cell Lines In Vitro

  • Lee Kyu Ha (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Cho Sang Un (Research Institute of Chemical Technology) ;
  • Lee Kang Ro (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University)
  • 발행 : 2005.03.01
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

The chromatographic separation of the MeOH extract from the aerial parts of Syneilesis palmata led to the isolation of a new sesquiterpene glycoside 4, together with four known compounds. Their structures were characterized to be 4$\beta$,5$\beta$-epoxy-caryophill-8,(15)-ene (1), 3$\beta$­hydroxy-gultin-5-ene (2), 4$\alpha$,5$\beta$-dihydroxy-caryophill-8,(15)-ene (3), (-)-oplopan-4-one-10-$\alpha$-O­$\beta$-D-glucose (4) and 3-hexenyl-1-O-$\beta$-D-glucopyranose (5), based on spectroscopic and chemical methods. Compound 2 showed moderate cytotoxicity against five human tumor cell lines in vitro with its EDso values ranging from 5.90-1 0.83 $\mu$g/mL.

키워드

참고문헌

  1. Alberto, M. J., Sanz-Cervera, J. F., Sancenon, F., Jakuovic J., Rustaiyan, A., and Mohamadi, F., Oplopanone derivatives and monoterpene glycosides from Artemisia sieberi. Phytochemistry, 34(4), 1061-1065 (1993) https://doi.org/10.1016/S0031-9422(00)90714-3
  2. An, D. K., Illastated Book of Korean medicinal Herbs, Kyohak- Sa, p 347 (1998)
  3. Antionio, G. G., Esteban, A. F., and Angel, G., R., Triterpenes from Maytenus Horrida. Phytochemistry, 26(10), 2785-2788 (1987) https://doi.org/10.1016/S0031-9422(00)83591-8
  4. Bolhmann, F. and Grenz, M., Terpeneglucoside aus Syneilesis aconitifolia. Phytochemistry, 16, 1057-1059 (1977) https://doi.org/10.1016/S0031-9422(00)86728-X
  5. Bolhmann, F. and Zdero, C., Neue furanoeremophilane und andere sesquiterpene aus vertretern gattung Europs. Phytochemistry, 17, 1135-1153 (1978) https://doi.org/10.1016/S0031-9422(00)94305-X
  6. Choi, S. Z., Kwon, H. C., Choi, S. U., and Lee, K. R., Five New Labdane Diterpenes from Aster oharai. J. Nat. Prod., 65(8), 1102-1106 (2002) https://doi.org/10.1021/np020119g
  7. Choi, S. Z., Lee, S. O., Choi, S. U., and Lee, K. R., A new sesquiterpene hydroperoxide from the aerial parts of Aster oharai. Arch. Pharm. Res., 26(7), 521-525 (2003) https://doi.org/10.1007/BF02976874
  8. Collado, I. G., Hanson, J. R., Hitchcock, P. B., and Macias- Sanchez, A. J., Streochemistry of epoxidation of some caryophyllenols. J. Org. Chem., 62, 1965-1969 (1997) https://doi.org/10.1021/jo9617979
  9. Kitagawa, I., Cui, Z., Son, B. W., Kobayashi, S., and Kyogoku, Y., Marine natural products. XVII. Nephtheoxydiol, a new cytotoxic hydroperoxy-germacrane, and related sesquiterpenoids from Okinawan coral of Nephthea sp. (Nephtheidae). Chem. Pharm. Bull., 35(1), 124-135 (1987) https://doi.org/10.1248/cpb.35.124
  10. Kuroda, C., Murae, T., Tada, M., Nagano, H., and Takahashi, T., New 14-oxofuranoeremophilanes and pelated sesquiterpenes from Syneilesis palmata (Thunb.) Maxim. Chem. Lett., 1313- 1316 (1978)
  11. Kwon, H. C., Cho, O. R., Lee, K. C., and Lee, K. R., Cerebrosides and terpene glycosides from the root of Aster scaber. Arch. Pharm. Res., 26(2), 132-137 (2003) https://doi.org/10.1007/BF02976658
  12. Lee Y. N., Flora of Korea 3rd edition, Kyohak-Sa, p 814 (1998)
  13. Manabu, H. and Tsutomu, F., Syneilesine, a new pyrrolizine alkaloid from Syneilesis palmata. Tetrahedron Lett., 41, 3657-3660 (1974)
  14. Mizutani, K., Yuda, M., Tanaka, O., Saruwatari, Y. I., Fuwa, T., Jia, M. R., Ling, Y. K., and Pu, X. F., Chemical studies on chinese traditional medicine, Dangshen. I. isolation of (Z)-3- and (E)-2-hexenyl $\beta$-D-glucosides. Chem. Pharm. Bull., 36(7), 2689-2690 (1988) https://doi.org/10.1248/cpb.36.2689
  15. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  16. Sung, T. V., Steffan, B., Steglich, W., Klebe, G., and Adam, G., Sesquiterpenoids from the roots of Homalomena aromatica. Phytochemistry, 31(10), 3515-3520 (1992) https://doi.org/10.1016/0031-9422(92)83719-F
  17. Tatarova, L. E., Korchabina, D. V., and Barkhash, V. A., Reactions of caryophyllene 4$\beta$,5$\alpha$-epoxide with carbonyl compounds on clay. Rus. J. Org. Chem., 38(4), 519-524 (2002) https://doi.org/10.1023/A:1016595005735
  18. Takeda, K., Minato, H., and Ishikawa, M., Studies on sesquiterpenoids- XII structure and absolute configuration of oplopanone, a new sesquiterpene from Oplopanax japonicus (Nakai) NAKAI. Tetrahedron suppl., 7, 219-225 (1965) https://doi.org/10.1016/S0040-4020(01)99108-2
  19. Vignon, M. R. and Vottero, J. A., $RMN^{13}$C : Sur l'utilisation des esters pour l'attribution des carbones des molecules glucidiques. Tetrahedron Lett., 28, 2445-2448 (1976)
  20. Ye, Q., Qin, G., and Zhao, W., Immunomodulatory sesquiterpene glycosides from Dendrobium nobile. Phytochemistry, 61, 885-890 (2002) https://doi.org/10.1016/S0031-9422(02)00484-3