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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.

참고문헌 (20)

  1. 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) 
  2. 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) 
  3. 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) 
  4. 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) 
  5. 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) 
  6. 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) 
  7. 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) 
  8. Lee Y. N., Flora of Korea 3rd edition, Kyohak-Sa, p 814 (1998) 
  9. 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) 
  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. An, D. K., Illastated Book of Korean medicinal Herbs, Kyohak- Sa, p 347 (1998) 
  12. Antionio, G. G., Esteban, A. F., and Angel, G., R., Triterpenes from Maytenus Horrida. Phytochemistry, 26(10), 2785-2788 (1987) 
  13. Bolhmann, F. and Zdero, C., Neue furanoeremophilane und andere sesquiterpene aus vertretern gattung Europs. Phytochemistry, 17, 1135-1153 (1978) 
  14. 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) 
  15. 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) 
  16. Manabu, H. and Tsutomu, F., Syneilesine, a new pyrrolizine alkaloid from Syneilesis palmata. Tetrahedron Lett., 41, 3657-3660 (1974) 
  17. Ye, Q., Qin, G., and Zhao, W., Immunomodulatory sesquiterpene glycosides from Dendrobium nobile. Phytochemistry, 61, 885-890 (2002) 
  18. 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) 
  19. 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) 
  20. Bolhmann, F. and Grenz, M., Terpeneglucoside aus Syneilesis aconitifolia. Phytochemistry, 16, 1057-1059 (1977) 

이 논문을 인용한 문헌 (5)

  1. 2007. "" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, 30(9): 1067~1074 
  2. 2008. "" Natural product sciences, 14(2): 100~106 
  3. 2009. "" Natural product sciences, 15(1): 44~49 
  4. Lee, Yang-Suk ; Seo, Soo-Jung ; Kim, Nam-Woo 2009. "Analysis of the General Components of Syneilesis palmata Maxim" 한국식품저장유통학회지 = Korean journal of food preservation, 16(3): 412~418 
  5. Lee, Yang-Suk ; Kim, Nam-Woo 2014. "Antioxidant activities of hot water extract of Syneilesis palmata root and aerial part" 한국식품저장유통학회지 = Korean journal of food preservation, 21(1): 9~16 


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