YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Cytotoxic Constituents of Rhododendron brachycarpum

만병초의 세포독성 성분

  • Jang Gi Uk (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University) ;
  • Choi Sang Un (Korea Research Institute of Chemical Technology) ;
  • Lee Kang Ro (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University)
  • 장기욱 (성균관대학교 약학대학 천연물 약품 화학 연구실) ;
  • 최상운 (한국화학연구소) ;
  • 이강노 (성균관대학교 약학대학 천연물 약품 화학 연구실)
  • Published : 2005.06.01
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Abstract

From the methanol extract of Rhododendron brachycarpum four triterpenes, three phenylpropanes and a diterpene alkaloid were isolated. Their structures were identified as glutinol (1), 3$\beta$-hydroxyurs-12-ene (2), $\beta$-sitosterol (3), (E)-P-hydrox-ycinnamic acid hexadecylester (4), (-)-rhododendrol (5), (+)-rhododendrol (6), 3$\beta$-hydroxyurs-12-en-28-oic acid (7) and gray-anotoxin I (8) by spectroscopic methods. Compound 8 showed moderate cytotoxicity against five cultured human tumor cell lines with $ED_{50}$ values of $3.21\~4.05 {\mu}g/ml$. The other compounds were of marginal activity against the tested cell lines.

Keywords

References

  1. Lee, Y. N. : Flora of Korea 3rd ed., Kyohak, p. 383 (1998)
  2. Choi, J. S., Young, H. S., Park, J. C., Choi, J. H. and Woo, W. S. : Flavonoids from the leaves of Rhododendron brachycarpum. Arch. Pharm. Res. 9, 233 (1986) https://doi.org/10.1007/BF02856638
  3. Youn, H. S. and Cho, J. H. : Isolation and structure elucidation of triterpenoidal constituents from the leaves of Rhododondron brachycarpum. Kor. J. Pharmacogn. 22, 18 (1991)
  4. Lozyuk, L. V. : Antiviral properties of some compounds of plants origin. Mikrobiologichnii Zhurnal. 39, 343 (1997)
  5. Antionio, G. G., Esteban, A. F. and Angel, G. R. : Triterpenes from maytenus horrida. Phytocemistry 26, 2785 (1987) https://doi.org/10.1016/S0031-9422(00)82332-8
  6. Shashi, B. M. and Asish, P. K. : $^{13}C$ NMR spectra of pentacyclic triterpenoids - a compilcation and some salient features. Phytochemistry 37, 1517 (1994) https://doi.org/10.1016/S0031-9422(00)89569-2
  7. Shashi, B. M., Ashoke, K. N. and Gita, R. : Triterpenoids. Phytochemistry 31, 2199 (1992) https://doi.org/10.1016/0031-9422(92)83257-Y
  8. Manik, C. D. and Shashi, B. M. : Triterpenoids. Phytochemistry 22, 1071 (1983) https://doi.org/10.1016/0031-9422(83)85036-5
  9. Uwe, K., Mack, K. and Heinz, S. : Isolation and structure elucidation of p-hydroxycinnamic acid esters from the rhizome of Agropyron reoens. Planta Medica 59, 279 (1993) https://doi.org/10.1055/s-2006-959672
  10. Maurice, E. S., Emma, S. D. and Stanley, J. K. : Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweetpotato [Ipomoea batats (L.) Lam.] J. Agric. Food Chem. 42, 2589 (1994). https://doi.org/10.1021/jf00047a041
  11. Hefeng, P. and Lennart, N. L. : Rhododendrol glycosides and phenyl glucoside esters from inner bark Betula pubescens. Phytochemistry 36, 79 (1994) https://doi.org/10.1016/S0031-9422(00)97017-1
  12. Martina, K. and Meinhart, H. Z. : Stereochemistry of cmethylation in the biosynthesis of rhododendrin in Alnus and Betula. Phytochemistry 17, 1281 (1978) https://doi.org/10.1016/S0031-9422(00)94574-6
  13. Das, B., Padama, R. S., Srinivas, K. V. N. S. and Yadav, J. S. : Stereospecific synthesis and absolute configuration of (+)-rhododendrol. Phytochemistry 33, 1529 (1993) https://doi.org/10.1016/0031-9422(93)85127-D
  14. Alex, C., Maysa, F., Laurence, B. D., Jaroslav, Z., Tower, G. H. N., Chantal, M. S., Steven, J. R., Rodney, C. and Norman, G. L. : Phenylbutanoid and taxane-like metabolites from needles of Taxus breuifolia. Phytochemistry 36, 975 (1994) https://doi.org/10.1016/S0031-9422(00)90475-8
  15. Takashi, F., Hitoshi, H., Taisuke, I. and Shin-ichi, T. : Bioconversion of rhododendrol by Acer nikoense. Phytochemistry 39, 1085 (1995) https://doi.org/10.1016/0031-9422(95)00102-D
  16. Masayoshi, K., Masahiro, N. and Takao, I. : Studies on the constituents of Aceraceae plants. IV. Carbon-13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol and related compounds, and structure of aceroside IV from acer nikoense. Chem. Pharm. Bull. 31, 1917 (1983) https://doi.org/10.1248/cpb.31.1917
  17. Elita, S., Lennart, N. L. and Rolf, A. : Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry 32, 365 (1993) https://doi.org/10.1016/S0031-9422(00)94995-1
  18. Choi, J. S., Young, H. S., Park, J. C., Choi, J. H. and Woo, W. S. : Further study on the constituents of Rhododendron bracchycarpum. Arch. Pharm. Res. 10, 169 (1987) https://doi.org/10.1007/BF02861908
  19. James, A. K., Mei-Ying, H., Shin-Foon, C. and Iaso, K. : Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle. Phytochemistry 30, 1797 (1991) https://doi.org/10.1016/0031-9422(91)85015-R