Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Potentially Bioactive Two New Natural Sesquiterpenoids from the Rhizomes of Zingiber zerumbet

  • Jang Dae Sik (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Seol Eun Kyoung (College of Pharmacy, Ewha Womans University)
  • Published : 2005.03.01
Download PDF
⟨ Previous Next ⟩

Abstract

Repeated chromatography of the n-hexane-soluble fraction of the MeOH extract of the rhizomes of Zingiber zerumbet led to the isolation of two isomers of 6-methoxy-2E,9E-humula-dien-8-one (1 and 2) and stigmast-4-en-3-one. The structures of 1 and 2 were determined by spectroscopic methods including 10 and 2D-NMR elucidated by analysis of spectroscopic data as well as by comparison with published values. This is the first report on the isolation of compounds 1 and 2 from the nature. Stigmast-4-en-3-one was first isolated from this plant.

Keywords

References

  1. Bohlmann F. and Pauls A., Humulane derivatives from Nauplius intermedius. Phytochemistry, 31, 1663-1665 (1992) https://doi.org/10.1016/0031-9422(92)83124-H
  2. Dai, J. R., Cardellina II, J. H., McMahon, J. B., and Boyd, M. R., Zerumbone, an HIV-inhibitory and cytotoxic sesquiterpene of Zingiber aromaticum and Z. zerumbet. Nat. Prod. Lett., 10, 115-118 (1997) https://doi.org/10.1080/10575639708043725
  3. Farnsworth, N. R. and Bunyapraphatsara, N., Thai Medicinal Plants. Prachachon, Bangkok, Thailand, pp. 261-263 (1992)
  4. Gupta, V. N., Kataky, J. C. S., and Mathur, R. K., Zerumbone from Zingiber zerumbet Sm. Indian J. Chem. B, 18B, 290- 291 (1979)
  5. Jang, D. S., Han A. R., Park, G., and Seo, E. K., Flavonoids and aromatic compounds from the rhizomes of Zingiber zerumbet. Arch. Pharm. Res., 27, 386-389 (2004) https://doi.org/10.1007/BF02980078
  6. Kitayama, T., Okamoto, T., Hill, R. K., Kawai, Y., Takahashi, S., Yonemori, S., Yamamoto Y., Ohe, K., Uemura, S., and Sawada, S., Chemistry of zerumbone. 1. Simplified isolation, conjugate addition reactions, and a unique ring contracting transannular reaction of its dibromide. J. Org. Chem., 64, 2667-2672 (1999) https://doi.org/10.1021/jo981593n
  7. Kitayama, T., Yamamoto, K., Utsumi, R., Takatani, M., Hill, R. K., Kawai, Y., Sawada, S., and Okamoto, T., Chemistry of zerumbone. 2. Regulation of ring bond cleavage and unique antibacterial activities of zerumbone derivatives. Biosci. Biotechnol. Biochem., 65, 2193-2199 (2001) https://doi.org/10.1271/bbb.65.2193
  8. Masuda, T., Jitoe, A., Kato, S., and Nakatani, N., Constituents of Zingiberaceae. Part 3. Acetylated flavonol glycosides from Zingiber zerumbet. Phytochemistry, 30, 2391-2392 (1991) https://doi.org/10.1016/0031-9422(91)83656-6
  9. Matthes, H. W. D., Luu, B., and Ourisson, G., Chemistry and Biochemistry of Chinese drugs. Part VI. Cytotoxic components of Zingiber zerumbet, Curcuma zedoaria and C. domestica. Phytochemistry, 19, 2643-2650 (1980) https://doi.org/10.1016/S0031-9422(00)83937-0
  10. Murakami, A., Takahashi, D., Kinoshita, T., Koshimizu, K., Kim, H. W., Yoshihiro, A., Nakamura, Y., Jiwajinda, S., Terao, J., and Ohigashi, H., Zerumbone, a southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis: The $\alpha$,$\beta$-unsaturated carbonyl group is a prerequisite. Carcinogenesis, 23, 795- 802 (2002) https://doi.org/10.1093/carcin/23.5.795
  11. Seca, A. M. L., Silva, A. M. S., Silvestre, A. J. D., Cavaleiro, J. A. S., Domingues, F. M. J., and Neto, C. P., Chemical composition of the light petroleum extract of Hibiscus cannabinus bark and core. Phytochem. Anal., 11, 345-350 (2000) https://doi.org/10.1002/1099-1565(200011/12)11:6<345::AID-PCA540>3.0.CO;2-T
  12. Tanaka, T., Shimizu, M., Kohno, H., Yoshitani, S. -I., Tsukio, Y., Murakami, A., Safitri, R., Takahashi, D., Yamamoto, K., Koshimizu, K., Ohigashi, H., and Mori, H., Chemoprevention of azoxymethane-induced rat aberrant crypt foci by dietary zerumbone isolated from Zingiber zerumbet. Life Sci., 69, 1935-1945 (2001) https://doi.org/10.1016/S0024-3205(01)01277-2