Reverse-Phase HPLC Method for Identification of Diastereomeric Constituents from Sasa borealis

Sasa borealis의 Diastereomeric 성분들의 역상 고속액체크로마토그래프 분석방법

  • 정연희 (이화여자대학교 약학대학) ;
  • 이준 (이화여자대학교 약학대학) ;
  • 권영주 (이화여자대학교 약학대학) ;
  • 서은경 (이화여자대학교 약학대학)
  • Published : 2006.02.01

Abstract

Reiterated normal-phase column chromatography lead to the isolation and purification of six known compounds but for the first time from the whole plant of Sasa borealis (Hack.) Makino (Gramineae): tricin 4'-O-(erythro-${\beta}$-guaia-cylglyceryl) ether (1), tricin 4'-O-(threo-${\beta}$-guaiacylglyceryl) ether (2), tricin 4'-O-[erythro-${\beta}$-guaiacyl-(9'-O-acetyl)-glyceryl] ether (3), tricin 4'-O-[threo-${\beta}$-guaiacyl-(9'-O-acetyl)-glyceryl] ether (4), (-)-pinoresinol (5), and vanillin (6). The structures of the compounds (1-6) were established based on interpretation of high resolution NMR (COSY, HSQC, HMBC, and NOESY) spectral data. In particular, compounds 1 and 3 were diastereomers of compounds 2 and 4, respectively. These two sets of diastereomers were able to be simultaneously identified and quantified by a gradient reversed-phase HPLC method with UV photodiode array, This sensitive HPLC method is noteworthy as a simultaneous separation and identification method to test the extract of the family Gramineae which contains these compounds.

Keywords

References

  1. Koh, K. S. and Jeon, E. S. : Ferns, Fern-Allies and seed-bearing plants of Korea. Iljinsa, Seoul (2003)
  2. Ohmoto, T. and Ikuse, M. : Triterpenoids of the Gramineae. Phytochemistry 9, 2137 (1970) https://doi.org/10.1016/S0031-9422(00)85379-0
  3. Yoon, K. D., Kim, C. Y. and Heo, H. : The flavone glycosides of Sasa borealis. Kor. J. Pharmacogn. 31, 224 (2001)
  4. Nakajima, Y., Young, S. Y. and Kunugi, A. : Six new flavonolignans from Sasa veitchii Rehder. Tetrahedron 59, 8011 (2003) https://doi.org/10.1016/j.tet.2003.08.026
  5. Wenzig, E., Kunert, O., Ferreira, D., Schmid, M., Schuhly, W., Bauer, R. and Hiermann, A. : Flavonolignans from Avena sativa. J. Nat. Prod. 68, 289 (2005)
  6. Bouaziz, M., Veitch, N. C., Grayer, R. J., Simmonds, M. S. J. and Damak, M. : Flanovolignans from Hyparrhenia hirta. Phytochemistry 60, 515 (2002) https://doi.org/10.1016/S0031-9422(02)00145-0
  7. Zhuang, L. G., Seligmann, O., Jurcic, L. and Wagner, H. : Inhaltsstoffe von Daphne tangutica. Planta Medecia 45, 172 (1982) https://doi.org/10.1055/s-2007-971368
  8. Jang, D. S., Han, A. R., Park, K. W. N., Jhon, G. J. and Seo, E. K. : Flavonoids and aromatic compounds from the rhizomes of Zingiber zerumbet. Arch. Pharm. Res. 27, 386 (2004) https://doi.org/10.1007/BF02980078
  9. Braga, A. C. H., Zacchino, S., Badano, H., Sierra, M. G. and Ruveda, E. A. : 13C NMR spectral and conformation analysis of 8-O-4' neolignans. Phytochemistry 23, 2025 (1984) https://doi.org/10.1016/S0031-9422(00)84963-8
  10. Ren, M., Reilly, R. T. and Sacchi, N. : Sasa health exerts a protective effect on Her2/NeuN mammary tumorigenesis. Anticancer Res. 24, 2879 (2004)
  11. Duan, H., Takishi, Y., Momota, H., Ohmoto, Y. and Taki, T. : Immunosuppressive constituents from Saussurea medusa. Phytochemistry 59, 85 (2002) https://doi.org/10.1016/S0031-9422(01)00429-0
  12. Ando, H., Ohba, H., Sakaki, T., Takamine, K., Kamino, Y., Moriwaki, S., Bakalova, R., Uemura, Y. and Hatate, Y. : Hotcompressed- water decomposed products from bamboo manifest a selective cytotoxicity against acute lymphoblastic leukemia cells. Toxicol In Vitro. 18, 765 (2004) https://doi.org/10.1016/j.tiv.2004.03.011
  13. Lu, B., Wu, X., Tie, X., Zhang, Y. and Zhang, Y. : Toxicology and safety of anti-oxidant of bamboo leaves. Part 1 : Acute and subchronic toxicity studies on anti-oxidant of bamboo leaves. Food Chem. Toxicol. 43, 783 (2005) https://doi.org/10.1016/j.fct.2005.01.019
  14. Syrchina, A. I., Gorshkov, A. G., Shcherbakov, V. V., Zinchenko, A. L., Vereshchagin, S. V., Zaikov, K. L. and Semenov, A. A. : Flavonolignans of Salsola collina. Khimiya Prirodnykh Soedinenii 28, 182 (Engl. Trans., Chemistry of Natural Compounds 28, 155, (1992)
  15. Guz, N. R. and Stermitz, F. R. : Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans. J. Nat. Prod. 63, 1140 (2000) https://doi.org/10.1021/np000166d