Ellagitannins from Bark of Juglans mandshurica

  • Kwon, Dong-Joo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University) ;
  • Bae, Young-Soo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University)
  • Received : 2009.07.24
  • Accepted : 2009.09.01
  • Published : 2009.09.25

Abstract

Juglans mandshurica bark was collected and extracted with 70% aqueous acetone. The extracts were concentrated and then sequentially fractionated using n-hexane, $CH_2Cl_2$, EtOAc, and $H_2O$ to be freeze dried. A portion of $H_2O$ fraction was chromatographed on a Sephadex LH-20 column using aqueous methanol to isolate (S)-2,3-HHDP-D-glucopyranoside (1). Some of EtOAc fraction was also treated on a Sephadex LH-20 column using aqueous methanol and EtOH-hexane mixture to purify pedunculagin (2). The structures of these two epimeric ellagitannins were elucidated by spectroscopic tools, NMR and MS.

Keywords

Acknowledgement

Supported by : Korea Forest Service

References

  1. Chang, J. H., J. H. Cho, H. H. Kim, K. P. Lee, M. W. Lee, S. S. Han, and D. I. Lee. 1995. Antitumor activity of pedunculagin, one of the ellagitannin. Archives of Pharmacal Research 18(6): 396-401 https://doi.org/10.1007/BF02976342
  2. Hobley, P., O. Howarth, and R. N. Ibbett. 1996. $^{1}H$ and $^{13}C$ NMR shifts for aldopyranose and aldofuranose monosaccharides: Conformational analysis and solvent dependence. Magnetic Resonance in Chemistry 34(10): 755$\sim$760 https://doi.org/10.1002/(SICI)1097-458X(199610)34:10<755::AID-OMR950>3.0.CO;2-U
  3. Kim, J. K., C. L. Si, and Y. S. Bae. 2006. Phenolic compounds from bark of Juglans mandshurica. Journal of Korean Wood Science and Technology 34(6): 51-60
  4. Kim, T. W. 1994. The Woody Plants of Korea in Color. Koyhak Press, Seoul, pp. 58-59
  5. Lee, I. R. and M. Y. Yang. 1994. Phenolic compounds from Duchesnea chrysantha and their cytotoxic activities in human cancer cell. Archives of Pharmacal Research 17(6): 476-479 https://doi.org/10.1007/BF02979129
  6. Li, G., M. L. Xu, H. G. Choi, S. H. Lee, Y. D. Jahng, C. S. Lee, D. C. Moon, M. H. Woo, and J. K. Son. 2003. Four new diarylpeptanoids from the roots of Juglans mandshurica. Chemical & Pharmaceutical Bulletin 51(3): 262-264 https://doi.org/10.1248/cpb.51.262
  7. Min, B. S., S. Y. Lee, J. H. Kim, J. K. Lee, J. J. Kim, D. H. Kim, Y. H. Kim, H. Joung, H. K. Lee, N. Nakamura, H. Miyashiro, and M. Hattori. 2003. Anti-complement activity of constituents from the stem bark of Juglans mandshruica. Biological & Pharmaceutical Bulletin 26(7): 1042-1044 https://doi.org/10.1248/bpb.26.1042
  8. Moharram, F. A., M. S. Marzouk, S. A. El-Toumy, A. A. Ahmed, and E. A. Aboutabl. 2003. Polyphenols of Melaleuca quinquenervia leaves- Pharmacological studies of grandinin. Phytotherapy Research 17(7): 767-773 https://doi.org/10.1002/ptr.1214
  9. Naoki, K., H. Ito, T. Hatano, and T. Yoshida. 2008. Phloroglucinol diglycosides accompanying hydrolyzable tannins from Kunzea ambigua. Phytochemistry 59(18): 3080-3086 https://doi.org/10.1016/j.phytochem.2008.03.003
  10. Si, C. L. and Y. S. Bae. 2007. Antioxidant effect of Juglans mandshurica bark gallotannins. Journal of Forest Science 23(1): 1-4
  11. Yoshida, T., T. Hatano, T. Okuda, M. U. Memon, T. Shingu, and K. Inoue. 1984. Spectral and chromatographic analyses of tannins. I. $^13C$ nuclear magnetic resonance spectra of hydrolyzable tannins. Chemical & Pharmaceutical Bulletin 32(5): 1790-1799 https://doi.org/10.1248/cpb.32.1790