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A Polyoxygenated Ellagitannin from Cercidiphyllum japonicum Bark

  • Lee, Min-Sung ;
  • Min, Hee-Jeong ;
  • Kim, Jin-Kyu ;
  • Bae, Young-Soo
  • Received : 2016.06.01
  • Accepted : 2016.07.07
  • Published : 2016.07.25

Abstract

Katsura tree (Cercidiphyllum japonicum Sieb. Et Zucc) bark was collected, air-dried and extracted with 70% aqueous acetone, then concentrated and sequentially fractionated using n-hexane, methylene chloride ($CH_2Cl_2$), ethylacetate (EtOAc), and $H_2O$. The $H_2O$ fraction was chromatographed on a Sephadex LH-20 column with various aqueous MeOH eluting solvents to isolate an ellagitannin. The isolate was elucidated as macabarterin, a polyoxygenated ellagitannin by NMR analysis, including HSQC, HMBC, Q-TOF MS, and with the comparison of authentic literature data. The compound was an ellagitannin which was isolated, for the first time, from the extracts of Katsura tree bark, and has never been reported before in domestic tree or plant sources.

Keywords

Cercidiphyllum japonicum bark;$H_2O$ fraction;macabarterin;ellagitannin;column chromatography

References

  1. Haslam, E. 1989. Plant polyphenols: Vegetable tannins revisited. Chemistry and Pharmacology of Natural Products. 90-146, University of Cambridge Oriental Publications.
  2. Isagi, Y., Kudo, M., Osumi, K., Sato, K., Sakio, H. 2005. Polymorphic microsatellite and markers for a relictual angiosperm Cercidiphyllum japonicum Sieb. et Zucc. and their utility for Cercidiphyllum magnificum. Mol. Ecol. Notes 5: 596-598. https://doi.org/10.1111/j.1471-8286.2005.01006.x
  3. Khallouki, F., Haubner, R., Hull, W.E., Erben, G., Spiegelhalder, B., Bartsch, H., Owen, R.W. 2007. Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. Food and Chemical Toxicology (45): 472-485.
  4. Kwon, D.J., Bae, Y.S. 2009. Ellagitannins from bark of Juglans mandshurica. Mokchae Konghak. 37(5): 480-485.
  5. Kwon, D.J. 2010. Chemical constituents and biological activities of certain Acer Species growing in Korea. Ph.D. Dissertation, pp. 211-221.
  6. Manchester, S.R., Chen, Z.D., Lu, A.M., Uemura, K. 2009. Eastern asian endemic seed plant genera and their paleogeographic history throughout the northern hemisphere. J. Syst. Evol. 47: 1-42. https://doi.org/10.1111/j.1759-6831.2009.00001.x
  7. Ngoumfo, R.M., Ngounou, G.E., Tchamadeu, C.V., Qadir, M.I., Mbazoa, C.D., Begum, A., Ngninzeko, F.N., Lontsi, D., Choudhary, M.I. 2008. Inhibitory Effect of Macabarterin, a Polyoxygenated Ellagitannin from Macaranga barteri, on Human Neutrophil Respiratory Burst Activity. American Chemical Society and American Society of Pharmacognosy. 71: 1906-1910.
  8. Sakanaka, S., Kim, M. Taniguchi, M., Yamamoto, T. 1989. Antibacterial substances in Japanese green tea extract against Streptococcus mutans, a cariogenic bacterium. Agricultural and Biological Chemistry (53): 2307-2311.
  9. Sepulveda, L., Ascacio, A., Raul, R.H., Antonio, A.C., Cristobal, N.A. 2011. Ellagic acid: Biological properties and Biotechnological development for production processes. African Journal of Biotechnology. 10(20): 4518-4523.
  10. Steinmetz, W.E. 2010 NMR assignment and characterization of proton exchange of the ellagitannin granatin B. Magnetic Resonance in Chemistry. 48: 565-570. https://doi.org/10.1002/mrc.2615
  11. Tada, M., Sakurai, K. 1991. Antimicrobial compound from Cercidiphyllum japonicum. Phytochemistry. 30(4): 1119-1120. https://doi.org/10.1016/S0031-9422(00)95184-7
  12. Takasugi, M., Katui, N. 1986. A biphenyl phytoalexin from Cercidiphyllum japonicum. Phytochemistry. 25(12): 2751-2752. https://doi.org/10.1016/S0031-9422(00)83734-6
  13. Towatari, K., Yoshida, K., Mori, N., Shimizu, K., Kondo, R., Sakai, K. 2002. Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells. Planta Med. 68: 995-998. https://doi.org/10.1055/s-2002-35657
  14. Xianbin, S., Gemma, L.T., Warren, R.J.D.G., David, S.S., Richard, J.S., David, R.S. 2009. Synthesis of Biaryl-Containing Medium-Ring Systems by Organocuprate Oxidation: Applications in the Total Synthesis of Ellagitannin Natural Products. Synthesis No.22, pp. 3880-3896.
  15. Yoshida, T., Hatano, T., Ito, H., Okuda, T., Quideau, S. 2009. Structural diversity and an timicrobial activities of ellagitannins. Chemistry and Biology of Ellagitannins. 55-93, World Scientific Publishing, Singapore.
  16. Zhang, X.Y., Yuan, X.Y., Ma, J., Yuan, L.J. 2009. Research on tissue culture and regeneration of Ceridiphyllum japonicum. Northern horticulture (9): 77-79 (in Chinese).

Cited by

  1. Chemical Constituents of the Flowers of Cercidiphyllum japonicum pp.1573-8388, 2019, https://doi.org/10.1007/s10600-019-02638-2

Acknowledgement

Supported by : Forest Science of Korean Forest Service