Hydrolysable Tannins from Cercidiphyllum japonicum Bark

Lee, Min-Sung;Min, Hee-Jeong;Si, Chuan-Ling;Bae, Young-Soo

  • Received : 2016.06.01
  • Accepted : 2016.07.07
  • Published : 2016.07.25


The EtOAc and $H_2O$ soluble fractions of Katsura tree (Cercidiphyllum japonicum Sieb. Et Zucc) bark extracts were chromatographed on a Sephadex LH-20 column with various aqueous MeOH. Gallic acid (1), methyl galate (2), kurigalin (3), 1,2,3,6-tetra-O-galloyl-${\beta}$-D-glucose (4) and 1,2,3,4,6-penta-O-galloyl-${\beta}$-D-glucose (5) were isolated from EtOAc fraction. Isocorilagin (6) and methyl galate (2) were separated from $H_2O$ fraction. The structure determination was done by $^1H$ and $^{13}C$ NMR. Of these isolated compounds, methyl galate (2), kurigalin (3) and isocorilagin (6) were isolated, for the first time, from the bark extracts of Cercidiphyllum japonicum.


Katsura tree (Cercidiphyllum japonicum) bark;Hydrolysable tannins;gallotannin;ellagitannin;column chromatography


  1. Chung, S.K., Nam, J.A., Jeon, S.Y., Kim, S.I., Lee, H.J., Chung, T.H., Song, K.S. 2003. A prolyl endopeptidase-inhibiting antioxidant from Phyllanthus ussurensis. Archives of Pharmacal Research 26(12): 1024-1028.
  2. Duan, D., Li, Z., Luo, H., Zhang, W., Chen, L., Xu, X. 2004. Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease. Bioorg Med Chem Lett 14: 6041-6044.
  3. 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.
  4. Anderson, O.M., Markham, K.R. 2006. Flavonoids: Chemistry, Biochemistry and Applications. Taylor & Francis, New York.
  5. Cammann, J., Denzel, K., Schilling, G., Gross, G.G. 1989. Biosynthesis of gallotannins: ${\beta}$-Glucogallindependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,4-tetragalloylglucose. Archives of Biochemistry and Biophysics 273: 58-63.
  6. Kador, P.F., Robison, W.G., Kinoshita, J.H. 1985a. The pharmacology of aldose reductase inhibitors. Annu. Rev. Pharmacol. Toxicol. 25: 691-714.
  7. Kador, P.J., Konishita, J.H., Sharpless, N.E. 1985b. Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications. J. Med. Chem. 28: 841-849.
  8. Kashiwada, Y., Nonaka, G., Nishioka, I. 1988. Galloylsucroses from Rhubarbs. Phytochemistry 27: 1469-1472.
  9. Kwon, D.J. 2010. Chemical constituents and biological activities of certain Acer Species growing in Korea. Ph.D. Dissertation, 211-221.
  10. Kwon, D.J., Bae, Y.S. 2009. Ellagitannins from bark of Juglans mandshurica. Mokchae Konghak. 37(5): 480-485.
  11. Lampire, O., Mila, I., Raminosoa, M., Michon, V., Herve, C., Penhoat, D., Faucheur, N., Laprevote, O., Scalbert, A. 1998. Polyphenols isolated from the bark of Castanea sativa Mill. Chemical structures and auto-association. Phytochemistry 49: 623-631.
  12. Latte, K.P., Kolodziej, H. 2000. Pelargoniins, new ellagitannins from Pelargonium reniforme. Phytochemistry 54(7): 701-708.
  13. Lee, H.Y., Jeong, H.S. 2005. Isolation and identification of antimicrobial substance from Canavalia gladiata. Food Science and Biotechnology 14(2): 268-274.
  14. Lee, T.S., Bae, Y.S. 2015. A Gallotannin from Cercidiphyllum japonicum Leaves. J. Korean Wood Sci. Technol. 43(5): 558-565.
  15. Liu, X., Cui, C., Zhao, M., Wang, J., Luo, W., Yang, B., Jiang, Y. 2008. Identification of phenolics in the fruit of emblica and their antioxidant activities. Food Chemistry 109(4): 909-915.
  16. Luo, W., Zhao, M., Yang, B., Shen, G., Rao, G. 2009. Identification of bioactive compounds in Phyllenthus emblica L. fruit and their free radical scavenging activities. Food chemistry 114(2): 499-504.
  17. Williamson, J., Kilo, C., Tilton, R.G. 1992. Mechanism of glucose and diabetes-induced vascular dysfunction. In N. Ruderman, J. Brownlee and J. Williamson (eds.), hyperglycemia, diabetes, and vascular disease. American physiology society. New York, pp. 107-132.
  18. 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.
  19. 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).
  20. 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.
  21. Niehaus, J.U., Gross, G.G. 1997. A gallotannin degrading esterase from laves of Pedunculate oak. Phytochemistry 45(8): 1555-1560.
  22. Niemetz, R., Gross, G.G. 2001. Gallotannin biosynthesis: ${\beta}$-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry 58: 657-661.
  23. Nonaka, G., Ishimatsu, M., Ageta, M., Nishioka I. 1989. Tannins and related compounds. LXXVI. Isolation and Characterization of Cercidinins A and B and Cuspinin, Unusual 2,3-(R)-Hexahydroxydiphenoyl Glucoses from Cercidiphyllum japonicum and Castanopsis Cspidata var. sieboldii. Chem. Pharm. Bull. 37(1): 50-53.
  24. Ozawa, T., Kobayashi, S., Seki, R., Imagawa, H. 1984. A new gallotannin from bark of chestnut tree, Castanea crenata Sieb. et Zucc. Agric Biol Chem 48: 1411-1416.
  25. Owen, R.W., Haubner, R., Hull, W.E., Erben, G., Spiegelhalder, B., Bartsch, H., Haber, B. 2003. Isolation and structure elucidantion of the major individual polyphenols in carob fibre. Food and Chemical Toxicology 41: 1727-1738.
  26. Saijo, R., Nonaka, G.I., Nishioka, I. 1990. Gallica acid esters of bergenin and norbergenin from Mallotus Japonicus. Phytochemistry 29: 267-270.
  27. Sancheti, S., Sancheti, S., Bafna, M., Seo, S.Y. 2011. 2,4,6-Trihydroxybenzaldehyde as a potent antidiabetic agent alleviates postprandial hyperglycemia in normal and diabetic rats. Medicinal Chemistry Research. 20: 1181-1187.
  28. 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.
  29. Steinmetz, W.E. 2010 NMR assignment and characterization of proton exchange of the ellagitannin granatin B. Magnetic Resonance in Chemistry. 48: 565-570.
  30. Tada, M., Sakurai, K. 1991. Antimicrobial compound from Cercidiphyllum japonicum. Phytochemistry 30(4): 1119-1120.
  31. Takasugi, M., Katui, N. 1986. A biphenyl phytoalexin from Cercidiphyllum japonicum. Phytochemistry 25(12): 2751-2752.
  32. Tanaka, T., Nonaka, G., Nishioka, I. 1985. Punicafolin, an ellagitannin from the leaves of Punica grantum. Phytochemistry 24: 2075-2078.
  33. Towatari, K., Yoshida, K., Mori, N., Shimizu, K.,Kondo, R., Sakai, K. 2002. Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on prolifefation of mouse hair epithelial cells. Planta Medica 68: 995-998.
  34. Wang, D., Kasuga, J., Kuwabara, C., Endoh, K., Fukushi, Y., Fujikawa, S., Arakawa, K. 2012. Presence of supercooling-facilitating hydrolyzable tannins in deep supercooling xylem parenchyma cells in Cercidiphyllum japonicum. Planta 235: 747-759.

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Supported by : Forest Science of Korean Forest Service