Natural Product Sciences

  • 제26권2호
  • /
  • Pages.151-157
  • /
  • 2020
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  • 1226-3907(pISSN)
  • /
  • 2288-9027(eISSN)
한국생약학회 (The Korean Society of Pharmacognosy)
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Phytochemical Constituents of Phyllanthus urinaria

  • Cha, Joon Min (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Park, Jong Eel (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Choi, Sang Un (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang Ro (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
  • 투고 : 2020.03.17
  • 심사 : 2020.04.29
  • 발행 : 2020.06.30
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초록

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B5 (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B2 (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

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참고문헌

  1. Lee, Y. N. Flora of Korea; Kyohaksa: Korea, 1996, p 426.
  2. Lee, T. B. Coloured Flora of Korea vol. 1; Hyangmoonsa: Korea, 1998, p 672.
  3. Xu, M.; Zha, Z. Z.; Qin, X. L.; Zhang, X. L.; Yang, C. R.; Zhang, Y. J. Chem. Biodivers. 2007, 4, 2246-2252. https://doi.org/10.1002/cbdv.200790183
  4. Nguyen, V. T.: Phan, T. T. H.; Nguyen, H. N.; Nguyen, X. C.; Nguyen, P. T.; Bieke, D.; Andrea, G.; Yvan, V. H.; Joell, Q. L.; Chau, V. M. Phytochem. Lett. 2014, 7, 182-185. https://doi.org/10.1016/j.phytol.2013.11.013
  5. Chang, C. C.; Lien, Y. C.; Liu, K. C. S. C.; Lee, S. S. Phytochemistry 2003, 63, 825-833. https://doi.org/10.1016/S0031-9422(03)00371-6
  6. Skehan, P.; Stroreng, R.; Scudiero, D.; Monks, A.; Mcmahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112. https://doi.org/10.1093/jnci/82.13.1107
  7. Wu, X.; Liu, J.; Yu, Z. B.; Ye, Y. H.; Zhou, Y. W. Acta. Chim. Sin. 2007, 65, 1649-1653.
  8. Sarkar, T. K.; Mukherjee, B.; Ghosh, S. K. Tetrahedron 1998, 54, 3243-3254. https://doi.org/10.1016/S0040-4020(98)00069-6
  9. Otsuka, H.; Takeda, Y.; Yamasaki, K.; Takeda, Y. Planta Med. 1992, 58, 373-375. https://doi.org/10.1055/s-2006-961489
  10. Pauli, N.; Sequin, U.; Walter, A. Helv. Chim. Acta. 1990, 73, 578-582. https://doi.org/10.1002/hlca.19900730305
  11. Marino, S. D.; borbone, N.; Zollo, F.; Ianaro, A.; Meglio, D. P.; Iorizzi, M. J. Agric. Food Chem. 2004, 52, 7525-7531. https://doi.org/10.1021/jf048782t
  12. Yamamoto, M.; Akita, T.; Koyama, Y.; Sueyoshi, E.; Matsunami, K.; Otsuka, H.; Shinzato, T.; Takashima, A.; Aramoto, M.; Takeda, Y. Phytochemistry 2008, 69, 1586-1596. https://doi.org/10.1016/j.phytochem.2008.01.020
  13. Wang, M. Y.; Yang, Q.; Yan, X. X.; Wang, Q. L.; Wang, J. R.; Wang, Z. N.; Chem. Nat. Compd. 2017, 53, 963-965. https://doi.org/10.1007/s10600-017-2170-5
  14. Y ajima, A .; O ono, Y.; N akagawa, R.; N u kada, T.; Yabuta, G. Bioorg. Med. Chem. 2009, 17, 189-194. https://doi.org/10.1016/j.bmc.2008.11.002
  15. Wei, K.; Li, W.; Koike, K.; Liu, L.; Fu, X.; Lin, L.; Chen, Y.; Nikaido, T. Chem. Pharm. Bull. 2004, 52, 776-779. https://doi.org/10.1248/cpb.52.776
  16. Su, L.; Wang, Y. M.; Zhong, K. R.; Tu, G. Z.; Jiang, Y. Y.; Liu, B. Chem. Nat. Compd. 2019, 55, 351-353. https://doi.org/10.1007/s10600-019-02688-6
  17. Yoshikawa, M.; Shimada, H.; Saka, M.; Yoshizumi, S.; Yamahara, J.; Matsuda, H. Chem. Pharm. Bull. 1997, 45, 464-469. https://doi.org/10.1248/cpb.45.464
  18. Matsunami, K.; Nagashima, J.; Sugimoto, S.; Otsuka, H.; Takeda, Y.; Lhieochaiphant, D.; Lhieochaiphant, S. J. Nat. Med. 2010, 64, 460-467. https://doi.org/10.1007/s11418-010-0434-5
  19. Kim, K. H.; Lee, K. H.; Choi, S. U.; Kim, Y. H.; Lee, K. R. Arch. Pharm. Res. 2008, 31, 983-988. https://doi.org/10.1007/s12272-001-1256-8
  20. Kim, Y. C.; Kingston, D. G. I. J. Nat. Prod. 1996, 59, 1096-1098. https://doi.org/10.1021/np960164m
  21. Miyase, T.; U eno, A .; Takizawa, N.; K obayashi, H .; Oguchi, H. Chem. Pharm. Bull. 1987, 35, 3713-3719. https://doi.org/10.1248/cpb.35.3713
  22. Morikawa, H.; Kasai, R.; Otsuka, H.; Hirata, E.; Shinzato, T.; Aramoto, M.; Takeda, Y. Chem. Pharm. Bull. 2004, 52, 1086-1090. https://doi.org/10.1248/cpb.52.1086
  23. Kim, M. R.; Lee, S. K.; Kim, C. S.; Kim, K. S.; Moon, D. C. Arch. Pharm. Res. 2004, 27, 1029-1033. https://doi.org/10.1007/BF02975426
  24. Perkins, S. J.; Johnson, L. N.; Phillips, D. C. Carbohydr. Res. 1977, 59, 19-34. https://doi.org/10.1016/S0008-6215(00)83289-9
  25. Kim, C. S.; Subedi, L.; Park, K. J.; Kim, S. Y.; Choi, S. U.; Kim, K. H.; Lee, K. R. Fitoterapia 2015, 106, 147-152. https://doi.org/10.1016/j.fitote.2015.08.013
  26. Kikuzaki, H.; Miyajima, Y.; Nakatani, N. J. Nat. Prod. 2008, 71, 861-865. https://doi.org/10.1021/np0705615
  27. Vick, B. A.; Zimmerman, D. C. Biochem. Biophys. Res. Commun. 1983, 111, 470-477. https://doi.org/10.1016/0006-291X(83)90330-3
  28. Miersch, O.; Preiss, A.; Sembdner, G.; Schreiber, K. Phytochemistry 1987, 26, 1037-1039. https://doi.org/10.1016/S0031-9422(00)82345-6
  29. Kramell, R.; Schneider, G.; Miersch, O. Phytochem. Anal. 1996, 7, 209-212. https://doi.org/10.1002/(SICI)1099-1565(199607)7:4<209::AID-PCA292>3.0.CO;2-H