DOI QR코드

DOI QR Code

Chemical Constituents of Fermented Noni (Morinda citrifolia) Juice Exudates and Their Biological Activity

  • Youn, Ui Joung (Division of Life Sciences, Korea Polar Research Institute, KIOST) ;
  • Chang, Leng Chee (Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo)
  • Received : 2016.09.28
  • Accepted : 2016.11.01
  • Published : 2017.03.31

Abstract

In a continuing study of the fermented noni (Morinda citrifolia) juice exudates, five compounds, heptanyl $2-O-{\beta}-{\small{D}}-xylofuranosyl-(1{\rightarrow}6)-{\beta}-{\small{D}}-glucopyranoside$ (1), n-butyl ${\beta}-{\small{D}}-glucopyranoside$ (2), (1S)-(3-ethenyl-phenyl)-1,2-ethanediol (3), (2S)-2-hydroxybutanedioic acid (4), and daucosterol (5) were isolated from the buthanol partition of the extract. The structures of the isolates were identified by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with the published values. Among the isolates, compounds 1 - 3 were isolated for the first time from the plant species. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production and tumor necrosis factor alpha ($TNF-{\alpha}$)-induced $NF-{\kappa}B$ activity, and quinonone reductase-1 (QR1)-inducing effect.

Keywords

References

  1. Wang, M.Y.; West, B. J.; Jensen, C. J.; Nowicki, D.; Su, C.; Palu, A. K.; Anderson, G. Acta Pharmacol. Sin. 2002, 23, 1127-1141.
  2. Hirazumi, A.; Furusawa, E.; Chou, S. C.; Hokama, Y. Proc. West Pharmacol. Soc. 1996, 39, 7-9.
  3. Palu, A. K.; Kim, A. H.; West, B. J.; Deng, S.; Jensen, J.; White, L. J. Ethnopharmacol. 2008. 115, 502-506. https://doi.org/10.1016/j.jep.2007.10.023
  4. Yang, J.; Paulino, R.; Janke-Stedronsky, S.; Abawi, F. Food Chem. 2007. 102, 302-308. https://doi.org/10.1016/j.foodchem.2006.05.020
  5. Jain, R. K.; Srivastava, S. D. Proc. Nat. Acad. Sci. India 1992, 62A, 11-13.
  6. Deng, Y.; Chin, Y. W.; Chai, H.; Keller, W. J.; Kinghorn, A. D. J. Nat. Prod. 2007, 70, 2049-2052. https://doi.org/10.1021/np070501z
  7. Srivastava, M.; Singh, J. Int. J. Pharmacog. 1993, 31, 182-184. https://doi.org/10.3109/13880209309082938
  8. Liu, G.; Bode, A.; Ma, W. Y.; Sang, S.; Ho, C. T.; Dong, Z. Cancer Res. 2001, 61, 5749-5756.
  9. Su, B. N.; Pawlus, A. D.; Jung, H. A.; Keller, W. J.; McLaughlin, J. L.; Kinghorn, A. D. J. Nat. Prod. 2005, 68, 592-595. https://doi.org/10.1021/np0495985
  10. Kanchanapoom, T.; Kasai, R.; Yamasaki, K. Phytochemistry 2002, 59, 551-556. https://doi.org/10.1016/S0031-9422(01)00426-5
  11. Sang, S.; Cheng, X.; Zhu, N.; Wang, M.; Jhoo, J. W.; Stark, R. E.; Badmaev, V.; Ghai, G.; Rosen, R. T.; Ho, C.T. J. Nat. Prod. 2001, 64, 799-800. https://doi.org/10.1021/np010011l
  12. Youn, U. J.; Park, E. J.; Kondratyuk, T. P.; Sang-Ngern, M.; Wall, M. M.; Wei, Y.; Pezzuto, J. M.; Chang, L. C. J. Nat. Prod. 2016, 79, 1508-1513. https://doi.org/10.1021/acs.jnatprod.5b00970
  13. Kondratyuk, T. P.; Park, E. J.; Yu, R.; van Breemen, R.B.; Asolkar, R. N.; Murphy, B. T.; Fenical, W.; Pezzuto, J. M. Mar. Drugs 2012, 1, 451-464.
  14. Park, E.J.; Kondratyuk, T. P.; Morrell, A.; Kiselev, E.; Conda-Sheridan, M.; Cushman, M.; Ahn, S.; Choi, Y.; White, J.J.; van Breemen, R.B.; Pezzuto, J.M. Cancer Prev. Res (Phila). 2011, 4, 592-607. https://doi.org/10.1158/1940-6207.CAPR-10-0004
  15. Song, L. L.; Kosmeder II, J. W.; Lee, S. K.; Gerhauser, C.; Lantvit, D.; Moon, R. C.; Moriarty, R. M.; Pezzuto, J. M. Cancer Res. 1999, 59, 578-585.
  16. Chiang, Y.M.; Chuang, D.Y.; Wang, S.Y.; Kuo, Y.H.; Tsai, P.W.; Shyur, L.F. J. Ethnopharmacol. 2004, 95, 409-419. https://doi.org/10.1016/j.jep.2004.08.010
  17. Yu, H.L.; Xu, J.H.; Lu, W.Y.; Lin, G.Q. Enzyme Microb. Tech. 2007, 40, 354-361. https://doi.org/10.1016/j.enzmictec.2006.05.004
  18. Yang, W.Q.; Qin, X.D.; Shao, H.J.; Fang, L.Z.; Wang, F.; Ding, Z.H.; Dong, Z.J.; Liu, J.K. J. Basic Microbiol. 2007, 47, 191-193. https://doi.org/10.1002/jobm.200610260
  19. Boger, D. L.; Panek, J. S. J. Org. Chem. 1981, 46, 1208-1210. https://doi.org/10.1021/jo00319a034
  20. Faizi, S.; Ali, M.; Saleem, R.; Irfanullah.; Bibi, S. Magn. Reson. Chem. 2001, 39, 399-4-21405. https://doi.org/10.1002/mrc.855
  21. Choudhary, A.; Kumar, R.; Srivastava, R. B.; Surapaneni, S. K.; Tikoo, K.; Singh, I. P. J. Funct. Foods 2015, 16, 183-193. https://doi.org/10.1016/j.jff.2015.04.013
  22. Watson, C. Y.; Whish, W. J. D.; Threadgill, M. D. Bioorg. Med. Chem. 1998, 6, 721-734. https://doi.org/10.1016/S0968-0896(98)00029-7
  23. Akihisa, T.; Tochizawa, S.; Takahashi, N.; Yamamoto, A.; Zhang, J.; Kikuchi, T.; Fukatsu, M.; Tokuda, H.; Suzuki, N. Chem. Biodivers. 2012, 9, 1172-1187. https://doi.org/10.1002/cbdv.201100349

Cited by

  1. Procyanidin C1 Activates the Nrf2/HO-1 Signaling Pathway to Prevent Glutamate-Induced Apoptotic HT22 Cell Death vol.20, pp.1, 2019, https://doi.org/10.3390/ijms20010142
  2. Preparation of Herbal Formulation for Inflammatory Bowel Disease Based on In Vitro Screening and In Vivo Evaluation in a Mouse Model of Experimental Colitis vol.24, pp.3, 2019, https://doi.org/10.3390/molecules24030464
  3. Two New Phenolic Derivatives withα-Glucosidase Inhibitory Activities fromNoni Juice vol.41, pp.7, 2017, https://doi.org/10.6023/cjoc202101006