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Two New Scalaranes from a Korean Marine Sponge Spongia sp.

  • Yang, Inho (School of Earth and Environmental Sciences, Seoul National University) ;
  • Nam, Sang-Jip (Department of Chemistry and Nano Science, Global Top5 Program, Ewha Womans University) ;
  • Kang, Heonjoong (School of Earth and Environmental Sciences, Seoul National University)
  • Received : 2015.06.30
  • Accepted : 2015.08.17
  • Published : 2015.12.31

Abstract

Intensive chemical investigation of Korean marine sponge Spongia sp. has led to the isolation of two new scalaranes. The planar structures of the new compounds 1 and 2 were determined through 1D and 2D NMR spectral data analysis, while the relative stereochemistry of the compounds was determined based on the analysis of $^1H-^1H$ coupling constants and NOESY spectroscopic data. Compounds 1 and 2 did not display any significant biological activities on farnesoid X-activated receptor (FXR) in co-transfection assay.

Keywords

References

  1. Fattorusso, E.; Gerwick, W. H.; Taglialatela-Scafati, O. Handbook of Marine Natural Products; Springer: New York, 2012, p4.
  2. Wang, L.; Yang, B.; Lin, X. P.; Zhou, X. F.; Liu, Y. Nat. Prod. Rep. 2013, 30, 455-473. https://doi.org/10.1039/c3np20089b
  3. Gonzalez, M. A. Curr. Bioact. Compd. 2010, 6, 178-206. https://doi.org/10.2174/157340710793237362
  4. Fattorusso, E.; Magno, S.; Santacroce, C.; Sica, D. Tetrahedron 1972, 28, 5993-5997. https://doi.org/10.1016/0040-4020(72)88132-8
  5. Harinantenaina, L.; Brodie, P. J.; Maharavo, J.; Bakary, G.; TenDyke, K.; Shen, Y.; Kingston, D. G. Bioorg. Med. Chem. 2013, 21, 2912-2917 https://doi.org/10.1016/j.bmc.2013.03.078
  6. Hassan, M. H. A.; Rateb, M. E.; Hetta, M.; Abdelaziz, T. A.; Sleim, M. A.; Jaspars, M.; Mohammed, R. Tetrahedron 2015, 71, 577-583 https://doi.org/10.1016/j.tet.2014.12.035
  7. Yong, K. W.; Mudianta, I. W.; Cheney, K. L.; Mollo, E.; Blanchfield, J. T.; Garson, M. J. J. Nat. Prod. 2015, 78, 421-430. https://doi.org/10.1021/np500797b
  8. Cimino, G.; De Rosa, S.; De Stefano, S.; Sodano, G. Comp. Biochem. Phys. B 1982, 73, 471-474 https://doi.org/10.1016/0305-0491(82)90061-X
  9. Rogers, S. D.; Paul, V. J. Mar. Ecol. Prog. Ser. 1991, 77, 221-232 https://doi.org/10.3354/meps077221
  10. Avila, C.; Paul, V. J. Mar. Ecol. Prog. Ser. 1997, 150, 171-180 https://doi.org/10.3354/meps150171
  11. Walker, R. P.; Thompson, J. E.; Faulkner, D. J. J. Org. Chem. 1980, 45, 4976-4979 https://doi.org/10.1021/jo01312a032
  12. Thompson, J. E.; Walker, R. P.; Faulkner, D. J. Mar. Biol. 1985, 88, 11-21. https://doi.org/10.1007/BF00393038
  13. Sera, Y.; Adachi, K.; Shizuri, Y. J. Nat. Prod. 1999, 62, 152-154. https://doi.org/10.1021/np980263v
  14. Diyabalanage, T.; Ratnayake, R.; Bokesch, H. R.; Ransom, T. T.; Henrich, C. J.; Beutler, J. A.; McMahon, J. B.; Gustafson, K. R. J. Nat. Prod. 2012, 75, 1490-1494
  15. Cao, F.; Wu, Z. H.; Shao, C. L.; Pang, S.; Liang, X. Y.; de Voogd, N. J.; Wang, C. Y. Org. Biomol. Chem. 2015, 13, 4016-4024. https://doi.org/10.1039/C4OB02532F
  16. Chang, Y. C.; Tseng, S. W.; Liu, L. L.; Chou, Y.; Ho, Y. S.; Lu, M. C.; Su, J. H. Mar. Drugs 2012, 10, 987-997. https://doi.org/10.3390/md10050987
  17. Mo, S.; Krunic, A.; Pegan, S. D.; Franzblau, S. G.; Orjala, J. J. Nat. Prod. 2009, 72, 2043-2045. https://doi.org/10.1021/np900288x
  18. Marshall, L. A.; Winkler, J. D.; Griswold, D. E.; Bolognese, B.; Roshak, A.; Sung, C. M.; Webb, E. F.; Jacobs, R. J. Pharmacol. Exp. Ther. 1994, 268, 709-717.
  19. Festa, C.; Cassiano, C.; D'Auria, M. V.; Debitus, C.; Monti, M. C.; De Marino, S. Org. Biomol. Chem. 2014, 12, 8646-8655. https://doi.org/10.1039/C4OB01510J
  20. Abdjul, D. B.; Yamazaki, H.; Takahashi, O.; Kirikoshi, R.; Mangindaan, R. E.; Namikoshi, M. Bioorg. Med. Chem. Lett. 2015, 25, 904-907. https://doi.org/10.1016/j.bmcl.2014.12.058
  21. Putra, M. Y.; Bavestrello, G.; Cerrano, C.; Renga, B.; D'Amore, C.; Fiorucci, S.; Fattorusso, E.; Taglialatela-Scafati, O. Steroids 2012, 77, 433-440. https://doi.org/10.1016/j.steroids.2011.12.026
  22. Jeon, J. E.; Bae, J.; Lee, K. J.; Oh, K. B.; Shin, J. J. Nat. Prod. 2011, 74, 847-851 https://doi.org/10.1021/np1006873
  23. Lee, Y. J.; Lee, J. W.; Lee, D. G.; Lee, H. S.; Kang, J. S.; Yun, J. Int. J. Mol. Sci. 2014, 15, 20045-20053. https://doi.org/10.3390/ijms151120045
  24. Nam, S. J.; Ko, H.; Shin, M.; Ham, J.; Chin, J.; Kim, Y.; Kim, H.; Shin, K.; Choi, H.; Kang, H. Bioorg. Med. Chem. Lett. 2006, 16, 5398-5402 https://doi.org/10.1016/j.bmcl.2006.07.079
  25. Nam, S. J.; Ko, H.; Ju, M. K.; Hwang, H.; Chin, J.; Ham, J.; Lee, B.; Lee, J.; Won, D. H.; Choi, H.; Ko, J.; Shin, K.; Oh, T.; Kim, S.; Rho, J. R.; Kang, H. J. Nat. Prod. 2007, 70, 1691-1695 https://doi.org/10.1021/np070024k
  26. Hahn, D.; Won, D. H.; Mun, B.; Kim, H.; Han, C.; Wang, W.; Chun, T.; Park, S.; Yoon, D.; Choi, H.; Nam, S. J.; Ekins, M.; Chin, J.; Kang, H. Bioorg. Med. Chem. Lett. 2013, 23, 2336-2339. https://doi.org/10.1016/j.bmcl.2013.02.061

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