Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Cytotoxic Polyketides from the Marine Sponge Discodermia calyx

  • Shinde, Pramod B. (College of Pharmacy, Pusan National University) ;
  • Mansoor, Tayyab A. (College of Pharmacy, Pusan National University) ;
  • Luo, Xuan (College of Pharmacy, Pusan National University) ;
  • Hong, Jong-Ki (College of Pharmacy, Kyung Hee University) ;
  • Lee, Chong-O. (Pharmaceutical Screening Center, Korea Research Institute of Chemical Technology) ;
  • Jung, Jee-H. (College of Pharmacy, Pusan National University)
  • Published : 2007.06.20
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Abstract

Bioassay-guided fractionation of the MeOH extract from the sponge Discodermia calyx collected off the coast of Jeju Island, South Korea, led to the isolation of a polyketide, icadamide C (1), along with previously reported theopederin K (3). Structure elucidation was performed by a combination of high resolution mass and 2D-NMR (principally COSY, HMBC, HSQC, and NOESY) spectroscopy. Stereochemistry of compound 1 was determined as 2R*, 3R*, 6R*, 10S*, 11S*, 12R*, 13S*, 15R* and 2'S by NMR data and Marfey analysis. Isolated metabolites displayed potent cytotoxic activity against a small panel of five human solid tumor cell lines with ED50 values of less than 0.1 μg/mL.

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References

  1. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. J. Am. Chem. Soc. 1986, 108, 2780 https://doi.org/10.1021/ja00270a061
  2. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. J. Org. Chem. 1988, 53, 3930 https://doi.org/10.1021/jo00252a009
  3. Matsunaga, S.; Fujiki, H.; Sakata, D.; Fusetani, N. Tetrahedron 1991, 47, 2999 https://doi.org/10.1016/S0040-4020(01)96031-4
  4. Matsunaga, S.; Wakimoto, T.; Fusetani, N. Tetrahedron Lett. 1997, 38, 3763 https://doi.org/10.1016/S0040-4039(97)00748-X
  5. Matsunaga, S.; Wakimoto, T.; Fusetani, N. J. Org. Chem. 1997, 62, 2640 https://doi.org/10.1021/jo961746b
  6. Wakimoto, T.; Matsunaga, S.; Takai, A.; Fusetani, N. Chem. Biol. 2002, 9, 309 https://doi.org/10.1016/S1074-5521(02)00118-7
  7. Nakao, Y.; Takada, K.; Matsunaga, S.; Fusetani, N. Tetrahedron 2001, 57, 3013 https://doi.org/10.1016/S0040-4020(01)00163-6
  8. Luo, X.; Li, F.; Shinde, P. B.; Hong, J.; Lee, C. O.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2006, 69, 1760 https://doi.org/10.1021/np0604026
  9. Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee, C. O.; Cho, H. Y.; Jung, J. H. J. Nat. Prod. 2007, 70, 2 https://doi.org/10.1021/np060206z
  10. Lee, J.; Wang, W.; Hong, J.; Lee, C. O.; Shin, S.; Im, K. S.; Jung, J. H. Chem. Pharm. Bull. 2007, 55, 459 https://doi.org/10.1248/cpb.55.459
  11. Jung, J. H.; Shinde, P. B.; Hong, J.; Liu, Y.; Sim, C. J. Biochem. Syst. Ecol. 2007, 35, 48 https://doi.org/10.1016/j.bse.2006.08.008
  12. Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828 https://doi.org/10.1021/jo00040a021
  13. Tsukamoto, S.; Matsunaga, S.; Fusetani, N.; Toh-e, A. Tetrahedron 1999, 55, 13697
  14. Paul, G. K.; Gunasekera, S. P.; Longely, R. E.; Pomponi, S. A. J. Nat. Prod. 2002, 65, 59 https://doi.org/10.1021/np0103766
  15. Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Pannell, L. K. J. Am. Chem. Soc. 1988, 110, 4850 https://doi.org/10.1021/ja00222a067
  16. Perry, N. B.; Blunt, J. W.; Munro, M. H.; Thompson, A. M. J. Org. Chem. 1990, 55, 223
  17. Simpson, J. S.; Garson, M. J.; Blunt, J. W.; Munro, M. H. G.; Hooper, J. N. A. J. Nat. Prod. 2000, 63, 704 https://doi.org/10.1021/np990431z
  18. West, L. M.; Northcote, P. T.; Hood, K. A.; Miller, J. H.; Page, M. J. J. Nat. Prod. 2000, 63, 707 https://doi.org/10.1021/np9904511
  19. Sakemi, S.; Ichiba, T.; Kohmoto, S.; Saucy, G.; Higa, T. J. Am. Chem. Soc. 1988, 110, 4851 https://doi.org/10.1021/ja00222a068
  20. Matsunaga, S.; Fusetani, N.; Nakao, Y. Tetrahedron 1992, 48, 8369 https://doi.org/10.1016/S0040-4020(01)86585-6
  21. Kobayashi, J.; Itagaki, F.; Shigemori, H.; Sasaki, T. J. Nat. Prod. 1993, 56, 976 https://doi.org/10.1021/np50096a030
  22. Vuong, D.; Capon, R. J.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Nat.Prod. 2001, 64, 640 https://doi.org/10.1021/np000474b
  23. Clardy, J.; He, H. U. S. Patent 1995, 5,476,953
  24. Chen, S. P.; Ahmed, A. F.; Dai, C. F.; Lu, C. K.; Hu, W. P.; Wang, J. J.; Sheu, J. H. Tetrahedron 2006, 62, 6802 https://doi.org/10.1016/j.tet.2006.04.088
  25. Chill, L.; Rudi, A.; Benayahu, Y.; Schleyer, M.; Kashman, Y. Org. Lett. 2004, 6, 755 https://doi.org/10.1021/ol036454t
  26. Jayasuriya, H.; Guan, Z.; Polishook, J. D.; Dombrowski, A. W.; Felock, P. J.; Hazuda, D. J.; Singh, S. B. J. Nat. Prod. 2003, 66, 551 https://doi.org/10.1021/np020533g
  27. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591 https://doi.org/10.1007/BF02908688
  28. Pavan, M.; Bo, G. Physiol. Compar. Oceol. 1953, 3, 307
  29. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31 https://doi.org/10.1055/s-2007-971236

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