Bulletin of the Korean Chemical Society

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A Novel Cytotoxic Alkaloid of Lamellarin Class from a Marine Ascidian Didemnum sp.

  • Ham, Jung-Yeob (Marine Biotechnology Laboratory and Research Institute of Oceanography, School of Earth and Environmental Sciences, Seoul National University) ;
  • Kang, Heon-Joong (Marine Biotechnology Laboratory and Research Institute of Oceanography, School of Earth and Environmental Sciences, Seoul National University)
  • Published : 2002.01.20
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Abstract

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References

  1. Davidson, B. S. Chem. Rev. 1994, 93, 1771 https://doi.org/10.1021/cr00021a006
  2. Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1 https://doi.org/10.1039/b006897g
  3. Anderson, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492 https://doi.org/10.1021/ja00305a027
  4. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, D. J. Org. Chem. 1988, 53, 4570 https://doi.org/10.1021/jo00254a029
  5. Davis, R. A.; Carroll, A. R.; Pirens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419 https://doi.org/10.1021/np9803530
  6. Urban, S.; Butler, M. S.; Capon, R. J. Aust. J. Chem. 1994, 47, 1919 https://doi.org/10.1071/CH9941919
  7. Urban, S.; Hobbs, L.; Hopper, J. N. A.; Capon, R. J. Aust. J. Chem. 1995, 48, 1491 https://doi.org/10.1071/CH9951491
  8. Carroll, A. R.; Bowden, B. F.; Coll, J. C. Aust. J. Chem. 1993, 46, 489 https://doi.org/10.1071/CH9930489
  9. Urban, S.; Capon, R. J. Aust. J. Chem. 1996, 49, 711
  10. Reddy, M. V. R.; Faulkner, D. J.; Venkateswarlu, Y.; Rao, M. R. Tetrahedron 1997, 53, 3457 https://doi.org/10.1016/S0040-4020(97)00073-2
  11. Reddy, M. V. R.; Rao, M. R.; Rhodes, D.; Hansen, M. S. T.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901 https://doi.org/10.1021/jm9806650
  12. Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254 https://doi.org/10.1021/jo962132+
  13. Quesada, A. R.; Gravalos, M. D. G.; Puentes, J. L. F. Br. J. Cancer 1996, 74, 677 https://doi.org/10.1038/bjc.1996.421
  14. Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54 https://doi.org/10.1021/ja982078+
  15. Piantini, U.; Sorensen, W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 104, 6800 https://doi.org/10.1021/ja00388a062
  16. Doddrell, D. M.; Pegg, D. T.; Bendall, M. R. J. Magn. Reson. 1982, 48, 323
  17. Bax, A.; Drobny, G. J. Magn. Reson. 1985, 61, 306
  18. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093 https://doi.org/10.1021/ja00268a061
  19. Mosmann, T. J. Immunol. Methods 1983, 65, 55 https://doi.org/10.1016/0022-1759(83)90303-4
  20. Jackman, L. M.; Sternhill, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon Press: Oxford, U. K., 1969; p 61

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