Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Graphiumins I and J, New Thiodiketopiperazines from the Marine-derived Fungus Graphium sp. OPMF00224

  • Received : 2015.06.30
  • Accepted : 2015.08.03
  • Published : 2015.12.31
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Abstract

Two new thiodiketopiperazines (TDKPs), designated graphiumins I (1) and J (2), were isolated from the culture broth of the marine-derived fungus Graphium sp. OPMF00224 by solvent extraction, silica gel column chromatography, and HPLC. Their absolute structures were elucidated by spectroscopic analyses (1D and 2D NMR data, ROESY correlations, and CD data) and chemical methods. They were found to be structurally rare TDKPs with a phenylalanine-derived indolin substructure. Compounds 1 and 2 inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus (MRSA) with $IC_{50}$ values of 63.5 and $76.5{\mu}g/ml$, respectively, without inhibiting its growth, even at $250{\mu}g/ml$.

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References

  1. Centers for Disease Control and Prevention (CDC). MMWR Morb. Mortal. Wkly. Rep. 1997, 46, 765-766.
  2. Hiramatsu, K.; Hanaki, H.; Ino, T.; Yabuta, K.; Oguri, T.; Tenover, F. C. J. Antimicrob. Chemother. 1997, 40, 135-136. https://doi.org/10.1093/jac/40.1.135
  3. Marshall, J. H.; Wilmoth, G. J. J. Bacteriol. 1981, 147, 900-913.
  4. Marshall, J. H.; Wilmoth, G. J. J. Bacteriol. 1981, 147, 914-919.
  5. Clauditz, A.; Resch, A.; Wieland, K. P.; Peschel, A.; Gotz, F. Infect. Immun. 2006, 74, 4950-4953. https://doi.org/10.1128/IAI.00204-06
  6. Liu, G. Y.; Essex, A.; Buchanan, J. T.; Datta, V.; Hoffman, H. M.; Bastian, J. F.; Fierer, J.; Nizet, V. J. Exp. Med. 2005, 202, 209-215. https://doi.org/10.1084/jem.20050846
  7. Liu, C. I.; Liu, G. Y.; Song, Y.; Yin, F.; Hensler, M. E.; Jeng, W. Y.; Nizet, V.; Wang, A. H.; Oldfield, E. Science 2008, 319, 1391-1394. https://doi.org/10.1126/science.1153018
  8. Song, Y.; Liu, C. I.; Lin, F. Y.; No, J. H.; Hensler, M. E.; Liu, Y. L.; Jeng, W. Y.; Low, J.; Liu, G. Y.; Nizet, V.; Wang, A. H.; Oldfield, E. J. Med. Chem. 2009, 52, 3869-3880. https://doi.org/10.1021/jm9001764
  9. Liu, C. I.; Jeng, W. Y.; Chang, W. J.; Ko, T. P.; Wang, A. H. J. Biol. Chem. 2012, 287, 18750-18757. https://doi.org/10.1074/jbc.M112.351254
  10. Lee, J. H.; Cho, H. S.; Kim, Y.; Kim, J. A.; Banskota, S.; Cho, M. H.; Lee, J. Appl. Microbiol. Biotechnol. 2013, 97, 4543-4552. https://doi.org/10.1007/s00253-012-4674-z
  11. Lee, J. H.; Park, J. H.; Cho, M. H.; Lee, J. Curr. Microbiol. 2012, 65, 726-732. https://doi.org/10.1007/s00284-012-0229-x
  12. Sakai, K.; Koyama, N.; Fukuda, T.; Mori, Y.; Onaka, H.; Tomoda, H. Biol. Pharm. Bull. 2012, 35, 48-53. https://doi.org/10.1248/bpb.35.48
  13. Fukuda, T.; Nagai, K.; Tomoda, H. J. Nat. Prod. 2012, 75, 2228-2231. https://doi.org/10.1021/np300428r
  14. Fukuda, T.; Shimoyama, K.; Nagamitsu, T.; Tomoda, H. J. Antibiot. 2014, 67, 445-450. https://doi.org/10.1038/ja.2014.14
  15. Fukuda, T.; Shinkai, M.; Sasaki, E.; Nagai, K.; Kurihara, Y.; Kanamoto, A.; Tomoda, H. J. Antibiot. 2015, doi: 10.1038/ja.2015.41.
  16. Wang, J. M.; Jiang, N.; Ma, J.; Yu, S. S.; Tan, R. X.; Dai, J. G.; Si, Y. K.; Ding, G. Z.; Ma, S. G.; Qu, J.; Fang, L.; Du, D. Tetrahedron 2013, 69, 1195-1201. https://doi.org/10.1016/j.tet.2012.11.047
  17. Nagai, K.; Doi, T.; Sekiguchi, T.; Namatame, I.; Sunazuka, T.; Tomoda, H.; Omura, S.; Takahashi, T. J. Comb. Chem. 2006, 8, 103-109. https://doi.org/10.1021/cc050084d
  18. Hegde, V. R.; Dai, P.; Patel, M.; Das, P. R.; Puar, M. S. Tetrahedron Lett. 1997, 38, 911-914. https://doi.org/10.1016/S0040-4039(96)02457-4
  19. Neuss, N.; Nagarajan, R.; Molloy, B. B.; Huckstep. L. L. Tetrahedron Lett. 1968, 9, 4467-4471. https://doi.org/10.1016/S0040-4039(01)99162-2
  20. Guo, C. J.; Yeh, H. H.; Chiang, Y. M.; Sanchez, J. F.; Chang, S. L.; Bruno, K. S.; Wang, C. C. J. Am. Chem. Soc. 2013, 135, 7205-7213. https://doi.org/10.1021/ja3123653

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