Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Epi-Leptosphaerin: A New L-Isoascorbic Acid Derivative from Marine Sponges

  • Kulkarni, Roshan R. (College of Pharmacy, Chungnam National University) ;
  • Jo, A Reum (College of Pharmacy, Chungnam National University) ;
  • Kim, Young Ho (College of Pharmacy, Chungnam National University) ;
  • Na, MinKyun (College of Pharmacy, Chungnam National University)
  • Received : 2015.07.12
  • Accepted : 2015.09.30
  • Published : 2015.12.31
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Abstract

A new L-isoascorbic acid derivative epi-leptosphaerin (1) and two known compounds leptosphaerin (2), and verongamine (3) were isolated from sponges of the orders Verongida and Thorectidae. Compounds 1 and 2 are most likely of sponge-associated fungal origin. In the present study, isolated compounds were investigated for their inhibition of soluble epoxide hydrolase (sEH), which is considered a promising target for the management of pain, inflammation, and comorbidities associated with diabetes. Compound 3, verongamine, displayed weak inhibitory activity against sEH with an $IC_{50}$ value $51.5{\pm}1.0{\mu}M$.

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References

  1. Perdicaris, S.; Vlachogianni, T.; Valavanidis, A. Nat. Prod. Chem. Res. 2013, 1, 114.
  2. Simmons, T. L.; Coates, R. C.; Clark, B. R.; Engene, N.; Gonzalez, D.; Esquenazi, E.; Dorrestein, P. C.; Gerwick, W. H. Proc. Natl. Acad. Sci. 2008, 105, 4587-4594. https://doi.org/10.1073/pnas.0709851105
  3. Abdelmohsen, U. R.; Bayer, K.; Hentschel, U. Nat. Prod. Rep. 2014, 31, 381-399. https://doi.org/10.1039/c3np70111e
  4. Suryanarayanan, T. S. Bot. Mar. 2012, 55, 553-564.
  5. Lemmens-Gruber, R.; Kamyar, M. R.; Dornetshuber, R. Curr. Med. Chem. 2009, 16, 1122-1137. https://doi.org/10.2174/092986709787581761
  6. Imig, J. D.; Hammock, B. D. Nat. Rev. Drug Discov. 2009, 8, 794-805. https://doi.org/10.1038/nrd2875
  7. Hammock, B. D.; Wagner, K.; Inceoglu, B. Pain Manag. 2011, 1, 383-386. https://doi.org/10.2217/pmt.11.47
  8. Kochanowska, A. J.; Rao, K. V.; Childress, S.; El-Alfy, A.; Matsumoto, R. R.; Kelly, M.; Stewart, G. S.; Sufka, K. J.; Hamann, M. T. J. Nat. Prod. 2008, 71, 186-189. https://doi.org/10.1021/np070371u
  9. Hwang, I. H.; Oh, J.; Kochanowska-Karamyan, A.; Doerksen, R. J.; Na, M.; Hamann, M. T. Tetrahedron Lett. 2013, 54, 3872-3876. https://doi.org/10.1016/j.tetlet.2013.05.032
  10. Kulkarni, R.; Kim, J. H.; Kim, Y. H.; Oh, S.; Na, M. Nat. Prod. Sci. 2015, 21, 25-29.
  11. Hwang, I. H.; Oh, J.; Zhou, W.; Park, S.; Kim, J.-H.; Chittiboyina, A. G.; Ferreira, D.; Song, G. Y.; Oh, S.; Na, M., et al. J. Nat. Prod. 2015, 78, 453-461. https://doi.org/10.1021/np500843m
  12. White, J. D.; Badger, R. A.; Kezar III, H. S.; Pallenberg, A. J.; Schiehser, G. A. Tetrahedron 1989, 45, 6631-6644. https://doi.org/10.1016/S0040-4020(01)89133-X
  13. Miroslav, P.; Emmanuel, Z.; Fletcher Jr., H. G. Carbohydr. Res. 1975, 43, 345-354. https://doi.org/10.1016/S0008-6215(00)83498-9
  14. Hanisak, M. D.; Samuel, M. A. Dev. Hydrobiol. 1987, 41, 399-404.
  15. Takahashi, C.; Numata, A.; Ito, Y.; Matsumura, E.; Araki, H.; Iwaki, H.; Kushida, K. J. Chem. Soc. Perkin Trans. 1994, 1, 1859-1864.
  16. Kyotani, D.; Hasegawa, K.; Ohishi, H.; Wu, W.; Wang, L.; Hasumi, K. Biosci. Biotechnol. Biochem. 2009, 73, 954-956. https://doi.org/10.1271/bbb.80785
  17. Mierzwa, R.; King, A.; Conover, M. A.; Tozzi, S.; Puar, M. S.; Patel, M.; Coval, S. J.; Pomponi, S. A. J. Nat. Prod. 1994, 57, 175-177. https://doi.org/10.1021/np50103a029

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