Terpioside B, a difucosyl GSL from the marine sponge Terpios sp. is a potent inhibitor of NO release

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 14, 2010, Pages 5310-5315

  Costantino, Valeria ^a   Fattorusso, Ernesto ^a   Mangoni, Alfonso ^a   Teta, Roberta ^a   Panza, Elisabetta ^a,b   Ianaro, Angela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

Fucose; Glycosphingolipid; NO release; Sponge; Structure elucidation

Indexed keywords

FUCOSE; GLYCOLIPID; MONOGLUCOSYLCERAMIDE; NATURAL PRODUCT; NITRIC OXIDE; PENTASACCHARIDE; TERPIOSIDE A; TERPIOSIDE B; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; DEGRADATION; DRUG POTENCY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY; TERPIOS;

ANIMALS; CELL LINE; GLYCOLIPIDS; LIPOPOLYSACCHARIDES; MACROPHAGE ACTIVATION; MACROPHAGES; MOLECULAR CONFORMATION; NITRIC OXIDE; PORIFERA;

TERPIOS;

EID: 77955327462     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.048     Document Type: Article

References (23)

1. Part 21: V. Costantino, E. Fattorusso, C. Imperatore, A. Mangoni, and R. Teta Eur. J. Org. Chem. 2009 2112
2. E. Miyoshi, K. Moriwaki, and T. Nakagawa J. Biochem. 143 2008 725
3. M. Sugita, C. Hayata, T. Yoshida, M. Suzuki, A. Suzuki, T. Takeda, T. Hori, and F. Nakatani Biochim. Biophys. Acta 1215 1994 163
4. X. Xu, Y. Horibata, M. Inagaki, Y. Hama, K. Sakaguchi, H.M. Goda, N. Okino, and M. Ito Glycobiology 19 2009 1446
5. N. Borbone, S. De Marino, M. Iorizzi, F. Zollo, C. Debitus, A. Ianaro, and B. Pisano Eur. J. Org. Chem. 2001 4651
6. N. Hada, T. Nakashima, S.P. Shrestha, R. Masui, Y. Narukawa, K. Tani, and T. Takeda Bioorg. Med. Chem. Lett. 17 2007 5912
7. T. Miyamoto, A. Yamamoto, M. Wakabayashi, Y. Nagaregawa, M. Inagaki, R. Higuchi, M. Iha, and K. Teruya Eur. J. Org. Chem. 2000 2295
8. F. Cafieri, E. Fattorusso, A. Mangoni, and O. Taglialatela-Scafati Gazz. Chim. Ital. 126 1996 711
9. V. Costantino, E. Fattorusso, C. Imperatore, A. Mangoni, and R. Teta Eur. J. Org. Chem. 2008 2130
10. M.J. Thrippleton, and J. Keeler Angew. Chem., Int. Ed. 42 2003 3938
11. V. Costantino, E. Fattorusso, A. Mangoni, M. Di Rosa, A. Ianaro, and P. Maffia Tetrahedron 52 1996 1573
12. S. Moncada, R.M.J. Palmer, and E.A. Higgs Pharmacol. Rev. 43 1991 109
13. Q. Xie, Y. Kashiwabara, and C.J. Nathan Biol. Chem. 269 1994 4705
14. A. Ialenti, A. Ianaro, S. Moncada, and M. Di Rosa Eur. J. Pharmacol. 211 1992 177
15. A. Ianaro, C.A. O'Donnell, M. Di Rosa, and F.Y. Liew Immunology 82 1994 370
16. A. Ianaro, A. Ialenti, L. Sautebin, and M. Di Rosa Naunyn-Schmiedeberg's Arch. Pharmacol. 358 1998 489
17. H.V. Wilson J. Exp. Zool. 5 1907 245
18. X. Fernandez-Busquets, and M.M. Burger Microsc. Res. Tech. 44 1999 204
19. The perbenzoylated α-glycosides of glucose and galactose showed retention times very close to each other under the condition used, so we preferred to analyze the respective β-glycosides, which were less abundant but easier to separate.
20. V. Costantino, E. Fattorusso, C. Imperatore, and A. Mangoni Eur. J. Org. Chem. 2005 368
21. M. Gutiérrez, T.L. Capson, H.M. Guzmán, J. González, E. Ortega-Barría, E. Quiñoá, and R. Riguera J. Nat. Prod. 69 2006 1379
22. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271
23. A. Ianaro, A. Ialenti, P. Maffia, L. Sautebin, L. Rombol, R. Carnuccio, T. Iuvone, F. D'Acquisto, and M. Di Rosa J. Pharmacol. Exp. Ther. 292 2000 156