Desulfohaplosamate, a new phosphate-containing steroid from Dasychalina sp., is a selective cannabinoid CB2 receptor ligand

Steroids

Volumn 76, Issue 10-11, 2011, Pages 998-1002

  Chianese, Giuseppina ^a   Fattorusso, Ernesto ^a   Taglialatela Scafati, Orazio ^a   Bavestrello, Giorgio ^b   Calcinai, Barbara ^b   Dien, Henny A ^c   Ligresti, Alessia ^d   Di Marzo, Vincenzo ^d  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^c SAM RATULANGI UNIVERSITY   (Indonesia)

^d CNR   (Italy)

Author keywords

Cannabinoid receptors; CB 2 agonist; Haplosamate; Phosphated steroids; Sponges

Indexed keywords

CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; DESULFOHAPLOSAMATE; HAPLOSAMATE A; LIGAND; UNCLASSIFIED DRUG;

ARTICLE; CELL NUCLEUS; DASYCHALINA; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY; RECEPTOR BINDING; SPONGE (PORIFERA);

ANIMALS; MOLECULAR STRUCTURE; PHOSPHATES; PORIFERA; RECEPTOR, CANNABINOID, CB2; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960444138     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.03.013     Document Type: Article

References (23)

1. W.A. Devane, F.A. Dysarz III, M.R. Johnson, L.S. Melvin, and A.C. Howlett Determination and characterization of a cannabinoid receptor in rat brain Mol Pharmacol 34 1988 605 613 (Pubitemid 19007296)
2. M. Herkenham, A.B. Lynn, M.D. Little, M.R. Johnson, L.S. Melvin, and B.R. de Costa Cannabinoid receptor localization in brain Proc Natl Acad Sci USA 87 1990 1932 1936
3. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, and G. Griffin Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258 1992 1946 1949 (Pubitemid 23026736)
4. L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, and T.I. Bonner Structure of a cannabinoid receptor and functional expression of the cloned cDNA Nature 346 1990 561 564
5. S. Munro, K.L. Thomas, and M. Abu-Shaar Molecular characterization of a peripheral receptor for cannabinoids Nature 365 1993 61 65 (Pubitemid 23305569)
6. 2 receptors Proc Natl Acad Sci USA 96 1999 14136 14141
7. 1 receptor Addict Biol 13 2008 188 195 (Pubitemid 351698888)
8. S. Galiegue, S. Mary, J. Marchand, D. Dussossoy, D. Carriere, and P. Carayon Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations Eur J Biochem 232 1995 54 61
9. I. Bab, O. Ofek, J. Tam, J. Rehnelt, and A. Zimmer Endocannabinoids and the regulation of bone metabolism J Neuroendocrinol 20 2008 69 74 (Pubitemid 351552679)
10. S. Yang, J. Smotryski, J. Matasi, G. Ho, D. Tulshian, and W.J. Greenlee Structure-activity relationships of 2,4-diphenyl-1H-imidazole analogs as CB2 receptor agonists for the treatment of chronic pain Bioorg Med Chem Lett 21 2011 182 185
11. J. Gertsch, R.G. Pertwee, and V. Di Marzo Phytocannabinoids beyond the Cannabis plant - do they exist? Br J Pharmacol 160 2010 523 529
12. M. Leonti, L. Casu, S. Raduner, F. Cottiglia, C. Floris, and K.-H. Altmann Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin Biochem Pharmacol 79 2010 1815 1826
13. E. Fattorusso, A. Romano, O. Taglialatela-Scafati, M.J. Achmad, G. Bavestrello, and C. Cerrano Xenimanadins A-D, a family of xenicane diterpenoids from the Indonesian soft coral Xenia sp Tetrahedron 64 2008 3141 3146
14. E. Fattorusso, A. Romano, O. Taglialatela-Scafati, M.J. Achmad, G. Bavestrello, and C. Cerrano Lobozoanthamine, a new zoanthamine-type alkaloid from the Indonesian soft coral Lobophytum sp Tetrahedron Lett 49 2008 2189 2192
15. R.F. Angawi, B. Calcinai, C. Cerrano, H.A. Dien, E. Fattorusso, and F. Scala Dehydroconicasterol and aurantoic acid, a chlorinated polyene derivative, from the Indoensian Sponge Theonella swinhoei J Nat Prod 72 2009 2195 2198
16. A. Qureshi, and D.J. Faulkner Haplosamates A and B: new steroidal sulfamate esters from two Haposclerid sponges Tetrahedron 55 1999 8323 8330 (Pubitemid 29292723)
17. M. Fujita, Y. Nakao, S. Matsunaga, M. Seiki, Y. Itoh, and R.W.M. van Soest Isolation and structure elucidation of two phosphorylated sterol sulfates. MT1-MMP inhibitors from a marine sponge Cribrochalina sp.: revision of structures of haplosamates A and B Tetrahedron 57 2001 3885 3890 (Pubitemid 32382201)
18. F. De Riccardis, M. Iorizzi, L. Minale, R. Riccio, and C. Debitus The first occurrence of polyhydroxylated steroids with phosphate conjugation from the starfish Tremaster novaecaledoniae Tetrahedron Lett 33 1992 1097 1100
19. A. Pereira, T.A. Pfeifer, T.A. Grigliatti, and R.J. Andersen Functional cell-based screening and saturation transfer double-difference NMR have identified haplosamate A as a cannabinoid receptor agonist ACS Chem Biol 4 2009 139 144
20. M. Mayer, and B. Meyer Characterization of ligand binding by saturation transfer difference NMR spectroscopy Angew Chem Int Ed 38 1999 1784 1788 (Pubitemid 29290947)
21. O. Taglialatela-Scafati, A. Pagani, F. Scala, L. De Petrocellis, V. Di Marzo, and G. Grassi Cannabimovone, a cannabinoid with a rearranged terpenoid skeleton from hemp Eur J Org Chem 2010 2067 2072
22. G. Appendino, A. Ligresti, A. Minassi, M.G. Cascio, M. Allar, and O. Taglialatela-Scafati Conformationally constrained fatty acid ethanolamides as cannabinoid and vanilloid receptor probes J Med Chem 52 2009 3001 3009
23. K.D. Patel, J.S. Davison, K.J. Pittman, and K.A. Sharkey Cannabinoid CB(2) receptors in health and disease Curr Med Chem 17 2010 1393 1410