Agelasine

Agelasines are 7,9-dialkylpurinium salts isolated from marine sponges (Agelas sp.). They are considered secondary metabolites. Their contribution to the sponge is assumed to be some sort of protection against microorganisms. At the present time a total of eleven 9-methyladeninium salts, agelasine A–I, epiagelasine C and agelin B, are known.[1][2][3][4][5][6][7] All compounds carry a diterpenoid side chain in the adenine 7-position. The agelasines are closely related in structure with the agelasimines.

Chemists have reproduced (–)-agelasine A,[8] (–)-agelasine B,[9] (−)-agelasine E,[10] (−)-agelasine F,[11] and (+)-agelasine D[12] by organic synthesis.

Agelasines are associated with bioactivities such as antimicrobial and cytotoxic effects, as well as contractive responses of smooth muscles and inhibition of Na/K-ATPase (NaKATPase). Furthermore, in vitro activity against Mycobacterium tuberculosis is reported for agelasine F.[13]

References
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  3. R. J. Capon and D. J. Faulkner, J. Am. Chem. Soc., 1984, 106, 1819
  4. H. Wu, H. Nakamura, J. Kobayashi, M. Kobayashi, Y. Ohizumi and Y. Hirata, Bull. Chem. Soc. Jpn., 1986, 59, 2495
  5. K. Ishida, M. Ishibashi, H. Shigemori, T. Sasaki and J. Kobayashi, Chem. Pharm. Bull., 1992, 40, 766
  6. T. Hattori, K. Adachi and Y. Shizuri, J. Nat. Prod., 1997, 60, 411
  7. X. Fu, F. J. Schmitz, R. S. Tanner and M. Kelly-Borges, J. Nat. Prod., 1998, 61, 548
  8. E. Piers, M. L. Livain, Y. Han, G. L. Plourde, L. Guy and W.-L. Yeh, J. Chem. Soc., Perkin Trans. 1, 1995, 963
  9. E. Piers and J. Y. Roberge, Tetrahedron Lett., 1992, 33, 6923; (b) H. Iio, K. Asao and T. Tokoroyama, J. Chem. Soc., Chem. Commun., 1985, 774
  10. A. K. Bakkestuen, L.-L. Gundersen, D. Petersen, B. Utenova and A. Vik, Org. Biomol. Chem., 2005, 3, 1025
  11. K. Asao, H. Iio and T. Tokoroyama, Tetrahedron Lett., 1989, 30, 6401
  12. B. T. Utenova and L.-L. Gundersen, Tetrahedron Lett., 2004, 45, 4233
  13. G. C. Mangalindan, M. T. Talaue, L. J. Cruz, S. G. Franzblau, L. B. Adams, A. D. Richardson, C. M. Ireland and G. P. Conception, Planta Med., 2000, 66, 364
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