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MeSH Review

Agelas

 
 
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Disease relevance of Agelas

  • As the result of a structurally guided isolation to identify lead compounds for the treatment of opportunistic infections of AIDS, the dihydrochloride salt of a new symmetrical pyrrole dimer debromosceptrin (1), and two known pyrrole analogues (2 and 3) were isolated from the Caribbean sponge Agelas coniferacollected from Belize [1].
 

High impact information on Agelas

  • Total Synthesis of Ageladine A, an Angiogenesis Inhibitor from the Marine Sponge Agelas nakamurai [2].
  • Reinvestigation of the glycosphingolipid composition of the marine sponge Agelas clathrodes revealed the presence of a new tetraglycosylated alpha-galactoglycosphingolipid (1a), containing an unusual l-rhamnose unit in the sugar head [3].
  • [reaction: see text] The first enantioselective syntheses of slagenins B and C, marine metabolites from Agelas nakamurai, starting from L-arabinose have been described [4].
  • AGL-517 (AGL) has an alpha-galactosylceramide structure and is a derivative of agelasphin-9b, which in turn is isolated from Agelas mauritianus and has immunomodulating activity [5].
  • The mechanism of action of sceptrin, an antimicrobial agent isolated from the sponge Agelas mauritiana, was investigated [6].
 

Biological context of Agelas

 

Associations of Agelas with chemical compounds

  • 26-Nor-25-isopropyl-ergosta-5,7,22E-trien-3beta-ol: a new C(29) sterol from the sponge Agelas sceptrum from Jamaica [8].
  • From a Maltese sample of the marine sponge Agelas oroides, five compounds: oroidin (1), 2-cyano-4,5-dibromopyrrole (2), 4,5-dibromopyrrole-2-carboxylic acid (3), 4,5-dibromopyrrole-2-carboxylic acid methyl ester (4), and 4 alpha-methyl-5 alpha-cholest-8-en-3 beta-ol (5) have been isolated [9].
  • Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation [7].
  • As a putative key intermediate, the natural product Nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine (1) from the sponge Agelas wiedenmayeri was synthesized in the solid phase starting from Fmoc/Pmc-protected L-homoarginine and in solution starting from readily available L-lysine methyl ester [10].
  • Agelasines H and I, 9-methyladenine-containing diterpenoids from an Agelas sponge [11].
 

Gene context of Agelas

  • Glycolipids from sponges. Part 17. Clathrosides and isoclathrosides, unique glycolipids from the Caribbean sponge Agelas clathrodes [12].
  • A potent actomyosin ATPase activator from the Okinawan marine sponge Agelas cf. nemoechinata [13].

References

  1. Debromosceptrin, an alkaloid from the Caribbean sponge Agelas conifera. Shen, X., Perry, T.L., Dunbar, C.D., Kelly-Borges, M., Hamann, M.T. J. Nat. Prod. (1998) [Pubmed]
  2. Total Synthesis of Ageladine A, an Angiogenesis Inhibitor from the Marine Sponge Agelas nakamurai. Meketa, M.L., Weinreb, S.M. Org. Lett. (2006) [Pubmed]
  3. Glycolipids from sponges. 13. Clarhamnoside, the first rhamnosylated alpha-galactosylceramide from Agelas clathrodes. Improving spectral strategies for glycoconjugate structure determination. Costantino, V., Fattorusso, E., Imperatore, C., Mangoni, A. J. Org. Chem. (2004) [Pubmed]
  4. Carbohydrate-based synthesis of naturally occurring marine metabolites slagenins B and C. Gurjar, M.K., Bera, S. Org. Lett. (2002) [Pubmed]
  5. alpha-Galactosylceramide (AGL-517) treatment protects mice from lethal irradiation. Inoue, H., Koezuka, Y., Nishi, N., Osawa, M., Motoki, K., Kobayashi, E., Kabaya, K., Obuchi, M., Fukushima, H., Mori, K.J. Exp. Hematol. (1997) [Pubmed]
  6. A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana. Bernan, V.S., Roll, D.M., Ireland, C.M., Greenstein, M., Maiese, W.M., Steinberg, D.A. J. Antimicrob. Chemother. (1993) [Pubmed]
  7. Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation. Bickmeyer, U., Drechsler, C., Köck, M., Assmann, M. Toxicon (2004) [Pubmed]
  8. 26-Nor-25-isopropyl-ergosta-5,7,22E-trien-3beta-ol: a new C(29) sterol from the sponge Agelas sceptrum from Jamaica. Hu, J.F., Kelly, M., Hamann, M.T. Steroids (2002) [Pubmed]
  9. Antiplasmodial and cytotoxic metabolites from the Maltese sponge Agelas oroides. König, G.M., Wright, A.D., Linden, A. Planta Med. (1998) [Pubmed]
  10. Synthesis of the marine natural product nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine, a putative biogenetic precursor of the pyrrole-imidazole alkaloids. Lindel, T., Hochgürtel, M., Assmann, M., Köck, M. J. Nat. Prod. (2000) [Pubmed]
  11. Agelasines H and I, 9-methyladenine-containing diterpenoids from an Agelas sponge. Fu, X., Schmitz, F.J., Tanner, R.S., Kelly-Borges, M. J. Nat. Prod. (1998) [Pubmed]
  12. Glycolipids from sponges. Part 17. Clathrosides and isoclathrosides, unique glycolipids from the Caribbean sponge Agelas clathrodes. Costantino, V., Fattorusso, E., Imperatore, C., Mangoni, A. J. Nat. Prod. (2006) [Pubmed]
  13. A potent actomyosin ATPase activator from the Okinawan marine sponge Agelas cf. nemoechinata. Kobayashi, J., Tsuda, M., Ohizumi, Y. Experientia (1991) [Pubmed]
 
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