Hanishin, a Semiracemic, Bioactive C9 Alkaloid of the Axinellid Sponge Acanthella carteri from the Hanish Islands. A Shunt Metabolite?

Author:

Mancini Ines,Guella Graziano,Amade Philippe,Roussakis Christos,Pietra Francesco

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference17 articles.

1. D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. J. Chem. Soc., Chem. Commun. 1993, 1305–1306; D'Ambrosio, M.; Guerriero, A.; Ripamonti, M.; Debitus, C.; Waikedre, J.; Pietra, F. Helv. Chim. Acta 1996, 79, 727–735.

2. Hanishenols A-B, novel linear or methyl-branched glycerol enol ethers of the axinellid sponge Acanthella carteri (= Acanthella aurantiaca) from the Hanish Islands, southern Red Sea

3. Fractions 20–22 of previous chromatographic (FC) work up of the ethanolic extracts of the sponge[2]were subjected to reversed-phase RP-18 HPLC with H2O-MeCN 2:3, solvent flow 5 ml min−1 under UV monitoring at λ 254 nm, to give 4 (tR 4.0 min, 3.0 mg, 0.022% on raw extract), 3 (tR 5.5 min, 1.2 mg, 0.009%) and 2 (tR 12.0 min, 2.5 mg, 0.087%). Amine-HPLC (EtOAc-MeOH 8:2 with added Et3N 5%, γ 280 nm) of fraction 25 from the above FC gave oroidin 1 (tR 6.5 min, 4.3 mg, 0.031%).

4. Garcia, E.E.; Benjamin, L.E.; Fryer, I.R. J. Chem. Soc., Chem. Commun, 1973, 78–79.

5. a) Tada, H.; Tozko, T. Chem. Lett. 1988, 803–806; b) Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. J. Nat. Prod. 1996, 59, 501–503.

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