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Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp. ArchiMer
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-kondracki, Marie-lise.
Indole derivatives including bromoindoles have been isolated from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Their structures were established through analysis of mass spectra and 1D and 2D NMR spectroscopic data. Their potential inhibitory phospholipase A(2) (PLA(2)), antioxidant and cytotoxic activities were evaluated. The new derivative 5,6-dibromo-L-hypaphorine (9) isolated from Hyrtios sp. revealed a weak bee venom PLA2 inhibition (IC50 0.2 mM) and a significant antioxidant activity with an Oxygen Radical Absorbance Capacity (ORAC) value of 0.22. The sesquiterpene aureol (4), also isolated from Hyrtios sp., showed the most potent antioxidant activity with an ORAC value of 0.29.
Tipo: Text Palavras-chave: Indole derivatives; Bromoindoles; Marine sponge; Rhopaloeides odorabile; Hyrtios sp.; PLA(2) inhibitor; Antioxidant; Cytotoxic.
Ano: 2011 URL: https://archimer.ifremer.fr/doc/00214/32485/30975.pdf
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New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata ArchiMer
Campos, Pierre-eric; Pichon, Emmanuel; Moriou, Céline; Clerc, Patricia; Trépos, Rozenn; Frederich, Michel; De Voogd, Nicole; Hellio, Claire; Gauvin-bialecki, Anne; Al-mourabit, Ali.
Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum...
Tipo: Text Palavras-chave: Fascaplysinopsis reticulata; Marine sponge; Tryptamine alkaloids; Antimalarial activity; Antimicrobial activity.
Ano: 2019 URL: https://archimer.ifremer.fr/doc/00485/59664/62722.pdf
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Oxygenated Polyketides from Plakinastrella mamillaris as a New Chemotype of PXR Agonists ArchiMer
Festa, Carmen; D'Amore, Claudio; Renga, Barbara; Lauro, Gianluigi; De Marino, Simona; D'Auria, Maria Valeria; Bifulco, Giuseppe; Zampella, Angela; Fiorucci, Stefano.
Further purification of the apolar extracts of the sponge Plakinastrella mamillaris, afforded a new oxygenated polyketide named gracilioether K, together with the previously isolated gracilioethers E-G and gracilioethers I and J. The structure of the new compound has been elucidated by extensive NMR (H-1 and C-13, COSY, HSQC, HMBC, and ROESY) and ESI-MS analysis. With the exception of gracilioether F, all compounds are endowed with potent pregnane-X-receptor (PXR) agonistic activity and therefore represent a new chemotype of potential anti-inflammatory leads. Docking calculations suggested theoretical binding modes of the identified compounds, compatible with an agonistic activity on hPXR, and clarified the molecular basis of their biological activities.
Tipo: Text Palavras-chave: Marine sponge; Plakinastrella mamillaris; Oxygenated polyketide; Nuclear receptors; Pregnane-X-receptor; Anti-inflammatory activity.
Ano: 2013 URL: https://archimer.ifremer.fr/doc/00217/32781/31238.pdf
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