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Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp.

Longeon A, Copp BR, Quévrain E, Roué M, Kientz B, Cresteil T, Petek S, Debitus C, Bourguet-Kondracki ML - Mar Drugs (2011)

Bottom Line: 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.The sesquiterpene aureol (4), also isolated from Hyrtios sp., showed the most potent antioxidant activity with an ORAC value of 0.29.

View Article: PubMed Central - PubMed

Affiliation: Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 MNHN-CNRS, Muséum National d'Histoire Naturelle, 57 Rue Cuvier (C.P. 54), 75005 Paris, France.

ABSTRACT
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 A₂ (PLA₂), 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.

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Structures of compounds 4–9 isolated from the marine sponge Hyrtios sp.
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f2-marinedrugs-09-00879: Structures of compounds 4–9 isolated from the marine sponge Hyrtios sp.

Mentions: Chromatographic fractionation of the CH2Cl2 extract of Hyrtios sp. using silica gel afforded aureol (4), rapidly identified by comparison with literature data [6]. Chromatographic fractionation of the MeOH extract of Hyrtios sp. using C18 and LH 20 columns followed by successive ODS C18 HPLC revealed the presence of five dibromoalkaloids 5–9. The structures of the known compounds 5–8 were rapidly determined as 5,6-dibromotryptamine 5, N-methyl-5,6-dibromotryptamine (6) [7], N,N-dimethyl-5,6-dibromotryptamine (7) [8], and 5,6-dibromoabrine (8) [9] by comparison with literature data. The structure of the new metabolite, 5,6-dibromo-l-hypaphorine (9), was obtained through detailed examination of mass spectrometric data and extensive 1D and 2D NMR studies (Figure 2).


Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp.

Longeon A, Copp BR, Quévrain E, Roué M, Kientz B, Cresteil T, Petek S, Debitus C, Bourguet-Kondracki ML - Mar Drugs (2011)

Structures of compounds 4–9 isolated from the marine sponge Hyrtios sp.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3111189&req=5

f2-marinedrugs-09-00879: Structures of compounds 4–9 isolated from the marine sponge Hyrtios sp.
Mentions: Chromatographic fractionation of the CH2Cl2 extract of Hyrtios sp. using silica gel afforded aureol (4), rapidly identified by comparison with literature data [6]. Chromatographic fractionation of the MeOH extract of Hyrtios sp. using C18 and LH 20 columns followed by successive ODS C18 HPLC revealed the presence of five dibromoalkaloids 5–9. The structures of the known compounds 5–8 were rapidly determined as 5,6-dibromotryptamine 5, N-methyl-5,6-dibromotryptamine (6) [7], N,N-dimethyl-5,6-dibromotryptamine (7) [8], and 5,6-dibromoabrine (8) [9] by comparison with literature data. The structure of the new metabolite, 5,6-dibromo-l-hypaphorine (9), was obtained through detailed examination of mass spectrometric data and extensive 1D and 2D NMR studies (Figure 2).

Bottom Line: 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.The sesquiterpene aureol (4), also isolated from Hyrtios sp., showed the most potent antioxidant activity with an ORAC value of 0.29.

View Article: PubMed Central - PubMed

Affiliation: Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 MNHN-CNRS, Muséum National d'Histoire Naturelle, 57 Rue Cuvier (C.P. 54), 75005 Paris, France.

ABSTRACT
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 A₂ (PLA₂), 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.

Show MeSH
Related in: MedlinePlus