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Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea.

Esposito G, Teta R, Miceli R, Ceccarelli LS, Della Sala G, Camerlingo R, Irollo E, Mangoni A, Pirozzi G, Costantino V - Mar Drugs (2015)

Bottom Line: The study of the secondary metabolites contained in the organic extract of Caribbean sponge Smenospongia aurea led to the isolation of smenothiazole A (3) and B (4), hybrid peptide/polyketide compounds.Assays performed using four solid tumor cell lines showed that smenothiazoles exert a potent cytotoxic activity at nanomolar levels, with selectivity over ovarian cancer cells and a pro-apoptotic mechanism.

View Article: PubMed Central - PubMed

Affiliation: The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy. germana.esposito@unina.it.

ABSTRACT
The study of the secondary metabolites contained in the organic extract of Caribbean sponge Smenospongia aurea led to the isolation of smenothiazole A (3) and B (4), hybrid peptide/polyketide compounds. Assays performed using four solid tumor cell lines showed that smenothiazoles exert a potent cytotoxic activity at nanomolar levels, with selectivity over ovarian cancer cells and a pro-apoptotic mechanism.

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Fragment ions observed in the high-resolution ESI MS/MS spectrum of smenothiazole A (3) and B (4).
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marinedrugs-13-00444-f003: Fragment ions observed in the high-resolution ESI MS/MS spectrum of smenothiazole A (3) and B (4).

Mentions: As for the peptide part of the molecule, analysis of the COSY and TOCSY spectra led to the identification of a valine residue (α proton at δ 4.54) and a proline residue (α proton at δ 5.27) (see Table 1 for the assignments). The connection between the Val residue and the polyketide carbonyl group (C-13) was demonstrated by the HMBC correlation of H-9 with C-13 and the connection between Val and Pro residues by HMBC of both H-4 and H-9 with the carbonyl carbon atom at δ 173.5 (C-8). Finally, the remaining atoms required by the molecular formula (1 S, 1 N, 3 C and 2 H) formed a thiazole ring linked to the proline α carbon, as shown by the two doublets at δ 7.71 (H-1) and 7.48 (H-2) in the proton spectrum and the HMBC correlations between H-2 and H-4 with the carbon atom at δ 174.4 (C-3). Finally, a high resolution MS/MS spectrum was recorded using the sodiated pseudomolecular ion peak of 3 (m/z 508) as the parent ion. All of the observed fragment ions (Figure 3a) were in full agreement with the proposed structure.


Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea.

Esposito G, Teta R, Miceli R, Ceccarelli LS, Della Sala G, Camerlingo R, Irollo E, Mangoni A, Pirozzi G, Costantino V - Mar Drugs (2015)

Fragment ions observed in the high-resolution ESI MS/MS spectrum of smenothiazole A (3) and B (4).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4306946&req=5

marinedrugs-13-00444-f003: Fragment ions observed in the high-resolution ESI MS/MS spectrum of smenothiazole A (3) and B (4).
Mentions: As for the peptide part of the molecule, analysis of the COSY and TOCSY spectra led to the identification of a valine residue (α proton at δ 4.54) and a proline residue (α proton at δ 5.27) (see Table 1 for the assignments). The connection between the Val residue and the polyketide carbonyl group (C-13) was demonstrated by the HMBC correlation of H-9 with C-13 and the connection between Val and Pro residues by HMBC of both H-4 and H-9 with the carbonyl carbon atom at δ 173.5 (C-8). Finally, the remaining atoms required by the molecular formula (1 S, 1 N, 3 C and 2 H) formed a thiazole ring linked to the proline α carbon, as shown by the two doublets at δ 7.71 (H-1) and 7.48 (H-2) in the proton spectrum and the HMBC correlations between H-2 and H-4 with the carbon atom at δ 174.4 (C-3). Finally, a high resolution MS/MS spectrum was recorded using the sodiated pseudomolecular ion peak of 3 (m/z 508) as the parent ion. All of the observed fragment ions (Figure 3a) were in full agreement with the proposed structure.

Bottom Line: The study of the secondary metabolites contained in the organic extract of Caribbean sponge Smenospongia aurea led to the isolation of smenothiazole A (3) and B (4), hybrid peptide/polyketide compounds.Assays performed using four solid tumor cell lines showed that smenothiazoles exert a potent cytotoxic activity at nanomolar levels, with selectivity over ovarian cancer cells and a pro-apoptotic mechanism.

View Article: PubMed Central - PubMed

Affiliation: The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy. germana.esposito@unina.it.

ABSTRACT
The study of the secondary metabolites contained in the organic extract of Caribbean sponge Smenospongia aurea led to the isolation of smenothiazole A (3) and B (4), hybrid peptide/polyketide compounds. Assays performed using four solid tumor cell lines showed that smenothiazoles exert a potent cytotoxic activity at nanomolar levels, with selectivity over ovarian cancer cells and a pro-apoptotic mechanism.

Show MeSH
Related in: MedlinePlus