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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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Most significant correlations provided by the COSY, HMBC and ROESY 2D NMR spectra of smenothiazole A (3) and B (4).
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marinedrugs-13-00444-f002: Most significant correlations provided by the COSY, HMBC and ROESY 2D NMR spectra of smenothiazole A (3) and B (4).

Mentions: As a result of the presence of several allylic and homoallylic couplings, all of the protons of the polyketide part of the molecule turned out to be part of a single spin system. Thus, the COSY spectrum displayed long-range coupling of: (i) the ortho phenyl protons at δ 7.19 (H-22/H-26) with the methylene protons at δ 3.44 (H2-20); (ii) the olefinic proton at δ 6.12 (H-19) with H2-20 and the methylene protons at δ 3.03 (H2-17); and (iii) the methyl protons at δ 1.79 (H3-15) with H2-17 and the olefinic proton at δ 6.15 (H-16). The structure of the polyketide part of smenothiazole A (3) was confirmed by an extensive network of HMBC correlations (Figure 2), which additionally allowed us to assign all of the nonprotonated carbon atoms in this moiety, including the amide carbonyl carbon atom at δ 172.2 (C-13). The presence of a chlorine carbon atom at C-19 was inferred by the chemical shift of C-19 and C-20, both very close to those of the corresponding atoms of smenamide A (1) [6].


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)

Most significant correlations provided by the COSY, HMBC and ROESY 2D NMR spectra 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-f002: Most significant correlations provided by the COSY, HMBC and ROESY 2D NMR spectra of smenothiazole A (3) and B (4).
Mentions: As a result of the presence of several allylic and homoallylic couplings, all of the protons of the polyketide part of the molecule turned out to be part of a single spin system. Thus, the COSY spectrum displayed long-range coupling of: (i) the ortho phenyl protons at δ 7.19 (H-22/H-26) with the methylene protons at δ 3.44 (H2-20); (ii) the olefinic proton at δ 6.12 (H-19) with H2-20 and the methylene protons at δ 3.03 (H2-17); and (iii) the methyl protons at δ 1.79 (H3-15) with H2-17 and the olefinic proton at δ 6.15 (H-16). The structure of the polyketide part of smenothiazole A (3) was confirmed by an extensive network of HMBC correlations (Figure 2), which additionally allowed us to assign all of the nonprotonated carbon atoms in this moiety, including the amide carbonyl carbon atom at δ 172.2 (C-13). The presence of a chlorine carbon atom at C-19 was inferred by the chemical shift of C-19 and C-20, both very close to those of the corresponding atoms of smenamide A (1) [6].

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