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Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica.

Youssef DT, Shaala LA, Alshali KZ - Mar Drugs (2015)

Bottom Line: Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica.Compounds 1-3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans.These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. dyoussef@kau.edu.sa.

ABSTRACT
In the course of our continuing efforts to identify bioactive secondary metabolites from Red Sea marine invertebrates, we have investigated the sponge Hemimycale arabica. The antimicrobial fraction of an organic extract of the sponge afforded two new hydantoin alkaloids, hemimycalins A and B (2 and 3), together with the previously reported compound (Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione (1). The structures of the compounds were determined by extensive 1D and 2D NMR (COSY, HSQC and HMBC) studies and high-resolution mass spectral determinations. Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica. Compounds 1-3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans. In addition, compound 1 displayed moderate antiproliferative activity against the human cervical carcinoma (HeLa) cell line. These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

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Structures of compounds 1–3.
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marinedrugs-13-06609-f001: Structures of compounds 1–3.

Mentions: Compound 1 (Figure 1) was purified as yellow amorphous solid. Its molecular formula C10H8N2O3 was deduced from the positive HRESIMS (high-resolution electrospray ionisation mass spectrometry) pseudomolecular ion peak at m/z 227.0435 [M + Na]+. The structure of 1 was assigned as (Z)-5-(4-hydroxybenzylidene)-imidazolidine-2,4-dione [18,19] based on complete analysis of its NMR data (Table 1) and by comparison to literature data [18,19].


Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica.

Youssef DT, Shaala LA, Alshali KZ - Mar Drugs (2015)

Structures of compounds 1–3.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4663544&req=5

marinedrugs-13-06609-f001: Structures of compounds 1–3.
Mentions: Compound 1 (Figure 1) was purified as yellow amorphous solid. Its molecular formula C10H8N2O3 was deduced from the positive HRESIMS (high-resolution electrospray ionisation mass spectrometry) pseudomolecular ion peak at m/z 227.0435 [M + Na]+. The structure of 1 was assigned as (Z)-5-(4-hydroxybenzylidene)-imidazolidine-2,4-dione [18,19] based on complete analysis of its NMR data (Table 1) and by comparison to literature data [18,19].

Bottom Line: Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica.Compounds 1-3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans.These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. dyoussef@kau.edu.sa.

ABSTRACT
In the course of our continuing efforts to identify bioactive secondary metabolites from Red Sea marine invertebrates, we have investigated the sponge Hemimycale arabica. The antimicrobial fraction of an organic extract of the sponge afforded two new hydantoin alkaloids, hemimycalins A and B (2 and 3), together with the previously reported compound (Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione (1). The structures of the compounds were determined by extensive 1D and 2D NMR (COSY, HSQC and HMBC) studies and high-resolution mass spectral determinations. Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica. Compounds 1-3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans. In addition, compound 1 displayed moderate antiproliferative activity against the human cervical carcinoma (HeLa) cell line. These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

Show MeSH
Related in: MedlinePlus