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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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Underwater photograph of the Red Sea sponge Hemimycale arabica.
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marinedrugs-13-06609-f003: Underwater photograph of the Red Sea sponge Hemimycale arabica.

Mentions: The sponge was collected by hand off the Saudi Red Sea coast of Jazan (Ghurab, north side) (N 17°06′38.0″ E 42°04′01.9″) at depths ranging from 10 to 17 m in May 2013. The sponge (Figure 3) forms an encrusting soft mass of about 1–3 cm thick, covering rocks or dead corals. The outer color is deep bluish with a greenish-yellow interior. The sponge is very soft and easy to cut. The blue surface color is caused by a concentrated pigmented surface layer approximately 150 μm in thickness, which fades to a light beige color on preservation. The skeleton is plumose consisting of parallel loose bundles of thin spicules running from the substratum upwards through the sponge and fanning out at the surface. In between there are many loose spicules. Bundles have a diameter of 30–50 μm and contain 12–20 spicules in cross-section. Siliceous spicules are straight and thin, either strongyles (rounded at both ends) or styles (one end pointed), but otherwise similar in shape and size, ranging from 210–250 × 2–4 μm. These characters conform to the description of the type specimen of Hemimycale arabica, with which the present specimen has been compared. A voucher specimen is kept in the collections of the Naturalis Biodiversity Center at Leiden, The Netherlands, registration number ZMA Por. 16634. Another voucher specimen was deposited in the Red Sea Invertebrates Collection of the Department of Natural Products, Faculty of Pharmacy at King Abdulaziz University, under the code number DY-21. The sponge materials were kept frozen at −20 °C until processed.


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

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

Underwater photograph of the Red Sea sponge Hemimycale arabica.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-06609-f003: Underwater photograph of the Red Sea sponge Hemimycale arabica.
Mentions: The sponge was collected by hand off the Saudi Red Sea coast of Jazan (Ghurab, north side) (N 17°06′38.0″ E 42°04′01.9″) at depths ranging from 10 to 17 m in May 2013. The sponge (Figure 3) forms an encrusting soft mass of about 1–3 cm thick, covering rocks or dead corals. The outer color is deep bluish with a greenish-yellow interior. The sponge is very soft and easy to cut. The blue surface color is caused by a concentrated pigmented surface layer approximately 150 μm in thickness, which fades to a light beige color on preservation. The skeleton is plumose consisting of parallel loose bundles of thin spicules running from the substratum upwards through the sponge and fanning out at the surface. In between there are many loose spicules. Bundles have a diameter of 30–50 μm and contain 12–20 spicules in cross-section. Siliceous spicules are straight and thin, either strongyles (rounded at both ends) or styles (one end pointed), but otherwise similar in shape and size, ranging from 210–250 × 2–4 μm. These characters conform to the description of the type specimen of Hemimycale arabica, with which the present specimen has been compared. A voucher specimen is kept in the collections of the Naturalis Biodiversity Center at Leiden, The Netherlands, registration number ZMA Por. 16634. Another voucher specimen was deposited in the Red Sea Invertebrates Collection of the Department of Natural Products, Faculty of Pharmacy at King Abdulaziz University, under the code number DY-21. The sponge materials were kept frozen at −20 °C until processed.

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