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Keywords = Pseudoceratina arabica

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9 pages, 1355 KiB  
Article
Psammaceratin A: A Cytotoxic Psammaplysin Dimer Featuring an Unprecedented (2Z,3Z)-2,3-Bis(aminomethylene)succinamide Backbone from the Red Sea Sponge Pseudoceratina arabica
by Diaa T. A. Youssef, Hani Z. Asfour and Lamiaa A. Shaala
Mar. Drugs 2021, 19(8), 433; https://doi.org/10.3390/md19080433 - 29 Jul 2021
Cited by 9 | Viewed by 2535
Abstract
Bioassay-guided partition of the extract of the Red Sea sponge Pseudoceratina arabica and HPLC purification of the active fraction gave a psammaplysin dimer, psammaceratin A (1), along with psammaplysin A (2). The dimer comprises two units of psammaplysin A [...] Read more.
Bioassay-guided partition of the extract of the Red Sea sponge Pseudoceratina arabica and HPLC purification of the active fraction gave a psammaplysin dimer, psammaceratin A (1), along with psammaplysin A (2). The dimer comprises two units of psammaplysin A (2) connected via the terminal amines with an unprecedented (2Z,3Z)-2,3-bis(aminomethylene)succinamide moiety, and it represents the first dimer to be identified among the psammaplysin family. Data from 1D- and 2D-NMR and HRMS supported the chemical structures of the compounds. Psammaceratin A (1) and psammaplysin A (2) exhibited significant growth inhibition of HCT 116, HeLa, and MBA-MB-231 cells down to 3.1 μM. Full article
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12 pages, 2298 KiB  
Article
Pseudoceratonic Acid and Moloka’iamine Derivatives from the Red Sea Verongiid Sponge Pseudoceratina arabica
by Lamiaa A. Shaala and Diaa T. A. Youssef
Mar. Drugs 2020, 18(11), 525; https://doi.org/10.3390/md18110525 - 23 Oct 2020
Cited by 15 | Viewed by 2539
Abstract
During an investigation of the chemistry of the Red Sea Verongiid sponge Pseudoceratina arabica, we discovered a small molecule, pseudoceratonic acid (1), along with the new moloka’iamine derivatives, ceratinines N (2), O (3), and the previously reported [...] Read more.
During an investigation of the chemistry of the Red Sea Verongiid sponge Pseudoceratina arabica, we discovered a small molecule, pseudoceratonic acid (1), along with the new moloka’iamine derivatives, ceratinines N (2), O (3), and the previously reported compounds moloka’iamine (4), hydroxymoloka’iamine (5) and ceratinamine (6). The structural assignments of 16 were accomplished by interpretation of their NMR and HRESIMS spectral data. Pseudoceratonic acid possesses a dibrominated hydrazine-derived functional group not found in any reported chemical compound. Pseudoceratonic acid selectively inhibited the growth of E. coli and S. aureus, while ceratinine N selectively inhibited C. albicans. Further, ceratinine N showed potent cytotoxic effects against the triple-negative breast cancer, colorectal carcinoma, and human cervical carcinoma cell lines down to 2.1 µM. Full article
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17 pages, 6676 KiB  
Article
New Source of 3D Chitin Scaffolds: The Red Sea Demosponge Pseudoceratina arabica (Pseudoceratinidae, Verongiida)
by Lamiaa A. Shaala, Hani Z. Asfour, Diaa T. A. Youssef, Sonia Żółtowska-Aksamitowska, Marcin Wysokowski, Mikhail Tsurkan, Roberta Galli, Heike Meissner, Iaroslav Petrenko, Konstantin Tabachnick, Viatcheslav N. Ivanenko, Nicole Bechmann, Lyubov V. Muzychka, Oleg B. Smolii, Rajko Martinović, Yvonne Joseph, Teofil Jesionowski and Hermann Ehrlich
Mar. Drugs 2019, 17(2), 92; https://doi.org/10.3390/md17020092 - 1 Feb 2019
Cited by 36 | Viewed by 5804
Abstract
The bioactive bromotyrosine-derived alkaloids and unique morphologically-defined fibrous skeleton of chitin origin have been found recently in marine demosponges of the order Verongiida. The sophisticated three-dimensional (3D) structure of skeletal chitinous scaffolds supported their use in biomedicine, tissue engineering as well as in [...] Read more.
The bioactive bromotyrosine-derived alkaloids and unique morphologically-defined fibrous skeleton of chitin origin have been found recently in marine demosponges of the order Verongiida. The sophisticated three-dimensional (3D) structure of skeletal chitinous scaffolds supported their use in biomedicine, tissue engineering as well as in diverse modern technologies. The goal of this study was the screening of new species of the order Verongiida to find another renewable source of naturally prefabricated 3D chitinous scaffolds. Special attention was paid to demosponge species, which could be farmed on large scale using marine aquaculture methods. In this study, the demosponge Pseudoceratina arabica collected in the coastal waters of the Egyptian Red Sea was examined as a potential source of chitin for the first time. Various bioanalytical tools including scanning electron microscopy (SEM), fluorescence microscopy, FTIR analysis, Calcofluor white staining, electrospray ionization mass spectrometry (ESI-MS), as well as a chitinase digestion assay were successfully used to confirm the discovery of α-chitin within the skeleton of P. arabica. The current finding should make an important contribution to the field of application of this verongiid sponge as a novel renewable source of biologically-active metabolites and chitin, which are important for development of the blue biotechnology especially in marine oriented biomedicine. Full article
(This article belongs to the Special Issue Marine-Derived Products for Biomedicine)
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17 pages, 11250 KiB  
Article
Subereamolline A as a Potent Breast Cancer Migration, Invasion and Proliferation Inhibitor and Bioactive Dibrominated Alkaloids from the Red Sea Sponge Pseudoceratina arabica
by Lamiaa A. Shaala, Diaa T. A. Youssef, Mansour Sulaiman, Fathy A. Behery, Ahmed I. Foudah and Khalid A. El Sayed
Mar. Drugs 2012, 10(11), 2492-2508; https://doi.org/10.3390/md10112492 - 8 Nov 2012
Cited by 47 | Viewed by 8793
Abstract
A new collection of several Red Sea sponges was investigated for the discovery of potential breast cancer migration inhibitors. Extracts of the Verongid sponges Pseudoceratina arabica and Suberea mollis were selected. Bioassay-directed fractionation of both sponges, using the wound-healing assay, resulted into the [...] Read more.
A new collection of several Red Sea sponges was investigated for the discovery of potential breast cancer migration inhibitors. Extracts of the Verongid sponges Pseudoceratina arabica and Suberea mollis were selected. Bioassay-directed fractionation of both sponges, using the wound-healing assay, resulted into the isolation of several new and known brominated alkaloids. Active fractions of the sponge Pseudoceratina arabica afforded five new alkaloids, ceratinines A–E (26), together with the known alkaloids moloka’iamine (1), hydroxymoloka’iamine (7) and moloka’iakitamide (8). The active fraction of the sponge Suberea mollis afforded the three known alkaloids subereamolline A (9), aerothionin (10) and homoaerothionin (11). Ceratinine B (3) possesses an unprecedented 5,7-dibrominated dihydroindole moiety with an epoxy ring on the side chain of a fully substituted aromatic moiety. Ceratinines D (5) and E (6) possess a terminal formamide moiety at the ethylamine side chain. Subereamolline A (9) potently inhibited the migration and invasion of the highly metastatic human breast cancer cells MDA-MB-231 at the nanomolar doses. Subereamolline A and related brominated alkaloids are novel scaffolds appropriate for further future use for the control of metastatic breast cancer. Full article
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