Red Sea Sponge Extract Induced Growth Inhibition and Apoptosis in Breast MCF-7 and Hepatic HepG-2 Cancer Cell Lines in 2D and 3D Cell Cultures.

Introduction: The increasing incidence of cancer diseases necessitates the urgent exploration of new bioactive compounds. One of the trends in drug discovery is marine sponges which is gaining significant support due to the abundant production of natural pharmaceutical compounds obtained from marine ecosystems. This study evaluates the anticancer properties of an organic extract from the Red Sea sponge on HepG-2 and MCF-7 cancer cell lines.

Leptochelins A-C, Cytotoxic Metallophores Produced by Geographically Dispersed Strains of Marine Cyanobacteria.

Metals are important cofactors in the metabolic processes of cyanobacteria, including photosynthesis, cellular respiration, DNA replication, and the biosynthesis of primary and secondary metabolites. In adaptation to the marine environment, cyanobacteria use metallophores to acquire trace metals when necessary as well as to reduce potential toxicity from excessive metal concentrations. Leptochelins A-C were identified as structurally novel metallophores from three geographically dispersed cyanobacteria of the genus .

Anti-Infective Secondary Metabolites of the Marine Cyanobacterium Morphotype between 1979 and 2022.

Cyanobacteria ascribed to the genus (Family Oscillatoriaceae) represent a potential therapeutic gold mine of chemically and biologically diverse natural products that exhibit a wide array of biological properties. Phylogenetic analyses have established the 'morpho-type' as a highly polyphyletic group and have resulted in taxonomic revision and description of an additional six new cyanobacterial genera in the same family to date. Among the most prolific marine cyanobacterial producers of biologically active compounds are the species (previously then ) (previously ), and .

Neuroprotective Effect of Red Sea Marine Sponge Extract Using In Vitro and In Vivo Diabetic Peripheral Neuropathy Models.

Diabetic peripheral neuropathy (DPN) is a common complication of diabetes. Oxidative stress plays an important role in the pathophysiology of DPN. Red Sea marine sponge extract has a promising neuroprotective effect, presumably owing to its antioxidant and anti-inflammatory properties.

Psammaplysins: Insights from Natural Sources, Structural Variations, and Pharmacological Properties.

Marine natural products (MNPs) continue to be in the spotlight in the global drug discovery endeavor. Currently, more than 32,000 structurally diverse secondary metabolites from marine sources have been isolated, making MNPs a vital source for researchers to look for novel drug candidates. The marine-derived psammaplysins possess the rare and unique 1,6-dioxa-2-azaspiro [4.

Asperopiperazines A and B: Antimicrobial and Cytotoxic Dipeptides from a Tunicate-Derived Fungus sp. DY001.

Investigation of the cytotoxic fractions of the ethyl acetate extract of the fermentation broth of the tunicate-derived sp. DY001 afforded two new dipeptides, asperopiperazines A and B ( and ), along with the previously reported compounds (+)-citreoisocoumarin () and (-)-6,8-di--methylcitreoisocoumarin (). Analyses of the 1D and 2D NMR spectroscopic data of the compounds supported their structural assignments.

Cytotoxic Phenylpropanoid Derivatives and Alkaloids from the Flowers of L.

Regarding our growing interest in identifying biologically active leads from Amaryllidaceous plants, the flowers of L. (Amaryllidaceae) were investigated. Purification of the cytotoxic fractions of the alcoholic extract of the flowers gave a new glycoside, 3-[4-(-D-glucopyranosyloxy)phenyl]-2-()-propenoic acid methyl ester (), together with the previously reported compounds 3-methoxy-4-(-D-glucopyranosyloxy)benzoic acid methyl ester (), 3-(4-methoxyphenyl)propan-1-ol-1--D-glucopyranoside (), ()-3-(4-hydroxyphenyl)acrylic acid methyl ester (), caffeic acid (), dihydrocaffeic acid methyl ester (), and pancratistatin ().

Hemimycalins C-E; Cytotoxic and Antimicrobial Alkaloids with Hydantoin and 2-Iminoimidazolidin-4-one Backbones from the Red Sea Marine Sponge sp.

In the course of our continuing efforts to identify bioactive secondary metabolites from Red Sea marine sponges, we have investigated the sponge sp. The cytotoxic fraction of the organic extract of the sponge afforded three new compounds, hemimycalins C-E (-). Their structural assignments were obtained via analyses of their one- and two-dimensional NMR spectra and HRESI mass spectrometry.

Fusaripyridines A and B; Highly Oxygenated Antimicrobial Alkaloid Dimers Featuring an Unprecedented 1,4-Bis(2-hydroxy-1,2-dihydropyridin-2-yl)butane-2,3-dione Core from the Marine Fungus sp. LY019.

The fungal strain, sp. LY019, was obtained from the Red Sea sponge . Bioassay-directed partition of the antimicrobial fraction of the extract of the culture of the fungus provided two dimeric alkaloids, fusaripyridines A and B ( and ).

Psammaceratin A: A Cytotoxic Psammaplysin Dimer Featuring an Unprecedented (2Z,3Z)-2,3-Bis(aminomethylene)succinamide Backbone from the Red Sea Sponge .

Bioassay-guided partition of the extract of the Red Sea sponge and HPLC purification of the active fraction gave a psammaplysin dimer, psammaceratin A (), along with psammaplysin A (). The dimer comprises two units of psammaplysin A () connected via the terminal amines with an unprecedented (2,3)-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.

Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5()-dione Backbone from the Red Sea Sponge .

Investigation of the Red Sea sponge gave two novel alkaloids, magnificines A and B ( and ) and a new β-ionone derivative, (±)-negombaionone (), together with the known latrunculin B () and 16--latrunculin B (). The analysis of the NMR and HRESIMS spectra supported the planar structures and the relative configurations of the compounds. The absolute configurations of magnificines A and B were determined by the analysis of the predicted and experimental ECD spectra.

Marine biomimetics: bromotyrosines loaded chitinous skeleton as source of antibacterial agents.

Unlabelled: The marine sponges of the order Verongiida (Demospongiae: Porifera) have survived on our planet for more than 500 million years due to the presence of a unique strategy of chemical protection by biosynthesis of more than 300 derivatives of biologically active bromotyrosines as secondary metabolites. These compounds are synthesized within spherulocytes, highly specialized cells located within chitinous skeletal fibers of these sponges from where they can be extruded in the sea water and form protective space against pathogenic viruses, bacteria and other predators. This chitin is an example of unique biomaterial as source of substances with antibiotic properties.

Marine-Derived Biomolecules.

The world's oceans have been shown to be rich habitats with great biodiversity and chemical entities with proven bioactivities related to cancer, inflammation, epilepsy, the immunomodulatory system, microbial and parasitic infections, and many others [...

Pseudoceratonic Acid and Moloka'iamine Derivatives from the Red Sea Verongiid Sponge .

During an investigation of the chemistry of the Red Sea Verongiid sponge we discovered a small molecule, pseudoceratonic acid (), along with the new moloka'iamine derivatives, ceratinines N (), O (), and the previously reported compounds moloka'iamine (), hydroxymoloka'iamine () and ceratinamine (). The structural assignments of - 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.

Antimicrobial Chlorinated 3-Phenylpropanoic Acid Derivatives from the Red Sea Marine Actinomycete LY001.

The actinomycete strain LY001 was purified from the sponge . Fractionation of the antimicrobial extract of the culture of the actinomycete afforded three new natural chlorinated derivatives of 3-phenylpropanoic acid, 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid (), 3-(3,5-dichloro-4-hydroxyphenyl)propanoic acid methyl ester (), and 3-(3-chloro-4-hydroxyphenyl)propanoic acid (), together with 3-phenylpropanoic acid (), -cinnamic acid (), and the diketopiperazine alkaloids cyclo(l-Phe--4-OH-l-Pro) () and cyclo(l-Phe--4-OH-d-Pro) () were isolated. Interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HRESIMS) data of - supported their assignments.

Secondary Metabolites of the Genus : A Comprehensive Review of Chemical Diversity and Pharmacological Properties.

Tunicates (ascidians) are common marine invertebrates that are an exceptionally important source of natural products with biomedical and pharmaceutical applications, including compounds that are used clinically in cancers. Among tunicates, the genus is important because it includes the most species, and it belongs to the most speciose family (Didemnidae). The genus includes the species , , , and , as well as others, which are well known for their chemically diverse secondary metabolites.

Cytotoxic Psammaplysin Analogues from the Verongid Red Sea Sponge Species.

As part of our ongoing interest to identify bioactive chemical entities from marine invertebrates, the Red Sea specimen of the Verongid sponge species was studied. Repeated chromatographic fractionation of the methanolic extract of the sponge and HPLC purification of the cytotoxic fractions led to the isolation and the identification of two new compounds, psammaplysin Z and 19-hydroxypsammaplysin Z ( and ), together with the previously reported psammaplysins A () and E (). The structural determination of - was supported by interpretation of their NMR and high-resolution mass spectra.

Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived Species.

Fractionation and purification of the ethyl acetate extract of the culture of a sponge-derived actinomycete, species Call-36, resulted in the isolation and identification of a new diketopiperazine, actinozine A (), cyclo(2-OH-d-Pro-l-Leu) (), two new nucleosides, thymidine-3-mercaptocarbamic acid () and thymidine-3-thioamine (), together with cyclo(d-Pro-l-Phe) () and cyclo(l-Pro-l-Phe) (). The structure assignments of the compounds were carried out by interpretation of 1D and 2D NMR data and mass spectral determinations. The absolute configurations of and were determined by Marfey's method and by comparison of the experimental and TDDFT-calculated ECD spectra.

New Source of 3D Chitin Scaffolds: The Red Sea Demosponge (Pseudoceratinidae, Verongiida).

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.

Jizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea.

Jizanpeptins A-E (1-5) are micropeptin depsipeptides isolated from a Red Sea specimen of a Symploca sp. cyanobacterium. The planar structures of the jizanpeptins were established using NMR spectroscopy and mass spectrometry and contain 3-amino-6-hydroxy-2-piperidone (Ahp) as one of eight residues in a typical micropeptin motif, as well as a side chain terminal glyceric acid sulfate moiety.

Discovery of chitin in skeletons of non-verongiid Red Sea demosponges.

Marine demosponges (Porifera: Demospongiae) are recognized as first metazoans which have developed over millions of years of evolution effective survival strategies based on unique metabolic pathways to produce both biologically active secondary metabolites and biopolymer-based stiff skeletons with 3D architecture. Up to date, among marine demosponges, only representatives of the Verongiida order have been known to synthetize biologically active substances as well as skeletons made of structural polysaccharide chitin. This work, to our knowledge, demonstrates for the first time that chitin is an important structural component within skeletons of non-verongiid demosponges Acarnus wolffgangi and Echinoclathria gibbosa collected in the Red Sea.

First Report on Chitin in a Non-Verongiid Marine Demosponge: The Mycale euplectellioides Case.

Sponges (Porifera) are recognized as aquatic multicellular organisms which developed an effective biochemical pathway over millions of years of evolution to produce both biologically active secondary metabolites and biopolymer-based skeletal structures. Among marine demosponges, only representatives of the Verongiida order are known to synthetize biologically active substances as well as skeletons made of structural polysaccharide chitin. The unique three-dimensional (3D) architecture of such chitinous skeletons opens the widow for their recent applications as adsorbents, as well as scaffolds for tissue engineering and biomimetics.

The demosponge Pseudoceratina purpurea as a new source of fibrous chitin.

Among marine demosponges (Porifera: Demospongiae), only representatives of the order Verongiida have been recognized to synthetize both biologically active substances as well as scaffolds-like fibrous skeletons made of structural aminopolysaccharide chitin. The unique 3D architecture of such scaffolds open perspectives for their applications in waste treatment, biomimetics and tissue engineering. Here, we focus special attention to the demosponge Pseudoceratina purpurea collected in the coastal waters of Singapore.

Cytotoxic and Antimicrobial Compounds from the Marine-Derived Fungus, Penicillium Species.

The organic extract of liquid cultures of the marine-derived sp. was investigated. Fractionation of the extracts of the fungus led to the purification and identification of two new compounds, penicillatides A () and B (), together with the previously reported cyclo(-Pro-Phe) () and cyclo(-Pro-Phe) ().

Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri.

Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge Stylissa carteri and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, Z-3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1H-pyrrole-2-carbamide], nine compounds were monobrominated [(-) clathramide C, agelongine, (+) manzacidin A, (-) 3-bromomanzacidin D, Z-spongiacidin D, Z-hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1H-pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., E-debromohymenialdisine and aldisine.