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  • 1
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    Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium (2011)
    Details
    Publication Date: 2021-05-19
    Description: The chemical composition of the Caribbean sponge Pandaros acanthifolium was reinvestigated and led to the isolation of 12 new steroidal glycosides, namely, pandarosides E-J (1-6) and their methyl esters (7-12). Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. Like the previously isolated pandarosides A-D (13-16), the new compounds 1-12 share an unusual oxidized D-ring and a cis C/D ring junction. The absolute configurations of the aglycones were assigned by interpretation of CD spectra, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates. The majority of the metabolites showed in Vitro activity against three or four parasitic protozoa. Particularly active were the compounds 3 (pandaroside G) and its methyl ester (9), which potently inhibited the growth of Trypanosoma brucei rhodesiense (IC50 values 0.78 and 0.038 μM, respectively) and Leishmania donoVani (IC50’s 1.3 and 0.051 μM, respectively).
    Description: Published
    Description: Pandaros, steroidal saponins, structure elucidation, stereochemistry, antiprotozoal
    Keywords: Sponges ; Sponges
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 2
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    Contribution to the phytochemical study and biological activity of plants of Cuban flora (2011)
    Details
    Publication Date: 2021-05-19
    Description: Interest in natural products as a source for innovation in drug discovery and agrochemicals is still growing worldwide. Natural products, whose immense diversity has been appreciated for many years, may become in a rich source of novel chemical structures. Our country is a rich source of both biological and chemical diversity which may be useful as a source of novel chemical structures. Even when natural products have been used as medicinal agents for many years in Cuba, their use as agrochemicals are still limited. Thus, the present review focuses on recent advances in the studies on natural products performed by the “Centro de Estudios de Productos Naturales, CEPN” during the past ten years, highlighting on those with potential use as biomedical and agrochemicals. 15 plant species were studied; Agave brittoniana Trel. Subsp. brachypus A Álvarez de Zayas (Agavaceae); Juniperus barbadensis L. var. Lucayana (Britt.) RP Adams (Cupressaceae); Melia azedarach Linn. (Meliaceae); Tectona grandis Linn. f. (Lamiaceae); Lantana camara Linn. (Verbenaceae); Lantana trifolia Cham. (Verbenaceae); Citrus sinensis (Linn.) Osbeck cv Valencia (Ruta- ceae); Maytenus buxifolia (A Rich) Griseb (Celastraceae); Maytenus elaeodendroides Griseb (Celastraceae); Maytenus urquiolae B Mory (Celastraceae); Solanum americanum W. Mill (Solanaceae); Thalassia testudinum Kon. (Hydrocha- ritaceae); Sesbania rostrata Bremek & Oberm (Fabaceae); Pluchea carolinensis G Don (Asteraceae) and Ageratina havanensis (HB & K) RM King & Robinson (Asteraceae). By means of a bio-guided fractionation, isolated structures as well as semi-purified fractions were assayed as antioxidant, antiparasitic, antibiotic, insecticides, antifungal, and skin regenerating and healing effects. The strateg y employed allows us to discover novel secondary metabolites with potential for industrial development as pharmaceuticals and/or agrochemicals. Besides, in addition to the goal of discovering new bioactive agents, the presence of unique bioactive compounds notably contribute to increase the knowledge of plant species in Cuba.
    Description: Facultad de Química, Universidad de La Habana, UH
    Description: Este artículo es una compilacion de tesis de maestrias y doctorados, que ganó en el 2009 el Premio de la Academia de Ciencias de Cuba.
    Description: Published
    Description: Bioactivity of Cuban plants, flavonoids, saponins and steroidal sapogenins, terpenoids and triterpenoids, quinones and phenolic compounds
    Keywords: Products ; Chemical compounds ; Products ; Chemical compounds ; Bioactive compounds
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 3
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    Polar Alkaloids from the Caribbean Marine Sponge Niphates digitalis (2011)
    Details
    Publication Date: 2021-05-19
    Description: A method involving flash chromatography, semi-preparative phenylhexyl RP HPLC-DAD-ELSD combined with analytic polar-RP HPLC-DAD, was applied to separate and purify six highly nitrogenated bases and a bicyclic amidine alkaloid, the major components of the marine sponge Niphates digitalis. Their structures were identified as 1,8-diazabicyclo[5.4.0]undec-7- ene (1), deoxycytidine (2), phenylalanine (3), adenosine (4), deoxyguanosine (5), adenine (6) and thymidine (7) on the basis of spectroscopic data analyses. This is the first report of these compounds in a marine sponge belonging to the Niphates genus and the first evidence of the presence of 1 from a natural source.
    Description: Published
    Description: Marine sponge, Niphates digitalis, nucleosides, nucleobases, antimalarial activity, cytotoxicity
    Keywords: Cytotoxicity ; Sponges ; Sponges ; Cytotoxicity
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 4
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    Steroidal glycosides from the marine sponge Pandaros acanthifolium (2011)
    Details
    Publication Date: 2021-05-19
    Description: The chemical composition of the Caribbean sponge Pandaros sp. was investigated and led to the isolation of seven new steroidal glycosides namely pandarosides A-D (1, 3, 4 and 6) along with the three methyl esters of pandarosides A, C, and D (2, 5 and 7). Their structures were characterized as 3β-[β-glucopyranosyl-(1→2)-β-glucopyranosyloxyuronic acid]-16-hydroxy- 5α,14β-poriferast-16-ene-15,23-dione (1) and its methyl ester (2), 3β-[β- glucopyranosyloxyuronic acid]-16-hydroxy-5α,14β-poriferast-16-ene-15,23-dione (3), 3β-[β- glucopyranosyl-(1→2)-β-glucopyranosyloxyuronic acid]-16-hydroxy-5α,14β-cholest-16-ene- 15,23-dione (4) and its methyl ester (5), 3β-(β-glucopyranosyloxyuronic acid)-16-hydroxy- 5α,14β-cholest-16-ene-15,23-dione (6) and its methyl ester (7) on the basis of detailed spectroscopic analyses, including 2D NMR and HRESI-MS studies. Pandarosides A-D and their methyl esters (1-7) are all characterized by a rare 2-hydroxycyclopentenone D-ring with a 14β configuration.
    Description: Published
    Description: Marine sponge, Pandaros, steroidal glycosides, structure elucidation, stereochemistry
    Keywords: Sponges ; Sponges
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 5
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    Repair of UVB-Damaged Skin by the antioxidant sulphated flavone glycoside Thalassiolin B Isolated from the marine plant Thalassia testudinum Banks ex König (2011)
    Details
    Publication Date: 2021-05-19
    Description: Daily topical application of the aqueous ethanolic extract of the marine sea grass, Thalassia testudinum, on mice skin exposed to UVB radiation resulted in a dose dependent recovery of the skin macroscopic alterations over a 6-day period. Maximal effect (90%) occurred at a dose of 240 μg/cm2, with no additional effects at higher doses. Bioassay-guided fractionation of the plant extract resulted in the isolation of thalassiolin B (1). Topical application of 1 (240 μg/cm2) markedly reduces skin UVB-induced damage. In addition, thalassiolin B scavenged 2,2-diphenyl-2-picrylhydrazyl radical with an EC50=100 μg/ml. These results suggest that thalassiolin B is responsible for the skin regenerating effects of the crude extract of T. testudinum
    Description: Published
    Description: Flavonoids, Thalassiolin B, DPPH scavenged, antioxidant activity, Skin regenerating activity, Thalassia testudinum
    Keywords: Chemistry ; Pharmacology ; Chemistry ; Pharmacology
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 6
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    Las esponjas marinas como fuente de nuevas sustancias bioactivas. (2011)
    Details
    Publication Date: 2021-05-19
    Description: Marine sponges (Porifera) have drawn the attention from a broad number of researchers all over the world. These animals and their simbionts are specialized in chemical warfare, producing biologically active chemical substances as an effective defense against predators. They have been considered a goldmine to chemists, from which have been discovered more than 6000 novel structures; many of them, with enormous biomedical applications, mainly against cancer, but also against bacteria, viruses and other diseases. Some of the sponge-derived drugs are available in the market, such as: Ara-A (antiviral) and Ara-C (anticancer), but there are diverse bioactive compounds under clinical trials. In Cuba, the researches related to the isolation of compounds from marine sponges are scarce and the initial studies were about pharmacological evaluations of extracts and fractions. In recent studies, three sponges were investigated (Agelas cerebrum, Niphates digitalis and Pandaros acanthifolium), from which were isolated and identified 45 metabolites, two of them were isolated for the first time as natural products, including the discovery of 30 novel metabolites, dividing in two new families of steroidal saponins with uncommon chemical characteristics and potential against several parasitic protozoa and tumor human cell lines.
    Description: Published
    Description: marine sponges, novel compounds, bioactive metabolites, antiparasitic, antitumoral
    Keywords: Sponges ; Organic compounds ; Antiparasitic agents
    Repository Name: AquaDocs
    Type: Journal Contribution , Refereed , Article
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  • 7
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    Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum (2011)
    Sociedade Brasileira de Química
    Details
    Publication Date: 2021-05-19
    Description: Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source.
    Description: Published
    Description: Agelas cerebrum, bromopyrrole alkaloids, antitumoral, antiprotozoal activity
    Keywords: Chemistry ; Alkaloids ; Sponges ; Alkaloids ; Sponges ; Chemistry
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 8
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    Marine sponges as a source of new bioactive substances (2011)
    Details
    Publication Date: 2021-05-19
    Description: Las esponjas marinas (Porifera) han atraído la atención de un gran número de científicos alrededor del mundo. Estos animales y sus simbiontes utilizan mecanismos de defensa química, basados en la producción de compuestos biologicamente activos que utlizan para protegerse de posibles depredadores. Son considerados una mina de oro para los químicos y se han descubierto más de 6000 estructuras novedosas, muchas de ellas con enormes aplicaciones biomédicas, fundamentalmente contra el cáncer, pero también contra diversas bacterias, virus y otras enfermedades. Algunos de los fármacos derivados de esponjas se encuentran disponibles en el mercado, tal es el caso Ara-A (antiviral) y de la Ara-C (antitumoral), pero existen diversos compuestos bioactivos en ensayos clínicos. En Cuba, las investigaciones relacionadas con compuestos obtenidos de esponjas marinas son muy escasas, los descubrimientos iniciales se desarrollaron en el campo farmacológico y solamente en extractos o fracciones. En estudios recientes, se investigaron tres esponjas (Agelas cerebrum, Niphates digitalis y Pandaros acanthifolium), a partir de las cuales se aislaron e identificaron 45 metabolitos, dos de ellos fueron nuevos productos naturales y 30 resultaron metabolitos novedosos, pertenecientes a dos nuevas familias de saponinas esteroidales con características químicas poco comunes y efecto sobre varios parásitos protozoarios, así como contra varias líneas celulares de carcinoma humano.
    Description: Marine sponges (Porifera) have drawn the attention from a broad number of researchers all over the world. These animals and their simbionts are specialized in chemical warfare, producing biologically active chemical substances as an effective defense against predators. They have been considered a goldmine to chemists, from which have been discovered more than 6000 novel structures; many of them, with enormous biomedical applications, mainly against cancer, but also against bacteria, viruses and other diseases. Some of the sponge- derived drugs are available in the market, such as: Ara-A (antiviral) and Ara-C (anticancer), but there are diverse bioactive compounds under clinical trials. In Cuba, the researches related to the isolation of compounds from marine sponges are scarce and the initial studies were about pharmacological evaluations of extracts and fractions. In recent studies, three sponges were investigated (Agelas cerebrum, Niphates digitalis and Pandaros acanthifolium), from which were isolated and identified 45 metabolites, two of them were isolated for the first time as natural products, including the discovery of 30 novel metabolites, dividing in two new families of steroidal saponins with uncommon chemical characteristics and potential against several parasitic protozoa and tumor human cell lines.
    Description: Published
    Description: novel compounds, antiparasitic, antitumoral
    Keywords: Chemical compounds ; Sponges ; Sponges ; Chemical compounds ; Bioactive compounds
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 9
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    Parazoanthines A-E: Hydantoin Alkaloids from the Mediterranean Sea Anemone Parazoanthus axinellae (2011)
    Details
    Publication Date: 2021-05-19
    Description: Five new hydantoin alkaloids, named parazoanthines A-E (1-5), were isolated as the major constituents of the Mediterranean sea anemone Parazoanthus axinellae. Their structural elucidation was achieved through NMR spectroscopic and mass spectrometric analyses. The absolute configuration of the chiral compounds 1 and 4 was determined by comparison between experimental and TDDFT calculated CD spectra. The configuration of the trisubstituted double bond of 2, 3, and 5 was deduced from the 3JH6-C4 coupling constant value. This family of alkaloids represents the first example of natural 3,5- disubstituted hydantoins which do not exhibit a methyl at N-3. All compounds were tested for their natural toxicity (Microtox® assay) and parazoanthine C (3) exhibited the highest natural toxicity. 3 Relatively few chemical studies of zoanthids have been reported so far, despite evidence of their rich natural products chemistry.1 Colonial sea anemones of the genus Parazoanthus have been identified in almost all the oceans and they often have been described as epibionts of marine sponges belonging to the Agelas or Axinella genera. As sponges are known to exude toxic compounds, these zoanthids must have developed adaptative tools to minimize effects of such toxins. Two groups of compounds have been described from Parazoanthus species: fluorescent guanidine alkaloids of the zoanthoxanthin families,2-7 and ecdysteroids.8 As part of an ongoing research program to investigate the chemodiversity of Mediterranean invertebrates,9 specimens of Parazoanthus axinellae were collected near Marseilles (Plane island) as epibionts of the sponge Axinella damicornis. Because the LC–MS analyses of their crude extracts evidenced brominated compounds as major constituents, we decided to undertake the full chemical study of this species from which only zoanthoxanthins have been previously described.2,3 We report herein the isolation and structural characterization of a new class of alkaloids named parazoanthines A-E (1-5) with a rare 3,5-disubstituted hydantoin core.
    Description: Published
    Description: sea anemones, Parazoanthus, structure elucidation, stereochemistry
    Keywords: Alkaloids ; Alkaloids
    Repository Name: AquaDocs
    Type: Journal Contribution
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  • 10
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    Actividad antioxidante del alga Ulva fasciata Delile sometida a distintos niveles de contaminación marina (2009)
    Details
    Publication Date: 2021-05-19
    Description: Ha sido demostrado, por otros autores, que el alga Ulva fasciata Delile posee una actividad antioxidante promisoria y en el presente trabajo evaluamos si la actividad antioxidante de muestras de esta alga puede ser influenciada por la adsorción de metales, pesados y otros por parte del alga. U. fasciata fue colectada en tres zonas de las costas de la Ciudad de la Habana que presentan diferentes niveles de eutrofización: 1) la desembocadura del Río Quibú, un río que atraviesa una importante zona industrial de la capital cubana y en la cual la concentración de metales acumulados por el alga fue mayor; 2) la zona del Malecón habanero, que recibe la contaminación de la bahía de la Habana y del Río Almendares pero no de forma directa, donde presentó valores intermedios de la adsorción de metales y 3) la Playa Bacuranao, una zona turística con menor nivel de contaminación en sus aguas y donde el nivel de metales adsorbido por el alga fue menor. Los extractos obtenidos de las algas colectadas en la desembocadura del Río Quibú presentaron una mayor actividad antioxidante y menor fue la actividad de los obtenidos de las algas de la Playa Bacuranao, mientras que los extractos de las algas del Malecón habanero tuvieron una actividad intermedia.
    Description: Published
    Description: Actividad antioxidante, Ulva fasciata Delile
    Keywords: Marine environment ; Heavy metals ; Algae ; Algae ; Marine environment ; Heavy metals
    Repository Name: AquaDocs
    Type: Journal Contribution
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