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Abstract Marine Natural Products (MNPs) isolated from samples collected in Colombia have been an object of study since the early 1980's; however, this information is neither integrated nor compiled. This systematic review describes the articles published in scientific journals up to December 2019. 173 papers met the inclusion criteria of focusing on MNPs obtained from specimens collected from Colombian seas; all original papers written in English, Portuguese or Spanish. The selected papers were mostly authored by researchers from Colombian groups, with low interaction amongst themselves. 99.4% of the papers studied samples collected from the Caribbean Sea; 183 species were studied, mainly sponges and octocorals. In this study, 1,690 compounds (238 new ones) were reviewed, mainly diterpenes and sterol derivatives. Of the selected papers, 76.8% measured various biological activities, including antibiotic (34%) and anticancer (30%). These papers were published in 51 journals (74.6% were international). In conclusion, scientific work on natural marine products of Colombian origin has incremented over time. The most relevant opportunities to address and fill existing gaps comprise: exploring Pacific Ocean organisms and several of the misrepresented taxa; promoting strong interactions amongst the MNPs research groups, and accordingly with other areas of knowledge; and having the productive sector participate in MNPs research.
Resumen Los productos naturales marinos (PNM) aislados de muestras recolectadas en Colombia han sido estudiados desde principios de los años 1980, mas esta información no está integrada, ni recopilada. Esta revisión sistemática describe los artículos publicados hasta diciembre de 2019. 173 artículos cumplieron los criterios de inclusión de enfoque en PNM obtenidos de especímenes recolectados en mares colombianos; trabajos originales escritos en inglés, portugués o español. La mayoría de los artículos fueron escritos por investigadores de grupos colombianos, con poca interacción entre ellos. El 99,4% de los artículos estudiaban muestras recolectadas del mar Caribe. Se estudiaron 183 especies, especialmente esponjas y octocorales. Se identificaron 1690 compuestos (238 nuevos), principalmente diterpenos y derivados de esteroles. En el 76,8% de los artículos se midió alguna actividad biológica, principalmente antibiótica (34%) y anticancerígena (30%). Los artículos se publicaron en 51 revistas (74,6% internacionales). En conclusión, la investigación sobre los PNM de origen colombiano ha crecido con el tiempo. Algunas oportunidades para abordar las lagunas encontradas comprenden: explorar los organismos del océano Pacífico y los taxa poco estudiados; promover interacciones entre los grupos de investigación de los PNM y de otras áreas del conocimiento; e involucrar al sector productivo en la investigación de los PMN.
Resumo Os Produtos Naturais Marinhos (PNMs) isolados de amostras coletadas na Colômbia têm sido objeto de estudo desde a década de 1980; porém, esta informação não está integrada nem compilada. Esta revisão sistemática descreve os artigos publicados em revistas científicas até dezembro de 2019. 173 artigos atenderam aos critérios de inclusão de foco em PNMs obtidos de espécimes coletados em mares colombianos; artigos originais escritos em inglês, português ou espanhol. A maioria dos autores dos artigos eram pesquisadores de grupos colombianos, com baixa interação entre eles. 99,4% dos artigos estudavam amostras coletadas no Mar do Caribe. Foram estudadas 183 espécies, especialmente esponjas e octocorais. Nesta revisão, identificaram-se 1690 compostos (238 novos), principalmente diterpenos e derivados de esterol. 76,8% dos artigos mediram algumas atividades biológicas, incluindo antibiótica (34%) e anticancerígena (30%). Os artigos analisados foram publicados em 51 periódicos (74,6% internacionais). Em conclusão, o trabalho científico sobre PNM de origem colombiana cresceu ao longo do tempo. As oportunidades mais relevantes para preencher as lacunas existentes incluem: explorar organismos do Oceano Pacífico e os taxa pouco estudados; promover interação entre os grupos de pesquisa de PNMs e com grupos de outras áreas do conhecimento; e envolver o setor produtivo na pesquisa de PNMs.
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Four new sesquiterpene quinone meroterpenoids, dysideanones F-G (1-2) and dysiherbols D-E (3-4), were isolated from the marine sponge Dysidea avara collected from the South China Sea. The new structures were elucidated by extensive analysis of spectroscopic data including HR-MS and 1D and 2D NMR spectra, and their absolute configurations were assigned by single-crystal X-ray diffraction and ECD calculations. Anti-inflammatory evaluation showed that dysiherbols D-E (3-4) exhibited moderate inhibitory activity on TNF-α-induced NF-κB activation in human HEK-293T cells with IC50 values of 10.2 and 8.6 μmol·L-1, respectively.
Subject(s)
Animals , Dysidea/chemistry , Porifera , Quinones/pharmacology , Sesquiterpenes/pharmacology , SkeletonABSTRACT
Objective: To study the chemical profile, antimicrobial properties, and synergistic effect with known antibiotics of essential oil extracted from the marine red macroalgae Centroceras clavulatum (C. Agardh) Montagne, collected in Morocco. Methods: The chemical composition of the oil was analyzed by gas chromatography-mass spectrometry. The oil was evaluated for antibacterial (Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, and Klebsiella pneumoniae), and antifungal activity (Candida albicans, Candida glabrata, Candida krusei, and Candida parapsilosis), by the disc diffusion method. The minimum inhibitory and minimum microbicidal concentrations of the oil were determined, as well as the synergistic effects of its application combined with the antibiotics ciprofloxacin and fluconazole, by the checkerboard method. Results: Thirty molecules were identified in the essential oil, comprising 96.27% of the total oil composition. Monoterpenes such as carvacrol (36.06%) were the most abundant compounds, followed by caryophyllene (14.67%), endo-borneol (9.04%), pyroterebic acid (3.23%) and caryophyllene oxide (3.13%). The oil exhibited a moderate antimicrobial activity with inhibition zone diameters ranging from 9.0 to 15.0 mm. The minimum inhibitory concentration values varied between 0.9 and 14.7 mg/mL, and Bacillus subtilis and Escherichia coli were the more sensitive bacteria with 0.9 and 1.9 mg/mL, respectively. The minimum microbicidal concentration values ranged from 0.4 to 14.7 mg/mL. A significant synergic action was observed when the oil was applied in combination with ciprofloxacin and fluconazole, with fractional inhibitory concentration index values ranging from 0.31 to 0.50. Synergy was found in 80% of the combinations and a 2 to 16-fold reduction of antibiotics MIC was observed. Conclusions: Our findings suggest that the essential oil of Centroceras clavulatum should be further appraised for its potential use in the management of multi-drug resistant microorganisms, with the purpose to restore the activity of standard antimicrobial drugs.
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Marine natural products (MNPs) are the source of modern marine drugs, but they have the characteristics of strong guiding function and weak druggability. How to quickly and efficiently discover new bioactive MNPs and optimize their druggability is an important idea for the research and development of innovative marine drugs. This article has made some discussions and suggestions on this emphasis from the origin and characteristics of MNPs, marine microorganisms with specific productivity for MNPs and the strategies of microbial MNPs with high yields and diverse structures, as well as the structural modification for medicinal use of MNPs.
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Marine sponges of the genus are well known as rich sources of diverse and complex biologically relevant natural products, including alkaloids, terpenoids, peptides, lipids, and steroids. Some of these metabolites, with novel structures and promising biological activities, have attracted a lot of attention from chemists seeking to perform their total synthesis in parallel to intensive biological studies towards new drug leads. In this review, we summarized the distribution of the chemically investigated sponges, the isolation, synthesis and biological activities of their secondary metabolites, covering the literature from 1982 to early 2018.
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Antecedentes: Los productos naturales aislados de microorganismos marinos han demostrado tener un amplio rango de actividades biológicas incluyendo inhibidores de quorum sensing. Objetivos: Estudiamos quince cepas bacterianas del phylum Firmicutes aisladas del coral blando Antillogorgia elisabethae que fueron evaluadas como una nueva fuente sostenible de compuestos inhibidores de quorum sensing (IQS). Métodos: Se prepararon cultivos en cuatro medios diferentes y extraídos usando una resina no iónica. Todos los extractos fueron probados con el fin de establecer su actividad inhibitoria de quorum sensing (IQS) usando Chromobacterium violaceum ATCC 31532 como biosensor. Los extractos activos fueron fraccionados mediante cartuchos RP-18. Cada fracción fue evaluada mediante bioensayo y analizada por HPLC. Resultados: Las fracciones metanólicas de Jeotgalicoccus halophilus y Oceanobacillus profundus fueron las más activas, lo cual sugiere que los compuestos no polares pueden ser los responsables de esta actividad. Conclusiones: El estudio químico del extracto orgánico de O. profundus cultivado en medio LBS permitió aislar los compuestos tirosol (1) y acetato de tirosol (2) como los responsables de la actividad IQS.
Background: Natural products isolated from marine microorganisms have demonstrated a wide range of biological activities included quorum sensing inhibitors. Objectives: We study fifteen marine Firmicutes bacterial strains isolated from the Caribbean soft coral Antillogorgia elisabethae that were evaluated as a novel and sustainable source of quorum sensing inhibitor compounds. Methods: Cultures were made in four different culture media and further extracted using a non-ionic resin. All these extracts were tested in order to establish its quorum sensing inhibition (QSI) activity using Chromobacterium violaceum ATCC 31532. The active extracts were fractionated by RP-18 cartridge. Each fraction was tested and evaluated for its composition by HPLC-PDA. Results: Methanol fractions of Jeotgalicoccus halophilus and Oceanobacillus profundus were the most active ones, suggesting that non-polar compounds could be the responsible for the QSI activity of the bacterial extracts here tested. Conclusions: The chemical study of the organic extract of Oceanobacillus profundus cultured in LBS, yielded the compounds tyrosol (1) and tyrosol acetate (2) as responsible of QSI activity showed by the organic extract.
Subject(s)
Humans , Bacteria , Quorum Sensing , Biological Products , Marine EnvironmentABSTRACT
Abstract Four bisabolanes 1–4, including perezone (1) and triacetyl perezone (2), were isolated through a bioassay-guided fractionation of the extract obtained from the Caribbean gorgonian coral Pseudopterogorgia rigida collected during an expedition cruise to the Bahamas. All isolated compounds showed to be cytotoxic toward panel of four human tumor cell lines, as quantified by the MTT assay after 72 h incubation. Perezone (1), the most active one, was further analyzed, showing to be cytotoxic, but not selective, in a 12-cell line panel comprising tumor and non-tumor, as well as human and murine cells. Additionally, 1 was assayed for cytotoxicity against HL-60 leukemic cells. Pre-treatment with an acute free radical scavenger (L-NAC) before exposure of cells to perezone virtually eliminated the generation of intracellular ROS and lessened its severe cytotoxicity. The protective effect delivered by L-NAC evidences that the mechanism of perezone-induced cytotoxicity is partially associated to production of ROS and a consequent induction of oxidative stress.
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Abstract Biofilm has a primary role in the pathogenesis of diseases and in the attachment of multicellular organisms to a fouled surface. Because of that, the control of bacterial biofilms has been identified as an important target. In the present study, five lipid compounds isolated from soft coral Eunicea sp. and three terpenoids together with a mixture of sterols from Eunicea fusca collected at the Colombian Caribbean Sea showed different effectiveness against biofilm formation by three marine bacteria associated with immersed fouled surfaces, Ochrobactrum pseudogringnonense,Alteromona macleodii and Vibrio harveyi, and against two known biofilm forming bacteria, Pseudomonas aeruginosa ATCC 27853 and Staphylococcus aureus ATCC 25923. The pure compounds were characterized by NMR, HRESI-MS, HRGC-MS and optical rotation. The most effective compounds were batyl alcohol (1) and fuscoside E peracetate (6), acting against four strains without affecting their microbial growth. Compound 1 showed biofilm inhibition greater than 30% against A. macleodii, and up to 60% against O. pseudogringnonense,V. harveyi and S. aureus. Compound 6 inhibited O. pseudogringnonense and V. harveyi between 25 and 50%, and P. aeruginosa or S. aureus up to 60% at 0.5 mg/ml. The results suggest that these compounds exhibit specific biofilm inhibition with lower antimicrobial effect against the bacterial species assayed.
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Abstract Sponges of the genus Aplysina are among the most common benthic animals on reefs of the Caribbean, and display a wide diversity of morphologies and colors. Tissues of these sponges lack mineralized skeletal elements, but contain a dense spongin skeleton and an elaborate series of tyrosine-derived brominated alkaloid metabolites that function as chemical defenses against predatory fishes, but do not deter some molluscs. Among the earliest marine natural products to be isolated and identified, these metabolites remain the subject of intense interest for commercial applications because of their activities in various bioassays. In this study, crude organic extracts from 253 sponges from ten morphotypes among the species Aplysina archeri,Aplysina bathyphila,Aplysina cauliformis,Aplysina fistularis,Aplysina fulva,A. insularis, and Aplysina lacunosa were analyzed by liquid chromatography–mass spectrometry (LC–MS) to characterize the pattern of intra- and interspecific variabilities of the twelve major secondary metabolites present therein. Patterns across Aplysina species ranged from the presence of mostly a single compound, fistularin-3, in A. cauliformis, to a mixture of metabolites present in the other species. These patterns did not support the biotransformation hypothesis for conversion of large molecular weight molecules to smaller ones for the purpose of enhanced defense. Discriminant analyses of the metabolite data revealed strong taxonomic patterns that support a close relationship between A. fistularis,A. fulva and A. insularis, while two morphotypes of A. cauliformis (lilac creeping vs. brown erect) were very distinct. Two morphotypes of A. lacunosa, one with hard tissue consistency, the other soft and thought to belong to a separate genus (Suberea), had very similar chemical profiles. Of the twelve metabolites found among samples, variation in fistularin-3, dideoxyfistularin-3 and hydroxyaerothionin provided the most predictive influence in decreasing order. Except for one morphotype, weak relationships were found from within-morphotype analyses of metabolite concentrations as a function of geographic location (Florida, N Bahamas, S Bahamas) and depth (<10 m, 10–20 m, >20 m). Our data suggest that metabolite profiles are strongly influenced by sponge phenotype rather than by the diverse microbiome which many Aplysina species share.
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Abstract The occurrence of (−)-phototridachiahydropyrone (5) in nature has been proven. This compound has been now identified as minor component of the extract of marine sacoglossan mollusk Elysia crispata from which the main (−)-tridachiahydropyrone (4) was previously described. Synthetic (±)-5 was formerly obtained by Moses’ group by biomimetic photochemical conversion of (±)-tridachiahydropyrone (4). The same authors suggested that compound 5 had to be a natural product derived from precursor 4 “yet to be discovered”. Comparison of CD profiles of natural (−)-4 and (−)-5 indicated the same absolute configuration for both compounds. This evidence is in agreement with the concerted mechanism proposed for the photochemical conversion.
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During the structural elucidation of natural products, one of the key steps is attributed to the solution of configuration including chiral carbons, axial and planar asymmetry. Stereogenic assignment is an essential work involved in natural product chemistry, while identification of stereogenic centers may be helpful to recognize the structure related to target function. Modern spectroscopic technology provided a reliable tool for the configurational assignment. In this paper, we intend to summarize part of our work regarding the application of extensive spectroscopic methods for the determination of the absolute configurations of marine-derived natural products.
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Marine natural products are a significant and important source for new small molecule drug leads. In most cases, marine natural products have unique structure skeletons and stereo complexity. Their absolute configurations and biologically activities are closely related, which highlights the importance of absolute configurational assignment. The stereo-configurational evaluation of marine natural products is one of the most difficulties in determining natural structure, and also very important contents of natural products research. In this review we summarized a variety of cases with different structural types that often dictate some valuable approach to configurational assignment. Hopefully, the selected case studies could provide some inspiration to a readership with broad interests: natural products chemists and synthetic organic chemists.
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In the present investigation we report the antibacterial activity of halistanol sulfate A isolated from the sponge Petromica ciocalyptoides, as well as of rodriguesines A and B isolated from the ascidian Didemnum sp., against the caries etiologic agent Streptococcus mutans. The transcription levels of S. mutans virulence genes gtfB, gtfC and gbpB, as well as of housekeeping genes groEL and 16S, were evaluated by sqRT-PCR analysis of S. mutans planktonic cells. There were no alterations in the expression levels of groEL and 16S after antimicrobial treatment with halistanol sulfate A and with rodriguesines A and B, but the expression of the genes gtfB, gtfC and gbpB was down-regulated. Halistanol sulfate A displayed the most potent antimicrobial effect against S. mutans, with inhibition of biofilm formation and reduction of biofilm-associated gene expression in planktonic cells. Halistanol sulfate A also inhibited the initial oral bacteria colonizers, such as Streptococcus sanguinis, but at much higher concentrations. The results obtained indicate that halistanol sulfate A may be considered a potential scaffold for drug development in Streptococcus mutans antibiofilm therapy, the main etiologic agent of human dental caries. .
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This review explores the chemical and biological aspects/results reported in the literature of the octocoral species collected at the Brazilian Coast. This article summarizes the biological activities (including pharmacological, antifouling and others related to chemical ecology) for the compounds and/or extracts described elsewhere. Data and references of compounds isolated from species belonging to the same genus, which have not been investigated in Brazil yet, are presented, emphasizing the importance for research in this area.
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Studying on marine natural products is a vibrant research area in the world. Due to their prevention and treatment effects on malignant tumor, cardiovascular disease and other major human diseases, marine natural products have become an important guidance to find the primary drugs. Recently, beneficial effects of marine natural products on treatment of metabolic syndrome related diseases have been intensively explored. Therefore, numbers of novel active products were found out and new mechanisms were revealed. This article reviews the research literature published after 2010 and summarizes the effects of marine natural products in metabolic syndrome related diseases, such as central obesity, insulin resistance, hyperlipidemia, hypertension and inflammation.
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Studying on marine natural products is a vibrant research area in the world. Due to their prevention and treatment effects on malignant tumor,cardiovascular disease and other major human diseases,marine natural products have become an important guidance to find the primary drugs. Recently,beneficial effects of marine natural products on treatment of metabolic syndrome related diseases have been intensively explored. Therefore,numbers of novel active products were found out and new mechanisms were revealed. This article reviews the research literature published after 2010 and summarizes the effects of marine natural products in metabolic syndrome related diseases,such as central obesity,insulin resistance,hyperlipidemia,hypertension and inflammation.
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Organic extracts of 36 species of marine algae (sixteen species of Rhodophyta, eight species of Ochrophyta and twelve species of Chlorophyta) from seven locations on the Brazilian coast were evaluated for their anti-HSV-1 and anti-HSV-2 activity resistant to Acyclovir (ACV). Activity tests in crude extracts, followed by the identification of the major compounds present, were performed for all species. The chemical profiles of all crude extracts were obtained by ¹H-NMR and 13C-NMR spectroscopy. The percentage of extracts with antiviral activity was higher for HSV-1 (86.1%) than for HSV-2 (55.5%). The green algae Ulva fasciata and Codium decorticatum both showed the highest activity (99.9%) against HSV-1, with triacylglycerols and fatty acids as the major components. The red alga Laurencia dendroidea showed good activity against HSV-1 (97.5%) and the halogenated sesquiterpenes obtusol and (-)-elatol were identified as the major components in the extract. Against HSV-2, the green alga Penicillus capitatus (Chlorophyta) and Stypopodium zonale (Ochrophyta) were the most active (96.0 and 95.8%). Atomaric acid, a meroditerpene, was identified as the major secondary metabolite in the S. zonale extract. These results reinforce the role of seaweeds as important sources of compounds with the potential to enter into the pipeline for development of new drugs against herpes simplex.
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Seaweeds are potential sources of high biotechnological interest due to production of a great diversity of compounds exhibiting a broad spectrum of biological activities. On the other hand, there is an urgent need for management options for a sustainable approach to the use of marine organisms as a source of bioactive compounds. This review discusses the bioprospection for bioactive seaweed compounds as pharmaceuticals and antifouling agents, encompassing their potential and possible obstacles and alternatives. In spite of their potential, research on pharmaceuticals and antifouling agents from seaweeds includes mainly the search for molecules that exhibit these biological activities, but lacks of consideration of fundamental and limiting aspects such as the development of alternatives to sustainable supply. However, for the complete development of pharmaceuticals and antifouling compounds in Brazil, marine bioprospection should be more comprehensive, associating the search for molecules with an analysis of their supply. In this way, it is possible to promote sustainable development and conservation of biodiversity, as well as to assert the economic development of Brazil.
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Marine natural products have currently been recognized as the most promising source of bioactive substances for drug discovery research. In this review, extraordinary metabolites from marine algae species are illustrated, as well as approaches for their isolation and determination of their biological properties and pharmaceutical potential. Furthermore, marine endophytic microorganisms (from marine algae) are presented as a new subject for extensive investigation to find novel natural products, which make them a potentially rich and innovative source for new drug candidates.
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The marine environment is a rich source of biologically active compounds with pharmacological properties. Marine organisms often produce secondary metabolites with structural features different from those produced by terrestrial ones, and the Phylum Porifera seems to be one of the most productive in this sense. This study was undertaken to provide data on mutagenic and antimutagenic activities from an acetone (Areac) and an ethanol (Areet) extract obtained from Arenosclera brasiliensis, an endemic Brazilian sponge. A qualitative Salmonella reverse mutation test was performed with the TA97, TA98, TA100, and TA102 strains by incubating cells with Areac and Areet in the presence and absence of a known mutagen. A cytotoxic evaluation of the extracts was also performed. A. brasiliensis did not display any mutagenic activity, but Areac showed significant toxicity against test strains. In the antimutagenic assay, a reduction in the number of his+ revertants was observed for the TA97, TA100 and TA102 strains treated with Areac when compared to the positive controls. Areet treatment showed protective activity against DNA lesions only for the TA100. These results are in agreement with those obtained previously with other A. brasiliensis extracts, suggesting an antimutagenic activity.