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1.
Zootaxa ; 5031(1): 1-112, 2021 Sep 03.
Artigo em Inglês | MEDLINE | ID: mdl-34811146

RESUMO

Until now, 127 species of marine sponges have been recorded in the southern Gulf of Mexico (SGoM). In this study, we describe the sponge fauna recorded on 16 coral reefs of the SGoM, defined as the Mexican waters of the Gulf of Mexico (GoM), during a period from 2005 to 2019. We report 80 sponge species, including 34 first geographic records for the southern GoM region. The latter are fully described and illustrated, taking into account 24 that represent new records for the GoM: Agelas conifera, Agelas sventres, Agelas wiedenmayeri, Prosuberites carriebowensis, Desmanthus meandroides, Cliona aprica, Cliona dioryssa, Placospongia ruetzleri, Haliclona (Gellius) megasclera, Haliclona (Reniera) aff. portroyalensis, Neopetrosia proxima, Xestospongia arenosa, Calyx podatypa, Shiphonodictyon xamaycaense, Acarnus innominatus, Iotrochota arenosa, Polymastia tenax, Svenzea cristinae, Svenzea flava, Svenzea tubulosa, Svenzea zeai, Timea stenosclera, Stellettinopsis megastylifera, Suberea flavolivescens. The present work highlights the understimated and remarkable diversity of reef-associated sponges within the Campeche Bank Coral reef systems. Present work data was compiled with existing published information to produce an updated list of 161 known sponges in the southern GoM.


Assuntos
Agelas , Haliclona , Animais , Recifes de Corais , Golfo do México
2.
Mycopathologia ; 186(6): 819-832, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34564785

RESUMO

This study aimed to determine the antifungal and antibiofilm activities of Agelas dispar on biofilm-producing Candida species. The methanolic extract of A. dispar was obtained and the fraction Ag2 showed inhibitory activity for all 13 Candida strains tested, in concentrations ranging from 2.5 to 0.15625 mg/mL. Antifungal activity of fungicidal nature was seen between 5.0 and 0.3125 mg/mL of extract against the strains. All the strains were classified as biofilm producers. The methanolic extract Ag2 was tested at concentrations of 2.5 and 1.25 mg/mL for antibiofilm activity against the biofilm formation and maturation in all the strains of the genus Candida. Treated and untreated biofilm samples were selected for visualization using scanning electron microscopy (SEM). SEM allowed the visualization of the quantitative decrease in the microbial community, alterations of structural morphology, and destruction of both the formation and maturation of biofilms, at the cellular level. The mechanism of action of this fraction is suggested to be at the plasma membrane and/or cell wall alteration level. Therefore, the use of the methanolic extract of A. dispar may be a promising antifungal and antibiofilm therapeutic strategy against different species of the genus Candida.


Assuntos
Agelas , Poríferos , Animais , Antifúngicos/farmacologia , Biofilmes , Candida , Candida albicans , Testes de Sensibilidade Microbiana , Extratos Vegetais/farmacologia
3.
PLoS One ; 15(12): e0244095, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33382741

RESUMO

Fluorescent natural compounds have been identified in several marine hosts of microalgae. Their prevalence, and the energy the host is expending on their synthesis, suggests an important, yet poorly understood ecological role. It has been suggested that some of these natural products may enhance the photosynthesis of microbial symbionts. In this study, the effect of Ageladine A (Ag A), a pH-dependent fluorophore found in sponges of the genus Agelas, on the photosynthesis of nine microalgal species and strains was examined. The data showed that the variety of effects of Ag A additions differed between species, and even strains within a species. While in one strain of Synechococcus sp., the presence of Ag A increased gross photosynthesis under UV light exposure, it decreased in another. And while in the chlorophyte T. chuii overall metabolic activity was greatly reduced under all forms of lighting, photosynthesis in T. lutea was positively affected by the addition of Ag A. The variety of effects of Ag A on photosynthesis observed in this study indicate a complex interaction of Ag A with microalgal cells and suggests that a host may be able to shape its own symbiotic microbiome with self-produced natural products.


Assuntos
Agelas/microbiologia , Microalgas/fisiologia , Fotossíntese/efeitos dos fármacos , Pirróis/farmacologia , Simbiose/fisiologia , Animais , Microalgas/classificação , Pirróis/metabolismo , Simbiose/efeitos dos fármacos
4.
PLoS One ; 15(11): e0242464, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33211752

RESUMO

In several marine hosts of microalgae, fluorescent natural products may play an important role. While the ecological function of these compounds is not well understood, an interaction of these molecules with the photosynthesis of the symbionts has been suggested. In this study, the effect of Ageladine A (Ag A), a pH-dependent fluorophore found in sponges of the genus Agelas, on microalgal fluorescence was examined. The spectra showed an accumulation of Ag A within the cells, but with variable impacts on fluorescence. While in two Synechococcus strains, fluorescence of phycoerythrin increased significantly, the fluorescence of other Synechococcus strains was not affected. In four out of the five eukaryote species examined, chlorophyll a (Chl a) fluorescence intensity was modulated. In Tisochrysis lutea, for example, the position of the fluorescence emission maximum of Chl a was shifted. The variety of these effects of Ag A on microalgal fluorescence suggests that fluorophores derived from animals could play a crucial role in shaping the composition of marine host/symbiont systems.


Assuntos
Agelas/química , Microalgas/efeitos dos fármacos , Pirróis/farmacologia , Simbiose , Animais , Clorofila A/química , Fluorescência , Micrasterias/efeitos dos fármacos , Micrasterias/metabolismo , Microalgas/metabolismo , Fotossíntese/efeitos dos fármacos , Fotossíntese/efeitos da radiação , Ficobilissomas/química , Ficobilissomas/efeitos dos fármacos , Ficoeritrina/química , Pigmentos Biológicos/química , Pirróis/isolamento & purificação , Especificidade da Espécie , Espectrometria de Fluorescência , Synechococcus/efeitos dos fármacos , Synechococcus/metabolismo , Raios Ultravioleta
5.
Mar Drugs ; 18(10)2020 Sep 29.
Artigo em Inglês | MEDLINE | ID: mdl-33003597

RESUMO

Radiation therapy (RT) is an effective local treatment for unresectable hepatocellular carcinoma (HCC), but there are currently no predictive biomarkers to guide treatment decision for RT or adjuvant systemic drugs to be combined with RT for HCC patients. Previously, we reported that extracts of the marine sponge Agelas sp. may contain a natural radiosensitizer for HCC treatment. In this study, we isolated (-)-agelamide D from Agelas extract and investigated the mechanism underlying its radiosensitization. (-)-Agelamide D enhanced radiation sensitivity of Hep3B cells with decreased clonogenic survival and increased apoptotic cell death. Furthermore, (-)-agelamide D increased the expression of protein kinase RNA-like endoplasmic reticulum kinase/inositol-requiring enzyme 1α/activating transcription factor 4 (PERK/eIF2α/ATF4), a key pathway of the unfolded protein response (UPR) in multiple HCC cell lines, and augmented radiation-induced UPR signaling. In vivo xenograft experiments confirmed that (-)-agelamide D enhanced tumor growth inhibition by radiation without systemic toxicity. Immunohistochemistry results showed that (-)-agelamide D further increased radiation-induced ATF4 expression and apoptotic cell death, which was consistent with our in vitro finding. Collectively, our results provide preclinical evidence that the use of UPR inducers such as (-)-agelamide D may enhance the efficacy of RT in HCC management.


Assuntos
Carcinoma Hepatocelular/radioterapia , Alcaloides Diterpenos/farmacologia , Neoplasias Hepáticas/radioterapia , Radiossensibilizantes/farmacologia , Agelas/química , Animais , Linhagem Celular Tumoral , Alcaloides Diterpenos/isolamento & purificação , Humanos , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Radiossensibilizantes/isolamento & purificação , Resposta a Proteínas não Dobradas , Ensaios Antitumorais Modelo de Xenoenxerto
6.
Mar Drugs ; 18(9)2020 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-32872586

RESUMO

Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5). Their structures were elucidated on the basis of spectroscopic analyses. Agesasines A (1) and B (2) were assigned as rare bromopyrrole alkaloids lacking an aminoimidazole moiety, while 3-5 were elucidated to be linear bromopyrrole alkaloids with either aminoimidazolone, aminoimidazole, or N-methylated aminoimidazole moieties.


Assuntos
Agelas/química , Alcaloides/isolamento & purificação , Células A549 , Alcaloides/química , Alcaloides/farmacologia , Animais , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células HeLa , Humanos , Células MCF-7 , Estrutura Molecular , Neoplasias/tratamento farmacológico , Neoplasias/patologia
7.
Mar Drugs ; 18(6)2020 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-32585891

RESUMO

The pyrrole-imidazoles, a group of alkaloids commonly found in marine sponges belonging to the genus Agelas, display a wide range of biological activities. Herein, we report the first chemical study of the secondary metabolites of the sponge A. dilatata from the coastal area of the Yucatan Peninsula (Mexico). In this study, we isolated eight known alkaloids from an organic extract of the sponge. We used NMR and MS analysis and comparison with existing databases to characterize the alkaloids: ageliferin (1), bromoageliferin (2), dibromoageliferin (3), sceptrin (4), nakamuric acid (5), 4-bromo-1H-pyrrole-2-carboxylic acid (6), 4,5-dibromopyrrole-2-carboxylic acid (7) and 3,7-dimethylisoguanine (8). We also evaluated, for the first time, the activity of these alkaloids against the most problematic multidrug-resistant (MDR) pathogens, i.e., the Gram-negative bacteria Pseudomonas aeruginosa, Klebsiella pneumoniae and Acinetobacter baumannii. Bromoageliferin (2) displayed significant activity against P. aeruginosa. Comparison of the antibacterial activity of ageliferins 1-3 (of similar structure) against P. aeruginosa revealed some relationship between structure and activity. Furthermore, in in vitro assays, 2 inhibited growth and biofilm production in clinical strains of P. aeruginosa. Moreover, 2 increased the survival time in an in vivo Galleria mellonella model of infection. The findings confirm bromoageliferin (2) as a potential lead for designing new antibacterial drugs.


Assuntos
Alcaloides/farmacologia , Antibacterianos/farmacologia , Poríferos/química , Pseudomonas aeruginosa/efeitos dos fármacos , Acinetobacter baumannii/efeitos dos fármacos , Acinetobacter baumannii/crescimento & desenvolvimento , Agelas/química , Alcaloides/isolamento & purificação , Animais , Biofilmes , Klebsiella pneumoniae/efeitos dos fármacos , Klebsiella pneumoniae/crescimento & desenvolvimento , México , Estrutura Molecular , Pseudomonas aeruginosa/crescimento & desenvolvimento
8.
J Nat Prod ; 83(2): 374-384, 2020 02 28.
Artigo em Inglês | MEDLINE | ID: mdl-32072810

RESUMO

Chemical investigation of the Mediterranean Sea sponge, Agelas oroides, collected off the Tel Aviv coast, yielded eight new bromopyrrole metabolites, agesamine C (1), dioroidamide A (2), slagenin D (3), (-)-monobromoagelaspongin (4), (-)-11-deoxymonobromoagelaspongin (5), (-)-11-O-methylmonobromoagelaspongin (6), E-dispacamide (7), and pyrrolosine (8), along with 18 known bromopyrrole alkaloids and a known bromotyrosine derivative. The structures of the new metabolites were elucidated by analysis of the spectroscopic and spectrometric data, including 1D and 2D NMR, ECD, and high-resolution mass spectrometry. The sponge extract exhibited antimicrobial activity against pathogenic and environmental bacteria, and quorum sensing inhibitory activity (QSI) against Chromobacterium violaceum. QSI guided separation of the extract established oroidin, benzosceptrin C, and 4,5-dibromopyrrole-2-carboxamide as the active components. The latter compounds were tested for inhibition of growth and biofilm formation in Pseudomonas aeruginosa PAO1. The most active and available compound, oroidin, was assayed for inhibition of growth and biofilm formation in bacteria that were isolated from the sponge and its environment.


Assuntos
Agelas/química , Alcaloides/química , Antibacterianos/química , Imidazóis/química , Pirróis/química , Animais , Antibacterianos/farmacologia , Chromobacterium , Mar Mediterrâneo , Pseudomonas aeruginosa/efeitos dos fármacos , Percepção de Quorum/efeitos dos fármacos
9.
Org Lett ; 21(23): 9483-9486, 2019 12 06.
Artigo em Inglês | MEDLINE | ID: mdl-31746608

RESUMO

One new dimeric bromopyrrole alkaloid, agelanemoechine, with an unprecedented imidazo [1,5-a] azepin nucleus together with one known dimeric bromopyrrole alkaloid sceptrin were isolated from the marine sponge Agelas nemoechinata. The structure elucidation and absolute configuration assignments were determined by extensive spectroscopic analyses and the comparison of experimental and calculated ECD. Agelanemoechine showed strong pro-angiogenic activity in zebrafish.


Assuntos
Agelas , Alcaloides/química , Alcaloides/farmacologia , Indutores da Angiogênese/química , Indutores da Angiogênese/farmacologia , Pirróis/química , Pirróis/farmacologia , Animais , Animais Geneticamente Modificados , China , Estrutura Molecular , Oceanos e Mares , Ftalazinas/farmacologia , Inibidores de Proteínas Quinases/farmacologia , Piridinas/farmacologia , Receptores de Fatores de Crescimento do Endotélio Vascular/antagonistas & inibidores , Peixe-Zebra
10.
Mar Drugs ; 17(10)2019 Oct 11.
Artigo em Inglês | MEDLINE | ID: mdl-31614540

RESUMO

Sponge-associated bacteria have been mostly cultured from shallow water (≤30 m) sponges, whereas only few studies targeted specimens from below 30 m. This study assessed the cultivability of bacteria from two marine sponges Xestospongia muta and Agelas sventres collected from shallow (<30 m), upper mesophotic (30-60 m), and lower mesophotic (60-90 m) reefs. Sponge-associated bacteria were cultivated on six different media, and replicate plates were used to pick individual colonies or to recover the entire biomass. Prokaryotic community analysis was conducted using Illumina MiSeq sequencing of 16S rRNA gene amplicons. A total of 144 bacterial isolates were picked following a colony morphology coding scheme and subsequently identified by 16S rRNA gene sequence analysis. Sponge individuals at each depth-range harboured specific cultivable bacteria that were not retrieved from specimens collected at other depths. However, there were substantial differences in the number of colonies obtained for replicate sponges of the same species. In addition, source of inoculum and cultivation medium had more impact on the cultured prokaryotic community than sample collection depth. This suggests that the "plate count anomaly" is larger than differences in sponge-associated prokaryotic community composition related to depth.


Assuntos
Agelas/microbiologia , Bactérias/crescimento & desenvolvimento , Poríferos/microbiologia , Água do Mar/microbiologia , Xestospongia/microbiologia , Animais , Bactérias/genética , Biodiversidade , Biomassa , Filogenia , RNA Ribossômico 16S/genética , Análise de Sequência de DNA/métodos
11.
Mar Drugs ; 16(12)2018 Dec 17.
Artigo em Inglês | MEDLINE | ID: mdl-30563015

RESUMO

Two new sceptrin derivatives (1,2) and eight structurally-related known bromopyrrole-bearing alkaloids were isolated from the tropical sponge Agelas kosrae. By a combination of spectroscopic methods, the new compounds, designated dioxysceptrin (1) and ageleste C (2), were determined to be structural analogs of each other that differ at the imidazole moiety. Dioxysceptrin was also found to exist as a mixture of α-amido epimers. The sceptrin alkaloids exhibited weak cytotoxicity against cancer cells. Compounds 1 and 2 also moderately exhibited anti-angiogenic and isocitrate lyase-inhibitory activities, respectively.


Assuntos
Agelas/química , Alcaloides/farmacologia , Produtos Biológicos/farmacologia , Pirróis/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Inibidores da Angiogênese/química , Inibidores da Angiogênese/isolamento & purificação , Inibidores da Angiogênese/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Produtos Biológicos/isolamento & purificação , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Ensaios Enzimáticos , Células Endoteliais da Veia Umbilical Humana , Humanos , Isocitrato Liase/antagonistas & inibidores , Pirróis/química , Pirróis/isolamento & purificação , Estereoisomerismo
12.
Sci Rep ; 8(1): 6317, 2018 04 20.
Artigo em Inglês | MEDLINE | ID: mdl-29679028

RESUMO

Although radiation therapy is an effective treatment modality in many cancers, there is an urgent need to develop therapeutic drugs capable of overcoming radioresistance or minimizing normal tissue toxicity. A wide variety of marine-derived bioactive compounds have been screened for anti-cancer drug discovery, but little is known regarding radiation therapy applications. In this study, six different extracts of marine sponges collected from the Micronesian sea were screened for anti-cancer and radiosensitizing activity. Two extracts derived from Agelas sponges collected off the coast of Kosrae and Chuuk, the Federated States of Micronesia significantly decreased clonogenic survival of hepatocellular carcinoma (HCC) cells after exposure to ionizing radiation (IR). The Agelas extracts augmented IR-induced apoptosis and accumulation of reactive oxygen species (ROS). Endoplasmic reticulum (ER) stress was increased via unfolded protein response stimulation, which induced autophagy. N-acetylcysteine, a ROS scavenger, diminished ER stress and autophagy induction effects. This result indicated that Agelas extracts may sensitize HCC cells to IR via ROS overproduction in vitro. Our findings suggest that the Agelas sp. may have potential utility in radiosensitizer development.


Assuntos
Carcinoma Hepatocelular/tratamento farmacológico , Linhagem Celular Tumoral/efeitos dos fármacos , Radiossensibilizantes/farmacologia , Acetilcisteína/metabolismo , Agelas/metabolismo , Animais , Apoptose/efeitos dos fármacos , Autofagia/efeitos dos fármacos , Carcinoma Hepatocelular/patologia , Extratos Celulares/farmacologia , Estresse do Retículo Endoplasmático/efeitos dos fármacos , Humanos , Neoplasias Hepáticas/tratamento farmacológico , Micronésia , Poríferos/metabolismo , Espécies Reativas de Oxigênio/metabolismo
13.
Microb Ecol ; 76(2): 459-466, 2018 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-29299617

RESUMO

The brown tube sponge Agelas tubulata (cf. Agelas conifera) is an abundant and long-lived sponge on Caribbean reefs. Recently, a disease-like condition, Agelas wasting syndrome (AWS), was described from A. tubulata in the Florida Keys, where prevalence of the syndrome increased from 7 to 35% of the sponge population between 2010 and 2015. In this study, we characterized the prokaryotic symbiont community of A. tubulata for the first time from individuals collected within the same monitoring plots where AWS was described. We also sampled tissue from A. tubulata exhibiting symptoms of AWS to determine its effect on the diversity and structure of prokaryotic symbiont communities. Bacteria from the phyla Chloroflexi and Proteobacteria, particularly the class Gammaproteobacteria, dominated the sponge microbiome in tissue samples of both healthy sponges and those exhibiting AWS. Prokaryotic community structure differed significantly between the diseased and healthy sponge samples, with greater variability among communities in diseased samples compared to healthy samples. These differences in prokaryotic community structure included a shift in relative abundance of the dominant, ammonia-oxidizing (Thaumarchaeota) symbionts present in diseased and healthy sponge samples. Further research is required to determine the functional consequences of this shift in microbial community structure and the causal relationship of dysbiosis and sponge disease in A. tubulata.


Assuntos
Agelas/microbiologia , Doenças dos Animais/microbiologia , Disbiose , Células Procarióticas/fisiologia , Simbiose , Síndrome de Emaciação/microbiologia , Animais , Archaea/classificação , Archaea/fisiologia , Bactérias/classificação , Fenômenos Fisiológicos Bacterianos , Caquexia , Região do Caribe , Chloroflexi/fisiologia , Florida , Gammaproteobacteria/fisiologia , Microbiota , Filogenia , Poríferos/microbiologia , Proteobactérias/fisiologia , Água do Mar/microbiologia , Síndrome de Emaciação/epidemiologia
14.
J Nat Med ; 72(1): 364-368, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29198066

RESUMO

Two new diterpene alkaloids having an N-methyladenine moiety, agelamasines A (1) and B (2), were isolated from an Okinawan marine sponge Agelas sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analyses. Agelamasine A (1) is the first diterpene alkaloid with a rearranged (4 â†’ 2)-abeo-clerodane skeleton from a marine source, while agelamasine B (2) is a clerodane diterpene alkaloid.


Assuntos
Agelas/química , Alcaloides/isolamento & purificação , Diterpenos/isolamento & purificação , Alcaloides/química , Animais , Diterpenos/química , Japão , Conformação Molecular
15.
Mar Drugs ; 15(11)2017 Nov 08.
Artigo em Inglês | MEDLINE | ID: mdl-29117128

RESUMO

The marine sponge genus Agelas comprises a rich reservoir of species and natural products with diverse chemical structures and biological properties with potential application in new drug development. This review for the first time summarized secondary metabolites from Agelas sponges discovered in the past 47 years together with their bioactive effects.


Assuntos
Agelas/metabolismo , Produtos Biológicos/metabolismo , Agelas/química , Animais , Organismos Aquáticos , Produtos Biológicos/química
16.
Bioorg Med Chem Lett ; 27(10): 2207-2209, 2017 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-28389151

RESUMO

Agelasine G (1), a known bromine-containing diterpene alkaloid, was isolated as a new type of protein tyrosine phosphatase (PTP) 1B inhibitor together with ageline B (2), an inactive debromo-derivative of 1, from the marine sponge Agelas nakamurai collected at Iriomote Island in Okinawa, Japan. Further biological evaluations revealed that compound 1 exhibited selective inhibitory activity against PTP1B over T-cell PTP and CD45 phosphatase. Compound 1 also enhanced the insulin-stimulated phosphorylation levels of Akt in Huh-7 cells more strongly than compound 2. The results obtained in this study suggest that compound 1 activates the insulin signaling pathway by inhibiting PTP1B activity.


Assuntos
Agelas/química , Alcaloides/química , Diterpenos/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Agelas/metabolismo , Alcaloides/isolamento & purificação , Alcaloides/toxicidade , Animais , Carcinoma Hepatocelular/metabolismo , Carcinoma Hepatocelular/patologia , Linhagem Celular Tumoral , Diterpenos/isolamento & purificação , Diterpenos/toxicidade , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/toxicidade , Humanos , Insulina/metabolismo , Japão , Neoplasias Hepáticas/metabolismo , Neoplasias Hepáticas/patologia , Fosforilação/efeitos dos fármacos , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Pirróis/química , Transdução de Sinais/efeitos dos fármacos
17.
J Nat Med ; 71(3): 531-536, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28364227

RESUMO

In the course of our studies on anti-mycobacterial substances from marine organisms, the known dimeric sphingolipid, leucettamol A (1), was isolated as an active component, together with the new bromopyrrole alkaloid, 5-bromophakelline (2), and twelve known congeners from the Indonesian marine sponge Agelas sp. The structure of 2 was elucidated based on its spectroscopic data. Compound 1 and its bis TFA salt showed inhibition zones of 12 and 7 mm against Mycobacterium smegmatis at 50 µg/disk, respectively, while the N,N'-diacetyl derivative (1a) was not active at 50 µg/disk. Therefore, free amino groups are important for anti-mycobacterial activity. This is the first study to show the anti-mycobacterial activity of a bisfunctionalized sphingolipid. Compound 13 exhibited weak PTP1B inhibitory activity (29% inhibition at 35 µM).


Assuntos
Agelas/química , Antibacterianos/farmacologia , Mycobacterium smegmatis/efeitos dos fármacos , Pirróis/isolamento & purificação , Esfingolipídeos/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Indonésia , Estrutura Molecular , Mycobacterium smegmatis/crescimento & desenvolvimento , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Pirróis/química , Pirróis/farmacologia , Esfingolipídeos/química , Esfingolipídeos/isolamento & purificação , Relação Estrutura-Atividade
18.
Nat Prod Res ; 31(14): 1625-1632, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28278683

RESUMO

The Mediterranean marine sponge Agelas oroides is known to contain a large quantity of oroidin, a deterrent, antifouling and antibiofilm pyrrole-2-aminoimidazole. In contrast with other tropical specimens, the chemical composition of Mediterranean Agelas oroides is surprisingly relatively poor in other related metabolites. In the course of finding novel marine natural products, LC-MS based metabolomics study of the Mediterranean Agelas oroides, however, revealed that next to the major compound oroidin, the sponge contains in fact a great diversity of known pyrrole-imidazole alkaloids in minute amounts. Here, we describe identification of 13 known oroidin class alkaloids along with one new monobromoagelaspongin (24). Five betaines and one amine were also identified from the aqueous fraction. One of those compounds (-)-equinobetaine B (30) was found to be an enantiomer of the known natural product (+)-equinobetaine B.


Assuntos
Agelas/química , Metabolômica/métodos , Poríferos/química , Alcaloides/análise , Alcaloides/química , Animais , Produtos Biológicos/análise , Imidazóis/análise , Pirróis/análise
19.
Chem Biodivers ; 14(7)2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28222487

RESUMO

Two pairs of new non-brominated racematic pyrrole derivatives, (±)-nakamurine D (1) and (±)-nakamurine E (2), two new diterpene alkaloids, isoagelasine C (16) and isoagelasidine B (21), together with 13 known pyrrole derivatives ((±)-3 - 15), five known diterpene alkaloids (17 - 20, 22) were isolated from the South China Sea sponge Agelas nakamurai. The racemic mixtures, compounds 1 - 4, were resolved into four pairs of enantiomers, (+)-1 and (-)-1, (+)-2 and (-)-2, (+)-3 and (-)-3, and (+)-4 and (-)-4, by chiral HPLC. The structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses, quantum chemical calculations, quantitative measurements of molar rotations, application of van't Hoff's principle of optical superposition, and comparison with the literature data. The NMR and MS data of compound 3 are reported for the first time, as the structure was listed in SciFinder Scholar with no associated reference. These non-brominated pyrrole derivatives were found in this species for the first time. Compound 18 showed valuable cytotoxicities against HL-60, K562, and HCT-116 cell lines with IC50 values of 12.4, 16.0, and 19.8 µm, respectively. Compounds 16 - 19, 21, and 22 showed potent antifungal activities against Candida albicans with MIC values ranging from 0.59 to 4.69 µg/ml. Compounds 16 - 19 exhibited moderate antibacterial activities against Proteusbacillus vulgaris (MIC values ranging from 9.38 to 18.75 µg/ml).


Assuntos
Agelas/química , Alcaloides/isolamento & purificação , Diterpenos/isolamento & purificação , Pirróis/isolamento & purificação , Alcaloides/química , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Diterpenos/química , Células HCT116 , Células HL-60 , Humanos , Células K562 , Estrutura Molecular , Pirróis/química
20.
Chem Pharm Bull (Tokyo) ; 64(7): 691-4, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-27373625

RESUMO

In our continuing study for structurally and biogenetically interesting natural products from marine organisms, Okinawan marine sponges Agelas spp. were investigated, resulting in the isolation of 18 unique alkaloids including five dimeric bromopyrrole alkaloids (1-5), ten monomeric bromopyrrole alkaloids (6-15), and three conjugates of monomeric bromopyrrole alkaloid and hydroxykynurenine (16-18). In this mini-review, the isolation, structure elucidation, and antimicrobial activities of these alkaloids are summarized.


Assuntos
Agelas/química , Alcaloides/farmacologia , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Fungos/efeitos dos fármacos , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular
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