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1.
Mar Drugs ; 19(3)2021 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-33668842

RESUMO

Sponges are prolific sources of various natural products that have provided the chemical scaffolds for new drugs. The sponges of the genus Petrosia inhabit various regions and contain a variety of biologically active natural products such as polyacetylenes, sterols, meroterpenoids, and alkaloids. This review aims to provide a comprehensive summary of the chemical structures and biological activities of Petrosia metabolites covering a period of more than four decades (between 1978 and 2020). It is also described in this review that the major groups of metabolites from members of the genus Petrosia differed with latitude. The polyacetylenes were identified to be the most predominant metabolites in Petrosia sponges in temperate regions, while tropical Petrosia species were sources of a greater variety of metabolites, such as meroterpenoids, sterols, polyacetylenes, and alkaloids.


Assuntos
Produtos Biológicos/isolamento & purificação , Petrosia/metabolismo , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Produtos Biológicos/química , Humanos , Polímero Poliacetilênico/química , Polímero Poliacetilênico/isolamento & purificação , Polímero Poliacetilênico/farmacologia , Metabolismo Secundário , Esteróis/química , Esteróis/isolamento & purificação , Esteróis/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia
2.
BMC Evol Biol ; 19(1): 24, 2019 01 16.
Artigo em Inglês | MEDLINE | ID: mdl-30651060

RESUMO

BACKGROUND: Knowledge about the distribution of the genetic variation of marine species is fundamental to address species conservation and management strategies, especially in scenarios with mass mortalities. In the Mediterranean Sea, Petrosia ficiformis is one of the species most affected by temperature-related diseases. Our study aimed to assess its genetic structure, connectivity, and bottleneck signatures to understand its evolutionary history and to provide information to help design conservation strategies of sessile marine invertebrates. RESULTS: We genotyped 280 individuals from 19 locations across the entire distribution range of P. ficiformis in the Atlanto-Mediterranean region at 10 microsatellite loci. High levels of inbreeding were detected in most locations (especially in the Macaronesia and the Western Mediterranean) and bottleneck signatures were only detected in Mediterranean populations, although not coinciding entirely with those with reported die-offs. We detected strong significant population differentiation, with the Atlantic populations being the most genetically isolated, and show that six clusters explained the genetic structure along the distribution range of this sponge. Although we detected a pattern of isolation by distance in P. ficiformis when all locations were analyzed together, stratified Mantel tests revealed that other factors could be playing a more prominent role than isolation by distance. Indeed, we detected a strong effect of oceanographic barriers impeding the gene flow among certain areas, the strongest one being the Almeria-Oran front, hampering gene flow between the Atlantic Ocean and the Mediterranean Sea. Finally, migration and genetic diversity distribution analyses suggest a Mediterranean origin for the species. CONCLUSIONS: In our study Petrosia ficiformis showed extreme levels of inbreeding and population differentiation, which could all be linked to the poor swimming abilities of the larva. However, the observed moderate migration patterns are highly difficult to reconcile with such poor larval dispersal, and suggest that, although unlikely, dispersal may also be achieved in the gamete phase. Overall, because of the high genetic diversity in the Eastern Mediterranean and frequent mass mortalities in the Western Mediterranean, we suggest that conservation efforts should be carried out specifically in those areas of the Mediterranean to safeguard the genetic diversity of the species.


Assuntos
Fluxo Gênico , Variação Genética , Petrosia/genética , Migração Animal/fisiologia , Animais , Organismos Aquáticos/genética , Oceano Atlântico , Genética Populacional , Genótipo , Geografia , Mar Mediterrâneo , Densidade Demográfica
3.
Fitoterapia ; 127: 207-211, 2018 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29474977

RESUMO

As an attempt to utilize of rare earth elements as a novel method to activate the silent genes in fungus, the marine-derived fungus Penicillium citrinum was cultured under ordinary laboratory fermentation conditions in the presence of scandium chloride (ScCl3, 50 µM), and chemical investigation led to the isolation and characterization of three new peptide derivatives (1-3), along with four known pyrrolidine alkaloids (4-7). Those structures were elucidated by spectroscopic data interpretation, as well as chemical reactions. Comparative metabolic profiling of the culture extracts (with/without scandium chloride) indicated that compounds 1-3 scarcely detected in the absence of ScCl3. In addition, the antibacterial and cytotoxic activities of all isolated products were evaluated.


Assuntos
Alcaloides/isolamento & purificação , Penicillium/química , Pirrolidinas/isolamento & purificação , Animais , Linhagem Celular Tumoral , Fermentação , Humanos , Metaboloma , Testes de Sensibilidade Microbiana , Estrutura Molecular , Petrosia/microbiologia
4.
Mar Drugs ; 15(3)2017 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-28241489

RESUMO

Eight new sterols (1-5 and 11-13), together with eight known compounds (6-10 and 14-16) were isolated from marine sponge Petrosia sp. The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis. The cytotoxicity of some compounds against a panel of human cancer cell lines is also reported.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Neoplasias/tratamento farmacológico , Petrosia/química , Poríferos/química , Esteróis/química , Esteróis/farmacologia , Células A549 , Animais , Linhagem Celular Tumoral , Células HeLa , Células Hep G2 , Humanos , Tailândia
5.
Bioorg Med Chem Lett ; 27(4): 999-1002, 2017 02 15.
Artigo em Inglês | MEDLINE | ID: mdl-28109786

RESUMO

During the search for protein tyrosine phosphatase 1B (PTP1B) inhibitors from marine organisms, the known tetramic acid derivative, melophlin C (1), was isolated as an active component together with the new nortriterpenoid saponin, sarasinoside S (2), and three homologues: sarasinosides A1 (3), I1 (4), and J (5), from the Indonesian marine sponge Petrosia sp. The structure of 2 was elucidated on the basis of its spectroscopic data. Compound 1 inhibited PTP1B activity with an IC50 value of 14.6µM, while compounds 2-5 were not active at 15.2-16.0µM. This is the first study to report the inhibitory effects of a tetramic acid derivative on PTP1B activity.


Assuntos
Inibidores Enzimáticos/farmacologia , Glicosídeos/farmacologia , Petrosia/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Pirrolidinonas/farmacologia , Triterpenos/farmacologia , Animais , Inibidores Enzimáticos/química , Glicosídeos/química , Humanos , Concentração Inibidora 50 , Biologia Marinha , Pirrolidinonas/química , Triterpenos/química
6.
Planta Med ; 83(9): 805-811, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28095586

RESUMO

Chlamydiae are widely distributed pathogens of human populations, which can lead to serious reproductive and other health problems. In our search for novel antichlamydial metabolites from marine derived-microorganisms, one new (1) and two known (2, 3) dimeric indole derivatives were isolated from the sponge-derived actinomycete Rubrobacter radiotolerans. The chemical structures of these metabolites were elucidated by NMR spectroscopic data as well as CD calculations. All three metabolites suppressed chlamydial growth in a concentration-dependent manner. Among them, compound 1 exhibited the most effective antichlamydial activity with IC50 values of 46.6 ~ 96.4 µM in the production of infectious progeny. Compounds appeared to target the mid-stage of the chlamydial developmental cycle by interfering with reticular body replication, but not directly inactivating the infectious elementary body.


Assuntos
Actinobacteria/química , Antibacterianos/isolamento & purificação , Chlamydia trachomatis/efeitos dos fármacos , Indóis/farmacologia , Actinobacteria/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Antibacterianos/toxicidade , Chlamydia trachomatis/fisiologia , Células HeLa , Humanos , Indóis/química , Indóis/isolamento & purificação , Indóis/toxicidade , Estrutura Molecular , Petrosia/microbiologia
7.
J Nat Prod ; 79(3): 499-506, 2016 Mar 25.
Artigo em Inglês | MEDLINE | ID: mdl-26821210

RESUMO

Three new structurally related depsipeptides, halicylindramides F-H (1-3), and two known halicylindramides were isolated from a Petrosia sp. marine sponge collected off the shore of Youngdeok-Gun, East Sea, Republic of Korea. Their planar structures were elucidated by extensive spectroscopic data analyses including 1D and 2D NMR data as well as MS data. The absolute configurations of halicylindramides F-H (1-3) were determined by Marfey's method in combination with Edman degradation. The absolute configurations at C-4 of the dioxyindolyl alanine (Dioia) residues of halicylindramides G (2) and H (3) were determined as 4S and 4R, respectively, based on ECD spectroscopy. The C-2 configurations of Dioia in 2 and 3 were speculated to both be 2R based on the shared biogenesis of the halicylindramides. Halicylindramides F (1), A (4), and C (5) showed human farnesoid X receptor (hFXR) antagonistic activities, but did not bind directly to hFXR.


Assuntos
Depsipeptídeos , Petrosia/química , Receptores Citoplasmáticos e Nucleares/efeitos dos fármacos , Animais , Depsipeptídeos/química , Depsipeptídeos/isolamento & purificação , Depsipeptídeos/farmacologia , Humanos , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , República da Coreia
9.
Chem Pharm Bull (Tokyo) ; 63(6): 469-75, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25854125

RESUMO

Six new polyacetylenic alcohols, termed strongylotriols A and B; pellynols J, K, and L; and isopellynol A, together with three known polyacetylenic alcohols, pellynols A, B, and C were isolated from the marine sponges Petrosia sp., and Halichondria sp. collected in Okinawa, Japan. Their planer structures were determined based on 2D-NMR and mass spectrometric analysis of the degraded products by RuCl3 oxidation. The absolute stereochemistry of isolates was examined by their Mosher's esters. The strongylotriols were found to be optically pure compounds, whereas the pellynols are diastereomeric mixtures at the C-6 position. Proliferation experiments using the HeLa and K562 cell lines suggested that the essential structural units for activity are the "hexa-2,4-diyn-1,6-diol" and "pent-1-en-4-yn-3-ol" on the termini.


Assuntos
Álcoois/química , Petrosia/química , Poli-Inos/química , Poríferos/química , Álcoois/isolamento & purificação , Álcoois/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Células HeLa , Humanos , Neoplasias/tratamento farmacológico , Poli-Inos/isolamento & purificação , Poli-Inos/farmacologia
10.
Bioorg Med Chem Lett ; 24(22): 5315-7, 2014 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-25278237

RESUMO

Halenaquinone was isolated from the marine sponge Petrosia alfiani as an inhibitor of osteoclastogenic differentiation of murine RAW264 cells. It inhibited the RANKL (receptor activator of nuclear factor-κB ligand)-induced upregulation of TRAP (tartrate-resistant acid phosphatase) activity as well as the formation of multinuclear osteoclasts. In addition, halenaquinone substantially suppressed RANKL-induced IκB degradation and Akt phosphorylation. Thus, these results suggest that halenaquinone inhibits RANKL-induced osteoclastogenesis at least by suppressing the NF-κB and Akt signaling pathways.


Assuntos
Quinonas/química , Animais , Diferenciação Celular/efeitos dos fármacos , Linhagem Celular , Proteínas I-kappa B/metabolismo , Camundongos , Osteoclastos/citologia , Osteoclastos/efeitos dos fármacos , Osteoclastos/metabolismo , Osteogênese/efeitos dos fármacos , Petrosia/química , Petrosia/metabolismo , Fosforilação/efeitos dos fármacos , Proteínas Proto-Oncogênicas c-akt/metabolismo , Quinonas/isolamento & purificação , Quinonas/farmacologia , Ligante RANK/toxicidade , Transdução de Sinais/efeitos dos fármacos
11.
Int J Mol Sci ; 15(9): 16511-21, 2014 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-25238415

RESUMO

The sponge Petrosia sp. yielded five polyacetylenic compounds (1-5), including two new polyacetylenes, petrosianynes A (1) and B (2). The structures of these compounds were elucidated by detailed spectroscopic analysis and by comparison with the physical and spectral data of related known analogues. Compounds 1-5 exhibited significant cytotoxic activity against a limited panel of cancer cell lines.


Assuntos
Petrosia/química , Poli-Inos/isolamento & purificação , Adenocarcinoma/patologia , Animais , Neoplasias da Mama/patologia , Linhagem Celular Tumoral , Neoplasias do Colo/patologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Leucemia/patologia , Masculino , Estrutura Molecular , Poli-Inos/química , Poli-Inos/farmacologia , Neoplasias da Próstata/patologia
12.
Nat Prod Commun ; 8(9): 1209-12, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24273847

RESUMO

One new biscembranoid, petronigrione (1), and five known compounds, methyl tortuoate B (2), lobophytone U (3), lobophytone H (4), (24S)-ergostane 3beta, 5alpha, 6beta, 25 tetraol-25-monoacetate (5), and (24S)-ergostane-1beta, 3beta, 5alpha, 6beta, 25-pentaol-25-monoacetate (6), were isolated from the methanol extract of the marine sponge Petrosia nigricans. Their structures were established on the basis of spectral and chemical evidence. The cytotoxicity of all compounds was evaluated by MTT assay on four human cancer cell lines, HepG2, KB, LU-1, and MCF-7. Compounds 1 and 2 exhibited moderate cytotoxic activities on the four human cancer cell lines with IC50 values ranging of 20.7 - 28.9 microg/mL.


Assuntos
Antineoplásicos/isolamento & purificação , Diterpenos/isolamento & purificação , Petrosia/química , Animais , Antineoplásicos/química , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Células MCF-7 , Estrutura Molecular
13.
ChemMedChem ; 8(11): 1779-86, 2013 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-24014463

RESUMO

Illumination by acetylene: Systematic structural variations in a series of archetypal acetylenic lipids derived from the naturally occurring (S,E)-icos-4-en-1-yn-3-ol allowed the discovery of a series of 3R-like 1,4-di-unsaturated carbinol units with a significant and systematic enantiomeric effect on cytotoxicity.


Assuntos
Alcanos , Alcenos , Antineoplásicos , Descoberta de Drogas , Metanol , Alcanos/química , Alcanos/farmacologia , Alcenos/química , Alcenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Concentração Inibidora 50 , Metanol/química , Metanol/farmacologia , Estrutura Molecular , Petrosia/química , Estereoisomerismo
14.
J Nat Prod ; 76(3): 425-32, 2013 Mar 22.
Artigo em Inglês | MEDLINE | ID: mdl-23368996

RESUMO

Four new compounds, (-)-petrosynoic acids A-D (1-4), and five known congeners, pellynols A (5), C (6), D (7), F (8), and I (9), were isolated from a Petrosia sp. marine sponge collected in American Samoa. Isolation work was guided by cytotoxicity against human lung cancer cells (H460). The structures of the C31-C33 polyacetylenes (1-9) were determined on the basis of 1D- and 2D-NMR analysis, mass spectrometry, and comparison of specific rotation values. Compounds 1-9 were found to be broadly cytotoxic with limited selectivity for cancer cells, as they were all moderately active against the A2058 (melanoma), H522-T1 (lung), and H460 (lung) human cancer cell lines as well as IMR-90 quiescent human fibroblast cells.


Assuntos
Antineoplásicos , Petrosia/química , Poli-Inos , Samoa Americana , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Poli-Inos/química , Poli-Inos/isolamento & purificação , Poli-Inos/farmacologia
15.
Lipids ; 48(1): 87-91, 2013 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-23077003

RESUMO

A novel petrosiacetylene analog (petrosiacetylene E) has been isolated from the Korean marine sponge Petrosia sp., along with petrosiacetylene A, B and C. Their structures were elucidated on the basis of spectroscopic methods and the stereochemistry of the new compound was determined by using the modified Mosher's method. Petrosiacetylene E showed higher cytotoxicity against five human cancer cell lines than petrosiacetylene A and B, presumably due to the additional hydroxy group located at C-16.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Petrosia/química , Poli-Inos/química , Poli-Inos/farmacologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Neoplasias/tratamento farmacológico , Poli-Inos/isolamento & purificação
16.
Microbes Environ ; 27(1): 99-104, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-22214828

RESUMO

Actinobacteria associated with 3 marine sponges, Cinachyra sp., Petrosia sp., and Ulosa sp., were investigated. Analyses of 16S rRNA gene clone libraries revealed that actinobacterial diversity varied greatly and that Ulosa sp. was most diverse, while Cinachyra sp. was least diverse. Culture-based approaches failed to isolate actinobacteria from Petrosia sp. or Ulosa sp., but strains belonging to 10 different genera and 3 novel species were isolated from Cinachyra sp.


Assuntos
Actinobacteria/crescimento & desenvolvimento , Actinobacteria/isolamento & purificação , Poríferos/microbiologia , Actinobacteria/classificação , Actinobacteria/genética , Animais , Biodiversidade , DNA Bacteriano/genética , Dados de Sequência Molecular , Petrosia/classificação , Petrosia/microbiologia , Filogenia , Poríferos/classificação , RNA Ribossômico 16S/genética , Especificidade da Espécie
17.
Biochem Biophys Res Commun ; 415(1): 6-10, 2011 Nov 11.
Artigo em Inglês | MEDLINE | ID: mdl-21982768

RESUMO

Green plant-origin electrophilic compounds are a newly-recognized class of neuroprotective compounds that provide neuroprotection through activation of the Nrf2/ARE pathway. Electrophilic hydroquinones are of particular interest due to their ability to become electrophilic quinones upon auto-oxidation. Although marine organisms frequently produce a variety of electrophilic compounds, the detailed mechanisms of action of these compounds remain unknown. Here, we focused on the neuroprotective effects of strongylophorine-8 (STR8), a para-hydroquinone-type pro-electrophilic compound from the sponge Petrosia (Strongylophora) corticata. STR8 activated the Nrf2/ARE pathway, induced phase 2 enzymes, and increased glutathione, thus protecting neuronal cells from oxidative stress. Microarray analysis indicated that STR8 induced a large number of phase 2 genes, the regulation of which is controlled by the Nrf2/ARE pathway. STR8 is the first example of a neuroprotective pro-electrophilic compound from marine organisms.


Assuntos
Fator 2 Relacionado a NF-E2/metabolismo , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Petrosia/química , Animais , Antioxidantes/farmacologia , Linhagem Celular , Humanos , Neurônios/metabolismo , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Elementos de Resposta/efeitos dos fármacos
18.
J Nat Prod ; 74(5): 1262-7, 2011 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-21534590

RESUMO

Six linear acetylenes, (-)-duryne (1) and (-)-durynes B-F (2-6), were isolated from the marine sponge Petrosia sp. Their structures were elucidated by NMR and tandem FABMS analyses. The positions of the olefinic bonds were confirmed by ozonolysis experiments, and the absolute configurations were determined by the modified Mosher's method. Compound 1 was found to be the enantiomer of duryne, a previously reported sponge metabolite. Compounds 1-6 show cytotoxicity against HeLa cells with IC50 values between 0.08 and 0.50 µM.


Assuntos
Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Petrosia/química , Poli-Inos/isolamento & purificação , Poli-Inos/farmacologia , Animais , Antineoplásicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Japão , Biologia Marinha , Estrutura Molecular , Poli-Inos/química , Estereoisomerismo
19.
Toxicon ; 57(6): 889-96, 2011 May.
Artigo em Inglês | MEDLINE | ID: mdl-21396391

RESUMO

Marine cyanobacteria are photosynthetic prokaryotes of significant ecological interest, living free or in association with invertebrates. They are also considered as excellent sources of antineoplastic, antibacterial, antiviral and antifungal compounds. In this work, aqueous extracts from eight cyanobacterial strains isolated from the Mediterranean sponge Petrosia ficiformis have been investigated for their bioactive properties. Bioassays with human erythrocytes, Artemia salina nauplii, and Paracentrotus lividus gametes and embryos were performed. Some aqueous extracts exhibited citolytic effect on human erythrocytes and toxic activity against A. salina nauplii. Furthermore antimitotic activity was evidenced during sea urchin embryos development and disorganization of blastomeres with altered cell-cell contact was also induced. Some of the isolated cyanobacterial strains, belonging to Leptolyngbya and Synechococcus genera with an high citotoxic activity, should be further investigated to better characterize their bioactive molecules. Our data confirm cyanobacteria as an interesting source of novel bioactive compounds with potential applications in pharmaceutics.


Assuntos
Cianobactérias/química , Toxinas Marinhas/isolamento & purificação , Toxinas Marinhas/toxicidade , Petrosia/microbiologia , Animais , Artemia/efeitos dos fármacos , Bioensaio/métodos , Cianobactérias/crescimento & desenvolvimento , Relação Dose-Resposta a Droga , Eritrócitos/efeitos dos fármacos , Humanos , Dose Letal Mediana , Mar Mediterrâneo , Ouriços-do-Mar/efeitos dos fármacos , Ouriços-do-Mar/embriologia
20.
Org Lett ; 12(22): 5196-9, 2010 Nov 19.
Artigo em Inglês | MEDLINE | ID: mdl-20954723

RESUMO

The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki-Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.


Assuntos
Alcaloides/síntese química , Quinolizidinas/síntese química , Alcaloides/química , Animais , Catálise , Ciclização , Biologia Marinha , Estrutura Molecular , Petrosia/química , Quinolizidinas/química , Estereoisomerismo
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