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1.
Molecules ; 25(6)2020 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-32204524

RESUMO

Five 8,17-epoxybriaranes, including three new compounds-briarenols I-K (1-3), along with two known analogues, briaexcavatolide P (4) and briaexcavatin P (5), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR studies and (+)-HRESIMS. Briarane 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7.

2.
Mar Drugs ; 18(2)2020 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-31991544

RESUMO

In the current study, an NMR spectroscopic pattern-based procedure for probing scalarane derivatives was performed and four new 24-homoscalaranes, lendenfeldaranes A-D (1- 4), along with three known compounds, 12α-acetoxy-22-hydroxy-24-methyl-24-oxoscalar-16-en- 25-al (5), felixin F (6), and 24-methyl-12,24,25-trioxoscalar-16-en-22-oic acid (7) were isolated from the sponge Lendenfeldia sp. The structures of scalaranes 1-7 were elucidated on the basis of spectroscopic analysis. Scalaranes 1-7 were further evaluated for their cytotoxicity toward a series of human cancer cell lines and the results suggested that 5 and 7 dominated in the anti- proliferative activity of the extract. The 18-aldehyde functionality was found to play a key role in their activity.

3.
Mar Drugs ; 17(12)2019 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-31847481

RESUMO

Three new 11,20-epoxybriaranes-fragilides U-W (1-3), as well as two known metabolites, junceellonoid D (4) and junceellin (5), were obtained from the octocoral Junceella fragilis. The structures of briaranes 1-3 were elucidated by spectroscopic methods and briaranes 3 and 5 displayed inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW264.7.

4.
Mar Drugs ; 17(9)2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31514359

RESUMO

Two new steroids, dendronesterones D (1) and E (2), featuring with 1,4-dienone moiety, along with three known steroids, methyl 3-oxochola-4,22-diene-24-oate (3), 5α,8α-epidioxy-24(S)- methylcholesta-6,22-dien-3ß-ol (4), and 5α,8α-epidioxy-24(S)-methylcholesta-6,9(11),22-trien-3ß-ol (5), were isolated from an octocoral Dendronephthya sp. The structures of steroids 1 and 2 were elucidated by using spectroscopic methods and steroid 1 was found to exhibit significant in vitro anti-inflammatory activity in lipopolysaccharides (LPS)-induced RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Esteroides/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Células RAW 264.7 , Esteroides/isolamento & purificação
5.
Mar Drugs ; 17(9)2019 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-31540107

RESUMO

Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17ß-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Espectroscopia de Prótons por Ressonância Magnética , Células RAW 264.7 , Relação Estrutura-Atividade
6.
Molecules ; 24(13)2019 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-31284657

RESUMO

Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found.


Assuntos
Antozoários/química , Diterpenos/química , Proteínas de Plantas/química , Animais , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Proteínas de Plantas/isolamento & purificação , Proteínas de Plantas/farmacologia , Análise Espectral
7.
Mar Drugs ; 17(4)2019 Apr 05.
Artigo em Inglês | MEDLINE | ID: mdl-30959843

RESUMO

Three new furanocembranoids-briaviodiol F (1) and briaviotriols A (2) and B (3)-along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 1⁻3 were elucidated by using spectroscopic methods. In vitro study demonstrated that compounds 2 and 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW 264.7, a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Modelos Moleculares , Estrutura Molecular , Células RAW 264.7
8.
Mar Drugs ; 16(3)2018 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-29495481

RESUMO

Four new briarane diterpenoids, briaviolides K-N (1-4), have been obtained from the cultured-type octocoral Briareum violaceum. Using a spectroscopic approach, the structures of briaranes 1-4 were identified. This study employed an in vitro model of lipopolysaccharide (LPS)-induced inflammation in the murine macrophage RAW 264.7 cell line, and found that among the four briaranes, briarane 2 possessed anti-inflammatory activity against inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expressions in cells. In addition, principal component analysis using the chemical global positioning system (ChemGPS) for natural products (ChemGPS-NP) was employed in order to analyze the structure-activity relationship (SAR), and the results indicated that the ring conformation of the compound has a leading role in suppressing the expressions of pro-inflammatory iNOS and COX-2 proteins in macrophages.


Assuntos
Antozoários/metabolismo , Anti-Inflamatórios/farmacologia , Produtos Biológicos/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/uso terapêutico , Produtos Biológicos/química , Produtos Biológicos/uso terapêutico , Ciclo-Oxigenase 2/metabolismo , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/uso terapêutico , Inflamação/tratamento farmacológico , Inflamação/imunologia , Inflamação/patologia , Lipopolissacarídeos/imunologia , Espectroscopia de Ressonância Magnética , Camundongos , Modelos Moleculares , Conformação Molecular , Óxido Nítrico Sintase Tipo II/metabolismo , Análise de Componente Principal , Células RAW 264.7 , Relação Estrutura-Atividade
9.
Mar Drugs ; 16(1)2018 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-29316672

RESUMO

Our continuous search for marine bioactive secondary metabolites led to the screening of crude extracts from a variety of aquaculture soft corals. The ethyl acetate (EtOAc) extract of Lobophytum crassum showed a distinctive chemical profile that was different from the wild type. It demonstrated significant anti-proliferative activity against Molt 4 leukemia cell with an IC50 value of 1 µg/mL after 24 h. Chemical investigation focusing on the unique peaks in L. crassum profile led to the discovery of a new α-tocopherol crassumtocopherol C (1), and two new cembrane-based diterpenoids culobophylins D (2) and E (3), along with ten known cembranoids (4-13). The structures of these isolates were elucidated using extensive spectroscopic techniques and a comparison with previously published data of related metabolites. Compound 2 was found to possess the first identified saturated internal C4-O-C14 linkage six-membered ring among all cembrane-type diterpenoids. The anti-proliferative activity of all the isolates (except 3) was evaluated against a limited panel of leukemia cell lines (Molt 4, K562, U937, and Sup-T1). The major compounds 8 and 10 exhibited the most anti-proliferative potent effect, with IC50 values ranging from 1.2 to 7.1 µM. The Structure Activity Relationship (SAR) of the isolates suggested that the presence of lactone moieties is crucial for the anti-proliferative activity against leukemia cells. Our work indicated that the development of an efficient aquaculture protocols for soft corals led to the discovery of new secondary metabolites with unique structural features. Such protocols can lead to a sustainable supply of biologically active compounds in enough quantities for the pharmaceutical industry.


Assuntos
Antozoários/metabolismo , Antineoplásicos/farmacologia , Diterpenos/farmacologia , Leucemia/tratamento farmacológico , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Aquicultura , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Humanos , Concentração Inibidora 50 , Metabolismo Secundário , Análise Espectral , Relação Estrutura-Atividade
10.
Steroids ; 115: 123-129, 2016 11.
Artigo em Inglês | MEDLINE | ID: mdl-27553726

RESUMO

Four new marine sterols, (22E,24R)-ergosta-5,22-diene-3ß,11α-diol (1), (24S)-ergosta-5-ene-3ß,11α-diol (2), 5α,6α-epoxy-23-demethylgorgost-8-ene-3ß,7α-diol (3), and 5α,6α-epoxy-23-demethylgorgost-8(14)-ene-3ß,7α-diol (4), along with a known metabolite, 23-demethylgorgost-7-ene-3ß,5α,6ß-triol (5), were isolated from an algal-bearing gorgonian coral Pinnigorgia sp., collected off the waters of Taiwan. The structures of these sterols were elucidated on the basis of spectroscopic methods. Sterols 1-5 were tested for in vitro cytotoxicity in hepatic stellate cells (HSCs). Proliferation of HSCs plays a key role in the pathogenesis of liver fibrosis.


Assuntos
Antozoários/química , Antozoários/microbiologia , Esteróis/química , Animais , Espectroscopia de Ressonância Magnética , Estrutura Molecular
11.
Nat Prod Commun ; 11(12): 1783-1784, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30508332

RESUMO

A natural caulerpenyne-derived sesquiterpene, oxytoxin-2 (1), was isolated from a cultured mollusc Volvatella vigourouxi. The structure of 1 was elucidated on the basis of spectroscopic analysis and this compound was suggested to be a diet-derived metabolite from the green alga Caulerpa sertularioides.-This is the first study on the chemical constituents of V. vigourouxi. Oxytoxin-2 (1) was found to inhibit significantly the expression of the pro-inflammatory inducible nitric oxide synthase (iNOS) protein of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.


Assuntos
Anti-Inflamatórios/farmacologia , Clorófitas/química , Gastrópodes , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Dieta , Humanos , Lipopolissacarídeos/farmacologia , Camundongos , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
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