RESUMO
The chemical screening of an octocoral identifed as Junceella fragilis has led to the isolation of five chlorinated briarane-type diterpenoids, including three known metabolites, gemmacolide X (1), frajunolide I (2), and fragilide F (3), along with two new analogs, 12α-acetoxyfragilide F (4) and 12α-acetoxyjunceellin (5). Single-crystal X-ray diffraction analysis was carried out to determine the absolute configurations of 1 and 2, while the structures of new compounds 4 and 5 were ascertained with 2D NMR experiments. Briaranes 1 and 3-5 were active in enhancing alkaline phosphatase (ALP) activity.
RESUMO
The marine sponge Lendenfeldia sp., collected from the Southern waters of Taiwan, was subjected to chemical composition screening, resulting in the isolation of four new 24-homoscalarane compounds, namely lendenfeldaranes R-U (1-4). The structures and relative stereochemistry of the new metabolites 1-4 were assigned based on NMR studies. The absolute configurations of compounds 1-4 were determined by comparing the calculated and experimental values of specific optical rotation. The antioxidant and anti-inflammatory activities of the isolated compounds were assayed using superoxide anion generation and elastase release assays. These assays are used to determine neutrophilic inflammatory responses of respiratory burst and degranulation. Compounds 2 and 4 inhibited superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB) with IC50: 3.98-4.46 µM. Compounds 2 and 4 inhibited fMLP/CB-induced elastase release, with IC50 values ranging from 4.73 to 5.24 µM. These findings suggested that these new 24-homoscalarane compounds possess unique structures and potential anti-inflammatory activity.
RESUMO
A formerly unpublicized briarane diterpenoid, briastecholide M (1), and its established analogue, brianodin B (2), were purified from Briareum stechei, an octocoral collected from Okinawan waters. Using spectroscopic methods, the structure of 1 was established. Functional study showed that 1 can reducing the release of inducible nitric oxide synthase (iNOS) but enhancing cyclooxygenase-2 (COX-2) protein expression.
Assuntos
Antozoários , Diterpenos , Animais , Antozoários/química , Antozoários/metabolismo , Diterpenos/farmacologia , Diterpenos/química , Óxido Nítrico Sintase Tipo II/metabolismo , Ciclo-Oxigenase 2/metabolismoRESUMO
A known polyoxygenated briarane, briaexcavatolide P (1), was isolated from a Formosan octocoral Briareum stechei. Moreover, the same species B. stechei, collected from Okinawan waters, yielded three chlorine-containing briaranes, including two new compounds, briastecholides B (2) and C (3) as well as a known analogue, briarenol R (4). The structures of 1-4 were established using spectroscopic methods. In addition, briarane 1 demonstrated anti-inflammatory activity in lipo-polysaccharide-induced RAW 264.7 mouse macrophage cells by suppressing the expression of inducible nitric oxide synthase (iNOS) protein.
Assuntos
Antozoários/química , Diterpenos/química , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Camundongos , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Células RAW 264.7RESUMO
Sponge-derived scalaranes are remarkable sesterterpenoids previously found to exhibit profound inhibitory effects against neutrophilic inflammation. In our current work, we constructed the metabolomic profile of marine sponge Lendenfeldia sp. for the first time using a tandem mass spectrometry (MS/MS) molecular networking approach. The results highlighted the rich chemical diversity of these scalaranes, motivating us to conduct further research to discover novel scalaranes targeting neutrophilic inflammation. MS- and NMR-assisted isolation and elucidation led to the discovery of seven new homoscalaranes, lendenfeldaranes K-Q (1-7), characterized by methylation at C-24, together with five known derivatives, lendenfeldarane B (8), 25-nor-24-methyl-12,24-dioxoscalar-16-en-22-oic acid (9), 24-methyl-12,24,25-trioxoscalar-16-en-22-oic acid (10), felixin B (11), and 23-hydroxy-20-methyldeoxoscalarin (12). Scalaranes 1-4 and 6-12 were assayed against superoxide anion generation and elastase release, which represented the neutrophilic inflammatory responses of respiratory burst and degranulation, respectively. The results indicated that 1-3 and 6-12 exhibited potential anti-inflammatory activities (IC50 for superoxide anion scavenging: 0.87~6.57 µM; IC50 for elastase release: 1.12~6.97 µM).
Assuntos
Anti-Inflamatórios/farmacologia , Neutrófilos/efeitos dos fármacos , Poríferos , Sesterterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Organismos Aquáticos , Humanos , Inflamação/prevenção & controle , Sesterterpenos/química , Relação Estrutura-AtividadeRESUMO
In this review, 170 natural substances, including steroid, diterpenoid, sesquiterpenoid, peptide, prostaglandin, base, chlorolipid, bicyclolactone, amide, piperazine, polyketide, glycerol, benzoic acid, glycyrrhetyl amino acid, hexitol, pentanoic acid, aminoethyl ester, octadecanone, alkaloid, and a 53-kD allergenic component from octocorals belonging to genus Dendronephthya, were listed. Some of these compounds displayed potential bioactivities.
Assuntos
Antozoários/metabolismo , Produtos Biológicos/química , Alérgenos/química , Alérgenos/metabolismo , Aminoácidos/química , Aminoácidos/metabolismo , Animais , Produtos Biológicos/metabolismo , Prostaglandinas/química , Prostaglandinas/metabolismo , Esteroides/química , Esteroides/metabolismo , Terpenos/química , Terpenos/metabolismoRESUMO
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.
Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Ciclo-Oxigenase 2/metabolismo , Diterpenos/farmacologia , Óxido Nítrico Sintase Tipo II/metabolismo , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Regulação para Baixo , Regulação Enzimológica da Expressão Gênica/efeitos dos fármacos , Camundongos , Estrutura Molecular , Células RAW 264.7RESUMO
Post-transcriptional regulatory mechanisms play important roles in the regulation of LC-PUFA biosynthesis. Our previous study revealed that miR-33 could increase the expression of fatty acyl desaturases (fads2) in the rabbitfish Siganus canaliculatus, but the specific mechanism is unknown. Here, we confirmed that miR-33 could target the 3'UTR of insulin-induced gene 1 (insig1), resulting in downregulation of its protein level in the rabbitfish hepatocyte line (SCHL). In vitro overexpression of miR-33 inhibited the mRNA level of insig1 and increased the mRNA levels of Δ6Δ5 fads2 and elovl5, as well as srebp1. In SCHL cells, proteolytic activation of sterol-regulatory-element-binding protein-1 (Srebp1) was blocked by Insig1, with overexpression of insig1 decreasing mature Srebp1 level, while inhibition of insig1 led to the opposite effect. Srebp1 could enhance the promoter activity of Δ6Δ5 fads2 and elovl5, whose expression levels decreased with knockdown of srebp1 in SCHL. Overexpression of miR-33 also resulted in a higher conversion of 18:3n-3 to 18:4n-3 and 20:5n-3 to 22:5n-3, linked to desaturation and elongation via Δ6Δ5 Fads2 and Elovl5, respectively. The results suggested that the mechanism by which miR-33 regulates LC-PUFA biosynthesis in rabbitfish is through enhancing the expression of srebp1 by targeting insig1. The findings here provide more insight to the mechanism of miRNAs involvement in the regulation of LC-PUFA biosynthesis in teleosts.
Assuntos
Ácidos Graxos Dessaturases/genética , Ácidos Graxos Insaturados/biossíntese , Proteínas de Peixes/genética , MicroRNAs/genética , Perciformes/genética , Proteína de Ligação a Elemento Regulador de Esterol 1/genética , Regiões 3' não Traduzidas , Animais , Linhagem Celular , Clonagem Molecular , Ácidos Graxos Dessaturases/metabolismo , Proteínas de Peixes/metabolismo , Expressão Gênica , Regulação da Expressão Gênica , Vetores Genéticos/química , Vetores Genéticos/metabolismo , Células HEK293 , Hepatócitos/citologia , Hepatócitos/metabolismo , Humanos , Metabolismo dos Lipídeos/genética , MicroRNAs/metabolismo , Perciformes/metabolismo , Regiões Promotoras Genéticas , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismo , Transdução de Sinais , Proteína de Ligação a Elemento Regulador de Esterol 1/metabolismoRESUMO
Two new briarane metabolitesfragilides K (1) and L (2)along with five known analoguesgemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (3â»7)were extracted and purified from Junceella fragilis, a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes 1 and 2 were determined and the cyclohexane rings in 1 and 2 were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes 2, 3, and 6 inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes 3 and 7 suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.
Assuntos
Antozoários/química , Anti-Inflamatórios/química , Diterpenos/química , Expressão Gênica/efeitos dos fármacos , Animais , Antozoários/metabolismo , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Configuração de Carboidratos , Sobrevivência Celular/efeitos dos fármacos , Ciclo-Oxigenase 2/genética , Ciclo-Oxigenase 2/metabolismo , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Lactonas/química , Lactonas/isolamento & purificação , Lactonas/farmacologia , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/metabolismo , Proteínas de Plantas/química , Proteínas de Plantas/isolamento & purificação , Proteínas de Plantas/farmacologia , Células RAW 264.7RESUMO
A new type of combined ecological floating bed was developed on Swan Lake. It was combined with aquatic and hydrophilous plants and ancillary equipments that included floating controllers, water-cycling aerator systems and wave-making systems. Combined ecological floating bed changed the physical and chemical environment of Swan Lake and had an effect on the transportation and transformation of TN, NH4(+) -N and TP between overlying water and sediment during the experiment. The concentration change of TN, NH4(+) -N and TP and the effect of DO, Eh and pH on the nutrient in the overlying water and sediment were investigated. The results indicated that: in overlying water, the removal efficiencies of TN, NH4(+) -N and TP were 61.92%, 63.09% and 80.0%, respectively; the removal efficiencies of TN and NH4(+) -N were 23.79% and 37.04%, respectively; the concentration of TP increased by 43.71% in sediment during the experiment. The combined ecological floating bed influenced environmental factors such as DO, Eh and pH in overlying water in some degree. DO concentration rose from 8.7-8.9 mg x L(-1) to 9.3-10.4 mg x L(-1), and Eh concentration was from 163-178 mV to 191-198 mV. Both of them were higher than those in the contrast area. Phosphorus release was inhibited, and phosphorus adsorption was promoted through improving DO and Eh of the overlying water. The pH volatility was less and maintained between 7.51 and 8.32, and did not promote phosphorus release in sediment. TN, TP and NH4(+) -N in overlying water and TN and NH4(+) -N in sediment were significantly positively correlated with each other and with TP in sediment. The pH had no significant correlation with TN, TP and NH4(+) -N in overlying water and sediment. DO was significantly positively corrected with Eh in overlying water and was significantly negatively corrected with TP in sediment.
Assuntos
Sedimentos Geológicos/química , Lagos/química , Nitrogênio/análise , Fósforo/análise , Água Doce/química , PlantasRESUMO
OBJECTIVE: To investigate the relation between various risk factors and benign prostatic hyperplasia (BPH). METHODS: A population based case-control study was conducted, including 100 BPH patients over 60 years old living in suburb of Shenyang as study group, and 100 elderly men with non-BPH (excluding prostatic cancer and prostatitis) as control group. Chi(2) test and non-conditional logistic regression were used for monovariate analysis and multivariate analysis, respectively. RESULTS: Data from monovariate analysis showed that BPH incidence was significantly related to body weight index, cigarette smoking, alcohol drinking, meal intake at the beginning of 1980's, hypertention and prostatitis, respectively. While multivariate non-conditional logistic analysis showed that BPH was related to five factors: prostatitis (OR = 5.577, 95% CI: 2.147 - 14.482), monthly intake of meats at the beginning of 1980's (OR = 4.930, 95% CI: 2.404 - 10.111), diastolic blood pressure (OR = 1.050, 95% CI: 1.017 - 1.083), cigarette smoking (OR = 0.660, 95% CI: 0.500 - 0.872) and alcohol consumption (OR = 0.650, 95% CI: 0.480 - 0.881). CONCLUSION: Prostatitis, monthly excessive intake of meats at the beginning of 1980's and high diastolic blood pressure were possible risk factors for BPH, while heavy cigarette smoking and alcohol consumption were possible protective factors for BPH.