RESUMEN
A new monogalactosyldiacylglycerol (MGDG), a known monogalactosylmonoacylglycerol (MGMG) and a known polyunsaturated fatty acid methyl ester (PUFAME) were isolated from the marine dinoflagellate Karenia mikimotoi. The planar structure of the glycolipids was elucidated using mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses and comparisons to the known glycolipid to confirm its structure. The MGDG was characterized as 3-O-ß-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoyl-2-O-tetradecanoylglycerol 1. The MGMG and PUFAME were characterized as (2S)-3-O-ß-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoylglycerol 2 and Methyl (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate 3, respectively. The isolation of the PUFAME strongly supports the polyunsaturated fatty acid (PUFA) fragment of these glycolipids. The relative configuration of the sugar was deduced by comparisons of 3JHH values and proton chemical shifts with those of known glycolipids. All isolated compounds MGDG, MGMG and PUFAME 1-3 were evaluated for their antimicrobial and anti-inflammatory activity. All compounds modulated macrophage responses, with compound 3 exhibiting the greatest anti-inflammatory activity.
Asunto(s)
Antiinflamatorios/farmacología , Dinoflagelados , Ácidos Grasos Insaturados/química , Glucolípidos/química , Macrófagos/efectos de los fármacos , Animales , Ratones , Océanos y Mares , Células RAW 264.7/efectos de los fármacosRESUMEN
Gentiopicroside is a major active component of the Gentiana scabra Bge., which is commonly used as herbal medicine for the treatment of inflammation in Asia. Gentiopicroside significantly down-regulated expression of key adipogenic transcription factors (PPARγ, C/EBPα, SREBP-1c) and dose-dependently inhibited the lipid uptake-related gene (LPL), fatty acid transport-related gene (FABP4) and triglyceride (TG) synthesis-related gene (DGAT2), as well as fatty acid synthesis-related genes (FAS, SCD1), which resulted in reduced intracellular lipid droplet accumulation and TG content in 3T3-L1 cells. Gentiopicroside also down-regulated expression of inflammatory cytokine genes (NFκB1, TNFα, IL6) compared with vehicle. Oral administration of gentiopicroside (50â¯mg/kg) in mice fed with high-fat diet for 12â¯weeks resulted in reduced body weight and visceral fat mass compared with the control group. Overall, the results of this study showed that gentiopicroside had positive anti-obesity effects by regulating the expression of adipogenesis/lipogenesis-related genes and inflammatory genes in 3T3-L1, and that it effectively reduced body weight and visceral fat mass in vivo.
Asunto(s)
Células 3T3-L1/efectos de los fármacos , Adipogénesis/efectos de los fármacos , Fármacos Antiobesidad/uso terapéutico , Peso Corporal/efectos de los fármacos , Gentiana/química , Glucósidos Iridoides/uso terapéutico , Animales , Fármacos Antiobesidad/farmacología , Glucósidos Iridoides/farmacología , Masculino , Ratones , Ratones ObesosRESUMEN
Antartin (1), a new zizaane-type sesquiterpene, was isolated from Streptomyces sp. SCO736. The chemical structure of 1 was assigned from the interpretation of 1D and 2D NMR in addition to mass spectrometric data. The relative stereochemistry of 1 was determined by analysis of NOE data, while the absolute stereochemistry was decided based on a comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Antartin (1) showed cytotoxicity against A549, H1299, and U87 cancer cell lines by causing cell cycle arrest at the G1 phase.
Asunto(s)
Citotoxinas/química , Sesquiterpenos/química , Streptomyces/química , Células A549 , Regiones Antárticas , Línea Celular Tumoral , Dicroismo Circular , Citotoxinas/farmacología , Fase G1/efectos de los fármacos , Sedimentos Geológicos/microbiología , Humanos , Espectroscopía de Resonancia Magnética/métodos , Sesquiterpenos/farmacologíaRESUMEN
Bioactivity-guided isolation of a crude extract from a culture broth of Bacillus sp. has led to the isolation of (-)-4-hydroxysattabacin (1). The inhibitory effect of (-)-4-hydroxysattabacin (1) was investigated on melanogenesis in the murine melanoma cell line, B16F10, and human melanoma cell line, MNT-1, as well as a pigmented 3D-human skin model. (-)-4-Hydroxysattabacin treatment decreased melanin contents in a dose-dependent manner in α-melanocyte stimulating hormone (α-MSH)-stimulated B16F10 cells. Quantitative real time PCR (qRT-PCR) demonstrated that treatment with (-)-4-hydroxysattabacin down-regulated several melanogenic genes, including tyrosinase, tyrosinase-related protein 1 (TRP-1), and tyrosinase-related protein 2 (TRP-2) while their enzymatic activities were unaffected. The anti-melanogenic effects of (-)-4-hydroxysattabacin were further demonstrated in a pigmented 3D human epidermal skin model, MelanodermTM, and manifested as whitening and regression of melanocyte activation in the tissue.
Asunto(s)
Organismos Acuáticos , Bacillus/metabolismo , Hexanonas/farmacología , Animales , Línea Celular Tumoral , Supervivencia Celular , Relación Dosis-Respuesta a Droga , Epidermis/efectos de los fármacos , Hexanonas/química , Hexanonas/metabolismo , Humanos , Levodopa/administración & dosificación , Levodopa/farmacología , Melaninas/metabolismo , Melanoma/metabolismo , Ratones , Estructura Molecular , Pigmentación/efectos de los fármacosRESUMEN
Chemical investigation of a marine-derived actinomycete isolated from marine sediments collected off the coast of southern California and identified as a Nocardiopsis sp. (strain CNQ115) led to the isolation of two new 4-aminoimidazole alkaloids, nocarimidazoles A (1) and B (2). The chemical structures of nocarimidazoles A and B were assigned by interpretation of NMR spectroscopic data and through methylation to yield monomethyl and dimethyl derivatives. Nocarimidazoles A and B possess a 4-aminoimidazole ring combined with a conjugated carbonyl side chain, which is rarely found in microbial secondary metabolites.
Asunto(s)
Actinomycetales/química , Alcaloides/aislamiento & purificación , Imidazoles/aislamiento & purificación , Alcaloides/química , Alcaloides/farmacología , Bacillus subtilis/efectos de los fármacos , California , Escherichia coli/efectos de los fármacos , Humanos , Imidazoles/química , Imidazoles/farmacología , Klebsiella pneumoniae/efectos de los fármacos , Biología Marina , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Salmonella typhimurium/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Staphylococcus epidermidis/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
Geraniol (1) is the biogenetic precursor of a number of monoterpenes. We tested various marine-derived microorganisms to determine their ability to biotransform 1. Only Hypocrea sp. was capable of transforming 1 into its oxidized derivative, 1,7-dihydroxy-3,7-dimethyl-(E)-oct- 2-ene (2). The structure of the metabolite obtained was assigned on the basis of detailed spectroscopic data analyses.
Asunto(s)
Hypocrea/metabolismo , Monoterpenos/metabolismo , Agua de Mar/microbiología , Terpenos/metabolismo , Monoterpenos Acíclicos , Biotransformación , Hypocrea/química , Hypocrea/aislamiento & purificación , Monoterpenos/química , Terpenos/químicaRESUMEN
A new 14-membered macrolactam natural product, fluvirucin B6 (1), was isolated from a marine-derived actinomycete, Nocardiopsis sp. CNQ-115, via HPLC-UV guided isolation. The chemical structure of 1 was elucidated by 1D and 2D NMR spectroscopic data analysis. Compound 1 showed a weak activity against Gram-positive bacteria, whereas it was inactive against Gram-negative bacteria.