RESUMO
Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
Assuntos
Cumarínicos/química , Glicosídeos , Rutaceae , Cumarínicos/isolamento & purificação , Glicosídeos/química , Glicosídeos/isolamento & purificação , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Rutaceae/químicaRESUMO
Bioactivity-driven LC/MS-based phytochemical analysis of the root bark extract of Ulmus davidiana var. japonica led to the isolation of 10 compounds including a new coumarin glycoside derivative, ulmusakidian (1). The structure of the new compound was elucidated using extensive spectroscopic analyses via 1D and 2D NMR spectroscopic data interpretations, HR-ESIMS, and chemical transformation. The isolated compounds 1-10 were tested for their antifungal activity against human fungal pathogens Cryptococcus neoformans and Candida albicans. Compounds 9 and 10 showed antifungal activity against C. neoformans, with the lowest minimal inhibitory concentration (MIC) of 12.5-25.0 µg/mL, whereas none of the compounds showed antifungal activity against C. albicans.
Assuntos
Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Ulmus/química , Antifúngicos/química , Antifúngicos/isolamento & purificação , Relação Dose-Resposta a Droga , Testes de Sensibilidade Microbiana , Estrutura Molecular , Fenóis/química , Fenóis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
A new prenylated coumarin diglycoside, 6-prenylcoumarin-7-O-ß-D-apiofuranosyl-(1â6)-ß-D-glucopyranoside (1) and five known flavonoid glycosides (2-6) were isolated from the leaves and stems of Clausena dunniana. The structures of these isolates were elucidated based on comprehensive MS, UV, IR, and NMR spectroscopic data analysis and comparison with the data reported in literature. Compounds 2-6 are obtained from the title plant for the first time. All these isolates were evaluated for their insulin-release promoting effects, and compounds 1, 2, and 4 exhibited significant activities (2.0 to 3.3-fold higher in comparison with the control, p < 0.01) at 40 µM.[Formula: see text].
Assuntos
Clausena , Insulinas , Cumarínicos/farmacologia , Glicosídeos/farmacologia , Estrutura MolecularRESUMO
Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
Assuntos
Cumarínicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Rutaceae/químicaRESUMO
Six new coumarin glycosides, genglycoside A-F (1-6), were isolated from the aerial parts of Gendarussa vulgaris, along with ten known analogues (7-16). Their structures were unambiguously established on the basis of extensive spectroscopic data and HPLC analysis. The cytotoxic activities of all isolated compounds were evaluated by MTT assay. Compound 12 showed the most potent cytotoxicity in Eca-109, MCF-7, and HepG2 cell lines. By the preliminary structure-activity relationships, it was firstly discovered that the glycosylation or esterification at 7,8-dihydroxy or 7-hydroxy drastically reduced the cytotoxic activity of the parent coumarin.
Assuntos
Antineoplásicos Fitogênicos , Cumarínicos , Glicosídeos , Lamiales/química , Componentes Aéreos da Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Cumarínicos/química , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Células MCF-7RESUMO
BACKGROUND: Water extract of Hydrangea paniculata (HP) stem, rich in coumarin glycosides, has been demonstrated to have renal protective effect in several experimental kidney injury animal models. Currently, it is under pre-clinical development as a class 5 herbal drug against membranous nephropathy. However, whether it also benefits diabetic nephropathy (DN) is not clear. PURPOSE: This study was performed to investigate the protective effect of HP on streptozotocin-induced experimental DN, and further understand its molecular mechanisms. METHODS: In the present study, type 1 diabetes rat model was established by the intraperitoneal injection of streptozotocin. HP was orally administered every day for three months. Biochemical analysis and histopathological staining were conducted to evaluate the renal functions. In vivo pharmacokinetic study was conducted to analyse the metabolites of HP with high blood drug concentration. In vitro assay using these metabolites was performed to analyse their ability to reduce reactive oxygen species (ROS) production induced under high glucose (HG) condition by flow cytometry. Reverse transcription-polymerase chain reaction was conducted to analyse the mRNA level of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) and IL6 and western blot was performed to analyse the phosphorylation status of smad 2/3 in HK2 cells under TGFß1 stimulation. RESULTS: The treatment with HP significantly reduced the blood urea nitrogen and serum creatinine content, and urine albumin excretion in diabetic rats, and increased the creatinine clearance rate. Periodic acid-schiff and methenamine staining and immunohistochemistry revealed that HP also ameliorated glomerulosclerosis and tubular vacuolar degeneration, as well as the deposition of fibronectin and collagen IV in the glomeruli. Pharmacokinetic study results revealed that the major coumarin compounds from HP were metabolised into umbelliferone and esculetin. By in vitro assay, umbelliferone and esculetin were found to significantly decrease ROS production induced by HG content, as well as increase the mRNA level of Nrf2. HP and its metabolites also can down-regulate fibronectin secretion in HK2 cells stimulated by TGFß1 and inhibit smad2/3 phosphorylation. CONCLUSION: HP has beneficial effect on DN by increasing Nrf2 expression and inhibiting TGF-smad signal activation. Further, it can be a novel herbal drug against DN.
Assuntos
Cumarínicos/farmacologia , Nefropatias Diabéticas/tratamento farmacológico , Hydrangea/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Cumarínicos/química , Diabetes Mellitus Experimental/complicações , Nefropatias Diabéticas/metabolismo , Nefropatias Diabéticas/patologia , Fibrose/tratamento farmacológico , Fibrose/patologia , Glicosídeos/química , Glicosídeos/farmacologia , Rim/efeitos dos fármacos , Rim/metabolismo , Rim/fisiologia , Terapia de Alvo Molecular/métodos , Fator 2 Relacionado a NF-E2/metabolismo , Extratos Vegetais/farmacocinética , Ratos , Ratos Wistar , Proteína Smad2/metabolismo , Proteína Smad3/metabolismo , Estreptozocina , Umbeliferonas/farmacocinéticaRESUMO
A new phenylpropanoid glycoside (1), and two new coumarin glycosides (2, 3), together with two known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 µM) exhibited significant hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays.
Assuntos
Cumarínicos/química , Glicosídeos/química , Hydrangea/química , Propanóis/química , Substâncias Protetoras/química , Acetaminofen/antagonistas & inibidores , Acetaminofen/toxicidade , Antipiréticos/antagonistas & inibidores , Antipiréticos/toxicidade , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Estrutura Molecular , Caules de Planta/química , Propanóis/isolamento & purificação , Propanóis/farmacologia , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Relação Estrutura-AtividadeRESUMO
Phytochemical investigation on the seeds of Herpetospermum caudigerum afforded two new coumarin glycosides A and B (1 and 2), together with a known compound herpetolide A (3). Their structures were determined by spectroscopic methods, including 2D NMR techniques. Compound 3 exhibited cytotoxicity against HepG2 cells with IC50 value of 6.47 µg/ml. Compound 2 showed anti-hepatitis B virus activity with HBsAg secretion by 33.1% at 200 µg/ml.
Assuntos
Antivirais/isolamento & purificação , Cumarínicos/isolamento & purificação , Cucurbitaceae/química , Glicosídeos/isolamento & purificação , Antivirais/química , Antivirais/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Células Hep G2 , Vírus da Hepatite B/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Sementes/químicaRESUMO
Object To study and identify the chemical constituents of Bombyx Batryticatus. Methods The constituents were isolated from the above materials by column chromatography using silica gel and Sephadex LH-20, purified by crystallization, and identified by spectroscopic methods. Results Eight compounds were isolated and identified. They are 6-methoxy-7-O-?-D-(4′-methoxy) glucopyranosyl coumarin (Ⅰ), ergost-6, 22-dien-3?, 5?, 8?-triol (Ⅱ), palmitic acid (Ⅲ), meso-erythritol (Ⅳ), D-mannitol (Ⅴ), uracil (Ⅵ), ?-sitosterol (Ⅶ), and daucosterol (Ⅷ). Conclusion Coumpound Ⅰ is a new coumarin glycoside.