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1.
Crit Rev Food Sci Nutr ; 60(3): 494-514, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-30582344

RESUMO

The tumor is becoming a critical threat to our lives in these years. Searching for antitumor substances from natural products is a great interest of scientists. Cudrania tricuspidata (C. tricuspidata) is a regional plant containing 158 flavonoids and 99 xanthones, and others ingredients with favorable bioactivity. This review comprehensively analyzes the antitumor compounds from C. tricuspidata against different tumors, and 78 flavonoids plus xanthones are considered as underlying antineoplastic. Importantly, the structure of preylation groups is the primary source of antitumor activity among 45 flavonoids plus xanthones, which could be a direction of structural modification for a better antitumor ability. Additionally, the fruits are also preferable sources of antitumor compounds compared to the roots and barks due to the abundant isoflavones and sustainability. However, many studies only focused on the cells viability inhibition of the compounds, the underlying molecular mechanisms, and the intracellular targets remain ambiguous. In conclusion, C. tricuspidata has a great potential for anti-tumor prevention or therapy, but more attention should be paid to deeper research in vitro and in vivo models.


Assuntos
Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Flavonoides/farmacologia , Moraceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Xantonas/farmacologia , Antineoplásicos/química , Flavonoides/isolamento & purificação , Frutas/química , Humanos , Xantonas/isolamento & purificação
2.
Chem Biodivers ; 17(2): e1900640, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31805214

RESUMO

The extract of the strain Aspergillus flavipes DL-11 exerted antibacterial activities against six Gram-positive bacteria. During the following bioassay-guided separation, ten diphenyl ethers (1-10), two benzophenones (11-12), together with two xanthones (13-14) were isolated. Among them, 4'-chloroasterric acid (1) was a new chlorinated diphenyl ether. Their structures were elucidated by extensive spectroscopic data analysis, including IR, HR-ESI-MS, NMR experiments, and by comparison with the literature data. All compounds showed moderate to strong antibacterial effects on different Gram-positive bacteria with MIC values that ranged from 3.13 to 50 µg/mL, but none of the compounds exhibited activity against Gram-negative bacteria Vibrio parahaemolyticus ATCC17802 (MIC>100 µg/mL). In particular, the MICs of some compounds are at the level of positive control.


Assuntos
Antibacterianos/química , Aspergillus/química , Benzofenonas/química , Éteres Fenílicos/química , Xantonas/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Aspergillus/metabolismo , Benzofenonas/isolamento & purificação , Benzofenonas/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Conformação Molecular , Éteres Fenílicos/isolamento & purificação , Éteres Fenílicos/farmacologia , Xantonas/isolamento & purificação , Xantonas/farmacologia
3.
Nat Prod Res ; 34(8): 1080-1090, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30663363

RESUMO

Isoshamixanthone (1), a new stereoisomeric pyrano xanthone together with the previously known fungal metabolites, epiisoshamixanthone (2), sterigmatocystin (3), arugosin C (4), norlichexanthone (5), diorcinol (6), ergosterol and methyllinoleate, were obtained from the endophytic fungal strain Aspergillus sp. ASCLA isolated from leaf tissues of the medicinal plant Callistemon subulatus. The chemical structure of the new xanthone (1) was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data. The constitutions and absolute configurations of 1 and epiisoshamixanthone (2) were additionally confirmed by X-ray crystallography. Compounds 1,2 were evaluated for their potential anticancer activity using the human cervix carcinoma cell line (KB-3-1). The antimicrobial activities of the fungal extract and compounds 1,2 were studied using a panel of pathogenic microorganisms as well.


Assuntos
Aspergillus/química , Plantas Medicinais/microbiologia , Xantonas/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Aspergillus/isolamento & purificação , Linhagem Celular Tumoral , Cristalografia por Raios X , Ergosterol , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Estrutura Molecular
4.
Chem Pharm Bull (Tokyo) ; 67(11): 1242-1247, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31685751

RESUMO

Polygalaxanthone III, a xanthone glycoside that is a major constituent of "Polygala Root" (Polygala tenuifolia roots, Onji in the Japanese Pharmacopoeia), has been used as a standard in the quality control of crude drugs. However, we previously noted differences in the chromatographic properties of one of three samples of polygalaxanthone III. Therefore, standardization of the standard itself is extremely important. The structures of three standard samples commercially available as polygalaxanthone III were characterized by LC/MS and NMR. LC/MS analysis revealed that two molecular types exist. Both types are chromatographically separable but have an identical mass number with distinguishable MS/MS spectra. One dimensional (1D)-NMR analyses demonstrated that both had the same xanthone moiety and heteronuclear multiple bond correlation (HMBC) analyses revealed that they are structural isomers at the connecting position of glucose to apiose 1-position. Consequently, the isomers were identified as polygalaxanthone III and its regioisomer, polygalaxanthone XI. Based on the findings, we recommend using the LC-MS/MS detection method, which discriminates polygalaxanthone III and XI, to confirm the quality of the standard.


Assuntos
Glicosídeos/química , Raízes de Plantas/química , Polygala/química , Xantonas/química , Glicosídeos/isolamento & purificação , Estrutura Molecular , Xantonas/isolamento & purificação
5.
Int J Mol Sci ; 20(19)2019 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-31569691

RESUMO

Xanthones are important chemical constituents of Garcinia xanthochymus and varied bioactivities including cytotoxicity. However, their anti-tumor mechanism has remained unknown. Here, we isolated and identified a new xanthone named garciniaxanthone I (1) and five known compounds from the bark of G. xanthochymus. Their structures were elucidated by NMR analysis and HRESIMS. The anti-proliferation activities of all isolated compounds were evaluated on four human tumor cell lines (HepG2, A549, SGC7901, MCF-7). The results demonstrated that the anti-proliferation activity of xanthone was related to the number and location of prenyl groups. We further found that garciniaxanthone I (GXI) could induce HepG2 apoptosis and enhance the expression of cleaved caspase-8, caspase-9, and caspase-3. GXI could also increase Bax level and concurrently reduce the overexpression of Bcl-2, Bcl-XL, Mcl-1, and surviving in HepG2 cells. Moreover, GXI could inhibit cell migration of HepG2 cells by inhibiting the expressions of MMP-7 and MMP-9. In summary, our study suggests that GXI could induce HepG2 apoptosis via the mitochondrial pathway and might become a lead compound for liver cancer treatment.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Garcinia/química , Mitocôndrias/efeitos dos fármacos , Casca de Planta/química , Extratos Vegetais/farmacologia , Xantonas/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Mitocôndrias/metabolismo , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Transdução de Sinais/efeitos dos fármacos , Xantonas/química , Xantonas/isolamento & purificação
6.
J Enzyme Inhib Med Chem ; 34(1): 1623-1632, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31480857

RESUMO

This study aimed to search the α-glucosidase inhibitors from the barks part of Artocarpus elasticus. The responsible compounds for α-glucosidase inhibition were found out as dihydrobenzoxanthones (1-4) and alkylated flavones (5-6). All compounds showed a significant enzyme inhibition toward α-glucosidase with IC50s of 7.6-25.4 µM. Dihydrobenzoxanthones (1-4) exhibited a competitive inhibition to α-glucosidase. This competitive behaviour was fully characterised by double reciprocal plots, Yang's method, and time-dependent experiments. The compound 1 manifested as the competitive and reversible simple slow-binding, with kinetic parameters k3 = 0.0437 µM-1 min-1, k4 = 0.0166 min-1, and Kiapp = 0.3795 µM. Alkylated flavones (5-6) were mixed type I (KI < KIS) inhibitors. The binding affinities (KSV) represented by all inhibitors were correlated to their concentrations and inhibitory potencies (IC50). Moreover, compounds 1 and 5 were identified as new ones named as artoindonesianin W and artoflavone B, respectively. Molecular modelling study proposed the putative binding conformation of competitive inhibitors (1-4) to α-glucosidase at the atomic level.


Assuntos
Artocarpus/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Casca de Planta/química , Xantonas/farmacologia , alfa-Glucosidases/metabolismo , Relação Dose-Resposta a Droga , Fluorescência , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificação
7.
Eur J Med Chem ; 181: 111536, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31376561

RESUMO

Nine new and unique xanthone derivatives, including one novel hybrid monoterpene-tetrahydroxanthone (1), three dihydro-xanthone derivatives (2-4), and five skeleton-rearranged xanthone derivatives (5-9), were obtained from a 95% EtOH extract of Garcinia oligantha leaves by a LC-MS-guided fractionation procedure. The structures of the new compounds were elucidated by analysis of their 1D and 2D NMR and MS data. The relative configurations of 2 and 8 were determined via X-ray crystallographic data analysis, while the absolute configurations of 1-2, 5-9 were assigned based on a comparison of calculated and experimental ECD and/or OR data. In SRB, PI-exclusion and Hoechst staining assays, 6 showed strong cytotoxic activities which could dose-dependently induce Taxol-insensitive quiescent LNCaP cell death. Additionally, a preliminary mechanism investigation using immunoblotting and Caspase-3 activity assay, indicated that 6 induced quiescent LNCaP cell death potentially through caspase-dependent mitochondrial apoptosis pathway.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Inibidores Enzimáticos/farmacologia , Garcinia/química , Folhas de Planta/química , Xantonas/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Caspase 3/metabolismo , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Estrutura Molecular , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificação
8.
Fitoterapia ; 138: 104286, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31394164

RESUMO

Three new compounds including two depsidones (simplicildones J and K) and one dihydroxanthenone (globosuxanthone E) together with nine known compounds were obtained from the crude extracts of two endophytic fungi Simplicillium lanosoniveum (J.F.H. Beyma) Zare & W. Gams PSU-H168 and PSU-H261 which were isolated from the leaves of Hevea brasiliensis. The structures were elucidated by spectroscopic evidence. The absolute configuration of globosuxanthone E was established by means of experimental and calculated TDDFT ECD data. Simplicildone K exhibited antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with equal MIC values of 128 µg/mL. Simplicildone K and globosuxanthone E displayed antifungal activity against Cryptococcus neoformans ATCC90113 with the same MIC values of 32 µg/mL. In addition, known botryohordine C and simplicildone A showed phosphodiesterase 5 inhibitory activity with the IC50 values of 5.69 and 9.96 µM, respectively, and were noncytotoxic toward noncancerous Vero cells.


Assuntos
Depsídeos/farmacologia , Hevea/microbiologia , Hypocreales/química , Lactonas/farmacologia , Xantonas/farmacologia , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Chlorocebus aethiops , Cryptococcus neoformans/efeitos dos fármacos , Depsídeos/isolamento & purificação , Endófitos/química , Lactonas/isolamento & purificação , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Inibidores da Fosfodiesterase 5/isolamento & purificação , Inibidores da Fosfodiesterase 5/farmacologia , Folhas de Planta/microbiologia , Tailândia , Células Vero , Xantonas/isolamento & purificação
9.
Chem Biodivers ; 16(9): e1900353, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31329336

RESUMO

Five known secondary metabolites, chrysophanol (1), 7,7'-biphyscion (2), secalonic acid D (3), mannitol (4) and trehalose (5) were isolated for the first time from the extracts of the fungus Phialomyces macrosporus. Their structures were elucidated by NMR methods (1D and 2D NMR analysis), optical activity and ESI-MS. Complete 1 H and 13 C assignments were performed for compound 2. The antimicrobial activity was evaluated by serial microdilution assay for compounds 2 and 3 and results showed that compound 3 exhibited a significant growth inhibition at concentrations of 15.6 mg/ml (S. aureus and S. choleraesius) and 0.97 mg/mL (B. subtilis), comparable to the positive control.


Assuntos
Antibacterianos/farmacologia , Bacillus subtilis/efeitos dos fármacos , Salmonella/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Antraquinonas/química , Antraquinonas/isolamento & purificação , Antraquinonas/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Bacillus subtilis/crescimento & desenvolvimento , Relação Dose-Resposta a Droga , Espectroscopia de Ressonância Magnética , Manitol/química , Manitol/isolamento & purificação , Manitol/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Salmonella/crescimento & desenvolvimento , Staphylococcus aureus/crescimento & desenvolvimento , Trealose/química , Trealose/isolamento & purificação , Trealose/farmacologia , Xantonas/química , Xantonas/isolamento & purificação , Xantonas/farmacologia
10.
Fitoterapia ; 137: 104194, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31175954

RESUMO

Four unusual heterodimeric tetrahydroxanthones, usneaxanthones A-D (1-4) were isolated from lichen Usnea aciculifera Vain (Parmeliaceae). Their structures and absolute configurations, particularly the central and axial chiralities, were unambiguously demonstrated by a combination of spectroscopic data (1D, 2D NMR, HRESIMS), electronic circular dichroism (ECD) experiments, and single-crystal X-ray crystallographic analyses. Cytotoxic effects of isolated compounds (1, 2 and 4) were evaluated on HT-29 human colorectal cancer cells. Compound 4 showed potent cytotoxicity against HT-29 with IC50 values of 2.41 µM.


Assuntos
Antineoplásicos/farmacologia , Usnea/química , Xantonas/farmacologia , Antineoplásicos/isolamento & purificação , Células HT29 , Humanos , Estrutura Molecular , Vietnã , Xantonas/isolamento & purificação
11.
Food Chem ; 292: 121-128, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31054655

RESUMO

Ultrafiltration of Cyclopia genistoides extract was optimised to increase its benzophenone and xanthone content as quantified using HPLC-DAD. Regenerated cellulose (RC) and polyethersulphone membranes with molecular weight cut-offs of 10 and 30 kDa were evaluated in terms of compound enrichment, permeate flux and permeate yield, using dead-end ultrafiltration. Compound enrichment was subsequently optimised using the 10 kDa RC membrane and tangential flow ultrafiltration (TFU). The effect of extract composition on compound enrichment, due to natural variation in the source material, was assessed using extracts from different batches of plant material (n = 11). Transmembrane pressure and feed flow rate affected (p < 0.05) process efficiency (mean permeate flux, compound enrichment and membrane fouling). TFU achieved ≥20% enrichment of the target compounds, proving its suitability for preparation of a nutraceutical extract of C. genistoides.


Assuntos
Benzofenonas/análise , Fabaceae/metabolismo , Extratos Vegetais/química , Ultrafiltração/métodos , Xantonas/análise , Benzofenonas/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Membranas Artificiais , Xantonas/isolamento & purificação
12.
Life Sci ; 223: 174-184, 2019 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-30890405

RESUMO

AIM: Atherosclerosis (AS) is a chronic condition of the arterial vessels and a risk factor for myocardial infarction and stroke. Euxanthone is a xanthone compound extracted from Polygala caudata, and shows vasodilatory action. The aim of this study was to determine the potential pharmacological effects of euxanthone against oxidized low-density lipoprotein (ox-LDL)-induced endothelial cell injury. MATERIAL AND METHODS: Human umbilical vein endothelial cells (HUVECs) were exposed to ox-LDL, following pre-treatment with different concentrations of euxanthone. Viability, apoptosis and DNA fragmentation were respectively assessed by CCK-8 assay, Annexin-V/PI staining and TdT-mediated dUTP Nick-End Labeling (TUNEL) assay. The cellular levels of malondialdehyde (MDA), superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px) were analyzed by enzyme linked immune-sorbent assays (ELISA), and reactive oxygen species (ROS) levels using dichlorodihydrofluorescin diacetate (DCFH) staining. Quantitative RT-PCR and Western blotting were respectively used to analyze the expression levels of specific mRNAs and proteins. HUVECs were transfected with Nrf2 siRNA to induce knockdown of the latter. KEY FINDINGS: Euxanthone pre-treatment rescued the HUVECs from ox-LDL-induced cytotoxicity, apoptosis and DNA fragmentation in a dose-dependent manner. In addition, euxanthone also significantly reversed ox-LDL-triggered loss of mitochondrial membrane potential (MMP), cytochrome C release from mitochondria to cytosol, cleavage of caspase-3 and PARP, and increase in Bax/Bcl-2 ratio. Pre-treatment with euxanthone markedly suppressed ox-LDL-induced ROS generation and inhibition of antioxidant enzymes, as well as the up-regulation of pro-inflammatory factors like MCP-1, IL-1ß and TNF-α in the HUVECs. Euxanthone up-regulated and activated Nrf2 by repressing Keap1, and increased the expression of its downstream genes HO-1 and NQO-1. Nrf2 knockdown abrogated the cyto-protective, anti-apoptotic, anti-oxidant and anti-inflammatory effects of euxanthone in ox-LDL-treated HUVECs. Finally, euxanthone activated Nrf2 via the MAPK pathway and blocking the latter likewise negated the protective effects of euxanthone against cell ox-LDL. SIGNIFICANCE: Euxanthone protected HUVECs against the oxidative and inflammatory damage induced by ox-LDL, indicating its potential as a novel therapeutic agent for AS.


Assuntos
Anti-Inflamatórios/farmacologia , Apoptose/efeitos dos fármacos , Lipoproteínas LDL/toxicidade , Fator 2 Relacionado a NF-E2/metabolismo , Xantonas/farmacologia , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/metabolismo , Técnicas de Cultura de Células , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Células Endoteliais da Veia Umbilical Humana , Humanos , Marcação In Situ das Extremidades Cortadas , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Polygala/química , Xantonas/isolamento & purificação
13.
Biosci Biotechnol Biochem ; 83(6): 996-999, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30835638

RESUMO

Endolichenic fungi, nonobligate microfungi that live in lichen, are promising as new bioresources of pharmacological compounds. We found that norlichexanthone isolated from the endolichenic fungus in Pertusaria laeviganda exhibited high antioxidant activity. Norlichexanthone produced by endolichenic fungus had the antioxidant activity with same level of ascorbic acid. This is the first report of high antioxidant activity of norlichexanthone. Abbreviations: AAPH: 2,2'-azobis (2-methylpropionamidine) dihydrochloride; DPPH: 2,2-diphenyl-1-picrylhydrazyl; FL: fluorescein sodium salt; HPLC-PDA: high-performance liquid chromatography with photodiode array; LC-ESI-MS: liquid chromatography with electrospray ionization mass spectrometry; ORAC: oxygen radical absorbance capacity; PB: phosphate buffer; ROS: reactive oxygen species; TLC: thin-layer chromatography.


Assuntos
Antioxidantes/farmacologia , Ascomicetos/metabolismo , Líquens/microbiologia , Xantonas/metabolismo , Xantonas/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia em Camada Delgada/métodos , Análise Espectral/métodos , Xantonas/isolamento & purificação
14.
Curr Pharm Biotechnol ; 20(3): 215-221, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30848197

RESUMO

BACKGROUND: Herpes simplex virus (HSV) and poliovirus (PV) are both agents of major concern in the public health system. It has been shown that Dimorphandra gardneriana galactomannans can be used as solubilizer vehicles in the manufacturing of medicine. Mangiferin is the major constituent of Mangifera indica and presents multiple medicinal and biological activities. OBJECTIVE: This study assayed the effect of D. gardneriana galactomannan combined with mangiferin (DgGmM) against HSV-1 and PV-1. METHODS: The DgGmM cytotoxicity was evaluated by the colorimetric MTT method and the antiviral activity by plaque reduction assay, immunofluorescence and polymerase chain reaction (PCR), in HEp-2 cells. RESULTS: The DgGmM showed a 50% cytotoxic concentration (CC50) > 2000 µg/mL. The 50% inhibitory concentrations (IC50) for HSV-1 and PV-1 were, respectively, 287.5 µg/mL and 206.2 µg/mL, with selectivity indexes (SI) > 6.95 for the former and > 9.69 for the latter. The DgGmM time-ofaddition protocol for HSV-1 showed a maximum inhibition at 500 µg/mL, when added concomitantly to infection and at the time 1 h post-infection (pi). While for PV-1, for the same protocol, the greatest inhibition, was also observed concomitantly to infection at 500 µg/mL and at the times 4 h and 8 h pi. The inhibition was also demonstrated by the decrease of fluorescent cells and/or the inhibition of specific viral genome. CONCLUSION: These results suggested that the DgGmM inhibited HSV-1 and PV-1 replication, with low cytotoxicity and high selectivity and, therefore, represents a potential candidate for further studies on the control of herpes and polio infections.


Assuntos
Antivirais/administração & dosagem , Herpesvirus Humano 1/efeitos dos fármacos , Mananas/administração & dosagem , Extratos Vegetais/administração & dosagem , Xantonas/administração & dosagem , Antivirais/isolamento & purificação , Relação Dose-Resposta a Droga , Quimioterapia Combinada , Células Hep G2 , Herpes Simples/tratamento farmacológico , Herpesvirus Humano 1/fisiologia , Humanos , Mananas/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Poliovirus/efeitos dos fármacos , Replicação Viral/efeitos dos fármacos , Replicação Viral/fisiologia , Xantonas/isolamento & purificação
15.
J Pharm Pharmacol ; 71(6): 1017-1028, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30847938

RESUMO

OBJECTIVES: Investigating the antipulmonary fibrosis effect of mangiferin from Mangifera indica and the possible molecular mechanism. METHODS: In vivo, bleomycin (BLM)-induced pulmonary fibrosis experimental model was used for evaluating antipulmonary fibrosis effect of mangiferin. Histopathologic examination and collagen deposition were investigated by HE and Masson staining as well as detecting the content of hydroxyproline. The expression of transforming growth factor-ß1 (TGF-ß1), α-smooth muscle actin (α-SMA), TLR4 and p-P65 in lung tissue was analysed through immunofluorescence. Leucocytes and inflammatory cytokines including IL-1ß, IL-6, TNF-α and MCP-1 in bronchoalveolar lavage fluid were detected by cell counting and enzyme-linked immunosorbent assay. In vitro, TGF-ß1-induced A549 epithelial-mesenchymal transition (EMT) cell model was used for investigating the possible molecular mechanism. Reactive oxygen species (ROS) generation was detected by DCFH-DA assay. Expression of all proteins was examined by Western blot. KEY FINDINGS: Oral administration of mangiferin could attenuate the severity of BLM-induced pulmonary fibrosis through increasing the survival rate, improving histopathological lesion and body weight loss as well as decreasing pulmonary index visibly. Pulmonary hydroxyproline content, TGF-ß1, and α-SMA levels were reduced significantly. The molecular mechanism of mangiferin for inhibiting pulmonary fibrosis is that it could obviously inhibit the occurrence of inflammation and the secretion of inflammatory cytokine through inhibiting activation of TLR4 and phosphorylation of p65. Meanwhile, EMT process was suppressed obviously by mangiferin through blocking the phosphorylation of Smad2/3 and reducing MMP-9 expression. Besides, mangiferin could significantly inhibit the process of oxidant stress through downregulating the intracellular ROS generation. CONCLUSIONS: Mangiferin attenuates BLM-induced pulmonary fibrosis in mice through inhibiting TLR4/p65 and TGF-ß1/Smad2/3 pathway.


Assuntos
Mangifera/classificação , Estresse Oxidativo/efeitos dos fármacos , Fibrose Pulmonar/prevenção & controle , Xantonas/farmacologia , Células A549 , Animais , Bleomicina/toxicidade , Líquido da Lavagem Broncoalveolar , Colágeno/metabolismo , Citocinas/metabolismo , Modelos Animais de Doenças , Transição Epitelial-Mesenquimal/efeitos dos fármacos , Feminino , Humanos , Masculino , Camundongos , Espécies Reativas de Oxigênio/metabolismo , Proteína Smad2/metabolismo , Proteína Smad3/metabolismo , Receptor 4 Toll-Like/metabolismo , Fator de Transcrição RelA/metabolismo , Fator de Crescimento Transformador beta1/metabolismo , Xantonas/isolamento & purificação
16.
Planta Med ; 85(6): 444-452, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30650454

RESUMO

Six new prenylated xanthones (1: -6: ) and seventeen known xanthones were isolated from extracts of Garcinia bracteata leaves. Their structures were determined by extensive NMR and MS spectroscopic data analysis. The inhibitory activities of the isolates were assayed on HeLa, A549, PC-3, HT-29, and WPMY-1 cell lines. Compounds 1: and 15: -17: showed moderate inhibitory effects on tumor cell growth, with IC50s ranging from 3.7 to 14.7 µM.


Assuntos
Citotoxinas/isolamento & purificação , Garcinia/química , Folhas de Planta/química , Xantonas/isolamento & purificação , Linhagem Celular Tumoral/efeitos dos fármacos , Citotoxinas/farmacologia , Células HeLa/efeitos dos fármacos , Humanos , Células PC-3/efeitos dos fármacos , Relação Estrutura-Atividade , Xantonas/farmacologia
17.
Nat Prod Res ; 33(20): 2982-2987, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30488728

RESUMO

A new xanthone glycoside, 3,5,7,8-tetramethoxyxanthone-1-O-ß-D-glucopyranoside (1), along with five known compounds, mangiferin (2), kaempferol (3), quercetin (4), chlorogenic acid (5) and diploptene (6), was isolated from the whole plants of Pyrrosia sheareri (Bak.) Ching. The structure of compound 1 was established on the basis of extensive spectroscopic analyses and chemical methods.


Assuntos
Glicosídeos/isolamento & purificação , Polypodiaceae/química , Xantonas/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/química , Quempferóis/isolamento & purificação , Estrutura Molecular , Quercetina/isolamento & purificação , Análise Espectral , Triterpenos/isolamento & purificação , Xantonas/química
18.
J Antibiot (Tokyo) ; 72(1): 34-44, 2019 01.
Artigo em Inglês | MEDLINE | ID: mdl-30258223

RESUMO

4,4'-bond secalonic acid D (4,4'-SAD) is a known compound isolated from the marine-derived fungus Penicillium oxalicum. No study about the antitumor effect of this compound has been reported, except for a few focusing on its bactericidal properties. Herein, we performed an in vitro biology test and found that 4,4'-SAD stimulated the apoptosis of tumor cells in the human hepatocellular carcinoma cell lines PLC/PRF/5 and HuH-7 by activating caspase-3, caspase-8, caspase-9, PARP, p53, and cyclin B1, as well as by regulating the Bax/Bcl-2 ratio. In vivo studies showed that 4,4'-SAD had antitumor efficacy in H22 cell xenograft model. Immunohistochemical analysis revealed that 4,4'-SAD could regulate Bax expression, which is a biomarker of tumor growth. In summary, 4,4'-SAD significantly inhibited tumor growth both in vivo and in vitro.


Assuntos
Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Organismos Aquáticos/química , Hepatócitos/efeitos dos fármacos , Penicillium/química , Xantonas/isolamento & purificação , Xantonas/farmacologia , Apoptose , Organismos Aquáticos/isolamento & purificação , Biomarcadores Tumorais/análise , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Hepatócitos/fisiologia , Humanos , Imuno-Histoquímica , Penicillium/isolamento & purificação , Proteína X Associada a bcl-2/análise
19.
Fitoterapia ; 132: 22-25, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30056184

RESUMO

Two undescribed piperidine racemates, (±)-caulophines A and B (1 and 2), a new N-containing xanthone derivative (3), together with six known piperidines, were isolated from the roots of Caulophyllum robustum Maxim. Their structures were determined by extensive spectroscopic techniques. Compounds 3 and 7 exhibited weak cytotoxicities against human palace cancer hela cell line with inhibitory rates of 32.2% and 39.7%, respectively, at the concentration of 40 µM.


Assuntos
Alcaloides/química , Caulophyllum/química , Piperidinas/química , Xantonas/química , Alcaloides/isolamento & purificação , China , Células HeLa , Humanos , Estrutura Molecular , Piperidinas/isolamento & purificação , Raízes de Plantas/química , Xantonas/isolamento & purificação
20.
Bioorg Chem ; 82: 274-283, 2019 02.
Artigo em Inglês | MEDLINE | ID: mdl-30396061

RESUMO

Four pairs of previously undescribed caged xanthones (1-4) and twelve known caged xanthones (5-16) were isolated from the leaf extract of Garcinia bracteata. Their structures were unambiguously elucidated on the basis of spectroscopic methods. The planar structure and relative configuration of 1 was confirmed by X-ray crystallographic analysis. The enantiomers of compounds 1, 2, 4 were further resolved by semi-preparative chiral HPLC, and the absolute configurations of enantiomers of compounds 1 and 4 were determined by measurement and calculation of electronic circular dichroism (ECD) spectra and specific rotations. The inhibitory activities of the isolated compounds against human HeLa, A549, PC-3, HT-29, and WPMY-1 cell lines were assayed, and garcibractatin A (4) showed the most potent inhibitory activities in vitro with IC50 values from 1.11 to 2.93 µM. A preliminary structure-activity relationship has been discussed, and some helpful conclusions have been drawn.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Garcinia/química , Folhas de Planta/química , Xantonas/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Humanos , Estereoisomerismo , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificação
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