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1.
Food Chem ; 308: 125666, 2020 Mar 05.
Artigo em Inglês | MEDLINE | ID: mdl-31655481

RESUMO

Nine new compounds, argutinosides A-I (1-9) together with 20 known compounds (10-29), were isolated from the fruits of Actinidia arguta. Using spectral analysis, the structures of the isolated compounds were identified as 10 succinic acid derivatives, 11 quinic acid derivatives, two shikimic acid derivatives and six citric acid derivatives. The NF-κB transcriptional inhibitory activity of the compounds was evaluated using RAW 264.7 macrophages cells induced by lipopolysaccharide. Among four groups of different organic acid derivatives, the quinic acid derivatives inhibited NF-κB transcriptional activity with an IC50 value of 4.0 µM. Fruit is rich in organic acid and secondary metabolites, which differ depending on the type of fruit. Our present study showed the presence of various organic acids conjugates including nine new 2-methylsuccinic acid phenolic conjugates in kiwiberry and compared their biological activities. This will contribute to application of kiwiberry and also the diversity of different fruits.


Assuntos
Actinidia/química , NF-kappa B/antagonistas & inibidores , Fenóis/farmacologia , Ácido Quínico/química , Animais , Linhagem Celular , Frutas/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Fenóis/química
2.
Bioorg Chem ; 92: 103234, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31479985

RESUMO

Nine new xanthones, cudracuspixanthones I - Q (12-14, 25, 32-36), and 30 known xanthones (1-11, 15-24, 26-31, 37-39) were isolated from the stems of Cudrania tricuspidata (Moraceae). The structures of isolated compounds were established by using 1D and 2D NMR in combination with HR-TOF-MS. Xanthones from the stems of C. tricuspidata exerted pancreatic lipase inhibitory activity. In addition, cudracuspixanthone P (35), a new xanthone, reduced the fat accumulation in liver cells stimulated with fatty acids. Therefore, these compounds might be beneficial in the treatment of metabolic diseases.

3.
Bioorg Chem ; 81: 127-133, 2018 12.
Artigo em Inglês | MEDLINE | ID: mdl-30118984

RESUMO

Eighteen constituents, including nine new compounds, were isolated from the bee pollen of Quercus mongolica. The structures of the new compounds were established on the basis of combined spectroscopic analysis. Structurally, the nine new compounds are polyamine derivatives with phenolic moieties which were assigned as one putrescine derivative, mogolicine A (2), seven spermidine derivatives, mongolidines A-G (3-5, 8, 12, 14, 17) and one spermine derivative, mogoline A (18). Evaluation of the biological activity of isolated compounds revealed that the polyamine derivatives with coumaroyl and caffeoyl moieties showed tyrosinase inhibition with IC50 values of 19.5-85.8 µM; however, the addition of a methoxy group to phenolic derivatives reduced the inhibitory activity.


Assuntos
Inibidores Enzimáticos/farmacologia , Monofenol Mono-Oxigenase/antagonistas & inibidores , Pólen/química , Poliaminas/farmacologia , Quercus/química , Animais , Abelhas , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Estrutura Molecular , Monofenol Mono-Oxigenase/metabolismo , Poliaminas/química , Poliaminas/isolamento & purificação , Relação Estrutura-Atividade
4.
J Nat Med ; 72(1): 155-160, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-28823078

RESUMO

Melanin, a dark macromolecular pigment, protects skin from harmful damage. However, abnormal accumulation is responsible for hyperpigmentation disorders. Melanogenesis inhibitors have therefore become important constituents in cosmetic products for depigmentation. Torilis japonica Decandolle (Umbelliferae) is a biennial plant which is distributed in East Asia. Fruits of this plant have been used for the treatment of skin disease and inflammation. In our previous study, torilin, a major sesquiterpene of T. japonica, showed an inhibitory effect on melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Further extensive chromatographic separation resulted in thirteen compounds. On the basis of spectroscopic analysis, the structures of the compounds isolated were determined to be three new sesquiterpenes, viz. a guaiane-type, epoxytorilinol (1), a eudesmane-type, elematorilone (2) and a cadinane-type, cardinatoriloside (3), together with ten known sesquiterpenes (4-13). Of the compounds isolated, compounds 4-6 and 11-13 inhibited α-MSH-activated melanin production in B16 melanoma cells with IC50 values from 72.9 to 191.0 µM.


Assuntos
Frutas/química , Melaninas/metabolismo , Melanoma Experimental/tratamento farmacológico , Extratos Vegetais/química , Sesquiterpenos/química , Animais , Melaninas/biossíntese , Camundongos
5.
Biosci Biotechnol Biochem ; 81(10): 1973-1977, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28828930

RESUMO

Efficient preparation of loganin from Cornus officinalis fruits was investigated. First, effect of extraction conditions on loganin yield was measured. The loganin content in C. officinalis extract was greatly affected by ethanol concentration and extraction time whereas extraction temperature exerted relatively little effect. Response surface methodology with Box-Behnken design suggested optimized extraction condition for maximum loganin yield as ethanol concentration, 32.0%; temperature 46.2 °C and extraction time, 46.7 min, which yielded 10.4 µg loganin/mg dried fruit. Next, the effect of maturation stage of C. officinalis fruits on loganin content was investigated. The loganin content in the extract of C. officinalis fruits was decreased as the maturation process. The loganin content in the unripe fruits was 18.0 µg/mg extract whereas reduced to 13.3 µg/mg extract for ripe fruits. Taken together, our present study suggested the importance of extraction condition and maturation stages for efficient preparation of loganin from C. officinalis fruits.


Assuntos
Fracionamento Químico/métodos , Cornus/metabolismo , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Iridoides/isolamento & purificação , Iridoides/metabolismo , Cornus/crescimento & desenvolvimento
6.
Molecules ; 22(8)2017 Aug 14.
Artigo em Inglês | MEDLINE | ID: mdl-28805750

RESUMO

In this study, the characterization of chemical constituents and biological activity of the roots of Taraxacum coreanum (Asteraceae) was attempted. Phytochemical investigation of the roots of T. coreanum led to the isolation of two new inositol derivatives, taraxinositols A (1) and B (2), and a new phenolic compound, taraxinol (16), together with twenty known compounds including four inositol derivatives, neo-inositol-1,4-bis (4-hydroxybenzeneacetate) (3), chiro-inositol-1,5-bis(4- hydroxybenzeneacetate) (4), chiro-inositol-2,3-bis (4-hydroxybenzeneacetate) (5) and chiro-inositol- 1,2,3-tris (4-hydroxybenzeneacetate) (6), nine phenolic compounds: p-hydroxybenzaldehyde (7), vanillin (8), syringaldehyde (9), vanillic acid (10), 4-methoxyphenylacetic acid (11), 4-hydroxy- phenylacetic acid methyl ester (12), optivanin (13), isoferulic acid (14) and dihydroconiferyl alcohol (15), four coumarins: nodakenetin (17), decursinol (18), prangol (19) and isobyakangelicin (20), and three lignans: syringaresinol-4'-O-ß-d-glucoside (21), syringaresinol (22), and pinoresinol (23). The structures of isolated compounds were determined on the basis of spectroscopic analysis. Among the isolated compounds, vanillic acid, isoferulic acid and syringaresinol showed radical scavenging activity with IC50 values ranging from 30.4 to 75.2 µM.


Assuntos
Inositol/química , Fenol/química , Extratos Vegetais/química , Raízes de Plantas/química , Taraxacum/química , Antioxidantes/química , Antioxidantes/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Cumarínicos/química , Furanos/química , Glucosídeos/química , Humanos , Concentração Inibidora 50 , Inositol/isolamento & purificação , Lignanas/química , Espectroscopia de Ressonância Magnética/métodos , Fenol/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Receptores Depuradores/química , Receptores Depuradores/metabolismo
7.
PLoS One ; 12(3): e0172069, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28253267

RESUMO

The composition and content of the active constituents and their biological activity vary according to diverse factors including their maturation stages. A previous study showed that the fruits of Cudrania tricuspidata inhibited pancreatic lipase activity, a key enzyme in fat absorption. In this study, we investigated the chemical composition and pancreatic lipase inhibitory activity of unripe and ripe fruits of C. tricuspidata. Unripe fruits of C. tricuspidata have a higher content of total phenolic and flavonoids and exhibited stronger pancreatic lipase inhibition compared to ripe fruits. HPLC analysis revealed the different chemical compositions of the unripe and ripe fruits. Further fractionation resulted in the isolation of 30 compounds including two new isoflavonoids. Analysis of the chemical constituents of the unripe and ripe fruits revealed that a 2,2-dimethylpyran ring, a cyclized prenyl, was the predominant side chain in the unripe fruits, whereas it was a linear prenyl group in the ripe fruits. In addition, a new isoflavonoid (19) from the unripe fruits showed the most potent inhibition on pancreatic lipase. Taken together, the maturation stage is an important factor for maximum efficacy and that unripe fruits of C. tricuspidata are a good source of new bioactive constituents for the regulation of obesity.


Assuntos
Inibidores Enzimáticos/farmacologia , Flavonoides/farmacologia , Frutas/química , Frutas/crescimento & desenvolvimento , Lipase/antagonistas & inibidores , Maclura/química , Pâncreas/enzimologia , Animais , Inibidores Enzimáticos/isolamento & purificação , Flavonoides/isolamento & purificação , Maclura/crescimento & desenvolvimento , Suínos
8.
Arch Pharm (Weinheim) ; 350(1)2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-27902844

RESUMO

Investigation of the CH2 Cl2 and EtOAc-soluble fractions of the roots of Cudrania tricuspidata afforded 31 compounds. The structures of the isolated compounds were determined on the basis of spectroscopic data interpretation such as 1D and 2D NMR analysis and elucidated as xanthones with prenyl moieties including four simple xanthones (1-4), five prenylated xanthones with one prenyl moiety (5-7, 20, and 21), and 22 prenylated xanthones with two prenyl moieties (8-19 and 22-31). Among them, three diprenylated xanthones named cudracuspixanthones E-G (16, 29, and 31) were first isolated in nature. Xanthones 2, 5, 6, 12, 19, 21, 22, 25, 27, and 28 showed moderate inhibition of lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 cells, with IC50 values ranging from 16.1 to 24.8 µM.


Assuntos
Lipopolissacarídeos/antagonistas & inibidores , Moraceae/química , Óxido Nítrico/biossíntese , Raízes de Plantas/química , Xantonas/isolamento & purificação , Xantonas/farmacologia , Animais , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Prenilação , Células RAW 264.7/metabolismo , Relação Estrutura-Atividade , Xantonas/química
9.
J Pharm Pharmacol ; 68(11): 1430-1439, 2016 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-27671368

RESUMO

OBJECTIVES: The Cnidium monnieri fruits (CMF) were studied how they act on immune system as a novel immunostimulator against the infectious disease. METHODS: Macrophages were treated with CMF, and nitric oxide (NO) and tumour necrosis factor-α (TNF-α) were measured, and phagocytosis of macrophages was detected using FITC-labelled Escherichia coli. The protective effect of CMF against E. coli infection in mice was examined. The survival rate was monitored daily for up to 5 days. And then the viable bacteria count of serum and the immunological mediator (NO, TNF-α, interleukin (IL)-12 and IL-6) of serum, splenocyte and peritoneal macrophages were analysed. KEY FINDINGS: The CMF significantly enhanced the concentrations of NO and TNF-α and the phagocytosis activity in macrophages. The oral administration of CMF for five consecutive days before infection prolonged the survival rate. Treatment with CMF significantly stimulated the phagocytosis of peritoneal macrophages and induced the immunological mediator of serum, splenocyte and peritoneal macrophages against the E. coli infection. CONCLUSIONS: The host-protective effects of CMF might be archived by improving immune response, and CMF could act to prevent pathogenic microbial infections with immunomodulation.


Assuntos
Adjuvantes Imunológicos/farmacologia , Cnidium/química , Infecções por Escherichia coli/tratamento farmacológico , Escherichia coli/patogenicidade , Frutas/química , Macrófagos/efeitos dos fármacos , Fagocitose/efeitos dos fármacos , Extratos Vegetais/farmacologia , Adjuvantes Imunológicos/isolamento & purificação , Animais , Proliferação de Células/efeitos dos fármacos , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Escherichia coli/imunologia , Infecções por Escherichia coli/sangue , Infecções por Escherichia coli/imunologia , Infecções por Escherichia coli/microbiologia , Interações Hospedeiro-Patógeno , Interleucina-12/sangue , Interleucina-6/sangue , Macrófagos/imunologia , Macrófagos/metabolismo , Macrófagos/microbiologia , Masculino , Camundongos , Camundongos Endogâmicos ICR , Óxido Nítrico/sangue , Fitoterapia , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Células RAW 264.7 , Baço/efeitos dos fármacos , Baço/imunologia , Baço/metabolismo , Baço/microbiologia , Fatores de Tempo , Fator de Necrose Tumoral alfa/sangue
10.
Bioorg Med Chem Lett ; 26(20): 4950-4954, 2016 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-27634197

RESUMO

Seven new sesquiterpenes, linderolides N-T (1-7), along with nine known compounds, were isolated from roots of Lindera strychnifolia (Lauraceae). Their structures were established by extensive spectroscopic analysis. The relative and absolute configurations were determined by NOESY and CD analysis, respectively. Among the isolated compounds, two new compounds, linderolide O (2) and linderolide P (3) inhibited lipopolysaccharide-stimulated nitric oxide production in murine RAW 264.7 macrophage cells, with IC50 values of 6.3 and 9.6µM, respectively.


Assuntos
Lindera/química , Óxido Nítrico/antagonistas & inibidores , Raízes de Plantas/química , Sesquiterpenos/isolamento & purificação , Animais , Linhagem Celular , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Camundongos , Óxido Nítrico/biossíntese , Espectrometria de Massas por Ionização por Electrospray
11.
J Food Sci ; 81(5): T1328-35, 2016 May.
Artigo em Inglês | MEDLINE | ID: mdl-27075529

RESUMO

Morus alba L. is a traditional herb with a long history of consumption, both as an edible fruit and as medicine. However, its safety evaluation has not yet been established. The objective of this study was to evaluate subchronic oral toxicity and genotoxicity of M. alba L. fruits (MFE). The subchronic toxicity after daily oral administration of MFE at 0, 40, 200, and 1000 mg/kg for 90 d was examined in Sprague Dawley (SD) rats. MFE administration did not lead to death, adverse effects, change in food and water consumption, and body weight gain. Significant toxic effects were not found within the parameters of organ weight, biochemical values, and hematological and urine analysis between the control and the MFE group. The genotoxicity of MFE was assayed by Ames test in Salmonella typhimurium strains TA98, TA102, and TA1535. No genotoxicity was found in all the tested strains. Thus in this study, a no-observed-adverse-effect level for MFE in 90 d repeated oral toxicity study in rats was determined to be greater than 1000 mg/kg regardless of gender. The results also suggested that MFE does not have a genotoxicity potential.


Assuntos
Frutas , Morus , Extratos Vegetais/toxicidade , Administração Oral , Animais , Dano ao DNA , Feminino , Masculino , Testes de Mutagenicidade , Nível de Efeito Adverso não Observado , Tamanho do Órgão/efeitos dos fármacos , Extratos Vegetais/farmacologia , Ratos , Ratos Sprague-Dawley , Salmonella typhimurium/efeitos dos fármacos , Salmonella typhimurium/genética , Testes de Toxicidade Subcrônica
12.
Nutrients ; 7(12): 10480-90, 2015 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-26694457

RESUMO

Obesity, which is characterized by excessive fat accumulation, is associated with several pathological disorders, including metabolic diseases. In this study, the anti-obesity effect of 6,8-diprenylgenistein (DPG), a major isoflavonoid of Cudrania tricuspidata fruits was investigated using high fat-diet (HFD)-induced obese mice at the doses of 10 and 30 mg/kg for six week. The body weight of the DPG-treated groups was significantly lower compared to the HFD-treated group. In addition, fat accumulation in epididymal adipose tissue and liver was dramatically decreased in the HFD + DPG groups. The food efficiency ratios of the HFD + DPG groups were also lower compared to the HFD group with the same food intake. Metabolic parameters that had increased in the HFD group were decreased in the HFD + DPG groups. Further studies demonstrate that DPG efficiently reduces lipogenic genes by regulation of transcription factors, such as peroxisome proliferator-activated receptor γ (PPARγ) and CCAAT/enhancer-binding protein α (C/EBPα), and hormones, such as leptin and adiponection. DPG also regulates acetyl-CoA carboxylase (ACC) and hydroxy-3-methylglutaryl coenzyme A reductase (HMGCR) by AMP-activated protein kinase (AMPK) activation. Taken together, DPG is beneficial for the regulation of obesity, especially resulting from high fat intake.


Assuntos
Fármacos Antiobesidade/farmacologia , Frutas/química , Genisteína/análogos & derivados , Isoflavonas/farmacologia , Moraceae/química , Obesidade/tratamento farmacológico , Proteínas Quinases Ativadas por AMP/genética , Proteínas Quinases Ativadas por AMP/metabolismo , Acetil-CoA Carboxilase/genética , Acetil-CoA Carboxilase/metabolismo , Adiponectina/metabolismo , Tecido Adiposo/efeitos dos fármacos , Tecido Adiposo/metabolismo , Animais , Proteína alfa Estimuladora de Ligação a CCAAT/genética , Proteína alfa Estimuladora de Ligação a CCAAT/metabolismo , Dieta Hiperlipídica , Regulação da Expressão Gênica , Genisteína/farmacologia , Hidroximetilglutaril-CoA Redutases/genética , Hidroximetilglutaril-CoA Redutases/metabolismo , Leptina/metabolismo , Fígado/efeitos dos fármacos , Fígado/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Camundongos Obesos , PPAR gama/genética , PPAR gama/metabolismo , Extratos Vegetais/farmacologia
13.
Molecules ; 20(11): 19764-74, 2015 Nov 02.
Artigo em Inglês | MEDLINE | ID: mdl-26540033

RESUMO

Bee pollen is flower pollen with nectar and salivary substances of bees and rich in essential components. Bee pollen showed antioxidant and tyrosinase inhibitory activity in our assay system. To maximize the antioxidant and tyrosinase inhibitory activity of bee pollen, extraction conditions, such as extraction solvent, extraction time, and extraction temperature, were optimized using response surface methodology. Regression analysis showed a good fit of this model and yielded the second-order polynomial regression for tyrosinase inhibition and antioxidant activity. Among the extraction variables, extraction solvent greatly affected the activity. The optimal condition was determined as EtOAc concentration in MeOH, 69.6%; temperature, 10.0 °C; and extraction time, 24.2 h, and the tyrosinase inhibitory and antioxidant activity under optimal condition were found to be 57.9% and 49.3%, respectively. Further analysis showed the close correlation between activities and phenolic content, which suggested phenolic compounds are active constituents of bee pollen for tyrosinase inhibition and antioxidant activity. Taken together, these results provide useful information about bee pollen as cosmetic therapeutics to reduce oxidative stress and hyperpigmentation.


Assuntos
Abelhas , Extratos Vegetais/química , Pólen/química , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Modelos Teóricos , Monofenol Mono-Oxigenase/antagonistas & inibidores , Fenóis/química , Fenóis/farmacologia , Extratos Vegetais/farmacologia
14.
Int J Mol Sci ; 16(10): 24139-58, 2015 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-26473845

RESUMO

Morus alba L. fruits have long been used in traditional medicine by many cultures. Their medicinal attributes include cardiovascular, hepatoprotective, neuroprotective and immunomodulatory actions. However, their mechanism of macrophage activation and anti-cancer effects remain unclear. The present study investigated the molecular mechanisms of immune stimulation and improved chemotherapeutic effect of M. alba L. fruit extract (MFE). MFE stimulated the production of cytokines, nitric oxide (NO) and tumor necrosis factor-α (TNF-α) and tumoricidal properties of macrophages. MFE activated macrophages through the mitogen-activated protein kinase (MAPKinase) and nuclear factor-κB (NF-κB) signaling pathways downstream from toll-like receptor (TLR) 4. MFE was shown to exhibit cytotoxicity of CT26 cells via the activated macrophages, even though MFE did not directly affect CT26 cells. In a xenograft mouse model, MFE significantly enhanced anti-cancer activity combined with 5-fluorouracil and markedly promoted splenocyte proliferation, natural killer (NK) cell activity, cytotoxic T lymphocyte (CTL) activity and IFN-γ production. Immunoglobulin G (IgG) antibody levels were significantly increased. These results indicate the indirect anti-cancer activity of MFE through improved immune response mediated by TLR4 signaling. M. alba L. fruit extract might be a potential anti-tumor immunomodulatory candidate chemotherapy agent.


Assuntos
Antineoplásicos/farmacologia , Protocolos de Quimioterapia Combinada Antineoplásica/farmacologia , Fluoruracila/farmacologia , Macrófagos/imunologia , Morus/metabolismo , Neoplasias/imunologia , Extratos Vegetais/farmacologia , Linfócitos T Citotóxicos/imunologia , Receptor 4 Toll-Like/imunologia , Proteínas Adaptadoras de Transporte Vesicular/genética , Proteínas Adaptadoras de Transporte Vesicular/imunologia , Animais , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Feminino , Frutas/metabolismo , Células Matadoras Naturais/imunologia , Sistema de Sinalização das MAP Quinases/imunologia , Ativação de Macrófagos/efeitos dos fármacos , Ativação de Macrófagos/imunologia , Camundongos , Camundongos Endogâmicos BALB C , Proteínas Quinases Ativadas por Mitógeno/imunologia , Fator 88 de Diferenciação Mieloide/genética , Fator 88 de Diferenciação Mieloide/imunologia , NF-kappa B/imunologia , Transplante de Neoplasias , Neoplasias/tratamento farmacológico , Óxido Nítrico/biossíntese , Óxido Nítrico/imunologia , Interferência de RNA , RNA Interferente Pequeno/genética , Receptor 2 Toll-Like/genética , Receptor 2 Toll-Like/imunologia , Receptor 4 Toll-Like/genética , Transplante Heterólogo , Fator de Necrose Tumoral alfa/biossíntese , Fator de Necrose Tumoral alfa/imunologia
15.
Molecules ; 20(9): 16933-45, 2015 Sep 17.
Artigo em Inglês | MEDLINE | ID: mdl-26393543

RESUMO

Resveratrol (1), a naturally occurring stilbene compound, has been suggested as a potential whitening agent with strong inhibitory activity on melanin synthesis. However, the use of resveratrol in cosmetics has been limited due to its chemical instability and poor bioavailability. Therefore, resveratrol derivatives were prepared to improve bioavailability and anti-melanogenesis activity. Nine resveratrol derivatives including five alkyl ether derivatives with C2H5, C4H9, C5H11, C6H13, and C8H17 (2a-2e) and four ester derivatives with CH3, CH=C(CH3)2, CH(C2H5)C4H9, C7H15 (3a-3d) were newly synthesized and their effect on melanin synthesis were assessed. All the synthetic derivatives efficiently reduced the melanin content in α-MSH stimulated B16F10 melanoma cells. Further investigation showed that the inhibitory effect of 2a on melanin synthesis was achieved not by the inhibition of tyrosinase activity but by the inhibition of melanogenic enzyme expressions such as tyrosinase and tyrosinase-related protein (TRP)-1. Our synthetic resveratrol derivatives have more lipophilic properties than resveratrol by the addition of alkyl or acyl chains to free hydroxyl moiety of resveratrol; thus, they are expected to show better bioavailability in skin application. Therefore, we suggest that our synthetic resveratrol derivatives might be promising candidates for better practical application to skin-whitening cosmetics.


Assuntos
Melaninas/metabolismo , Estilbenos/síntese química , Estilbenos/farmacologia , Animais , Disponibilidade Biológica , Linhagem Celular Tumoral , Regulação Enzimológica da Expressão Gênica/efeitos dos fármacos , Glicoproteínas de Membrana/metabolismo , Camundongos , Estrutura Molecular , Monofenol Mono-Oxigenase/metabolismo , Oxirredutases/metabolismo , Resveratrol , Preparações Clareadoras de Pele/síntese química , Preparações Clareadoras de Pele/farmacocinética , Preparações Clareadoras de Pele/farmacologia , Estilbenos/agonistas , Estilbenos/química , Estilbenos/farmacocinética , alfa-MSH/farmacologia
16.
Bioorg Med Chem Lett ; 25(17): 3455-7, 2015 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-26227773

RESUMO

A new benzylated and prenylated flavonone, cudracuspiflavanone A (17) were isolated from the roots of Cudrania tricuspidata (Moraceae), together with two chromones (1-2) and fourteen flavonoids (3-16). The structures of isolated compounds were determined on the basis of spectroscopic analysis. The absolute configuration was also defined by CD analysis. Among the isolated compounds, compounds 14 and 15 inhibited pancreatic lipase activity with an IC50 value of 9.0 and 6.5 µM, respectively.


Assuntos
Flavonoides/química , Lipase/química , Moraceae/química , Obesidade/tratamento farmacológico , Pâncreas/efeitos dos fármacos , Extratos Vegetais/química , Produtos Biológicos , Estrutura Molecular
17.
Bioorg Med Chem Lett ; 25(11): 2269-74, 2015 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-25935644

RESUMO

The leaves of Morus alba (Moraceae) have been traditionally used for the treatment of metabolic diseases including diabetes and hyperlipidemia. Thus, inhibitory effect of M. alba leaves on pancreatic lipase and their active constituents were investigated in this study. Twenty phenolic compounds including ten flavonoids, eight benzofurans, one stilbene and one chalcones were isolated from the leaves of M. alba. Among the isolated compounds, morachalcone A (20) exerted strong pancreatic lipase inhibition with IC50 value of 6.2 µM. Other phenolic compounds containing a prenyl group showed moderate pancreatic lipase inhibition with IC50 value of <50 µM. Next, extraction conditions with maximum pancreatic lipase inhibition and phenolic content were optimized using response surface methodology with three-level-three-factor Box-Behnken design. Our results suggested the optimized extraction condition for maximum pancreatic lipase inhibition and phenolic content as ethanol concentration of 74.9%; temperature 57.4 °C and sample/solvent ratio, 1/10. The pancreatic lipase inhibition and total phenolic content under optimized condition were found to be 58.5% and 26.2 µg GAE (gallic acid equivalent)/mg extract, respectively, which were well matched with the predicted value.


Assuntos
Lipase/antagonistas & inibidores , Morus/química , Pâncreas/enzimologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Fracionamento Químico/métodos , Lipase/metabolismo , Estrutura Molecular , Extratos Vegetais/química
18.
Molecules ; 20(5): 8730-41, 2015 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-26007176

RESUMO

Melanin is a natural pigment that plays an important role in the protection of skin, however, hyperpigmentation cause by excessive levels of melatonin is associated with several problems. Therefore, melanogenesis inhibitory natural products have been developed by the cosmetic industry as skin medications. The leaves of Morus alba (Moraceae) have been reported to inhibit melanogenesis, therefore, characterization of the melanogenesis inhibitory constituents of M. alba leaves was attempted in this study. Twenty compounds including eight benzofurans, 10 flavonoids, one stilbenoid and one chalcone were isolated from M. alba leaves and these phenolic constituents were shown to significantly inhibit tyrosinase activity and melanin content in B6F10 melanoma cells. To maximize the melanogenesis inhibitory activity and active phenolic contents, optimized M. alba leave extraction conditions were predicted using response surface methodology as a methanol concentration of 85.2%; an extraction temperature of 53.2 °C and an extraction time of 2 h. The tyrosinase inhibition and total phenolic content under optimal conditions were found to be 74.8% inhibition and 24.8 µg GAE/mg extract, which were well-matched with the predicted values of 75.0% inhibition and 23.8 µg GAE/mg extract. These results shall provide useful information about melanogenesis inhibitory constituents and optimized extracts from M. alba leaves as cosmetic therapeutics to reduce skin hyperpigmentation.


Assuntos
Hiperpigmentação/tratamento farmacológico , Melaninas/biossíntese , Monofenol Mono-Oxigenase/antagonistas & inibidores , Morus/metabolismo , Extratos Vegetais/farmacologia , Benzofuranos/farmacologia , Linhagem Celular Tumoral , Chalcona/farmacologia , Flavonoides/farmacologia , Humanos , Hiperpigmentação/metabolismo , Melaninas/metabolismo , Melanoma/metabolismo , Melanoma/patologia , Fenóis/química , Folhas de Planta/metabolismo , Estilbenos/farmacologia
19.
Nat Prod Commun ; 9(10): 1399-401, 2014 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-25522524

RESUMO

The effect of the extract of Ligustrumn lucidum fruits (LFE) and its major secoiridoid (LFS), (8-E)-nüzhenide, on obesity was investigated using high fat-diet (HFD)-induced C58BL/6J obese mice. LFE and LFS were administered at the doses of 300 mg/kg and 30 mg/kg, respectively, for 6 weeks. The anti-obesity activity was evaluated by measuring body weight, epididymal fat and metabolic plasma parameters. On Day 42, the body weight of the LFS-treated group was significantly lower compared with the HFD-treated group. Body weight gain was also reduced by 23.2% and 32.0% in the LFE- and LFS-treated groups, respectively, compared with the HFD group. In addition, the weight of the epididymal fat in the mice was significantly decreased in the HFD+LFS group. The food efficiency ratios (FERs) of the HFD+LFE and HFD+LFS groups were also lower compared with the HFD group with the same food intake. Metabolic parameters that had increased in the HFD group were decreased in the HFD+LFE and HFD+LFS groups. In particular, the increased triglyceride values were significantly reduced in the HFD+LFS group. These results show that treatment with LFE and LFS decreased HFD-induced obesity, mainly by improving metabolic parameters, such as fats and triglycerides. Therefore, LFE and LFS have potential benefits in regulation of obesity.


Assuntos
Hipoglicemiantes/uso terapêutico , Iridoides/uso terapêutico , Ligustrum/química , Obesidade/tratamento farmacológico , Animais , Peso Corporal/efeitos dos fármacos , Dieta Hiperlipídica/efeitos adversos , Hipoglicemiantes/química , Iridoides/química , Camundongos , Camundongos Obesos , Obesidade/etiologia
20.
Bioorg Med Chem Lett ; 24(24): 5656-5659, 2014 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-25467154

RESUMO

Phytochemical investigation of the fruits of Morus alba afforded seventeen pyrrole alkaloids including five new compounds. The structures of five new pyrrole alkaloids, named morroles B-F (4, 5, 7, 16 and 17), were determined on the basis of spectroscopic interpretations. 4-[Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]butanoate (2) was synthesized by chemical reaction but first isolated from nature. Among isolated compounds, compounds 6 and 14 significantly inhibited pancreatic lipase activity.


Assuntos
Alcaloides/isolamento & purificação , Frutas/química , Lipase/antagonistas & inibidores , Morus/química , Pâncreas/enzimologia , Pirróis/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Animais , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Pâncreas/efeitos dos fármacos , Pirróis/química , Pirróis/farmacologia , Suínos
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