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1.
J Agric Food Chem ; 68(8): 2562-2569, 2020 Feb 26.
Artigo em Inglês | MEDLINE | ID: mdl-32003990

RESUMO

This study was aimed to evaluate the level of furan and acrylamide contamination in cocoa and noncocoa raw materials, in masses from processing stages, and in chocolates originating from three factories. Acrylamide was determined by the gas chromatography-mass spectrometry (GC-MS) method using the QuEChERS procedure with dispersive solid-phase extraction clean-up and isotopic standard (2,3,3-d3-acrylamide). Furan was analyzed by the headspace solid-phase microextraction/GC-MS technique with the d4-furan marker. Both analytical methods were validated in terms of accuracy, precision, and linearity as well as the limit of detection (LOD) and limit of quantification (LOQ). Among all raw materials, the most abundant in acrylamide were cocoa masses and powders (83.0-127.5 ng g-1). Roasting of cocoa beans increased the content of acrylamide 2-3-fold. The obtained results indicate that acrylamide might be formed during wet conching. Only in cocoa powders and lecithin, it was possible to quantify furan (3.7-10.2 and 16.3 ng g-1, respectively). Roasting of cocoa beans increased the content of furan from

Assuntos
Acrilamida/análise , Cacau/química , Chocolate/análise , Furanos/análise , Acrilamida/isolamento & purificação , Contaminação de Alimentos/análise , Manipulação de Alimentos , Furanos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Sementes/química , Microextração em Fase Sólida
2.
Molecules ; 24(16)2019 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-31426361

RESUMO

Key odorants of red wine made from the hybrid grapes of Marselan (Vitis vinifera L.) were isolated by solid-phase extraction (SPE) and explored by gas chromatography-olfactometry (GC-O) analysis. Application of aroma extract dilution analysis (AEDA) revealed 43 odor-active compounds, and 31 odorants among them were detected with flavor dilution (FD) factors ranging from 9 to 2187. Comprehensive two-dimensional gas chromatography and time-of-flight mass spectrometry (GC × GC-TOF-MS) were exploited to quantitate the aroma-active compounds with FD ≥9. The identification indicated ß-damascenone as having the highest FD factors, followed by eugenol, 2,3-butanedione, citronellol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, phenethyl acetate, guaiacol, and 2-methoxy-4-vinylphenol. A total of 21 compounds were found to have odor activity values (OAVs) >1.0. Aroma reconstitution validation experiments showed a good similarity of blackberry, green pepper, honey, raspberry, caramel, smoky, and cinnamon aroma attributes between the original Marselan wine and the reconstructed wine. In addition, omission tests were carried out to further determine the contribution of odorants to the overall aroma.


Assuntos
Odorantes/análise , Olfato/fisiologia , Vitis/química , Compostos Orgânicos Voláteis/isolamento & purificação , Vinho/análise , /isolamento & purificação , Diacetil/isolamento & purificação , Eugenol/isolamento & purificação , Feminino , Furanos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Guaiacol/análogos & derivados , Guaiacol/isolamento & purificação , Humanos , Masculino , Norisoprenoides/isolamento & purificação , Olfatometria/instrumentação , Olfatometria/métodos , Extração em Fase Sólida/métodos , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Paladar/fisiologia , Compostos de Vinila/isolamento & purificação , Compostos Orgânicos Voláteis/classificação
3.
Chem Biodivers ; 16(9): e1900266, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31298476

RESUMO

Two new spliceostatin analogs, designed as spliceostatins J and K (1 and 2), were isolated and identified from the culture of Pseudomonas sp., along with two known ones, FR901464 (3) and spliceostatin E (4). Their structures were elucidated by detailed interpretation of their spectroscopic data, especially 2D-NMR and HR-ESI-MS. Spliceostatin J (1) represented the first example of spliceostatins bearing an unusual hexahydrofuro[3,4-b]furan moiety. Biological assay showed all the isolated compounds except 1 displayed potent cytotoxic activities against two cancer cell lines (MDA-MB-231 and A-549). Structure-activity-relationship studies revealed that the tetrahydropyran ring in spliceostatin analogs was necessary for their bioactive retention.


Assuntos
Antineoplásicos/farmacologia , Furanos/farmacologia , Lactonas/farmacologia , Pseudomonas/química , Pironas/farmacologia , Células A549 , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Furanos/química , Furanos/isolamento & purificação , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Estrutura Molecular , Piranos/química , Piranos/isolamento & purificação , Piranos/farmacologia , Pironas/química , Pironas/isolamento & purificação , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia , Relação Estrutura-Atividade
4.
Phytochemistry ; 164: 122-129, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31125862

RESUMO

A phytochemical study on the fruits of Rubus idaeus L. (Rosaceae) yielded eight pairs of enantiomeric lignans, including one undescribed furolactone named (-)-idaeusinol A and six undescribed furofuran derivatives named (+/-)-idaeusinol B-D. The structures of these isolated compounds were elucidated by spectroscopic analyses and a combination of computational techniques including gauge-independent atomic orbital (GIAO) calculation of 1D NMR data and TD-DFT calculation of electronic circular dichroism (ECD) spectra. Bioactivity screenings suggested that (+)-idaeusinol D exhibited the most significant protective effect against H2O2-induced neurotoxicity at the concentration of 25 µM. In contrast, (-)-idaeusinol D, as the enantiomer of (+)-idaeusinol D, showed no effect against H2O2-induced neurotoxicity at both 25 and 50 µM concentration.


Assuntos
Furanos/farmacologia , Lactonas/farmacologia , Fármacos Neuroprotetores/farmacologia , Rubus/química , Sobrevivência Celular/efeitos dos fármacos , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Furanos/química , Furanos/isolamento & purificação , Humanos , Peróxido de Hidrogênio/antagonistas & inibidores , Peróxido de Hidrogênio/farmacologia , Lactonas/química , Lactonas/isolamento & purificação , Conformação Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Estereoisomerismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
5.
Molecules ; 24(7)2019 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-30934811

RESUMO

Although smoke-isolated karrikins (KAR1) could regulate secondary metabolism in medicinal plants, the signal transduction mechanism has not been reported. This study highlights the influence of KAR1 on tanshinone I (T-I) production in Salvia miltiorrhiza and the involved signal molecules. Results showed KAR1-induced generation of nitric oxide (NO), jasmonic acid (JA) and T-I in S. miltiorrhiza hairy root. KAR1-induced increase of T-I was suppressed by NO-specific scavenger (cPTIO) and NOS inhibitors (PBITU); JA synthesis inhibitor (SHAM) and JA synthesis inhibitor (PrGall), which indicated that NO and JA play essential roles in KAR1-induced T-I. NO inhibitors inhibited KAR1-induced generation of NO and JA, suggesting NO was located upstream of JA signal pathway. NO-induced T-I production was inhibited by SHAM and PrGall, implying JA participated in transmitting signal NO to T-I accumulation. In other words, NO mediated the KAR1-induced T-I production through a JA-dependent signaling pathway. The results helped us understand the signal transduction mechanism involved in KAR1-induced T-I production and provided helpful information for the production of S. miltiorrhiza hairy root.


Assuntos
/biossíntese , Ciclopentanos/metabolismo , Furanos/farmacologia , Óxido Nítrico/metabolismo , Oxilipinas/metabolismo , Piranos/farmacologia , Salvia miltiorrhiza/efeitos dos fármacos , Salvia miltiorrhiza/metabolismo , Fumaça , Análise de Variância , Furanos/isolamento & purificação , Regulação da Expressão Gênica de Plantas , Redes e Vias Metabólicas/efeitos dos fármacos , Raízes de Plantas/efeitos dos fármacos , Raízes de Plantas/metabolismo , Piranos/isolamento & purificação , Salvia miltiorrhiza/genética , Transdução de Sinais/efeitos dos fármacos , Fumaça/análise
6.
Life Sci ; 223: 194-201, 2019 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-30898648

RESUMO

AIMS: Diabetic nephropathy (DN) is the most common complication of diabetes mellitus. Endoplasmic reticulum (ER) plays an important role in the development and progression of DN. Arctigenin (ATG), a lignan extract from Fructus Arctii, exhibits anti-inflammatory, anticarcinogenic, anti-oxidative stress and immunomodulatory properties. The present research aimed to investigate whether ATG could protect against diabetes-related renal injury and inhibit ER stress in db/db mice. MAIN METHODS: Male db/db mice were randomly divided into two groups: DN group and ATG treatment group (DN + ATG). db/m mice were defined as the normal control group (NC). ATG was dissolved in 0.5% carboxymethyl cellulose sodium salt solution and administered orally at a dose of 80 mg/kg to mice in the DN + ATG group once daily for 8 consecutive weeks. HK2 cells were used to determine the effects of ATG on ER stress and cell apoptosis in vitro. KEY FINDINGS: ATG administration significantly reduced blood glucose, urine albumin excretion, and urine albumin to creatinine ratio, and attenuated renal pathological injury when compared with untreated db/db mice. These changes were accompanied by decreased expression of both ER stress-related markers and caspase 12 level in the kidneys of db/db mice. In vitro, high glucose activated ER stress signal transduction pathway and induced cell apoptosis in HK2 cells, which were blocked by ATG. SIGNIFICANCE: Our results suggest that ATG exerts renoprotective effects on diabetes-related renal injury in db/db mice and cytoprotective effects on high glucose induced cell apoptosis and inhibits ER stress.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Nefropatias Diabéticas/prevenção & controle , Estresse do Retículo Endoplasmático/efeitos dos fármacos , Furanos/uso terapêutico , Hipoglicemiantes/uso terapêutico , Lignanas/uso terapêutico , Animais , Apoptose/efeitos dos fármacos , Arctium/química , Técnicas de Cultura de Células , Linhagem Celular , Diabetes Mellitus Experimental/complicações , Diabetes Mellitus Experimental/metabolismo , Diabetes Mellitus Experimental/patologia , Nefropatias Diabéticas/metabolismo , Nefropatias Diabéticas/patologia , Células Epiteliais/efeitos dos fármacos , Células Epiteliais/metabolismo , Furanos/isolamento & purificação , Humanos , Hipoglicemiantes/isolamento & purificação , Rim/efeitos dos fármacos , Rim/metabolismo , Rim/patologia , Lignanas/isolamento & purificação , Masculino , Camundongos Endogâmicos C57BL
7.
Fitoterapia ; 135: 5-8, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30914329

RESUMO

Two new spiroketal derivatives with an unprecedented amino group, 2'-aminodechloromaldoxin (1) and 2'-aminodechlorogeodoxin (2), along with one known analogue dechloromaldoxin (3), were isolated from the plant endophytic fungus Pestalotiopsis flavidula. Their structures were elucidated on the basis of extensive spectroscopic analysis. The purification was cytotoxicity-guided which indicated the extract, fractions and compounds were evaluated in vitro for anti-proliferative activity against a panel of human cancer cell lines. The results showed compounds 1 and 2 with moderate cytotoxicity while 3 was inactive, which suggested -NH2 group might play a very important role for their cytotoxicity. This is the first study for P. flavidula and the first time to report the spiroketal derivatives as alkaloids from the Pestalotiopsis genus.


Assuntos
Alcaloides/farmacologia , Furanos/farmacologia , Compostos de Espiro/farmacologia , Xylariales/química , Alcaloides/química , Alcaloides/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Furanos/química , Furanos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação
8.
Molecules ; 24(6)2019 Mar 18.
Artigo em Inglês | MEDLINE | ID: mdl-30889936

RESUMO

As part of our efforts to exploit the antitrypanosomal potential of sesquiterpene lactones (STL) from Helianthus tuberosus L. (Asteraceae), besides the known 4,15-iso-atriplicolide tiglate, -methacrylate and -isobutyrate, a hitherto unknown STL was isolated. Its structure was solved by extensive NMR measurements and confirmed by single crystal X-ray crystallography. This novel compound is a structural analog 4,15-iso-atriplicolide tiglate that possesses the same basic furanoheliangolide skeleton but differs in the position of the oxo function which is at C-2 instead of C-1, as well as in the fact that the oxygen atom of the furanoid ring is part of a hemiketal structure at C-3 and a double bond between C-5 and C-6. For this new STL we propose the name heliantuberolide-8-O-tiglate. Its activity against Trypanosoma brucei rhodesiense (causative agent of East African Human Typanosomiasis, Trypanosoma cruzi (Chagas Disease), Leishmania donovani (Visceral Leishmaniasis) and Plasmodium falciparum (Tropical Malaria) as well as cytotoxicity against rat skeletal myoblasts (L6 cell line) was determined along with those of the hitherto untested 4,15-iso-atriplicolide methacrylate and isobutyrate. In comparison with the iso-atriplicolide esters, the new compound showed a much lower level of bioactivity.


Assuntos
Antiprotozoários/química , Antiprotozoários/farmacologia , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Furanos/química , Furanos/farmacologia , Helianthus/química , Lactonas/farmacologia , Sesquiterpenos/farmacologia , Hidrocarbonetos Aromáticos com Pontes/isolamento & purificação , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Morte Celular/efeitos dos fármacos , Cristalografia por Raios X , Furanos/isolamento & purificação , Lactonas/química , Lactonas/isolamento & purificação , Plasmodium falciparum/efeitos dos fármacos , Espectroscopia de Prótons por Ressonância Magnética , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesterterpenos
9.
Fitoterapia ; 134: 256-263, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30826368

RESUMO

Six new neolignans, sinensiols B-G (1-6), together with three known analogues (7-9) were isolated from the whole plant of Selaginella sinensis. Their planar structures were established by comprehensive spectroscopic analyses including 1D, 2D NMR, IR and HRESIMS data. The absolute configurations of new compounds were elucidated by comparing their experimental CD spectra with known ones and using the reversed helicity rule for the 1Lb band ECD of dihydrobenzofuran neolignans. Sinensiols A-D (7, 1-3) belong to sesquilignan with a dimer of dihydrobenzo[b]furan moiety. The potential precursors of sinensiols A, B, D were also reported in this paper. In addition, all new compounds were screened for their cytotoxicity against A549 and HepG2 human cancer cell lines, and they didn't show inhibition on the growth of cancer cells.


Assuntos
Furanos/química , Lignanas/química , Selaginellaceae/química , Células A549 , China , Furanos/isolamento & purificação , Células Hep G2 , Humanos , Lignanas/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação
10.
Org Biomol Chem ; 17(8): 2182-2186, 2019 02 20.
Artigo em Inglês | MEDLINE | ID: mdl-30720839

RESUMO

Versispiroketal A (1), an unprecedented 6/5/5/6 tetracyclic polyketide featuring a rarely encountered bridge-fused spiroketal skeleton, was isolated from the sponge-associated fungus Aspergillus versicolor SCSIO 41013. The structure and absolute configuration of 1 were unequivocally determined by comprehensive spectroscopic analysis, single-crystal X-ray diffraction analysis and quantum chemical ECD calculations. Compound 1 showed weak cytotoxicity against four cancer cell lines. A plausible biosynthetic pathway for 1 was also postulated.


Assuntos
Aspergillus/química , Furanos/química , Poríferos/microbiologia , Compostos de Espiro/química , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Linhagem Celular Tumoral , Cristalografia por Raios X , Furanos/isolamento & purificação , Furanos/farmacologia , Humanos , Modelos Moleculares , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia
11.
Biomolecules ; 9(1)2019 01 02.
Artigo em Inglês | MEDLINE | ID: mdl-30609771

RESUMO

Over the past decades curcuminoids have been extensively studied for their biological activities such as antiulcer, antifibrotic, antiviral, antibacterial, antiprotozoal, antimutagenic, antifertility, antidiabetic, anticoagulant, antivenom, antioxidant, antihypotensive, antihypocholesteremic, and anticancer activities. With the perception of limited toxicity and cost, these compounds forms an integral part of cancer research and is well established as a potential anticancer agent. However, only few studies have focused on the other bioactive molecules of turmeric, known as non-curcuminoids, which are also equally potent as curcuminoids. This review aims to explore the comprehensive potency including the identification, physicochemical properties, and anticancer mechanism inclusive of molecular docking studies of non-curcuminoids such as turmerones, elemene, furanodiene (FN), bisacurone, germacrone, calebin A (CA), curdione, and cyclocurcumin. An insight into the clinical studies of these curcumin-free compounds are also discussed which provides ample evidence that favors the therapeutic potential of these compounds. Like curcuminoids, limited solubility and bioavailability are the most fragile domain, which circumscribe further applications of these compounds. Thus, this review credits the encapsulation of non-curcuminoid components in diverse drug delivery systems such as co-crystals, solid lipid nanoparticles, liposomes, microspheres, polar-non-polar sandwich (PNS) technology, which help abolish their shortcomings and flaunt their ostentatious benefits as anticancer activities.


Assuntos
Antineoplásicos/química , Curcuma/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/uso terapêutico , Curcuma/metabolismo , Portadores de Fármacos/química , Furanos/química , Furanos/isolamento & purificação , Furanos/uso terapêutico , Compostos Heterocíclicos com 2 Anéis/química , Compostos Heterocíclicos com 2 Anéis/isolamento & purificação , Compostos Heterocíclicos com 2 Anéis/uso terapêutico , Microesferas , Nanopartículas/química , Neoplasias/tratamento farmacológico , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/uso terapêutico
12.
N Biotechnol ; 48: 83-89, 2019 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-30098416

RESUMO

Bioactive compounds such as karrikinolide (KAR1 from smoke) and eckol (from the seaweed Ecklonia maxima) show promising effects on several important crop plants. These plant growth-stimulating organic biomolecules, along with crude extracts (smoke-water and Kelpak® product prepared from Ecklonia maxima), were tested on spinach plants. Eckol sprayed at 10-6 M significantly increased all the growth and biochemical parameters examined compared to control spinach plants. All tested plant growth biostimulants significantly increased total chlorophyll, carotenoids and protein content of spinach leaves. The cytokinin profile of spinach plants was also determined. Cis-zeatin, dihydrozeatin and isopentenyladenine types of cytokinins were promoted by both smoke- and seaweed-based biostimulants. In comparison to the control plants, the level of free sinapic acid was greater in all spinach plants treated with these biostimulants. The application of these biostimulants can help spinach crop by improving growth, yield and nutritional quality; moreover, they are organic and cost-effective.


Assuntos
Feófitas/química , Reguladores de Crescimento de Planta/isolamento & purificação , Reguladores de Crescimento de Planta/farmacologia , Alga Marinha/química , Fumaça/análise , Spinacia oleracea/efeitos dos fármacos , Spinacia oleracea/crescimento & desenvolvimento , Produtos Agrícolas/efeitos dos fármacos , Produtos Agrícolas/crescimento & desenvolvimento , Produtos Agrícolas/metabolismo , Citocininas/metabolismo , Dioxinas/isolamento & purificação , Dioxinas/farmacologia , Furanos/isolamento & purificação , Furanos/farmacologia , Hidroxibenzoatos/metabolismo , Piranos/isolamento & purificação , Piranos/farmacologia , Spinacia oleracea/metabolismo
13.
Planta ; 249(3): 709-718, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30374913

RESUMO

MAIN CONCLUSION: Chlorophyll fluorescence, infrared gas exchange and photoinhibition data consistently show that vulpinic acid in L. vulpina functions as a strong blue light screening compound. The cortical lichen compounds, parietin, atranorin, usnic acid and melanins are known to screen photosynthetically active radiation (PAR), thereby protecting the underlying photobionts. The role of the toxic UV-/blue light-absorbing vulpinic acid in lichen cortices is poorly documented. By comparing controls with acetone-rinsed Letharia vulpina thalli (75% reduced vulpinic acid concentration), we aimed to test PAR screening by vulpinic acid. We exposed such thalli to blue, green and red irradiance, respectively, and recorded light quality-specific light saturation curves of CO2 uptake, quantum yields of CO2 uptake (QYCO2) and effective quantum yields of PSII (ΦPSII). We also quantified light quality-dependent photoinhibition after 4-h exposure to 400 µmol photons m-2 s-1. In controls, the greatest high light-induced reductions in CO2 uptake and ΦPSII, as well as the strongest photoinhibition [lowered maximal quantum yield of PSII (Fv/Fm)], occurred in red light, followed by green, and was low in blue light. Removal of vulpinic acid significantly exacerbated photoinhibition, reduced ΦPSII, and increased QYCO2 in blue light. By contrast, acetone rinsing had no or weak effects in green and red lights. Comparing control with acetone-rinsed thalli, blue light screening was estimated at 69% using ΦPSII data and 49% using QYCO2. To compensate for the 25% residual vulpinic acid left after rinsing, we repeated the screening estimation by comparing responses in blue and red lights. This resulted in 88% screening using ΦPSII data and 77% using QYCO2. The consistent responses in all photosynthetic parameters support the hypothesis that vulpinic acid functions as a blue light screen in L. vulpina.


Assuntos
Furanos/metabolismo , Parmeliaceae/metabolismo , Fenilacetatos/metabolismo , Dióxido de Carbono/metabolismo , Clorofila/metabolismo , Clorofila/efeitos da radiação , Cor , Furanos/isolamento & purificação , Furanos/efeitos da radiação , Luz , Parmeliaceae/efeitos da radiação , Fenilacetatos/isolamento & purificação , Fenilacetatos/efeitos da radiação
14.
Nat Prod Res ; 33(2): 212-218, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29468891

RESUMO

Two new prenylisoflavones, 3',4',5-trihydroxy-8-prenyl-dihydrofuran[2″,3″:7,6]isoflavone (1) and 4',5-dihydroxy-8-prenyl-dihydrofuran[2″,3″:7,6]isoflavone (2), along with five known prenylisoflavones (3-7), benzylalcohol-4-O-ß-d-glucoside (8) and two cinnamic acid esters (9, 10) were isolated from the leaves of Maclura cochinchinensis (Cudrania cochinchinensis). Their structures were elucidated by analysis of NMR (1H-, 13C-NMR, HSQC, HMBC), MS spectra and comparison with the published data. Compounds 4-10 were the first time isolated from this species. Prenylisoflavones 1-4 and 6-7 were evaluated for their in vitro cytotoxic activity on KB and HepG2 cancer cell lines. Compound 4 showed cytotoxic activity against both cancer cell lines with IC50 values of 26.99 and 19.95 µM, respectively. The other compounds were considered as inactive.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Furanos/química , Isoflavonas/química , Maclura/química , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Furanos/isolamento & purificação , Células Hep G2 , Humanos , Concentração Inibidora 50 , Isoflavonas/isolamento & purificação , Células KB , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Prenilação , Vietnã
15.
Nat Prod Res ; 33(23): 3404-3408, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29806501

RESUMO

Two new furandione derivatives, designated as asperfurandiones A (1) and B (2), were isolated from the solid culture of the marine-derived fungus Aspergillus versicolor. Their structures were elucidated using a combination of mass spectrometry and NMR spectroscopy. Additionally, asperfurandiones A and B both showed moderate antifungal activity against Gaeumannomyces graminis, Cryptococcus neoformans, and Candida albicans with MIC values of 64 µg/mL.


Assuntos
Antifúngicos/química , Aspergillus/química , Furanos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Cryptococcus neoformans/efeitos dos fármacos , Furanos/química , Furanos/isolamento & purificação , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos , Testes de Sensibilidade Microbiana , Estrutura Molecular
16.
Nat Prod Res ; 33(8): 1204-1208, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-29607669

RESUMO

Myristica fragrans Houtt., the source of very important spice 'nutmeg' used world over is native to India, Indonesia, Sri Lanka, South Africa and Southeast Asia. Phytochemical investigation of M. fragrans stem bark led to the isolation of bis-aryl dimethyl tetrahydrofuran lignans, such as grandisin [(7S,8S,7'S,8'S)-3,3',4,4',5,5'-hexamethoxy-7,7',8,8'-lignan] and (7S,8S,7'R,8'R)-3,3',4,4',5,5'-hexamethoxy-7,7',8,8'-lignan along with important lignans and neolignans, licarinA, licarin B, odoratisol A, (2S, 3R)-7-methoxy-3-methyl-5-((E)-prop-1-enyl)-2-(5-methoxy,3,4-methylenedioxyphenyl)-2,3-dihydrobenzofuran, elemicin, fragransin B1, raphidecursinol B, erythro-(7S,8R)-Δ8'-4,7-dihydroxy-3,5,3'-trimethoxy-8-O-4'-neolignan, erythro-(7S,8R)-Δ8'-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan, surinamensin.and ß-sitosterol. Structures of the 12 compounds isolated were unambiguously identified by various spectroscopic methods. The former two compounds were isolated from M. fragrans for the first time. Furthermore, the X-ray crystal structure of odoratisol A is reported in this paper for the first time.


Assuntos
Myristica/química , Compostos Fitoquímicos/análise , Casca de Planta/química , Anisóis , Benzofuranos , Dioxóis , Furanos/análise , Furanos/isolamento & purificação , Índia , Indonésia , Lignanas/análise , Lignanas/isolamento & purificação , Estrutura Molecular , Análise Espectral , Sri Lanka
17.
J Asian Nat Prod Res ; 21(8): 735-741, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30014709

RESUMO

Two new compounds herialpins A-B (1-2), along with eleven known compounds, were isolated from the culture of fungus Hericium alpestre. The structures were elucidated by 1D and 2D NMR data, ESI-MS and X-ray crystallographic analysis. Compounds 1-2 were assayed for their cytotoxicity against three tumor cell lines compared with the known compound 3. Compounds 1 and 2 were found with modest activity, while compound 3 exhibits stronger selective inhibitory activity against A549 and HT-29 cells with IC50 values of 15.1 and 20.1 µmol/L, respectively. The pyrano[3,4-g]chromene-4,6-dione moiety in compound 3 should be responsible for the stronger selective inhibitory activity.


Assuntos
Agaricales/química , Furanos/isolamento & purificação , Isoindóis/isolamento & purificação , Células A549 , Agaricales/crescimento & desenvolvimento , Fermentação , Furanos/farmacologia , Células HT29 , Humanos , Isoindóis/farmacologia
18.
J Oleo Sci ; 67(11): 1483-1499, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30404969

RESUMO

The aerial part of Clematis flammula (Ranunculaceae) has been traditionally used in the treatment of skin diseases including mycotic infection in the Tunisian traditional medicine. The study was undertaken to extract and determine the essential oil chemical composition of Clematis flammula aerial parts and to assess the potential of anemonin in wound healing on mechanically wounded wistar rats. The essential oil was obtained by hydrodistillation and analyzed by GC-MS. Anemonin was isolated and then incorporated as active in a cream for which the cytotoxicity was evaluated by methyl thiazolyl tetrazolium (MTT)-based colorimetric assay. Then, its potential in wound healing on mechanically wounded wistar rats was assessed. The GC-MS analysis showed that the major compound was protoanemonin (86.74%) which spontaneously dimerised in part to form the anemonin. The wound healing activity of anemonin cream exhibited a non toxic potential of anemonin at a concentration of 25 µg/mL with a cell migration efficiency that reaches more than 80% after 48 hours of treatment. Wound healing efficiency was evaluated by monitoring morphological and skin histological analyses. Comparable wound surface reduction of the group treated by anemonin cream (p ≥ 0.05) when compared to the reference treated group. The skin histological analysis showed the completely wound closure. Antioxidant activity was assessed by the malondialdehyde (MDA) rates and antioxidant enzymes (glutathione peroxidase (GPx) and catalase) determination. The results provided strong support for the effective wound healing activity of anemonin cream, making it a promising candidate as a therapeutic agent in tissue repairing processes.


Assuntos
Clematis/química , Furanos/isolamento & purificação , Furanos/farmacologia , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Cicatrização/efeitos dos fármacos , Administração Tópica , Animais , Antioxidantes/metabolismo , Catalase/metabolismo , Feminino , Furanos/administração & dosagem , Cromatografia Gasosa-Espectrometria de Massas , Glutationa Peroxidase/metabolismo , Malondialdeído/metabolismo , Óleos Voláteis/administração & dosagem , Ratos Wistar , Pele/metabolismo , Pele/patologia , Creme para a Pele , Estimulação Química , Tunísia
19.
Biochem Biophys Res Commun ; 507(1-4): 155-160, 2018 12 09.
Artigo em Inglês | MEDLINE | ID: mdl-30415772

RESUMO

Brown adipose tissue (BAT) is the site of non-shivering thermogenesis in mammals, wherein energy is dissipated as heat. We observed that aqueous extract of black sesame seed triggers an increase in the expression of Uncoupling Protein 1 (UCP1) in brown adipocytes from mice. The active component from the extract was purified and identified to be sesaminol diglucoside (SDG). SDG treatment decreased mass of white fat pads and serum glucose levels and increased UCP1 levels in BAT thereby protecting mice against high fat induced weight gain. Further in silico and in vitro studies revealed that these effects are due to the agonist like behaviour of SDG towards beta 3 adrenergic receptors (ß3-AR). Together, our results suggest that SDG induces BAT mediated thermogenesis through ß3-AR and protects mice against diet-induced obesity.


Assuntos
Tecido Adiposo Marrom/fisiologia , Dioxóis/farmacologia , Furanos/farmacologia , Lignanas/farmacologia , Sementes/química , Sesamum/química , Termogênese/efeitos dos fármacos , Adipócitos Marrons/efeitos dos fármacos , Adipócitos Marrons/metabolismo , Tecido Adiposo Marrom/efeitos dos fármacos , Animais , Dieta Hiperlipídica , Dioxóis/isolamento & purificação , Furanos/isolamento & purificação , Lipídeos/química , Camundongos Endogâmicos C57BL , Extratos Vegetais/farmacologia , Receptores Adrenérgicos beta 3/metabolismo , Proteína Desacopladora 1/metabolismo , Ganho de Peso/efeitos dos fármacos
20.
Phytochemistry ; 156: 151-158, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30296708

RESUMO

Seven undescribed hydroxylated cassane-type furanoditerpenoids were isolated from pupal cases formed from the secretion/excretion of the larvae of the wild bruchid seed beetle Sulcobruchus sauteri in infested Caesalpinia decapetala seeds, and their structures were elucidated by interpreting their spectra. The hydroxylated furanoditerpenoids found in the pupal cases were not present in the seeds of the host plant. Caesalacetal and caesaljapin obtained from the intact seeds exhibited larvicidal activity against the larvae of Aedes albopictus, while the hydroxylated furanoditerpenoids isolated from the pupal cases were inactive. The larvae of S. sauteri are proposed to detoxify larvicidal diterpenoids that occur in the seeds of the host plant by regiospecific hydroxylation.


Assuntos
Caesalpinia/metabolismo , Diterpenos/metabolismo , Furanos/metabolismo , Pupa/metabolismo , Sementes/metabolismo , Animais , Caesalpinia/química , Besouros , Diterpenos/química , Diterpenos/isolamento & purificação , Furanos/química , Furanos/isolamento & purificação , Hidroxilação , Conformação Molecular , Pupa/química , Sementes/química
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