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1.
Molecules ; 26(15)2021 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-34361701

RESUMO

Arthritis is a chronic inflammatory disease accompanied by pathological reactions such as swelling, redness, fever, and pain in various joint areas. The drugs currently available to treat arthritis are associated with diverse side-effects. Therefore, there is a need for safer and more effective treatments to alleviate the inflammation of arthritis with fewer side-effects. In this study, a new sterol, Δ8(14)-ergostenol, was discovered, and its glycosides were synthesized and found to be more efficient in terms of synthesis or anti-inflammatory activity than either spinasterol or 5,6-dihydroergosterol is. Among these synthetic glycosides, galactosyl ergostenol inhibited the expression of inflammatory mediators in TNF-α-stimulated FLS and TNF-α-induced MMPs and collagen type II A1 degradation in human chondrocytes. These results suggest the new galactosyl ergostenol as a treatment candidate for arthritis.


Assuntos
Anti-Inflamatórios/farmacologia , Condrócitos/efeitos dos fármacos , Ergosterol/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Glicosídeos/farmacologia , Sinoviócitos/efeitos dos fármacos , Anti-Inflamatórios/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Condrócitos/citologia , Condrócitos/metabolismo , Colágeno Tipo II/genética , Colágeno Tipo II/metabolismo , Ergosterol/química , Glicosídeos/síntese química , Humanos , Inflamação/prevenção & controle , Interleucina-1beta/genética , Interleucina-1beta/metabolismo , Interleucina-6/genética , Interleucina-6/metabolismo , Interleucina-8/genética , Interleucina-8/metabolismo , Metaloproteinases da Matriz/genética , Metaloproteinases da Matriz/metabolismo , Modelos Biológicos , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/metabolismo , Transdução de Sinais , Sinoviócitos/citologia , Sinoviócitos/metabolismo , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/farmacologia
2.
Molecules ; 26(16)2021 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-34443502

RESUMO

Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Their effect was dose and time-dependent with varied potency, the highest against prostate PC3 and melanoma WM793, where IC50 was lower than the reference drug doxorubicin. Structure-activity relationship is briefly discussed.


Assuntos
Chenopodiaceae/química , Glicosídeos/farmacologia , Triterpenos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Espectroscopia de Prótons por Ressonância Magnética , Triterpenos/química , Triterpenos/isolamento & purificação
3.
Molecules ; 26(16)2021 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-34443430

RESUMO

Parkinson's disease (PD) is a currently incurable neurodegenerative disorder characterized by the loss of dopaminergic (DAergic) neurons in the substantia nigra pars compacta and α-synuclein aggregation. Accumulated evidence indicates that the saponins, especially from ginseng, have neuroprotective effects against neurodegenerative disorders. Interestingly, saponin can also be found in marine organisms such as the sea cucumber, but little is known about its effect in neurodegenerative disease, including PD. In this study, we investigated the anti-Parkinson effects of frondoside A (FA) from Cucumaria frondosa and ginsenoside Rg3 (Rg3) from Panax notoginseng in C. elegans PD model. Both saponins were tested for toxicity and optimal concentration by food clearance assay and used to treat 6-OHDA-induced BZ555 and transgenic α-synuclein NL5901 strains in C. elegans. Treatment with FA and Rg3 significantly attenuated DAergic neurodegeneration induced by 6-OHDA in BZ555 strain, improved basal slowing rate, and prolonged lifespan in the 6-OHDA-induced wild-type strain with downregulation of the apoptosis mediators, egl-1 and ced-3, and upregulation of sod-3 and cat-2. Interestingly, only FA reduced α-synuclein aggregation, rescued lifespan in NL5901, and upregulated the protein degradation regulators, including ubh-4, hsf-1, hsp-16.1 and hsp-16.2. This study indicates that both FA and Rg3 possess beneficial effects in rescuing DAergic neurodegeneration in the 6-OHDA-induced C. elegans model through suppressing apoptosis mediators and stimulating antioxidant enzymes. In addition, FA could attenuate α-synuclein aggregation through the protein degradation process.


Assuntos
Caenorhabditis elegans/fisiologia , Ginsenosídeos/farmacologia , Glicosídeos/farmacologia , Doença de Parkinson/patologia , Triterpenos/farmacologia , Animais , Animais Geneticamente Modificados , Apoptose/efeitos dos fármacos , Caenorhabditis elegans/efeitos dos fármacos , Caenorhabditis elegans/genética , Proteínas de Caenorhabditis elegans/metabolismo , Modelos Animais de Doenças , Neurônios Dopaminérgicos/efeitos dos fármacos , Neurônios Dopaminérgicos/patologia , Regulação da Expressão Gênica/efeitos dos fármacos , Ginsenosídeos/química , Ginsenosídeos/toxicidade , Glicosídeos/química , Glicosídeos/toxicidade , Longevidade/efeitos dos fármacos , Degeneração Neural/complicações , Degeneração Neural/patologia , Oxidopamina , Doença de Parkinson/complicações , Proteólise/efeitos dos fármacos , Triterpenos/química , Triterpenos/toxicidade , alfa-Sinucleína/metabolismo
4.
Phytochemistry ; 191: 112896, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34371301

RESUMO

Feline calicivirus is one of the surrogate viruses of human norovirus. This study aimed to identify virucidal compounds, chemical constituents of plants from the genus Dracocephalum, which are rich in flavonoids and phenylpropanoid oligomers. Four undescribed compounds, including a flavanone glucoside, two stilbenoid glycosides, and a phenylpropanoid amide glycoside, as well as 17 known compounds, were isolated from the Mongolian plants Dracocephalum fruticulosum Stephan ex Willd., and D. nutans L. belonging to the family Lamiaceae. The structures of the compounds were determined based on NMR, MS, and electronic CD spectroscopic data. In addition to these 21 compounds, 15 previously reported compounds from D. foetidum Bunge in C.F. von Ledebour were included, and a total of 36 compounds were evaluated for their virucidal activities against feline calicivirus. Some of the flavanone glycosides and phenylpropanoid oligomers showed virucidal activities, and their structural features are discussed. The findings suggest that isosakuranetin glycosides and phenylpropanoid oligomers may have the potential for norovirus inactivation.


Assuntos
Calicivirus Felino , Flavanonas , Lamiaceae , Animais , Gatos , Cinamatos , Depsídeos , Flavanonas/farmacologia , Glicosídeos/farmacologia
5.
Phytochemistry ; 191: 112906, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34390889

RESUMO

Twenty-five steroidal glycosides including eight undescribed compounds which were named as polygonatumosides H-O, were isolated from the 70 % EtOH extract of rhizomes of Polygonatum odoratum (Mill.) Druce (Asparagaceae). Their structures were elucidated by extensive spectroscopic analyses and chemical methods. The isolated compounds were evaluated cytotoxicity against three human cancer cell lines: human non-small cell lung cancer (A549), human epithelial colorectal adenocarcinoma (Caco2), and human hepatocellular carcinoma (HepG2) cells. Five compounds showed cytotoxicity against these cell lines with IC50 values in the range of 1.7-30.8 µM.


Assuntos
Carcinoma Pulmonar de Células não Pequenas , Neoplasias Pulmonares , Polygonatum , Células CACO-2 , Glicosídeos/farmacologia , Humanos , Estrutura Molecular
6.
Molecules ; 26(16)2021 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-34443633

RESUMO

Pseudostellaria heterophylla is used in China not only as a functional food but also as an herb to tonify the spleen, enhance immunity, and treat palpitation. Our previous investigation showed that a fraction enriched in glycosides obtained from the roots of P. heterophylla possessed pronounced protective effects on H9c2 cells against CoCl2-induced hypoxic injury. However, the active compounds responsible for the observed effects were still unknown. In the current investigation, pseudosterins A-C (1-3), three new alkaloids with a 1-ethyl-3-formyl-ß-carboline skeleton, together with polydatin, have been isolated from the active fraction. Their structures were elucidated on the basis of spectroscopic analysis and quantum chemical calculations. The four compounds showed cardioprotective effects against sodium hydrosulfite-induced hypoxia-reoxygenation injury in H9c2 cells, with the three alkaloids being more potent. This is also the first report of alkaloids with a ß-carboline skeleton isolated from P. heterophylla as cardioprotective agents.


Assuntos
Alcaloides/farmacologia , Carbolinas/farmacologia , Cardiotônicos/farmacologia , Caryophyllaceae/química , Extratos Vegetais/farmacologia , Alcaloides/química , Animais , Carbolinas/química , Cardiotônicos/química , Linhagem Celular , China , Glicosídeos/química , Glicosídeos/farmacologia , Hipóxia/tratamento farmacológico , Extratos Vegetais/química , Raízes de Plantas/química , Ratos
7.
Zhongguo Zhong Yao Za Zhi ; 46(11): 2746-2752, 2021 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-34296571

RESUMO

As a traditional Chinese medicinal material, Lonicera japonica has a long medicinal history. The chemical constituents of Lonicera japonica are complex, mainly including iridoid glycosides, flavonoids, triterpenes, organic acids and volatile oil. Iridoid glycosides account for a higher proportion. In addition, modern pharmacological studies have shown that the iridoid glycosides have many pharmacological activities such as antivirus, anti-inflammation, anti-tumor, liver protection and lowering blood sugar. This review intends to systematically summarize the iridoid glycosides identified from Lonicera japonica and their pharmacological activities by searc-hing Chinese and English databases, in order to provide a reference for the further development and utilization of Lonicera japonica and for the improvement of quality standards of medicinal materials.


Assuntos
Lonicera , Anti-Inflamatórios , Flavonoides , Glicosídeos/farmacologia , Glicosídeos Iridoides/farmacologia , Extratos Vegetais
8.
Phytochemistry ; 190: 112893, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34332297

RESUMO

Four previously undescribed iridoid glycosides, including two bis-iridoid glycosides, and three undescribed lignans, together with 16 known analogues, were isolated from the fruits of Gardenia jasminoides Eills. Their structures were elucidated on basis of spectroscopic methods, and the absolute configurations of three of the unknown compounds were determined by interpretation of their electronic circular dichroic (ECD) and [α] [Formula: see text] data. The α-glucosidase inhibitory effects of the isolated compounds were evaluated and all the compounds exhibited slightly inhibitory activity with the values of IC50 greater than 50 µM.


Assuntos
Gardenia , Lignanas , Frutas , Glicosídeos/farmacologia , Glicosídeos Iridoides/farmacologia , Lignanas/farmacologia , Extratos Vegetais
9.
J Asian Nat Prod Res ; 23(8): 724-730, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34253100

RESUMO

Three new flavonoid glycosides, embeliaflavosides A-C (1-3), together with eight known flavonoid glycosides (4-11), were isolated from the fruits of Embelia ribes. Their structures were established based on the analyses of spectroscopic data. Compounds 1-11 were evaluated for antioxidant and α-glucosidase inhibitory activities. The results revealed that compounds 1-11 owned significant ABTS radical scavenging activity with IC50 values of 2.52-9.78 µM, and DPPH scavenging activity with IC50 values of 7.56-26.47 µM, respectively. However, α-glucosidase inhibition assay indicated that all the isolates were inactive.[Formula: see text].


Assuntos
Embelia , Ribes , Antioxidantes/farmacologia , Embelia/metabolismo , Flavonoides/farmacologia , Frutas , Inibidores de Glicosídeo Hidrolases/farmacologia , Glicosídeos/farmacologia , Estrutura Molecular , Extratos Vegetais , Ribes/metabolismo , alfa-Glucosidases/metabolismo
10.
Molecules ; 26(13)2021 Jun 22.
Artigo em Inglês | MEDLINE | ID: mdl-34206308

RESUMO

Horse chestnut (Aesculus hippocastanum L.)-derived drugs have shown their potential in biomedical applications. The seed of A. hippocastanum contains various kinds of chemical compounds including phenolics, flavonoids, coumarins, and triterpene saponins. Here, we investigated the chemical components in A. hippocastanum L. grown in Uzbekistan, which has not yet been studied in detail. We identified 30 kinds of triterpene saponins in an extract of A. hippocastanum L. Classifying extracted saponins into eight fractions, we next studied the hypoglycemic and the anti-inflammatory activities of escin and its derivatives through in vivo experiments. We came by data indicating the highest (SF-1 and SF-2) and the lowest (SF-5 and SF-8) antidiabetic and anti-inflammatory effects of those eight fractions. These results imply the prospective use of A. hippocastanum L. grown in Uzbekistan in the production of pharmaceutical drugs to treat diabetes and inflammation.


Assuntos
Aesculus/química , Anti-Inflamatórios , Glicosídeos , Hipoglicemiantes , Triterpenos , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Feminino , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Masculino , Ratos , Ratos Wistar , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Uzbequistão
11.
Molecules ; 26(12)2021 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-34208231

RESUMO

Phytochemical investigation on the n-BuOH-soluble fraction of the aerial parts of Epimedium koreanum using the PCSK9 mRNA monitoring assay led to the identification of four previously undescribed acylated flavonoid glycosides and 18 known compounds. The structures of new compounds were elucidated by NMR, MS, and other chemical methods. All isolated compounds were tested for their inhibitory activity against PCSK9 mRNA expression in HepG2 cells. Of the isolates, compounds 6, 7, 10, 15, and 17-22 were found to significantly inhibit PCSK9 mRNA expression. In particular, compound 7 was shown to increase LDLR mRNA expression. Thus, compound 7 may potentially increase LDL uptake and lower cholesterol levels in the blood.


Assuntos
Epimedium/química , Flavonoides/química , Glicosídeos/química , Pró-Proteína Convertase 9/antagonistas & inibidores , RNA Mensageiro/antagonistas & inibidores , Linhagem Celular Tumoral , Epimedium/metabolismo , Flavonoides/metabolismo , Flavonoides/farmacologia , Glicosídeos/metabolismo , Glicosídeos/farmacologia , Humanos , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Prenilação , Pró-Proteína Convertase 9/metabolismo , Receptores de LDL/agonistas
12.
Int J Mol Sci ; 22(13)2021 Jun 27.
Artigo em Inglês | MEDLINE | ID: mdl-34199016

RESUMO

Paeonia suffruticosa is a magnificent and long-lived woody plant that has traditionally been used to treat various diseases including inflammatory, neurological, cancer, and cardiovascular diseases. In the present study, we demonstrated the biological mechanisms of paeonoside (PASI) isolated from the dried roots of P. suffruticosa in pre-osteoblasts. Herein, we found that PASI has no cytotoxic effects on pre-osteoblasts. Migration assay showed that PASI promoted wound healing and transmigration in osteoblast differentiation. PASI increased early osteoblast differentiation and mineralized nodule formation. In addition, PASI enhanced the expression of Wnt3a and bone morphogenetic protein 2 (BMP2) and activated their downstream molecules, Smad1/5/8 and ß-catenin, leading to increases in runt-related transcription factor 2 (RUNX2) expression during osteoblast differentiation. Furthermore, PASI-mediated osteoblast differentiation was attenuated by inhibiting the BMP2 and Wnt3a pathways, which was accompanied by reduction in the expression of RUNX2 in the nucleus. Taken together, our findings provide evidence that PASI enhances osteoblast differentiation and mineralized nodules by regulating RUNX2 expression through the BMP2 and Wnt3a pathways, suggesting a potential role for PASI targeting osteoblasts to treat bone diseases including osteoporosis and periodontitis.


Assuntos
Calcificação Fisiológica/efeitos dos fármacos , Diferenciação Celular/efeitos dos fármacos , Glicosídeos/farmacologia , Osteoblastos/citologia , Osteoblastos/efeitos dos fármacos , Osteoblastos/metabolismo , Extratos Vegetais/farmacologia , Biomarcadores , Proteína Morfogenética Óssea 2/metabolismo , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Subunidade alfa 1 de Fator de Ligação ao Core/metabolismo , Glicosídeos/química , Humanos , Imuno-Histoquímica , Espectroscopia de Ressonância Magnética/efeitos adversos , Osteogênese/efeitos dos fármacos , Extratos Vegetais/química , Via de Sinalização Wnt
13.
Int J Mol Sci ; 22(14)2021 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-34299326

RESUMO

Ziziphus jujuba extracts possess a broad spectrum of biological activities, such as antioxidant and anticancer activities in melanoma cancers. Nevertheless, the compounds contain high antioxidant capacities and anticancer activities in melanoma cells, shown to be effective in hyperpigmentation disorders, but whether flavonoid glycosides from Z. jujuba regulate anti-melanogenesis remains unclear. In this study, we evaluated the anti-melanogenic activity of five flavonoid glycosides from Z. jujuba var. inermis (Bunge) Rehder seeds, including jujuboside A (JUA), jujuboside B (JUB), epiceanothic acid (EPA), betulin (BTL), and 6'''-feruloylspinosin (FRS), in B16F10 melanoma cells and zebrafish larvae. According to our results, JUB, EPA, and FRS potently inhibited α-melanocyte-stimulating hormone (α-MSH)-induced melanogenesis and prevented hyperpigmentation in zebrafish larvae. In particular, under α-MSH-stimulated conditions, FRS most significantly inhibited α-MSH-induced intracellular and extracellular melanin content in B16F10 melanoma cells. Additionally, JUB, EPS, and FRS remarkably downregulated melanogenesis in α-MSH-treated zebrafish larvae, with no significant change in heart rate. Neither JUA nor BTA were effective in downregulating melanogenesis in B16F10 melanoma cells and zebrafish larvae. Furthermore, JUB, EPA, and FRS directly inhibited in vitro mushroom tyrosinase enzyme activity. JUB, EPA, and FRS also downregulated cyclic adenosine monophosphate (cAMP) levels and the phosphorylation of cAMP-response element-binding protein (CREB), and subsequent microphthalmia transcription factor (MITF) and tyrosinase expression. In conclusion, this study demonstrated that JUB, EPA, and FRS isolated from Z. jujuba var. inermis (Bunge) Rehder seeds exhibit potent anti-melanogenic properties by inhibition of the cAMP-CERB-MITF axis and consequent tyrosinase activity.


Assuntos
Flavonoides/farmacologia , Glicosídeos/farmacologia , Ziziphus/metabolismo , alfa-MSH/metabolismo , Animais , Antioxidantes/farmacologia , AMP Cíclico/metabolismo , Proteínas Quinases Dependentes de AMP Cíclico/metabolismo , Flavonoides/isolamento & purificação , Glicosídeos/isolamento & purificação , Larva , Melaninas/metabolismo , Melanoma/tratamento farmacológico , Melanoma/metabolismo , Melanoma Experimental , Fosforilação/efeitos dos fármacos , Extratos Vegetais/farmacologia , Sementes/metabolismo , Transdução de Sinais/efeitos dos fármacos , Peixe-Zebra , alfa-MSH/antagonistas & inibidores
14.
Molecules ; 26(14)2021 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-34299396

RESUMO

In this study, two previously undescribed diterpenoids, (5R,10S,16R)-11,16,19-trihydroxy-12-O-ß-d-glucopyranosyl-(1→2)-ß-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-3,8,11,13-abietatetraene-7-one (1) and (5R,10S,16R)-11,16-dihydroxy-12-O-ß-d-glucopyranosyl-(1→2)-ß-d-glucopyranosyl-17(15→16),18(4→3)-diabeo-4-carboxy-3,8,11,13-abietatetraene-7-one (2), and one known compound, the C13-nor-isoprenoid glycoside byzantionoside B (3), were isolated from the leaves of Clerodendrum infortunatum L. (Lamiaceae). Structures were established based on spectroscopic and spectrometric data and by comparison with literature data. The three terpenoids, along with five phenylpropanoids: 6'-O-caffeoyl-12-glucopyranosyloxyjasmonic acid (4), jionoside C (5), jionoside D (6), brachynoside (7), and incanoside C (8), previously isolated from the same source, were tested for their in vitro antidiabetic (α-amylase and α-glucosidase), anticancer (Hs578T and MDA-MB-231), and anticholinesterase activities. In an in vitro test against carbohydrate digestion enzymes, compound 6 showed the most potent effect against mammalian α-amylase (IC50 3.4 ± 0.2 µM) compared to the reference standard acarbose (IC50 5.9 ± 0.1 µM). As yeast α-glucosidase inhibitors, compounds 1, 2, 5, and 6 displayed moderate inhibitory activities, ranging from 24.6 to 96.0 µM, compared to acarbose (IC50 665 ± 42 µM). All of the tested compounds demonstrated negligible anticholinesterase effects. In an anticancer test, compounds 3 and 5 exhibited moderate antiproliferative properties with IC50 of 94.7 ± 1.3 and 85.3 ± 2.4 µM, respectively, against Hs578T cell, while the rest of the compounds did not show significant activity (IC50 > 100 µM).


Assuntos
Abietanos/química , Antineoplásicos/farmacologia , Inibidores da Colinesterase/farmacologia , Clerodendrum/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Glicosídeos/farmacologia , Folhas de Planta/química , Humanos , Neoplasias/tratamento farmacológico , Células Tumorais Cultivadas , alfa-Amilases/antagonistas & inibidores
15.
Fitoterapia ; 153: 104997, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34302917

RESUMO

Eight new stilbene dimer xylosides (1-8) and one new flavanol (9), along with seven known ones (10-16) were isolated from the roots of Lysidice rhodostegia. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HR-ESI-MS, 1D and 2D NMR), ECD calculations and acid hydrolysis. Compounds 1-16 were evaluated for their antioxidant activities using DPPH radical-scavenging assay. Especially, compounds 9 and 10 exhibited stronger antioxidant effects than the positive control (vitamin E), with IC50 values of 9.57 ± 1.30 and 13.60 ± 1.47 µM, respectively.


Assuntos
Antioxidantes/farmacologia , Fabaceae/química , Glicosídeos/farmacologia , Polifenóis/farmacologia , Estilbenos/farmacologia , Antioxidantes/isolamento & purificação , China , Glicosídeos/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Polifenóis/isolamento & purificação , Estilbenos/isolamento & purificação
16.
Fitoterapia ; 153: 104966, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34144143

RESUMO

Euphorboside A (1), an unusual meroterpenoid glycoside featuring the incorporation of an acylphloroglucinol moiety into a humulene skeleton to form a 6/6/11 ring system, was isolated from the roots of Euphorbia kansuensis. Its structure was elucidated by extensive spectroscopic analysis, chemical methods, and ECD calculations. Compound 1 was screened for the cytotoxicity against nine cancer cell lines, and 1 showed marked inhibitory activities against human colon cancer RKO and human breast cancer MDA-MB-231 cell lines with IC50 values of 3.70 and 4.15 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Euphorbia/química , Glicosídeos/farmacologia , Sesquiterpenos Monocíclicos/química , Floroglucinol/química , Terpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Glicosídeos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Terpenos/isolamento & purificação
17.
Int J Mol Sci ; 22(9)2021 May 09.
Artigo em Inglês | MEDLINE | ID: mdl-34065110

RESUMO

The fungal toxin fusicoccin (FC) induces rapid cell elongation, proton extrusion and plasma membrane hyperpolarization in maize coleoptile cells. Here, these three parameters were simultaneously measured using non-abraded and non-peeled segments with the incubation medium having access to their lumen. The dose-response curve for the FC-induced growth was sigmoidal shaped with the maximum at 10-6 M over 10 h. The amplitudes of the rapid growth and proton extrusion were significantly higher for FC than those for indole-3-acetic acid (IAA). The differences between the membrane potential changes that were observed in the presence of FC and IAA relate to the permanent membrane hyperpolarization for FC and transient hyperpolarization for IAA. It was also found that the lag times of the rapid growth, proton extrusion and membrane hyperpolarization were shorter for FC compared to IAA. At 30 °C, the biphasic kinetics of the IAA-induced growth rate could be changed into a monophasic (parabolic) one, which is characteristic for FC-induced rapid growth. It has been suggested that the rates of the initial phase of the FC- and IAA-induced growth involve two common mechanisms that consist of the proton pumps and potassium channels whose contribution to the action of both effectors on the rapid growth is different.


Assuntos
Cotilédone/efeitos dos fármacos , Cotilédone/fisiologia , Glicosídeos/farmacologia , Potenciais da Membrana/efeitos dos fármacos , Desenvolvimento Vegetal/efeitos dos fármacos , Prótons , Zea mays/efeitos dos fármacos , Zea mays/fisiologia , Concentração de Íons de Hidrogênio , Cinética , Reguladores de Crescimento de Plantas/metabolismo , Temperatura
18.
Molecules ; 26(11)2021 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-34070943

RESUMO

The medicinal plant noni (Morinda citrifolia) is widely dispersed throughout Southeast Asia, the Caribbean, and Australia. We previously reported that fermented Noni could alleviate atopic dermatitis (AD) by recovering Th1/Th2 immune balance and enhancing skin barrier function induced by 2,4-dinitrochlorobenzene. Noni has a high deacetylasperulosidic acid (DAA) content, whose concentration further increased in fermented noni as an iridoid constituent. This study aimed to determine the anti-AD effects and mechanisms of DAA on HaCaT, HMC-1, and EOL-1 cells. DAA inhibited the gene expression and secretion of AD-related cytokines and chemokines including interleukin (IL)-1ß, IL-4, IL-6, IL-8, IL-25, IL-33, thymic stromal lymphopoietin, tumor necrosis factor-alpha, monocyte chemoattractant protein-1, thymus and activation-regulated chemokine, macrophage-derived chemokine, and regulated upon activation, normal T cell expressed and secreted, in all cells, and inhibited histamine release in HMC-1 cells. DAA controlled mitogen-activated protein kinase phosphorylation levels and the translocation of nuclear factor-kappa light chain enhancer of activated B cells into the nucleus by inhibiting IκBα decomposition in all the cells. Furthermore, DAA increased the expression of proteins involved in skin barrier functions such as filaggrin and involucrin in HaCaT cells. These results confirmed that DAA could relieve AD by controlling immune balance and recovering skin barrier function.


Assuntos
Dermatite Atópica/tratamento farmacológico , Glicosídeos/farmacologia , Linhagem Celular , Quimiocinas/imunologia , Quimiocinas/metabolismo , Citocinas/imunologia , Citocinas/metabolismo , Dermatite Atópica/patologia , Eczema/tratamento farmacológico , Eczema/patologia , Glicosídeos/metabolismo , Humanos , Queratinócitos/efeitos dos fármacos , Morinda/metabolismo , Extratos Vegetais/farmacologia , Pele/metabolismo , Equilíbrio Th1-Th2/efeitos dos fármacos
19.
Biomolecules ; 11(5)2021 05 17.
Artigo em Inglês | MEDLINE | ID: mdl-34067705

RESUMO

Tripterygium wilfordii glycosides (TWG) is a traditional Chinese medicine with effectiveness against rheumatoid arthritis (RA), supported by numerous clinical trials. Lipid mediators (LM) are biomolecules produced from polyunsaturated fatty acids mainly by cyclooxygenases (COX) and lipoxygenases (LOX) in complex networks which regulate inflammation and immune responses and are strongly linked to RA. The mechanism by which TWG affects LM networks in RA treatment remains elusive. Employing LM metabololipidomics using ultra-performance liquid chromatography-tandem mass spectrometry revealed striking modulation of LM pathways by TWG in human monocyte-derived macrophage (MDM) phenotypes. In inflammatory M1-MDM, TWG (30 µg/mL) potently suppressed agonist-induced formation of 5-LOX products which was confirmed in human PMNL and traced back to direct inhibition of 5-LOX (IC50 = 2.9 µg/mL). TWG also efficiently blocked thromboxane formation in M1-MDM without inhibiting other prostanoids and COX enzymes. Importantly, in anti-inflammatory M2-MDM, TWG (30 µg/mL) induced pronounced formation of specialized pro-resolving mediators (SPM) and related 12/15-LOX-derived SPM precursors, without COX and 5-LOX activation. During MDM polarization, TWG (1 µg/mL) decreased the capacity to generate pro-inflammatory 5-LOX and COX products, cytokines and markers for M1 phenotypes. Together, suppression of pro-inflammatory LM but SPM induction may contribute to the antirheumatic properties of TWG.


Assuntos
Antirreumáticos/administração & dosagem , Araquidonato 5-Lipoxigenase/metabolismo , Glicosídeos/farmacologia , Prostaglandina-Endoperóxido Sintases/metabolismo , Tripterygium/química , Células A549 , Antirreumáticos/farmacologia , Cromatografia Líquida de Alta Pressão , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Imunidade Inata/efeitos dos fármacos , Lipidômica/métodos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Prostaglandinas/metabolismo , Espectrometria de Massas em Tandem , Tromboxanos
20.
Biomolecules ; 11(5)2021 05 05.
Artigo em Inglês | MEDLINE | ID: mdl-34063021

RESUMO

Dietary supplements based on Teucrium chamaedrys L. subsp. chamaedrys aerial parts were banned, due to the hepatotoxicity of furan-containing neo-clerodane constituents. Indeed, the plant leaf content in phenolic compounds could be further exploited for their antioxidant capability. Accordingly, bio-guided fractionation strategies have been applied, obtaining seven partially purified extracts. These latter were chemically investigated through 1D and 2D NMR techniques and tested for their antiradical, reducing and cytotoxic capability. Data acquired highlighted that, through a simple phytochemical approach, a progressive neo-clerodane depletion occurred, while maximizing phenylethanoid glycosides in alcoholic fractions. Thus, although the plant cannot be used as a botanical remedy as such, it is suggested as a source of healthy compounds, pure or in mixture, to be handled in pharmaceutical, nutraceutical and/or cosmeceutical sectors.


Assuntos
Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Glicosídeos/isolamento & purificação , Metabolômica/métodos , Fenóis/isolamento & purificação , Teucrium/química , Células A549 , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Fracionamento Químico , Diterpenos Clerodânicos/isolamento & purificação , Diterpenos Clerodânicos/toxicidade , Glicosídeos/química , Glicosídeos/farmacologia , Células HeLa , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Fenóis/química , Fenóis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química
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