Your browser doesn't support javascript.
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 2.966
Filtrar
1.
J Agric Food Chem ; 68(7): 2041-2053, 2020 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-31967813

RESUMO

Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4-seco-dammarane triterpenoid saponins (1-11), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7, 8, 10, and 11 showed strong inhibition on nitric oxide (NO) productions, with IC50 values ranging from 8.23 to 11.23 µM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure-activity relationships of the isolates were investigated. The results suggest that 3,4-seco-dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.


Assuntos
Anti-Inflamatórios/farmacologia , Juglandaceae/química , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Triterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Interleucina-6/genética , Interleucina-6/imunologia , Macrófagos/efeitos dos fármacos , Camundongos , NF-kappa B/genética , NF-kappa B/imunologia , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/imunologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Células RAW 264.7 , Saponinas/química , Saponinas/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/imunologia
2.
Planta Med ; 86(1): 70-77, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31671467

RESUMO

Four new barringtogenol C-type triterpenoid saponins, namely acerplatanosides A - D (1: -4: ), along with 22 known compounds (5: -26: ), were isolated from the stem bark of Norway maple (Acer platanoides). Their structures were elucidated on the basis of comprehensive spectroscopic analyses and chemical hydrolysis. This is the first report of triterpenoid saponins isolated from Norway maple. Compounds 1, 3: , and 4: showed cytotoxicity against 4 human cancer cell lines with IC50 values ranging from 9.4 to 39.5 µM.


Assuntos
Acer/química , Antineoplásicos Fitogênicos/isolamento & purificação , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Casca de Planta/química , Saponinas/química , Triterpenos/química
3.
Food Chem ; 309: 125786, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-31704078

RESUMO

The ultrasonic-assisted extraction of total saponins from alfalfa leaves was optimised by the simultaneous maximization of the yield and bioaccessibility as a factor with increasingly great relevance in the biological activity by Response Surface Methodology. The kinetics of total saponins and bioaccessibility were investigated for the optimum ultrasound-assisted method compared to conventional method by the pseudo-first order model. The optimum extraction conditions were of solvent/raw material ratio of 11.4 mL/g, extraction time of 2.84 h, extraction temperature of 76.8 °C, ultrasound power of 112.0 w and ethanol concentration of 78.2%. The yield of total saponins and bioaccessibility was 1.61 and 18.6%, respectively. The yield rate constant for the ultrasound extraction was almost two times more than that of the heat-reflux method. Ultrasonic-assisted extraction, comparing to conventional method, had greater efficiency for the extraction yield and bioaccessibility of total saponins.


Assuntos
Medicago sativa/química , Saponinas/análise , Sonicação , Etanol/química , Cinética , Medicago sativa/metabolismo , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Saponinas/isolamento & purificação , Solventes/química
4.
Food Chem ; 303: 125394, 2020 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-31473455

RESUMO

A simple and effective vesicle based ultrasonic-assisted extraction (UAE) method was developed for extraction of active compounds in functional food. The target analytes were determined by ultra-high performance liquid chromatography with ultraviolet detector. Surfactant vesicle was adopted as extraction solvent. Different operating conditions including the type and concentration of vesicle, extraction time and solid to liquid ratio were investigated by single-factor experiments and response surface methodology. Optimized experimental conditions were 1% (w/v) of DTAB/SDS vesicle, 20 min of extraction time and 160 mg/mL of solid to liquid ratio. The proposed method provided good linearity in the linear range of 10-1000 µg/mL with regression coefficients larger than 0.999, low limits of detection of 27.64-55.67 ng/mL, good precision with relative standard deviations below 0.35%, and satisfactory recoveries of 83.84-90.92% for tested saponins. Consequently, the proposed vesicle based UAE method was well suited for the extraction of saponins in Panax notoginseng.


Assuntos
Fracionamento Químico/métodos , Panax notoginseng/química , Saponinas/isolamento & purificação , Ultrassom , Cromatografia Líquida de Alta Pressão , Saponinas/análise
5.
Phytochemistry ; 169: 112162, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31627115

RESUMO

Twelve undescribed triterpenoid pentacyclic glycosides, medicagenic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-[ß-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-3,4-O-diacetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[2-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[3-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[4-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[ß-D-glucopyranosyl-(1 → 2)]-[ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid), zanhic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}2ß,3ß,16α-trihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-ß-D-fucopyranosyl-(1→)}-2ß,3ß,16α-trihydroxyolean-12-ene-23,28-dioic acid), 29-hydroxy-medicagenic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß,29ß-trihydroxyolean-12-ene-23,28-dioic acid) and herniaric acid (28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-18-ene-23,28-dioic acid) were isolated from the whole plant extract of Herniaria glabra L. (Caryophyllaceae), wild growing in the Ukraine. In addition, five known triterpenoid saponins; i.e. herniariasaponins 1, 4, 5, 6, and 7 were also isolated. Their structures were elucidated by HRESIMS, 1D and 2D NMR spectroscopy, as well as by comparison with the literature data. Twelve herniariasaponins, the purified crude extract, and the saponin fraction were evaluated in vitro for their xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity. Moreover, herniariasaponins 4, 5, and 7 were screened for their cholinesterase inhibitory potential. As a result, no or low inhibition towards the mentioned enzymes was observed.


Assuntos
Caryophyllaceae/química , Inibidores Enzimáticos/farmacologia , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Animais , Colinesterases/metabolismo , Colagenases/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Conformação Molecular , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Elastase Pancreática/antagonistas & inibidores , Elastase Pancreática/metabolismo , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Saponinas/química , Saponinas/isolamento & purificação , Estereoisomerismo , Ucrânia , Xantina Oxidase/antagonistas & inibidores , Xantina Oxidase/metabolismo
6.
Fitoterapia ; 139: 104404, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31676394

RESUMO

Five new cucurbitane-type triterpenoid saponins Xuedanosides A-E (1-5) were isolated from the medicinal plant Hemsleya amabilis Diels by silica gel column, octadecylsilyl (ODS) column, and pre-HPLC techniques. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Separated compounds were evaluated for their cytotoxic activity in HeLa, HCT-8, MCF-7 and HepG2 human cancer cell lines, and compounds 1 and 2 showed significant effects against HeLa cells with IC50 values of 3.21 and 8.57 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cucurbitaceae/química , Tubérculos/química , Saponinas/farmacologia , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Glicosídeos , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação
7.
Fitoterapia ; 139: 104360, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31629869

RESUMO

Five new lignans mubiesins A - E (1-5), together with twenty-seven known compounds (6-32), were isolated from the cytotoxicity and anti-inflammation portions of Momordica cochinchinensis seeds which were widely used for various tumors and inflammations. Their structures were elucidated by extensive spectroscopic analyses (HR-MS, UV, CD, IR, 1D-NMR, and 2D-NMR). Their cytotoxic and anti-inflammatory activities were evaluated in vitro. Various lignans and saponins showed the significant activities, they could obviously inhibit the growth of tumor cells and the release of NO and TNF-α in RAW 264.7 cells induced by LPS.


Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Lignanas/farmacologia , Momordica/química , Saponinas/farmacologia , Sementes/química , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Saponinas/isolamento & purificação
8.
Phytochemistry ; 168: 112125, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31541772

RESUMO

Nine undescribed polyacetylated 18-norspirostanol saponins, trilliumosides A‒J, were obtained after a guidance based on a molecular networking strategy from the rhizomes of Trillium tschonoskii. Their structures were established by analysis of comprehensive spectroscopic data and chemical methods after their isolation in pure form. All isolated saponins were evaluated for their cytotoxicities against five selected human cancer cell lines (Huh7,A549,MCF-7,HepG2, and MOLT-4) and anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated NO production model in RAW264.7 macrophages. Trilliumoside D showed significant cytotoxicity against MOLT-4 cell lines with an IC50 value of 1.0 ±â€¯0.1 µM, whereas trilliumosides H and I displayed remarkable anti-inflammatory effects on NO production with inhibitory rates of 56.3 ±â€¯1.5 and 56.2 ±â€¯2.2% at the concentration of 1.0 µM, respectively.


Assuntos
Descoberta de Drogas , Saponinas/isolamento & purificação , Trillium/química , Acetilação , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Saponinas/química , Saponinas/farmacologia , Relação Estrutura-Atividade
9.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470638

RESUMO

Despite significant advances in the understanding, prevention, and treatment of cancer, the disease continues to affect millions of people worldwide. Chemoradiation therapy is a rational approach that has already proven beneficial for several malignancies. However, the existence of toxicity to normal tissue is a serious limitation of this treatment modality. The aim of the present study is to investigate the ability of polar steroids from starfish Patiria (=Asterina) pectinifera to enhance the efficacy of radiation therapy in colorectal carcinoma cells. The cytotoxic activity of polar steroids and X-ray radiation against DLD-1, HCT 116, and HT-29 cells was determined by an MTS assay. The effect of compounds, X-ray, and their combination on colony formation was studied using the soft agar method. The molecular mechanism of the radiosensitizing activity of asterosaponin P1 was elucidated by western blotting and the DNA comet assay. Polar steroids inhibited colony formation in the tested cells, and to a greater extent in HT-29 cells. Asterosaponin P1 enhanced the efficacy of radiation and, as a result, reduced the number and size of the colonies of colorectal cancer cells. The radiosensitizing activity of asterosaponin P1 was realized by apoptosis induction through the regulation of anti- and pro-apoptotic protein expression followed by caspase activation and DNA degradation.


Assuntos
Antineoplásicos/farmacologia , Apoptose/genética , Asterina/química , Regulação Neoplásica da Expressão Gênica , Compostos Policíclicos/farmacologia , Radiossensibilizantes/farmacologia , Saponinas/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Apoptose/efeitos da radiação , Caspase 3/genética , Caspase 3/metabolismo , Caspase 9/genética , Caspase 9/metabolismo , Linhagem Celular Tumoral , Terapia Combinada , Células HCT116 , Células HT29 , Humanos , Compostos Policíclicos/química , Compostos Policíclicos/isolamento & purificação , Radiossensibilizantes/química , Radiossensibilizantes/isolamento & purificação , Saponinas/química , Saponinas/isolamento & purificação , Ensaio Tumoral de Célula-Tronco , Raios X , Proteína X Associada a bcl-2/genética , Proteína X Associada a bcl-2/metabolismo , Proteína bcl-X/genética , Proteína bcl-X/metabolismo
10.
Fitoterapia ; 138: 104345, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31470063

RESUMO

The present study reports the phytochemical investigation of n-butanol-soluble extracts of Glechoma longituba. Five new oleanane-type triterpenoid saponins with an 11α, 12α-epoxy unit, named glechomanosides A - E, were isolated from the n-butanol soluble fraction of G. longituba. Their chemical structures were established using HRESIMS, IR, 1D NMR, and 2D NMR techniques. The compounds were all evaluated for their antithrombus activities by monitoring thrombin time (TT), prothrombin time (PT), activated partial thromboplastin time (APTT), and antiplatelet aggregation assays. These results suggest that G. longituba might be a candidate plant source of an interesting antithrombotic activity.


Assuntos
Plaquetas/efeitos dos fármacos , Lamiaceae/química , Ácido Oleanólico/análogos & derivados , Saponinas/farmacologia , Animais , China , Feminino , Masculino , Camundongos , Estrutura Molecular , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Tempo de Tromboplastina Parcial , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Agregação Plaquetária , Tempo de Protrombina , Coelhos , Saponinas/isolamento & purificação , Tempo de Trombina
11.
Fitoterapia ; 137: 104264, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31299275

RESUMO

Five undescribed triterpene-type saponins, parkibicolorosides A-E, a cassane-type diterpene, and a known trimethoxy benzene glucoside were isolated from the roots of Parkia bicolor A. Chev. Their structures were elucidated by different spectroscopic methods including 1D- and 2D-NMR experiments as well as HR-ESI-MS analysis. Their cytotoxic activity against the chronic myeloid leukemia (K562) cell line was evaluated. The monosaccharides saponins exhibited a moderate antiproliferative activity with IC50 ranging from 48.49 ±â€¯0.16 to 81.66 ±â€¯0.17 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Fabaceae/química , Raízes de Plantas/química , Saponinas/farmacologia , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Costa do Marfim , Humanos , Células K562 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação
12.
Food Chem Toxicol ; 132: 110659, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31276745

RESUMO

Subcritical water extraction (SWE) applied to analyses the bioactives from ashwagandha (W. somnifera) at varying temperature (100-200 °C) and extraction time (10-30 min). The effect of temperature and time has been investigated in terms of extraction yield (EY), total phenolic content (TPC), cytotoxicity, antioxidant, and enzyme inhibitory activities. The withanosides and withanolides responsible for various biological effects were quantified using high performance liquid chromatography (HPLC). The HPLC analysis revealed Withanoside V, Withanoside IV, 12-Deoxywithastramonolide, Withanolide A, and Withaferin A as a principle bioactive compounds in SWE, with high in concentration compared to microwave-assisted extraction (MAE), Soxhlet extraction (SE) and maceration (MC). For SWE the highest EY (65.6%; 200 °C for 30 min), TPC (82.5 mg GAE/g DE), antioxidant activity (DPPH: 80.3%, FRAP: 60.5% and ABTS: 78.9), and potent enzyme inhibitory effects were observed. The SWE and Withaferin A showed significant reduction in cell viability of cervical cancer (HeLa) cells, with IC50 values 10 mg/ml and 8.5 µM/ml, respectively but no cytotoxic effect for normal cells (MDCK). Thus, SWE can provide effective extraction for ashwagandha withanosides and withanolides compared MAE, SE and MC to conventional methods, which could be used for extraction of pharmacologically active fractions with therapeutic applications.


Assuntos
Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Inibidores Enzimáticos/farmacologia , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Vitanolídeos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Cães , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Células HeLa , Humanos , Células Madin Darby de Rim Canino , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Raízes de Plantas/química , Saponinas/química , Saponinas/isolamento & purificação , Extração em Fase Sólida/métodos , Água/química , Withania/química , Vitanolídeos/química , Vitanolídeos/isolamento & purificação
13.
Food Chem Toxicol ; 132: 110655, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31271762

RESUMO

Methyl protodioscin (MPD) is a steroid saponin which has been well known for its pharmacological properties. Herein, we evaluated the anti-cancer activity of MPD for proliferation inhibition and apoptosis induction in Hela cells. MPD was purified from the rhizoma of Polygonatum sibiricum primarily and identified by HPLC, UPLC-TOF-MS/MS and NMR analysis, respectively. Results showed that MPD repressed cell proliferation at IC50 of 18.49 µM, altered cell morphology, arrested the cell cycle in G2/M phase, facilitated the generation of intracellular ROS and led to cell apoptosis in a concentration-dependent manner. Furthermore, MPD treatment promoted death receptor pathway and mitochondrial pathway efficiently. The inhibition of Caspase-8 and Caspase-9 proteins in these pathways abolished the apoptosis significantly, further demonstrated the mechanism of MPD-induced apoptosis. These findings offer novel information that MPD may be considered as a possible natural anti-cancerous agent in the form of functional foods or medicinal products.


Assuntos
Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Diosgenina/análogos & derivados , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Polygonatum/química , Saponinas/farmacologia , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Diosgenina/isolamento & purificação , Diosgenina/farmacologia , Células HEK293 , Células HeLa , Humanos , Espécies Reativas de Oxigênio/metabolismo , Saponinas/isolamento & purificação
14.
Bol. latinoam. Caribe plantas med. aromát ; 18(4): 347-358, jul. 2019. ilus
Artigo em Inglês | LILACS | ID: biblio-1008172

RESUMO

Manilkara zapota (Sapotaceae), commonly known as Sapodilla, is widely known for its delicious fruit. Various parts of this plant are also used in folk medicine to treat a number of conditions including fever, pain, diarrhoea, dysentery, haemorrhage and ulcers. Scientific studies have demonstrated analgesic, anti-inflammatory, antioxidant, cytotoxic, antimicrobial, antidiarrheal, anti-hypercholesteremic, antihyperglycemic and hepatoprotective activities in several parts of the plant. Phytochemical studies have revealed the presence of phenolic compounds including protocatechuic acid quercitrin, myricitrin, catechin, gallic acid, vanillic acid, caffeic acid, syringic acid, coumaric acid, ferulic acid, etc. as main constituents of the plant. Several fatty acids, carotenoids, triterpenes, sterols, hydrocarbons and phenylethanoid compounds have also been isolated from M. zapota. The present review is a comprehensive description focused on pharmacological activities and phytochemical constituents of M. zapota.


Manilkara zapota (Sapotaceae), comúnmente conocida como Sapodilla, es ampliamente conocida por su delicioso fruto. Variadas partes de esta planta se usan en medicina popular para tratar una serie de afecciones, como fiebre, dolor, diarrea, disentería, hemorragia y úlceras. Estudios científicos han demostrado actividad analgésica, antiinflamatoria, antioxidante, citotóxica, antimicrobiana, antidiarreica, antihipercolesterolémica, antihiperglucémica y hepatoprotectora en diferentes partes de la planta. Los estudios fitoquímicos han revelado la presencia de compuestos fenólicos que incluyen ácido protocatechúico, quercitrina, miricitrina, catequina, ácido galico, ácido vanílico, ácido cafeico, ácido sirínico, ácido cumárico, ácido fúnico y ácido ferúlico como componentes principales de la planta. Varios ácidos grasos, carotenoides, triterpenos, esteroles, hidrocarburos y compuestos feniletanoides también han sido aislados de M. zapota. La presente revisión es una descripción exhaustiva centrada en las actividades farmacológicas y los constituyentes fitoquímicos de M. zapota.


Assuntos
Extratos Vegetais/farmacologia , Manilkara/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , Esteróis/isolamento & purificação , Esteróis/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Carotenoides/isolamento & purificação , Carotenoides/farmacologia , Sapotaceae/química , Compostos Fenólicos/análise , Medicina Tradicional
15.
J Agric Food Chem ; 67(27): 7706-7715, 2019 Jul 10.
Artigo em Inglês | MEDLINE | ID: mdl-31246022

RESUMO

While searching for new antifungal compounds, we revealed that a methanol extract of plant species Maesa japonica has a potent antifungal activity in vivo against rice blast fungus Magnaporthe oryzae. To identify the antifungal substances, the methanol extract of M. japonica was extracted by organic solvents, and consequently, six active compounds were isolated from the n-butanol layer. The isolated compounds were five new acylated triterpenoid saponins including maejaposide I (1), maejaposides C-1, C-2, and C-3 (2-4), and maejaposide A-1 (5), along with a known one, maejaposide A (6). These chemical structures were determined by NMR and a comparison of their NMR and MS data with those reported in the literature. Based on the in vitro antifungal bioassay, the five compounds (2-6) exhibited strong antifungal activity against M. oryzae with MIC values ranging from 4 to 32 µg/mL, except for maejaposide I (1) (MIC > 250 µg/mL). When the compounds were evaluated at concentrations of 125, 250, and 500 µg/mL for an in vivo antifungal activity against rice blast, compounds 2-6 strongly reduced the development of blast by at least 85% to 98% compared to the untreated control. However, compound 1 did not show any in vivo antifungal activity up to a concentration of 500 µg/mL. Taken together, our results suggest that the methanol extract of M. japonica and the new acylated triterpenoid saponins can be used as a source for the development of natural fungicides.


Assuntos
Fungicidas Industriais , Maesa/química , Magnaporthe/efeitos dos fármacos , Oryza/microbiologia , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Acilação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Saponinas/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
16.
Free Radic Res ; 53(6): 655-668, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31185752

RESUMO

Oxidative stress accompanying excessive accumulation of reactive oxygen species (ROS) and mitochondrial dysfunction leads to the occurrence of neurodegenerative diseases. Our previous study showed that Eclalbasaponin I (EcI), a triterpene saponin isolated from Aralia elata (Miq.) Seem. (A. elata), repressed oxidative stress in human neuroblastoma SH-SY5Y cells. However, the detailed mechanism remains unclear. In this study, pretreatment with EcI in SH-SY5Y cells significantly activated the p38-mitogenactivated protein kinase (p38), the extracellular regulated protein kinase (ERK), whereas it did not affect the c-jun NH2 terminal kinases (JNK). In accordance with the initial findings, EcI-induced neuroprotective effect was attenuated by SB203580 (SB, a p38 inhibitor) or FR180204 (FR, an ERK inhibitor), being further confirmed by specific small interfering RNA (siRNA). Inhibition of either p38 or ERK up-regulated the apoptosis induction in EcI- and H2O2-cotreated cells. Furthermore, p38 or ERK suppression enhanced intracellular and mitochondrial ROS generation, decreased the activities of endogenous antioxidant defences as well as the mitochondrial membrane potential (MMP), resulting in dysfunction of mitochondria. In addition, EcI-induced autophagy and mitophagy were obviously down-regulated when p38 or ERK activation was blocked. Cumulatively, these findings supported that EcI-caused mitophagy contributed to the neuroprotective effect through p38 or ERK activation. Mitophagy induction might be an effective therapeutic intervention in neurodegenerative diseases.


Assuntos
Apoptose/efeitos dos fármacos , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Saponinas/farmacologia , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismo , Aralia/química , Sobrevivência Celular/efeitos dos fármacos , Ativação Enzimática/efeitos dos fármacos , Humanos , Peróxido de Hidrogênio/antagonistas & inibidores , Peróxido de Hidrogênio/farmacologia , Imidazóis/farmacologia , Modelos Moleculares , Conformação Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Inibidores de Proteínas Quinases/farmacologia , Pirazóis/farmacologia , Piridazinas/farmacologia , Piridinas/farmacologia , Saponinas/química , Saponinas/isolamento & purificação , Células Tumorais Cultivadas
17.
J Nat Med ; 73(4): 814-819, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31054009

RESUMO

Two new steroidal saponins, scrobiculosides A and B, were isolated from the deep-sea sponge Pachastrella scrobiculosa, collected at a depth of 200 m off Miura Peninsula, Japan. The aglycones of scrobiculosides A and B feature a vinylic cyclopropane and a ∆24,25 exomethylene on the side chains, respectively. Both saponins have a common sugar moiety composed of ß-D-galactopyranosyl-(1 → 2)-6-acetyl-ß-D-glucopyranoside, with the exception of an acetyl group on C6″ in scrobiculoside A. Scrobiculoside A exhibited cytotoxicity against HL-60 and P388 cells, with IC50 values of 52 and 61 µM, respectively.


Assuntos
Poríferos/metabolismo , Saponinas/isolamento & purificação , Saponinas/farmacologia , Esteroides/farmacologia , Animais , Linhagem Celular Tumoral , Células HL-60 , Humanos , Japão , Estrutura Molecular , Saponinas/química , Esteroides/química , Esteroides/isolamento & purificação
18.
Phytochem Anal ; 30(6): 644-652, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31059191

RESUMO

INTRODUCTION: Quillaja brasiliensis (St. A. -Hil. & Tul) Mart (Quillajaceae) is a species native to South America, which is rich in saponins. Saponins are used in different industries, so there is a constant demand for this type of compound. Based on the wide range of applications for the saponins found in this species, notably as immunoadjuvants, we conducted a comprehensive study of this tree and its saponins. OBJECTIVE: The purpose of this work is to complete the characterisation of the immunoadjuvant saponin fraction from Q. brasiliensis leaves and further study the saponin fraction obtained from Q. brasiliensis bark. METHODOLOGY: Saponin fractions were studied using mass spectrometry in combination with classical methods of monosaccharide and methylation analysis. We performed direct infusion and liquid chromatography/electrospray ionisation ion trap multiple-stage mass spectrometry (DI-ESI-IT-MSn and LC-ESI-IT-MS2 ). RESULTS: Seventy-five saponins, 21 from leaves and 54 from bark, were tentatively identified according to their molecular mass, fragmentation pattern and chromatographic behaviour. This work represents the first investigation of saponins from the bark of Q. brasiliensis and some of them presented new structural motifs not previously reported in the genus Quillaja. CONCLUSION: The efficiency and selectivity of the data dependent LC-MS2 method allowed the rapid profiling of saponins from Q. brasiliensis. The results of the monosaccharide and methylation analysis performed in saponins from Q. brasiliensis fractions and Q. saponaria Molina (Quillajaceae) fraction gives further support to the structures proposed according to the mass spectral data, validating the strategy used in the present work.


Assuntos
Adjuvantes Imunológicos/química , Cromatografia Líquida/métodos , Casca de Planta/química , Folhas de Planta/química , Quillaja/química , Saponinas/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Configuração de Carboidratos , Metilação , Saponinas/isolamento & purificação
19.
Food Chem ; 294: 276-284, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31126464

RESUMO

A two-level Plackett-Burman design with 8 variables was used to evaluate ultrasonic treatment variables influencing the total phenolic content (TPC) extracted from asparagus roots. Steepest ascent method was conducted to identify the significance of parameters such as extraction temperature, stirring speed, intermission time, extraction time, ultrasonic frequency, and ultrasonic power. Ethanol and methanol aqueous solutions were used as extraction solvents and solvent's concentration, extraction time, ultrasonic power and solid: liquid ratio were optimized in this study. A predicted value of TPC (71.1 mg/g) was obtained under the optimum conditions of extraction time 120 min, ultrasonic power 550 W, ethanol concentration of 20% and a solid: liquid ratio of 1:100. Central composite design was employed to further analyse the common interactions between the extraction variables and to further determine the optimal values that would generate the maximum TPC, total flavonoids content, total saponins content, caffeic acid and in vitro antioxidant activities. The optimal variables for ethanol extraction (80 min, 50% of ethanol, 360 W and 1:40) generated higher than methanol (410 W for 114.9 min using 73.7% methanol at 1:24).


Assuntos
Antioxidantes/química , Asparagus (Planta)/química , Compostos Fitoquímicos/química , Asparagus (Planta)/metabolismo , Ácidos Cafeicos/química , Ácidos Cafeicos/isolamento & purificação , China , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Nova Zelândia , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Saponinas/química , Saponinas/isolamento & purificação , Sonicação , Espectrofotometria Ultravioleta
20.
Phytochemistry ; 164: 67-77, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31100654

RESUMO

For more than four centuries, the intake of Narthecium ossifragum has been associated with poisoning in domesticated animals. Saponins occurring in flowering tops of the plant are considered to cause kidney damage in calves. At present, there are more than 30 papers on the saponins of N. ossifragum in the literature, although the structures of these compounds have hitherto not been determined. Here, we identify the saponins of N. ossifragum as sarsasapogenin, sarsasapogenin-3-O-ß-galactopyranoside, sarsasapogenin-3-O-(2'-O-ß-glucopyranosyl-ß-galactopyranoside) and sarsasapogenin-3-O-(2'-O-ß-glucopyranosyl-3'-O-α-arabinopyranosyl-ß-galactopyranoside). Moreover, six aromatic natural products were isolated and characterized from the methanolic extract from flowers of N. ossifragum. Five of these aromatic compounds, chrysoeriol 6-C-ß-arabinofuranoside-8-C-ß-glucopyranoside, chrysoeriol 6-C-ß-arabinopyranosyl-8-C-ß-glucopyranoside, chrysoeriol 6-C-ß-xylopyranosyl-8-C-ß-galactopyranoside, chrysoeriol 6-C-ß-galactopyranosyl-8-C-ß-glucopyranoside and chrysoeriol 6-C-ß-glucopyranosyl-8-C-ß-galactopyranoside are undescribed. All compounds were tested for cytotoxicity in mammalian cell lines derived from the heart, kidney, and haematological tissues. The saponins exhibited cytotoxicity in the micromolar range, with proportionally increasing cytotoxicity with increasing number of glycosyl substituents. The most potent compound was the main saponin sarsasapogenin-3-O-(2'-O-ß-glucopyranosyl-3'-O-α-arabinopyranosyl-ß-galactopyranoside), which produced cell death at concentrations below 3-4 µM in all three cell lines tested. This indicates that the saponins are the toxicants mainly responsible for kidney damage observed in cattle after ingestion of N. ossifragum. Our findings also pave the way for analysis of individual compounds isolated during the biopsies of intoxicated animals.


Assuntos
Produtos Biológicos/farmacologia , Topos Floridos/química , Magnoliopsida/química , Saponinas/farmacologia , Animais , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Conformação Molecular , Ratos , Saponinas/química , Saponinas/isolamento & purificação , Relação Estrutura-Atividade
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA