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1.
Fitoterapia ; 175: 105881, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38438054

RESUMO

Two previously undescribed cholestanol saponins, parpetiosides F - G (1-2), and six known analogs (3-8) were isolated from the rhizomes of Paris fargesii var. petiolata. Their structures were elucidated by extensive spectroscopic data analysis and chemical methods. Compound 1 was a rare 6/6/6/5/5 fused-rings cholestanol saponin with disaccharide moiety linked at C-26 of aglycone which was hardly seen in genus Paris. All of these compounds were discovered in this plant for the first time. In addition, the cytotoxicities of saponins (1-8) against three human cancer cell lines (U87, HepG2 and SGC-7901) were evaluated by CCK-8 method, and saponins 5-8 displayed certain cytotoxicities. The strong interactions between saponins 5-8 and SCUBE3, an oncogene for glioma cells, were displayed by molecular docking.


Assuntos
Antineoplásicos Fitogênicos , Colestanol , Simulação de Acoplamento Molecular , Rizoma , Saponinas , Rizoma/química , Humanos , Saponinas/isolamento & purificação , Saponinas/farmacologia , Saponinas/química , Estrutura Molecular , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Colestanol/farmacologia , Colestanol/química , Colestanol/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Melanthiaceae/química , China , Liliaceae/química
2.
Chin J Nat Med ; 21(10): 789-800, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37879796

RESUMO

Five new saponins, including three steroid saponins, paristenoids A-C (1-3), and two triterpenoid saponins, paristenoids D-E (4-5), along with four known ones (6-9) were isolated from the rhizomes of Paris polyphylla var. stenophylla. The structures of the isolated compounds were identified mainly by detailed spectroscopic analysis, including extensive 1D and 2D NMR, MS, as well as chemical methods. Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton, and this skeleton has been first found from the genus Paris. The cytotoxicities of the isolated compounds against three human three glioma cell lines (U87MG, U251MG and SHG44) were evaluated, and compound 7 displayed certain inhibitory effect with IC50 values of 15.22 ± 1.73, 18.87 ± 1.81 and 17.64 ± 1.69 µmol·L-1, respectively.


Assuntos
Liliaceae , Saponinas , Triterpenos , Humanos , Rizoma/química , Esteroides/farmacologia , Esteroides/química , Liliaceae/química , Saponinas/química , Triterpenos/farmacologia , Triterpenos/análise
3.
Phytochemistry ; 207: 113577, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36587887

RESUMO

Paris polyphylla var. yunnanensis (Franch.) Hand.-Mazz. (Melanthiaceae), an important specie of the genus Paris, has long been in a traditional Chinese medicine (TCM) for a long time. This study aimed to isolate and identify the structures of bioactive saponins from the rhizomes of P. polyphylla var. yunnanensis and evaluate their cytotoxicity against BxPC-3, HepG2, U373 and SGC-7901 carcinoma cell lines. Seven previously undescribed and seven known saponins were identified, and Paris saponins VII (PSVII) showed significant cytotoxicity against the BxPC-3 cell line with IC50 values of 3.59 µM. Furthermore, flow cytometry, transmission electron microscopy and western-bolt analysis revealed that PSVII inhibited the proliferation of BxPC-3 cells and might be involved in inducing apoptosis and pyroptosis by activating caspase-3, -7 and caspase-1, respectively.


Assuntos
Antineoplásicos , Liliaceae , Melanthiaceae , Saponinas , Rizoma/química , Saponinas/farmacologia , Liliaceae/química , Melanthiaceae/química
4.
Fitoterapia ; 159: 105179, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35337886

RESUMO

Three new triterpenoid saponins, heracleifolianosides A-C (1-3), together with seven known compounds (4-10), were isolated from the whole plants of Clematis heracleifolia. Moreover, three new secondary saponins (1a, 2a and 3a), two known secondary metabolites (5a and 7a) were obtained by alkaline hydrolysis. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. The cytotoxicity of eight native saponins and five prosapogenins against human breast tumor MDA-MB-231 and gastric carcinoma SGC-7901 cell lines were evaluated by MTT method. Remarkably, the prosapogenin monodesmosidic saponin 7a showed significant cytotoxicity against MDA-MB-231 or SGC-7901 cell lines with IC50 values in the range of 6.05-6.32 µmol/L. It is suggested that it might be a feasible way to change the inactive bisdesmosic triterpenoid saponins to active monodesmosic saponins by a simple procedure of alkaline hydrolysis.


Assuntos
Antineoplásicos Fitogênicos , Clematis , Saponinas , Triterpenos , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Clematis/química , Humanos , Estrutura Molecular , Saponinas/química , Saponinas/farmacologia , Triterpenos/química , Triterpenos/farmacologia
5.
Molecules ; 26(21)2021 Oct 21.
Artigo em Inglês | MEDLINE | ID: mdl-34770773

RESUMO

The genus Paris is an excellent source of steroidal saponins that exhibit various bioactivities. Paris mairei is a unique species and has been widely used as folk medicine in Southwest China for a long time. With the help of chemical methods and modern spectra analysis, five new steroidal saponins, pamaiosides A-E (1-5), along with five known steroidal saponins 6-10, were isolated from the rhizomes of Paris mairei. The cytotoxicity of all the new saponins was evaluated against human pancreatic adenocarcinoma PANC-1 and BxPC3 cell lines.


Assuntos
Melanthiaceae/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Rizoma/química , Saponinas/química , Saponinas/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Fracionamento Químico , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Fitosteróis/química , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologia , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Análise Espectral
6.
Biosci Trends ; 14(2): 123-133, 2020 May 21.
Artigo em Inglês | MEDLINE | ID: mdl-32173672

RESUMO

Glioblastoma is one of the most difficult cancers to treat with a 5-year overall survival rate less than 5%. Temozolomide (TMZ) is an effective drug for prolonging the overall survival time of patients, while drug-resistance is an important clinical problem at present. Pennogenin-3-α-L-rhamnopyranosyl-(1→4)-[α-Lrhamno-pyranosyl-(1→2)]- ß-D-glucopyranoside (N45), a steroidal saponin, was isolated from the rhizomes of Paris vietnamensis (Takht.), which is used as a Traditional Chinese Medicine and has been reported to possess preclinical anticancer efficacy in various cancer types. However, the mechanism of the inhibition of N45 on glioblastoma cells and its possible application in the treatment of chemotherapy-resistant glioblastoma cells are still unknown. In this study, we use cellular methodological experiments including cell counting kit-8 (CCK-8) assay, terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) staining assay, flow cytometry assay, transmission electron microscopy (TEM) and Western blot. The results show that N45 significantly suppresses the proliferation of glioblastoma cells and TMZ-resistant glioblastoma cells (U87R) by inducing mitochondrial apoptosis through reactive oxygen species (ROS)/phosphoinositide 3-kinase (PI3K)/Akt signal pathway, and the N-acetyl-L-cysteine (NAC) combined with N45 effectively reduced N45-mediated apoptosis and reversed the inhibition of PI3K/Akt signal pathway. In addition, N45 decreased the drug-resistance by down-regulation of nuclear factor kappa-B p65 (NF-κB p65) to attenuate O6-methylguanine-DNA methyltransferase (MGMT) in TMZ-resistant glioblastoma cells (U87R). Our findings proved that N45 might be a potential therapeutic agent against glioblastoma and TMZ-resistant glioblastoma, promising to be a potential agent to reduce drug resistance.


Assuntos
Protocolos de Quimioterapia Combinada Antineoplásica/farmacologia , Neoplasias Encefálicas/tratamento farmacológico , Glioblastoma/tratamento farmacológico , Melanthiaceae/química , Saponinas/farmacologia , Acetilcisteína/farmacologia , Acetilcisteína/uso terapêutico , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Protocolos de Quimioterapia Combinada Antineoplásica/uso terapêutico , Apoptose/efeitos dos fármacos , Neoplasias Encefálicas/patologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/uso terapêutico , Glioblastoma/patologia , Humanos , Fosfatidilinositol 3-Quinases/metabolismo , Espécies Reativas de Oxigênio/antagonistas & inibidores , Espécies Reativas de Oxigênio/metabolismo , Rizoma/química , Saponinas/uso terapêutico , Transdução de Sinais/efeitos dos fármacos , Temozolomida/farmacologia , Temozolomida/uso terapêutico
7.
Molecules ; 20(1): 293-308, 2014 Dec 24.
Artigo em Inglês | MEDLINE | ID: mdl-25547727

RESUMO

Oxidative stress plays an important role in Parkinson's disease and other neurodegenerative disorders. Lycium barbarum polysaccharides (LBP), the main active ingredients extracted from the fruits of Lycium barbarum L., have been shown to be a potent antioxidant. In the present study, we investigated the protective effects, and the possible mechanism of action of LBP against 6-hydroxydopamine (6-OHDA)-induced apoptosis in PC12 cells. Our data demonstrated that LBP significantly reversed the 6-OHDA-induced decrease in cell viability, prevented 6-OHDA-induced changes in condensed nuclei and decreased the percentage of apoptotic cells in a dose-dependent manner. Furthermore, LBP also slowed the accumulation of reactive oxygen species (ROS) and nitric oxide (NO), decreased the level of protein-bound 3-nitrotyrosine (3-NT) and intracellular free Ca2+, and inhibiting the overexpression of nuclear factor κB (NF-κB), neuronal nitric oxide synthase (nNOS) and inducible nitric oxide synthase (iNOS). These results demonstrate that LBP prevents 6-OHDA-induced apoptosis in PC12 cells, at least in part through the ROS-NO pathway.


Assuntos
Apoptose/efeitos dos fármacos , Medicamentos de Ervas Chinesas/farmacologia , Óxido Nítrico/metabolismo , Oxidopamina/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Animais , Caspase 3/metabolismo , Caspase 9/metabolismo , Óxido Nítrico Sintase Tipo I/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Células PC12 , Ratos
8.
Fitoterapia ; 89: 224-30, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23774664

RESUMO

Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of three new oleanane-type triterpenoid saponins (1-3), together with four known saponins (4-7). Their structures were elucidated on the basis of spectroscopic analysis and chemical derivatization. All the compounds were isolated for the first time from A. taipaiensis. The cytotoxicity of these compounds was evaluated in five human cancer cell lines including A549 (lung carcinoma), HeLa (cervical carcinoma), HepG2 (hepatocellular carcinoma), HL-60 (promyelocytic leukemia), and U87MG (glioblastoma). The monodesmosidic saponin 4 exhibited cytotoxic activity toward all cancer cell lines, with IC50 values ranging from 6.42 to 18.16 µM. In addition, the bisdesmosidic saponins 1 and 7 showed selective cytotoxicity against the U87MG cells.


Assuntos
Anemone/química , Antineoplásicos Fitogênicos/uso terapêutico , Neoplasias/tratamento farmacológico , Ácido Oleanólico/análogos & derivados , Fitoterapia , Extratos Vegetais/uso terapêutico , Saponinas/isolamento & purificação , Saponinas/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Células HL-60 , Células HeLa , Células Hep G2 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Rizoma/química , Saponinas/química
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