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1.
Georgian Med News ; (294): 171-181, 2019 Sep.
Artigo em Russo | MEDLINE | ID: mdl-31687972

RESUMO

The aim of the study was a preliminary study of plant samples collected by targeted expeditions of the department of pharmacobotany (Department of Phytochemistry) of the IG Kutateladze Institute of Pharmacochemistry for the period 2016-2017. In total, 341 objects from (106 various) plants belonging to 36 families and 93 genus were analyzed. The objects were obtained polar and non-polar fractions; flavonoids and triterpenoids were found in them qualitatively. To characterize used P /CH and TLC analysis in various solvent systems. Flavonoids were isolated from Geranium ibericum and Polygonum carneum, which were identified as quercetin-3-0-ß-D-galactopyranoside-hyperin (G. ibericum), 3 5, 7 ', 3'.4' pentahydroxy-flavone - quercetin (G. ibericum, P. сarneum) and quercetin-3-0-rutinozide - rutin (P. сarneum). G. ibericum and P.carneum flora of Georgia are found and studied for the first time. Representatives of the family Asteraceae, Fabaceae, Helleboraceae, Polygonaceae, Scrophula riaceae deserve a particular interest in the content of triterpenoids.


Assuntos
Flavonoides/isolamento & purificação , Extratos Vegetais , Plantas Medicinais , Triterpenos/isolamento & purificação , Etnobotânica , República da Geórgia , Humanos , Polygonaceae , Quercetina
2.
J Med Microbiol ; 68(10): 1438-1444, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31385784

RESUMO

Introduction. Combretum leprosum (Combretaceae) is commonly found in the Northeast Region of Brazil and is known for several bioactivities, including antimicrobial ones. Because of increasing bacterial antibiotic resistance, natural products from several plants have been studied as putative adjuvants to antibiotic activity, including products from C. leprosum. Aims. This study was carried out to investigate the structural properties, bactericidal activity and antibiotic modifying action of the lupane triterpene 3ß,6ß,16ß-trihydroxylup-20(29)-ene (CLF1) isolated from C. leprosum Mart. leaves.Methods. The CLF1 was evaluated by the Fourier transform infrared spectroscopy method and the antibacterial activity of this compound was assayed alone and in association with antibiotics by microdilution assay.Results. Spectroscopic studies confirmed the molecular structure of the CLF1 and permitted assignment of the main infrared bands of this natural product. Microbiological assays showed that this lupane triterpene possesses antibacterial action with clinical relevance against Staphylococcus aureus. The CLF1 triterpene increased antimicrobial activity against the multidrug-resistant Escherichia coli 06 strain when associated with the antibiotics gentamicin and amikacin. Synergistic effects were observed against the S. aureus 10 strain in the presence of the CLF1 triterpene with the antibiotic gentamicin.Conclusion. In conclusion, the CLF1 compound may be useful in the development of antibacterial drugs against the aforementioned bacteria.


Assuntos
Antibacterianos/farmacologia , Combretum/química , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Brasil , Escherichia coli/efeitos dos fármacos , Escherichia coli/crescimento & desenvolvimento , Gentamicinas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/crescimento & desenvolvimento , Triterpenos/química , Triterpenos/isolamento & purificação
3.
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
4.
Fitoterapia ; 137: 104262, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31284018

RESUMO

Eight undescribed 9,19-cycloartane type triterpenoid glycosides (cimdalglnoside A-H) and ten known analogues were obtained from the phytochemical research on the roots of Actaea dahurica (syn. Cimicifuga dahurica). All compounds were characterised by spectroscopic experiments, and chemical method. All the compounds isolated were assayed for cytotoxicity to five human cancer cell lines. Cimdalglnoside G showed promising cytotoxicities against Hela, and MCF-7 cell lines with IC50 values at 7.7 and 12.2 µM.


Assuntos
Actaea/química , Glicosídeos/farmacologia , Raízes de Plantas/química , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , China , Glicosídeos/isolamento & purificação , Células HeLa , Humanos , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Triterpenos/isolamento & purificação
5.
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
6.
Zhongguo Zhong Yao Za Zhi ; 44(9): 1829-1835, 2019 May.
Artigo em Chinês | MEDLINE | ID: mdl-31342709

RESUMO

The chemical constituents from methanol extract of Dichroa hirsuta were separated by silica gel and Sephadex LH-20 column chromatography,high pressure preparative liquid chromatography( HPLC) and recrystallization. Their structures were elucidated by NMR and MS. Nine compounds were obtained and their structures were identified as 3ß,21α-O-diacetyl-lup-9( 11)-en-7ß-ol( 1),( Z)-methyl p-hydroxycinnamate( 2),cis-p-coumaric acid ethyl ester( 3),( E)-methyl p-hydroxycinnamate( 4),trans-p-coumaric acid ethyl ester( 5),4( 3 H)-quinazolinone( 6),7-hydroxycoumarin( 7),hydrangenol( 8) and thunberginol C( 9). Compound 1 is a new lupane-type triterpenoid,and compounds 1-5,8-9 were firstly isolated from this plant. Dual reporter assay results showed that compounds 2-5 could activate the Nrf2-ARE signaling pathway.


Assuntos
Medicamentos de Ervas Chinesas , Hydrangea/química , Triterpenos/farmacologia , Cromatografia Líquida de Alta Pressão , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Triterpenos/isolamento & purificação
7.
Eur J Med Chem ; 177: 302-315, 2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31158746

RESUMO

Betulin-1,4-quinone hybrids were obtain by connecting two active structures with a linker. This strategy allows for obtaining compounds showing a high biological activity and better bioavailability. In this research, synthesis, anticancer activity and molecular docking study of betulin-1,4-quinone hybrids are presented. Newly synthesized compounds were characterized by 1H, 13C NMR, IR and HR-MS. Hybrids were tested in vitro against a panel of human cell lines including glioblastoma, melanoma, breast and lung cancer. They showed a high cytotoxic activity depending on the type of 1,4-quinone moiety and the applied tumor cell lines. It was found that cytotoxic activities of the studied hybrids were increasing against the cell line with higher NQO1 protein level, like melanoma (C-32), breast (MCF-7) and lung (A-549) cancer. Selected hybrids were tested on the transcriptional activity of the gene encoding a proliferation marker (H3 histone), a cell cycle regulators (p53 and p21) and an apoptosis pathway (BCL-2 and BAX). The obtained results suggested that the tested compounds caused a mitochondrial apoptosis pathway in A549 and MCF-7 cell lines. The molecular docking was used to examine the probable interaction between the hybrids and human NAD[P]H-quinone oxidoreductase (NQO1) protein. The computational studies showed that the type of the 1,4-quinone moiety affected the location of the compound in the active site of the enzyme. Moreover, it was shown that an interaction of 1,4-quinone fragment with the hydrophobic matrix of the active site near Tyr128, Phe178, Trp105 and FAD cofactor could explain the observed increase of TP53 gene expression.


Assuntos
Antineoplásicos/farmacologia , NAD(P)H Desidrogenase (Quinona)/metabolismo , Quinonas/farmacologia , Triterpenos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Antineoplásicos/metabolismo , Apoptose/efeitos dos fármacos , Betula/química , Domínio Catalítico , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Inibidor de Quinase Dependente de Ciclina p21/genética , Ensaios de Seleção de Medicamentos Antitumorais , Regulação Neoplásica da Expressão Gênica/genética , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , NAD(P)H Desidrogenase (Quinona)/química , Ligação Proteica , Quinonas/síntese química , Quinonas/química , Quinonas/metabolismo , Relação Estrutura-Atividade , Triterpenos/síntese química , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/metabolismo , Proteína Supressora de Tumor p53/genética
8.
Fitoterapia ; 137: 104242, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31202889

RESUMO

Seven oleanane-type glycosides were extracted and isolated by various chromatographic methods from the roots of Weigela x "Bristol Ruby" (1-7), six previously undescribed (1-6) and a known one (7). Their structures were assigned by spectroscopic analysis mainly 2D NMR and mass spectrometry (ESIMS). Selected triterpenoid glycosides (1-3, 6, 7) displayed a good cytotoxic activity against a mouse colon cancer cell line CT26.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Caprifoliaceae/química , Glicosídeos/farmacologia , Ácido Oleanólico/análogos & derivados , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Glicosídeos/isolamento & purificação , Camundongos , Estrutura Molecular , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
9.
Molecules ; 24(11)2019 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-31181656

RESUMO

Pentacyclic triterpenic acids from oleogum resins of Boswellia species are of considerable therapeutic interest. Yet, their pharmaceutical development is hampered by uncertainties regarding botanical identification and the complexity of triterpenic acid mixtures. Here, a highly sensitive, selective, and accurate method for the simultaneous quantification of eight boswellic and lupeolic acids by high-performance liquid chromatography with tandem mass spectrometry detection (HPLC-MS/MS) was developed. The method was applied to the comparative analysis of 41 oleogum resins of the species B. sacra, B. dalzielli, B. papyrifera, B. serrata, B. carterii, B. neglecta, B. rivae, B. frereana, and B. occulta. Multivariate statistical analysis of the data revealed differences in the triterpenic acid composition that could be assigned to distinct Boswellia species and to their geographic growth location. Extracts of the oleogum resins exhibited cytotoxicity against the human, treatment-resistant, metastatic breast cancer cell line MDA-MB-231. Extracts from B. sacra were the most potent ones with an average IC50 of 8.3 ± 0.6 µg/mL. The oleogum resin of the B. sacra was further fractionated to enrich different groups of substances. The cytotoxic efficacy against the cancer cells correlates positively with the contents of pentacyclic triterpenic acids in Boswellia extracts.


Assuntos
Antineoplásicos Fitogênicos/análise , Boswellia/química , Neoplasias da Mama/tratamento farmacológico , Triterpenos Pentacíclicos/análise , Resinas Vegetais/análise , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Feminino , Humanos , Triterpenos Pentacíclicos/farmacologia , Resinas Vegetais/farmacologia , Espectrometria de Massas em Tandem , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
10.
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
11.
Food Chem Toxicol ; 131: 110563, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31199992

RESUMO

Apple pomace (AP) utilised for analysis of triterpenic acids (TTAs) using HPLC-MS/MS. The methanol, ethanol and ethyl acetate extracts showed high phenolic content with significant antioxidant activity compared to chloroform and n-hexane. AP TTAs; ursolic acid, betulinic acid and maslinic acid showed potent antioxidant and enzyme inhibitory effects. The IC50 values were 13.2-30.8 µg/mL (tyrosinase), 19.6-42.5 µg/mL (xanthine oxidase) and 16.6-38.6 µg/mL (urease) for AP extracts and 8.4-25.8 µg/mL (tyrosinase), 12.6-30.2 µg/mL (xanthine oxidase) and 10.1-28.6 µg/mL (urease) for TTAs, compared to the positive controls; kojic acid (10.4 ±â€¯0.06 µg/mL), allopurinol (9.6 ±â€¯0.04 µg/mL) and thiourea (8.9 ±â€¯0.02 µg/mL) towards respective enzymes. UA showed a competitive type of inhibition for tyrosinase, while BA showed a noncompetitive type of inhibition towards xanthine oxidase. In addition, the AP extracts and TTAs exerted significant cytotoxic effects towards the proliferation of cancer cell lines. AP methanol extract (IC50 of 38.5 ±â€¯4.1, 47.1 ±â€¯3.5, 70.6 ±â€¯2.3, and 50.5 ±â€¯3.9 µg/mL) and ursolic acid (IC50 of 6.5 ±â€¯0.7, 15.5 ±â€¯1.4, 20.8 ±â€¯1.3, and 5.6 ±â€¯0.8 µg/mL) showed prominent anticancer activity on Hela, Skov-3, Caski, and NCL cancer cell lines, respectively. Thus, this study shows that the AP & TTAs could be utilized for functional food development and as a potent antioxidant, anticancer, skin whitening, and anti-urolithic agents.


Assuntos
Antineoplásicos/farmacologia , Inibidores Enzimáticos/farmacologia , Depuradores de Radicais Livres/farmacologia , Frutas/química , Malus/química , Triterpenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Cães , Ensaios Enzimáticos , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Depuradores de Radicais Livres/química , Depuradores de Radicais Livres/isolamento & purificação , Humanos , Células Madin Darby de Rim Canino , Monofenol Mono-Oxigenase/antagonistas & inibidores , Extratos Vegetais/análise , Extratos Vegetais/química , Extração em Fase Sólida , Triterpenos/química , Triterpenos/isolamento & purificação , Urease/antagonistas & inibidores , Xantina Oxidase/antagonistas & inibidores
12.
Chem Pharm Bull (Tokyo) ; 67(6): 604-608, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31155567

RESUMO

Two new triterpene glycosides (1 and 2), together with nine known triterpene glycosides (3-11), were isolated from the seeds of Dolichos lablab (Leguminosae). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The isolated compounds did not show cytotoxicity against HL-60 human leukemia cells and HepG2 human hepatoma cells at sample concentrations of 20 µM.


Assuntos
Dolichos/química , Glicosídeos/química , Triterpenos/química , Sobrevivência Celular/efeitos dos fármacos , Dolichos/metabolismo , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células HL-60 , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Sementes/química , Sementes/metabolismo , Extração em Fase Sólida , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
13.
J Agric Food Chem ; 67(26): 7348-7364, 2019 Jul 03.
Artigo em Inglês | MEDLINE | ID: mdl-31180673

RESUMO

A chemical study on the peels of the cultivated edible mushroom Wolfiporia cocos led to the isolation and identification of 47 lanostane triterpenoids including 16 new compounds (1-16). The structures of the new compounds were determined by analysis of the NMR, MS, and electronic circular dichroism (ECD) data. Compounds 1 and 2 represent new members of the family of 4,5-secolanostane triterpenes. Compound 3 is a new aromatic lanostane triterpene with an unusual methyl rearrangement from C-10 to C-6. The absolute configurations of 1 and 8 were assigned by ECD spectra calculation. All compounds were evaluated for cytotoxicity (K562, SW480, and HepG2) and glucose-uptake-stimulating effects. Compounds 23, 25, 29, and 31 showed weak inhibition on the K562 cells with IC50 in the range of 25.7 to 68.2 µM, respectively. Compounds 21, 28, and 30 increased the glucose uptake in 3T3-L1 cells by 25%, 14%, and 50% at 5 µM, respectively. In addition, compounds 14, 23, 29, 35, and 43 showed insulin-sensitizing activity by increasing the insulin-stimulated glucose uptake at 2.5 µM in 3T3-L1 adipocytes. A preliminary structure-activity relationship analysis indicates that the 6/6/6/5 ring skeleton and the double bond between C-8 and C-9 are beneficial for the glucose-uptake-stimulating and insulin-sensitizing activities. Furthermore, the alkaline-insoluble fraction mainly containing compounds 22, 24, 28, and 31 were confirmed to have hypoglycemic and hypolipidemic activity on high-fat-diet-induced obese mice. This work confirms the potential of the peels' extracts of W. cocos as a functional food or dietary supplements.


Assuntos
Glucose/metabolismo , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Wolfiporia/química , Células 3T3-L1 , Adipócitos/efeitos dos fármacos , Adipócitos/metabolismo , Animais , Transporte Biológico/efeitos dos fármacos , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Insulina/metabolismo , Camundongos , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação
14.
Chem Pharm Bull (Tokyo) ; 67(6): 534-539, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31155558

RESUMO

One triterpene and five triterpene glycosides, including four new compounds, have been identified in the underground parts of Glycyrrhiza bucharica, which was shown to be closely related to Glycyrrhizin-producing Glycyrrhiza species, G. uralensis, G. glabra and G. inflata, based on their chloroplast rbcL sequences. Two known compounds were identified squasapogenol and macedonoside C. The structures of four new compounds, bucharosides A, B, C, and D, were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl squasapogenol, 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-macedonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-squasapogenol, and 22-O-α-L-rhamnopyranosyl squasapogenol, respectively. Contents of these triterpene glycosides were less than 0.5% of dry weight, and no main saponin, like glycyrrhizin or macedonoside C found in other Glycyrrhiza species, was found in the underground parts of G. bucharica.


Assuntos
Glycyrrhiza/química , Extratos Vegetais/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glycyrrhiza/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Tadjiquistão , Terpenos/química , Terpenos/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação
15.
Mar Drugs ; 17(6)2019 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-31146323

RESUMO

Pharmaceutical agents for halting the progression of Parkinson's disease (PD) are lacking. The current available medications only relieve clinical symptoms and may cause severe side effects. Therefore, there is an urgent need for novel drug candidates for PD. In this study, we demonstrated the neuroprotective activity of stellettin B (SB), a compound isolated from marine sponges. We showed that SB could significantly protect SH-SY5Y cells against 6-OHDA-induced cellular damage by inhibiting cell apoptosis and oxidative stress through PI3K/Akt, MAPK, caspase cascade modulation and Nrf2/HO-1 cascade modulation, respectively. In addition, an in vivo study showed that SB reversed 6-OHDA-induced a locomotor deficit in a zebrafish model of PD. The potential for developing SB as a candidate drug for PD treatment is discussed.


Assuntos
Apoptose/efeitos dos fármacos , Heme Oxigenase-1/metabolismo , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Poríferos/química , Triterpenos/farmacologia , Animais , Organismos Aquáticos/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Modelos Animais de Doenças , Humanos , Locomoção/efeitos dos fármacos , Fármacos Neuroprotetores/farmacologia , Oxidopamina/toxicidade , Doença de Parkinson/tratamento farmacológico , Triterpenos/química , Triterpenos/isolamento & purificação , Peixe-Zebra
16.
Fitoterapia ; 137: 104193, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31175949

RESUMO

Three new iridal-type triterpenoids (1-3) featuring a rearranged homofarnesylside chain were isolated from the rhizomes of Iris tectorum. Compounds 2 and 3 were found to be a pair of epimers. Their structures were elucidated on the basis of comprehensive spectroscopic analysis. A possible biosynthetic pathway for them was postulated. Moreover, the mixture of compounds 2 and 3 exhibited moderate neuroprotective activity against serum deprivation-induced PC12 cell death.


Assuntos
Iris (Planta)/química , Fármacos Neuroprotetores/farmacologia , Triterpenos/farmacologia , Animais , China , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Ratos , Rizoma/química , Triterpenos/isolamento & purificação
17.
Braz J Med Biol Res ; 52(5): e7798, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31116311

RESUMO

Himatanthus drasticus (Mart.) Plumel belongs to the Apocynaceae family and the latex from its trunk bark (Hd) is known as "janaguba milk". This latex is widely used in Northeast Brazil, mainly in the Cariri region, for its gastroprotective, anti-inflammatory, and antitumor properties. The objective of this study was to investigate a triterpene-rich fraction (FJNB) from H. drasticus latex on acute models of nociception and inflammation and to clarify its mechanisms of action. Wistar rats or Swiss mice were subjected to the carrageenan-induced paw edema test or the formalin test, respectively, after the acute oral treatment with FJNB. The inflamed paws from the carrageenan-induced paw edema and formalin tests were processed for histological and immunohistochemical assays, respectively. The results were analyzed by ANOVA and considered significant at P<0.05. FJNB (10 mg/kg) decreased the paw edema by 25% at the 3rd h after the carrageenan injection. Indomethacin, used as reference, inhibited the paw edema by 59% at the same time-point. In the formalin test, FJNB inhibited the 1st phase by 27, 49, and 52% and the 2nd phase by 37, 50, and 67%, at the doses of 1, 5, and 10 mg/kg, respectively. In addition, FJNB significantly inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and the inflammatory cytokine tumor necrosis factor (TNF)-alpha. The histone deacetylase (HDAC) expression and the transcription factor nuclear factor kappa (NF-kB) were also inhibited at the same doses. In conclusion, the FJNB inhibitory actions on iNOS, COX-2, TNF-α, HDAC, and NF-kB could be involved with the drug anti-inflammatory activity.


Assuntos
Analgésicos/uso terapêutico , Anti-Inflamatórios/uso terapêutico , Apocynaceae/química , Edema/tratamento farmacológico , Inflamação/tratamento farmacológico , Triterpenos/uso terapêutico , Animais , Biomarcadores/sangue , Modelos Animais de Doenças , Imuno-Histoquímica , Masculino , Camundongos , Ratos , Ratos Wistar , Triterpenos/isolamento & purificação
18.
Am J Chin Med ; 47(4): 769-785, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31091976

RESUMO

Tripterygium wilfordii Hook F. (TWHF), a traditional Chinese medicine, has been widely used to treat autoimmune and inflammatory diseases including rheumatoid arthritis, systemic lupus erythematosus and dermatomyositis in China. Recently, studies have demonstrated that the bioactive components of TWHF have effective therapeutic potential for neurodegenerative diseases including Alzheimer's disease, Parkinson's disease and Multiple Sclerosis. In this paper, we summarize the research progress of triptolide and celastrol (the two major TWHF components) as well as their analogues in the treatment of neurodegenerative diseases. In addition, we review and discuss the molecular mechanisms and structure features of those two bioactive TWHF components, highlighting their therapeutic promise in neurodegenerative diseases.


Assuntos
Diterpenos/uso terapêutico , Doenças Neurodegenerativas/tratamento farmacológico , Fenantrenos/uso terapêutico , Fitoterapia , Tripterygium/química , Triterpenos/uso terapêutico , Doença de Alzheimer/tratamento farmacológico , Animais , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Compostos de Epóxi/química , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/farmacologia , Compostos de Epóxi/uso terapêutico , Humanos , Medicina Tradicional Chinesa , Conformação Molecular , Fármacos Neuroprotetores , Doença de Parkinson/tratamento farmacológico , Fenantrenos/química , Fenantrenos/isolamento & purificação , Fenantrenos/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
19.
Molecules ; 24(10)2019 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-31091665

RESUMO

Cirsium setosum (C. setosum) has a potential antihyperglycemic effect, but it is unclear what bioactive components play a key role. According to the α-glucosidase inhibition activity, three new taraxastane-type triterpenoids of 3ß-hydroxy-30-hydroperoxy-20-taraxastene (1), 3ß-hydroxy-22α-methoxy-20-taraxastene (2), and 30-nor-3ß,22α-dihydroxy-20-taraxastene (3), as well as five known taraxastane triterpenoids of 3ß,22-dihydroxy-20-taraxastene (4), 20-taraxastene-3,22-dione (5), 3ß-acetoxy-20-taraxasten-22-one (6), 3ß-hydroxy-20-taraxasten-22-one (7), and 30-nor-3ß-hydroxy-20-taraxastene (8) were obtained from the petroleum ether-soluble portion of the ethanol extract from C. setosum. All chemical structures of the compounds were elucidated by spectroscopic data analysis and compared with literature data. Compounds 4-8 were identified for the first time from this plant, and compounds 1, 2, 4, and 7 exhibited more potent α-glucosidase inhibitory activity-with IC50 values of 18.34 ± 1.27, 26.98 ± 0.89, 17.49 ± 1.42, and 22.67 ± 0.25 µM, respectively-than acarbose did (positive control, IC50 42.52 ± 0.32 µM).


Assuntos
Cirsium/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Triterpenos/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Concentração Inibidora 50 , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação
20.
Fitoterapia ; 136: 104178, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31121254

RESUMO

One hitherto unknown 24-nor-13,27-cycloursane-type triterpenoid, lucumic acid A (1), one new 24-nor-ursane triterpenoid, lucumic acid B (2), along with six known triterpenoids were isolated from the ethanol extract of the leaves of Lucuma nervosa. Their structures were established on the basis of spectroscopic data interpretation. Lucumic acid A (1) is the first example of a 24-nor-triterpenoid with a 13,27-cyclopropane ring.


Assuntos
Ácido Oleanólico/análogos & derivados , Folhas de Planta/química , Pouteria/química , Triterpenos/isolamento & purificação , China , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/farmacologia , Estrutura Molecular , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Triterpenos/farmacologia
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