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1.
Fitoterapia ; 137: 104281, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31381957

RESUMO

Veratrum californicum is a rich source of steroidal alkaloids, many of which have proven to be antagonists of the Hedgehog (Hh) signaling pathway that becomes aberrant in over twenty types of cancer. These alkaloids first became known in the 1950's due to their teratogenic properties, which resulted in newborn and fetal lambs developing cyclopia as a result of pregnant ewes consuming Veratrum californicum. It was discovered that the alkaloids in V. californicum were concentrated in the root and rhizome of the plant with much lower amounts of the most active alkaloid, cyclopamine, present in the aerial plant, especially in the late growth season. Inspired by the limitations in analytical instrumentation and methods available to researchers at the time of the original investigation, we have used state-of-the-art instrumentation and modern analytical methods to quantitate four steroidal alkaloids based on study parameters including plant part, harvest location, and growth stage. The results of the current inquiry detail differences in alkaloid composition based on the study parameters, provide a detailed assessment for alkaloids that have been characterized previously (cyclopamine, veratramine, muldamine and isorubijervine), and identify at least six alkaloids that have not been previously characterized. This study provides insight into optimal harvest time, plant growth stage, harvest location, and plant part required to isolate, yet to be characterized, alkaloids of interest for exploration as Hh pathway antagonists with desirable medicinal properties.


Assuntos
Alcaloides/química , Esteroides/química , Veratrum/química , Alcaloides/isolamento & purificação , Proteínas Hedgehog/antagonistas & inibidores , Idaho , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Componentes Aéreos da Planta/química , Rizoma/química , Estações do Ano , Esteroides/isolamento & purificação , Alcaloides de Veratrum
2.
Fitoterapia ; 137: 104285, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31386897

RESUMO

Botanical-based natural products are an important resource for medicinal drug discovery and continue to provide diverse pharmacophores with therapeutic potential against cancer and other human diseases. A prototype Traditional Chinese Medicine (TCM) plant extract library has been established at the US National Cancer Institute, which contains both the organic and aqueous extracts of 132 authenticated medicinal plant species that collectively represent the potential therapeutic contents of most commonly used TCM herbal prescriptions. This library is publicly available in 96- and 384- well plates for high throughput screening across a broad array of biological targets, as well as in larger quantities for isolation of active chemical ingredients. Herein, we present the methodology used to generate the library and the preliminary assessment of the anti-proliferative activity of this crude extract library in NCI-60 human cancer cell lines screen. Particularly, we report the chemical profiling and metabolome comparison analysis of four commonly used TCM plants, namely Brucea javanica, Dioscorea nipponica, Cynanchum atratum, and Salvia miltiorrhiza. Bioassay-guided isolation resulted in the identification of the active compounds, and different extraction methods were compared for their abilities to extract cytotoxic compounds and to concentrate biologically active natural products.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/isolamento & purificação , Brucea/química , Linhagem Celular Tumoral , China , Cynanchum/química , Dioscorea/química , Descoberta de Drogas , Humanos , Medicina Tradicional Chinesa , National Cancer Institute (U.S.) , Compostos Fitoquímicos/isolamento & purificação , Salvia miltiorrhiza/química , Estados Unidos
3.
Fitoterapia ; 137: 104287, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31386898

RESUMO

Phytochemical investigation of the fruit of Crataegus pinnatifida led to the isolation of four pairs of dihydrobenzofuran neolignan enantiomers (1a/1b-4a/4b) including six new compounds (1a/1b, 2a/2b, 3a and 4a). The enantioseparations of the racemates were achieved successfully by chiral chromatographic column. Their structures were established by comprehensive spectroscopic analyses and the absolute configurations were determined by quantum mechanical calculation of electronic circular dichroism (ECD) spectra. All compounds were evaluated in vitro for their cytotoxicity using human hepatocellular carcinoma Hep3B and HepG2 cells. Among them, it was found that 2a had a selective cytotoxicity against Hep3B cells with IC50 value of 25.47 µM, while the IC50 value of its enantiomer 2b on Hep3B cells was 59.37 µM. These results implied that the absolute configurations of 2a and 2b possessed remarkable influences on their cytotoxicity. Further flow cytometry analysis indicated that 2a performed more significant effect on cell apoptosis compared with its enantiomer 2b.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Crataegus/química , Frutas/química , Lignanas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , China , Células Hep G2 , Humanos , Lignanas/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Estereoisomerismo
4.
Fitoterapia ; 137: 104254, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31271782

RESUMO

Five new polyphenolic derivatives, sepiumols A-E (1-5), were isolated from the root barks of Periploca sepium. Their structures were elucidated by interpretation of NMR spectroscopic and mass spectrometric data. Compounds 1, 3 and 5 were found to exhibit significant antifungal activity, particularly for 3 with the remarkable activity against Gibberella saubinetii and Alternaria longipes with MIC values of 1.56 and 3.13 µg/mL (ketoconazole: 0.78 µg/mL), respectively. In addition, compounds 1, 3 and 5 also displayed significant antibacterial activity against methicillin-resistant Staphylococcus aureu with MIC values of 12.50-25 µg/mL (ciprofloxacin: 0.78 µg/mL).


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Periploca/química , Polifenóis/farmacologia , Alternaria/efeitos dos fármacos , Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Gibberella/efeitos dos fármacos , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Casca de Planta/química , Raízes de Plantas/química , Polifenóis/isolamento & purificação
5.
Fitoterapia ; 137: 104251, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31271783

RESUMO

The MeOH extract from leaves of Saururus cernuus L. (Saururaceae) displayed in vitro activity against trypomastigote forms of T. cruzi (100% of parasite death at 200 µg/mL), suggesting the presence of bioactive compounds. Thus, the bioactivity-guided fractionation was carried out, leading to the isolation of three related neolignan derivatives, identified as threo-austrobailignan-5 (1), threo-austrobailignan-6 (2), and threo-dihydroguaiaretic acid (3). Anti-T. cruzi activity of compounds 1-3 was performed against cell-derived trypomastigotes and intracellular amastigotes. Additionally, the mammalian cytotoxicity was investigated using NCTC cells. Compound 2 was the most effective against extracellular trypomastigotes with IC50 of 3.7 µM, while compound 3 showed activity in both clinically relevant forms of the parasite, trypomastigotes and amastigotes, with IC50 values of 7.0 and 16.2 µM, respectively. However, the structurally related compound 1 was inactive. Based on these results, compounds 2 and 3 were selected to evaluate the mechanism of cellular death. Compound 2 induced alteration in the plasma membrane permeability and consequently in the ROS levels after 120 min of incubation. By using flow cytometry and fluorescence microscopy, compound 3 showed alterations in the mitochondrial membrane potential (ΔΨm) of trypomastigotes. Considering the promising chemical and biological properties of neolignans 2 and 3, these compounds could be used as starting points to develop new lead compounds for Chagas disease.


Assuntos
Lignanas/farmacologia , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Saururaceae/química , Tripanossomicidas/farmacologia , Trypanosoma cruzi/efeitos dos fármacos , Animais , Brasil , Células Cultivadas , Guaiacol/análogos & derivados , Lignanas/isolamento & purificação , Macrófagos Peritoneais/parasitologia , Camundongos Endogâmicos BALB C , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Espécies Reativas de Oxigênio/metabolismo , Tripanossomicidas/isolamento & purificação
6.
Fitoterapia ; 137: 104250, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31271784

RESUMO

Obesity is associated with a number of metabolic disorders. Lipolysis is the initial step in the metabolism of lipids stored in adipocytes and is therefore considered a therapeutic target for obesity. Quassinoids are unique terpenes found in plants of the Simaroubaceae family, which were recently reported to have lipolytic activity and to suppress weight gain. Brucea javanica is a plant employed in traditional medicines in Asia, which is known to contain various quassinoids. Here, we investigated the lipolytic activity of B. javanica extracts, and identified six quassinoids: brucein A, brucein B, brucein C, 3'-hydroxybrucein A, brusatol, and bruceantinol, which represent the bioactive principals. The quassinoids contained in B. javanica demonstrated lipolytic activity at nanomolar concentrations, which were an order of magnitude lower than those of the previously reported quassinoids, suggesting that they may be useful for the treatment of obesity.


Assuntos
Adipócitos/efeitos dos fármacos , Brucea/química , Lipólise/efeitos dos fármacos , Quassinas/farmacologia , Células 3T3-L1 , Adipócitos/metabolismo , Animais , Frutas/química , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Quassinas/isolamento & purificação , Sementes/química
7.
Fitoterapia ; 137: 104255, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31271785

RESUMO

Nine biflavonoids (1-9) were isolated from ethanolic extract of Selaginella uncinata (Desv.) Spring. Their structures were determined by spectra analysis. Compounds 1-9 were classified into four types according to the connection styles of the two flavonoid parts. Among them, 1 was elucidated as a new compound, while 4 was one with a new configuration. All isolates exhibited inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) in an enzyme assay with IC50 values ranging from 4.6 to 16.1 µM, and the relationship between the structures and activities was discussed. Docking simulations of these compounds demonstrated they had tight binding capacities towards the allosteric site of PTP1B. Additionally, the glucose uptake activities of 1-9 were evaluated in insulin-resistant HepG2 cells, while the effect of 1 on the activation of IRS-1/PI3K/Akt pathway was revealed by Western Blot analysis.


Assuntos
Biflavonoides/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Selaginellaceae/química , Biflavonoides/isolamento & purificação , China , Células Hep G2 , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Transdução de Sinais/efeitos dos fármacos
8.
Fitoterapia ; 137: 104252, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31271787

RESUMO

The stems of Fissistigma polyanthoides (A.DC.) Merr. are traditionally used for the treatment of rheumatism and for recuperating women after childbirth. In our continuous phytochemical investigation of this plant, four new (1, 2, 5, and 19) and fifteen known (3, 4, and 6-18) phenolic compounds were isolated. The structures of all compounds were elucidated based on extensive spectroscopic analyses (1D-, 2D-NMR, and MS), and in comparison with reported literature data. The new natural products showed to be two poly-methoxylated chalcones (1 and 2) and two flavonoid glycosides, with 19 containing an uncommon sugar moiety (quinovose). Compounds with sufficient amount were tested for their anti-oxidant activity in a cell-based assay using the human bronchial epithelial cell line BEAS-2B. The compounds' capacity to inhibit the peroxyl radical triggered formation of dichlorofluorescein (DCF) was investigated in a dose-dependent manner. Both, anti-oxidant (3, 4, 6, 8-12, and 14) and pro-oxidative (5 and 16) properties were found for the investigated substances. The half maximal concentrations (IC50) for the inhibition of ROS formation ranged between 18.8 µM and 63.5 µM. Compounds, which acted protectively in the cellular antioxidant activity (CAA) assay and did not negatively affect cell viability, could be interesting targets for further investigations.


Assuntos
Annonaceae/química , Antioxidantes/farmacologia , Células Epiteliais/efeitos dos fármacos , Fenóis/farmacologia , Antioxidantes/isolamento & purificação , Linhagem Celular , Chalconas/isolamento & purificação , Chalconas/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Humanos , Estrutura Molecular , Fenóis/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química , Espécies Reativas de Oxigênio/metabolismo , Vietnã
9.
Fitoterapia ; 137: 104258, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31284017

RESUMO

Four new indole alkaloids (1-4) and twenty known compounds (5-24) were isolated from the leaves and stems, and fruits of Kopsia officinalis. Their structures were confirmed by means of spectroscopic methods. All these isolates were evaluated for their antagonizing high glucose-evoked podocyte injury activity for the first time, and compounds 5-8 showed potent activity with EC50 values of 3.0-12.0 µM.


Assuntos
Apocynaceae/química , Alcaloides Indólicos/farmacologia , Podócitos/efeitos dos fármacos , Animais , Células Cultivadas , China , Frutas/química , Glucose , Alcaloides Indólicos/isolamento & purificação , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Caules de Planta/química
10.
Fitoterapia ; 137: 104256, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31295513

RESUMO

Labisia pumila var. alata (Myrsinaceae) or "Kacip fatimah" is a famous Malay traditional herb used for the maintenance of women's health. The extracts of L.pumila displayed estrogenic activity in rats. Nonetheless, the estrogenic bioactives were not identified. The aim of the study is to identify estrogenic compounds contributing to the established estrogenic activity. Bioactivity-guided-isolation method guided the isolation of pure bioactives. The hexane extract was subjected to a series of silica gel flash and open column chromatography with increasing amount of ethyl acetate in hexane or methanol in chloroform. Each fraction or pure compounds were evaluated on it's estrogen receptor (ER) binding activity with the fluorescence polarization competitive ERα and ERß binding assay kit. Cytotoxic assay using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay method was used to establish the cytotoxic activity of the compounds. Four alkyl resorcinols and a dimeric 1,4-benzoquinone, namely belamcandol B (1), 5-pentadec-10'-(Z)-enyl resorcinol (2), 1,3-dihydroxy-5-pentadecylbenzene (3), 5-(heptadec-12'-(Z)-enyl) resorcinol (4) and demethylbelamcandaquinone B (5) were identified with selective binding affinities towards either ERα or ERß exhibiting selectivity ratio from 0.15-11.9. Alkyl resorcinols (2)-(4) exhibited cytotoxic activity towards HL60 cells with IC50 values from 19.5-22.0 µM. Structural differences between compounds influence the binding affinities to ER subtypes. Further study is needed to establish the agonist or antagonist effect of these compounds on various tissues and to identify if these compounds exert cytotoxic activity through the ERs. When consuming L.pumila as a complementary medicine, careful consideration regarding it's estrogenic compound content should be given due consideration.


Assuntos
Receptor alfa de Estrogênio/efeitos dos fármacos , Receptor beta de Estrogênio/efeitos dos fármacos , Estrogênios/farmacologia , Primulaceae/química , Benzoquinonas/isolamento & purificação , Benzoquinonas/farmacologia , Estrogênios/isolamento & purificação , Células HL-60 , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Resorcinóis/isolamento & purificação , Resorcinóis/farmacologia
11.
Fitoterapia ; 137: 104259, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31319108

RESUMO

The cyclooxygenase-2 (COX-2) is a key enzyme in the synthesis of prostaglandins, its inhibitors are effective for the treatment of inflammation. In this study, an analytical method based on bio-affinity ultrafiltration coupled with ultra performance liquid chromatography and quadrupole-time-of-flight mass spectrometry (BAUF-UPLC-Q-TOF-MS) was established for rapidly screening and identifying COX-2 ligands. Meanwhile, the specificity of the method was verified by denatured COX-2 and inactive compound. Next, the biological activity of ligands screened was proved by enzyme inhibition assay. The preferred binding modes for these COX-2 inhibitors were then determined by molecular docking. Finally, network pharmacology was used to explore the pathways involved anti-inflammatory effects. As a result, five COX-2 inhibitors were selected in the extract of Andrographis Herba (AH), including andrographolide (1), 14-deoxy-11,12-didehydroandrographiside (2), andrographidine E (3), andrographidine D (4), and deoxyandrographolide (5). Among them, compounds 2, 3, 4 and 5 were reported to have COX-2 inhibitory activity for the first time. The result of COX-2 inhibition assay showed that compound 3 had an IC50 of 19 µM, compounds 2 and 5 had an IC50 of >200 µM. And each ligand could bind to multiple amino acid residues of COX-2 based on molecular docking. At last, combined with network pharmacology, these ligands could exert anti-inflammatory effects through three pathways related to COX-2, arachidonic acid metabolism, synthesis of prostaglandins, and prostanoid ligand receptors. The method established in the study could be used to rapidly screen other enzyme inhibitors in complex mixtures, and help to understand the mechanism of action.


Assuntos
Andrographis/química , Inibidores de Ciclo-Oxigenase 2/farmacologia , Diterpenos/farmacologia , Cromatografia Líquida de Alta Pressão , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Diterpenos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Humanos , Inflamação , Espectrometria de Massas , Simulação de Acoplamento Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Ultrafiltração
12.
Zhongguo Zhong Yao Za Zhi ; 44(13): 2806-2812, 2019 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-31359694

RESUMO

A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-ß-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-ß-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-ß-D-galactopyranoside( 8),quercetin-3-O-ß-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.


Assuntos
Eriobotrya/química , Glicosídeos/isolamento & purificação , Mel , Cromatografia Líquida de Alta Pressão , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação
13.
Zhongguo Zhong Yao Za Zhi ; 44(13): 2835-2840, 2019 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-31359698

RESUMO

SATB1 plays a crucial role in the invasion and metastasis of breast cancer,and inhibition of SATB1 expression can effectively control breast cancer metastasis. In this study,homogeneous polysaccharides were isolated from Poria cocos and their sulfated derivatives were prepared to screen out the polysaccharide compositions with inhibitory effects on SATB1 expression. Smal-molecule components were removed from P. cocos by ethanol extraction,and P. cocos crude polysaccharide PPS was obtained by water extraction and ethanol precipitation. Then PPS was successively separated by DEAE Sepharose fast flow anion-exchange and Superdex-75 gel permeation chromatographic steps to give PPSW-1. The structure of PPSW-1 was identified and its sulfated derivatives were prepared. Then their inhibitory effects on human breast cancer MDA-MB-231 cells were investigated. A kind of polysaccharide,PPSW-1 with inhibitory effect on human breast cancer MDA-MB-231 cells,was obtained from P. cocos,with a relative molecular weight of 3. 06×104,and structure of 1,6-branched 1,3-α-D-galactan. PPSW-1 and its sulfated derivative Sul-W-1 showed good inhibitory effect on cells migration,and the water solubility of Sul-W-1 was better than that of PPSW-1. In addition,it was found that polysaccharide of P. cocos and its sulfated derivative can inhibit expression of SATB1. In this study,a kind of homogeneous polysaccharide with inhibitory effect on human breast cancer MDA-MB-231 cells was isolated from P. cocos,and its sulfated derivative with similar efficacy but better solubility was prepared,laying the foundation for the substance basis study of P. cocos.


Assuntos
Neoplasias da Mama/patologia , Polissacarídeos/farmacologia , Wolfiporia/química , Linhagem Celular Tumoral , Movimento Celular , Humanos , Proteínas de Ligação à Região de Interação com a Matriz/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Polissacarídeos/isolamento & purificação , Sulfatos
14.
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
15.
Fitoterapia ; 137: 104261, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31284019

RESUMO

Three new sesquilignans, zijusesquilignans A-C (1-3), together with fifteen known compounds (4-18), were isolated from fruits of Ziziphus jujuba var. inermis Rehder (Rhamnaceae). Their chemical structures were established using spectroscopic analyses including 1D- and 2D-NMR, HR-EIMS, and ECD spectra. These compounds were assessed for their inhibitory effects on nitric oxide (NO) production. Of these compounds, 1-3 and 17 displayed inhibitory effects on NO production, with IC50 values ranging from 18.1 to 66.4 µM. Pretreatment with 1 and 17 significantly suppressed LPS-induced expression of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein in cells. Moreover, compounds 1-3, 7, 9, and 17 exhibited cytotoxic activities against three human tumor cell lines, with IC50 values ranging from 8.4 to 44.9 µM.


Assuntos
Anti-Inflamatórios/farmacologia , Frutas/química , Lignanas/farmacologia , Ziziphus/química , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Ciclo-Oxigenase 2/metabolismo , Humanos , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , República da Coreia
16.
Fitoterapia ; 137: 104263, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31295512

RESUMO

Chemical examination of the gum-resin of Boswellia carterii resulted in the isolation and characterization of eighteen new cembrane-type diterpenoids, named as Boscartins P-AG (1-18) and eight known ones. Their structures were established on the basis of extensive spectroscopic (2D NMR, IR, CD, MS and X-ray) analysis in combination with modified Mosher's method. All compounds featured unusual 1,12-oxygenated tetrahydrofuran functionalities, and were evaluated for hepatoprotective activity against D-galactosamine-induced HL-7702 cell damage and cytotoxic activity against MCF-7 human breast cancer cell in vitro. Compounds 1, 6-10, 12-13, 16-17 and 21-25 (10 µM) showed some hepatoprotective activity against D-galactosamine-induced HL-7702 cell damage.


Assuntos
Boswellia/química , Diterpenos/farmacologia , Resinas Vegetais/química , Linhagem Celular , China , Diterpenos/isolamento & purificação , Humanos , Células MCF-7 , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
17.
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
18.
Fitoterapia ; 137: 104265, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31302252

RESUMO

The aromatic plants of Vitex negundo var. heterophylla are not only herb medicine but also a functional food and an industrial crop. Its leaves can be used as a functional food for improving human's health, but the previous studies mainly focused on the volatile constituents, lignans, and iridoids. Our research led to the isolation of four new terpenoids (1-4), together with fifteen known compounds including seven flavonoids (9-15), two jasmonates (7-8) and six terpenoids (5-6, 16-19) from the leaves. Among all these compounds, 1, 2, 11, and 19 exhibited strong inhibitory activity against NO production in lipopolysaccharide (LPS)-induced RAW264.7 macrophage. The anti-inflammatory mechanism of the most active compound (2) is related to the inhibition of iNOS and COX-2, and the suppression of NF-κB pathway. Therefore, terpenoids and flavonoids from the leaves of Vitex negundo var. heterophylla might be used as potential anti-inflammatory candidates for developing medicine or value-added functional food.


Assuntos
Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Norisoprenoides/farmacologia , Vitex/química , Animais , Anti-Inflamatórios/isolamento & purificação , China , Ciclo-Oxigenase 2/metabolismo , Diterpenos/isolamento & purificação , Interleucinas/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/metabolismo , Norisoprenoides/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Células RAW 264.7
19.
Fitoterapia ; 137: 104268, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31306720

RESUMO

Solanum nigrum L. (also called as European black nightshade) has been traditionally used as folk medicine and food in some regions. Phytochemical investigations of the immature fruits of S. nigrum yielded five steroidal alkaloid glycosides (1-5), including an unprecedented nor-spirosolane type steroidal alkaloid with a five-membered ring A (1) and two novel spirosolane type steroidal alkaloid glycosides (2, 3), together with eight known phenolic compounds (6-13). Their structures were elucidated on the basis of spectroscopic and chemical methods, including IR, NMR, HR-ESI-MS, and GC analyses. Five steroidal alkaloid glycosides were tested for their potential antiproliferative effects against HL-60, U-937, Jurkat, K562, and HepG2 cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7. Compound 1 exhibited significant inhibition on NO production with an IC50 value of 23.4 ±â€¯2.0 µM, compared to positive control indomethacin (IC50, 47.40 ±â€¯4.50 µM). Compound 4 exhibited significant cytotoxicity against all tested cell lines.


Assuntos
Alcaloides/farmacologia , Glicosídeos/farmacologia , Solanum nigrum/química , Esteroides/farmacologia , Alcaloides/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , China , Frutas/química , Glicosídeos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Células RAW 264.7 , Esteroides/isolamento & purificação
20.
Fitoterapia ; 137: 104271, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31326416

RESUMO

Three new neolignan glycosides, (7R,8S)-4-hydroxy-3,3'-dimethoxy-8,4'-oxyneoligna-7,9,9'-triol-4-O-ß-d-glucopyranosyl-(1 → 4)-ß-D-glucopyranoside (1), (7R,8S)-4-hydroxy-3,5'-dimethoxy-4',7-epoxy-8,3'-neoligna-9,9'-diol-9'-O-ß-d-glucopyranosyl-4-O-[ß-d-glucopyranosyl-(1 → 4)]-ß-D-glucopyranoside (2), and (7R,8S)-4-hydroxy-3,5,5'-trimethoxy-4',7-epoxy-8,3'-neoligna-9,9'-diol-9'-O-ß-d-glucopyranosyl-4-O-[ß-d-glucopyranosyl-(1 → 4)]-ß-D-glucopyranoside (3), one new phenolic glycoside, securiphenoside B (4) and two new hemiterpene glycosides, securiterpenoside E-F (5-6) were isolated from the stems of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of 1D and 2D NMR, HRESIMS, CD and chemical evidence. Furthermore, compound 2 showed moderate hepatoprotective activity compared with bicyclol in vitro.


Assuntos
Glicosídeos/farmacologia , Caules de Planta/química , Securidaca/química , China , Glicosídeos/isolamento & purificação , Células Hep G2 , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
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