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1.
Fitoterapia ; 139: 104411, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31705951

RESUMO

Eleven sesquiterpenoids including four new eudesmane sesquiterpenoids, solanoids A-D (1-4), and seven known compounds (5-11) were isolated from the herbs of Solanum lyratum. By analyzing the UV, MS and NMR data, the gross structures of all isolates were established. The absolute configurations of these new compounds were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The in vitro cytotoxicity of all isolates against the hepatocellular carcinoma Hep3B and HepG2 cell lines was evaluated. Among them, compounds 7 and 11 exhibited moderate cytotoxicity against two cell lines.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Sesquiterpenos de Eudesmano/farmacologia , Solanum/química , Antineoplásicos Fitogênicos/isolamento & purificação , China , Células Hep G2 , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Sesquiterpenos de Eudesmano/isolamento & purificação
2.
Hum Exp Toxicol ; 38(10): 1132-1144, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31203647

RESUMO

BACKGROUND: Gastric cancer is a malignant tumor with high incidence rate and mortality rate. PURPOSE: In this study, we investigated the anti-cancer effect of alantolactone, a sesquiterpene lactone, on gastric cancer cell lines BGC-823 and SGC-7901. METHODS: BGC-823 and SGC-7901 cells were treated with different concentrations of alantolactone, Hoechst 33258 staining, flow cytometry, wound healing assay, invasion assay, colony forming assay, quantative polymerase chain reaction, and western blot analysis were used to evaluate the anticancer activity of alantolactone to gastric cancer. RESULTS: Alantolactone induced apoptosis of gastric cancer cells by regulating the expression of Bax, Bcl-2, and p53, which related to intrinsic apoptotic pathway, and suppressed colony formation, migration, and invasion by mediating the expression of matrix metalloproteinase (MMP)-2, MMP-7, and MMP-9. Cell signaling pathway analysis showed that alantolactone enhanced the phosphorylation of p38 and decreased the translocation of nucleus p65, suggesting that the apoptosis-promoting and migration-suppressing effect of alantolactone might at least partially rely on regulating p38 mitogen-activated protein kinase (p38MAPK) pathway and nuclear factor-κB (NF-κB) pathway. CONCLUSIONS: Alantolactone can be used as a potential therapeutic agent for treating gastric cancer.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Movimento Celular/efeitos dos fármacos , Lactonas/farmacologia , NF-kappa B/metabolismo , Sesquiterpenos de Eudesmano/farmacologia , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismo , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Inula/química , Lactonas/isolamento & purificação , Sesquiterpenos de Eudesmano/isolamento & purificação , Transdução de Sinais , Neoplasias Gástricas/metabolismo , Neoplasias Gástricas/patologia
3.
Zhongguo Zhong Yao Za Zhi ; 44(1): 95-99, 2019 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-30868818

RESUMO

Six compounds were isolated from the aerial part of cultivated Clerodendranthus spicatus in Hainan with various chromatographic techniques,and their structures were determined as:1-dehydroxy-1-oxo-rupestrinol(1),N-trans-feruloyltyramine(2),methyl 3,4-dihydroxyphenyllactate(3),caffein acid(4),methyl caffeate(5) and ethyl caffeate(6),via analysis of physicochemical properties and spectroscopic evidence.Compound 1 was a new compound,while compounds 2 and 3 were isolated from C.spicatus for the first time.Biological activity results showed that compounds 2-4 exhibited α-glucosidase inhibitory activity with different inhibition ratio.


Assuntos
Inibidores de Glicosídeo Hidrolases/farmacologia , Lamiaceae/química , Sesquiterpenos de Eudesmano/farmacologia , China , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Sesquiterpenos de Eudesmano/isolamento & purificação
4.
Free Radic Res ; 53(1): 104-114, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30668191

RESUMO

Thioredoxin reductase 1 (TrxR1) has emerged as a potential target for cancer therapy, because it is overexpressed in several types of cancers and associated with increased tumour growth and poor patient prognosis. Alantolactone (ALT), a natural sesquiterpene lactone originated from traditional folk medicine Inula helenium L., has been reported to exert antitumor activity in various tumours. However, the effect of ALT on human gastric cancer cells and its underlying mechanism remains unknown. In this study, we showed that ALT inhibited cell proliferation and induced cell apoptosis in gastric cancer cells. Mechanistically, our data found that ALT induced reactive oxygen species (ROS) production by inhibiting TrxR1 activity, resulting in the activation of p38 mitogen-activated protein kinase (MAPK) pathway and eventually cell apoptosis in gastric cancer cells. And the effects of ALT were reversed by pre-treatment with NAC (a scavenger of ROS). Further investigation revealed that ALT displayed synergistic lethality with erastin against gastric cancer cells, which demonstrating combined inhibition of TrxR1 and glutathione (GSH) leads to a synergistic effect in gastric cancer cells. More importantly, ALT treatment markedly reduced the activity of TrxR1 in vivo and inhibited the growth of gastric cancer xenografts without exhibiting significant toxicity. Taken together, these findings suggest that ALT may be used as a novel therapeutic agent against human gastric cancer.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Lactonas/farmacologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos de Eudesmano/farmacologia , Neoplasias Gástricas/tratamento farmacológico , Neoplasias Gástricas/patologia , Tiorredoxina Redutase 1/antagonistas & inibidores , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismo , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Inula/química , Lactonas/química , Lactonas/isolamento & purificação , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Neoplasias Experimentais/tratamento farmacológico , Neoplasias Experimentais/metabolismo , Neoplasias Experimentais/patologia , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Neoplasias Gástricas/metabolismo , Relação Estrutura-Atividade , Tiorredoxina Redutase 1/metabolismo , Células Tumorais Cultivadas
5.
Eur J Drug Metab Pharmacokinet ; 44(2): 295-303, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30209793

RESUMO

BACKGROUND: Isoalantolactone and alantolactone are the main sesquiterpene lactones in Radix Inulae (dried root of Inula helenium L. or I. racemosa Hook. F.), which is a frequently utilized herbal medicine. They also occur in several plants and have various pharmacologic effects. However, they have been found to have poor oral bioavailability in rats. OBJECTIVES: To understand the intestinal absorptive characteristics of isoalantolactone and alantolactone as well specific influx and efflux transporters in their absorption. METHODS: Bidirectional permeabilities of isoalantolactone and alantolactone were investigated across Caco-2 cell monolayers. Transport assays were performed using different concentrations of two lactones and specific inhibitors of ATP-binding cassette transporters and influx transporters. RESULTS: The absorption permeability of isoalantolactone and alantolactone was high at the tested concentrations (5, 20 and 80 µmol/l), and the major permeation mechanism of both lactones was found to be passive diffusion with active efflux mediated by multidrug resistance-associated proteins (MRPs) and breast cancer resistance protein (BCRP). CONCLUSION: Our results demonstrated that the absorption permeability of isoalantolactone and alantolactone was good in the Caco-2 cell model. The isoalantolactone and alantolactone absorption elucidated in this study provides useful information for further pharmacokinetics studies. Since low intestinal absorption can now be ruled out as a cause, further studies are needed to explain the low oral bioavailability of the two sesquiterpene lactones.


Assuntos
Absorção Intestinal , Inula/química , Lactonas/farmacocinética , Sesquiterpenos de Eudesmano/farmacocinética , Sesquiterpenos/farmacocinética , Administração Oral , Disponibilidade Biológica , Células CACO-2 , Relação Dose-Resposta a Droga , Humanos , Lactonas/administração & dosagem , Lactonas/isolamento & purificação , Permeabilidade , Raízes de Plantas , Sesquiterpenos/administração & dosagem , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Eudesmano/administração & dosagem , Sesquiterpenos de Eudesmano/isolamento & purificação
6.
Fitoterapia ; 130: 265-271, 2018 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30243779

RESUMO

Gracilistones A (1) and B (2), two new eudesmane-type sesquiterpenoids with an unusual tetrahydrofuran-fused 6/6/5 tricyclic ring system, were obtained from Acanthopanax gracilistylus under the guidance of LC-MS investigation. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and quantum calculation methods. Compounds 1 and 2 showed potent inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages, compared with the positive control L-NMMA. In addition, compounds 1 and 2 were also evaluated for their antioxidant (DPPH• and ABTS•+) and xanthine oxidase (XO) inhibitory activities, and they exhibited weak inhibitory effects at 100 µM.


Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Eleutherococcus/química , Sesquiterpenos de Eudesmano/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antioxidantes/isolamento & purificação , China , Cromatografia Líquida , Furanos , Espectrometria de Massas , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Células RAW 264.7 , Sesquiterpenos de Eudesmano/isolamento & purificação
7.
Molecules ; 23(3)2018 Mar 13.
Artigo em Inglês | MEDLINE | ID: mdl-29533968

RESUMO

Eudesmane-type sesquiterpenes have been reported to exhibit varieties of biological activities. During the process of investigating this kind of natural product from the root bark of Dictamnus dasycarpus Turcz., 13 eudesmane-type sesquiterpene glycosides including six new isolates, named as dictameudesmnosides A1 (1), A2 (2), B (3), C (4), D (5), and E (6), together with seven known ones (7-13), were obtained. Herein, their structures were determined by the analysis of physical data, spectroscopic analysis, and chemical methods. The existence of α-configuration glucose units in their structures (1-5, 8) is not very common in natural glycosidic components. Meanwhile, compounds 3-5, 7, and 9-13 displayed TG accumulation inhibitory effects on HepG2 cells.


Assuntos
Dictamnus/química , Glicosídeos/isolamento & purificação , Sesquiterpenos de Eudesmano/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Estrutura Molecular , Casca de Planta/química , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia
8.
J Nat Prod ; 80(10): 2666-2676, 2017 10 27.
Artigo em Inglês | MEDLINE | ID: mdl-28960981

RESUMO

Nine new sesquiterpenoid lactones and 11 known analogues were isolated from the aerial parts of Salvia plebeia R.Br. Their structures were elucidated via HRESIMS and NMR data, and their absolute configurations were defined via electronic circular dichroism data, X-ray crystallographic analysis, and the modified Mosher's ester method. Compounds 1-20 were investigated for their ability to inhibit LPS-stimulated nitric oxide production in murine macrophage cells. Of the isolates, epi-eudebeiolide C (20) showed the highest inhibitory effect (IC50 of 17.9 µM). mRNA and protein expression of inducible nitric oxide synthase (iNOS), but not that of cyclooxygenase-2 (COX-2), was dose-dependently decreased by 20 in LPS-activated RAW 264.7 cells. Based on a mechanistic study involving the nuclear factor-κB (NF-κB) signaling pathway, the anti-inflammatory effect of 20 was attributed to NF-κB activation blockade via inhibition of NF-κB (IκB) phosphorylation. Therefore, 20 might be a potential candidate for relieving inflammatory diseases.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Componentes Aéreos da Planta/química , Salvia/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Eudesmano/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios não Esteroides/farmacologia , Ciclo-Oxigenase 2/metabolismo , Dinoprostona/metabolismo , Proteínas I-kappa B/metabolismo , Lactonas/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , NF-kappa B/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Ressonância Magnética Nuclear Biomolecular , República da Coreia , Sesquiterpenos de Eudesmano/química , Transdução de Sinais/efeitos dos fármacos
9.
Bioorg Med Chem ; 25(20): 5764-5771, 2017 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-28935182

RESUMO

We isolated twelve sesquiterpenes from Chinese liverwort Tritomaria quinquedentata (Huds.) Buch., including four new compounds. Among them, five eudesmane sesquiterpenes were ineffective against Candida albicans wild strain SC5314 but active towards efflux pumps-deficient strain DSY654 using Alamar blue assay. Further test of the most active agent of ent-isoalantolactone (8, ent-iLL) showed that it also inhibited the yeast-to-hyphal switch of DSY654 cells. The intracellular content measurement using high performance liquid chromatography (HPLC) revealed that ent-iLL was intracellularly accumulated in C. albicans when efflux pumps were deficient or inhibited by Cdrs inhibitor riccardin D, suggesting that the activity of ent-iLL was compromised by efflux pumps Cdrs. Moreover, ent-iLL potentially inhibited the activity of Erg11 and Erg6 of DSY654 and thereby resulted in the alteration of sterol composition by decreasing ergosterol contents and increasing zymosterol and lanosterol accumulation. Our study demonstrated that eudesmane sesquiterpenes, as the substrates of Cdrs, could interfere with sterol synthesis of C. albicans to exert antifungal activity when co-applied with Cdrs inhibitors.


Assuntos
Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Hepatófitas/química , Sesquiterpenos de Eudesmano/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Sistema Enzimático do Citocromo P-450/metabolismo , Sistemas de Liberação de Medicamentos , Metiltransferases/antagonistas & inibidores , Metiltransferases/metabolismo , Proteínas de Saccharomyces cerevisiae/antagonistas & inibidores , Proteínas de Saccharomyces cerevisiae/metabolismo , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Especificidade por Substrato
10.
Phytochemistry ; 143: 194-198, 2017 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-28843162

RESUMO

Chemical analysis of the dichloromethane fraction obtained from aerial parts of the Northern African endemic plant Daucus virgatus led to the isolation of three previously undescribed sesquiterpenoids, namely the daucane vaginatin B, a eudesmane and the elemane elemavirgolide, along with five known metabolites. The structures of these compounds were determined by a detailed MS and NMR analysis and they were evaluated for antiproliferative activity against three human cell lines, A375 (melanoma), MCF-7 (breast adenocarcinoma), and HACAT (keratinocyte). The phytoalexin 6-methoxymellein revealed a previously unreported antiproliferative activity, while the eudesmane and the elemane derivatives exhibited a selective activity (SI = 11.1 and 3.3, respectively) against melanoma tumor cell lines.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Apiaceae/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Eudesmano/farmacologia , Antineoplásicos Fitogênicos/química , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Isocumarinas/química , Isocumarinas/isolamento & purificação , Isocumarinas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Componentes Aéreos da Planta/química , Sesquiterpenos , Sesquiterpenos de Eudesmano/química
11.
Artigo em Inglês | MEDLINE | ID: mdl-28837869

RESUMO

Alantolactone and isoalantolactone isolated from many species of plants are a pair of positional isomers of CC bond. Previously, alantolactone and isoalantolactone have been proved to be good lead compounds for future anticancer agent development. Similarity of their molecular structures increases the separation difficulty for these two isomers on a conventional C18 column. Silver perchlorate (AgClO4) as mobile phase additives with RP-HPLC for improving the separation was developed for rapid determination of the positional isomers in Inula racemosa Hook.f. The effects of the concentration of silver perchlorate on the separation of the analytes were investigated. The composition of acetonitrile and water containing 5.0% silver perchlorate in a 65:35 (v/v) ratio was used as mobile phase, in which they were well separated within a short period of time on the C18 column. The method was successfully applied to determine them in an extract of Inula racemosa Hook.f. root. Silver perchlorate in mobile phase can efficiently improve the separation of the positional isomers and could be applied to rapidly determinate their content in this plant.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Inula/química , Lactonas/isolamento & purificação , Percloratos/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Compostos de Prata/química , Acetonitrilos/química , Cromatografia de Fase Reversa/métodos , Isomerismo , Lactonas/análise , Lactonas/química , Extratos Vegetais/química , Raízes de Plantas/química , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos de Eudesmano/análise , Sesquiterpenos de Eudesmano/química
12.
Bioorg Med Chem Lett ; 27(16): 3825-3828, 2017 08 15.
Artigo em Inglês | MEDLINE | ID: mdl-28676273

RESUMO

While select eudesmane sesquiterpenes exhibit anti-neoplastic activity, tumor-inhibition for costic-acids has not been established. Here biological activity of 3-oxo-γ-costic acid (1), previously isolated from Chiliadenus montanus, as well as new sesquiterpenes (2-5) and the known derivative, 3-oxoeudesma-1,4,11(13)-trien-7-1061αH-l2-oic acid (6), all produced from 1 by the fungus Athelia rolfsii, are reported. Structures were elucidated using MS and NMR spectroscopy with activity-screening utilizing human colon- and lung-tumor lines, Caco-2 and A549 respectively. Compound 1 exhibited anti-proliferative activity against Caco-2 (IC50 39µM) and 2 was active against A549 (IC50 74µM) suggesting therapeutic potential for the original substrate and a bio-transformed product.


Assuntos
Antineoplásicos/farmacologia , Basidiomycota/química , Sesquiterpenos de Eudesmano/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Relação Estrutura-Atividade
13.
Phytochemistry ; 141: 37-47, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28554035

RESUMO

The traditionally used Central American medicinal plant Pluchea odorata, known as an anti-inflammatory and cancer cell growth-inhibiting remedy, was subjected to bioassay-guided isolation. Structure elucidation by 1D- and 2D-NMR and MS techniques supported by ECD and UV spectroscopic data revealed seven structurally previously undescribed and eight known eudesmane-type sesquiterpenes. Furthermore, one previously undescribed and one known phytol-like alcohol were identified. All compounds were tested for their cytotoxicity in cancer cells and for their anti-invasive effects. Among the eudesmanes, 3α-(2',3'-epoxy-2'-methylbutyryloxy)-4α-hydroxy-11-hydroperoxy-eudesm-6-en-8-one exhibited the most potent cytotoxic activity with an IC50 value of 8.8 µM (after 48 h). Also in an in vitro model measuring the tumor-triggered breaching of the adjacent lymph endothelial cell barrier (3S*,4R*,5S*,10S*,2'R*,3'R*)-3-(2',3'-epoxy-2'-methylbutyryloxy)-4,7-dihydroxy-eudesm-11-en-8-one (IC75 = 47 µM) and (3S*,4R*,5R*,10S*,2'R*,3'R*)-3-(2',3'-epoxy-2'-methylbutyryloxy)-4-acetyloxy-6-methoxy-11-hydroxy-eudesm-6-en-8-one (IC75 = 73 µM) showed inhibitory activities. Furthermore, preliminary structure-activity relationships (SARs) of the eudesmanes were developed.


Assuntos
Asteraceae/química , Sesquiterpenos de Eudesmano/farmacologia , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Invasividade Neoplásica , Sesquiterpenos de Eudesmano/isolamento & purificação , Relação Estrutura-Atividade
14.
Bioorg Med Chem Lett ; 27(11): 2579-2582, 2017 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-28400238

RESUMO

A new eudesmane sesquiterpenoid (1), and a new homologue of virginiae butanolide E (2) along with butyl isobutyl phthalate (3) were isolated from, actinomycete-Lentzea violacea strain AS08 isolated from north western Himalayas by stressing on modified one strain-many compounds (OSMAC) method. The structures of the new compounds were elucidated by extensive spectroscopic analyses including 1D, 2D NMR along with HR-ESI-MS and FT-IR data. Herein, a distinctive method was added for inspecting secretory profile of the strain by quantification of extract value of cell free supernatant in different types of culture media fallowed by HPLC profiling of respective extracts, which revealed a highly altered metabolic profile of the strain and formed the base for the selection of media. The compounds 1 and 2 showed moderate activity against Gram negative (MIC ∼32-64µgml-1) in comparison to Gram positive bacterial pathogens. Compound 1 exhibited significant activity in human cancerous cell lines (IC50 ∼19.2µM).


Assuntos
Actinobacteria/química , Antibacterianos/química , Antineoplásicos/química , Sesquiterpenos de Eudesmano/química , Actinobacteria/metabolismo , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Conformação Molecular , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Eudesmano/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectroscopia de Infravermelho com Transformada de Fourier
15.
Chem Biodivers ; 14(8)2017 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-28452167

RESUMO

Three new sesquiterpenoids, salplebeones A - C (1 - 3), were isolated from the ethanol-soluble extract of the aerial part of Salvia plebeia R. Br. Their structures were established by detailed analysis of NMR and MS spectra. Salplebeone A was an eudesmane lactone, while salplebeones B and C were rare eudesmane sesquiterpenoids, containing 12,8-lactam groups. Antiproliferative activities of salplebeones A - C to myeloid leukemia cell lines were evaluated.


Assuntos
Salvia/química , Sesquiterpenos de Eudesmano/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Conformação Molecular , Salvia/metabolismo , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Eudesmano/farmacologia
16.
Fitoterapia ; 119: 90-99, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28408269

RESUMO

Two new eudesmane sesquiterpenoids, chlorajaponols A-B (1-2), two new guaiane sesquiterpenoids, chlorajaponols C-D (3-4), a new germacrane sesquiterpenoid, chlorajaponol E (5), and a new lindenane sesquiterpenoid, chlorajaponol F (6), along with 8 known sesquiterpenoids and 6 known disesquiterpenoids, were isolated from the whole plant of Chloranthus japonicus. Their structures were established by extensive analysis of NMR spectroscopic data in combination with mass spectrometry. The structures of compounds 1-4 were confirmed by single crystal X-ray diffraction (CuKα radiation). The possible biogenetic pathways of compounds 1-6 were discussed. Chlorajaponol B (2) showed significant inhibition against nitric oxide (NO) release in LPS-induced RAW264.7 macrophages with the IC50 value of 9.56±0.71µM, comparable to that of positive control amino guanidine (8.50±0.35µM). Shizukaol C (18) strongly suppressed the proliferation of three human tumor cell lines MGC803, HepG2, and HL-60 with IC50 values of 4.60±1.05µM, 3.17±0.66µM, and 1.57±0.27µM, respectively.


Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Magnoliopsida/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Guaiano/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Guaiano/isolamento & purificação
17.
Fitoterapia ; 118: 73-79, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28232217

RESUMO

Eleven new sesquiterpenoids, including eight cadinane-type sesquiterpenoids, Ganodermanol A-H (1-8), and three eudesmane-type sesquiterpenoids, Ganodermanol I-K (9-11), together with three known compounds (12-14), were isolated from the cultured mycelia of Ganoderma capense. Their structures and absolute configurations were identified through combined extensive spectroscopic analysis, circular dichroism (CD), and Mo2(AcO)4-induced CD. Compounds 4 and 9 exhibited moderate cytotoxic activity against the human cancer cell line HCT116 with IC50 values of 16.6 and 12.2µM, respectively.


Assuntos
Ganoderma/química , Sesquiterpenos de Eudesmano/química , Sesquiterpenos/química , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Micélio/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Eudesmano/isolamento & purificação
18.
J Asian Nat Prod Res ; 19(7): 666-672, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27989219

RESUMO

A rare carotane-type sesquiterpenoid, forkienin A (1), a new eudesmane-type sesquiterpenoid, forkienin B (2), and a new natural eudesmane-type sesquiterpenoid, forkienin C (3), were isolated from the twigs and leaves of Fokienia hodginsii, along with eight known sesquiterpenoids. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, including 1D and 2D NMR methods. All compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Folhas de Planta/química , Caules de Planta/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Células HL-60 , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia
19.
Fitoterapia ; 116: 24-33, 2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-27984167

RESUMO

Six eremophilane-type (parasenolide A-F) and an eudesmane-type (parasenin) sesquiterpenoids, along with eight known sesquiterpenes, were isolated from the whole plants of Parasenecio roborowskii. The structures and absolute configurations of new compounds were elucidated using extensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR experiments, the CD exciton chirality methods, and single-crystal X-ray crystallography. All isolated compounds were evaluated for cytotoxicity against five human cancer (HeLa, HepG2, K562, MDA231, and NCI-H460) cell lines and a murine melanoma B16 F10 cell line by MTT assay. Compounds 1-15 showed cytotoxic activities, especially compounds 3, 4, 8, 10, and 12. These five compounds showed broad spectrum activities against all the tested cancer cell lines with IC50 ranging from 9.2 to 35.5µM. The study supports that eremophilenolides and eudesmane-type sesquiterpenes occur mainly in the genus Parasenecio and can be used as a chemosystematic marker of the genus.


Assuntos
Antineoplásicos Fitogênicos/farmacocinética , Asteraceae/química , Sesquiterpenos/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Melanoma Experimental , Camundongos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos de Eudesmano/farmacocinética
20.
Arch Pharm Res ; 39(12): 1628-1634, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27620498

RESUMO

A new rearranged eudesmane sesquiterpene, named eudeglaucone (1), and five known sesquiterpenes including (+)-faurinone (2) and four eudesmane-type sesquiterpenes (3-6), were isolated from the twigs of Lindera glauca (Sieb. et Zucc.) Blume. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including extensive 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY) and HR-MS. Compound 1 was a relatively rare rearranged eudesmane sesquiterpene in terpenoids. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 3 and 6 showed significant cytotoxicity against SK-MEL-2 and HCT-15 cell lines with IC50 values ranging from 9.98 to 12.20 µM. We also investigated the anti-neuroinflammatory activities of the isolates (1-6) in the lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cell line by measuring nitric oxide (NO) levels. All isolates significantly inhibited NO production with IC50 values of 3.67-26.48 µM without inducing cell toxicity.


Assuntos
Lindera , Caules de Planta , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Animais , Linhagem Celular Tumoral , Humanos , Camundongos , Microglia/efeitos dos fármacos , Microglia/fisiologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/farmacologia
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