RESUMO
The synthesis of N-{4-[a-(1-adamantyl)benzyl]phenyl}piperazines 2a-e is described. The in vitro antiproliferative activity of most compounds against main cancer cell lines is significant. The σ(1), σ(2)-receptors and sodium channels binding affinity of compounds 2 were investigated. One of the most active analogs, 2a, had an interesting in vivo anticancer profile against the BxPC-3 and Mia-Paca-2 pancreas cancer cell lines with caspase-3 activation, which was associated with an anagelsic activity against the neuropathic pain.
Assuntos
Adamantano , Antineoplásicos , Receptores sigma/metabolismo , Adamantano/síntese química , Adamantano/química , Adamantano/farmacologia , Animais , Antineoplásicos/síntese química , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Camundongos , Camundongos Nus , Estrutura Molecular , Neoplasias Pancreáticas/metabolismoRESUMO
From the roots of Atriplex glauca L. var. ifiniensis (Caball) Maire (syn. of Atriplex parvifolia Lowe var. genuina Maire), three new saikosaponins designated as glaucasides A-C (1-3) were isolated together with the known 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-galactopyranosyl-saikogenin F (4). The structures of the new compounds were elucidated by extensive analysis of one-dimensional and two-dimensional NMR spectroscopy, FABMS, HR-ESIMS and chemical evidence as 13ß,28-epoxy-16ß,21ß-dihydroxyolean-11-en-3ß-yl O-ß-D-[2-O-sulfate]-glucopyranosyl-(1 â 2)-α-L-arabinopyranoside (1), 13ß,28-epoxy-16ß,21ß-dihydroxyolean-11-en-3ß-yl O-ß-D-[2-O-sulfate]-glucopyranosyl-(1 â 2)-α-L-arabinopyranosyl 21-O-{4-(secbutylamido)-butanoyl ester} (2) and 3-O-ß-D-glucopyranosyl-(1 â 2)-ß-D-galactopyranosyl saikogenin G (3). The cytotoxic activities of these compounds were evaluated against the HT-29 and HCT 116 human colon cancer cell lines.
Assuntos
Atriplex/química , Ácido Oleanólico/análogos & derivados , Saponinas/isolamento & purificação , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Saponinas/química , Saponinas/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
Dendritic cells (DCs) and macrophages are professional antigen-presenting cells (APCs) that play key roles in both innate and adaptive immunity. ChemR23 is an orphan G protein-coupled receptor related to chemokine receptors, which is expressed specifically in these cell types. Here we present the characterization of chemerin, a novel chemoattractant protein, which acts through ChemR23 and is abundant in a diverse set of human inflammatory fluids. Chemerin is secreted as a precursor of low biological activity, which upon proteolytic cleavage of its COOH-terminal domain, is converted into a potent and highly specific agonist of ChemR23, the chemerin receptor. Activation of chemerin receptor results in intracellular calcium release, inhibition of cAMP accumulation, and phosphorylation of p42-p44 MAP kinases, through the Gi class of heterotrimeric G proteins. Chemerin is structurally and evolutionary related to the cathelicidin precursors (antibacterial peptides), cystatins (cysteine protease inhibitors), and kininogens. Chemerin was shown to promote calcium mobilization and chemotaxis of immature DCs and macrophages in a ChemR23-dependent manner. Therefore, chemerin appears as a potent chemoattractant protein of a novel class, which requires proteolytic activation and is specific for APCs.
Assuntos
Células Apresentadoras de Antígenos/fisiologia , Quimiocinas/fisiologia , Receptores de Quimiocinas/metabolismo , Sequência de Aminoácidos , Cálcio/metabolismo , Movimento Celular , Quimiocinas/química , Quimiocinas/genética , Quimiocinas/isolamento & purificação , Células Dendríticas/fisiologia , Humanos , Peptídeos e Proteínas de Sinalização Intercelular , Dados de Sequência MolecularRESUMO
Six new spirostane-type saponins (1-6), named orchidastrosides A-F, and chloromaloside D were isolated from an ethanol extract of the roots of Chlorophytum orchidastrum. The saponins have neotigogenin or neogitogenin as the aglycon and oligosaccharidic chains possessing seven to nine sugar units. Their structures were elucidated mainly by 2D NMR spectroscopic analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and FABMS and HRESIMS. Compounds 1-6 were tested for cytotoxicity against two human colon cancer cell lines, HCT 116 and HT-29.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Liliaceae/química , Saponinas/isolamento & purificação , Espirostanos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , França , Células HCT116/efeitos dos fármacos , Células HT29 , Humanos , Estrutura Molecular , Raízes de Plantas/química , Saponinas/química , Saponinas/farmacologia , Espirostanos/química , Espirostanos/farmacologiaRESUMO
Four new steroidal saponins (1-4) were isolated from the stem and bark of two species of Dracaena: deistelianosides A and B (1 and 2) from D. deisteliana and arboreasaponins A and B (3 and 4) from D. arborea. Six known saponins and one known sapogenin were also isolated. The structures of 1-4 were established as diosgenin 3-O-[3-O-sulfate-alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (1), 1-O-beta-d-xylopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-fucopyranosyl(23S,24S)-spirosta-5,25(27)-diene-1beta,3beta,23alpha,24alpha-tetrol 24-O-alpha-l-arabinopyranoside (2), pennogenin-3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-[6-O-acetyl]-beta-d-glucopyranoside (3), and 24alpha-hydroxypennogenin 3-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->3)]-beta-d-glucopyranoside (4) using extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry. Cytotoxic activity of several of these compounds was evaluated against the HT-29 and HCT 116 human colon cancer cell lines.
Assuntos
Dracaena/química , Plantas Medicinais/química , Saponinas/isolamento & purificação , Esteroides/isolamento & purificação , Camarões , Células HCT116 , Células HT29 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Caules de Planta , Saponinas/química , Saponinas/farmacologia , Estereoisomerismo , Esteroides/química , Esteroides/farmacologiaRESUMO
Two new triterpene saponins ( 1- 2) together with three known saponins, deglucocyclamin I ( 3), cyclamin ( 4), and mirabilin ( 5), were isolated from the tubers of Cyclamen trocopteranthum. They were elucidated as 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-13 beta,28-epoxy-oleanan-30-al ( 1) and 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)-[ beta-D-glucopyranosyl-(1 --> 6)]- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-20,30-lactone-olean-12-ene ( 2). Their structures were characterized mainly by a combination of 1D- and 2D-NMR techniques ( (1)H- (1)H COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectroscopy. Saponins 1, 3, and 4 showed a weak cytotoxic activity when tested against HT-29 and HCT 116 tumor colon cancer cells.
Assuntos
Cyclamen/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Sequência de Carboidratos , Linhagem Celular Tumoral , Humanos , Espectroscopia de Ressonância Magnética , Saponinas/química , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/químicaRESUMO
From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (1) and gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116).
Assuntos
Caryophyllaceae/química , Ácido Oleanólico/análogos & derivados , Configuração de Carboidratos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ácido Oleanólico/química , Especificidade da EspécieRESUMO
A new sesquiterpene ester, tunetanin A (1), a new sesquiterpene coumarin, tunetacoumarin A (2), together with eight known compounds, i.e., coladin (3), coladonin (4), isosmarcandin (5), 13-hydroxyfeselol (6), umbelliprenin (7) propiophenone (8), beta-sitosterol (9), and stigmasterol (10), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D- and 2D-NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1-7 towards two human colon cancer cell lines, HT-29 and HCT 116, was evaluated. Compounds 3, 4, and 6 showed weak cytotoxic activities.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Cumarínicos/isolamento & purificação , Ferula/química , Raízes de Plantas/química , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cumarínicos/química , Cumarínicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Especificidade da Espécie , Relação Estrutura-AtividadeRESUMO
Five new triterpene saponins, arboreasides A-E (1-5), and two known saponins, ciwujianoside C(3) and 23-hydroxyursolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, were isolated from the bark of Cussonia arborea. The structures were established using extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry.
Assuntos
Araliaceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Camarões , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Saponinas/química , Triterpenos/químicaRESUMO
Four new spirostane-type saponins named borivilianosides E-H (1-4) were isolated from an ethanol extract of the roots of Chlorophytum borivilianum together with two known steroid saponins (5 and 6). The structures of 1-4 were elucidated using mainly 2D NMR spectroscopic techniques and mass spectrometry. The cytotoxicity of borivilianosides F (2), G (3), and H (4) and three known compounds was evaluated using two human colon cancer cell lines (HT-29 and HCT 116).
Assuntos
Asparagaceae/química , Plantas Medicinais/química , Saponinas/isolamento & purificação , Espirostanos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Índia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Saponinas/química , Saponinas/farmacologia , Espirostanos/química , Espirostanos/farmacologiaRESUMO
Two new oleanane-type saponins, coriariosides A (1) and B (2), along with a known saponin, gummiferaoside C (3), were isolated from the roots of Albizia coriaria. Their structures were established by extensive analysis of 1D and 2D NMR experiments (COSY, ROESY, TOCSY, HSQC, and HMBC) and mass spectrometry. Compounds 1 and 3 when tested for cytotoxicity against two colorectal human cancer cells showed activity against the HCT 116 (IC50 4.2 microM for 1 and 2.7 microM for 3) and HT-29 (IC50 6.7 microM for 1 and 7.9 microM for 3) cell lines.
Assuntos
Albizzia/química , Antineoplásicos Fitogênicos , Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Saponinas , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Camarões , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Células HT29 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Raízes de Plantas/química , Saponinas/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
Oncolytic immunotherapies represent a new promising strategy in the treatment of cancer. In our efforts to develop oncolytic peptides, we identified a series of chemically modified 9-mer cationic peptides that were highly effective against both drug-resistant and drug-sensitive cancer cells and with lower toxicity toward normal cells. Among these peptides, LTX-315 displayed superior anticancer activity and was selected as a lead candidate. This peptide showed relative high plasma protein binding abilities and a human plasma half-life of 160 min, resulting in formation of nontoxic metabolites. In addition, the lead candidate demonstrated relatively low ability to inhibit CYP450 enzymes. Collectively these data indicated that this peptide has potential to be developed as a new anticancer agent for intratumoral administration and is currently being evaluated in a phase I/IIa study.
Assuntos
Antineoplásicos/farmacologia , Oligopeptídeos/sangue , Oligopeptídeos/farmacologia , Animais , Antineoplásicos/sangue , Proteínas Sanguíneas , Linhagem Celular Tumoral/efeitos dos fármacos , Inibidores das Enzimas do Citocromo P-450/farmacologia , Cães , Descoberta de Drogas , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Estabilidade de Medicamentos , Meia-Vida , Humanos , Camundongos Endogâmicos BALB C , Peptídeos/química , Peptídeos/farmacologia , RatosRESUMO
Three new steroidal saponins, named diospreussinosides A-C (1-3), along with two known ones (4, 5) were isolated from rhizomes of Dioscorea preussii. Their structures were elucidated mainly by 1D and 2D NMR spectroscopic analysis and mass spectrometry as (25S)-17α,25-dihydroxyspirost-5-en-3ß-yl-O-α-L-rhamnopyranosyl-(1â4)-α-L-rhamnopyranosyl-(1â4)-ß-D-glucopyranoside (1), (25S)-17α,25-dihydroxyspirost-5-en-3ß-yl-O-α-L-rhamnopyranosyl-(1â4)-α-L-rhamnopyranosyl-(1â4)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (2), and (24S,25R)-17α,24,25-trihydroxyspirost-5-en-3ß-yl-O-α-L-rhamnopyranosyl-(1â4)-α-L-rhamnopyranosyl-(1â4)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (3). The spirostane-type skeleton of compound 3 possessing an unusual dihydroxylation pattern on the F-ring is reported for the first time. Cytotoxicity of compounds 2-5 was evaluated against two human colon carcinoma cell lines (HT-29 and HCT 116).
Assuntos
Dioscorea/química , Fitosteróis/isolamento & purificação , Saponinas/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Células HT29 , Humanos , Estrutura Molecular , Fitosteróis/química , Saponinas/químicaRESUMO
A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of four spirostane-type glycosides (1-4), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25S)-spirost-5-en-3ß,12ß,21-triol 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (1), (20S,25S)-spirost-5-en-3ß,11α,21-triol 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (2), laxogenin 3-O-α-L-rhamnopyranosyl-(1â2)-[ß-D-glucopyranosyl-(1â4)]-ß-D-glucopyranoside (3), and (25R)-5α-spirostan-3ß,11α-diol 3-O-ß-D-glucopyranosyl-(1â3)-[ß-D-glucopyranosyl-(1â4)]-ß-D-galactopyranoside (4). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.
Assuntos
Cebolinha-Francesa/química , Glicosídeos/química , Glicosídeos/toxicidade , Estruturas Vegetais/química , Sobrevivência Celular/efeitos dos fármacos , Neoplasias do Colo/tratamento farmacológico , Glicosídeos/farmacologia , Células HCT116 , Células HT29 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Saponinas/química , Saponinas/farmacologiaRESUMO
Phytochemical investigation of the under-ground parts of Hydrocotyle bonariensis led to the isolation of five oleanane-type triterpenoid saponins, 3-O-{ß-D-glucopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl}-21-O-(2-methylbutyroyl)-22-O-acetyl-R(1)-barrigenol, 3-O-{ß-D-glucopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl}-21-O-(2-methylbutyroyl)-28-O-acetyl-R(1)-barrigenol, 3-O-{ß-D-glucopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl}-21-O-acetyl-R(1)-barrigenol, 3-O-{ß-D-glucopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl}-R(1)-barrigenol, and 3-O-{ß-D-glucopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl}-22-O-(2-methylbutyroyl)-A(1)-barrigenol, together with the known saniculoside-R1. Their structures were established by 2D NMR techniques and mass spectrometry. Six compounds were evaluated against two human colon cancer cell lines, HCT 116 and HT-29. Two compounds showed weak cytotoxicity with IC(50) 24.1 and 24.0, 83.0 and 83.6 µM against HT-29 and HCT 116, respectively.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Apiaceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Camarões , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Células HT29 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Rizoma/química , Saponinas/química , Saponinas/farmacologia , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacologiaRESUMO
A new spirostanol saponin (1), along with four known saponins, dioscin (2), protodioscin (3), methyl-protodioscin (4), and indioside D (5), and one known steroid glycoalkaloid solamargine (6) were isolated from the two synonymous species, Solanum incanum and S. heteracanthum. The structure of the new saponin was established as (23S,25R)-spirost-5-en-3ß,23-diol 3-O-{ß-D-xylopyranosyl-(1â2)-O-α-L-rhamnopyranosyl-(1â4)-[O-α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside}, by using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, NOESY, HSQC and HMBC experiments and by mass spectrometry. The compounds 1, 3, 4 and 5 were evaluated for cytotoxicity against five cancer cell lines and for antioxidant and cytoprotective activity.
Assuntos
Antioxidantes/farmacologia , Diosgenina/análogos & derivados , Glicosídeos/farmacologia , Neoplasias/tratamento farmacológico , Extratos Vegetais/farmacologia , Saponinas/farmacologia , Solanum/química , Espirostanos/farmacologia , Esteroides/farmacologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Antioxidantes/isolamento & purificação , Antioxidantes/uso terapêutico , Linhagem Celular Tumoral , Diosgenina/isolamento & purificação , Diosgenina/farmacologia , Diosgenina/uso terapêutico , Glicosídeos/isolamento & purificação , Glicosídeos/uso terapêutico , Humanos , Camundongos , Estrutura Molecular , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Saponinas/química , Saponinas/isolamento & purificação , Saponinas/uso terapêutico , Alcaloides de Solanáceas/química , Alcaloides de Solanáceas/isolamento & purificação , Solanum/classificação , Especificidade da Espécie , Espirostanos/química , Espirostanos/isolamento & purificação , Esteroides/isolamento & purificação , Esteroides/uso terapêuticoRESUMO
The synthesis of the adamantane phenylalkylamines 2a-d, 3a-c, and 4a-e is described. These compounds exhibited significant antiproliferative activity, in vitro, against eight cancer cell lines tested. The σ(1), σ(2), and sodium channel binding affinities of compounds 2a, 3a, 4a, and 4c-e were investigated. The most interesting analogue, 4a, exhibited significant in vivo anticancer profile on pancreas, prostate, leukemia, and ovarian cancer cell line xenografts together with apoptosis and caspase-3 activation. Inhibition of the cancer cells cycle at the sub-G1 level was also obtained with 4a. Finally, encouraging results were observed with 4a in vivo on mice, suggesting putative antimetastatic and analgesic activities of this compound.
Assuntos
Adamantano/análogos & derivados , Adamantano/química , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Neuralgia/tratamento farmacológico , Piperidinas/farmacologia , Receptores sigma/metabolismo , Adamantano/síntese química , Adamantano/farmacologia , Animais , Antineoplásicos/síntese química , Caspase 3/metabolismo , Ciclo Celular/efeitos dos fármacos , Feminino , Humanos , Masculino , Camundongos , Camundongos SCID , Estrutura Molecular , Neoplasias Ovarianas/tratamento farmacológico , Neoplasias Ovarianas/metabolismo , Neoplasias Pancreáticas/tratamento farmacológico , Neoplasias Pancreáticas/metabolismo , Piperidinas/síntese química , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/metabolismo , Ligação Proteica , Relação Estrutura-Atividade , Células Tumorais CultivadasRESUMO
Three oleanane-type saponins, 3-O-ß-d-glucopyranosylechinocystic acid 28-O-ß-d-xylopyranosyl-(1â4)-[α-l-rhamnopyranosyl-(1â2)]-α-l-rhamnopyranosyl ester (1), 3-O-ß-d-glucopyranosylechinocystic acid 28-O-α-l-arabinopyranosyl-(1â3)-ß-d-xylopyranosyl-(1â4)-[α-l-rhamnopyranosyl-(1â2)]-α-l-rhamnopyranosyl ester (2), 3-O-ß-d-glucopyranosylcaulophyllogenin 28-O-ß-d-apiofuranosyl-(1â3)-ß-d-xylopyranosyl-(1â4)-[ß-d-apiofuranosyl-(1â3)]-α-l-rhamnopyranosyl-(1â2)-α-l-rhamnopyranosyl ester (3) were isolated from the whole plant of Arenaria montana. Their unusual structures for the Caryophyllaceae family were established mainly by 2D NMR techniques and mass spectrometry.
Assuntos
Antineoplásicos/química , Arenaria/química , Ácido Oleanólico/análogos & derivados , Saponinas/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , EstereoisomerismoRESUMO
A new triterpene saponin 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-arabinopyranosyl-16alpha-hydroxy-13beta,28-epoxy-oleanan-30-al (1), along with four known triterpene glycosides (2-5) were isolated from Cyclamen persicum. Their structures were characterized by a combination of 1D- and 2D-NMR (1H-1H COSY, TOCSY, NOESY, HSQC, and HMBC) and MS spectrocopic data. The cytotoxicity of compounds 2 and 4 was evaluated using two human colon cancer cell lines HT-29 and HCT 116.
Assuntos
Cyclamen/química , Saponinas/química , Saponinas/toxicidade , Triterpenos/química , Linhagem Celular Tumoral , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Four triterpene saponins, 3-O-beta-D-glucopyranosylpresenegenin 28-O-beta-D-apiofuranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-{4-O-[(E)-3,4,5-trimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-[(6-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]-{4-O-[(E)-3,4,5-trimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin 28-O-beta-D-apiofuranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-{4-O-[(E)-3,4,5-trimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin 28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-L-arabinopyranosyl-(1-->4)]-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-{4-O-[(E)-3,4,5-trimethoxycinnamoyl]}-beta-D-fucopyranosyl ester, were isolated from the roots of Securidaca longepedunculata, together with three known compounds. Their structures were established mainly by 2D NMR techniques and mass spectrometry.