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1.
Fitoterapia ; 144: 104596, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32333960

RESUMO

Seven oleanane-type triterpenoid saponins, tunicosaponins B-D (1-3), F-I (4-7), along with eight known triterpenoid saponins (8-15), were isolated from the roots of Psammosilene tunicoides. The structures of compounds 1-7 were determined by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Triterpene glycosides have been considered as major active constituents of P. tunicoides. This work provides a more complete insight into the saponin constituents of P. tunicoides.

2.
Org Lett ; 20(23): 7567-7570, 2018 12 07.
Artigo em Inglês | MEDLINE | ID: mdl-30421929

RESUMO

Vlasoulamine A (1), an unprecedented sesquiterpene lactone dimer featuring a fully hydrogenated pyrrolo[2,1,5- cd]indolizine core, and vlasoulones A and B (2 and 3), a pair of epimeric dimers formed from a proposed Diels-Alder [4 + 2] cycloaddition between a germacrane sesquiterpene lactone and a eudesmane sesquiterpene, were isolated from the roots of Vladimiria souliei. Their structures and absolute configurations were established by NMR, MS, and single-crystal X-ray spectroscopic analysis. Moreover, 1 exhibited neuroprotective activity when evaluated for glutamate-induced cytotoxicity, nuclear Hoechst 33258 staining, and measuring intracellular reactive oxygen species levels, using a rat pheochromocytoma PC12 cell-based model system.


Assuntos
Antineoplásicos/farmacologia , Asteraceae/química , Lactonas/farmacologia , Fármacos Neuroprotetores/farmacologia , Raízes de Plantas/química , Sesquiterpenos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Ácido Glutâmico/farmacologia , Lactonas/química , Lactonas/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Células PC12 , Ratos , Espécies Reativas de Oxigênio/análise , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
3.
Zhongguo Zhong Yao Za Zhi ; 43(1): 100-108, 2018 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-29552818

RESUMO

Application of a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, led to the isolation of 173 compounds including irdidoids, monoterpenes, sesquiterpenes, triterpenes, lignans, flavonoids, and simple aromatic derivatives from the ethyl acetate-soluble fraction of the whole plants of Valeriana jatamansi(Valerianaceae), and their structures were elucidated by spectroscopic methods including 1D, 2D NMR UV, IR, and MS techniques. Among them, 77 compounds were new. In previous reports, we have described the isolation, structure elucidation, and bioactivities of 68 new and 25 known compounds. As a consequence, we herein reported the isolation and structure elucidation of the remaining 9 new and 71 known compounds, the structure revision of valeriotriate A(8a), as well as cytotoxicity of some compounds.


Assuntos
Extratos Vegetais/química , Valeriana/química , Acetatos , Cromatografia Líquida de Alta Pressão , Flavonoides/análise , Iridoides/análise , Lignanas/análise , Estrutura Molecular , Monoterpenos/análise , Compostos Fitoquímicos/análise , Sesquiterpenos/análise , Triterpenos/análise
4.
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
5.
Phytochemistry ; 139: 47-55, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28411482

RESUMO

Six previously undescribed C17-guaianolides, a previously undescribed guaianolide alkaloid, and two previously undescribed guaianolides as well as 10 known guaianolides were obtained from an ethanol extract of Ainsliaea yunnanensis Franch. The chemical structures of all previously reported sesquiterpenoids were determined by extensive NMR spectroscopic analysis in combination with a modified Mosher's method. All isolates were in vitro screened for inhibitory effect against nitric oxide release in RAW 264.7 macrophages stimulated by LPS. Zaluzanin C remarkably inhibited the production of nitric oxide with an IC50 value of 6.54 µM.


Assuntos
Alcaloides/isolamento & purificação , Asteraceae/química , Sesquiterpenos de Guaiano/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Animais , Sobrevivência Celular/efeitos dos fármacos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/farmacologia
6.
J Ethnopharmacol ; 196: 39-46, 2017 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-27988396

RESUMO

BACKGROUNDS: Inula helenium L. is an herb with anti-inflammatory properties. Sesquiterpene lactones (SLs), mainly alantolactone (AL) and isoalantolactone (IAL), are considered as its active ingredients. However, the anti-inflammatory effects of SL-containing extracts of I. helenium have not been explored. Here we prepared total SLs from I. helenium (TSL-IHL), analyzed its chemical constituents, and performed cellular and animal studies to evaluate its anti-inflammatory activities. MATERIALS AND METHODS: The chemical profile of TSL-IHL was analyzed by HPLC-UV. Its in vitro effects on the activation of signaling pathways and expression of inflammatory genes were examined by western blotting and quantitative real-time PCR, respectively, and compared with those of AL and IAL. Its in vivo anti-inflammatory effects were evaluated in adjuvant- and collagen-induced arthritis rat models. RESULTS: Chemical analysis showed that AL and IAL represent major constituents of TSL-IHL. TSL-IHL, as well as AL and IAL, could inhibit TNF-α-induced activation of NF-κB and MAPK pathways in b. End3 cells, suppress the expressions of MMP-3, MCP-1, and IL-1 in TNF-α-stimulated synovial fibroblasts, and IL-1, IL-6, and iNOS in LPS-activated RAW 264.7 cells in a dose-dependent manner in the range of 0.6-2.4µg/mL. Oral administration of TSL-IHL at 12.5-50mg/kg could dose-dependently alleviate the arthritic severity and paw swelling in either developing or developed phases of arthritis of rats induced by adjuvant or collagen CONCLUSIONS: These results indicated potentials of TSL-IHL in prevention and therapy of rheumatoid arthritis.


Assuntos
Anti-Inflamatórios/uso terapêutico , Artrite Experimental/tratamento farmacológico , Artrite Reumatoide/tratamento farmacológico , Inula , Lactonas/uso terapêutico , Sesquiterpenos/uso terapêutico , Animais , Anti-Inflamatórios/farmacologia , Artrite Experimental/metabolismo , Artrite Experimental/prevenção & controle , Artrite Reumatoide/metabolismo , Artrite Reumatoide/prevenção & controle , Linhagem Celular , Citocinas/genética , Citocinas/metabolismo , Lactonas/farmacologia , Masculino , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Raízes de Plantas , Células RAW 264.7 , Ratos Wistar , Sesquiterpenos/farmacologia
7.
Fitoterapia ; 113: 110-6, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27476617

RESUMO

Two new flavan derivatives tazettones C-D (1-2), one new ß-coumaranone (tazettone E, 3), one new flavan (tazettone F, 4), and one new phenylpropanoid (tazettone G, 5), together with six known flavonoids (6-11), were isolated from the bulbs of Narcissus tazetta var. chinensis Roem. Their structures were elucidated by spectroscopic analysis. In addition, the structures of 1-3 were confirmed by single crystal X-ray diffraction. All isolated compounds were tested for antioxidant activity by Cell Counting Kit-8 (CCK-8) assay. Compounds 6-8 and 10-11 exhibited potent antioxidant activity against H2O2-induced impairment in human SH-SY5Y neuroblastoma cells at tested concentrations.


Assuntos
Antioxidantes/química , Flavanonas/química , Narcissus/química , Raízes de Plantas/química , Antioxidantes/isolamento & purificação , Linhagem Celular Tumoral , Flavanonas/isolamento & purificação , Humanos , Peróxido de Hidrogênio , Estrutura Molecular
8.
J Chromatogr Sci ; 54(6): 1041-9, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27068933

RESUMO

The qualitative and quantitative analysis of the major bioactive components in traditional Chinese medicines (TCM) and their preparations is essential to evaluate their quality. However, the scarcity and high cost of chemical reference standards are common obstacles for quantitative analysis, especially for determining multicomponents. In this study, an effective and sensitive qualitative method to identify flavonol glycosides in Ginkgo leaves (Ginkgo Folium), and their preparations have been developed. Meanwhile, a simple, convenient and reproducible method for the quantitative analysis of multicomponents by a single marker (QAMS) has been established to simultaneously determine the major flavonol glycosides in Ginkgo leaves and their preparations. Among the 15 favonol glycosides that were found, 7 major flavonol glycosides with high contents were simultaneously determined by the QAMS and traditional external standard method (TES). Rutin was selected as the single marker, and the quantitative analysis was performed on a TSK gel ODS-100V C18 column using a gradient system of acetonitrile and water, with a variable wavelength detector (265 nm) within 50 min. The method validation was conducted, and the linearity was excellent (r(2) > 0.9993) with accuracy and precision within the required limits. The F-test (P> 0.05) indicated that the QAMS and TES method have no statistically significant difference.


Assuntos
Técnicas de Química Analítica/métodos , Medicamentos de Ervas Chinesas/química , Ginkgo biloba/química , Glicosídeos/análise , Folhas de Planta/química , Cromatografia Líquida de Alta Pressão , Reprodutibilidade dos Testes
9.
Fitoterapia ; 110: 72-6, 2016 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-26940575

RESUMO

Three new sesquiterpene lactone dimers (SLDs), carpedilactones E-G (1-3), together with two known monomeric units, ivalin (4) and alantolactone (5), were isolated from the acetonic extract of Carpesium macrocephalum. Their chemical structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments, and the absolute configuration of 1-3 was resolved according to the (1)H NMR and CD spectrographic features of 1,3-/2,4-linked SLDs. Furthermore, 1 was unambiguously confirmed by Cu-Kα X-ray crystallographic analysis. Additionally, compounds 1 and 2 were revealed with potent cytotoxicities against human colon cancer HCT116 cells with IC50 values of 2.27 and 3.30 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/química , Asteraceae/química , Lactonas/química , Sesquiterpenos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Lactonas/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação
10.
J Asian Nat Prod Res ; 17(5): 455-61, 2015 May.
Artigo em Inglês | MEDLINE | ID: mdl-25971678

RESUMO

Three new decomposition products of valepotriates, valtrals A-C (1-3), and two known products, baldrinal and homobaldrinal, are formed during the isolation procedure of the ethanol extract of the whole plants of Valeriana jatamansi. Their structures were determined by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-3 showed selective cytotoxicity against metastatic prostate cancer (PC-3M) and colon cancer (HCT-8) cell lines.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Iridoides/isolamento & purificação , Iridoides/farmacologia , Valeriana/química , Antineoplásicos Fitogênicos/química , Neoplasias do Colo/tratamento farmacológico , Medicamentos de Ervas Chinesas/química , Humanos , Iridoides/química , Masculino , Estrutura Molecular , Nardostachys , Ressonância Magnética Nuclear Biomolecular , Neoplasias da Próstata/tratamento farmacológico
11.
Phytochemistry ; 116: 221-229, 2015 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-25986863

RESUMO

Nine lanostane-type triterpenoids were isolated from branches and leaves of Abies faxoniana, along with 10 known compounds. Two were isolated as inseparable mixtures of epimers at C-23 of the γ-lactone ring that had a lactol structure. The structures of the nine compounds were established by spectroscopic analysis and circular dichroism (CD) data. The absolute configurations at the stereogenic centres of two of the known compounds were confirmed by X-ray crystallography. One compound showed cytotoxic activities against HCT-116, MCF-7, and A549 cells with IC50 values of 8.9, 7.6, and 4.2µM, respectively. The isolated compounds were tested for their effects on human DNA topoisomerases I and II. One was found to be a selective inhibitor of human topo II activity with an IC50 value of 53.5µM, which was comparable to that of the topo II inhibitor etoposide (IC50=49.6µM).


Assuntos
Abies/química , DNA Topoisomerases/efeitos dos fármacos , Lanosterol/isolamento & purificação , Lanosterol/farmacologia , Inibidores da Topoisomerase II/isolamento & purificação , Inibidores da Topoisomerase II/farmacologia , Inibidores da Topoisomerase/isolamento & purificação , Inibidores da Topoisomerase/farmacologia , Cristalografia por Raios X , Humanos , Concentração Inibidora 50 , Lanosterol/química , Estrutura Molecular , Componentes Aéreos da Planta/química , Estereoisomerismo , Inibidores da Topoisomerase II/química , Inibidores da Topoisomerase/química
13.
Org Lett ; 16(16): 4216-9, 2014 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-25079622

RESUMO

Four new isomeric sesquiterpene lactone dimers, carpedilactones A-D (1-4), were isolated from the acetonic extract of Carpesium faberi. Among them, 1-3 are the first three 2,4-linked exo-Diels-Alder adducts between a eudesmanolide dienophile and a guaianolide diene. The absolute configurations of 1-4 were unambiguously established by Cu Kα X-ray crystallographic analyses. Compounds 1-4 exhibited potent cytotoxicities against human leukemia (CCRF-CEM) cells with IC50 value of 0.14, 0.32, 0.35, and 0.16 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Conformação Molecular , Estrutura Molecular , Sesquiterpenos/química
14.
Phytochemistry ; 106: 116-123, 2014 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-25081106

RESUMO

During a survey on chemical constituents of Abies nukiangensis, seven previously unreported compounds, including six triterpenes (1-6) and one phenol (7) were isolated and characterized, together with 37 known miscellaneous chemical constituents. The structures of compounds 1-7 were established mainly by extensive analysis of the 1D and 2D NMR, as well as HRMS data. The absolute configurations of compounds 1 and 8 were confirmed unambiguously by the Cu-Kα X-ray crystallography. Compounds 3 and 8-10 showed significant anti-hepatitis C virus effects with EC50 values of 3.73, 2.67, 1.33 and 2.25µM, respectively.


Assuntos
Abies/química , Antivirais/química , Fenóis/química , Triterpenos/química , Antivirais/isolamento & purificação , Linhagem Celular Tumoral , Hepacivirus/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fenóis/isolamento & purificação , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Triterpenos/isolamento & purificação
15.
Phytochemistry ; 105: 135-40, 2014 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24952469

RESUMO

γ-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-Kα X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8µg/mL, respectively.


Assuntos
Antibacterianos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Furanos/isolamento & purificação , Glucosídeos/isolamento & purificação , Nitrilos/isolamento & purificação , Rosaceae/química , Sementes/química , Antibacterianos/química , Antibacterianos/farmacologia , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Furanos/química , Furanos/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Testes de Sensibilidade Microbiana , Conformação Molecular , Estrutura Molecular , Nitrilos/química , Ressonância Magnética Nuclear Biomolecular , Salmonella/efeitos dos fármacos , Estereoisomerismo , Vibrio/efeitos dos fármacos
16.
J Asian Nat Prod Res ; 16(7): 724-9, 2014.
Artigo em Inglês | MEDLINE | ID: mdl-24665870

RESUMO

Two new lignans, 9-salicyl-(+)-isolariciresinol (1) and gaultheroside G (2), together with seven known compounds, were isolated from the ethanolic extract of the whole plant of Gaultheria yunnanensis. Their structures were determined by extensive NMR and MS analyses. Gaultheroside G (2) was found to have an unusual ether linkage between the 2 and 9' positions of aryl-tetralin lignan skeleton. All nine compounds were assayed for inhibitory effects against nitric oxide and pro-inflammatory cytokines TNF-α and IL-6 release in LPS-induced RAW 246.7 macrophages, while no significant activities were observed for the evaluated compounds.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Gaultheria/química , Lignanas/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Interleucina-6/antagonistas & inibidores , Interleucina-6/farmacologia , Lignanas/química , Lignanas/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Precursores de Proteínas , Fator de Necrose Tumoral alfa/efeitos dos fármacos
17.
Arch Pharm Res ; 37(11): 1411-5, 2014 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-24293062

RESUMO

Three new diphenylpropanes, Hindsiipropane A-C (1-3), together with one known arylpropyl quinone Griffithane D (4), were isolated from Celastrus hindsii. Their structures were established by 1D and 2D nuclear magnetic resonance spectroscopic analysis, and mass spectroscopy. Compound 4 was firstly obtained in this genus. All the isolated compounds were evaluated in vitro for cytotoxicity against four human tumor cell lines (A549, HCT116, MDA-MB-231, BEL7404) by the MTT assay.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Compostos de Bifenilo/isolamento & purificação , Celastrus/química , Antineoplásicos Fitogênicos/farmacologia , Compostos de Bifenilo/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Caules de Planta/química , Espectrometria de Massas por Ionização por Electrospray , Espectroscopia de Infravermelho com Transformada de Fourier
18.
Phytochemistry ; 85: 185-93, 2013 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-23036722

RESUMO

HPLC-PDA-MS and TLC analysis were used to look for minor cytotoxic chlorinated valepotriates from whole plants of Valeriana jatamansi (syn. Valeriana wallichii DC.). This resulted in isolation of 15 chlorinated valepotriates, designated as chlorovaltrates A-O, together with six known analogues, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1,5-dihydroxyvalechlorine, volvaltrate B, chlorovaltrate, rupesin B, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5-hydroxyvalechlorine, and (1R,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5-hydroxyvalechlorine. Their structures were elucidated by spectroscopic methods including homo- and heteronuclear two-dimensional NMR experiments. Chlorovaltrates K-N, chlorovaltrate and rupesin B showed moderate cytotoxicity against lung adenocarcinoma (A 549), metastatic prostate cancer (PC-3M), colon cancer (HCT-8) and hepatoma (Bel 7402) cell lines with IC50 values of 0.89-9.76 µM.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Iridoides/química , Iridoides/farmacologia , Valeriana/química , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
19.
Arch Pharm Res ; 34(10): 1587-91, 2011 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-22076757

RESUMO

A new furostanol saponin, (25S)-26-O-ß-D-glucopyranosyl-5ß-furost-20(22)-en-3ß, 15ß,26-triol-3-O-[α-L-rhamnopyranosyl-(1-4)]-ß-D: -glucopyranoside, namely, aspacochioside D (1) were isolated from Asparagus cochinchinensis (Lour.) Merr, along with three known saponins, aspacochioside C (2), (25S)-5ß-spirostan-3ß-yl-O-[O-α-L-rhamnopyranosyl-(1-4)]-ß-D-glucopyranoside (3), and pseudoprotoneodioscin (4). The structure of 1 was elucidated on the basis of chemical reactions and spectral analysis (IR, GC, ESI-MS, (1)H-NMR, (13)C-NMR, DEPT, HMBC, HMQC and NOESY). The antiproliferative effects of 1-4 were evaluated in a cytotoxicity assay against the human tumor cell line, A549. Compound 2 (Aspacochioside C) exhibited moderate cytotoxicity against A-549, with an IC(50) value of 3.87 µg/mL.


Assuntos
Antineoplásicos Fitogênicos/química , Asparagus (Planta)/química , Saponinas/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Cromatografia Gasosa , Corantes , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidrólise , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho , Esteroides/química , Esteroides/isolamento & purificação , Esteroides/farmacologia , Sais de Tetrazólio , Tiazóis
20.
Planta Med ; 77(13): 1545-50, 2011 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-21412699

RESUMO

Investigation of the ethanol extract of the whole plant of Ainsliaea macrocephala led to the isolation of five new sesquiterpenoids, namely ainsliadimer C (1), ainsliadimer D (2), ainsliaolide B (3), ainsliatone B (4), and ainsliaolide C (5), together with seventeen known sesquiterpenes and sesquiterpene glycosides (6- 22). Their structures were elucidated by spectroscopic methods. The relative stereochemistry of ainsliadimers C (1) and D (2) were further confirmed by single crystal X-ray diffraction analysis. Total extract of A. macrocephala and compounds 1- 22 were tested for inhibitory activity against the production of nitric oxide in RAW 264.7 cells stimulated by LPS, as well as for cytotoxicity against RAW 264.7 macrophages. Of all samples tested, purified compounds 4, 7, and 12 strongly inhibited the production of nitric oxide with IC50 values of 8.78, 2.50, and 7.11 µM, and simultaneously showed low cytotoxicity against RAW 264.7 macrophages.


Assuntos
Asteraceae/química , Glicosídeos/farmacologia , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Sesquiterpenos/farmacologia , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Glicosídeos/química , Glicosídeos/isolamento & purificação , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Difração de Raios X
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