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1.
Nat Prod Bioprospect ; 2020 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-32415420

RESUMO

Betulin (BE) has exceedingly become a potential natural product, providing multiple pharmacological and biological activities, including anti-cancer, anti-viral, and anti-inflammatory benefits. Previous research indicated that the solvatomorphism of BE can easily occur through crystallization with different organic solvents. This property of BE can directly affect its extraction, isolation, and preparation process. In this study, a system of thermogravimetry (TG)-differential thermal analysis (DTA) coupled with mass spectrometry (MS) with electron ionization (EI) and photoionization (PI) capability, equipped with the skimmer-type interface (i.e., skimmer-type interfaced TG-DTA-EI/PI-MS system), as a real-time and onsite analysis technique, was employed. Then, four solvatomorphs of BE, namely, with pyridine and water (A), sec-butanol (B), n,n-dimethylformamide (DMF) (C), and isopropanol (V), were analyzed for the first time. Finally, five kinds of the main volatile gaseous species, including H2O, pyridine, sec-butanol, DMF, and isopropanol, were identified clearly. Furthermore, the multi-step desolvation processes of the four solvatomorphs of BE were revealed by this system for the first time. This system showed great potential for the rapid and accurate analysis of various solvatomorphs of natural products.

2.
R Soc Open Sci ; 6(1): 181905, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30800407

RESUMO

Sophoricoside, which is an isoflavone glycoside found in many plant species, has recently attracted attention because of its anti-fertility activity. One solvent-free form, two solvatomorphs and an amorphous phase of sophoricoside are reported for the first time. X-ray diffractometry, differential scanning calorimetry, thermal gravimetric analysis and Fourier-transform infrared spectroscopy were used to characterize the different forms. The results show that factors such as crystal symmetry, intermolecular arrangement, conformational flexibility, hydrogen-bonding interactions and solvent incorporation lead to different solid-state forms. An investigation of the transformations of the four forms showed that they can interconvert with each other under certain conditions. Amorphous phase and solvatomorphism were unstable but can improve the solubility of sophoricoside in water.

3.
Fitoterapia ; 101: 194-200, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-25647326

RESUMO

A new linear pyranocoumarin named (-)-hydroxydecursinol (1) and a new biscoumarin named (±)-dahuribiscoumarin (2), together with six known compounds isoimperatorin (3), imperatorin (4), phellopterin (5), isodemethylfuropinarine (6), demethylfuropinarine (7), and (+)-decursinol (8) were isolated from the 75% ethanolic extract of the roots of Angelica dahurica var. formosana cv. Chuanbaizhi. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry, and the structure of 2 was confirmed by single-crystal X-ray diffraction. All of the isolated compounds were evaluated for the inhibition against nitric oxide (NO) production in the lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell line, and exhibited the inhibitory activity on NO production in a concentration-dependent manner. Furthermore, real-time PCR analysis revealed that compounds 2, 5-8 could significantly suppress the expression levels of inducible nitric oxide synthase mRNA in a concentration-dependent manner. And their primary structure-activity relationships of NO inhibitory effects were also briefly discussed. These compounds are potential candidates for further bioassay studies to determine their suitability as drug leads.


Assuntos
Angelica/química , Cumarínicos/química , Macrófagos/efeitos dos fármacos , Óxido Nítrico/metabolismo , Animais , Linhagem Celular , Cumarínicos/isolamento & purificação , Lipopolissacarídeos , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/metabolismo , Raízes de Plantas/química , Relação Estrutura-Atividade
4.
Org Lett ; 15(17): 4450-3, 2013 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-23937631

RESUMO

Two novel spirooliganones A (1) and (2), a pair of spiro carbon epimers, with a rare dioxaspiro skeleton were isolated from the roots of Illicium oligandrum. The structures were fully determined by spectroscopic analysis and chemical methods, especially modified Mosher's method, and X-ray diffraction analysis. Spirooliganone B was found to exhibit more potent activities against coxsackie virus B3 and influenza virus A (H3N2) (IC50 3.70-5.05 µM) than spirooliganone A. The biosynthetic pathway involving a hetero-Diels-Alder reaction of the epimers was proposed.


Assuntos
Antivirais/isolamento & purificação , Antivirais/farmacologia , Illicium/química , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia , Antivirais/química , Reação de Cicloadição , Enterovirus Humano B/efeitos dos fármacos , Vírus da Influenza A Subtipo H3N2/efeitos dos fármacos , Estrutura Molecular , Raízes de Plantas/química , Compostos de Espiro/química , Estereoisomerismo
5.
Org Lett ; 15(17): 4446-9, 2013 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-23944990

RESUMO

Scopariusic acid (1), a new ent-clerodane-based meroditerpenoid with a unique cyclobutane ring and an unusual 1-octen-3-ol substituent, together with its biosynthetic related compound 2, were isolated from the aerial parts of Isodon scoparius. The structures of 1 and 2, including their absolute configurations, were determined by spectroscopic methods, single-crystal X-ray diffraction analysis, and chemical methods. Compound 1 showed weak cytotoxicity and moderate immunosuppressive activity.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos de Caurano/química , Diterpenos de Caurano/isolamento & purificação , Imunossupressores/química , Imunossupressores/isolamento & purificação , Isodon/química , Antineoplásicos Fitogênicos/farmacologia , Cristalografia por Raios X , Diterpenos de Caurano/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Células HL-60 , Humanos , Imunossupressores/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
6.
J Asian Nat Prod Res ; 15(10): 1130-8, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-23869424

RESUMO

A new limonoid compound, named evorubodinin (1), was isolated from the dried and nearly ripe fruits of Euodia rutaecarpa (Juss.) Benth. var. bodinieri (Dode) Huang (family Rutaceae), together with two known limonoid compounds, limonin (2) and evolimorutanin (3). The chemical structure of 1 was elucidated by spectroscopic method and single-crystal X-ray diffraction. The inhibitory effects of the isolated compounds 1-3 and the structurally related compounds evodol (4), shihulimonin A1 (5), evodirutaenin (6), 12α-hydroxyrutaevin (7), and rutaevin (8) on nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 macrophages were also assayed. All compounds 1-8 showed the inhibitory activity, in which both 7 and 8 with the uncommon 5ß-H configuration more efficiently inhibited NO production. The results provided valuable information for further investigation of compounds 1-8 as anti-inflammatory agents or lead compounds.


Assuntos
Evodia/química , Limoninas/isolamento & purificação , Limoninas/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Óxido Nítrico/antagonistas & inibidores , Animais , Anti-Inflamatórios , Frutas/química , Limoninas/química , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Triterpenos/química
7.
Planta Med ; 79(12): 1063-7, 2013 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-23818269

RESUMO

Three new unusual 23-spirocholestane derivatives, ypsilanogenin (1), ypsilanogenin 3-O-ß-D-glucopyranoside (2), and 4'-acetylypsilanogenin 3-O-ß-D-glucopyranoside (3), were isolated from the whole plants of Ypsilandra thibetica. The structures of compounds 1-3 were deduced by spectroscopic and chemical methods, and the structure of 1 was further confirmed by a single-crystal diffraction analysis. All isolates were evaluated for their inhibitory activities against HIV-1.


Assuntos
Fármacos Anti-HIV/farmacologia , Glicosídeos/farmacologia , Liliaceae/química , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Colestanos/química , Colestanos/isolamento & purificação , Colestanos/farmacologia , Cristalografia por Raios X , Glicosídeos/química , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Plantas Medicinais , Saponinas/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Compostos de Espiro/farmacologia
8.
J Nat Prod ; 76(2): 216-22, 2013 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-23394318

RESUMO

Ten new abietane diterpenoids, aquilarabietic acids A-J (1-10), and a new podocarpane diterpenoid, aquilarabietic acid K (11), were isolated from the petroleum ether and ethanol extracts of Chinese eaglewood. Among them, 3, 9, and 10 are artifacts. Their structures were established on the basis of data from extensive spectroscopic and X-ray diffraction analyses. Bioassay results indicated that 1 at 10 µM demonstrated remarkable antidepressant activity in vitro by inhibiting norepinephrine reuptake in rat brain synaptosomes by 81.4% and with an IC(50) value of 9.1 × 10(-7) M.


Assuntos
Abietanos/isolamento & purificação , Abietanos/farmacologia , Antidepressivos/isolamento & purificação , Antidepressivos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Thymelaeaceae/química , Abietanos/química , Animais , Antidepressivos/química , Encéfalo/efeitos dos fármacos , Medicamentos de Ervas Chinesas/química , Masculino , Estrutura Molecular , Norepinefrina/antagonistas & inibidores , Ressonância Magnética Nuclear Biomolecular , Ratos , Sinaptossomos/efeitos dos fármacos
9.
Phytochemistry ; 88: 112-8, 2013 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-23312365

RESUMO

An 8,9-seco-lindenane disesquiterpenoid, chloramultiol G, four eudesmane sesquiterpenoids, ent-(3R)-3-hydroxyatractylenolide III and multistalactones A-C, and four guaiane sesquiterpenoids, (1R,4S,5R,8S,10S)-zedoalactone A and multistalactones D-F, along with 14 known compounds, were isolated from whole plant tissues of Chloranthus multistachys. Their structures were established by extensive NMR experiments in conjunction with mass spectrometry. Except for chloramultiol G, the absolute stereochemistries of the other eight were confirmed by single-crystal X-ray crystallography and CD spectra. Nine compounds were tested for cytotoxicity against five human tumor cell lines and for antifungal activity against four microorganisms in vitro, but all were inactive.


Assuntos
Magnoliopsida/química , Terpenos/química , Terpenos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , China , Cristalografia por Raios X , Humanos , Espectroscopia de Ressonância Magnética , Estruturas Vegetais/química
10.
J Nat Prod ; 74(6): 1408-13, 2011 Jun 24.
Artigo em Inglês | MEDLINE | ID: mdl-21650224

RESUMO

Five new lindenane disesquiterpenoids, chlorajaponilides A-E (1-5), together with 11 known analogues were isolated from whole plants of Chloranthus japonicus. The structure and absolute configuration of 1 was confirmed by X-ray crystallography. Compounds 1 and 2 represent the first examples of lindenane disesquiterpenoids with a C-5 hydroxy group and a C-4-C-15 double bond. Compounds 8, 9, 11, and 12 showed anti-HIV-1 replication activities in both wild-type HIV-1 and two NNRTIs-resistant strains. Shizukaol B (8) exhibited the best activity against HIV(wt), HIV(RT-K103N), and HIV(RT-K103N) with EC50 values of 0.22, 0.47, and 0.50 µM, respectively. Compounds 8, 9, 11, and 12 had significant cytotoxicities against C8166 cells with CC50 values of 0.020, 0.089, 0.047, and 0.022, respectively, and exhibited inhibitory activities against HIV-1 with EC50 values of 0.0014, 0.016, 0.0043, and 0.0033 µM, respectively.


Assuntos
Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , HIV-1/efeitos dos fármacos , Magnoliopsida/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Fármacos Anti-HIV/química , Cristalografia por Raios X , Humanos , Conformação Molecular , Estrutura Molecular , Sesquiterpenos/química , Relação Estrutura-Atividade
11.
Yao Xue Xue Bao ; 45(5): 673-6, 2010 May.
Artigo em Chinês | MEDLINE | ID: mdl-20931774

RESUMO

The powder X-ray diffraction Fourier fingerprint pattern technique was used to develop a new quantitation method for the analysis of andrographolide and dehydroandrographolide. And the high performance liquid chromatography method was used to evaluate the quantity of andrographolide and dehydroandrographolide. The relationship of diffraction peak intensity and content of andrographolide and dehydroandrographolide was investigated. The powder X-ray diffraction Fourier fingerprint pattern analysis technique can be used to evaluate the quantity of andrographolide and dehydroandrographolide in the herb simultaneously.


Assuntos
Andrographis/química , Diterpenos/análise , Plantas Medicinais/química , Difração de Raios X/métodos , Cromatografia Líquida de Alta Pressão , Medicamentos de Ervas Chinesas/análise , Análise de Fourier , Componentes Aéreos da Planta/química , Pós
12.
Chem Pharm Bull (Tokyo) ; 58(7): 939-43, 2010 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-20606341

RESUMO

Eighteen compounds, including three new triterpenoids, camellisins A-C (1-3), were isolated from the roots of Camellia sinensis. Their structures were determined on the basis of detailed spectroscopic analysis.


Assuntos
Camellia sinensis/química , Triterpenos/química , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Triterpenos/isolamento & purificação
13.
Fitoterapia ; 81(8): 988-91, 2010 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-20600690

RESUMO

Chiratone (1), a rare new chiratane type triterpenoid, together with five known triterpenoids were isolated from the rhizomes of Drynaria fortunei (Kunze) J. Sm. The structure was characterized as 20ß-hydroxychiratan-22-one on the basis of extensive 1D and 2D NMR, and MS spectroscopic analyses, and was further confirmed by X-ray crystal diffraction. Primary bioassays showed that compound 1 had significant cytotoxic activity against Hela, PC3 and HepG2 cells, with IC(50) of 2.92 µM, 1.08 µM and 2.45 µM, respectively.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Polypodiaceae/química , Rizoma/química , Triterpenos/química , Animais , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Neoplasias/tratamento farmacológico
14.
Acta Crystallogr Sect E Struct Rep Online ; 65(Pt 5): o987, 2009 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-21584025

RESUMO

The mol-ecule of the title compound, C(26)H(34)O(8), a prednisolone derivative, contains three six-membered rings (A, B and C) and one five-membered ring (D). Ring A is planar and rings B and C adopt chair conformations, while ring D adopts an envelope conformation with the C atom bonded to the methyl group at the flap. The crystal structure is stabilized by intermolecular O-H⋯O hydrogen bonds.

15.
Chem Pharm Bull (Tokyo) ; 55(9): 1287-90, 2007 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-17827749

RESUMO

Two new biflavonoids, daphnogirins A (1) and B (2), were obtained from the roots of Daphne giraldii. Their structures were established on the basis of the spectral data and X-ray diffraction data of the co-crystal of 1 and 2. Daphnogrins A and B have the same configuration at C-1 and opposite configurations at C-16 and C-17. Oxygen radical scavenging assay has indicated that they are of significant antioxidative activity.


Assuntos
Daphne/química , Flavonas/química , Antioxidantes/química , Cromanos/química , Cristalografia por Raios X , Fluoresceína/química , Depuradores de Radicais Livres/química , Espectroscopia de Ressonância Magnética , Conformação Molecular , Casca de Planta/química , Caules de Planta/química , Espécies Reativas de Oxigênio/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta
16.
Org Lett ; 8(5): 991-4, 2006 Mar 02.
Artigo em Inglês | MEDLINE | ID: mdl-16494492

RESUMO

Rubriflordilactones A (1) and B (2), two novel highly unsaturated rearranged bisnortriterpenoids possessing a biosynthetically modified aromatic D-ring, were isolated from the leaves and stems of Schisandra rubriflora. Their structures were established on the basis of extensive spectroscopic methods, including two-dimensional NMR techniques, and confirmed by X-ray crystallographic analysis. Compound 1 showed weak anti-HIV-1 activity, and compound 2 exhibited an EC50 value of 9.75 microg/mL (SI=12.39) against HIV-1 replication with low cytotoxicity.


Assuntos
Fármacos Anti-HIV/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , HIV-1/efeitos dos fármacos , Plantas Medicinais/química , Schisandra/química , Triterpenos/isolamento & purificação , Fármacos Anti-HIV/química , Fármacos Anti-HIV/farmacologia , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Triterpenos/química , Triterpenos/farmacologia , Células Tumorais Cultivadas
18.
Zhongguo Zhong Yao Za Zhi ; 28(3): 240-2, 2003 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-15015310

RESUMO

OBJECTIVE: To study the selective isolation of a single chemical component from volatile oil of Fructus foeniculi by inclucion method. METHOD: The host molecule was selected and a single chemical component isolated from volatile oil by the host-guest recognition. RESULT: X-ray single crystal analysis showed that 1,1,6,6-tetraphenylhexa-2, 4-diyne-1, 6-diol could successfully include 4-[1-propenyl] benzaldehyde from volatile oil of Fructus foeniculi. CONCLUSION: The host-guest inclusion technology can be used to isolate a single component selectively from mixture.


Assuntos
Foeniculum/química , Óleos Voláteis/química , Plantas Medicinais/química , Cristalização , Cristalografia por Raios X/métodos , Conformação Molecular , Óleos Voláteis/isolamento & purificação , Sementes/química
19.
J Nat Prod ; 65(2): 147-52, 2002 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-11858746

RESUMO

Seven new cycloartane glycosides (1-7), beesiosides G, H, and J-N, together with beesioside I (8) and beesioside A, were isolated from the rhizomes of Beesia calthifolia, and their structures were established by spectroscopic and chemical methods. Beesiosides G, H, and J-N were assigned as 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-beta-D-glucopyranoside (1), 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), (20S,24R)-15alpha,16beta-diacetoxy-20,24-epoxy-9,19-cyclolanostane-3beta,18,25-triol-3-O-beta-D-xylopyranoside (3), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,15beta,25-triol-3-O-beta-D-xylopyranoside (4), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,25-diol-3-O-beta-D-xylopyranoside (5), 20xi(1),24xi(2)-epoxy-15alpha-acetoxy-9,19-cyclolanostane-3beta,16beta,25-triol-3-O-beta-D-xylopyranoside (6), and 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,12alpha,15alpha,16beta,25-pentaol-3-O-beta-D-xylopyranoside (7), respectively.


Assuntos
Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Ranunculaceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Cromatografia em Camada Delgada , Cristalografia por Raios X , Glicosídeos/química , Hidrólise , Medicina Tradicional Chinesa , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Saponinas/química , Espectrofotometria Infravermelho , Estereoisomerismo , Triterpenos/química
20.
Zhongguo Zhong Yao Za Zhi ; 27(3): 199-201, 2002 Mar.
Artigo em Chinês | MEDLINE | ID: mdl-12774400

RESUMO

OBJECTIVE: To demonstrate the chemical constituents of Alyxia sinensis. METHOD: The constituents were isolated by column chromatography and identified by advanced physical and spectral analysis. RESULT: Eight compounds have been isolated and elucidated as bauereny acetate(18), scopletin(19), liriodendrin(20), pinoresinol-di-O-beta-D-glucopyranoside(21), daucosterol(22), flaxetin(23), esculin(24), aseculin(25). CONCLUSION: These compounds were found from the plant for the first time, and compound 20,21,23-25 were found from Alyxiae genis for the first time, and compound 18 is firstly been isolated from natural source.


Assuntos
Apocynaceae/química , Plantas Medicinais/química , Triterpenos/isolamento & purificação , Esculina/química , Esculina/isolamento & purificação , Furanos/química , Furanos/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Estrutura Molecular , Triterpenos/química
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