RESUMO
Four previously undescribed diastereomeric lignan glycosides, namely cistadesertosides B-E (1-4) were isolated from the stems of cultural Cistanche deserticola in Tarim desert. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses, including IR, HR-ESI-MS, 1D and 2D NMR, circular dichroism (CD) data and chemical degradation. The inâ vitro anti-inflammatory activity of the isolates was also investigated. It showed that compounds 3 and 4 exhibited potential effects with IC50 values of 21.17â µM and 26.97â µM, respectively (positive control quercetin, IC50 , 10.01â µM).
Assuntos
Cistanche , Lignanas , Glicosídeos/farmacologia , Glicosídeos/química , Lignanas/farmacologia , Lignanas/química , Cistanche/química , Extratos Vegetais/química , Anti-InflamatóriosRESUMO
Trace amounts of components in traditional Chinese medicine are considered pharmacological active substances used for treating many serious diseases. However, purifying all the trace substances and making clear their structures are not easy. In this context, high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry based molecular networking was applied to investigate the chemical constituents of the roots of Aconitum kusnezoffii Reichb., which led to the identification of 33 nodes in different groups (N1-N33). Based on the excremental fragmentation pathway of known diterpenoid alkaloids (1-9) and comparisons of characteristic ions and characteristic loss of analogs in literature, the structures of unknown ions were deduced. This work lays a foundation for the evaluation of the clinical basis and mechanism of traditional Chinese medicine from the aspects of chemistry. In this paper, the method speculation of unknown natural products by means of molecular network method is expected to be applied in the discovery and change law of relevant active components in clinical pharmacology and the change of complex systems caused by trace active compounds.
Assuntos
Aconitum , Alcaloides , Diterpenos , Medicamentos de Ervas Chinesas , Aconitum/química , Alcaloides/análise , Cromatografia Líquida de Alta Pressão , Cromatografia Líquida , Diterpenos/análise , Medicamentos de Ervas Chinesas/química , Espectrometria de Massas em TandemRESUMO
In order to clarify the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The chemical constituents were isolated by column chromatography, such as silica gel, Sephadex LH-20, MCI gel, ODS and semi-preparative HPLC, and their structures were determined on the basis of MS, NMR spectroscopic analysis, and comparison with literature data. Four compounds were isolated from the 85% ethanol extract of the stems of C. cultured in Tarim desert. Their structures were identified as cis-tubuloside (1), cis-cistanoside (2), cis-cistanoside J (3), and cis-isocistanoside C(4). Compounds 1-4 were four new cis-phenylethanoid glycosides. Herein, we firstly report the ¹H, ¹³C-NMR data of the new compounds(1-4) for the first time. This study will provide the scientific evidence for comprehensively analyzing the chemical constituents of C. deserticola cultured in Tarim desert.
Assuntos
Cistanche/química , Glicosídeos/química , Caules de Planta/química , China , Cromatografia Líquida de Alta Pressão , Clima Desértico , Glicosídeos/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/químicaRESUMO
In order to clarify the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The chemical constituents were isolated by column chromatography, such as silica gel, Sephadex LH- 20, MCI gel, ODS and semi-preparative HPLC, and their structures were determined on the basis of MS, NMR spectroscopic analysis and/or comparison with literature data. Eleven lignans were isolated from the 85% ethanol extract of the stems of C. deserticola cultured in Tarim desert. Their structures were identified as (+)-syringaresinol-4'-O-ß-D-glucopyranoside (1), (+)-isoeucommin A (2), eucommin A (3), (+)-pinoresinol monomethylether ß-D-glucoside (4), lariciresinol 4'-O-ß-D-glucopyranoside (5), lariciresinol 4-O-ß-D-glucopyranoside (6), conicaoside (7), dehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside (8), dehydrodiconiferyl alcohol γ'-O-ß-D-glucoside (9), citrusin A (10), and alaschanioside A (11). Compounds 1, 3-7, 10 and 11 were isolated from this genus for the first time, and compounds 2, 8 and 9 were obtained from this species for the first time.
Assuntos
Cistanche/química , Lignanas/isolamento & purificação , Cistanche/crescimento & desenvolvimento , Lignanas/química , Caules de Planta/químicaRESUMO
Phytochemical investigation on the aerial parts of Corydalis impatiens (pall.) Fisch (Papaveraceae) resulted in the identification of four previous undescribed benzylisoquinoline alkaloids, impatienines A-D (1-4), together with 14 known analogues (5-18). The structures of these compounds were elucidated by extensive spectroscopic analysis (IR, HR-ESIMS, 1D- and 2D-NMR) as well as ECD calculations. All the compounds obtained were investigated for their inhibitory effect on the growth of A549, H1299 and HepG2 cancer cells. Compounds 7 and 15 exhibited pronounced inhibition against the A549 cancer cells with IC50 values of 6.81 µM and 3.17 µM, while the positive control cisplatin was 1.83 µM. Compounds 1-3 showed moderate inhibitory on the H1299 cancer cells. Compounds 4, 10-12, and 16 showed signiffcant activity against HepG2 cancer cells with IC50 values range of 4.41-8.75 µM.
Assuntos
Alcaloides , Benzilisoquinolinas , Corydalis , Impatiens , Corydalis/química , Estrutura Molecular , Alcaloides/química , Espectroscopia de Ressonância Magnética , Componentes Aéreos da Planta/químicaRESUMO
In order to clarify the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The chemical constituents were isolated by column chromatography, over silica gel, Sephadex LH-20, MCI gel, ODS and semi-preparative HPLC, and their structures were determined on the basis of MS, NMR spectroscopic data analysis, physicochemical properties and/or comparison with literature data Seventeen compounds were isolated from the 85% ethanol extract of the stems of C. deserticola cultured in Tarim desert. Their structures were identified as salsaside B (1), syringin (2), demethyl syrinyin (3), coniferin (4), (2E,6E)-3,7-dimethyl-8-hydroxyoctadien-1-O-beta-D-glucoside (5), (+)-syringaresinol (6), 2S,3S, 4S-trihydroxypentanoic acid (7), panaxytriol (8), beta-sitosterol-3-O-beta-D-xylopyranoside (9), androsin (10), 3-methyl-but-2-en-1-yl-beta-D-glucopyranoside (11), benzyl-glucopyranoside (12), 4-hydroxybenzyl-beta-D-glucoside (13), nicotinamide (14), p-hydroxybenzoic acid (15), 4-hydroxy-benzeneethanol (16), and galactitol (17). Compounds 3, 6-13 were isolated from this genus for the first time, and compounds 1, 4 and 5 were obtained from this species for the first time.
Assuntos
Cistanche/química , Cistanche/crescimento & desenvolvimento , Clima Desértico , Medicamentos de Ervas Chinesas/análise , Caules de Planta/química , Medicamentos de Ervas Chinesas/isolamento & purificaçãoRESUMO
Four new compounds, impatienines E-H (1-4), together with 18 known ones (R)-N-methylcoclaurine (5), impatienine I (6), thalifoline (7), iseluxine (8), pisoquinoline (9), corydaldine (10), northalifoline (11), noroxyhydrastinine (12), 6,7-methylenedioxy-1(2H)-isoquinolinone (13), N-methylcorydaldine (14), oxyhydrastinine (15), corypalline (16), N-trans-feruloylmethoxytyramine (17), N-trans-feruloyldopamine (18), N-trans-feruloyltyramine (19), N-trans-sinapoyltyramine (20), N-cis-feruloyltyramine (21), N-cis-sinapoyltyramine (22) were obtained from the aerial parts of Corydalis impatiens (pall.) Fisch. Their structures were elucidated by extensive spectroscopic analysis (1D- and 2D-NMR, HR-ESIMS, IR, UV) and/or comparison with reported literature. The inhibitory effects of these isolates were also evaluated against the growth of cancer cells (A549, H1299 and HepG2). Compounds 2 and 4 showed significant inhibitory effect on HepG2 cancer cells with IC50 values of 8.62, 8.32 µM, respectively (positive control cisplatin: IC50, 6.32 µM). Compounds 22 and 4 exhibited moderate inhibitory effects against A549 cancer cells, and the IC50 values were 7.78 and 12.54 µM, respectively (positive control cisplatin: IC50, 1.83 µM).
RESUMO
We describe a facile method to synthesize a new type of catalyst by electrodepositing Ag nanocrystals (AgNCs) on the different polymer dyes, Poly (methylene blue) (PMB) or Poly (4-(2-Pyridylazo)-Resorcinol) (PAR) modified graphenecarbon spheres (GS) hybrids. The self-assembled GS take dual advantages of carbon spheres and graphene. Carbon spheres acts as nano-spacers prevent the aggregation of graphene and guarantee the fast electron transfer of GS. Secondly, polymerized dyes used here are beneficial for AgNCs growing as a linker. The effects of dyes on the growth habits, morphologies and catalytic properties for AgNCs were investigated. A novel electrochemical nonenzymatic sensor for hydrogen peroxide (H2O2) detection is fabricated based on the Ag/Polymer dyes/GS ternary composites modified glass carbon electrode (GCE) for the first time. It was found that the proposed electrodes, especially for Ag/PMB/GS/GCE, displayed a peculiar electrocatalytic activity towards H2O2 reduction synergistically as compared to Ag/PAR/GS/GCE or Ag/GS/GCE alone. Ag/PMB/GS/GCE showed a linear response over the H2O2 concentration range of 0.5 to 1112⯵M. The detection limit and sensitivity is 0.15⯵M and 400⯵Aâ¯mM-1â¯cm-2, respectively. These outstanding results enable the practical application of Ag/PMB/GS/GCE for the H2O2 tracking released from MCF-7 (human breast cancer cells) with satisfactory results.
Assuntos
Corantes/química , Grafite/química , Peróxido de Hidrogênio/análise , Azul de Metileno/análogos & derivados , Polímeros/química , Resorcinóis/química , Prata/química , Técnicas Biossensoriais/métodos , Neoplasias da Mama/química , Técnicas Eletroquímicas/métodos , Feminino , Humanos , Limite de Detecção , Células MCF-7RESUMO
In order to determine the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The constituents were isolated by silica gel, Sephadex LH-20, MCI gel, ODS column chromatography, and semi-preparative HPLC. Their structures were determined on the basis of MS and NMR spectroscopic analyses, by chemical methods, and/or comparison with literature data. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 mouse microglial cells. Nine iridoids were isolated and identified as cistadesertoside A (1), cistanin (2), cistachlorin (3), 6-deoxycatalpol (4), gluroside (5), kankanoside A (6), ajugol (7), bartsioside (8), and 8-epi-loganic acid (9). Compound 9 exhibited potent inhibition on the NO production with an IC50 value being 5.2 µmol·L(-1), comparable to the positive control quercetin (4.3 µmol·L(-1)). Compound 1 was a new iridoid, and compounds 5, 6, and 8 were isolated from this species for the first time.
Assuntos
Anti-Inflamatórios/farmacologia , Cistanche/química , Iridoides/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Iridoides/química , Iridoides/isolamento & purificação , Camundongos , Caules de Planta/químicaRESUMO
Five new phenylethanoid glycosides, cistanosides J-N (1-5), together with 15 known ones (6-20) were isolated from the stems of Cistanche deserticola cultured in Tarim desert, China. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, HR-ESIMS, 1D- and 2D-NMR) and chemical degradation. All the compounds obtained were examined for their inhibitory effect on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse microglial cells (BV-2 cells), and compounds 2 and 8 showed potent inhibition on the NO production with IC50 values of 14.94 µM and 14.32 µM, respectively.