RESUMO
Three previously undescribed compounds named rauvolphyllas A-C (1-3), along with thirteen known compounds, 18ß-hydroxy-3-epi-α-yohimbine (4), yohimbine (5), α-yohimbine (6), 17-epi-α-yohimbine (7), (E)-vallesiachotamine (8), (Z)-vallesiachotamine (9), 16S-E-isositsirikine (10), Nb -methylisoajimaline (11), Nb -methylajimaline (12), ajimaline (13), (+)-lyoniresinol 3α-O-ß-D-glucopyranoside (14), (+)-isolarisiresinol 3α-O-ß-D-glucopyranoside (15), and (-)-lyoniresinol 3α-O-ß-D-glucopyranoside (16) were isolated from the aerial parts of Rauvolfia tetraphylla L. Their chemical structures were elucidated based on the extensive spectroscopic interpretation of HR-ESI-MS, 1D and 2D NMR spectra. The absolute configurations of 2 and 3 were determined by experimental ECD spectra. Compounds 5, 6, 7, and 11-13 exhibited nitric oxide production inhibition activity in LPS-activated RAW 264.7 cells with the IC50 values of 79.10, 44.34, 51.28, 33.54, 37.67, and 28.56â µM, respectively, compared to that of the positive control, dexamethasone, which showed IC50 value of 13.66â µM. The other isolates were inactive with IC50 values over 100â µM.
Assuntos
Alcaloides , Anisóis , Lignanas , Naftalenos , Rauwolfia , Animais , Camundongos , Lignanas/química , Células RAW 264.7 , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Alcaloides/análise , Espectroscopia de Ressonância Magnética , Componentes Aéreos da Planta/química , Ioimbina , Estrutura MolecularRESUMO
Two neolignan glycosides including a new one (1), along with seven iridoid glycosides (3 - 9) and nine flavonoid glycosides (10 - 18), were isolated from the leaves of Vaccinium bracteatum. Their structures were established mainly on the basis of 1D/2D NMR and ESIMS analyses, as well as comparison to known compounds in the literature. The structure of 1 with absolute stereochemistry was also confirmed by chemical degradation and ECD calculation. Selective compounds showed antiradical activity against ABTS and/or DPPH. Moreover, several isolates also suppressed the production of ROS in RAW264.7 cells and exerted neuroprotective effect toward PC12 cells.
Assuntos
Flavonoides , Glicosídeos , Lignanas , Folhas de Planta , Folhas de Planta/química , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/isolamento & purificação , Animais , Camundongos , Células PC12 , Glicosídeos/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Estrutura Molecular , Lignanas/química , Lignanas/farmacologia , Lignanas/isolamento & purificação , Ratos , Células RAW 264.7 , Vaccinium/química , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/isolamento & purificação , Iridoides/química , Iridoides/farmacologia , Iridoides/isolamento & purificação , Glicosídeos Iridoides/química , Glicosídeos Iridoides/farmacologia , Glicosídeos Iridoides/isolamento & purificação , Espécies Reativas de Oxigênio , Picratos/farmacologiaRESUMO
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
Previously, the authors conducted phytochemical investigations of the aerial parts of Larrea tridentata and reported triterpene glycosides and lignan derivatives. In continuation of the preceding studies, 17 lignans and lignan glycosides (1-17) were isolated, including seven new compounds (1-7). Herein, the structure of the new compounds was determined based on spectroscopic analysis and enzymatic hydrolysis. The cytotoxicity of 1-17 against HL-60 human promyelocytic leukemia cells was examined. Compounds 4-11 and 14-16 were cytotoxic to HL-60 cells, with IC50 values in the range of 2.7-17 µM. Compound 6, which was the most cytotoxic among the unprecedented compounds, was shown to induce apoptotic cell death in HL-60 cells.
Assuntos
Antineoplásicos Fitogênicos/química , Glicosídeos/química , Larrea/química , Lignanas/química , Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Cisplatino/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/farmacologia , Células HL-60 , Humanos , Lignanas/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Componentes Aéreos da Planta/química , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Phytochemical investigation of 95% ethanol extract of the fruit of Forsythia suspensa resulted in the isolation of two new furofuran lignan glycoside derivatives pinoresinoside A (1) and phillyrigeninside A (2), along with three known ones. Their structures were established based on extensive spectroscopic data analyses and comparison with literature data. Absolute configuration of 1 was determined by CD method. In addition, compounds 1 and 2 were revealed to show in vitro cytotoxicity against human tumor cell lines (SGC-7901, MCF-7 and HepG2), with IC50 values ranging from 16.77 to 37.35 µM. [Formula: see text].
Assuntos
Forsythia , Lignanas , Frutas , Glicosídeos , Humanos , Estrutura MolecularRESUMO
A new lignan glycoside, astrayunoside A (1), along with eight known compounds (2-9), were obtained from the methanol extract of roots of Astragalus yunnanensis. All the compounds were obtained from A. yunnanensis for the first time. Their structures were elucidated by extensive spectroscopic analysis (1D and 2D-NMR, MS, UV, CD, and IR). The weak antibacterial activities of the crude extracts of A. yunnanensis against Staphyloccocus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa, Shigella dysenteriae, Salmonella typhi H901, Candida albicans, Streptococcus mutans, and Actinomyces viscosus were observed.
Assuntos
Lignanas , Extratos Vegetais , Antibacterianos , Glicosídeos , Testes de Sensibilidade Microbiana , Estrutura MolecularRESUMO
In our quest for structurally intriguing compounds from Korean medicinal plant sources, chromatographic separation of the 80% MeOH extract from Firmiana simplex resulted in the isolation and identification of three new lignan glycosides (1-3), together with six known lignan glycosides (4-9). The structures of 1-3 were determined on the basis of spectroscopic analyses, including extensive 2D-NMR and enzyme hydrolysis. Nitric oxide (NO) production was evaluated in the lipopolysaccharide-activated microglial cell line, BV-2 to investigate the anti-neuroinflammatory effects of the isolated compounds (1-9). Compound 7 marginally inhibited NO levels with IC50 values of 59.83 µM.
Assuntos
Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , Malvaceae/química , Óxido Nítrico/antagonistas & inibidores , Animais , Linhagem Celular , Relação Dose-Resposta a Droga , Glicosídeos/química , Lignanas/química , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Relação Estrutura-AtividadeRESUMO
Three new C-methylated phenylpropanoid glycosides (1, 2), a new 8-4'-oxyneolignan (3), together with two known analogs (4, 5), were isolated from the rhizomes of Imperata cylindrical Beauv. var. major (Nees) C. E. Hubb. Their structures were determined by spectroscopic and chemical methods. Compounds 1, 2, and 5 (10 µM) exhibited pronounced hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in vitro assays. Furthermore, their antioxidant activities against Fe2+-cysteine-induced rat liver microsomal lipid peroxidation and the effects on the secretion of TNF-α in murine peritoneal macrophages (RAW264.7) induced by lipopolysaccharides were evaluated.
Assuntos
Glicosídeos/química , Glicosídeos/farmacologia , Poaceae/química , Rizoma/química , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Células Hep G2 , Humanos , Peroxidação de Lipídeos , Macrófagos/efeitos dos fármacos , Camundongos , Microssomos Hepáticos/efeitos dos fármacos , Células RAW 264.7 , RatosRESUMO
Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (3â»7) and nine known flavonoid glycosides (8â»14). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 4â»6 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 < 30.0 µM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining.
Assuntos
Flavonoides/química , Glicosídeos/química , Glicosídeos/farmacologia , Lespedeza/química , Lignanas/química , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antivirais/química , Antivirais/farmacologia , Linhagem Celular Tumoral , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Células MCF-7 , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Vírus/efeitos dos fármacosRESUMO
This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 µM.
Assuntos
Acanthaceae/química , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lignanas/isolamento & purificação , Peptídeos Cíclicos/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Concentração Inibidora 50 , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Peptídeos Cíclicos/química , Peptídeos Cíclicos/farmacologiaRESUMO
Phytochemical investigation on the stems of Trigonostemonheterophyllus led to the isolation of a new lariciresinol-based lignan glycoside, trigonoheteran (1), together with a known lignan glycoside, aviculin (2). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR (HMQC, (1)H-(1)H COSY, HMBC, and NOESY).
Assuntos
Euphorbiaceae/química , Glicosídeos/isolamento & purificação , Lignanas/isolamento & purificação , Furanos , Glicosídeos/química , Lignanas/química , Estrutura MolecularRESUMO
Three new phenolic glycosides (1-3) and a new lignan glycoside (4), together with five known compounds (5-9) were isolated from the ethanol extract of the aerial part of Gaultheria leucocarpa var. yunnanensis (Franch.) T.Z.Hsu & R.C.Fang. Their structures were determined on the basis of spectroscopic techniques, experimental and calculated ECD spectra, acid hydrolysis, and enzymatic hydrolysis experiments. All the isolates were evaluated for their anti-inflammatory and antioxidant activities. Compounds 7 and 8 exhibited inhibitory effects against the LPS-induced production of NO with IC50 of 63.71 and 10.66 µM, respectively, compared to L-NMMA having an IC50 of 6.95 µM. Besides, compound 7 also represented significant DPPH radical scavenging activity with EC50 of 18.75 µM, comparable with vitamin C (EC50 = 15.77 µM).
Assuntos
Glicosídeos Cardíacos , Gaultheria , Lignanas , Glicosídeos/química , Lignanas/farmacologia , Gaultheria/química , Estrutura Molecular , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/químicaRESUMO
Buxrugulosides A-E, four lignan glycosides (1-4) and a protocatechuate derivative (5) featuring a rare (N, N-diethyl)methyl amino group at aromatic rings, were obtained from the aerial parts of Buxus rugulosa, which is famous for treating coronary heart disease. Their structures including absolute configurations were elucidated by HRMS, 1D and 2D NMR, and by comparing their CD data with previous reports. Compound 1 was a rare sesquilignan, and all of these compounds were the first example of lignans with (N, N-diethyl)methyl amino group.
Assuntos
Buxus , Lignanas , Glicosídeos , Estrutura Molecular , Extratos VegetaisRESUMO
A novel sesquilignan compound (1), possesing an unusual carbon skeleton of aryltetralin unit linked with a C6-C3 unit and a five-membered ring by a C-7â³ and C-4 linkage pattern via an oxygen atom, and a new lignan glycoside (2) have been isolated from the twigs and leaves of Illicium majus. Their structures were determined by spectroscopic analysis and chemical methods. The absolute configurations of 1 and 2 are confirmed by observing the circular dichroism. At 10⯵M, Compounds 1 and 2 showed in Vitro inhibitory activity against the release of ß-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.
Assuntos
Glucuronidase/antagonistas & inibidores , Glicosídeos/química , Illicium/química , Lignanas/química , Neutrófilos/efeitos dos fármacos , Animais , Células Cultivadas , Dicroísmo Circular , Estrutura Molecular , Folhas de Planta/química , Fator de Ativação de Plaquetas , RatosRESUMO
Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17. Comparison of the spectral data showed good agreement. Glycosylation was investigated using four different glycosyl donors. Only the Koenigs-Knorr condition using silver trifluoromethanesulfonate with 1,1,3,3-tetramethylurea provided the glycosylated product. Deprotection and purification using reverse-phase high-performance liquid chromatography gave schizandriside (1) and its diastereomer saracoside (2). Synthesized 1, 2 and 18 showed antioxidant activity with IC50 = 34.4, 28.8, 53.0 µM, respectively.
Assuntos
Antioxidantes/farmacologia , Glicosídeos/síntese química , Lignanas/química , Lignina/síntese química , Naftóis/síntese química , Extratos Vegetais/química , Lignanas/síntese químicaRESUMO
A new lignan glycoside, (7S,8R)-guaiacylglycerol-ferulic acid ether-7-O-ß-D-glucopyranoside (1), along with five known phenylpropanoids (2-6) and seven phenylpropanoid glycosides (7-13), were isolated from the stems of Zanthoxylum armatum DC. Their structures were elucidated by spectroscopic analysis. Compounds 2-8 and 11-13 were first isolated from Rutaceae and the others were isolated for the first time from Z. armatum.
Assuntos
Lignanas/química , Zanthoxylum/química , Glicosídeos/química , Hidrólise , Extratos Vegetais/química , Caules de Planta/química , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria UltravioletaRESUMO
Chemical investigation of the aerial parts of Uvaria rufa (Dunal) Blume collected from Vietnam yielded one new lignan glycoside, ufaside (1), along with six known compounds, oxoanolobine (2), ergosta-4,6,8(14),22-tetraen-3-one (3), catechin (4), epicatechin (5), daucosterol (6) and glutin-5-en-3-one (7). Their chemical structures were determined by using NMR, HR-MS spectroscopic analyses and in comparison with the reported data. A cytotoxic analysis of U. rufa herb extracts was performed for the first time using nine human cancer cell lines (MCF-7, MDA-MB-231, LNCaP, MKN7, SW480, KB, LU-1, HepG2 and HL-60) derived from different tumour types. Of these seven constituents, compounds 2 and 3 displayed moderate cytotoxicity against the human lung adenocarcinoma cell line (LU-1) with IC50 values of 9.22 ± 1.02 µg/mL and 10.21 ± 1.16 µg/mL, respectively.
Assuntos
Antineoplásicos Fitogênicos/química , Glicosídeos/química , Lignanas/química , Componentes Aéreos da Planta/química , Uvaria/química , Linhagem Celular Tumoral , Colestenonas , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/isolamento & purificação , Humanos , Lignanas/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
Acetylcholinesterase (AChE) inhibitors increase the availability of acetylcholine in central cholinergic synapses and are the most promising drugs currently available for the treatment of Alzheimer's disease (AD). Our screening study indicated that the water fraction of the methanolic extract of Lycopodiella cernua (L.) Pic. Serm. significantly inhibited AChE in vitro. Bioassay-guided fractionation led to the isolation of a new lignan glycoside, lycocernuaside A (12), and fourteen known compounds (1-11 and 13-15). Compound 7 exhibited the most potent AChE inhibitory activity with an IC50 value of 0.23 µM. Compound 15 had the most potent inhibitory activity against BChE and BACE1 with IC50 values of 0.62 and 2.16 µM, respectively. Compounds 4 and 7 showed mixed- and competitive-type AChE inhibition. Compound 7 noncompetitively inhibited BChE whereas 15 showed competitive and 8, 13, and 14 showed mixed-type inhibition. The docking results for complexes with AChE or BChE revealed that inhibitors 4, 7, and 15 stably positioned themselves in several pocket/catalytic domains of the AChE and BChE residues.