RESUMO
Dracaena cambodiana Pierre ex Gagnep. is well known as a medicinal plant and widely distributed in Vietnam. Phytochemical investigation on the trunks of D. cambodiana lead to the isolation of four undescribed compounds (1-4) together with seven known ones (5-11). Their structures were determined to be pennogenin-24-yl-O-ß-D-glucopyranoside (1), 17α-hydroxycambodianoside C (2), (25R)-27-hydroxypenogenin 3-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (3), (3ß,25R)-17α,22α-dihydroxy-furost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside (4), dracagenin A (5), 1-O-ß-D-glucopyranosyl-2-hydroxy-4-allylbenzene (6), 1-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-2-hydroxy-allylbenzene (7), 2-O-α-L-rhamnopyranosyl-(1â6)-ß-D-glucopyranosyl-1-hydroxy-allylbenzene (8), cinnamrutinoside A (9), icariside D1 (10), and seco-isolariciresinol 9-O-ß-glucopyranoside (11) by extensive spectroscopic investigation, HR-ESI-MS, 1D and 2D NMR spectra. The anti-inflammatory activity of the isolated compounds was evaluated on macrophages. Compounds 1-6 significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Among them, compound 1 showed the best inhibitory activity with an IC50 value of 8.90±0.56â µM.
Assuntos
Derivados de Alilbenzenos , Dracaena , Saponinas , Lipopolissacarídeos/farmacologia , Estrutura Molecular , Óxido Nítrico , Saponinas/farmacologia , Saponinas/química , Glucosídeos/química , Glucosídeos/farmacologiaRESUMO
Three new oleanane-type triterpene saponins, named camphanosides A-C (1-3), along with five known compounds, chikusetsusaponin IVa (4), spinasaponin A 28-O-glucoside (5), (-)-epicatechin (6), (-)-epicatechin 3-O-gallate (7), and (-)-epigallocatechin 3-O-gallate (8) were isolated from the leaves Camellia phanii Hakoda & Ninh. Their structures were established by 1D and 2D-NMR and mass spectral analysis and chemical methods. Moreover, compounds 1-5 were also evaluated for α-glucosidase inhibitory activity. Compounds 1-3 exhibited moderate α-glucosidase inhibitory activity with IC50 values of 230.7±18.0, 251.4±22.7, and 421.4±25.6â µM, respectively.
RESUMO
Phytochemical study on the methanol extract of the stem barks of Aphanamixis polystachya led to the isolation of four previously undescribed ( 1-4) and ten known compounds (5-14). Their chemical structures were elucidated to be 11-methoxysawaranospiroride C (1), 6α,9S,10,13-tetrahydroxymegastigmane-3-one (2), 11-hydroxyaphanamixin B (3), (2Z,6E,13E)-2,6,13-triene-11,15-dihydroxyphytanic acid (4), cinnacasside D (5), cinnacasside E (6), vilsonol F (7), (3S,5R,6S,7E,9R)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (3S,5R,6R,7E,9R)-3,6,9,10-tetrahydroxy-7-en-megastigmane (9), citroside A (10), threo-1-(3,4,5-trimethoxyphenyl)-1,2,3-propanetriol (11), 3,4,5-trimethoxyphenyl-1-O-ß-D-glucopyranoside (12), p-coumaric acid (13), ferulic acid (14) by HR-ESI-MS, ECD, 1D-, and 2D-NMR spectra. Compounds 1, 3, 4, and 9 showed NO production inhibitory activity in LPS activated RAW 264.7 cells with IC50 values of 42.0, 67.9, 20.5, and 78.6 µM, respectively, while the remaining compounds were inactive with IC50 values over 100 µM.
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
Seven steroidal saponins including three new 16,23-cyclocholestanes (1-3) and one new pregane (4) were isolated from the roots of Dracaena cambodiana Pierre ex Gagnep. Their chemical structures were elucidated to be (23R,25R)-26-O-ß-D-glucopyranosyl-16,23-cyclocholesta-5,17(20)-dien-22-one-3ß,16α,26-triol-3-O-α-L-rhamnopyranosyl-(1â2)-[α-L-rhamnopyranosyl-(1â3)]-ß-D-glucopyranoside (1), (23R,25R)-26-O-ß-D-glucopyranosyl-16,23-cyclocholesta-5,17,20(22)-trien-3ß,22,26-triol-3-O-α-L-rhamnopyranosyl-(1â3)-ß-D-glucopyranoside (2), (23R,25R)-16,23-cyclocholesta-5,16,20(22)-trien-3ß,22,26-triol-3-O-α-L-rhamnopyranosyl-(1â3)-ß-D-glucopyranoside (3), 3ß-[(O-α-L-rhamnopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-ß-D-gluco-pyranosyl)oxy]-pregna-5,17(20)-diene-16-one-20-carboxylic acid 4''''-O-ß-D-glucopyranosylisopentyl ester (4), cambodianoside A (5), diosbulbiside C (6), and diosbulbiside D (7), by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1 and 4-7 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW 264.7 cells with IC50 values ranging from 19.03±1.84 to 67.92±3.81â µM, whereas compounds 2 and 3 were inactive with IC50 values over 100â µM.
Assuntos
Dracaena , Lipopolissacarídeos , Saponinas , Camundongos , Animais , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Células RAW 264.7 , Trientina , Saponinas/farmacologia , Saponinas/química , Estrutura MolecularRESUMO
One new labdane-type diterpenoid, 3ß,15-dihydroxylabda-8(17),12E-dien-16,15-olide (1) named curcumatin and twelve known compounds, coronarin D (2), isocoronarin D (3), (E)-labda-8(17),12-diene-15,16-dial (4), zerumin A (5), (E)-labda-8(17),12-dien-15,16-dioic acid (6), furanodiene (7), linderazulene (8), zedoarol (9), zedoarondiol (10), germacrone-1,10-epoxide (11), germacrone-4,5-epoxide (12), and zingiberenol (13) were isolated from the ethanol extract of the roots of Curcuma aromatica Salisb. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and comparing with the NMR data reported in the literature. Compounds 2, 5, and 13 significantly inhibited the nitric oxide production effect in LPS-stimulated RAW 264.7 macrophages with IC50 values of 8.8 ± 1.7, 4.0 ± 0.9, and 6.2 ± 0.4 µM, respectively.
Assuntos
Diterpenos , Sesquiterpenos de Germacrano , Sesquiterpenos , Curcuma/química , Lipopolissacarídeos/farmacologia , Óxido Nítrico , Macrófagos , Sesquiterpenos/farmacologia , Diterpenos/farmacologia , Diterpenos/química , Compostos de Epóxi/farmacologia , Estrutura MolecularRESUMO
One new bithiophene derivative, 5-(but-3-en-1-yn-1-yl)-5'-(methoxymethyl)-2,2'-bithiophene (1), along with twelve known compounds, senecioester (2), tiglinsaureester (3), 5-acetoxymethyl-2'-(but-3-en-1-yn-1-yl)-2,5'-bithiophene (4), 5-(4-isovaleroyloxybut-1-ynyl)-2,2'-bithiophene (5), 5-hydroxymethyl-(2,5':2',5'')-terthienyl tiglate (6), 5-hydroxymethyl-(2,5':2',5'')-terthienyl agelate (7), 5- hydroxymethyl-2,5':2',5''-terthiophene dimethylacrylate (8), 5-methoxymethyl-2,2':5',2''-terthiophene (9), α-terthiophene (10), 1,3,8,9-tetrahydroxycoumestan 3-sulfate (11), demethylwedelolactone (12), and wedelolactone (13) were isolated from the methanol extract of aerial parts of Eclipta prostrata (L.) L. All isolated compounds were evaluated for the protective ability on the HepG2 cells. At the concentration of 100 µM, compounds 11-13 showed the highest hepatoprotective effects, with HepG2 cell viability ranging from 38.68% to 48.54%. Bithiophenes showed higher hepatoprotective cell viability than terthiophenes.
RESUMO
From the fruits of Schisandra cauliflora, five new dimethylbutyrylated dibenzocyclooctadiene lignans, named schisandracaurins A-E, were isolated using separation and chromatographic techniques. Their structures were determined by extensive analyses of HR-ESI-MS, NMR, and ECD spectra. The schisandracaurins A-E potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values from 21.4 to 30.3â µM.
Assuntos
Lignanas , Schisandra , Schisandra/química , Lipopolissacarídeos/farmacologia , Estrutura Molecular , Frutas/química , Lignanas/química , Ciclo-Octanos/farmacologia , Ciclo-Octanos/análise , Ciclo-Octanos/químicaRESUMO
Vitex trifolia L. is a medicinal plant and widely distributed in the northern mountainous areas of Vietnam. Phytochemical study on the fruits of this plant led to the isolation of nine iridoid derivatives (1-9) including three undescribed compounds (1-3). Their structures were elucidated to be 3''-hydroxyscrophuloside A1 (1), 3''-hydroxycallicoside D (2), 2'-p-hydroxybenzoylaucubin (3), 6'-p-hydroxybenzoylmussaenosidic acid (4), nishindaside (5), agnuside (6), 10-O-vanilloylaucubin (7), 6'-O-p-hydroxybenzoyl-gardoside (8), and buddlejoside B (9) based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1, 2, 4, and 8 significantly posessed anti-barterial activity against Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa strains with MIC values in range of 16-64â µg/mL. At concentration of 20â µM, compounds 1-9 did not show cytotoxic effects against human lung cancer cells (PC9).
Assuntos
Anti-Infecciosos , Antineoplásicos , Vitex , Humanos , Iridoides/química , Vitex/química , Frutas/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/análise , Extratos Vegetais/análiseRESUMO
One new phenylpropanoid glycoside, tinosinen A (1) and 13 known compounds, tinosinen (2), citrusin B (3), picraquassioside C (4), erythro-guaiacylglycerol-ß-O-4'-coniferyl alcohol (5), erythro-guaiacylglycerol-8-O-4'-(sinapyl alcohol) ether (6), erythro-syringylglycerol-8-O-4'-(sinapyl alcohol) ether (7), seco-isolariciresinol 9-O-D-ß-glucopyranoside (8), tinosposide A (9), pinoresinol-4'-O-ß-D-glucopyranoside (10), syringaresinol-4'-O-ß-D-glucopyranoside (11), pinoresinol (12), syringaresinol (13), and lirioresino-ß-dimethyl ether (14) were isolated from the stems of Tinospora sinensis (Lour.) Merr. Their structures were established by detailed spectroscopic studies and comparisons with those reported in the literature. Compound 13 showed significant inhibitory NO production (IC50 value of 38.53 ± 1.90 µM) in RAW264.7 macrophages, LPS-stimulated. Compounds 3-7, 11, 12, and 14 inhibited NO production with IC50 values ranging from 38.53 to 99.07 µM.
Assuntos
Tinospora , Tinospora/química , Óxido Nítrico , ÉteresRESUMO
A new furostane saponin, ramosaponin (1), and four known furostane saponins, protodioscin (2), dehydrotomatoside (3), (25 R)-26-O-(ß-D-glucopyranosyl)-furost-5-ene-3ß,22α,26-triol 3-O-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranoside (4), and anguivioside A (5) were isolated from the methanol extract of Allium ramosum seeds. Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for reduction of lipid accumulation in HepG2 cell line. As a result, compound 1 showed significant lipid accumulation inhibitory activity with an IC50 value of 64.32 ± 3.87 µM.
Assuntos
Allium , Saponinas , Allium/química , Saponinas/farmacologia , Saponinas/química , Extratos Vegetais/química , Sementes , Lipídeos , Estrutura MolecularRESUMO
Three new chromanes, malloapeltas J-L (1-3), and one new flavone C-glycoside, malloflavoside (4), together with four known compounds, apigenin 6-C-ß-D-xylopyranosyl-8-C-α-L-arabinopyranoside (5), apigenin 6-C-ß-D-glucopyranosyl-8-C-α-L-arabinopyranoside (6), apigenin 7-O-ß-D-apiofuranosyl-(1â2)-ß-D-glucopyranoside (7), and acantrifoside E (8) were isolated from the methanol extract of the leaves of Mallotus apelta. Their chemical structures were determined using spectroscopic methods, including 1D, 2D NMR, and HR-ESI-MS methods. All the isolated compounds were evaluated their cytotoxic activity against human prostate cancer (PC-3) and human breast cancer (MCF-7) cells, but none of them showed cytotoxicities on both human cancer cell lines.
Assuntos
Flavonas , Mallotus (Planta) , Humanos , Apigenina , Glicosídeos/farmacologia , Glicosídeos/química , Flavonas/farmacologiaRESUMO
Six new iridoid glycosides, myxosmosides A-F (1-6) were isolated from the roots of Myxopyrum smilacifolium (Wall.) Blume. Their chemical structures were determined using, 1D-, 2D-NMR, and mass spectra and chemical methods.
Assuntos
Glucosídeos Iridoides , Oleaceae , Glucosídeos Iridoides/análise , Iridoides/análise , Iridoides/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Raízes de Plantas/químicaRESUMO
Five new seco-labdane-type diterpenoids, caesalatisics A-E (1-5), were isolated from the leaves of Caesalpinia latisiliqua (Cav.) Hattink. Their chemical structures were determined using 1D and 2D NMR, mass spectra, and circular dichroism spectroscopies.
Assuntos
Caesalpinia , Diterpenos , Caesalpinia/química , Diterpenos/análise , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta/químicaRESUMO
Three new furostane saponins, ramofurosides A-C (1-3), and two known saponins, fistulosaponin B (4) and (25R)-26-O-ß-D-glucopyranosyl-1ß,3ß,26-trihydroxyfurosta-5,20(22)-diene-1-O-α-L-rhamnopyranosyl-(1â2)-α-L-arabinopyranoside (5) were isolated from the methanol extract of Allium ramosum seeds. Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for reduction of lipid accumulation in HepG2 cell lines. As a result, compounds 1 and 3 showed a significant reduction in total lipid content by 27.93±3.05 and 27.54±1.68 %, respectively, at a concentration of 100â µM.
Assuntos
Allium , Saponinas , Allium/química , Lipídeos/análise , Metanol , Estrutura Molecular , Extratos Vegetais/química , Saponinas/química , Sementes/químicaRESUMO
One new phenylpropanoid glycoside, myxosmoside I (1) and six known compounds, arenarioside (2), verbacoside (3), 3-formylindole (4), 5-hydroxymethyl furfural (5), D-manitol (6), and glycerol monooleate (7) were isolated from the roots of Myxopyrum smilacifolium (Wall.) Blume. Their chemical structures were determined by 1D-, 2D-NMR, and mass spectra, chemical methods, and compared with those reported in the literature. All compounds were evaluated for α-glucosidase inhibitory effect. Among them, phenylpropanoid glycosides 1-3 significantly inhibited α-glucosidase activity with IC50 values of 30.0 ± 0.9, 66.6 ± 2.3, and 36.9 ± 2.0 µM, respectively.
Assuntos
Glicosídeos Cardíacos , Oleaceae , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Estrutura Molecular , alfa-GlucosidasesRESUMO
The chemical study of the acidic extract of Phaeanthus vietnamensis leaves led to the isolation of one new alkaloid, vietnamine A (1) and eight known alkaloids (R,S)-2N-norberbamunine (2), grisabine (3), 1S,1'R,O,O'-dimethylgrisabine (4), dauricine (5), neothalibrine (6), vietnamine (7), xylopine (8), and argentinine (9) by NMR and MS and comparing with the data reported in the literature. Compounds 1-9 were evaluated for inhibitory NO production in RAW 264.7 macrophages, LPS-stimulated. Compounds 1-3 significantly inhibited on NO production with the IC50 values of 6.8 ± 0.9, 9.8 ± 1.0, and 7.1 ± 0.4 µg/ml, respectively.
Assuntos
Alcaloides , Annonaceae , Alcaloides/química , Alcaloides/farmacologia , Annonaceae/química , Lipopolissacarídeos/farmacologia , Macrófagos , Estrutura Molecular , Óxido Nítrico , Óxido Nítrico Sintase Tipo II , Extratos Vegetais/químicaRESUMO
Truxinic acid sucrose diesters analogs possess interesting chemical structure by the presence of cyclobutane-ring and macrocyclic sucrose diesters moieties which are rarely found from natural sources. This paper describes the isolation and structural elucidation of four new sucrose diesters of substituted truxinic acids, trigohonbanosides A-D (1-4), from the leaves of Trigonostemon honbaensis. Their chemical structures were elucidated by HR-ESI-MS, NMR, and CD spectroscopic methods. At a concentration of 30 µM, compounds 1-4 moderately inhibited ANO-1 activity with inhibitory percentages of 27.7 ± 1.10%, 35.6 ± 0.92%, 43.7 ± 1.61%, and 40.8 ± 1.25%, respectively.
Assuntos
Anoctamina-1/antagonistas & inibidores , Proteínas de Neoplasias/antagonistas & inibidores , Fenantrenos/química , Folhas de Planta/química , Humanos , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
Mallotusapelta(Lour.) Müll.Arg has been used in traditional medicine for the treatment of chronic hepatitis. Six new chromene derivatives, malloapeltas C-H (1-6) and one known compound, malloapelta B (7) were isolated and structured from the leaves of M.apelta. Two pairs of enantiomers (1a/1b and 2a/2b) were successfully separated by chiral high-pressure liquid chromatography (HPLC). The structures and absolute configurations of compounds were determined using spectroscopic methods, including 1D, 2D NMR, and MS and quantum chemical calculation methods. All compounds were evaluated for cytotoxic activity using cell counting kit-8 (CCK-8) assay against ovariancancer cell line (TOV-21G). Compounds 1-5 and 7 exhibited significant growth and viability inhibitory effects with GI50 values ranging from 0.06 to 10.39 µM and IC50 values ranging from 1.62 to 10.42 µM on ovarian cancer cell line, TOV-21G. The most cytotoxic compounds 2, 3, and 7 were chosen for studying in apoptosis mechanism. Compounds 2, 3, and 7-induced apoptosis as evidenced by activated caspase 8, caspase 9, and PARP, increased Bak and Bax, and decreased Bcl-xL and survivin. Moreover, compounds 2, 3, and 7 significantly inhibited the NF-κB signaling pathway. Taken together, our findings propose the potential application of compounds 2, 3, and 7 for treating cancer via modulating NF-κB activity.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Benzopiranos/farmacologia , Mallotus (Planta)/química , Extratos Vegetais/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Benzopiranos/química , Benzopiranos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Camundongos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Células RAW 264.7 , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Two new oligostilbenes, caragasinins D and E, along with four known compounds, kobophenol A, α-viniferin, wistin, and 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid, were isolated from the roots of Caragana sinica. These compounds were spectroscopically analyzed for their structures and configurations and compared with existing data. The configurations of caragasinins D and E were elucidated by 1 H-NMR spectroscopy, CD spectroscopy, and time-dependent density-functional theory simulated ECD spectral data. All six compounds were evaluated for their inhibitory activity against neuraminidase (NA) from Clostridium perfringens. Among the tested compounds, 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid demonstrated statistically significant NA inhibitory activity, which was comparable to the positive control, mangiferin.