RESUMO
Two new biphenyl-type neolignan derivatives, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1) and 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), were isolated from the twigs of Magnolia denudata, together with six known compounds (3-8). The structures of 1 and 2 were determined through extensive 1D- and 2D-NMR and mass-spectrometric analyses. Magnolol (6) and honokiol (7) exhibited potent inhibition (IC50 values=4.4±0.2 and 0.71±0.13â µg/ml, resp.) of O$\rm{{_{2}^{{^\cdot} -}}}$ generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). In addition, 2-[2-(hydroxymethyl)-1-benzofuran-5-yl]-4-(prop-2-en-1-yl)phenol (1), 2'-ethoxy-5,5'-di(prop-2-en-1-yl)biphenyl-2-ol (2), magnolol (6), and vanillic acid (8) inhibited fMLP/CB-induced elastase release with IC50 values=6.4±1.5, 2.4±0.4, 1.5±0.2, and 4.8±0.5â µg/ml, respectively.
Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Compostos de Bifenilo/química , Compostos de Bifenilo/farmacologia , Lignanas/química , Lignanas/farmacologia , Magnolia/química , Adulto , Anti-Inflamatórios/isolamento & purificação , Compostos de Bifenilo/isolamento & purificação , Humanos , Lignanas/isolamento & purificação , Neutrófilos/efeitos dos fármacos , Neutrófilos/imunologia , Superóxidos/imunologia , Adulto JovemRESUMO
Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (4-18). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4, 9, 12, and 15 exhibited inhibition (half maximal inhibitory concentration (IC50) values ≤7.65 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, 4, 8 and 9 inhibited fMLP/CB-induced elastase release with IC50 values ≤8.17 µg/mL. This investigation reveals bioactive isolates (especially 1, 2, 4, 8, 9, 12 and 15) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.
Assuntos
Cumarínicos/farmacologia , Inflamação/patologia , Neutrófilos/imunologia , Casca de Planta/química , Caules de Planta/química , Zanthoxylum/química , Adulto , Cumarínicos/química , Cumarínicos/isolamento & purificação , Citocalasina B/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , N-Formilmetionina Leucil-Fenilalanina/análogos & derivados , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/efeitos dos fármacos , Superóxidos/metabolismo , Adulto JovemRESUMO
A new limonoid, swietemacrophin (1), was isolated from the seeds of Swietenia macrophylla, together with five known compounds 2-6. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Swietemacrophin (1), humilinolide F (2), 3,6-O,O-diacetylswietenolide (3), 3-O-tigloylswietenolide (4), and swietemahonin E (5) exhibited inhibition (IC50 values≤45.44 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). Compounds 1, 4, 5, and swietenine (6) showed potent inhibition with IC50 values≤36.32 µM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Limoninas/isolamento & purificação , Meliaceae/química , Sementes/química , Triterpenos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Humanos , Concentração Inibidora 50 , Limoninas/química , Limoninas/farmacologia , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , N-Formilmetionina Leucil-Fenilalanina/análogos & derivados , N-Formilmetionina Leucil-Fenilalanina/antagonistas & inibidores , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/citologia , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Extratos Vegetais/química , Cultura Primária de Células , Relação Estrutura-Atividade , Superóxidos/antagonistas & inibidores , Triterpenos/química , Triterpenos/farmacologiaRESUMO
A new dihydroagarofuran-based sesquiterpene, microjaponin (1), was isolated from the stem of Microtropis japonica. Its structure was determined by in-depth spectroscopic and mass-spectrometric analyses. Microjaponin (1) exhibited potent in vitro antituberculosis activity, with an MIC value of 12.5 µg/ml against Mycobacterium tuberculosis H37 Rv.
Assuntos
Antituberculosos/química , Antituberculosos/farmacologia , Benzoatos/química , Benzoatos/farmacologia , Celastraceae/química , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Antituberculosos/isolamento & purificação , Benzoatos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Caules de Planta/química , Sesquiterpenos/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Two new thymol (=5-methyl-2-(1-methylethyl)phenol) derivatives, 8,10-didehydro-9-(3-methylbutanoyl)thymol 3-O-tiglate (1) and 9-O-angeloyl-8-methoxythymol 3-O-isobutyrate (2), were isolated from the root of Eupatorium cannabinum ssp. asiaticum, together with six known compounds, 3-8. The structures of 1 and 2 were determined through extensive 1D/2D-NMR and MS analyses. Among the isolates, 9-acetoxy-8,10-epoxythymol 3-O-tiglate (3) was the most cytotoxic, with IC50 values of 0.02±0.01, 1.02±0.07, and 1.36±0.12â µg/ml, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines. In addition, 10-acetoxy-9-O-angeloyl-8-hydroxythymol (4) and eupatobenzofuran (6) exhibited cytotoxicities, with IC50 values of 1.14±0.16 and 2.63±0.22, and 7.63±0.94 and 2.31±0.14â µg/ml, respectively, against DLD-1 and CCRF-CEM cell lines.
Assuntos
Eupatorium/química , Raízes de Plantas/química , Timol/isolamento & purificação , Linhagem Celular , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Timol/química , Timol/farmacologiaRESUMO
The fruit of Cnidium monnieri is commercially used as healthcare products for the improvement of impotence and skin diseases. Three new coumarins, 3'-O-methylmurraol (1), rel-(1'S,2'S)-1'-O-methylphlojodicarpin (2), and (1'S,2'S)-1'-O-methylvaginol (3), have been isolated from the fruits of C. monnieri, together with 14 known compounds (4-17). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4-12, and 14-17 exhibited inhibition (IC50 ≤ 7.31 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7, 9-11, 15, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.83 µg/mL. This investigation reveals that bioactive isolates (especially 6, 7, 14, and 17) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.
Assuntos
Anti-Inflamatórios/química , Cnidium/química , Cumarínicos/química , Frutas/química , Adulto , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Degranulação Celular/efeitos dos fármacos , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Humanos , Neutrófilos/efeitos dos fármacos , Neutrófilos/imunologia , Neutrófilos/fisiologia , Elastase Pancreática/imunologia , Superóxidos/imunologia , Adulto JovemRESUMO
Muntingia calabura (Tiliaceae) is commercially used in healthcare for the improvement of hypertension, myocardial infarction, spasm, and inflammatory conditions. Its fruits can be processed into jam and the leaves can be used for making tea. In the work reported herein a new biflavan, (M),(2S),(2''S)-,(P),(2S),(2''S)-7,8,3',4',5',7'',8'',3''',4''',5'''-decamethoxy-5,5'' biflavan (1), a new flavone, 4'-hydroxy-7,8,3',5'-tetramethoxyflavone (2), and a new dihydrochalcone, (R)-2',ß-dihydroxy-3',4'-dimethoxydihydrochalcone (3), have been isolated from the stem wood of M. calabura, together with 12 known compounds (4-15). The structures of these new compounds were elucidated by the interpretations of extensive spectroscopic data. Among the isolated compounds, 5-hydroxy-7-methoxyflavone (5), quercetin (6), and (2S)-7-hydroxyflavanone (10) exhibited potent inhibition of fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 1.77 ± 0.70, 3.82 ± 0.46, and 4.92 ± 1.71 µM, respectively.
RESUMO
A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (4-14). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (-)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (-)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.79 µg/mL) of superoxide anion generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 4, 8, and 11 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 5.48 µg/mL.
Assuntos
Benzoatos/química , Benzofenantridinas/farmacologia , Cinamatos/química , Hidroxibutiratos/química , Neutrófilos/efeitos dos fármacos , Zanthoxylum/química , Benzofenantridinas/química , Benzofenantridinas/isolamento & purificação , Humanos , Superóxidos/antagonistas & inibidoresRESUMO
Reactive oxygen species (ROS) and granule proteases produced by human neutrophils contribute to the pathogenesis of inflammatory diseases. The MeOH extract of the stem bark of Magnolia officinalis showed potent inhibitory effects on superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Five biphenyl-type neolignan derivatives, 5-allyl-5'-(1â³-hydroxyallyloxy)biphenyl-2,2'-diol, 5,5'-diallyl-2'-(allyloxy)biphenyl-2-ol, 5,5'-diallyl-2'-(3-methylbut-2-enyloxy)biphenyl-2-ol, (E)-5-allyl-3'-(prop-1-enyl)biphenyl-2,4'-diol, and 4-allyl-2-(2'-methylbenzofuran-5'-yl)phenol, have been isolated from the stem bark of M. officinalis, together with 12 known compounds. Several exhibited inhibition (IC50) values ≤10.7 µM) of superoxide anion generation by human neutrophils in response to fMLP/CB. Others inhibited fMLP/CB-induced elastase release with IC50) values ≤8.76 µM.
Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Lignanas/química , Lignanas/farmacologia , Magnolia/química , Adulto , Células Cultivadas , Humanos , Estrutura Molecular , Adulto JovemRESUMO
Six aporphine alkaloids, (+)-(S)-N-butyrylcaaverine (1), (+)-(S)-N-propionylcaaverine (2), (+)-(S)-N-acetylcaaverine (3), (+)-(6aR,7R)-N-butyrylnorushinsunine (4), (+)-(6aR,7R,E)-N-(but-2-enoyl)norushinsunine (5), and N-formyldehydrocaaverine (6) were isolated from the roots of Illigera luzonensis, together with 16 known compounds. Their structures were determined through spectroscopic and MS analyses. Among the isolates, (-)-deoxypodophyllotoxin (13) was the most cytotoxic, with IC(50) values of 0.0057, 0.0067, 0.00004, and 0.0035µg/mL, respectively, against DLD-1, CCRF-CEM, HL-60, and IMR-32 cell lines. In addition, (-)-yatein (12) exhibited cytotoxic effects, with IC(50) values of 0.81, 0.20, and 0.59µg/mL, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines.