RESUMO
Twenty five known aromatic glycosides (1-25) and three known sesquiterpene glycosides (26-28) have been isolated from the twigs of Litsea cubeba by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis (MS, IR, 1D and 2D NMR) as (7S,8R)-dehydrodiconiferyl alcohol 4,9'-di-O-ß-D-glucopyranoside(1),(7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(2), (7S,8R)-urolignoside(3), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranoside(4), saposide B(5), lanicepside A(6), matairesinol-4-O-ß-D-glucopyranoside (7), tyraxjaponoside B(8), (+)-lyoniresinol-9'-O-ß-D-glucopyranoside (9), alaschanisoside A (10), syringin (11), psoralenoside (12), isopsoralenoside (13), scopolin(14), 2,6-dimethoxy-4-hydroxyphenol-1-O-ß-D-glucopyranoside (15), 3-hydroxy-4,5-dimethoxyphenyl-ß-D-glucopyranoside (16), 2-(3,4-dihydroxyphenyl)ethyl-ß-D-glucopyrnoside (17), 2-(4-dihydroxyphenyl)ethyl-ß-D-glucopyranoside (18), (+)-catechin-7-O-ß-D-glucopyranoside (19), 3'-O-methylepicatechin-7-O-ß-D-glucopyranoside (20), kaempferitrin (21), quercetin-3-O-α-L-rhamnopyranside (22), kaempferol-3-O-ß-D-glucopyranoside (23), kaempferol 3-O-ß-D-glucopyranosyl(1â2)-O-ß-D-galactopyr anoside-7-O-α-L-rhamnopyranoside (24), quercetin 3-O-α-L-rhamnopyranosyl(1â6)-O-ß-D-glucopyranosyl(1â3)-O-α-L-rhamnopyranosyl(1â2)-O-ß-D-glucopyranoside (25), staphylionoside D(26), vomifoliol 9-O-ß-D-glucopyranoside (27), dihydrovomifoliol-O-ß-D-glucopyranoside (28). Compounds 1-21 and 24-28 were obtained from this genus for the first time.
Assuntos
Medicamentos de Ervas Chinesas , Glicosídeos/isolamento & purificação , Litsea/química , Compostos Fitoquímicos/isolamento & purificação , Cromatografia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , ÁguaRESUMO
Sixteen lignanoids were isolated from an aqueous extract of the commonly used Chinese traditional medicine Dangshen, the dried roots of Codonopsis pilosula, by using a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, MCI resin, sephadex LH-20, and reversed phase semi-preparative HPLC. On the basis of spectral data analysis, their structures were elucidated and identified asï¼-ï¼-ï¼7R,7'R,8R,8'Sï¼-4,4'-dihydroxy-3,3',5,5',7-pentamethoxy-2,7'-cyclolignaneï¼1ï¼,ï¼-ï¼-ï¼7R,8Sï¼- dihydrodehydrodiconiferyl alcohol 4-O-ß-D-glucopyranosyl-ï¼1'''â2''ï¼-ß-D-glucopyranosideï¼2ï¼,ï¼-ï¼-ï¼7R,8Sï¼- dihydrodehydrodiconiferyl alcoholï¼3ï¼,ï¼+ï¼-ï¼7S,8Rï¼-dehydrodiconiferyl alcoholï¼4ï¼,ï¼+ï¼-balanophoninï¼5ï¼,ï¼+ï¼- demethoxypinoresinolï¼6ï¼,ï¼+ï¼-pinoresinolï¼7ï¼,ï¼+ï¼-epipinoresinolï¼8ï¼,ï¼-ï¼-syringaresinolï¼9ï¼,ï¼-ï¼-medioresinolï¼10ï¼,ï¼-ï¼-lariciresinolï¼11ï¼,ï¼-ï¼-secoisolariciresinolï¼12ï¼,ï¼-ï¼-ent-isolariciresinolï¼13ï¼,ï¼+ï¼-ï¼7S,8Sï¼-3-methoxy-3',7- expoxy-8,4'-neolignan-4,9,9'-triolï¼14ï¼,ï¼+ï¼-ï¼7S,8Rï¼-3',4-dihydroxy-3-methoxy-8,4'-neolignanï¼15ï¼, andï¼-ï¼-ï¼7R,8Rï¼-3',4-dihydroxy-3-methoxy-8,4'-neolignanï¼16ï¼. All these compounds were isolated from C. pilosula for the first time, while compound 1 is a new natural product of 2,7'-cyclolignan and 2 is a new 4',7-epoxy- 8,3'-neolignan diglucoside. Compound 12 showed activity against Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation with an inhibition ratio ofï¼63.4 ± 8.3ï¼ % at 1×10(-5) mol·L(-1).
Assuntos
Codonopsis/química , Medicamentos de Ervas Chinesas/química , Extratos Vegetais/química , Raízes de Plantas/química , Animais , Butileno Glicóis , Furanos , Lignanas , Microssomos Hepáticos/efeitos dos fármacos , Estrutura Molecular , RatosRESUMO
Two new phenylpropanoids(1 and 2), together with thirteen known compounds(3-15), have been isolated from the root of Paeonia lactiflora by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis(MS,IR,1D and 2D NMR)as(+)-(7R,8R)-1-guaiacyl-1,2-propanediolacetonide(1),(-)-(7R,8S)-1-guaiacyl-1,2-propanediolacetonide(2),O-senecioyllomatin(3),O-angeloyllomatin(4),(+)-cis-3'-senecioyloxy-4'-angeloyloxy-3',4'-dihydroseselin(5),columbianadin(6), benzyl 2,5-dihydroxybenzoate(7),3,6-dimethyl-5-hydroxyBenzo-furan(8),(S)-evofolin-A(9),2,3-dihydroxy-4-methoxyacetophenone(10), 2,5-dihydroxy-4-methoxyacetophenone(11), 2,5-dihydroxy-4-methyl acetophenone(12),ethyl 4-hydroxybenzoate(13), vanillic acid(14),and 4-hydroxy-3-methoxybenzaldehyde(15).Compounds 1 and 2 were new compounds,and compounds 3-9 were obtained from the genus Paeonia for the first time.
Assuntos
Paeonia/química , Extratos Vegetais/química , Raízes de Plantas/química , Acetatos , Acetofenonas , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificaçãoRESUMO
Using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, 115 compounds including diterpenes, sesquiterpenes, treterpenes, coumarins, lignans, fatty acid derivatives, and simple aromatic derivatives were isolated from an ethanol extract of branch of Fraxinus sieboldiana (Oleaceaue), and their structures of the compounds were elucidated by spectroscopic methods including 1 D, 2D NMR and MS techniques. Among them, 41 compounds were new. In previous reports, we have been described the isolation, structure elucidation, and bioactivities of the 41 new compounds and 22 known orii including 8 coumarins, 4 phenolic and 12 phenylethanoidal glycosides. As a consequence, we herein reported the isolation and structure elucidation of the remaining 50 known compounds including 8- hydroxy-12-oxoabieta-9(11),13-dien-20-oic 8, 20-lactone(1), 6beta-hydroxyfcrruginol(2),(+)-pisiferic acid(3), (+)-pisiferal(4),(+)-7-dehydroabiet6none(5), 1-oxomiltirone(6), subdigitatone(7), linarionoside B(8), (9S)-linarionoside B(9), (3R,9R)-3-hydroxy-7,8-dihydro-beta-ionol 9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside(10), ursolic acid(11), betulinic acid(12), euscaphic acid(13), (+)-syringaresinol(14), (+)-fraxiresinol(15), (+)-1-hydroxysyringaresinol(16), pinoresinol(17), medioresinol(18), 8-acetoxypinoresinol(19), epipinoresinol(20), (-)-olivil(21), (+)-cyclo-olivil(22), 3,3'-dimethoxy-4,4',9-trihydroxy-7,9'-epoxylignan-7'-one(23),(+)-1-hydroxypinoresinol 4'-O-beta-D-glucopyranoside (24), (+)-1-hydroxypinoresinol 4"-O-beta-D-glucopyranoside(25),(+)-syringaresinol O-beta-D-glucopyranoside (26), liriodendrin (27), ehletianol D(28), icariside E5(29) (-)-(7R, 8R)-threo-1-C-syringylglycerol(30),(-)-(7R, 8S)-erythro-guaiacylglycerol (31),(-)-(7R, 8R)-threo-guaiacylglycerol(32), 3-(4-beta-D-glucopyranosyloxy-3-methoxy)-phenyl-2E-propenol(33),2,3-dihydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(34), 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (35), 3-hydroxy-l-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(36), omega-hydroxypropioguaiacone(37), sinapyladehyde(38), trans-p-hydroxycinnamaldehyde(39), syringic acid(40), vanilic acid(41), vanillin(42), 4-hydroxy-benzaldehyde (43), (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol(44), beta-sitosterol(45), daucosterol(46), 2,6-dimethoxy-I,4-benzoquinone(47), 2,6-dimethoxy-pyran-4-one(48), 1-(beta-D-ribofuranosyl)uracil(49), and mannitol(50). Compouds 1-7,12,18,28-37,44 and 48 were obtained from the genus Fraxinus for the first time.
Assuntos
Fraxinus/química , Extratos Vegetais/análise , Espectroscopia de Ressonância Magnética , Espectrometria de MassasRESUMO
Ten glycosidic compounds were isolated from an ethanol extract of Machilus wangchiana by a combination of various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase flash chromatography and HPLC. Their structures were identified by spectroscopic data analysis (IR, MS, and NMR) as icariside B1 (1), boscialin-3-O-ß-D-glucopyranoside (2), pisumionoside (3), isolariciresinol-9'-O-ß-D-xylopyranoside (4), 5'-methoxyisolariciresinol-9'-O-ß-D-xylopyranoside (5), lyoniresinol-9'-O-ß-D-xylopyranoside (6), (E) -4-hydroxyphenylprop-7-ene 4-O-ß-D-glucopyranoside (7), (E) - 4-hydroxy-3-methoxyphenylprop-7-ene 4-O-α-L-rhamnopyranosyl-(1 --> 6) -ß-D-glucopyranoside (8), 4-hydroxy-3-methoxyphenylprop-8-ene 4-O-ß-D-xylopyraosyl-(1 --> 6) -ß-D-glucopyranoside (9), and 4-hydroxy-3,5-dimethoxyphenylprop-8-ene 4-O-α-L-rhamnpyranosyl-(1 --> 6)-ß-D- glucopyranoside (10), respectively.
Assuntos
Medicamentos de Ervas Chinesas/química , Glicosídeos/química , Lauraceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
From an aqueous extract of Lonicera japonica flower buds, sixteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as 6'-O-acetylvogeloside (1), 6'-O-acetylsecoxyloganin (2), dichlorogelignate (3), guanosinyl-(3' --> 5')-adenosine monophosphate(GpA,4) , 5'-O-methyladenosine (5), 2'-O-methyladenosine (6), adenosine (7), syringin (8), methyl 4-O-ß-D-glucopyranosyl caffeate (9), (-)-dihydrophaseic acid 4'-O-ß-D-glucopyranoside (10), ketologanin (11), 7α-morroniside (12), 7ß-morroniside (13), kingiside (14), cryptochlorogenic acid methyl ester (15), and 6-hydroxymethyl-3-pyridinol (16). All the compounds were obtained from this plant for the first time, compounds 1 and 2 are new compounds, 3 and 5 are new natural products, and 4 is the first example of dinucleoside monophosphate isolated from a plant extract.
Assuntos
Medicamentos de Ervas Chinesas/química , Flores/química , Lonicera/química , Cromatografia Líquida de Alta Pressão , Medicamentos de Ervas Chinesas/isolamento & purificação , Espectrometria de Massas , Estrutura MolecularRESUMO
Eighteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as adinoside A (1), stryspinoside (2), benzyl alcohol beta-glucopyranoside (3), benzyl 2-o-beta-D-glucopyranosyl-2,6-dihydroxybenzoate (4) , gentisic acid 2-O-beta-D-glucopyranoside (5), eugenyl beta-D-glucopyranoside (6) , eugenyl-P-xylopyranosyl-(1-->6)-beta-glucopyranoside (7), (-)-lyoniresinol 9-O-fP-D-glucopyranoside (8) , (+)-lyoniresinol 9-O-beta-D-glucopyranoside (9) , apigenin-7-O-L-rhamnopyranoside (10), luteolin-3 '-O-L-rhamnoside (11) , ursolic acid (12) , beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (13), abscisic acid (14), guanosine (15), 5-methyluracil (16), trans-cinnamic acid (17), and 4-hydroxybenzaldehyde(18). These compounds were obtained from this plant for the first time.
Assuntos
Flores/química , Lonicera/química , Benzaldeídos/análise , Gentisatos/análise , Glucosídeos/análise , Hidroxibenzoatos/análise , Luteolina/análise , Timina/análise , Triterpenos/análise , Ácido UrsólicoRESUMO
A new compound (1), together with ten known compounds (2-11), have been isolated from the branch of Litsea greenmaniana by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis as N-trans-3, 4-methylenecinnamoyl-3-methoxytyramine (1), N-trans-feruloyltyramine (2), N-cis-feruloyltyramine (3), (+)-sesamin (4), (+)-pinoresinol(5), cinnamophilin (6), dihydrodehydrodiconiferyl alcohol (7), benzoic acid (8), 4-hydroxy ethylbenzoate (9), p-hydroxybenzaldehyde(10), and 4-hydroxy-3-methoxy-benzyl alcohol (11). Compound 1 was a new compound, and compounds 2-11 were obtained from this plant for the first time.
Assuntos
Medicamentos de Ervas Chinesas/química , Litsea/química , Espectrometria de Massas , Estrutura MolecularRESUMO
Ten compounds were isolated from the 70% ethanol extract of linseed meal (Linum usitatissimum L) through a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. On the basis of spectroscopic data analysis, they were elucidated as 1-methylethyl-2-O-beta-D-glucopyranosyl-(1" --> 6')-beta-D-glucopyanoside (1), linustatin (2), neolinustatin (3), lotaustralin (4), linamarin (5), deoxyguanosine (6), deoxyadenosine (7), (+)-pinoresinol-4'-O-beta-D-glucopyranoside (8), 4-O-beta-D-glucopyranosylvanillyl alcohol (9) and tachioside (10), separately. Among them, compound 1 is a new compound, and compounds 6, 8 and 10 were isolated from the linseed meal for the first time.
Assuntos
Linho/química , Plantas Medicinais/química , Amigdalina/análogos & derivados , Amigdalina/química , Amigdalina/isolamento & purificação , Desoxiadenosinas/química , Desoxiadenosinas/isolamento & purificação , Desoxiguanosina/química , Desoxiguanosina/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glicosídeos/química , Glicosídeos/isolamento & purificação , Lignanas/química , Lignanas/isolamento & purificação , Estrutura Molecular , Nitrilas/química , Nitrilas/isolamento & purificação , Sementes/químicaRESUMO
A new dihydroflavonol glycoside dimer 6,6-bisastilbin (1) and a new nitrile-containing metabolite (Z)-5α,6ß-dihydroxy-4ß-methoxy-2-cyclohexene-Δ(1,α)-acetonitrile (2), together with three known analogs, bauhinin, bauhinilide, and dehydrodicatechin A, have been isolated from an ethanol extract of Bauhinia aurea. Their structures were determined by spectroscopic and chemical methods.
Assuntos
Bauhinia/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Flavonóis/química , Flavonóis/isolamento & purificação , Glicosídeos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Glicosídeos/química , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/químicaRESUMO
Five new phenylpropene diglycosides (1-5), together with three known analogs, have been isolated from an ethanol extract of the bark of Machilus wangchiana. Their structures were determined by spectroscopic and chemical methods. In the preliminary assay, compounds 2 and 5-8 reduced dl-galactosamine (GalN)-induced hepatocyte (WB-F344 cells) damage with 37-41% inhibitions at 10 µM.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lauraceae/química , Propiofenonas/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Hepatócitos/efeitos dos fármacos , Estrutura Molecular , Casca de Planta/química , Propiofenonas/química , Propiofenonas/farmacologiaRESUMO
Six new butanolide derivatives with long aliphatic side chains (1-6), together with 23 known lipophilic constituents, were isolated from the bark of Machilus yaoshansis. Their structures were elucidated by spectroscopic and chemical methods. All the isolates were evaluated for cytotoxic and anti-inflammatory activities.
Assuntos
4-Butirolactona/análogos & derivados , 4-Butirolactona/isolamento & purificação , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Lauraceae/química , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Fator de Necrose Tumoral alfa/antagonistas & inibidoresRESUMO
Nine new fatty acid derivatives, including seven methoxylated (1, 2, and 4-8) and two hydroxylated (3 and 9) fatty acids, have been isolated from the ethanol extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. The 3- or 9-methoxylated fatty acids are reported for the first time in nature.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Ácidos Graxos/isolamento & purificação , Fraxinus/química , Medicamentos de Ervas Chinesas/química , Ácidos Graxos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Caules de Planta/químicaRESUMO
Four new minor constituents including two cyclodipeptides (1 and 2) and two cyclopentene derivatives (3 and 4), together with four known cyclodipeptides, have been isolated from an ethanolic extract of the tubers of Gymnadenia conopsea. Their structures including absolute configurations were determined by spectroscopic data interpretation combined with chemical methods. Among them, compound 1 contains an abnormal S-(4''-hydroxybenzyl)cysteine residue, 3 and 4 possess [(4-methylcyclopentyl)methyl]benzene and (4-hydroxymethylcyclopentyl)benzene carbon skeletons, respectively, both of which are first found from the natural source.
Assuntos
Ciclopentanos/isolamento & purificação , Peptídeos Cíclicos/isolamento & purificação , Ciclopentanos/química , Medicamentos de Ervas Chinesas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Orchidaceae/química , Peptídeos Cíclicos/química , Tubérculos/químicaRESUMO
By using a combination of various chromatographic techniques including column chromatography over silica gel and Pharmadex LH-20 and reversed-phase HPLC, two minor new compounds, labda-12, 14-dien-6beta, 7alpha, 8beta, 17-tetraol (1), 2, 3-cis-6-acetyl-5-hydroxy-2-(hydroxymethylvinyl)-2, 3-dihydrobenzofuran-3-ol angelate (2), and a minor new natural product 6-methoxy-4-methyl-3, 4-dihydro-2H-naphthalen-1-one (3) have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures were elucidated with spectroscopic data analysis including 2D NMR experiments.
Assuntos
Aster/química , Benzofuranos/isolamento & purificação , Diterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Naftalenos/isolamento & purificação , Benzofuranos/química , Diterpenos/química , Medicamentos de Ervas Chinesas/química , Naftalenos/química , Plantas Medicinais/químicaRESUMO
Two new triterpenoids taraxer-14-ene-1alpha,3beta-diol (1) and 3beta-hydroxytaraxer-14-ene-1-one (2), together with the known triterpenes taraxerol (3), betulin (4), betulinic acid (5), sumaresinolic acid (6), and 5-hydroxy-2-methoxy-1,4-naphthoquinone (7), 5,7-dihydroxy-6,8-dimethylchromone (8), alpha-monpalmitin (9), palmitic acid (10), 6beta-hydroxystigmast-4-en-3-one (11), beta-sitostero1 (12), have been isolated from the petroleum ether fraction of the ethanolic extract of Pterospermum heterophyllum. Their structures were established by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-8 were evaluated against several human cancer cell lines. Compound 1 showed in vitro selective cytotoxicity against human lung cancer cell lines (A549) with an IC(50) value of 1.22 microM. Compound 7 showed significant cytotoxicity against the A549, HCT-8, Bel7402, BGC-823, and A2780 cancer cell lines with IC(50) values of 0.21, 0.55, 0.40, 0.59, and 0.34 microM, respectively. However, the other compounds were inactive (IC(50)>10 microM).
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Malvaceae/química , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Feminino , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Palmítico/química , Triterpenos Pentacíclicos , Raízes de Plantas/química , Sitosteroides/química , Sitosteroides/isolamento & purificação , Estereoisomerismo , Terpenos , Triterpenos/química , Triterpenos/farmacologia , Ácido BetulínicoRESUMO
OBJECTIVE: To investigate the chemical constituents from the branch of Fraxinus sieboldiana, and evaluate their antioxidative activity. METHOD: The chemical constituents were isolated and purified by chromatographic techniques over silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. Structures of the compounds were identified by spectroscopic methods. The antioxidant activity was evaluated by Fe(+2)-cystine induced rat liver microsomal lipid peroxidation. RESULT: Eight coumarins were obtained and their structures were elucidated as esculin (1) , esculetin (2), fraxin (3), fraxetin (4), 6, 7-di-O-beta-D-glucopyranosylesculetin (5), scopoletin (6), cleomiscosin D (7) and cleomiscosin B (8). At a concentration of 10(-6) mol x L(-1), compound 4 showed antioxidative activity inhibiting Fe(+2)-cystine induced rat liver microsomal lipid peroxidation with inhibitory rate of 60%. CONCLUSION: Compounds 5, 7 and 8 were obtained from the genus Fraxinus for the first time. Compound 4 showed remarkable antioxidative activity, which was higher than that of VE (35%).
Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Fraxinus/química , Peroxidação de Lipídeos/efeitos dos fármacos , Microssomos Hepáticos/efeitos dos fármacos , Animais , Cumarínicos/química , Cumarínicos/farmacologia , Espectroscopia de Ressonância Magnética , Microssomos Hepáticos/metabolismo , Ratos , Escopoletina/química , Escopoletina/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Umbeliferonas/química , Umbeliferonas/farmacologiaRESUMO
OBJECTIVE: To investigate the chemical constituents of the brach of Macaranga adenantha, and evaluate their TNF-alpha inhibitory activity. METHOD: The chemical conshifuents were isolated and purified by chromatographic methods. Structures of the compounds were identified by spectroscopic methods. The TNF-alpha secretion inhibitory activity of the mouse peritoneal macrophages was evaluated by MTT methods. RESULT: Ten compounds were isolated and their structures were identified as: cleomiscosin A (1), cleomiscosin B (2), ellagic acid 4-O-alpha-D-rhamnopyranside (3), ellagic acid 4-O-beta-D-xylopyranoside (4), vanillic acid (5), (24R) -stigmast-4-en-3-one (6), (24R) -stigmast-3, 6-dione (7), (24R) -6beta-hydroxy-stigmast-4-en-3-one (8), daucosterol (9), beta-sitosteryl glucoside-6'-O-heptadecoicate (10). At a concentration of 10 micromol x L(-1), compounds 1, 3 and 4 showed inhibitory activity to TNF-alpha secretion of the mouse peritoneal macrophages with the inhibitory rates of 57.0%, 64.4%, and 57. 4%, respectively. CONCLUSION: All compounds were isolated from genus Macaranga for the first time. Compounds 1, 3, and 4 were active against TNF-alpha secretion of the mouse peritoneal macrophages.
Assuntos
Cumarínicos/isolamento & purificação , Ácido Elágico/análogos & derivados , Euphorbiaceae/química , Fator de Necrose Tumoral alfa/metabolismo , Animais , Sobrevivência Celular/efeitos dos fármacos , Cumarínicos/química , Cumarínicos/farmacologia , Ácido Elágico/química , Ácido Elágico/isolamento & purificação , Ácido Elágico/farmacologia , Macrófagos Peritoneais/citologia , Macrófagos Peritoneais/efeitos dos fármacos , Macrófagos Peritoneais/metabolismo , Camundongos , Caules de Planta/química , Plantas Medicinais/químicaRESUMO
OBJECTIVE: To study the chemical constitutes of Acantophora spicifera. METHOD: Compounds were isolated by normal phase silica gel and Sephadex LH-20 gel column chromatography, and reverse-phase HPLC, as well as recrystallization. Their structures were elucidated by spectroscopic methods. RESULT: Seven compounds were isolated from A. spicifera and their structures were identified as aplysin (1), loloilide (2), (R)-(-)-dehydrovomifoliol (3), uracil (4), thymine (5), 1-methoxy-4-(1-propenyl) benzene (6). CONCLUSION: The compounds were obtained from this genus for the first time. Compound 6 was firstly obtained from marine organisms.
Assuntos
Rodófitas/química , Rodófitas/isolamento & purificação , Estirenos/isolamento & purificação , Cromatografia/métodos , Cromatografia Líquida de Alta Pressão/métodos , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Estirenos/química , Timina/química , Timina/isolamento & purificação , Uracila/química , Uracila/isolamento & purificaçãoRESUMO
OBJECTIVE: To study the chemical constituents of Bauhinia aurea. METHOD: The compounds were isolated by column chromatography over silica gel, reversed-phase RP-18, and Sephadex LH -20. MS and NMR spectroscopic methods were used to determine structures of purified compounds. RESULT: Eight compounds were isolated from the ethyl acetate soluble fraction of the ethanolic extract and their structures were elucidated as isoengeletin (1), astilbin (2), neoastilbin (3), isoastilbin (4), neoisoastilbin (5), (+)-catechin (6), (-)-epicatechin (7) and (-)-epicatechin 3-O-gallate (8). CONCLUSION: Five compounds were isolated from this genus for the first time except for 2, 6 and 8.