RESUMO
Artemdubosides A-E (1-5), the first examples of natural polyacetylenes substituted by 6'-O-crotonyl ß-glucopyranoside, and artemdubosides F-G (6-7) that were two unusual polyacetylenes featuring a 6'-O-acetyl ß-glucopyranoside moiety, were isolated from Artemisia dubia var. subdigitata. Their structures were elucidated based on the spectral data including HRESIMS, UV, IR, 1D and 2D NMR, and ECD calculations. Antihepatoma assay suggested that compound 1 exhibited activity against HepG2, Huh7, and SK-Hep-1 cells with inhibitory ratios of 77.1%, 90.8%, and 73.1% at 200.0 µM, respectively.
Assuntos
Artemisia , Compostos Fitoquímicos , Artemisia/química , Humanos , Estrutura Molecular , Linhagem Celular Tumoral , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Poli-Inos/farmacologia , Poli-Inos/isolamento & purificação , Poli-Inos/química , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , ChinaRESUMO
5-Hydroxytryptamine 2C (5-HT) receptor is one of the major targets of anti-obesity agents, due to its role in regulation of appetite. In the present study, the 70% EtOH extract of the roots of Bupleurum chinense was revealed to have agonistic activity on 5-HT receptor, and the subsequent bioassay-guided isolation led to identification of several saikosaponins as the active constituents with 5-HT receptor agonistic activity in vitro and anti-obesity activity in vivo. The new compound, 22-oxosaikosaponin d (1), was determined by extensive spectroscopic analyses (HR-ESI-MS, IR, and 1D and 2D NMR). The primary structure-activity relationship study suggested that the intramolecular ether bond between C-13 and C-28 and the number of sugars at C-3 position were closely related to the 5-HT receptor agonistic activity. Saikosaponin a (3), the main saponin in B. chinense, showed obviously agonistic activity on 5-HT receptor with an EC value of 21.08 ± 0.33 μmol·Lin vitro and could reduce food intake by 39.1% and 69.2%, and weight gain by 13.6% and 16.4%, respectively, at 3.0 and 6.0 mg·kgin vivo. This investigation provided valuable information for the potential use of B. chinense as anti-obesity agent.
Assuntos
Animais , Masculino , Ratos , Fármacos Antiobesidade , Química , Farmacologia , Bioensaio , Bupleurum , Química , Ácido Oleanólico , Química , Farmacologia , Ratos Sprague-Dawley , Saponinas , Química , Farmacologia , Agonistas do Receptor 5-HT2 de Serotonina , Química , Farmacologia , Relação Estrutura-AtividadeRESUMO
Thirteen compounds were isolated from the ethyl acetate extract of the rhizomes of Cyperus rotundus(Xiangfu) by means of various chromatographic techniques(silica gel, Al2O3, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were identified as cyperotundic acid(1),(4S, 5E, 10R)-7-oxo-trinoreudesm-5-en-4β-ol(2), 4-hydroxy-4, 7-dimethyl-1-tetralone(3), taraxerone(4), dammaradienyl acetate(5), zeorin(6), sarmentine(7), guineensine(8), pellitorine(9), caprolactam(10), liriodendrin(11), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2,6-dimethoxyphenoxy]propyl-β-D-glucopyranoside(12)and 1-(3, 4-methylenedioxyphenyl)-1E-tetradecene(13) by extensive spectroscopic analyses(IR, MS, 1D-and 2D-NMR). Compound 1 was a new rearranged sesquiterpene and named as cyperotundic acid, which did not obey the isoprene rule.Compounds 2-13 were obtained from the genus Cyperus for the first time.
RESUMO
In this paper, the chemical constituents and bioactivities of leaves of Nicotiana tabacum were investigated. Six compounds were isolated by means of various chromatographic techniques (silica gel, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were elucidated as cis-5'-(2-oxopropyl)-nicotine (1), 3-O-(9, 12, 15-octadecatrienoyl)-glyceryl-β-D-galactppyranoside (2), (l'R, 2R, 5S, 10R)-2-(1', 2'-dihydroxy-l'-methylethyl)-6, 10-dimethylspiro [4, 5] dec-6-en-8-one (3), (l'S, 2R, 5S, l0R)-2-(1', 2'-dihydroxy-l'-methylethyl)-6, 10-dimethylspiro [4, 5] dec-6-en-8-one (4),2, 3-dihydroxypropyl-β-D-galactoside (5) and phenylethyl β-D-glucopyranoside (6) by extensive spectroscopic analyses (UV, IR, MS, 1D- and 2D-NMR). Among them, compound 1 is a new alkaloid, and compounds 2-6 are isolated for the first time from N. tabacum. Compounds 1 and 2 were assayed for agitating activities on transient receptor potential vanilloid 1 (TRPV1), melatonin receptor 1 and 2 (MT1 and MT2), 1 showed agitating rate of 55.41% (1.53mmol•L⁻¹) on MT2 and 2 possessed agitating rate of 128.11% (0.59 mmol•L⁻¹) and 52.00% (0.73mmol•L⁻¹) on TRPV1 and MT1, respectively.
RESUMO
Fifteen known compounds were isolated from Swertia delavayi by silica gel, Sephadex LH-20 and Rp-18 column chromatographies. Based on extensive spectroscopic analysis (MS, 1H, 13C-NMR), their structures were identified aserythrocentaurin (1), erythrocentaurindimethylacetal (2), sweroside (3), swertiamarin (4), gentiopicroside (5), swertiakoside A (6), 2'-O-acetylswertiamarin (7), 4'-O-[(Z) -coumaroyl] swertiamarin (8), 1,5,8-trihydroxy-3-methoxyxanthone (9), 8-O-β-D-glucopyranosyl-1-hydroxy-2,3, 5-trimethoxyxanthone (10), 8-O-[β-D-xyl- opyranosyl-(1 --> 6)-β-D-glucopyranosyl]-7,8-dihydroxy-3-methoxyxanthone (11), isovitexin (12), β-sitosterol (13), daucosterol (14), and oleanolic acid (15). Among them, ten ones (14, 7-11, 13) were obtained from S. delavayi for the first time. The isolates were evaluated for their anti-HBV activities in HepG 2. 2. 15 cell line in vitro. The results showed that compound 1, 2, 6, 7, 9 and 12 exhibited significant inhibitory activity on HBV DNA replication with IC50 values from 0.05 to 1.46 mmol x L(-1).
Assuntos
Antivirais , Química , Medicamentos de Ervas Chinesas , Química , Vírus da Hepatite B , Genética , Imageamento por Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Swertia , QuímicaRESUMO
The ethyl acetate extract of the flower of Albizia julibrissin was isolated and purified by silica gel, Sephadex LH-20 and MCI GEL CHP-20P column chromatography to yield 29 compounds. Their structures were elucidated as 8-hydroxy-2, 6-dimethyl-2E, 6Z-octadienoic acid (1), 8-O-formyl-2, 6-dimethyl-2E, 6Z-octadienoic acid (la), 8-hydroxy-2, 6-dimethyl-2E, 6E-octadienoic acid (2), 8-O-formyl-2, 6-dimethyl-2E, 6E-octadienoic acid (2a), (2E, 6S)-2, 6-dimethyl-6-O-beta-D-xylpyranosyloxy-2, 7-menthia-folic acid (3), clovan-2beta, 9alpha-diol (4), 2beta-O-formyl-clovan-9alpha-ol (4a), 2beta, 9alpha-O-diformyl-clovan (4b), vomifoliol (5), (6S, 9R)-roseoside (6), vanillin (7), 4-O-ethylgallic acid (8), 3-ethoxy4-hydroxy-benzoic acid (9), p-hydroxybenzaldehyde (10), gallic acid (11), protocatechoic acid (12), stearic acid (13), palmitic acid (14), 2, 3-dihydroxypropyl hexadecanoate (15), linoleic acid (16), scopoletin (17), indole-3-carboxaldehyde (18), 2-furoic acid (19), 5-(hydroxymethyl)-2-furaldehyde (20), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3beta-ol (21), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 9, 22-trien-3beta-ol (22), (+)-lariciresinol 9'-stearate (23), formononetin (24) and uridine (25). Compounds 1a, 2a, 4a and 4b were new artifacts from the separation process, and others were obtained from A. julibrissin for the first time.
Assuntos
Albizzia , Química , Medicamentos de Ervas Chinesas , Química , Flores , Química , Biologia Celular , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Five compounds were isolated from Capsicum annuum by means of various chromatographic techniques (silica gel, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were determined as luteolin-7-O-[2"-O-(5"-O-sinapoyl)-beta-D-apiofuranosyl]-beta-D-glucopyranoside (1), uridine (2), adenosine (3), 7-hydroxy-6-methoxy cinnamic acid ethyl ester (4) and 7-hydroxy cinnamic acid ethyl ester (5) by extensive spectroscopic analyses (UV, IR, MS, 1D- and 2D-NMR). Among them, compound 1 is a new flavone glycoside named as capsicuoside A, and cmpounds 2-5 are isolated for the first time from the fruits of C. annuum.
Assuntos
Capsicum , Química , Flavonas , Química , Frutas , Química , Glucosídeos , QuímicaRESUMO
<p><b>OBJECTIVE</b>To study the chemical constituents of Oxytropis falcate.</p><p><b>METHOD</b>The air-dried whole plants of O. falcate were extracted with EtOH (90%) three times at room temperature. The compounds were isolated by silica-gel, polyamide, C-18 and Sphadex LH-20 columns. The structures were identified based on spectral elucidation.</p><p><b>RESULT</b>Fourteen compounds were isolated from O. falcate and identified as, (-)-7-methoxy-dihydroflavone (1), (-)-5-hydroxy-7-methyoxy-dihydroflavone (2), (-)-pinocembrin (3), (-)-7-hydroxy-dihydroflavone (4), 4'-methoxy-2'-hydroxy-chalcone (5), 2', 4'-dihydroxy-dihydrochalcone (6), 2',4'-dihydroxy-chalcone (7), (-)-maackiain (8), tetrahydroflemichapparin-B (9), dalbergin (10), N-benzoyl-2-phenylethylamine (11), n-tetracosanol (12), rhamnocitrin-3-O-beta-neohesperidoside (13), beta-sitosterol (14).</p><p><b>CONCLUSION</b>All the compounds were isolated from O. falcate for the first time.</p>
Assuntos
Cromatografia , Medicamentos de Ervas Chinesas , Química , Etanol , Química , Oxytropis , Química , TemperaturaRESUMO
<p><b>OBJECTIVE</b>To study alkaloid constituents of Diploclisia affinis.</p><p><b>METHOD</b>The air-dried vine stems of D. affinis were extracted with 90% EtOH three times at room temperature. The EtOH extract was suspended in H2 O and adjusted to pH 2 with 5% HCl solution. After extracted with petroleum ether and CHCl3 successively, the aqueous fraction was adjusted to pH 9 with 10% NH3 x H2O and extracted with CHCl3 again to afford the total alkaloids fraction. The compounds were isolated through column chromatography from the total alkaloids fraction. Their structures were determined on the basis of spectral analysis (MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>Five alkaloids was identified as reticuline (1), asimilobine (2), acutumine (3), dihydroxyprotoberberine (4), stepholidine (5), were isolated from the vine stems of D. affinis.</p><p><b>CONCLUSION</b>All the compounds were obtained from D. affinis for the first time.</p>
Assuntos
Alcaloides , Química , Aporfinas , Química , Benzilisoquinolinas , Química , Berberina , Química , Medicamentos de Ervas Chinesas , Química , Etanol , Química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Menispermaceae , Química , Caules de Planta , Química , Compostos de Espiro , QuímicaRESUMO
<p><b>OBJECTIVE</b>To study the chemical constituents of Swertia mileensis.</p><p><b>METHOD</b>The air-dried whole plants of S. mileensis were extracted with 50% EtOH. The EtOH extract was suspended in H20 and extracted with petroleum ether, CHCl3 and n-BuOH successively. The compounds were isolated and purified by column chromatography from the CHCl3 fraction, and identified based on spectral analyses (MS, H-NMR, 13C-NMR).</p><p><b>RESULT</b>Twelve compounds were isolated from S. mileensis, and were elucidated as 1,5, 8-trihydroxy-3-methoxyxanthone (1), 1-hydroxyl-2, 3, 5, 7-tetramethoxyxanthone (2), 1-hydroxyl-3, 5, 8-trimethoxyxanthone (3), 1-hydroxyl-2, 3, 4, 6-tetramethoxyxanthone (4), 1-hydroxyl-2, 3, 4, 7-tetramethoxyxanthone (5), 1,8-dihydroxy-3, 5-dimethoxyxanthone (6), 1, 7-dihydroxy-3, 8-dimethoxyxanthone (7), 1, 3, 5, 8-tetrahydroxyxanthone (8), balanophonin (9), oleanolic acid (10), maslinic acid (11), sumaresinolic acid (12).</p><p><b>CONCLUSION</b>Compounds 1, 3, 7-9, 11 and 12 were obtained from S. mileensis for the first time.</p>
Assuntos
Medicamentos de Ervas Chinesas , Química , Swertia , QuímicaRESUMO
<p><b>OBJECTIVE</b>To study the chemical constituents of Oxytropis chiliophylla.</p><p><b>METHOD</b>The air-dried whole plants of O. chiliophylla were extracted with EtOH (90%) three times at room temperature. The compounds were isolated by silica-gel, polyamide, C-18 and Sphadex LH -20 columns. The structures were identified based on spectral analysis.</p><p><b>RESULT</b>8 compounds were isolated from O. chiliophylla and identified as azukisapogenol (1), (22E, 24R) -24-methyl-5alpha-cholesta-7, 22-diene-3beta, 5alpha, 6beta-triol (2), apigein (3), 3', 4'-dimethoxy-quercetin-3-O-beta-D-galactopyranoside (4), 7, 3', 4'-trimethoxy-quercetin-3-O-alpha-L-rhamopyranosyl-(1-->2)-beta-D-glucopyranoside (5), (2S, 3S, 4R)-N-[(R)-2'-hydroxytetracosanoyl]-1, 3, 4-trihydroxy-2-amino-octadeca-6-ene (6), beta-sitosterol (7), daucosterol (8).</p><p><b>CONCLUSION</b>All the compounds were isolated from O. chiliophylla for the first time.</p>
Assuntos
Oxytropis , Química , Plantas Medicinais , Química , Sapogeninas , Química , Sitosteroides , QuímicaRESUMO
<p><b>OBJECTIVE</b>To study chemical constitutents of the rhizomes of Ligusticum chuanxiong.</p><p><b>METHOD</b>The rhizomes of L. chuanxiong were extracted with water to afford a water extract which was participated between H2O and EtOAc, n-BuOH, successively. The compounds were isolatedand purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses.</p><p><b>RESULT</b>Eleven compounds were isolated from the rhizomes of L. chuanxiong, and structures were characterized as (4S)-p-menth-1-ene4, 7-diol (1), aromadendrane-4alpha, 10beta-diol (2), aromadendrane-4beta, 10alpha-diol (3), aromadendrane-4beta, 10beta-diol (4), augustic acid (5), xiongterpene (6), pregnenolone (7), 3(R), 8(S), 9(Z)-falcarindiol (8), senkyunolide F (9), senkyunolide I (10), 4-hydroxyl-3-butylphthalide (11).</p><p><b>CONCLUSION</b>Compounds 1-5 were obtained from the rhizomes of L. chuanxiong for the first time.</p>
Assuntos
Ligusticum , Química , Ácido Oleanólico , Química , Plantas Medicinais , Química , Pregnenolona , Química , Rizoma , Química , Terpenos , QuímicaRESUMO
Objective To observe changes of luteinizing hormone (LH), follicle-stimulating hormone (FSH) and testosterone (T) in umbilical vein blood between male and female neonates, and assess the effect of serum LH, FSH and T on fetal growth.Methods Umbilical vein blood was obtained from 130 neonates (64 females and 66 males) in the second hospital of changshu city. According to birth weight, 130 neonates were divided into 3 groups: macrosomia (n=28), intrauterine growth restriction (IUGR) (n=31) and normal neonates (n=71). The serum levels of LH, FSH and T were measured by radioimmunoassay.Results 1.The levels of LH, FSH and T in umbilical vein blood were significantly higher in male neonates than those in females (P
RESUMO
<p><b>AIM</b>The anti-gastric ulcer constituents from the roots of Crepis napifera (Franch) Babc (Compositae) were studied.</p><p><b>METHODS</b>Solvent partition, Si gel and Rp-18 column chromatography, crystallization and spectral methods were used to extract, isolate and identify two compounds. The activity of compound 1 was tested on the rat stomach by determining the effect on aspirin-induced gastric lesions and on histamine-stimulated gastric acid secretion.</p><p><b>RESULTS</b>Two sesquiterpene lactone glycosides, taraxinic acid-1'-O-beta-D-glucopyranoside (1) and 11,13-dihydro-taraxinic acid-1'-O-beta-D-glucopyranoside (2) were obtained. Compound 1 at the dose of 80 mg.kg-1 p.o. inhibited significantly the development of aspirin-induced gastric lesions in the rat and at an i.v. dose of 70 mg.kg-1 did not affect histamine-stimulated gastric acid secretion in the lumen-perfused rat stomach.</p><p><b>CONCLUSION</b>Compound 1 is the active component of the plant which protects gastric mucosa and exhibits anti-gastric ulcer action.</p>