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Objective: To investigate the chemical constituents from Pogonatum inflexum. Methods: The constituents were separated by column chromatographic methods of silica gel, Sephadex LH-20 column chromatography and liquid phase preparation, and the structure of the compounds was identified by comparing the physicochemical properties of the compounds with the spectral data. Results: A total of 16 compounds were obtained from P. inflexum, which were identified as tricin (1), irisflorentin (2), 3,5,4'-trihydroxy-7,3'-dimethoxyflavone (3), 3,5,3'-trihydroxy-7,4'-dimethoxyflavanone (4), 5,2'-dihydroxy-6,7-methylenedioxy- flavanone (5), 5,2',3'-trihydroxy-6,7-methylenedioxyflavanone (6), apigenin (7), kaempferol (8), kaempferide (9), naringenin (10), quercetin (11), baicalein (12), luteolin (13), protocatechuic aldehyde (14), 4-hydroxy-3-methoxy-benzaldehyde (15), and 2-hydroxy-5-(2-hydroxy-4- methoxybenzyl)-4-methoxybenzaldehyde (16). Conclusion: All compounds are isolated from the genus Pogonatum for the first time, among them, dihydroflavones may be the characteristic components of this genus.
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Objective: To study the chemical constituents of the rhizomes of Schoenoplectus tabernaemontani. Methods: Compounds were isolated and purified by a combination of column chromatography including silica gel, polyamide and Sephadex LH-20. Their structures were elucidated by physiochemical properties and NMR analysis. Results: Twelve compounds were obtained from water extract of the rhizome of S. tabernaemontani and identified as 5,7,2',4'-tetrahydroxy-3, 5'-dimethoxyflavone (1), tricin (2), hesperetin (3), quercetin (4), luteolin (5), eriodictyol (6), apigenin (7), naringenin (8), chrysin (9), 5,7-dihydroxychromone (10), catechin (11) and tricin-7-O-β-D-glucoside (12), respectively. Conclusion: Compound 1 is a new flavone named schoenin. Compounds 2-5 and 7-12 are isolated from the Cyperaceae for the first time. Compound 6 is isolated from the genus Scirpus for the first time.
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Objective: To study the chemical constituents from the green walnut husks of Juglans mandshurica. Methods: The chemical constituents from the green walnut husks of J. mandshurica were isolated and purified by repeated silica gel, Sephadex LH-20 column chromatography and ODS column chromatography, and their structures were identified by NMR spectral analysis. Results: A total of 14 compounds were isolated from the green walnut husks of J. mandshurica, and identified as apigenin (1), tricin (2), eupatilin (3), 3,7,8,3’-tetrahydroxy-4’-methoxyflavone (4), 3,5-dihydroxy-7-methoxy-3’,4-methylenedioxyflavone (5), taxifolin (6), quercetin-3-O-(6″-galloyl)-β-D-galactopyranoside (7), quercetin-3-O-(4″-O-acetyl)-α-L-rhamnopyranoside (8), engeletin (9), isoengeletin (10), kaempferol-3-O-β-D-glucopyranoside (11), quercetin-3-O-β-D-glucuronide (12), quercetin-3-O-β-D- glucopyranoside (13), and myricetin-3-O-β-D-glucuronide (14). Conclusion: Compounds 1-10, 12, and 14 are isolated from the green walnut husks of J. mandshurica for the first time.
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Objective: To study the chemical constituents of the stems and leaves of semi-mangrove plant, Barringtonia racemosa. Methods: The chemical constituents of B. racemosa were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies and preparative HPLC. Their structures were identified by physicochemical properties, spectroscopic analysis, as well as comparisons with the data reported in literature. Results: A total of 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of B. racemosa, which were identified as chrysin (1), ayanin (2), genkwanin (3), rhamnocitrin (4), tricin (5), dillenetin (6), 5,3'-dihydroxy-7,4'-dimethoxyflavone (7), 5,7,3',4'-tetramethoxyflavone (8), 5-hydroxy-6,7,8,3',4'- pentamethoxy flavone (9), petasitolone (10), sarmentol F (11), dehydrovomifoliol (12), blumenol A (13), 10-hydroxyaristolan-9-one (14), alphitolic acid (15), oleanolic lactone (16), and 11,12-dehydroursolic acid lactone (17). Conclusion: All compounds are isolated from the genus Barringtonia for the first time.
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SUMMARY The preferential solvation parameters of tricin in {ethanol (1) + water (2)} binary mixtures were obtained from their thermodynamic properties by means of the inverse Kirkwood-Buff integrals method. Tricin is very sensitive to specific solvation effects, so the preferential solvation parameter by ethanol (1), δx 1,3 is negative in the water-rich mixtures but positive in all the other compositions at temperatures from 293.15, to 313.15 K. It is conjecturable that in water-rich mixtures the hydrophobic hydration around the aromatic and methyl groups of the drug plays a relevant role in the solvation. The higher drug solvation by ethanol in mixtures of similar solvent proportions and in ethanol-rich mixtures could be due mainly to polarity effects. In these mixtures, the drug would be acting as Lewis acid with the ethanol molecules because this co-solvent is more basic than water.
RESUMEN Los parámetros de solvatación preferencial del tricina en mezclas {etanol (1) + agua (2)} se obtuvieron a partir de las propiedades termodinámicas de solución, mediante el método de las integrales inversas de Kirkwood-Buff. La tricina es muy sensible a los efectos de solvatación específicos, por lo que el parámetro de solvatación preferencial, δx 1,3 es negativo en las mezclas ricas en agua, pero positivo en todas las otras composiciones a temperaturas desde 293,15 hasta 313,15 K. Se puede establecer que en mezclas ricas en agua la hidratación hidrofóbica alrededor de los grupos aromáticos y metilo del fármaco tiene un papel relevante en la solvatación. La mayor solvatación del fármaco por etanol se presenta en mezclas de proporción intermedia y en mezclas ricas en etanol, esto podría deberse principalmente a los efectos de la polaridad. En estas mezclas, el fármaco actuaría como ácido de Lewis con las moléculas de etanol, puesto que este codisolvente es más básico que el agua.
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AIM To observe the inhibitory effects of tricin on the airway inflammation in low concentration LPS induced asthma mice.METHODS The model of asthma mice with airway inflammation was induced by low concentration LPS plus OVA.There were four groups:blank control group,asthma model group,tricin treatment group and dexamethasone (positive drug) treatment group.The levels of inflammatory factors,including NO,TNF-α and IL-1β,in bronchoalveolar lavage fluid (BALF) were detected by ELISA;the pathology of lung tissue was observed by HE staining;the mRNA and protein expressions of TLR4,MyD88 and NF-κB p65 in alveolar macrophages were detected using real-time quantitative PCR (RT-PCR) and Western blot.RESULTS Tricin could significantly decrease the levels of NO,TNF-α and IL-1β in BALF of asthma mice and improve lung inflammation.It could also down-regulate the relative mRNA and protein expressions of TLR4,MyD88 and NF-κB p65.CONCLUSION Tricin has inhibitory effects on airway inflammation in asthma mice,whose mechanism may be related to the intervention of TLR4/MyD88/NF-κB pathway.
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Objective: To study the chemical constituents from Polygonum multiflorum. Methods: The constituents were isolated and purified by macroporous adsorbent resin (DM-8), gel chromatography, silica chromatography, and other modern separation methods, and the structures were identified by spectral analyses. Results: Ten compounds were isolated and identified as thunberginol C 6-O-β-D-glucopyranoside (1), p-hydroxybenzaldehyde (2), trans-N-caffeoyltyramine (3), (Z)-2,3,5,4'-tetrahydroxy-stilbene-2-O-β-D- glucoside (4), (E)-2,3,5,4'-tetrahydroxy-stilbene-2-O-β-D-glucoside (5), pieceid-2″-O-gallate (6), (E)-2,3,5,4'-tetrahydroxystilbene-2-O-β-D-(3″-galloyl)-glucoside (7), tricin-7-O-β-D-glucoside (8), torachrysone-8-O-β-D-glucoside (9), and emodin-8-O-β-D-glucoside (10). Conclusion: Compound 1 is a new compound named as polygonimitin D. Compounds 3 and 8 are isolated from this plant for the first time.
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Objective To study the chemical constituents from the leaves of Cyclocarya paliurus. Methods The compounds were isolated and purified by chromatographic techniques and their structures were identified on the basis of spectral features. Results Forteen known compounds, including 11 flavonoids and three phenolic acids, named kaempferol (1), quercetin (2), apigenin (3), tricin (4), eupatilin (5), 3,7,8,3'-tetrahydroxy-4'-methoxyflavone (6), myricetin (7), 3,5-dihydroxy-7-methoxy-3',4'-methylenedioxyflavone (8), isoquercitrin (9), quercetin-3-O-β-D-glucuronide (10), myricetin-3-O-β-D-glucuronide (11), caffeic acid (12), 5-caffeoylquinic acid (13), and 3-hydroxybenzoic acid-4-O-β-D-glucopyranoside (14) were isolated from the leaves of C. paliurus. Conclusion Compounds 3, 4, 5, and 14 are firstly obtained from C. paliurus. Compounds 6 and 8 are isolated from the genus of Cyclocarya for the first time. Compounds 1-11 showed moderate active against the brine shrimp larvae, and compounds 12-14 indicated significant growth inhibitory activity against the brine shrimp (Artemia salina) larvae.
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We previously reported that treatment with tricin (4’,5,7-trihydroxy-3’,5’-dimethoxyflavone) after human cytomegalovirus (HCMV) infection significantly suppressed both infectious virus production and HCMV replication in human embryonic lung fibroblast (HEL) cells. Moreover, we recently revealed that HCMV infection can increase the expression of CC-motif ligand 2 (CCL2/MCP-1) and CCR2, a specific receptor for CCL2, which can enhance HCMV infection and replication, in turn. In this study, we examined whether CCL2 and/or CCR2 are involved in the anti-HCMV effects of tricin in HEL cells. Exposure of fibroblasts to tricin inhibited infectious HCMV production, with concomitant decreases in CCL2 and CCR2 transcript levels and CCL2 protein levels in a dose-dependent manner. Propagermanium, an inhibitor of CCR2 function, has also been shown to inhibit infectious HCMV production with concomitant decreases in CCL2 protein levels. We further observed that tricin and propagermanium reduced mRNA expression of HCMV immediate early gene and DNA polymerase in a dose-dependent manner. These results suggest that tricin is a novel anti-inflammatory compound with potential anti-HCMV activity, and CCL2/CCR2 interactions are associated with HCMV replication.
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Objective: To study the chemical constituents from the aerial parts of Fagopyrum dibotrys. Methods: The compounds were isolated and purified by means of chromatographic techniques and their structures were identified on the basis of spectral features. Results: Fourteen known compounds were isolated in the methanol extract from the aerial parts of F. dibotrys and their structures were identified as benzoic acid (1), p-hydroxybenzoic acid (2), p-hydroxy benzaldehyde (3), 3,4-dihydroxy benzoic acid (4), succinic acid (5), caffeic acid (6), methyl caffeate acid (7), luteolin (8), tricin (9), quercetin (10), afzelin A (11), 2α,3β,29-trihydroxyolean-12-en-28-oic acid (12), yarumic acid (13), and 3α-hydroxy-urs-12,15-dien (14). Conclusion: Compounds 2-3 and 6-9 are firstly obtained from the aerial parts of F. dibotrys. Compounds 11-14 are isolated from the genus of Fagopyrum Mill. for the first time.
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Objective: To investigate the chemical constituents from the leaves of Ananas comosus and their biological activities. Methods: The chemical constituents from the air-dried leaves of A. comosus were isolated and purified by the chromatography on silica gel and Sephadex LH-20 columns as well as recrystallization. Their structures were identified on the basis of physiochemical properties and spectroscopic data analyses, and the antibacterial activity and artemia lethal activity of the compounds were determined. Results: Eight compounds were isolated from the 95% ethanol extract in the leaves of A. comosus and identified as tricin-4′-O-[10″-O-(8″-hydroxyl) feruloyl-(9‴-O-p-coumaroyl) glyceryl] ether (1), 2, 4-dichlorobenzoic acid (2), tricin (3), chrysoeriol (4), 1-O-p-coumaroylglycerol (5), 1-O-feruloylglycerol (6), 1-O-feruloyl-3-O-p-coumaroyl-glycerol (7), and 1, 3-O-diferuloylglycerol (8). Compound 1 exhibited as well inhibitory activities as positive control Ciprofloxacin (CPFX) against Staphylococcus aureus and Escherichia coli, with MIC values of 0.156 μg/mL. The results of artemia lethal activity showed that the IC50 of the compounds 1 and 4 were 21.4 and 25.0 μg/mL, respectively. Conclusion: All the compounds except 5 are isolated from this plant for the first time. Among them, compound 1 is a new one and named ananasin A, which has the good antibacterial and artemia lethal activity.
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Objective To study the chemical constituents from Leucas ciliata. Methods Silica gel, RP-18, and Sephadex LH-2O column chromatography techniques were used for separation and purification of the compounds and extensive spectral analysis spectrum were employed for structural elucidation. Results Twelve compounds were isolated from ethanol extract of L. ciliata and identified as tricin (1), crisilineol (2), sitosterol-3-O-glucoside (3), stigmast-5-ene-11-ol- 3-O-β-glucoside (4), 5, 7-dimethoxy-2-methyl-4-chromanone (5), 3', 5', 5, 7-tetramethoxy-4'-O-β-glucoside flavone (6), 5-hydroxy-3', 4'-dimethoxy-7-O-β-glucoside flavone (7), acteoside (8), 3, 4-dihydroxy-β-phenylethoxy-O-ααrabinopyranosyl-(l""- →2")α-Z,-rhamnopyranosyl-(r"-→3") -4"-O-caffeoylβ-D-glucopyranoside (9), 3-hydroxy-4-methoxy-β- phenylethoxy-Oα-Lαrabinopyranosyl-(l""-→6") α-L-rhamnopyranosyl-(r"-→3")4"-O-caffeoyl-β-D- glucopyranoside (10), leucasin A (11A), and leucasin B (11B). Conclusion Compounds 11A and 11B are epimers and new compounds, and the other ten compounds are obtained from the plants of Leucas R. Br. for the first time.
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Objective: To establish a separation method of tricin reference substance from Bambusa textilis. Methods: After extracted with ethyl acetate, the extract of B. textilis was isolated and purified by silica gel column chromatography and preparative HPLC. Tricins were identified by melting point, UV, and IR spectroscopy. Results: The content of tricin was over 98% by normalization method of HPLC. Conclusion: The developed method is simple with lower cost, by which tricin can be used as reference substances for the qualitative and quantitative analyses of Chinese herbal medicine.
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Objective To study the constituents of Salsola collina.Methods The chemical constituents were isolated and purified by various chromatographic methods and their structures were elucidated by analyses of spectral data and physicochemical properties.Results Three compounds were isolated and identified as tricin-7-O-?-D-apiosyl(1→2)-?-D-glucopyranoside(Ⅰ),tianshic acid(Ⅱ),and n-hentriacontanol (Ⅲ).Conclusion CompoundⅠis a new compound named collinoside,compoundⅡis isolated from S.collina for the first time.
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Objective To develop an HPLC method for the quantitative analysis of tricin in malt. Methods HPLC method was used. Analysis was performed on Spherigel C_ 18 column (150 mm?4.6 mm, 5 ?m) with acetonitrile-water-tetrahydrofuran-methanoic acid (26∶74∶10∶1) as mobile phase. The detection wavelength was 350 nm, flow rate was 1.0 mL/min, and the analysic volumn was set at 20 ?L. Results The calibration curve of tricin was linear in the range of 0.22-2.15 mg/L (r=0.999 8). The average recovery rate of tricin was 97.4% (RSD=1.7%) (n=9). Conclusion The method can be used to determine tricin in raw malt quantitatively.