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Objective: To study the chemical constituents and hypoglycemic activity of Phlomis tuberosa. Methods: The db/db diabetic mice was used to screen the hypoglycemic active site of P. tuberosa. The chemical constituents were isolated and purified by various separation and analysis techniques. The structures of these compounds were identified by spectroscopic analysis (1H-, 13C-NMR and MS). The hypoglycemic activities of these compounds were verified by the DPP-4 inhibitory activity in vitro. Results: Ethyl acetate extract of P. tuberosa showed significant hypoglycemic effect. Twenty-five compounds were isolated from the active site, containing β-stiosterol (1), stigmasterol (2), daucosterol (3), clerosterol-stigmast-4-ene-3,6-dione (4), 22-dehydro- stigmast-4-ene-3,6-dione (5), ellagic acid (6), ethyl gallate (7), gllagic acid (8), 4-hydroxybenzoic acid (9), 3,4-diohydroxybenzoic acid (10), cinnamic acid (11), p-hydroxy-cinnamic acid (12), caffeic acid (13), 5-hydromethylfuraldehyde (14), quinic acid (15), chlorogenic acid (16), ferulic (17), 2,3-dimethoxy-5-methyl-6-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaen-1- yl)-2,5-cyclohexadiene-1,4-dione (18), 1-O-caffeoyl- quinic acid (19), 3,5-dimethoxy-4-hydroxy-benzene carbonic-1-O-β-D-glucoside (20), 2-O-butyl-α-D-fructofuranoside (21), n-octadecanoic acid (22), stearic acid (23), methyl-5-(hydroxymethyl) furan-2-carboxylate (24) and 4-hydroxy-3-methoxy-benzaldehyde(25). Nine compounds were obtained from the genus Phlomis for the first time, in which ellagic acid (6), quinic acid (15), and 1-O- caffeoylquinic acid (19) showed strong DPP-4 inhibitory activity with IC50 of 72.3, 89.2, and 103.4 μmol/L, respectively. The IC50 of the positive drug diprotin A was 50 μmol/L. Conclusion: Compounds (3-7 and 18-21) are obtained from the genus Phlomis for the first time. Compound 6, 15, and 19 show DPP-4 inhibitory activities.
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Objective: To study the chemical constituents of Sedum aizoon and to screen the anti-oxidant activities and α-glucosidase inhibitory activities of compounds. Methods: The compounds were separated and purified by various chromatographic techniques, and their structures were identified by physio-chemical properties and EI-MS, ESI-MS, 1H and 13C NMR. The anti-oxidant activity of compounds was screened by DPPH method. The obtained compounds were subjected to detection of α-glucosidase inhibitory activity by PNPG method. Results: Seventeen compounds were isolated from S. aizoon, which were identified as iriflophene (1), kaempferol (2), quercetin (3), myricetin (4), rhamnazin-3-O-β-D-glucopyranoside (5), isolariciresinol-9-O-β-D-glucopyranoside (6),myricitrime (7), myricetin-3-O-α-L-arabinopyranoside (8), iriflophenone-2-O-β-D-glucopyranoside (9), 2-O-(trans-caffeoyl)-malic acid 1-methyl-ester (10), 2-O-(trans-caffeoyl)-malic acid 1,4-dimethyl ester (11), 2-O-(trans-caffeoyl) malic acid (12), p-coumaric acid (13), ethyl gallate (14), butanedioic acid (15), 9(Z)-octadece-namide (16), and lotaustralin (17). Conclusion: Compounds 13 and 15 are isolated from S. aizoon for the first time. Compounds 9-12, and 16 are isolated from genus Sedum for the first time. Compounds 2, 3, 7, 8, 10, 12, and 14 had significant anti-oxidant activity. Compounds 8 showed moderate α-glucosidase inhibitory activity in vitro. Compound 3 showed strong α-glucosidase inhibitory activity in vitro.
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The intestinal absorption properties of four main effective components(gallic acid, ocinolglucoside, ethyl gallate and penta-O-galloyl-β-D-glucose) in Rhus chinensis extracts were investigated by in situ single-pass intestinal perfusion model in rats. The liquid accumulation of perfusion was corrected by gravimetry. The HPLC method was established to determine the concentration of the four effective components in the intestinal perfusion. It showed significant differences(Pethyl gallate>gallic acid>ocinolglucoside, with significant differences between them(P<0.05). In conclusion, gallic acid, orpheolglucoside, ethyl gallate and pentacyl-glucose could be absorbed in the whole intestine. Their absorption rate and permeation ability were related to the intestinal section and the perfusate concentration. These results indicated potential active transport or facilitated diffusion in the intestinal transport process of the four effective components.
Subject(s)
Animals , Rats , Chromatography, High Pressure Liquid , Hydroxybenzoates , Metabolism , Intestinal Absorption , Perfusion , Phytochemicals , Metabolism , Rhus , ChemistryABSTRACT
Objective: To study the chemical constituents in the aerial parts of Triosteum pinnatifidum. Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20, and ODS column chromatography. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments and HR-ESI-MS analyses. Results: Ten compounds were isolated from the aerial parts of T. pinnatifidum, among them there were two monoterpene diglycosides and eight phenols. They were identified as (E)-(6S)-8-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyloxy]-2,6-dimethyloct-2-eno-1,3″-lactone (1), urceolide (2), 2,3-dihydroamentoflavone (3), apigenin-4'-O-β-D-glucoside (4), apigenin-7-O-β-D-glucoside (5), protocatechuic acid (6), ethyl gallate (7), tachioside (8), icariside F2 (9), and icariside E4 (10). Conclusion: All the compounds except compound 2 are isolated from the plants of Triosteum Linn. for the first time. The arabinopyranosyl moiety of compound 1 is revised as 1C4 α-L-arabinopyranose.
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Objective: To study the chemical constituents from the exocarps of Juglans mandshurica which was an anti-tumor herb. Methods: The chemical constituents were isolated from the EtOAc and CHCl3 extracts by solvent extraction, repeated silica gel, Sephadex LH-20 column chromatography, and preparative high performance liquid chromatography. Their structures were elucidated by physicochemical properties and spectral data analysis. Results: Thirteen compounds were identified as 4(R)-ethoxy-8- hydroxy-α-tetralone (1), 4(R)-regiolone (2), ethyl gallate (3), Methyl 4-hydroxyphenylacetate (4), 8-hydroxyl anthraquinone-1- carboxylic acid (5), 4(R),5-dihydroxy-α-tetralone (6), myricanol (7), Juglanin B (8), 5-deoxymyricanone (9), 5-hydroxy-1- (4'-hydroxyphenyl)-7-(4″-hydroxy-3″-methoxyphenyl)-3-heptanone (10), broussonol E (11), Kaempferol-3-O-α-L-rhamnoside (12), quercetin-3-O-α-L-rhamnoside (13). Conclusion: Compounds 3-5, 7, and 9-13 are isolated from the exocarps of J. mandshurica for the first time, and the prenylated flavonoids were firstly reported in this genus.
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Objective: To study the chemical constituents of Phyllanthus urinaria. Methods: Compounds were isolated and purified by the normal phase silica gel, Sephadex LH-20, MCI gel, RP-18, and semi-manufactured preparation HPLC method. Their structures were identified by the methods of 1H-NMR and 13C-NMR combined with physicochemical property. Results: Sixteen compounds were isolated from the petroleum ether and ethyl acetate fraction in 95% ethanol extract of P. urinaria and their structures were gallic acid (1), caffeic acid (2), ethyl gallate (3), methyl gallate (4), 4-ethoxybenzoic acid (5), diisobutyl phthalate (6), dibutyl phthalate (7), (4R,6R)-2,3-dihydromenisdaurilide (8), (4R,6S)-2,3-dihydromenisdaurilide (9), aquilegiolide (10), menisdaurilide (11), cassipourol (12), (9Z,12Z)-nonadeca-9,12-dienoic acid (13), methyl linoleate (14), stigmasterol (15), and (8R,8'S,7S)-4'-(3″- methoxyrhamnopyranosyl) oxy-8'-hydroxy-3,3',4-trimethoxy-8-hydroxymethyl-lign-7-9'-lactone (16). Conclusion: Compounds 5-7, 10, 11, 13, and 14 are isolated from this plant for the first time, and compounds 8, 9, 12, and 16 are first isolated from the plants in genus Phyllanthus L. for the first time.
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OBJECTIVE: To study the effect of ethyl gallate in inducing apoptosis of human colon carcinoma Lovo cells. METHODS: Cultured human colon carcinoma Lovo cells in vitro were used as the research object. Morphological changes of apoptotic cells were observed by inverted microscope.AnnexinV-FITC/PI assay and DNA Ladder assay were performed to study the apoptotic effects. Immunocytochemistry was used to detect the expression of cleaved caspase-9 and cleaved caspase-3 proteins. RESULTS: Ethyl gallate had growth inhibition on colon cancer Lovo cells,the density was decrease: the apoptotic rates were increased with dose increase: Agarose gel electrophoresis showed evident DNA fragmentation: the expression of cleaved caspase-9 and cleaved caspase-3 proteins was increased in treated groups. CONCLUSION: Ethyl gallate could induce the apoptosis in Lovo cells through up-regulating the expression of cleaved caspase-9 and cleaved caspase-3 protein,and then activated the mitochondrial pathway.
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Objective: To study the chemical constituents from Lagotis brevituba. Methods: The chemical constituents were isolated by solvent extraction, repeated silica gel chromatography, and preparative-HPLC. Their structures were elucidated by physicochemical properties and NMR data. Results: Eleven compounds were isolated from the ethyl acetate and n-butanol fraction of L. brevituba and their structures were identified as arvenin I (1), 3,4-dihydroxyphenylethanol (2), bis (2-ethylhexyl) phthalate (3), plantamajoside (4), mannitol (5), ethyl gallate (6), ethyl 3,4-dihydroxybenzoate (7), dibutyl phthalate (8), β-sitosterol (9), acteoside (10), and mussaenosidic acid (11). Conclusion: Compounds 1-3, 6, and 7 are obtained from the plants in Lagotis Gaertn. for the first time. Compounds 4 and 5 are isolated from L. brevituba for the first time.
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Objective: To analyze the six active ingredients in Rhodiola crenulata from the different origins of Qinghai-Tibet Plateau, to establish quantitative analysis methods, and to provide a basis for further use. Methods: Samples were extracted with 30% ethanol; In Diamonsil C18 column (250 mm × 4.6 mm,5 μm), gradient elution was carried out with acetonitrile -0.3% phosphoric acid solution as the mobile phase, detection wavelength 275 nm, and column temperature 25 ℃. Results: A good linear relationships of gallic acid, salidroside, tyrosol, catechin, ethyl gallate, and coumaric acid were at 38.2-382.0 (r = 0.9998), 301.0-3010.0 (r = 0.9999), 19.8 - 198.0 (r = 0.9996), 17.1-171.0 (r = 0.9996), 4.5-45.0 (r = 0.9998), and 6.38-63.80 ng/mL (r = 0.9994), respectively. Conclusion: The method is simple, rapid, accurate, and can be used simultaneously to determine the content of the six active ingredients in R. crenulata from the different origins of Qinghai-Tibet Plateau.
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Objective: To investigate the chemical constituents of Adisia faberi. Methods: Compounds were isolated and purified by the normal phase silica gel, Sephadex LH-20, MCI gel, and ODS-A-HG packing material. Their structures were identified by the methods of MS, 1H-NMR, and 13C-NMR combined with physicochemical property. Results: Eleven compounds were isolated and their structures were elucidateasbauerenol (1), oleic acid (2), (Z)-10-heneicosenoic acid (3), grasshopper ketone (4), bergenin (5), mallonanoside A (6), ethyl gallate (7), astilbin (8), quercitrin (9), ardisiacrispin B (10), and ardicrenin (11). Conclusion: Compounds 2, 7, 9-11 are isolated from this plant for the first time; Compounds 3, 4, 6, and 8 are isolated from plants in genus Ardisia Swartz for the first time.
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Objective To evaluate the effects of ethyl gallate (EG ) on sepsis-induced acute lung injury (ALI) in rats .Methods Forty-eight healthy male Wistar rats ,aged 10-12 weeks ,weighing 150-250 g ,were randomly divided into 3 groups (n=16 each) using a random number table :control group (group C) ,group ALI , and group EG .The animals were anesthetized with intraperitoneal pentobarbital sodium 50 mg/kg .Sepsis was induced by cecal ligation and puncture (CLP) .EG 1 ml/h (50 mg·kg-1 ·h-1 ) was infused intravenously via the femoral vein for 4 h starting from 6 h after CLP in group EG .The equal volume of normal saline was given instead in group ALI . The rats were sacrificed at 10 and 24 h after CLP (T1 ,2 ) , and the lungs were removed for determination of wet/dry lung weight ratio (W/D ratio ) , superoxide dismutase (SOD ) activity , contents of malondialdehyde (MDA ) and glutathione (GSH ) , and 3-NT expression (by immuno-histochemistry ) in lung tissues .The pathological changes of the lung were examined with light microscope .Results Compared with group C ,the W/D ratio ,MDA content and 3-NT expression were significantly increased and GSH content was decreased at T1 ,2 ,the SOD activity was significantly decreased at T2 in group ALI ,and the MDA content and 3-NT expression were increased at T1 ,and the W/D ratio ,MDA content and 3-NT expression were increased and GSH content was decreased at T2 in group EG ( P<0.05) .Compared with group ALI ,the MDA content was significantly decreased at T1 ,and the W/D ratio ,MDA content and 3-NT expression were decreased ,and GSH content and SOD activity were increased at T2 in group EG ( P<0.05) .The pathological changes of the lung were obvious in group ALI , and significantly attenuated in group EG .Conclusion EG can attenuate sepsis-induced ALI by antioxidative effects in rats .