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Objective: To investigate the effects of syringic acid on HEK 293 and HepG2 cells in the absence and presence of exogenous Cu (II) and Fe (II) ions. Methods: The antiproliferative effects of syringic acid on HEK 293 and HepG2 cells in the absence and presence of exogenous Cu (II) and Fe (II) ions were examined by MTT assay. Additionally, colony-forming, reactive oxidative species (ROS) generation, apoptosis induction, autophagy, mitochondrial membrane potential, and mitochondrial mass were investigated. Results: At 24 and 72 h, no significant differences were observed in the viability of HepG2 cells between the control and syringic acid + Fe (II) groups. However, exposure of HepG2 cells to syringic acid + Cu (II) for 72 h reduced the cell viability significantly. Furthermore, ROS formation, induction of apoptosis, and autophagic vacuoles were significantly increased in HepG2 cells without marked changes in mitochondrial membrane potential and mitochondrial mass. Moreover, syringic acid + Cu (II) reduced the plating efficiency and surviving fraction significantly. Conclusions: The combination of syringic acid with Cu (II) was toxic to cancer cells and showed pro-oxidant activity. In addition, this combination induced autophagy in cancer cells with less cytotoxic effects on normal cells, which is a potential candidate for the development of novel therapeutics towards cancer.
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Objective: To determine the effects of syringic acid on hepatic damage in diabetic rats.Methods: Diabetes was induced by streptozotocin. Diabetic rats were given syringic acid at doses of 25, 50 and 100 mg/kg by oral gavage for 6 weeks. Syringic acid effects on the liver were evaluated by examination of plasma biochemical parameters, and pathological study. In addition, biomarkers of lipid peroxidation and antioxidant status of liver tissues were assessed. Real time-PCR was performed to investigate the mRNA expression levels of mitochondrial biogenesis indices in different groups. Results: Syringic acid significantly attenuated the increase in most of plasma biochemical parameters in diabetic rats. Moreover, syringic acid treatment increased the catalase activity while it reduced the superoxide dismutase activity and hepatic malondialdehyde level in diabetic rats. There was no difference between the glutathione content of the treated and untreated groups. These findings were supported by alleviation of histopathological damages in the syringic acid-treated groups compared to the untreated diabetic group. Syringic acid also significantly up-regulated the hepatic mRNA expression of PGC-1α, NRF-1, and NRF-2 and increased the mtDNA/nDNA ratio in diabetic rats. Conclusions: Syringic acid can be considered as a suitable candidate against hepatic complications since it can reduce oxidative damages in diabetic cases. Furthermore, it has the potential of targeting hepatic mitochondria in diabetes.
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Objective: To study the chemical constituents of the Eupatorium adenophorum. Methods: The chemical constituents were isolated and purified by silica gel chromatography repeatedly from the ethyl acetate extract of E. adenophorum, and their structures were identified by spectral analysis and chemical methods. Results: Fourteen compounds were isolated from E. adenophorum and identified as p-hydroxybenzoic acid ethyl ester (1), (1R,4R)-8aα-hydroxy-1-isopropyl-4,7-dimethyl- 1,2,3,4,6,8a-hexahydro-naphthalene-2,6-dione (2), daedalin A (3), 10-oxo-7-hydroxy-nordehydrotremetone (4), caffeoyl acetate (5), syringic acid (6), 3-hydroxy-4-(1-oxo-ethane)-benzoic acid (7), ferulic acid (8), p-hydroxyphenylethyl alcohol (9), protocatechuic acid ethyl ester (10), 4-hydroxy-3-isopropyl benzoic acid (11), balanophonin (12), indole-3-carboxylic acid (13), and 6-methoxy kaempferol (14). Conclusion: Compound 11 is obtained from natural products for the first time, compounds 1, 3, 6, 7, 9, 10, 12-14 are obtained from this genus for the first time, and compound 5 is obtained from this plant for the first time.
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Objective: The present study was carried out to investigate the in vitro anti-inflammatory activity of syringic acid (SA). Methods: SA was tested for it's in vitro anti-inflammatory activity at different concentrations in protein denaturation, proteinase inhibition and human red blood cell (HRBC) membrane stabilization assay. The reference drugs used were aspirin and diclofenac sodium. Results: SA showed concentration-dependent inhibition of protein denaturation and proteinase activity with a half-maximal inhibitory concentration (IC50) value of 49.38±0.56 µg/ml and 53.73±0.27 µg/ml respectively. Heat-induced haemolysis was inhibited by SA with an IC50 value of 57.13±0.24 µg/ml. SA also inhibited the hypotonicity-induced haemolysis (IC50 value of 53.87±0.72 µg/ml). Conclusion: From the present study, we can conclude that SA possesses appreciable anti-inflammatory effect against denaturation of proteins, proteinase activity, and human red blood membrane stabilization assays. Further studies are required for determining the possible mechanisms behind its anti-inflammatory action.
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Objective: To study the chemical constituents of Bidens parviflora. Methods: The ethyl acetate fraction of 80% ethanol extract from B. parviflora was isolated and purified by silica, polyamide, Sephadex LH-20, and HPLC, then the structures of obtained compounds were identified by physicochemical properties and spectral data. Results: Ten compounds were isolated and identified as Z-6-O-(4″-O-acetyl-6″-O-p-coumaroyl-β-D-glucopyranosyl)-6,7,3’,4’-tetrahydroxyaurone (1), okanin-4’-O-β-D-(6″-O- acetyl)-glucoside (2), Z-6-O-(4″,6″-diacetyl-β-D-)-7,3’,4’-tetrahydroxy aurone (3), 6,7,3’,4’-tetrahydroxy aurone (4), isookanin (5), syringic acid-4-O-α-L-rhamnopyranoside (6), okanin-4’-O-β-D-(6″-trans-p-coumaroyl)-glucoside (7), okanin-4’-O-β-D-(4″-acetyl- 6″-trans-p-coumaroyl)-glucoside (8), quercetin-3,4’-dimethyl ether-7-O-rutinoside (9), and cordifolioidyne B (10). Conclusion: Compound 1 is a new compound named as bidenoside I, compounds 6 and 10 are isolated from the genus Bidens for the first time, other compounds are isolated from this plant for the first time.
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Objective To study the chemical constituents of the rhizome of Sinacalia tangutica. Methods The constituents were isolated and purified by silica gel, polyamide column chromatography, Sephadex LH-20, and ODS column chromatography. Their structures were elucidated by NMR spectra comparison with reference data. Results Fourteen phenolic compounds were isolated from the rhizome of S. tangutica, which were identified as hydrangetin (1), 7-hydroxy-coumarin (2), syringic acid (3), 4-hydroxy-3,5-dimethoxybenzaldehyde (4), 3,4-dihydroxybenzaldehyde (5), 4-hydroxybenzaldehyde (6), caffeic acid (7), p-hydroxycinnamic acid (8), ferulic acid (9), methyl 4-O-caffeoyl quinate (10), methyl 5-O-caffeoyl quinate (11), ethyl 5-O-caffeoyl quinate (12), methyl 4,5-di-O-caffeoyl quinate (13), and methyl 3,5-di-O-caffeoyl quinate (14). Conclusion Compounds 3-5, 7-14 are isolated from the genus of Sinacalia for the first time.
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Objective: To establish a HPLC fingerprint method for assessing the quality of Dendrobium huoshanense, in addition to determining concentrations of syringic acid, rutin, dendrophenol and naringenin in this crude drug. Methods: Agilent C18 column (250 mm × 4.6 mm, 5 μm) was utilized with the mobile phase comprising methanol-0.1% phosphoric acid with the flow rate of 1 mL/min in a gradient elution manner. The detection wavelength was set at 240 nm and the column temperature was 30 ℃. The resultant chromatograms were imported to Similarity Evaluation System for Chromatographic Fingerprint of Chinese Materia Medica (2012.1) to obtain retention time and peak area of samples. Similarity for 39 sets of samples were analyzed. The peak area data were processed by SPSS software for cluster analysis and the clustering effect was discussed. Results: The line relationship of this way was good (R > 0.999), with high precision regarding instrument used (RSD < 3.00%), the method showed good reproducibility (RSD < 3.00%), standard recovery was between 99.26% and 100.32% (RSD of 0.35%-1.67%). Different growth period and different planting patterns of D. huoshanense were distinct regarding the concentration of four compounds. Conclusion: The method is useful to evaluate and discriminate D. huoshanense at different growth period for the purpose of providing scientific reference on harvest, development and evaluation of D. huoshanense.
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Objective: To investigate the chemical constituents of Mallotus conspurcatus. Methods: The ethyl acetate part of 75% ethanol extracts from M. conspurcatus was separated through chromatographic techniques. The isolates were identified on the basis of 1H-NMR, 13C-NMR, and ESI-MS data. Results: Eighteen known compounds were isolated. They were 1,5-dihydroxy-3-methoxy-7- methyl-anthraquinon (1), (-)-syringaresinol (2), 2,3-dihydro-5,7-dihydroxy-2,8-dimethyl-6-(3-methyl-2-butenyl)-4H-1-benzo-4-one (3), 2,3-dihydro-5,7-dihydroxy-2,6,8-tri-methyl-4H-1-benzopyran-4-one (4), paeoveitol B (5), pinellic acid (6), trans-p- hydroxycinnamic acid (7), trans-p-methoxycinnamic acid (8), trans-p-hydroxy-ethyl cinnamate (9), p-hydroxybenzoic acid (10), 3-methoxy-4-hydroxybenzoic acid (11), 3,4-dihydroxybenzoic acid (12), ferulic acid (13), syringic acid (14), syringic acid ethyl ester (15), hexadecanoic acid 2,3-dihydroxy-propyl ester (16), galic acid (17), and ethyl gallate (18). Conclusion: Besides compounds 3, 4, and 13, the other compounds are isolated from the plants of Mallotus Lour. for the first time.
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Objective To study the chemical constituents of Glechoma longituba. Methods Chemical constituents were extracted by organic solvents, isolated and purified by chromatographic techniques with silica gel, Sephadex LH-20, semi-preparative HPLC, and recrystallization. Their structures were elucidated on the basis of physiochemical and spectral analyses. Results Thirteen compounds were obtained and elucidated as ursolic acid (1), asoleanolic acid (2), protocatechualdehyde (3), betulic acid (4), luteolin (5), β-sitosterol (6), lutin (7), syringic acid (8), 4-acetoxy-3,5-dimethoxybenzoicacid (9), 2,5-dihydroxy-1,4-benzenedicarboxylic acid (10), (E)-3-[4-(carboxymethoxy)-3-methoxyphenyl] acrylic acid (11), emodin (12), and loliolide (13). Conclusion Compounds 8-10 and 12 are isolated from this plant for the first time. Compounds 11 and 13 are isolated from the plants of Glechoma Linn. for the first time.
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Objective: To investigate the chemical constituents of Swertia chirayita. Methods: Column chromatography, such as silica gel, MCI, Sephadex LH-20 were used to isolate and purify the compounds. Physicochemical properties and spectroscopic methods were used to elucidate their structures. Results: Twelve compounds, including 2 xanthones, 4 triterpenoids, 3 secoiridoids, and 3 other compounds, the chemical constituents were isolated from the ethyl acetate fraction from 85% ethanol extract of S. chirayita, and identified as bellidifolin (1), norbellidifolin (2), oleanolic acid (3), 4-epi-hederagenin (4), 2-epi-corosolic acid (5), ursolic acid (6), amarogentin (7), swerimilegenin I (8), erythrocentaurin (9), pyrocatechol (10), syringic acid (11), and 4-hydroxy-3-methoxybenzoic acid (12). Conclusion: Compounds 4, 5, and 11 are isolated from genus Swertia for the first time, compounds 8 and 9 are found from S. chirayita for the first time.
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OBJECTIVE: To study the chemical constituents of the fruits of Embelia laeta. METHODS: The compounds were isolated and purified by MCI, medium pressure TLC on silica gel column, ODS column chromatography, semi-preparative HPLC, and so on. The structures were elucidated on the basis of various modern spectroscopic techniques using physical, chemical properties and spectral data. RESULTS: Fifteen compounds were isolated and identified as nantenine(1), oxonantenine(2), physcion(3), syringic acid(4), vanillic acid(5), stigmast-4-ene-3,6-dione(6), (+)-lyoniresinol(7), 75,85-threo-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan(8), 1,3-dihydroxylpropyl-(9Z,12Z)-octadeca-9,12-dienate(9),(22E)-5a,8a-epidioxyergosta-6,22-dien-3b-ol(10), dihydroxyisoechinulin A(ll), hydroxybenzoic acid(12), stigmasterol(13), sitosterol(14), and daucosterol(15). CONCLUSION: Compounds 1,2, and 5-13 are isolated from the genus Embelia for the first time, and compounds 1-15 are isolated from this plant for the first time.
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BACKGROUND: Zanthoxylum heitzii is a spice used to prepare several dishes and to treat tumors, syphilis, malaria, cardiac palpitations, urogenital infections in the west region of Cameroon, but the antitumor mechanisms and chemical composition are not yet investigated. This study was aimed to determine the antiproliferative effects of four extracts from the fruits and barks of Zanthoxyllum heitzii (Rutaceae) on apoptosis in human promyelocytic cells, their mechanisms and the chemical composition. The 3-(4, 5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was used to determine the fifty percent inhibition (IC50) concentration of the cell lines after treatment. The effect on morphology was observed using a light or fluorescence microscopy. The rate of apoptosis and the cell cycle were measured using flow cytometry (FCM). The phytochemical analysis of the extract was carried with HPLC/MS methods. RESULTS: The phytochemical analysis of the extracts indicated the presence of four known polyphenols (Syringic acid, Juglon, Luteolin and Myricetin) in both fruits and barks of Z. heitzii but in different quantities. Syringic acid and Myricetin concentrations were between 17-21 fold higher in the fruits than the stem bark. Rhamnetin (393.35 µg/mL) and Oleuropein (63.10 µg/mL) were identified only in the stem barks of Z. heitzii. Among the four extracts tested for cytotoxicity properties, only the methanol extract of fruits and barks significantly inhibited cell proliferation of HL-60 cells with IC50 value of 20 µg/mL and 12 µg/mL respectively. HL-60 cells treated with Z. heitzii extracts significantly produced reactive oxygen species (ROS) with concurrent loss of mitochondrial membrane potential (MMP). Modifications in the DNA distribution and enhanced of G1/G0 phase cell cycle arrest were observed in a concentration dependent manner. CONCLUSIONS: Polyphenols from Z. heitzii plant exert inhibitory effect on HL-60 cells through the reactive oxygen species (ROS) generation, loss of mitochondrial membrane potential and cell cycle destabilization.
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Humans , Apoptosis/drug effects , Plant Bark/chemistry , Zanthoxylum/chemistry , G1 Phase Cell Cycle Checkpoints/drug effects , Fruit/chemistry , Mitochondria/physiology , Mass Spectrometry , Tetrazolium Salts , Thiazoles , Cameroon , Plant Extracts/isolation & purification , Plant Extracts/chemistry , Chromatography, High Pressure Liquid , Spices/analysis , Reactive Oxygen Species/analysis , HL-60 Cells , Inhibitory Concentration 50 , Cell Proliferation/drug effects , Membrane Potential, Mitochondrial/drug effects , Polyphenols/analysis , Flow Cytometry , Microscopy, FluorescenceABSTRACT
Objective: To study the chemical constituents from the roots of Sambucus williamsii. Methods: Silica gel, ODS, and preparative HPLC were used to isolate the compounds. Their chemical structures were elucidated on the basis of spectral data. Results: Eighteen compounds were isolated, and they were identified as 7α-O-ethylmorroniside (1), 7β-O-ethylmorroniside (2), dehydromorroniside (3), loganin (4), 7-dehydrologanin (5), 7-formyloysecologanin (6), sweroside (7), coniferyl alcohol 9-O-β-D-glucopyranoside (8), 3-methoxy-4-(2-glycerol)-phenylpropanol (9), (7R, 8R)-7, 8-dihydro-9'-hydroxyl-3'-methoxyl-8- hydroxymethyl-7-(4-hydroxyl-3-methoxyphenyl)- 1'-benzofuranpropanol-9'-O-β-D-glucopyranoside (10), (7R, 8R)-4, 7, 9, 9'- tetrahydroxy-3-methoxy-8-O-4'- neoligan-3'-O-β-D-glucopyranoside (threo) (11), (7R, 8R)-3-methoxy-8, 4'-oxyneoligna-3', 4, 7, 9, 9'- pentol (threo) (12), 5-(1'-hydroxyethyl)-methyl nicotinate (13), 3-(hydroxyacetyl) indole (14), 4'-hydroxy-N-(4-hydroxy-3- methoxybenzoyl)-3', 5'-dimethoxybenzamide (15), 3-methoxyl-1H-pyrrole (16), (1S, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3- carboxylic acid (17), and syringic acid-4-O-α-L-rhamnopyranoside (18). Conclusion: Compounds 8-10 and 13-17 are firstly isolated from the plants in Caprofoliaceae, and furthermore, compounds 1-4, 6, 11, and 18 are isolated from the plants of Sambucus L. for the first time.
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Objective: To study the chemical constituents from the roots of Millettia speciosa (Leguminosae). Methods: Compounds in the 95% ethanol extract from the air-dried roots of M. speciosa were isolated by chromatography on silica gel column together with recrystallization, and their structures were identified by their physicochemical characteristics and spectral features. Results: Sixteen components were isolated from the air-dried roots of M. speciosa and identified as 7-oxo-β-sitosterol (1), aurantiamide acetate (2), shionone (3), maleic acid (4), psoralen (5), N-methylcytisine (6), lupeol caffeate (7), bisdemethoxycurcumin (8), vanillic acid (9), syringic acid (10), 6-methoxydihdyrosanguinarine (11), glycyrrhizic acid (12), (E)-3, 3'-dimethoxy-4, 4'-dihydroxystilbene (13), schisandrol B (14), 7-hydroxylathyrol (15), and nardosinone (16). Conclusion: All the compounds are isolated from this plant for the first time, and compounds 3, 7, 8, 11, and 13-16 are isolated from the plants of Leguminosae for the first time, compounds 2, 4-6, 9, 10 are isolated from the plants of Millettia Wight et Arn. for the first time.
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Objective: To study the antiviral constituents from the active fraction of Re-Du-Ning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the mice model loaded with restraint stress infected with influenza virus. The investigation on this fraction led to the isolation and identification of compounds through various chromatographic techniques and spectroscopic methods. In addition, the in vitro activity on influenza virus A (A/PR/8/34 H1N1) of the flavonoids was evaluated in vitro by the method for the detection of anti-influenza virus neuraminidase activity. Results: Through the macroporous adsorption resin, 95% ethanol eluate of RDN Injection was proved to be the antivirus active fraction of RDN Injection. Twenty compounds were obtained and characterized as syringic acid (1), ferulic acid (2), benzoic acid (3), caffeic acid (4), p-hydroxy benzaldehyde (5), vanillin (6), 4-hydroxy-3-methoxy styrene acrylic acid (7), trans-p-hydroxy cinnamic acid (8), trans-o-hydroxy cinnamic acid (9), trans-cinnamic acid (10), 7-hydroxy-6-methoxy coumarin (11), 7-hydroxy-6, 8-dimethoxy coumarin (12), coumarin (13), 3-hydroxy-1, 2-bis (4-hydroxy-3-methoxyphenyl)-1-propanone (14), isorhamnetin (15), quercetin (16), luteolin (17), rutin (18), hyperoside (19), and luteolin-7-O-β-D-glucoside (20). Among them, luteolin exhibited the antivirus activity against Flu A virus. Conclusion: All the isolated compounds are reported from RDN Injection for the first time, and luteolin exhibits the most potential activity against H1N1.
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Methyl gallate (meGAL) is known as one of major antioxidants. To investigate whether meGAL protects human cells from oxidative stress, meGAL extracted from Korean medicinal plant, Cercis chinensis leaves, was primarily screened using cell viability assay against oxidative stress. Human umbilical vein endothelial cells (HUVECs) were treated with three different concentrations of meGAL for indicated time. After or during meGAL treatment, H2O2 was added and incubated. meGAL showed free radical scavenging effect at low concentration (0.02 mM) and cell protective effect against H2O2-mediated oxidative stress. meGAL recovered viability of HUVECs damaged by H2O2-treatment, reduced the lipid peroxidation (LPO) and decreased the internal reactive oxygen species (ROS) level elevated by H2O2-treatment. Free radical scavenging effect of meGAL was proven to be very high. Differential display reverse transcription-PCR analysis showed that meGAL upregulated the levels of regulator of chromatin condensation 1, type 1 sigma receptor and phosphate carrier protein expressions, respectively. Based on structural similarity compared with meGAL, 14 chemicals were chosen and viability assay was performed. Four chemicals, haematommic acid (56.2% enhancement of viability), gallic acid (35.0%), methylorsellinic acid (23.7%), and syringic acid (20.8%), enhanced more potent cell viability than meGAL, which showed only 18.1% enhancement of cell viability. These results suggest that meGAL and four meGAL-related chemicals protect HUVECs from oxidative stress.
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Humans , Antioxidants/chemistry , Biological Assay , Catalase/analysis , Endothelial Cells/drug effects , Fabaceae/metabolism , Free Radical Scavengers/chemistry , Gallic Acid/analogs & derivatives , Gene Expression/drug effects , Molecular Structure , Oxidative Stress/drug effects , Plant Extracts/chemistry , Plant Leaves/metabolism , Superoxide Dismutase/analysis , Umbilical Veins/cytology , Water/pharmacologyABSTRACT
Object To study the anti endotoxic effect of syringic acid (SA) which was isolated from Radix Isatidis (Banlangen in Chinese, BLG). Methods SA was extracted and isolated from BLG and made to 1% solution. The content of SA pretreated ET was quantitatively determined using Limulus Test. Then the ability of fever induction of endotoxin (ET) pretreated with SA was measured using endotoxin induced fever test in rabbits. At last, the lipopolysaccharide (LPS) induced death in mice pretreated with and without SA was compared. Results Being pretreated with SA, 83.16% ET was destroyed, the ET induced fever in rabbits relieved markedly and the LPS induced death rate in mice dropped from 68% to 20%. Conclusion SA isolated from BLG has anti endotoxic effects.