Chalcones (1,3-diaryl-2-propen-1-ones), a subfamily of flavonoid, are widely known to possess potent anti-inflammatory and anti-oxidant properties. In this study, we investigated the effect of 3-(4-Hydroxyphenyl)-1-(thio3-(4-Hydroxyphenyl phen-2-yl)prop-2-en-1-one (TI-I-175), a synthetic chalcone derivative, on endotoxin-induced expression of monocyte chemoattractant protein-1 (MCP-1), one of the key chemokines that regulates migration and infiltration of immune cells, and its potential mechanisms. TI-I-175 potently inhibited MCP-1 mRNA expression stimulated by lipopolysaccharide (LPS) in RAW 264.7 macrophages without significant effect on cell viability. Treatment of cells with TI-I-175 markedly prevented LPS-induced transcriptional activation of activator protein-1 (AP-1) as measured by luciferase reporter assay, while nuclear factor-kappaB (NF-kappaB) activity was not inhibited by TI-I-175, implying that TI-I-175 suppressed MCP-1 expression probably via regulation of AP-1. In addition, TI-I-175 treatment significantly inhibited LPS-induced Akt phosphorylation and led to a significant decrease in reactive oxygen species (ROS) production by LPS, which act as up-stream signaling events required for AP-1 activation in RAW 264.7 macrophages. Taken together, these results indicate that TI-I-175 suppresses MCP-1 gene expression in LPS-stimulated RAW 264.7 macrophages via suppression of ROS production and Akt activation.
Cell Survival ; Chalcone* ; Chalcones ; Chemokine CCL2 ; Chemokines ; Gene Expression ; Inflammation ; Luciferases ; Macrophages* ; Phosphorylation ; Reactive Oxygen Species ; RNA, Messenger ; Transcription Factor AP-1 ; Transcriptional Activation

OBJECTIVETo investigate the anti-HIV constituents from the root of Polygonatum kingianum.

METHODThe compounds were isolated by column chromatography on silica gel, Sephadex LH-20, MCI-gel CHP-20P and their structures were determined on the basis of their spectroscopic evidence including IR, MS and NMR data.

RESULT13 compounds were isolated, of which nine compounds were identified as liquiritigenin, isoliquiritigenin, 4', 7-dihydroxy-3'-methoxyisoflavone, (6aR, 11aR)-10-hydroxy-3, 9-dimethoxypterocarpan, 5-hydroxymethyl-2-furancarboxaldehyde, salicylic acid, n-butyl-beta-D-fructopyranoside, n-butyl-beta-D-fructofuranoside, n-butyl-alpha-D-fructofuranoside.

CONCLUSIONCompounds 1-6 were obtained from this plant for the first time.

Chalcone ; analogs & derivatives ; chemistry ; isolation & purification ; Chalcones ; Flavanones ; Flavonoids ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Polygonatum ; chemistry ; Salicylic Acid ; chemistry ; isolation & purification

To study the chemical constituents from the stems and leaves of Humulus scandens, this study isolated thirteen compounds by different chromatographic methods including silica gel column, ODS, Sephadex LH-20 and preparative HPLC. Based on comprehensive analysis, the chemical structures were elucidated and identified as citrunohin A(1), chrysosplenetin(2), casticin(3), neoechinulin A(4), ethyl 1H-indole-3-carboxylate(5), 3-hydroxyacetyl-indole(6),(1H-indol-3-yl) oxoacetamide(7), inonotusic acid(8), arteannuin B(9), xanthotoxol(10), α-tocopherol quinone(11), eicosanyl-trans-p-coumarate(12), and 9-oxo-(10E,12E)-octadecadienoic acid(13). Among them, compound 1 was a new dihydrochalcone, and the other compounds were obtained from H. scandens for the first time.
Humulus ; Chalcones ; Indoles ; Drugs, Chinese Herbal/chemistry*

Five new flavonoid derivatives, cajavolubones A-E (1-5), along with six known analogues (6-11) were isolated from Cajanus volubilis, and their structures were elucidated by spectroscopic analysis and quantum chemical calculations. Cajavolubones A and B (1 and 2) were identified as two geranylated chalcones. Cajavolubone C (3) was a prenylated flavone, while cajavolubones D and E (4 and 5) were two prenylated isoflavanones. Compounds 3, 8, 9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.
Flavonoids/chemistry* ; Cajanus ; Molecular Structure ; Chalcones/chemistry*

Chalcones (1,3-diaryl-2-propen-1-ones), a flavonoid subfamily, are widely known for their anti-inflammatory properties. Propenone moiety in chalcones is known to play an important role in generating biological responses by chalcones. In the present study, we synthesized chalcone derivatives structurally modified in propenone moiety and examined inhibitory effect on nitric oxide (NO) production and its potential mechanisms. Among the chalcone derivatives used for this study, TI-I-174 (3-(2-Hydroxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one) most potently inhibited lipopolysaccharide (LPS)-stimulated nitrite production in RAW 264.7 macrophages. TI-I-174 treatment also markedly inhibited inducible nitric oxide synthase (iNOS) expression. However, TI-I-174 did not significantly affect production of IL-6, cyclooxygenase-2 (COX-2) and tumor necrosis factor-alpha (TNF-alpha), implying that TI-I-174 inhibits production of inflammatory mediators in a selective manner. Treatment of macrophages with TI-I-174 significantly inhibited transcriptional activity of activator protein-1 (AP-1) as determined by luciferase reporter gene assay, whereas nuclear factor-kappaB (NF-kappaB) activity was not affected by TI-I-1744. In addition, TI-I-174 significantly inhibited activation of c-Jun-N-Terminal kinase (JNK) without affecting ERK1/2 and p38MAPK, indicating that down-regulation of iNOS gene expression by TI-I-174 is mainly attributed by blockade of JNK/AP-1 activation. We also demonstrated that TI-I-174 treatment led to an increase in heme oxygenase-1 (HO-1) expression both at mRNA and protein level. Transfection of siRNA targeting HO-1 reversed TI-I-174-mediated inhibition of nitrite production. Taken together, these results indicate that TI-I-174 suppresses NO production in LPS-stimulated RAW 264.7 macrophages via induction of HO-1 and blockade of AP-1 activation.
Chalcone* ; Chalcones ; Cyclooxygenase 2 ; Down-Regulation ; Gene Expression ; Genes, Reporter ; Heme Oxygenase-1* ; Inflammation ; Interleukin-6 ; Luciferases ; Macrophages* ; Nitric Oxide Synthase Type II ; Nitric Oxide* ; Phosphotransferases ; RNA, Messenger ; RNA, Small Interfering ; Transcription Factor AP-1* ; Transfection ; Tumor Necrosis Factor-alpha

AIMTo study the chemical constituents of Caragana intermedia.

METHODSThe compounds were separated by chromatography methods, their structures were identified by spectral analysis.

RESULTSTen compounds were isolated and identified as 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (1), 3,5,7,8,4'-pentahydroxy-3'-methoxyflavone(2), puercetin(3), limocitrin(4), 5,7,3',4'-tetrahydroxy-3-methoxyflavone(5), 7,3',5'-trihydroxyflavanone(6), 5,7,3',4'-tetrahydroxy-3,8-dimethoxyflavone(7), butein(8), liquiritigenin(9) and 5,7,4'-trihydroxy-3,8-dimethoxyflavone(10).

CONCLUSIONCompound 6 is a new compound and the others were obtained from this plant for the first time.

Caragana ; chemistry ; Chalcone ; analogs & derivatives ; chemistry ; isolation & purification ; Chalcones ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Flavanones ; chemistry ; isolation & purification ; Flavonoids ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Quercetin ; chemistry ; isolation & purification

AIMTo study the chemical constituents of Hedysarum polybotrys Hand.-Mazz..

METHODSThe compounds were separated with Sephadex LH-20 and silica gel column chromatography, and their structures were identified on the basis of spectral analysis.

RESULTSFive compounds were identified as hedysalignan A (1), isoliquiritigenin (2), formononetin (3), calycosin (4) and ononin (5).

CONCLUSIONHedysalignan (1) is a new compound and the others were obtained from the plant for the first time.

Chalcone ; analogs & derivatives ; chemistry ; isolation & purification ; Chalcones ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Fabaceae ; chemistry ; Furans ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Isoflavones ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo investigate the flavonoids of Oxytropisfalcata.

METHODCompounds were isolated by column chromatography using silica gel, Sephadex LH -20 and ODS as the adsorbents. Their structures were elucidated by NMR and MS spectroscopic data.

RESULTEight compounds were isolated and elucidated as 2', 4'-dihydroxy-4-methoxy chalcone (1), 2', 4'-dihydroxy chalcone (2), 5,7-dihydroxy-4'-methoxy flavonol (3), 7-hydroxy-4'-methoxy flavanones (4), 3', 7-dihydroxy-2',4'-dimethoxy isoflavan (5), 2'-hydroxy-4'-methoxy chalcone (6), 2'-methoxy-4'-hydroxy chalcone (7), 2',4'-dihydroxy dihydrochalcone (8).

CONCLUSIONAll compounds were obtained from O. falcata for the first time.

Chalcones ; chemistry ; isolation & purification ; Flavonoids ; chemistry ; isolation & purification ; Oxytropis ; chemistry ; Plants, Medicinal ; chemistry

Duosuike Tiancha contain multiple dihydrochalcone sweet constituents, which are mainly active constituents. For the purpose of overall assessment on quality Duosuike Tiancha, 5 sweet dihydrochalcones in Duosuike Tiancha, phloridzin, phloretin-4'-beta-D-glucopyranoside, 3'-O-acetylphloridzin, 2'-O-acetylphloridzin and phloretin are determined as indicators. The separation was carried out through a isocratic elution using a Waters Acquity UPLC BRH C18 (2.1 mm x 100 mm, 1.7 microm) column and a mobile phase consisting of water (75%) and acetonitrile (25%) at a flow rate of 0.5 mL x min(-1). The detection wavelength was set at 285 nm. The column temperature was 40 degrees C. Under the optimized conditions, all the 5 sweet constituents were successfully separated with in 6 min, and good linearity (r2 > 0.999 1) was achieved. The linear range (g x L(-)) and recoveries were tested with results of 0.022 2-0.444 (98.37%), 0.102 84. 112 (97.32%), 0.003 39-0.067 68 (96.77%), 0.005 1-0.204 (98.85%) and 0.000 538-0.010 76 (100.91%) respectively. The results indicate that the content of the 5 dihydrochalcones were 7.83-62.37, 114.24-272.35, 0-1.02, 0-5.11 and 0.10-1.19 mg x g(-1), respectively. Furthermore, with certain regularity between their content and the sample size, harvest time. The separation and analysis method are fast and simple, as evidenced by the fact that the gradient elution is adopted to rapidly determine one sample within six minutes. Therefore, it can be used for dsetermine 5 sweet dihydrochalcones Duosuike Tiancha.
Chalcones ; chemistry ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; chemistry ; Fagaceae ; chemistry

OBJECTIVETo establish an HPLC method for simultaneous determination of contents of loureirin A, loureirin B, 7,4'-dihydroxy flavone, pterostilbene and resveratrol in resina draconis and its extracts.

METHODKromasil 100-5C18 column (4.6 mm x 250 mm, 5 microm) was used with the mobile phase of acetonitrile-1% glacial acetic acid at a flow rate of 1.0 mL x min(-1) and the column temperature at 40 degrees C. The detective wave length of loureirin A and B was detected at 278 nm, and 7,4'-dihydroxy flavone, pterostilbene and resveratrol was at 319 nm.

RESULTAll the five active components reached the resolved peaks within 40 min, indicating a good linearity (r > or = 0.999 7). The average recoveries of loureirin A, loureirin B, 7,4'-dihydroxy flavone, pterostilbene and resveratrol in resina draconis were 102.9%, 96.81%, 97.29%, 100.7% and 103.7%, with RSDs of 0.23%, 1.5%, 0.42%, 0.58% and 0.34%, respectively. The average recoveries of loureirin A, loureirin B, 7,4'-dihydroxy flavone, pterostilbene and resveratrol in extract of resina draconis were 102. 2% , 96. 93%, 97. 90% , 102.0% and 103.3%, with RSDs of 1.7%, 0.91%, 1.4%, 1.5% and 1.2%, respectively.

CONCLUSIONThe method is so easy, accurate, highly repeatable and stable that it provides good reference for the quality control of resina draconis and its extracts.

Chalcones ; analysis ; Chromatography, High Pressure Liquid ; methods ; Dracaena ; chemistry ; Flavones ; analysis ; Resins, Plant ; analysis ; Stilbenes ; analysis