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*

Carthami Flos, as a traditional blood-activating and stasis-resolving drug, possesses anti-tumor, anti-inflammatory, and immunomodulatory pharmacological activities. Flavonoid glycosides are the main bioactive components in Carthamus tinctorius. Glycosyltransferase deserves to be studied in depth as a downstream modification enzyme in the biosynthesis of active glycoside compounds. This study reported a flavonoid glycosyltransferase CtUGT49 from C. tinctorius based on the transcriptome data, followed by bioinformatic analysis and the investigation of enzymatic properties. The open reading frame(ORF) of the gene was 1 416 bp, encoding 471 amino acid residues with the molecular weight of about 52 kDa. Phylogenetic analysis showed that CtUGT49 belonged to the UGT73 family. According to in vitro enzymatic results, CtUGT49 could catalyze naringenin chalcone to the prunin and choerospondin, and catalyze phloretin to phlorizin and trilobatin, exhibiting good substrate versatility. After the recombinant protein CtUGT49 was obtained by hetero-logous expression and purification, the enzymatic properties of CtUGT49 catalyzing the formation of prunin from naringenin chalcone were investigated. The results showed that the optimal pH value for CtUGT49 catalysis was 7.0, the optimal temperature was 37 ℃, and the highest substrate conversion rate was achieved after 8 h of reaction. The results of enzymatic kinetic parameters showed that the K_m value was 209.90 μmol·L~(-1) and k_(cat) was 48.36 s~(-1) calculated with the method of Michaelis-Menten plot. The discovery of the novel glycosyltransferase CtUGT49 is important for enriching the library of glycosylation tool enzymes and provides a basis for analyzing the glycosylation process of flavonoid glycosides in C. tinctorius.
Carthamus tinctorius/chemistry* ; Phylogeny ; Flavonoids/analysis* ; Glycosides/analysis* ; Glycosyltransferases/genetics* ; Anti-Inflammatory Agents ; Chalcones

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*

Since exploding rates of modern mental diseases, application of antidepressants has increased. Worryingly, the antidepressant-induced liver injury has gradually become a serious health burden. Furthermore, since most of the knowledge about antidepressant hepatotoxicity are from pharmacovigilance and clinical case reports and lack of observational studies, the underlying mechanisms are poorly understood and there is a lack of efficient treatment strategies. In this study, antidepressant paroxetine directly triggered inflammasome activation evidenced by caspase-1 activation and downstream effector cytokines interleukin(IL)-1β secretion. The pretreatment of echinatin, a bioactive component of licorice, completely blocked the activation. This study also found that echinatin effectively inhibited the production of inflammasome-independent tumor necrosis factor α(TNF)-α induced by paroxetine. Mechanistically, the accumulation of mitochondrial reactive oxygen species(mtROS) was a key upstream event of paroxetine-induced inflammasome activation, which was dramatically inhibited by echinatin. In the lipopolysaccharide(LPS)-mediated idiosyncratic drug-induced liver injury(IDILI) model, the combination of LPS and paroxetine triggered aberrant activation of the inflammasome to induce idiosyncratic hepatotoxicity, which was reversed by echinatin pretreatment. Notably, this study also found that various bioactive components of licorice had an inhibitory effect on paroxetine-triggered inflammasome activation. Meanwhile, multiple antidepressant-induced aberrant activation of the inflammasome could be completely blocked by echinatin pretreatment. In conclusion, this study provides a novel insight for mechanism of antidepressant-induced liver injury and a new strategy for the treatment of antidepressant-induced hepatotoxicity.
Animals ; Humans ; Mice ; Antidepressive Agents/adverse effects* ; Chemical and Drug Induced Liver Injury, Chronic/prevention & control* ; Glycyrrhiza/chemistry* ; Inflammasomes/drug effects* ; Interleukin-1beta/metabolism* ; Lipopolysaccharides/toxicity* ; Mice, Inbred C57BL ; NLR Family, Pyrin Domain-Containing 3 Protein ; Paroxetine/adverse effects* ; Tumor Necrosis Factor-alpha ; Chalcones/therapeutic use*

The qualitative analysis of flavonoids in Coreopsis tinctoria was carried out by a combination of 2 D-TLC and HPLC-IT-TOF-MS. The separation was conducted on 2 D-TLC and a Phenomenex Kinetex Evo C_(18) column(2.1 mm×100 mm, 2.6 μm) with methanol-0.05% aqueous formic acid by gradient elution. Electrospray ionization-(ESI) source was applied and operated in both positive and negative ionization modes. Eighteen flavonoids including three flavonoids, one flavonol, nine flavonones, one flavanonol and four chalcones, were putatively identified from the flavone-enriched fraction of C. tinctoria. 2 D-TLC could separate the flavonoids from C. tinctoria. HPLC-IT-TOF-MS was able to quickly and accurately analyze the flavonoids in C. tinctoria. The results would provide experimental information for the efficacy material basis clarification of C. tinctoria.
Chalcones ; analysis ; Chromatography, High Pressure Liquid ; Coreopsis ; chemistry ; Flavonoids ; analysis ; Phytochemicals ; analysis ; Plant Extracts ; analysis ; Spectrometry, Mass, Electrospray Ionization

During the screening of a traditional Chinese folk herb library against HepG2 and Hep3B cell lines, the EtOAc extract from the Tibetan medicine, Caragana tibetica (CT-EtOAc) exhibited potential anti-hepatocellular carcinoma (anti-HCC) activity. HPLC-based activity profiling was performed for targeted identification of anti-HCC activity from CT-EtOAc by MS-directed purification method. CT-EtOAc was separated by time-based fractionation for further anti-HCC bioassay by a semipreparative HPLC column (150 mm × 10 mm i.d., 5 μm) with a single injection of 5 mg. Bioassay-guided and ESIMS-directed large scale purification was performed with a single injection of 400 mg of CT-EtOAc by peak-based fractionation. A 1.4-mm heavy wall micro NMR tube with z-gradient was used to measure one and two dimensional NMR spectra for the minor or trace amounts of components of the extract. Two active compounds could be elucidated as naringenin chalcone (CT-1) and 3-hydroxy-8, 9-dimethoxypterocarpan (CT-2) relevant to anti-HCC effects for the EtOAc extract of C. tibetica rapidly and unambiguously by this protocol.
Acetates ; pharmacology ; Antineoplastic Agents ; chemistry ; pharmacology ; Caragana ; chemistry ; Carcinoma, Hepatocellular ; drug therapy ; Cell Line, Tumor ; Chalcones ; pharmacology ; Chromatography, High Pressure Liquid ; Hep G2 Cells ; Humans ; Liver Neoplasms ; drug therapy ; Medicine, Tibetan Traditional ; Plant Extracts ; chemistry ; pharmacology ; Plant Roots ; chemistry

To study the mechanisms of total flavonoid from Glycyrrhizae Radix et Rhizoma (TFGR) and its ingredient isoliquiritigenin (ISL) on their regulation of M2 phenotype polarization of macrophages. IL-4 (60 μg x L(-1)) induced RAW264.7 cells for 6 h to establish the M2 macrophage model. TFGR and ISL restrained breast cancer cells migration with the aid of M2 macrophages in vitro. TFGR and ISL inhibited gene and protein expression of Arg-1, up-regulated gene of HO-1 and protein expression of iNOS, enhanced the expression of microRNA 155 and its target gene SHIP1, meanwhile down-regulated.the phosphorylation of STAT3 and STAT6. So TFGR and ISL were the bioactive fraction and ingredient in Glycyrrhizae Radix et Rhizoma to reverse M2 phenotype macrophages polarization. TFGR and ISL inhibited the promotion of M2 macrophages to breast cancer cells migration in vitro, STAT signal pathways and miR155 were partly involved.
Animals ; Cell Line, Tumor ; Cell Movement ; drug effects ; Cell Polarity ; drug effects ; Chalcones ; pharmacology ; Flavonoids ; pharmacology ; Glycyrrhiza ; chemistry ; Interleukin-4 ; genetics ; metabolism ; Macrophages ; cytology ; drug effects ; metabolism ; Mice ; RAW 264.7 Cells ; Rhizome ; chemistry

OBJECTIVETo study the in-vitro inducing apoptosis mechanism of human hepatoma SMMC-7721 cells by 2',4'-di- hydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC), a chalcone compound from Cleistocalyx operculatus.

METHODQuantitative DNA fragmentation assay was carried out to detect the effect of DMC of different concentrations on SMMC-7721 cells, according to the method of Sellins and Cohen with some modifications. Telomerase activities of the cells were determined by PCR-ELISA methods. The expression quantity of c-myc and hTERT mRNA were determined by semi-quantitative RT-PCR The effect of DMC on expression levels of cmyc and hTERT protein were measured by western blot.

RESULTThe percentage of DNA fragmentation increased with notable concen- tration dependence, after treatment with DMC for 48 h. Compared with that of control group, the telomerase activity of the cells de- creased by (66.2 ± 2.1)% after 48 h treatment with 20 μmol x L(-1) DMC, the mRNA expression of c-myc and hTERT decreased by (67.3 ± 2.1)% and (64.4 ± 2.3)%, respectively, and the protein expression of c-myc and hTERT decreased by (69.6 ± 1.9)% and (71.3 ± 2.4)%, respectively.

CONCLUSIONDMC can induce SMMC-7721 cell apoptosis and the apoptosis mechanism may be related to the decreased mRNA and protein expression of c-myc and hTERT.

Antineoplastic Agents ; pharmacology ; Apoptosis ; drug effects ; Carcinoma, Hepatocellular ; pathology ; Cell Line, Tumor ; Chalcones ; pharmacology ; DNA Fragmentation ; drug effects ; Dose-Response Relationship, Drug ; Humans ; Liver Neoplasms ; pathology ; Proto-Oncogene Proteins c-myc ; genetics ; metabolism ; RNA, Messenger ; genetics ; metabolism ; Syzygium ; chemistry ; Telomerase ; genetics ; metabolism

To study the chemical constituents of Lysimachia patungensis Hand.-Mazz., silica gel column chromatography, reverse phase ODS column chromatography, MCI and Sephadex LH-20, were used to separate the 95% EtOH extract of the whole plant of Lysimachia patungensis Hand.-Mazz.. The structures of the isolated compounds have been established on the basis of chemical and NMR spectroscopic evidence as well as ESI-MS in some cases. Twelve phenolic compounds were obtained and identified as quercetin-3, 3'-di- O-alpha-L-rhamnoside (1), myricetrin (2), quercitrin (3), rutin (4), 2-hydroxynaringenin-4'-O-glucopyranoside (5), naringenin 7-O-glucopyranoside (6), liquiritin apioside (7), licochalcone B (8), tetrahydroxymethoxy chalcone (9), methyl-p-coumarate (10), 2, 4, 6-trihydroxy acetophenone-2-O-glucopyranoside (11) and vaccihein A (12). Among them, compound 1 is a new compound, and compounds 5, 11 and 12 are isolated from the genus Lysimachia L. for the first time, and the others are isolated from the plant for the first time.
Chalcones ; chemistry ; isolation & purification ; Cinnamates ; chemistry ; isolation & purification ; Molecular Structure ; Phenols ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Primulaceae ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification ; Rutin ; chemistry ; isolation & purification

Licochalcone A (LCA), as a major flavonoid in Glycyrrhiza inflate, has attracted wide attention in recent years. Studies showed that LCA has multiple pharmacological effects such as anti-tumour, anti-inflammation, anti-bacteria and anti-parasite. We made a summary for domestic and foreign study literatures for various pharmacological effects of LCA.
Animals ; Anti-Infective Agents ; pharmacology ; Anti-Inflammatory Agents ; pharmacology ; Antineoplastic Agents, Phytogenic ; pharmacology ; Chalcones ; pharmacology ; Drugs, Chinese Herbal ; pharmacology ; Glycyrrhiza ; chemistry ; Humans