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*

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*

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 study the chemical constituents of Bauhinia glauca subsp. pernervosa.

METHODThe coulis of B. glauca subsp. pernervosa were extracted with 95% EtOH at room temperature. The compounds were isolated and separated by chromatographic techniques, and structures were identified by spectroscopic methods.

RESULTSeven chalcones were isolated and identified: butein-4-methyl ether (1), isoliquiritigenin (2), butein (3), isoliquiritigenin-2'-methyl ether (4), 2',4'-dihydroxychalcone (5), isoliquiritigenin-4-methyl ether (6), 4-hydroxy-2',4'-dimethoxychalcone (7).

CONCLUSIONCompounds 1, 3, and 7 were isolated from the genus Bauhinia for the first time, the other compounds were obtained from this plant for the first time.

Bauhinia ; chemistry ; Chalcones ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification

Isobavachalcone (IBC) or (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)-phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one or (E)-4,2',4'-trihydroxy-3'-prenylchalcone; 2',4,4'-trihydroxy-3'-prenyl-transchalcone, is a prenylated chalcone of the class flavonoid, firstly isolated from Psoralea corylifolia in 1968. IBC is known to possess a wide spectrum of biological activities, antibacterial, antifungal, anticancer, anti-reverse transcriptase, antitubercular and antioxidant. The compound was isolated from plant families, mostly Moraceae and Fabaceae. This review brings out together the knowledge on IBC, and can serve as the start point for future research and valorization accomplishments.
Animals ; Biosynthetic Pathways ; drug effects ; Cell Death ; drug effects ; Chalcones ; biosynthesis ; chemistry ; pharmacology ; Humans

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

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

OBJECTIVETo study the chemical constituents in the whole plants of Sarcandra hainanensis.

METHODThe chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.

RESULTNine compounds, palmitic acid (1), icosanoic acid (2), beta-sitosterol (3), octadecanoic (4), acidchrysophanol (5), emodin (6), 2', 3'-dihydroxy-4', 6'-dimethoxychalcone (7), 2'-hydroxy4', 6'-dimethoxychalcone (8), cardamonin (9) were isolated and identified.

CONCLUSIONCompounds 1-9 were obtained from this plant for the first time. Compounds 2, 5-9 were isolated from family Chloranthaceae for the first time.

Alkanes ; chemistry ; Chalcones ; chemistry ; Eicosanoids ; chemistry ; Emodin ; chemistry ; Magnetic Resonance Spectroscopy ; Magnoliopsida ; chemistry ; Palmitic Acid ; chemistry ; Sitosterols ; chemistry ; Stearic Acids ; chemistry

In order to study the chemical components of licorice deeply and systematically, a licorice compounds database was established after the comprehensive summary of the compounds in Glycyrrhiza. The database was used to classify the licorice components anew in order to statistically analyze the distribution of each type of compounds and the compounds in the medical Glycyrrhiza plants. The results indicated that 422 compounds had been reported in Glycyrrhiza so far, and they could be categorized into 5 classes as flavoids, coumarins, triterpenoids, stilbenoids, and some others. Up to now, 170 compounds were isolated from G. uralensis, 134 compounds from G. glabra, 52 compunds from G. inflata, and 31 from G. yunnanensis. It is the first time to add categorization "stilbenoids", and "dibenzoylmethanes" classified as chalcones. In the meantime, the database is supposed to be convenient for further study.
Chalcones ; analysis ; chemistry ; Coumarins ; analysis ; chemistry ; Databases, Bibliographic ; Drugs, Chinese Herbal ; analysis ; chemistry ; Flavonoids ; analysis ; chemistry ; Glycyrrhiza ; chemistry ; classification ; Plants, Medicinal ; chemistry ; Stilbenes ; analysis ; chemistry ; Triterpenes ; analysis ; chemistry