Based on the fact that glycyrrhizic acid can form micelles in aqueous solution and play a role in solubilization, the optimal compatibility ratio between puerarin and glycyrrhizic acid was screened to prepare puerarin-glycyrrhizic acid dispersible tablets and investigate the dissolution of puerarin. The particle size, Zate potential and puerarin dissolution were compared among the micellar solutions with mass ratio of 7∶1, 6∶1, 5∶1, 4∶1, 3∶1 and 2∶1(puerarin to glycyrrhizic acid), and it was found that when the mass ratio of puerarin and glycyrrhizic acid was 5∶1, the micelle showed smallest particle size, uniform distribution, and largest puerarin dissolution, so mass ratio of 5∶1 was determined as the optimal condition. The formulation of puerarin-glycyrrhizic acid dispersible tablets was optimized by single factor and orthogonal test: puerarin 100.0 mg, glycyrrhizin 20.0 mg, polyvinylpolypyrrolidone 24.0 mg as disintegrating agent, microcrystalline cellulose 135.0 mg as stuffing bulking agent, hydroxypropyl methyl cellulose 18.0 mg as adhesive agent, magnesium stearate 2.7 mg as lubricant, and tablet weight of 300.0 mg. High-performance liquid chromatography(HPLC) method was used to determine the content of puerarin in dispersible tablets. Puerarin showed a good linear relationship(r=0.999 8) in the range of 15.5-248 g·L~(-1), with high precision(RSD<2.0%) and good repeatability(RSD<2.0%), and the recovery rate was 101.1%, RSD 0.89%. There was no significant difference in the quantity of puerarin in different batches of puerarin-glycyrrhizic acid dispersible tablets. When the artificial gastric juice was used as the dissolution medium, the dissolution of puerarin in puerarin-glycyrrhizic acid dispersible tablets could reach over 85% within 15 min. When phosphate buffer(pH 6.8) was used as the dissolution medium, the dissolution of puerarin in the puerarin-glycyrrhizic acid dispersible tablets had a faster dissolution rate in vitro, 99.8% in 30 min. Therefore, puerarin-glycyrrhizic acid dispersible tablets could improve the dissolution of puerarin in vitro due to the solubilization effect of glycyrrhizic acid.
Glycyrrhizic Acid ; chemistry ; Isoflavones ; chemistry ; Solubility ; Tablets

To decrease the hemolysis side effect of puerarin, the basic formula and preparation of puerarin submicron emulsion were optimized and the physicochemical properties were evaluated. Puerarin submicron emulsions were prepared by phase inversion-ultrasound combining with phospholipids complexes technology. The effects of preparative parameters, such as emulsification time, stirring velocity and ultrasound time, on mean diameter, span of dispersity, entrapment efficiency and overall desirability were investigated. The three dimensional response surface graphs were produced by second-order polynomial and liner equation, which predict the optimal experiment conditions. All response variables were found to be greatly dependent on three independent variables. Second-order polynomial equations were fitter than liner equations for this study. The optimal emulsification time, stirring velocity and ultrasound time was 15 min, 2 000 r x min(-1), 30 min, respectively. The mean diameter, span of dispersity, entrapment efficiency, drug content and zeta potential of emulsions prepared by the method were 228.23 nm, 0.628 4, 84. 32%, 9.98 mg x mL(-1), - 29.03 mV, respectively. Puerarin submicron emulsion was prepared by the optimized preparation method. The narrow particle diameter distribution, high envelopment efficacy and good stability were obtained. The physicochemical properties were suitable for the requirement of the intravenous emulsion.
Emulsions ; Isoflavones ; administration & dosage ; chemistry ; Particle Size

To study chemical constituents of Polygonatum odoratum (Mill.) Druce, the compounds were separated with column chromatography and HPLC. On the basis of physicochemical properties and spectral data, their structures were confirmed. Nine compounds were isolated and identified as 5,7-dihydroxy-6-methoxyl-8-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (1), 5,7-dihydroxy-6-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6-methoxyl-8-methyl-3-(4'-methoxybenzyl)chroman-4-one (3), disporopsin (4), chrysoeriol (5), 5,4'-dihydroxy-7-methoxy-6-methylflavone (6), N-trans-feruloyltyramine (7), N-trans-feruloyloctopamine (8), and (+)-syringaresinol (9). Compounds 1-3 are new homoisoflavanones. Compounds 4-9 are isolated from this plant for the first time.
Isoflavones ; isolation & purification ; Molecular Structure ; Polygonatum ; chemistry

OBJECTIVETo study the chemical constituents from the vine stems of isoflavones of Millettia nitita var. hirsutissima.

METHODChromatographic methods were used to isolate compounds, and spectroscopic methods were used to elucidate the structures.

RESULTFour isoflavones were isolated and identified: 3'-O-methylorobol (1), genistein (2), biochanin A (3), afromosin (4).

CONCLUSIONAll Compounds were obtained from the plant for the first time.

Genistein ; chemistry ; isolation & purification ; Isoflavones ; chemistry ; isolation & purification ; Millettia ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry

Mian-Zao-Er was collected from the bulbs of Scilla scilloides (Lindl. ) Druce, belonging to the Hyacinthaceae family. 17 compounds were obtained using various column chromatographies on macroporus resin (HPD100), silica gel, Sephadex LH-20 and ODS, as well as semi-preparative HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral data as 2-hydroxy-7-methoxyscillascillin (1), scillascillin (2), 5,7-dihydroxy-3',4'-dimethoxyspiro 2H-1-benzopyran-7'-bicyclo[4.2.0 ] octa [1,3,5 ] -trien } -4-one (3), socialinone (4), 4-methylresveratrol (5), (E)-resveratrol (6), scillavoneA (7), 3,9-di- hydroeucomnalin (8), 3-(3-hydroxy-4-methoxybenzyl) -5,7-dihydroxychroman-4-one (9), (3R)-5,7,3'-trihydroxy-4'-methoxyspiro (2H-1-benzopyran-7'-bicyclo[4, 2, 0] octa [1, 3, 5]-trien} -4-one (10), scillabene A (11), 2-hydroxyscillascillin (12), 3-(4-hydroxybenzyl) -5,7-dihydroxychroman-4-one (13), 3-( 4-hydroxybenzylidene) -5, 7-dihydroxychroman-4-one (14), 3-( 4-hydroxybenzyl) -5-hydroxy-7,8-dimethoxychroman-4-one (15), 3-(4-hydroxybenzyl) -5-hydroxy-6, 7-dimethoxychroman-4-one (16), and 3-(4-hydroxybenzyl)-5,8-hydroxy-7-methoxychroman-4-one (17). Among them, compounds 3, 4, 6, 9, 13 and 15-17 were isolated from this plant for the first time.
Drugs, Chinese Herbal ; chemistry ; Flowers ; chemistry ; Isoflavones ; chemistry ; Mass Spectrometry ; Molecular Structure ; Scilla ; chemistry ; Stilbenes ; chemistry

OBJECTIVETo investigate the isoflavones from the vines of Pueraria lobata.

METHODThe compounds were isolated by column chromatography over silica gel and RP-C18, and purified by Sephadex LH-20 column chromatography and preparative TLC. The structures were elucidated on the basis of physico-chemical properties and spectral data.

RESULTTwelve compounds were isolated and identified as: 3'-methoxydaidzein (1), formononetin (2), genistein (3), daidzein (4), daidzin (5), genistin (6), ononin (7), 5-hydroxyl ononin (8), calycosin (9), 6"-O-acetyl genistein (10), 6"-O-acetyl daidzin (11), puerarin (12).

CONCLUSIONFor the first time, compounds 9-11 were isolated from the genus Pueraria plant, and compounds 1, 3, 6-8 were obtained from the vines of this plant.

Genistein ; chemistry ; Glucosides ; chemistry ; Isoflavones ; chemistry ; Magnetic Resonance Spectroscopy ; Plant Stems ; chemistry ; Pueraria ; chemistry

OBJECTIVETo develop a method for analyzing the chemical compositions of Gegen and Fenge extracts using high-performance capillary electrophoresis (HPCE).

METHODSUsing HPCE/DAD, the chemical composition of the extracts was analyzed with the buffer solution of 40 mmol/L borax containing 16.7% methanol, with injection pressure at 137.9 kPa for 5 s, separation voltage at 25 kV in 0-5 min time range and at 22 kV in 5-25 min time range, and the temperature of the capillary of 20 degrees celsius.

RESULTS AND CONCLUSIONThe method for analysis of Gegen and Fenge extracts was established, which identified puerarin and daidzein as the two major components. This simple and rapid analysis method can be used for Gegen and Fenge extract fingerprinting.

Electrophoresis, Capillary ; methods ; Isoflavones ; analysis ; Pueraria ; chemistry ; Reproducibility of Results

Based on the systematic retrieval and the reported components of Sojae Semen Nigrum and Sojae Semen Praeparatum, this study conducted in-depth analysis of conversion of components in the fermentation process, and discussed types and possible mec-hanisms of conversion of chemical components, so as to provide the basis for studying technology, medicinal ingredients and quality standards. According to the analysis, there is a certain degree of conversion of nutrients(like protein, sugar, lipid), bioactive substances(like isoflavones, saponins, γ-aminobutyric acid) and other substances(like nucleosides, melanoids, biamines, etc) in the process of fermentation.
Chromatography, High Pressure Liquid ; Fermentation ; Isoflavones/analysis* ; Semen/chemistry* ; Soybeans

Pueraria thomsonii has long been used in traditional Chinese medicine. Isoflavonoids are the principle pharmacologically active components, which are primarily observed as glycosyl-conjugates and accumulate in P. thomsonii roots. However, the molecular mechanisms underlying the glycosylation processes in (iso)flavonoid biosynthesis have not been thoroughly elucidated. In the current study, an O-glucosyltransferase (PtUGT8) was identified in the medicinal plant P. thomsonii from RNA-seq database. Biochemical assays of the recombinant PtUGT8 showed that it was able to glycosylate chalcone (isoliquiritigenin) at the 4-OH position and glycosylate isoflavones (daidzein, formononetin, and genistein) at the 7-OH or 4'-OH position, exhibiting no enzyme activity to flavonones (liquiritigenin and narigenin) in vitro. The identification of PtUGT8 may provide a useful enzyme catalyst for efficient biotransformation of isoflavones and other natural products for food or pharmacological applications.
Cloning, Molecular ; Genistein ; Glucosyltransferases/metabolism* ; Isoflavones/pharmacology* ; Pueraria/chemistry*

OBJECTIVETo prepare puerarin deoxycholate/phospholipid mixed micelle to increase the solubility of puerarin.

METHODSodium deoxycholate and soybean phospholipids were used to prepare puerarin mixed micelle through orthogonal design experiments. With the solubility, shape and particle size as the response indexes, the preparing process of puerarin mixed micelle was optimized.

RESULTThe optimized process for the puerarin deoxycholate/phospholipid mixed micelle was that the puerarin, soya phosphatidylcholine and sodium deoxycholate with the mole ratio of 3:2:4 should be dissolved in methanol-chloroform (1:1), and the solvents should be evaporated rotatively at 30 degrees C. The particle diameter of the mixed micelle was (64.8 +/- 13) nm (volume-weighted particle size distribution), and the solubility was 0.811 1 g x L(-1) in water at the room temperature, which was 22.3 times as that of the raw puerarin (0.036 4 g x L-1).

CONCLUSIONThe puerarin deoxycholate/phospholipid mixed micelle can improve the solubility of puerarin significantly.

Deoxycholic Acid ; chemistry ; Isoflavones ; chemistry ; Micelles ; Particle Size ; Phospholipids ; chemistry ; Plant Extracts ; chemistry ; Solubility