peoniflorin and benzoylpaeoniflorin

Topics: Acetophenones; Animals; Anthocyanins; Anti-Inflammatory Agents; Benzoates; Bridged-Ring Compounds; Cardiovascular Agents; Drugs, Chinese Herbal; Glucosides; Medicine, Chinese Traditional; Medicine, East Asian Traditional; Monoterpenes; Plant Extracts; Plants, Medicinal; Terpenes

We aimed to compare the estrogenic activities of compounds isolated from Moutan Cortex Radicis (MRC, Paeonia suffruticosa Andrews) and identify their potential use in hormone replacement therapy. We quantified seven marker components (gallic acid, oxypaeoniflorin, paeoniflorin, ethyl gallate, benzoic acid, benzoylpaeoniflorin, and paeonol) in MRC using a high-performance liquid chromatography simultaneous analysis assay. To investigate the estrogenic activity of MRC and the seven marker components, an E-screen assay was conducted using the estrogen receptor (ER)-positive MCF-7 human breast cancer cell line. Among them, ethyl gallate caused cell proliferation in a concentration-dependent manner at concentrations above 25 µM and was clearly suppressed by combination treatment with the ER antagonist ICI 182,780. Therefore, ethyl gallate may be a compound of MRC that can increase the estrogenic effect in ER-positive MCF-7 cells.

Topics: Cell Line, Tumor; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Estrogens; Estrone; Gallic Acid; Glucosides; Hormone Replacement Therapy; Humans; Monoterpenes; Paeonia; Protein Binding; Structure-Activity Relationship

To prepare porosity osmotic pump tablets of total glucosides of paeony( TGP),and to study the behavior on synchronous release of its main components.. Taking the accumulative release of TGP as indexes, through single-factor test and orthogonal design to investigate the optimal formulation porosity osmotic pump tablets of TGP. The main components, paeoniflorin, albiflorin and benzoylpaeoniflorin were employed to study synchronous release of the optimal formulation.. The membrane weight, and the content of PEG 400,and diethyl phthalate( DEP) were the main factors influencing the behavior of TGP release. The accumulated release of the prepared osmotic pump release tablets achieved about 90%. Three main components achieved the desired zero-order release profile and had a synchronized release behavior.. The prepared porosity osmotic pump tablets of TGP can achieve the behavior of synchronized release of multi-components with good reproducibility.

Topics: Bridged-Ring Compounds; Delayed-Action Preparations; Glucosides; Monoterpenes; Osmosis; Paeonia; Polyethylene Glycols; Porosity; Reproducibility of Results; Solubility; Tablets

Monoterpenoids with "cage-like" pinane skeleton are the unique and main bioactive constituents in peony root, the root of Paeonia lactiflora. A liquid chromatography coupled with ion trap and time-of-flight mass spectrometry (LC-IT-TOF-MS) method was developed for characterization and quantification of monoterpenoids in different types of peony root and the roots of related Paeonia species. MS/MS fragmentation patterns of monoterpenoids with paeoniflorin-, albiflorin- and sulfonated paeoniflorin-type of skeletons were elucidated, which provided basic clues enabling subsequent identification of 35 monoterpenoids in LC-MS profiles of Paeonia species. The profiling analysis and further quantification of 15 main monoterpenoids in 56 samples belonged to red peony root (RPR), white peony root (WPR), peony root in Japanese market (PR) and the roots of related Paeonia species revealed that paeoniflorin, benzoylpaeoniflorin, galloylpaeoniflorin, oxypaoniflorin and albiflorin were predominant constituents in all the samples; mudanpioside C was the characteristic component of P. lactiflora, and 4-O-methyl-paeoniflorin was only detected in P. veitchii and P. anomala. Total contents of the 15 monoterpenoids were obviously higher in the roots of P. lactiflora and P. veitchii than in those of P. anomala and P. japonica. Principal component analysis based on the quantitative results showed that the samples derived from P. lactiflora were clearly classified into RPR, WPR/PR, and sulfur-fumigated WPR groups, besides the respective group of P. veitchii and P. anomala. This study clarified the chemical characteristics of the respective type of peony root and the related Paeonia species, as well as the marker constituents for their discrimination.

Topics: Bridged Bicyclo Compounds, Heterocyclic; Bridged-Ring Compounds; Chromatography, Liquid; Drugs, Chinese Herbal; Glucosides; Monoterpenes; Paeonia; Plant Roots; Tandem Mass Spectrometry

In this work, a simple and efficient protocol for the rapid separation of two pairs of isomeric monoterpenes from Paeoniae Alba Radix was developed by combining macroporous resin and elution-extrusion counter-current chromatography. The crude extract was firstly subjected to a D101 macroporous resin column eluted with water and a series of different concentrations of ethanol. Then, effluents of 30 and 95% ethanol were collected as sample 1 and sample 2 for further counter-current chromatography purification. Finally, a pair of isomers, 96 mg of compound 1 and 48 mg of compound 2 with purities of 91.1 and 96.2%, respectively, was isolated from 200 mg of sample 1. The other pair of isomers, 14 mg of compound 3 and 8 mg of compound 4 with purities of 93.6 and 88.9%, respectively, was isolated from 48 mg of sample 2. Their purities were analyzed by high-performance liquid chromatography, and their chemical structures were identified by mass spectrometry and (1) H NMR spectroscopy. Compared to a normal counter-current chromatography separation, the separation time and solvent consumption of elution-extrusion counter-current chromatography were reduced while the resolutions were still good. The established protocol is promising for the separation of natural products with great disparity of content in herbal medicines.

Topics: Bridged-Ring Compounds; Chromatography; Chromatography, High Pressure Liquid; Countercurrent Distribution; Ethanol; Glucosides; Glycosides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Monoterpenes; Paeonia; Plant Preparations; Solvents; Ultrasonography

The methanol extract of the root cortex of Paeonia suffruticosa afforded two new monoterpene glycosides, paeoniside A (1) and paeoniside B (2), and three known monoterpene glycosides, paeoniflorin (3), benzoylpaeoniflorin (4) and 4-O-methyl-paeoniflorin (5). Their structures were elucidated on the basis of spectroscopic means including 1D and 2D NMR experiments. Compounds 1-5 were found to be active against cyclooxygenase-1 and cyclooxygenase-2 enzymes.

Topics: Anti-Inflammatory Agents; Cyclooxygenase 1; Cyclooxygenase 2; Cyclooxygenase Inhibitors; Drugs, Chinese Herbal; Glucosides; Glycosides; Molecular Structure; Monoterpenes; Nuclear Magnetic Resonance, Biomolecular; Paeonia; Plant Roots

In this study, a improved high performance liquid chromatography-diode array detector (HPLC-DAD) method for simultaneous quantification of twelve major components belonging to three chemical types was developed and validated, and was applied to quantitatively compare the quality of Radix Paeoniae Alba (RPA) sulfur-fumigated with different durations and purchased from commercial herbal markets. The contents of paeoniflorin, benzoylpaeoniflorin, oxypaeoniflorin, benzoic acid and paeonol decreased whereas that of paeoniflorin sulfonate increased in RPA with the extending of sulfur-fumigation duration. Different levels of paeoniflorin sulfonate were determined in ten of seventeen commercial RPA samples, indicating that these ten samples may be sulfur-fumigated with different durations. Moreover, the relative standard deviation of the contents of each component was higher in the commercial sulfur-fumigated RPA samples than that in commercial non-fumigated RPA samples, and the percentage of the total average content of monoterpene glycosides in the determined analytes was higher in the decoctions of commercial sulfur-fumigated RPA than that in commercial non-fumigated RPA samples. All these results suggested that the established method was precise, accurate and sensitive enough for the global quality evaluation of sulfur-fumigated RPA, and sulfur-fumigation can not only change the proportions of bioactive components, but also cause the reduction of the quality consistency of both raw materials and aqueous decoctions of RPA.

Topics: Acetophenones; Benzoic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Fumigation; Glucosides; Glycosides; Herbal Medicine; Monoterpenes; Paeonia; Plant Roots; Sulfur

A variety of traditional Chinese medical formulations contain two or more herbs from the same genus or family. Although these herbs may have a similar appearance and constituents, they usually have different pharmacodynamic actions. A series of qualitative and quantitative analysis methods are developed to determine one or more compounds for quality control of medicine. As far as we know, no method has been found to determine the real ratio of the two herbs along with the prescription. In this study, we used HPLC-DAD as a way to determine the content of Moutan cortex (M) and Paeoniae radix alba (P) in GuizhiFuling Wan (GZFLW). An effective, accurate and reliable HPLC-DAD method was developed for detecting the content of M and P in GZFLW through the analysis of four monoterpeneglycosides, namely, galloylpaeoniflorin (1), paeoniflorin (2), mudanpioside C (3) and benzoylpaeoniflorin (4). Due to the different UV characteristics of the compounds, the detection wavelength was 270 nm for 1 and 2, while 3 and 4 were monitored at 254 nm and 230 nm, respectively. Four equations were put forward to describe the relationship between content of M as well as P and the four monoterpene glycosides in GZFLW. After validation, all the accuracies of the M and P contents in GZFLW were within 10%. The result showed that the method could be successfully applied to analyze the contents of M and P in GZFLW. Moreover, our method may be more widely used to control the quality of proprietary Chinese medicines, especially for those containing the same genus or family herbs, in industrial GMP production.

Topics: Bridged Bicyclo Compounds, Heterocyclic; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucosides; Glycosides; Medicine, Chinese Traditional; Monoterpenes; Paeonia; Plant Roots

Three new monoterpene glycosides named 4-O-methyl-paeoniflorin (1), isopaeoniflorin (2), and isobenzoylpaeoniflorin (3), together with two known monoterpene glycosides, paeoniflorin (4) and benzoylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora. Their structures were established on the basis of spectral and chemical evidence.

Topics: Benzoates; Bridged-Ring Compounds; Glucosides; Glycosides; Monoterpenes; Paeonia; Plant Roots; Vietnam

A complex formula composed of Paeonia lactiflora PALL. and Glycyrrhiza uralensis Fisch., which is called as Jakyak-Gamcho Decoction (JGD), has been used for a pain-relieving function and muscle spasms due to blood deficiency in the traditional medicine. In this study, the anti-inflammatory activity of JGD was evaluated based on the quantitative determinations and the relative proportions of six major constituents in the decoction mixture extracted by orthogonal array methods. Our results suggest that the three parameters are all crucial factors. The optimized conditions for extraction were therefore established [solvent (water); pH value (4); extraction number (4)]. We also optimized the extraction conditions related to anti-inflammatory activity [solvent (70% EtOH); pH value (6); extraction number (4)]. So, we found that the bioactivity was responsible for mixed components but not individual one. It was proportionally associated with the amounts of some components in the extracts of herbal medicines. When the proportion of the active components was similar to each other, they had the similar functions. Furthermore, the results could establish a model system for the quality assurance of herbal preparations, and provided a new paradigm of active components-pharmacodynamics, which is used for illustrating the connections between the bioactivities and the proportion of active constituents in the extracts of herbal medicines.

Topics: Alkaline Phosphatase; Animals; Benzoates; Bridged-Ring Compounds; Cell Line; Cell Survival; Chalcone; Chemical Fractionation; Chromatography, High Pressure Liquid; Ethanol; Flavanones; Glucosides; Glycyrrhiza; Glycyrrhizic Acid; Herbal Medicine; Lipopolysaccharides; Macrophages; Monoterpenes; NF-kappa B; Nitric Oxide; Paeonia; Plant Extracts; Research Design; Solubility; Technology, Pharmaceutical; Water

A new monoterpene glycoside, 6'-O-beta-D-glucopyranosylalbiflorin (1), and four known compounds; albiflorin (2), 6'-O-benzoylalbiflorin (3), paeoniflorin (4) and benzoyl paeoniflorin (5), were isolated from the methanolic extract of the roots of Paeonia lactiflora Pall.. Their chemical structures were completely elucidated using a combination of 2D NMR techniques (COSY, HMQC and HMBC) and HRESI-MS analyses. To investigate the bioactivities of these compounds, their effects on the differentiation of osteoblastic MC3T3-E1 cells were tested. Compound 1 (0.01-10 microM) significantly increased the alkaline phosphatase activity and nodules mineralization of MC3T3-E1 cells compared to those of the control (P<0.05). These results suggest that newly isolated compound 1 has a direct stimulatory effect on bone formation in vitro and may contribute to the prevention for osteoporosis.

Topics: Alkaline Phosphatase; Animals; Benzoates; Bone Density Conservation Agents; Bridged-Ring Compounds; Calcification, Physiologic; Cell Differentiation; Cell Line; Dose-Response Relationship, Drug; Glucosides; Glycosides; Magnetic Resonance Spectroscopy; Mice; Molecular Structure; Monoterpenes; Osteoblasts; Paeonia; Plant Extracts; Plant Roots; Spectrometry, Mass, Electrospray Ionization; Vietnam