neomangiferin and mangiferin

This work presents a greener approach for simultaneous determination of neomangiferin and mangiferin, the major bioactive constituents with severe spectral overlapping in Anemarrhenae Rhizoma, combining the sensitivity of molecular fluorescence and the selectivity of chemometric multivariate calibration algorithms. In this study, we compared the analytical performance of two group chemometric algorithms including trilinear algorithms such as parallel factor analysis (PARAFAC), alternating trilinear decomposition (ATLD), self-weighted alternating trilinear decomposition (SWATLD) and alternating penalized trilinear decomposition (APTLD), and PLS-based methods such as unfolded partial least-squares or the multi-dimensional partial least-squares, both combined with residual bilinearization (U-PLS/RBL, N-PLS/RBL). The statistical parameters for the validation set of the second calibration were evaluated through the relative error of prediction (REP%), the average recovery (Rec%), and the root mean square error of prediction (RMSEP). Prediction results for the validation set by trilinear algorithms showed that the values were satisfactory for neomangiferin, and higher and not acceptable values for mangiferin, while U-PLS and N-PLS predictions were very successful for two analytes. Therefore, U- and N-PLS/RBL were chosen to determine neomangiferin and mangiferin in more complex real samples simultaneously, and U-PLS/RBL algorithm showed the best performance. The predicted concentrations by proposed methods were satisfactorily compared with those obtained using high performance liquid chromatography with ultraviolet detection.

Topics: Algorithms; Anemarrhena; Calibration; Chromatography, High Pressure Liquid; Factor Analysis, Statistical; Glucosides; Least-Squares Analysis; Reference Standards; Reproducibility of Results; Solutions; Xanthones

In this study, a sensitive and rapid ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was developed to determine mangiferin and neomangiferin in rat plasma simultaneously. Chromatographic separation was carried out on an Acquity UPLC BEH C18 column and mass spectrometric analysis was performed using a Xevo TQD triple quadruple mass spectrometer coupled with an electrospray ionization (ESI) source. The MRM transitions of m/z 423.2 → 303.1 and m/z 585.0 → 273.1 were used to quantify for mangiferin and neomangiferin, respectively. The linearity of this method was found to be within the concentration range of 5-2000 ng/mL for mangiferin, and 2-1000 ng/mL for neomangiferin in rat plasma, respectively. Only 3.0 min was needed for an analytical run. This assay was used to support a preclinical study to investigate the pharmacokinetics of mangiferin and neomangiferin in rats.

Topics: Animals; Chromatography, Liquid; Glucosides; Male; Rats; Rats, Sprague-Dawley; Reference Standards; Tandem Mass Spectrometry; Xanthones

Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

Topics: Biological Products; Cyclization; Glucosides; Glycosylation; Lewis Acids; Phloroglucinol; Stereoisomerism; Xanthones

tive: To compare and analyze the quality of Anemarrhena asphodeloides rhizome from different habitats.. Simultaneous determination of nine components in Anemarrhena asphodeloides rhizome by UPLC-TQ/MS was performed on a Phenomenex Kinetex XB-C18 (100 mm x 2.1 mm, 1.7 μm) column with the mobile phase consisted of 0.1% formic acid-acetonitrile (gradient elution) at the flow rate of 0.4 mL/min and thecolumn temperature at 35 degrees C. Multiple reaction mode detection (MRM) in mode was used in this assay.. Nine components were separated totally within 15 min. Good correlation were found between the investigated compounds concentrations and their peak areas within the test ranges with the correlation coefficient from 0.9917 to 0.9992. The average recoveries were from 98.1% to 103.7%, and the RSD of precision was in the range of 1.7% - 4.7%. 0.074-3.620 mg/g for sarsasapogenin, 0.042-2.530 mg/g for timosaponin A III, 22.1- 50.4 mg/g for timosaponon B II, 0.10 -8.28 mg/g for officinalisinin II, 0.64 -7.29 mg/g for anemarsaponin B III, 3.28 -27.40 mg/g for mangiferin, 1.83 - 7.21 mg/g for isomangiferin, 0.36 -9.25 mg/g for neomangiferin and 4.72 x 10(-5) - 1.38 x 10(-3) mg/g for baohuoside I in Anemarrhena asphodeloides rhizome from different habitats were detected.. The method is rapid, accurate and can be used for quality evaluation of Anemarrhena asphodeloides rhizome. The quality of Anemarrhena asphodeloides rhizome from different habitats are different. The saponins content of Anemarrhena asphodeloides rhizome in Hebei is higher than that of the others.

Topics: Anemarrhena; Drugs, Chinese Herbal; Ecosystem; Glucosides; Plant Extracts; Plants, Medicinal; Rhizome; Saponins; Spirostans; Steroids; Triterpenes; Xanthones

Diabetic ophthalmopathy (DO) impairs patients' eyesight and even causes blindness. Here, we investigated the effect of 60% ethanol extract of the rhizome of Anemarrhenae asphodeloides (ERA), which is commonly used in Chinese medicine formulae in treating diabetes, on DO progression. Blood glucose, insulin, advanced glycation end products (AGE), super oxygen dehydrogenises (SOD), malondialdehyde (MDA) and glutathione peroxidase (GSH-Px) levels in serum and sorbitol concentration in the lens were measured. Retinal endothelium/pericyte (E/P) ratio was evaluated, and structural changes of the retina and lens were observed. Effects of mangiferin and neomangiferin, the two major components of ERA, on subnormal growth of pericytes induced by high glucose were also detected. It was found that the activities of SOD and GSH-Px in serum were increased, whereas MDA and AGE levels in serum and sorbitol concentration in the lens were decreased in ERA-treated DO rats. E/P ratio was decreased, and the pathological changes of the lens and retina were alleviated by ERA treatment. Moreover, the subnormal growth of pericytes induced by high glucose was ameliorated by mangiferin and neomangiferin. These results indicated that ERA could effectively prevent DO progression in streptozotocin-induced diabetic rats, and mangiferin and neomangiferin may be the main effective components.

Topics: Anemarrhena; Animals; Blood Glucose; Cataract; Diabetes Mellitus, Experimental; Diabetic Retinopathy; Glucosides; Glutathione Peroxidase; Glycation End Products, Advanced; Insulin; Lens, Crystalline; Male; Malondialdehyde; Pericytes; Plant Extracts; Rats; Rats, Wistar; Retina; Rhizome; Sorbitol; Streptozocin; Superoxide Dismutase; Xanthones

A high performance liquid chromatographic (HPLC) method has been developed for the simultaneous determination of neomangiferin, mangiferin, timosaponin B III, anemarrhenasaponin I and timosaponin A III in the products of Anemarrhena asphodeloides Bge. processed by different methods. By comparing and analyzing the variation of the contents of the five components, the effects of processing on chemical constituents of Anemarrhena asphodeloides Bge. were explored, which provided evidences for the relevance between processing and the property changes of Anemarrhena asphodeloides Bge. The chromatographic separation was performed on an Alltima C18 column (250 mm x 4.6 mm, 5 microm) with a gradient elution of acetonitrile (A) and 0. 1% formic acid (B) (0 - 10 min, 5% A - 20% A; 10 - 15 min, 20% A - 25% A; 15 -30 min, 25% A - 80% A; 30 -35 min, 80% A - 100% A) at a flow rate of 0.8 mL/min. Neomangiferin and mangiferin were detected by an ultraviolet detector at 265 nm and room temperature. Timosaponin B III, anemarrhenasaponin I and timosaponin A III were detected by an evaporative light scattering detector with the drift temperature at 50 degrees C and gas pressure at 179.1 kPa (26 psi). To some extent, the contents of the major components varied in different processed products of Anemarrhena asphodeloides Bge. The results indicated that different processing methods caused significant differences in the contents of the major components of Anemarrhena asphodeloides Bge. It is of great use for further researching the relevance of the processing methods to pharmacodynamics of Anemarrhena asphodeloides Bge.

Topics: Anemarrhena; Chromatography, High Pressure Liquid; Glucosides; Saponins; Xanthones

A preparative high-speed countercurrent chromatography method for isolation and purification of neomangiferin and mangiferin from Rhizoma anemarrhenae was successfully established by using ionic liquids as the modifier of the two-phase solvent system. Neomangiferin and mangiferin were purified from the crude extract of R. anemarrhenae by using ethyl acetate-water-[C(4)mim][PF(6)] (5:5:0.2 v/v) as two-phase solvent system. In total, 22.5 mg of neomangiferin and 70.6 mg of mangiferin were obtained from 150 mg of the crude extract. The purities of neomangiferin and mangiferin were 97.2 and 98.1%, respectively, as determined by HPLC. The chemical structures of the isolated compounds were identified by (1)H-NMR and (13)C-NMR.

Topics: Countercurrent Distribution; Drugs, Chinese Herbal; Glucosides; Ionic Liquids; Molecular Structure; Solvents; Xanthones

A sensitive and reliable liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) has been developed and validated for simultaneous determination of active components, i.e., xanthone glycosides (neomangiferin and mangiferin), timosaponins (timosaponin E1, timosaponin B-II and timosaponin B) and alkaloids (palmatine and berberine) in rat plasma after oral administration of Zi-Shen Pill extract. Plasma samples were pretreated by protein precipitation with acetonitrile containing the internal standards ginsenoside Re (for xanthone glycosides and timosaponins) and tetrahydroberberine (for alkaloids). LC separation was achieved on a Zorbax SB-C(18) column (150 mm x 2.1 mm I.D., 3.5 microm) with gradient elution using a mobile phase consisting of acetonitrile-0.1% formic acid in water at a flow rate of 0.25 mL/min. The detection was carried out by a triple-quadrupole tandem mass spectrometer in multiple reaction monitoring (MRM) mode via polarity switching between negative (for xanthone glycosides and timosaponins) and positive (for alkaloids) ionization mode. Linear calibration curves were obtained over the concentration range of 5-1000 ng/mL for mangiferin, 0.5-100 ng/mL for neomangiferin, timosaponin E1, timosaponin B-II and timosaponin B, and 0.05-10 ng/mL for palmatine and berberine. The mean recovery of all the analytes ranged from 64.7 to 93.8%. The intra- and inter-day precision (% R.S.D.) was within 11.7% and accuracy (% bias) ranged from -9.0 to 10.9%. This fully validated method was successfully applied to pharmacokinetic study of the above seven compounds in rats.

Topics: Animals; Chromatography, Liquid; Drug Stability; Drugs, Chinese Herbal; Glucosides; Linear Models; Male; Rats; Rats, Sprague-Dawley; Reproducibility of Results; Saponins; Sensitivity and Specificity; Steroids; Tandem Mass Spectrometry; Xanthones

An efficient on-line purity monitoring strategy based on on-line coupling of high-speed counter-current chromatography (HSCCC) with high-performance liquid chromatography-diode array detection (HPLC-DAD) was successfully applied for the first time to the isolation and purification of 5-hydroxymethyl-furancarboxaldehyde (5-HMF), mangiferin and neomangiferin from the Chinese medicinal plant Anemarrhena asphodeloides Bunge, a plant used in the traditional Chinese medicine. The introduction of on-line purity monitoring in HSCCC has greatly improved the efficiency of this technique by overcoming the drawbacks of post-purification sample handling in HSCCC isolation. The effluent from the outlet of HSCCC was split into two parts, and one was collected, while the other was introduced directly through a switch valve into a HPLC-DAD system for purity monitoring. Using this method the desired fractions with high purities could be collected. From 600 mg partially purified extract, 165.6 mg neomangiferin and 292.8 mg mangiferin with purities of 98.9 and 99.5%, respectively, were obtained with a two-phase solvent system composed of n-butanol-water (1:1, v/v) by increasing the flow-rate of the mobile phase stepwise from 1.0 to 2.2 ml min(-1) after 210 min. A 17.1mg 5-HMF with purity of 96.6% was also isolated for the first time.

Topics: Anemarrhena; Chromatography, High Pressure Liquid; Countercurrent Distribution; Drugs, Chinese Herbal; Furans; Glucosides; Plant Extracts; Plants, Medicinal; Xanthones

Xilingzhimu, the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae), has been prescribed as antipyretic, anti-inflammatory, diuretic and hypoglycemic agents in Chinese traditional medicine. In this paper, two xanthone glycosides I and II, were isolated from Xilingzhimu by conventional method. The structures of I and II were identified on the basis of chemical reactions and UV, IR, 1HNMR, 13CNMR and DEPT. Compound I was identified as mangiferin and II is a new compound, named neomangiferin. Its structure is 7-O-beta-D-glucopyranosyl-mangiferin.

Topics: Glucosides; Liliaceae; Molecular Structure; Plant Roots; Plants, Medicinal; Xanthenes; Xanthones