OBJECTIVETo study the chemical constituents of the rhizome of Matteuccia struthiopteris.

METHODThe constituents were separated and purified by column chromatography with silica gel and Sephadex LH-20. Their structures were identified on the basis of physical and spectral data.

RESULTSix compounds were isolated and identified as demethoxymatteucinol (1), matteucinol (2), pinosylvin (3), matteuorien (4), pinosylvin 3-O-beta-D-glucopyranoside (5), matteuorienate A (6).

CONCLUSIONAll Compounds were isolated from this plant for the first time.

Chromones ; chemistry ; Dryopteridaceae ; chemistry ; Flavonoids ; chemistry ; Glucosides ; chemistry ; Magnetic Resonance Spectroscopy ; Rhizome ; chemistry ; Stilbenes ; chemistry

To prepare beta-cyclodextrin (beta-CD)-deoxyrhaponti inclusion complex by the homogeneous method, and characterize the inclusion complex with ultraviolet-visible spectrum and fluorescence spectroscopy, in order to determine the inclusion rate, the ratio of subject-object, the binding constant of supra-molecular system and the thermodynamic function. The results showed that the designed method was so rational that the inclusion complex was successfully prepared. The ultraviolet-visible spectrophotometry method was adoptedto determine the inclusion rate of 38%, and the ratio of subject-object of 2: 1. The thermodynamic parameters of this inclusion complex: deltaH(0), deltaS(0) was all smaller than zero, which indicated that the main acting forces generated by the inclusion complex were hydrogen bonding and Vander Waals' force. deltaG(0) < 0 and deltaG(0) were directly proportional to the reaction temperature, which suggested that the reaction would spontaneously increase with the temperature rise. The polarization fluorescence method was used to quantitatively prove the non-covalent inclusion complex generated during the interaction between beta-CD interacting with DES. The results could also provide reference for studies on cyclodextrin supra-molecular system.
Drug Carriers ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Nanoparticles ; chemistry ; Stilbenes ; chemistry ; beta-Cyclodextrins ; 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

Resveratrol is a naturally occurring stilbene, a kind of polyphenolic compounds, found in a limited number of plant species such as grape, peanut, and pine. It has been considered as a phytoalexin in plants, and many studies have also shown its health benefits such as antioxidant activities, cancer prevention, blood thinning, and life span extension. This paper reviews the characteristics of resveratrol in aspects of synthesis, extraction, purification, and determination. In particular, the new outcomes of physiology function and the transgenic approaches have been presented. The challenges and chances for genetic engineering and health-related industries were also discussed.
Genetic Engineering ; Plants ; chemistry ; Stilbenes ; chemical synthesis ; metabolism ; pharmacology

OBJECTIVETo compare of the contents of two stilbene glycoside in five processed products of Rheum palamatum.

METHODThe contents of trans-3, 5, 4'-trihydroxystilbene-4'-O-beta-D-glucopyranoside (a) and trans-3, 5, 4'-trihydroxystilbene-4'-Obeta-D-(6"-O-galloyl)-glucopyranoside (b) were determined by HPLC analysis at 35 degrees C with methanol-1% acetic acid as mobile phase, the wavelengths were set at 280, 300 nm, the flow rate was 1.0 mL x min(-1).

RESULTThe two components could be detected in five processed products, and their contents were more close in the no-parched pieces, the vinegar roasts pieces and the wine roast pieces. However, the contents reduced significantly in other two kinds of pieces which were lower than 80 percent of no-parched pieces.

CONCLUSIONHigh temperature may result in a significant reduction on glycoside in the pieces of rhubarb, and we have received similar results from determination of other glycoside compounds. Further analysis and comparison with the content of their corresponding aglycones, can provide a scientific basis to explain the variation of the material basis in the processed products of rhubarb.

Glycosides ; analysis ; Plant Extracts ; analysis ; Rheum ; chemistry ; Stilbenes ; analysis

OBJECTIVETo compare the contents of stilbenes in different parts and axial root bark of mulberry, and study their correlation.

METHODThe contents of 3 major stilbenes, mulberroside A, oxyresveratrol, and resveratrol in different parts of mulberry were determined by HPLC. The correlation and regression analysis between the contents of stilbenes in the different parts and axial root bark was carried out.

RESULTThe contents of stilbenes in most different parts of mulberry showed significant correlation. Between the contents of stilbenes in the different parts and axial root bark, oxyresveratrol showed significant correlation among all different parts, resveratrol showed significant correlation except in spinal cord of annual branch, mulberroside A showed significant correlation between bark of annual branch, lateral root and axial root bark. The results of the correlation and regression analysis indicated that the contents of mulberroside A, oxyresveratrol, resveratrol in different parts and axial root bark were significant positively correlated.

CONCLUSIONThe contents of stilbenes are significant correlation distributed in different parts and axial root bark of mulberry. The contents of stilbenes in different parts could be used to estimate the content of the axial root bark. The result could be useful for breeding and preserving excellent germplasm at the system breed process for mulberry of rich in stilbenes.

Chromatography, High Pressure Liquid ; Disaccharides ; chemistry ; Morus ; chemistry ; Plant Roots ; chemistry ; Stilbenes ; chemistry

AIMTo study the chemical constituents of Dryopteris sublaeta Ching et Hsu.

METHODSFresh plant of Dryopteris sublaeta ching et hsu was extracted twice with boiling water, concentrated to small volume under reduced pressure at 50 degrees C. The concentrated material was partitioned with ether, ethyl acetate, and n-butanol. The fraction of ethyl acetate extract was chromatographed over macroporous adsorption resin (Diaion HP-20) eluted with a mixture of H2O and MeOH in increasing MeOH content. Their fractions from resin were repeatedly chromatographed over Toyopearl HW-40, Sephadex LH-20 and silica gel column chromatography. The compounds were identified on the basis of their physiochemical and spectral data.

RESULTSFour compounds were obtained and identified as 3,5-dihydroxy-stilbene-3-O-neohesperidoside (1), 3,5-dihydroxy-stilbene-3-O-beta-D-glucoside (2), polydotin peceid (3) and 3,5,4'-trihydroxy-bibenzyl-3-O-beta-D-glucoside (4).

CONCLUSIONCompound 1 is a new compound, the others were isolated from Dryopteris for the first time.

Dryopteris ; chemistry ; Glycosides ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Stilbenes ; chemistry ; isolation & purification

Decoction is one of the most commonly used dosage forms of traditional Chinese medicine. The stability of chemical constituents in decoction is closely related to the clinical efficacy and safety. There were few reports about the influence of metal ions in the stability of chemical constituents in traditional Chinese medicine. However, there is no evidence that metal ions in decoction water need to be controlled. In this study, 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside (THSG), one of the main constituents in Polygoni Multiflori Radix was studied. Ordinary tap water, deionized water, and water containing different metal ions were used to investigate and compare the influence on THSG. The results showed that after storage in a dark place at the room temperature for 10 days, the degradation of THSG was 7% in deionized water, while undetectable in tap water. The content of THSG could be decreased by different kinds of metal ions, and the effect was concentration-dependent. Moreover, Fe3+ and Fe2+ showed the greatest influence at the same concentration; and our study has shown that THSG decreased more than 98% in Fe and Fe2+ solutions at 500 ppm concentration. In the same time we found out p-hydroxybenzaldehyde (molecular weight: 122.036 7) and 2,3,5-trihydroxybenzaldehyde-2-O-glycoside (molecular weight: 316.079 4) were the main degradation products of THSG in tap water and water containing Cu2+, Ca2+, Zn2+, Mg2+ and Al3+. The product of THSG dimer with a water molecule was found in water containing Fe3+ and Fe2+. The above results showed that the metal ions in water could significantly influence the stability of THSG in water, indicating that the clinical efficacy and safety of decoction would be affected if the metal ions in water were not under control. It's suggested that deionized water should be used in the preparation of decoction containing Polygoni Multiflori Radix in the clinic to avoid degradation of THSG. Meanwhile, decoction prepared by tap water should be taken by patients in a short time. Our investigation provides important information and reference about the influence of metal ions on the stability of decoctions in other traditional Chinese medicine that have unstable groups such as hydroxyls and unsaturated bonds, etc.
Drugs, Chinese Herbal ; chemistry ; Glucosides ; chemistry ; Ions ; chemistry ; Metals ; chemistry ; Plant Roots ; chemistry ; Polygonaceae ; chemistry ; Stilbenes ; chemistry

The objectives of this study are to prepare resveratrol loaded mixed micelles composed of poloxamer 403 and poloxamer 407, and optimize the formulation in order to achieve higher drug solubility and sustained drug release. Firstly, a thin-film hydration method was utilized to prepare the micelles. By using drug-loading, encapsulation yield and particle size of the micelles as criteria, influence of three variables, namely poloxamer 407 mass fraction, amount of water and feeding of resveratrol, on the quality of the micelles was optimized with a central composite design method. Steady fluorescence measurement was carried out to evaluate the critical micelle concentration of the carriers. Micelle stability upon dilution with simulated gastric fluid and simulated intestinal fluid was investigated. The in vitro release of resveratrol from the mixed micelles was monitored by dialysis method. It was observed that the particle size of the optimized micelle formulation was 24 nm, with drug-loading 11.78%, and encapsulation yield 82.51%. The mixed micelles increased the solubility of resveratrol for about 197 times. Moreover, the mixed micelles had a low critical micelle concentration of 0.05 mg · mL(-1) in water and no apparent changes in particle size and drug content were observed upon micelles dilution, indicating improved kinetic stability. Resveratrol was released from the micelles in a controlled manner for over 20 h, and the release process can be well described by Higuchi equation. Therefore, resveratrol-loaded poloxamer 403/407 mixed micelles could improve the solubility of resveratrol significantly and sustained drug release behavior can be achieved.
Drug Carriers ; chemistry ; Fluorescence ; Kinetics ; Micelles ; Particle Size ; Poloxamer ; chemistry ; Solubility ; Stilbenes ; chemistry ; Water

The supramolecular inclusion properties of beta-cyclodextrin (beta-CD) and resveratrol (Res) were investigated using drug-protein interaction spectroscopy method. The differences between the results of interaction spectroscopy method and the results of classical method were compared. The total energy of the stable inclusion of cyclodextrin-resveratrol was calculated by Gaussian theory calculation. The stable inclusions in the process of interaction between resveratrol/inclusion complex and bovine lactgoferrin (BLF) were studied by molecular modeling. The results showed that the interaction spectroscopy method could explain the property of the inclusion in a more sensitive manner, it also interpreted the conveying mechanism of BLF binding with inclusion complex. The molecular modeling result showed consistent results with Gaussian theory calculation; both of the two methods obtained the stable configuration of beta-CD-Res inclusion. The relevant result provided an experimental consequence for the pharmacology research of beta-cyclodextrin-resveratrol inclusion complex as well as offering a new reference to the future research of supramolecular inclusion compound.
Animals ; Cattle ; Lactoferrin ; chemistry ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Stilbenes ; chemistry ; beta-Cyclodextrins ; chemistry