A new dibenzocyclooctadiene lignan, renchangianin E (1) was isolated from the stems of Kadsura renchangiana. Its structure and stereochemistry were elucidated by spectroscopic methods, including 2D-NMR techniques.
Cyclooctanes ; chemistry ; Kadsura ; chemistry ; Lignans ; chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure

OBJECTIVETo determine lignan content in the vine stem of Schisandra chinensis during 12 months and provide the scientific basis for the development and utilization of the resources.

METHODAnalysis was carried out on an Eclipse XDB C18 column eluted with a mixture of methanol-acetonitrile-water (43: 28: 29) as the mobile phase. The flowrate was 1.0 mL x min(-1), and the detection wavelength was set at 250 nm. Schisandrin, deoxyschizandrin and schisandrin B were used as reference substance, and the external standard method was used.

RESULTThe content of three constituents in the vine stem varied under different months. Schisandrin's maximum is 2.3 mg x g(-1) in December, minimum is 1.4 mg x g(-1) in April. A Deoxyschizandrin's maximum is 0.8 mg x g(-1) in November, minimum is 0.4 mg x g(-1) in March; Schisandrin B's maximum is 3.0 mg x g(-1) in January, minimum is 1.1 mg x g(-1) in April.

CONCLUSIONThe collection seasons for the vine stem of S. chinensis are autumn and winter.

Chromatography, High Pressure Liquid ; Cyclooctanes ; chemistry ; Lignans ; chemistry ; Plant Stems ; chemistry ; Polycyclic Compounds ; chemistry ; Schisandra ; chemistry

OBJECTIVETo investigate the quality of Schisandra chinensis, and thus provide the useful reference data for its quality standard establishment and standardized cultivation.

METHODBase on the Chinese Pharmacopoeia and literature relating to S. chinensis, the appearance, water-soluble extractive, total ash, acid-insoluble ash and volatile oil of 10 S. chinensis sampes collected from different producing sites in northeast China were studied or determined, and the contents of major active lingans were measured by HPLC.

RESULTThe content of total ash and acid-insoluble ash in S. chinensis was less than 7.0%, 1.0%, respectively. The contents of water-soluble extractive were higher than 45.0%. HPLC analyses showed that the content of schisandrol A was higher than 0.40%. All these results in accordance with the requirements of Chinese Pharmacopoeia were published in 2010.

CONCLUSIONThe differences of the appearance and the internal quality are different for the samples collected from different areas. And the establishment of a scientific and comprehensive quality standard system will be very important role in ensuring the quality of S. chinensis.

China ; Cyclooctanes ; analysis ; Drugs, Chinese Herbal ; analysis ; standards ; Lignans ; analysis ; Oils, Volatile ; analysis ; Quality Control ; Schisandra ; chemistry ; growth & development

In the current study, schisandrin B(SchB)-loaded F127 modified lipid-polymer hybrid nanoparticles(SchB-F-LPNs) were developed to improve the inhibition of breast cancer lung metastasis. Modified nanoprecipitation method was used to prepare SchB-F-LPNs. The nanoparticles were spherical in shape with shell-core structure by TEM observation. SchB-F-LPNs showed a mean particle size of(234.60±6.11) nm with zeta potential of(-5.88±0.49) mV. XRD results indicated that SchB existed in the nanoparticles in an amorphous state. The apparent permeability coefficient through porcine mucus of F-LPNs was 1.43-fold of that of LPNs as shown in the in vitro mucus penetration study. The pharmacokinetics study showed that the C_(max) of SchB was(369.06±146.94) μg·L~(-1),(1 121.34±91.65) μg·L~(-1) and(2 951.91±360.53) μg·L~(-1) respectively in SchB suspensions group, SchB-LPNs group and SchB-F-LPNs group after oral administration in rats. With SchB suspensions as the reference formulation, the relative bioavailability of SchB-F-LPNs was 568.60%. SchB-F-LPNs inhibited the morphological change during transforming growth factor-β1(TGF-β1)-induced epithelial-mesenchymal transition. In addition, SchB-F-LPNs significantly decreased the number of metastatic pulmonary nodules in 4 T1 tumor-bearing mice, suggesting that SchB-F-LPNs may inhibit the metastasis of breast cancer. These results reveal the promising potential of SchB-F-LPNs in treatment of breast cancer lung metastasis.
Animals ; Cyclooctanes ; Lignans ; Lipids ; Lung Neoplasms/drug therapy* ; Mice ; Nanoparticles ; Polycyclic Compounds ; Polyethylenes ; Polymers ; Polypropylenes ; Rats ; Swine

The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chromatography using circular dichroism detection for the analysis of the stereochemistry. A new 6, 9-oxygen bridge dibenzocyclooctadiene lignans named Kadsulignan Q was firstly found with an S-biphenyl configuration. The other compound was identified as Kadsulignan L with an R- biphenyl configuration. In order to obtain kinetic data on their reversible interconversion, the stability was measured at different deuterated solvents such as deuterated methanol, deuterated chloroform and deuterated dimethylsulfoxide. The lignans were more unstable and converted more easily in deuterated methanol than in deuterated chloroform and deuterated dimethylsulfoxide.
Chromatography, High Pressure Liquid ; Circular Dichroism ; Cyclooctanes ; chemistry ; Kadsura ; chemistry ; Lignans ; chemistry ; Molecular Structure ; Oxygen ; Plant Extracts ; chemistry ; Stereoisomerism

Gomisin A possesses a hepatic function-facilitating property in liver-injured rats. Its preventive action on carbon tetrachloride-induced cholestasis is due to maintenance of the function of the bile acids-independent fraction. To investigate alterations in gene expression after gomisin A treatment on injured rat liver, DNA microarray analyses were performed on a Rat 44K 4-Plex Gene Expression platform with duplicated reactions after gomisin A treatment. We identified 255 up-regulated and 230 down-regulated genes due to the effects of gomisin A on recovery of carbon tetrachloride-induced rat liver damage. For functional characterization of these genes, Gene Ontology and Kyoto Encyclopedia of Genes and Genomes biochemical pathways analyses were performed. Many up-regulated or down-regulated genes were related to cell cycle or focal adhesion and cell death genes, respectively. Our microarray experiment indicated that the liver repair mechanism induced by gomisin A was strongly associated with increased gene expressions related to cell cycle and suppression of the gene expression related in cell death.
Animals ; Bile ; Carbon ; Carbon Tetrachloride ; Cell Cycle ; Cell Death ; Cholestasis ; Cyclooctanes ; Dioxoles ; Focal Adhesions ; Gene Expression ; Gene Expression Profiling ; Genome ; Lignans ; Liver ; Oligonucleotide Array Sequence Analysis ; Rats ; Transcriptome

AIMTo study the chemical constituents of Bletilla striata.

METHODSVarious column chromatographies with silica gel and Sephadex LH-20 were employed for the isolation and purification. The structures of the compounds were elucidated on the basis of spectral analyses and chemical methods.

RESULTSThree compounds were isolated from the roots of Bletilla striata (Thunb.) Reichb. f. and identified as 5-hydroxy-4-(p-hydroxybenzyl)-3'-3-dimethoxybibenzyl (I), schizandrin (II), 4,4'-dimethoxy-(1,1'-biphenanthrene)-2,2',7,7'-tetrol (III).

CONCLUSIONCompound I is a new bibenzyl derivative and II was isolated from this plant for the first time.

Bibenzyls ; chemistry ; isolation & purification ; Cyclooctanes ; chemistry ; isolation & purification ; Lignans ; chemistry ; isolation & purification ; Molecular Structure ; Orchidaceae ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Polycyclic Compounds ; chemistry ; isolation & purification

OBJECTIVETo determine the concentration of schisandrin in Shengmaiyin with HPLC.

METHODThe sample was extracted with ethyl acetate through supersonic wave. The solution was filtrated and evaporated. The residue was resolved with methanol and determined by HPLC using PHENOMENEX C18 (4.6 mm x 250 mm, 5 microns) chromatographic column, methanol-acetonitrile-water (15:15:10) as mobile phase. The wavelength for detection was 254 nm.

RESULTThe peak of schizandrin appears on about 7.10 minutes. The standard curves of schizandrin were linear in the concentration range of 0.2-2.0 micrograms, r = 0.9996. The average recovery of schizandrin were 100.5% (RSD 2.84%).

CONCLUSIONThis method was found to be sensitive, quick and accurate for the measurement of schizandrin concentrations in Shengmaiyin.

Administration, Oral ; Chromatography, High Pressure Liquid ; Cyclooctanes ; analysis ; Drug Combinations ; Drugs, Chinese Herbal ; administration & dosage ; chemistry ; isolation & purification ; Lignans ; analysis ; Plants, Medicinal ; chemistry ; Polycyclic Compounds ; analysis ; Schisandra ; chemistry

The aim of the study is to establish a new method of quality evaluation and validate its feasibilities by the simultaneous quantitative assay of four lignanoids in Schisandra chinensis. A new quality evaluation method, quantitative analysis of multi-components by single marker (QAMS), was established and validated with Schisandra chinensis. Four main lignanoids, schisandrin, schisantherin A, deoxyschizandrin and gamma-schizandrin, were selected as analytes and schisandrin as internal reference substance to evaluate the quality. Their contents in 13 different batches of samples, collected from different bathes, were determined by both external standard method and QAMS. The method was evaluated by comparison of the quantitative results between external standard method and QAMS. No significant differences were found in the quantitative results of four lignanoids in 13 batches of S. chinensis determined by external standard method and QAMS. QAMS is feasible for determination of four lignanoids simultaneously when some authentic standard substances were unavailable, and the developed method can be used for quality control of S. chinensis.
Chromatography, High Pressure Liquid ; methods ; Cyclooctanes ; analysis ; Dioxoles ; analysis ; Drugs, Chinese Herbal ; chemistry ; Fruit ; chemistry ; Lignans ; analysis ; Plants, Medicinal ; chemistry ; Polycyclic Compounds ; analysis ; Quality Control ; Schisandra ; chemistry

AIMTo investigate the inhibition of amyloid beta-protein 42 (Abeta42) production in M146L cells by gamma-schisandrin.

METHODSM146L cells which can produce considerable Abeta42 in vitro were treated with gamma-schisandrin (1.67, 5.00 and 15.00 microg x mL(-1)), beta-secretase inhibitor (S4562, 100.00 microg x mL(-1)) and gamma-secretase inhibitor (S2188, 13.68 microg x mL(-1)), separately. Cell counting kit-8 (CCK-8) was used to assess cell viability. Enzyme-linked immunosorbent assay (ELISA) was carried out to determine the amount of Abeta42. Western blotting was used to examine C99, an intermediary product of APP cleaved by beta-secretase. beta-Secretase and gamma-secretase activities were assayed by commercial kits.

RESULTSThe CCK-8 assay indicated that different concentrations of gamma-schisandrin had no neurotoxicity on the cultured M146L. And the ELISA test showed that the amount of Abeta42 secreted by M146L cells treated with gamma-schisandrin (5.00 and 15.00 microg x mL(-1)) decreased obviously as compared with solvent control. The results of Western blotting test indicated that there was no change of C99 contents and beta-secretase activity in gamma-schisandrin treated cells, while gamma-secretase activity decreased obviously.

CONCLUSIONgamma-Schisandrin inhibited production of Abeta42 in M146L cells through inhibiting gamma-secretase.

Alzheimer Disease ; drug therapy ; Amyloid Precursor Protein Secretases ; antagonists & inhibitors ; metabolism ; Amyloid beta-Peptides ; antagonists & inhibitors ; biosynthesis ; Animals ; CHO Cells ; Cricetinae ; Cricetulus ; Cyclooctanes ; Dose-Response Relationship, Drug ; Humans ; Lignans ; Peptide Fragments ; antagonists & inhibitors ; biosynthesis ; Polycyclic Compounds ; pharmacology