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Objective: To research the chemical constituents from Trigonella foenum-graecum. Methods: The chemical constituents were separated and purified by sephadex LH-20, silica gel, semi-prepared HPLC and other chromatography techniques. Their structures were elucidated by their physicochemical properties and NMR data. Results: Six steroidal saponins and flavonoids (1-6) were isolated from the ethanol extracts of T. foenum-graecum and identified as 22-methoxy-trigoneoside IIb (1), gitogenin (2), diosgenin (3), luteolin (4), cynaroside (5), and luteolin-7-O-rutinoside (6). Conclusion: Compound 1 is a new compound, and compounds 5 and 6 are obtained for the first time from T. foenum-graecum.
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OBJECTIVE: To study the fingerprints of rhizomes of Paris polyphylla Smith var. polyphylla and Paris polyphylla Smith var. yunnanensis (Franch.) Hand. -Mazz from different origins in Dali and the differences of seven main steroidal saponins. METHODS: The fingerprints of rhizomes of Paris polyphylla var. polyphylla and Paris polyphylla var. yunnanensis from different origins in Dali were established by HPLC. The similarity of fingerprints and seven main steroidal saponins were compared and analyzed. RESULTS: There were 14 common peaks in the fingerprints of rhizomes of Paris polyphylla var. polyphylla from different origins in Dali, and the similarity of the fingerprints of the samples from different habitats except Jinhua Weishan and Longjie Weishan was greater than 0.9. There were 13 common peaks in the fingerprints of rhizomes of Paris polyphylla var. yunnanensis from different origins in Dali, and the similarity of the samples from different origins was greater than 0.92. There were 11 common peaks in the fingerprints of rhizomes of Paris polyphylla var. polyphylla and Paris polyphylla var. yunnanensis from different origins in Dali, and the similarity of the fingerprints was very low, between 0.057 and 0.225. Polyphyllin Ⅰ, polyphyllin Ⅱ, polyphyllin Ⅵ and polyphyllin Ⅶ are detected in the rhizomes of Paris polyphylla var. polyphylla and Paris polyphylla var. yunnanensis from different origins in Dali. The average peak areas of polyphyllin Ⅰ, polyphyllin Ⅱ, polyphyllin Ⅵ and polyphyllin Ⅶ in Paris polyphylla var. yunnanensis from different origins in Dali were higher than those of Paris polyphylla var. polyphylla. Polyphyllin H was detected in the rhizomes of Paris polyphylla var. yunnanensis from Leqiu Nanjian, Jinhua Weishan, Fengyu Eryuan, Dengchuan Eryuan, Hongyan Midu, Xiyi Heqing and the rhizomes of Paris polyphylla var. polyphylla from Wanqiao Dali, Fengyi Dali, Xiyi Heqing, Hongyan Midu and Leqiu Nanjian. Polyphyllin Ⅲ was detected in the rhizomes of Paris polyphylla var. polyphylla from the origins except Longjie Weishan. Polyphyllin Ⅴ was also detected in the rhizomes of Paris polyphylla var. polyphylla in Fengyu Eryuan and Xiyi Heqing. CONCLUSION: Polyphyllin Ⅰ, polyphyllin Ⅱ, polyphyllin Ⅵ and polyphyllin Ⅶ are detected in the rhizomes of Paris polyphylla var. polyphylla and Paris polyphylla var. yunnanensis from different origins in Dali. The similarity of the HPLC fingerprints of the rhizomes of Paris polyphylla var. polyphylla and Paris polyphylla var. yunnanensis is very low, and there are great differences in seven main steroidal saponins. The contents of polyphyllin Ⅰ, polyphyllin Ⅱ, polyphyllin Ⅵ and polyphyllin Ⅴ in Paris polyphylla var. yunnanensis are higher than those in Paris var. polyphylla.
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Two new steroidal saponins, named timosaponin P (1) and timosaponin Q (2), were isolated from the rhizome parts of Anemarrhena asphodeloides Bunge using various chromatographic methods. Their structures and absolute configurations were elucidated by a combination of spectroscopic and spectrometric data, including 1D, 2D NMR, HR-ESI-MS and ECD calculations, and this is the first time the absolute configuration of C-23 of steroidal saponin was confirmed by ECD calculations.
Subject(s)
Anemarrhena , Chemistry , Drugs, Chinese Herbal , Chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Saponins , Chemistry , Steroids , ChemistryABSTRACT
Objective: To observe the effects of steroidal saponin YB16 of Ypsilandra thibetica on cell apoptosis of A549 human lung cancer cells, and explore the mechanism of apoptosis. Methods: Cells were cultured in vitro and treated with different concentration of YB16; The proliferation of A549 cells was examined by MTT method; Cells fluorescence changes of A549 were examined by acridine orange (AO) and JC-1 staining; PI, Annexin V-FITC/PI double staining, and JC-1 staining were examined by flow cytometry. Intracellular level of reactive oxygen (ROS) was determined by DCFH-DA assay, the expression of YB16 on apoptosis-related proteins was examined by Western blotting. Results: Steroidal saponin YB16 of Y. thibetica could inhibit A549 cells growth significantly with dose-effect relationship (P < 0.05); With the increasing of drug concentration, cell morphology changed significantly compared with the control group; Cell apoptosis rate increased with the different concentration of YB16 (P < 0.05); Mitochondrial membrane potential decreased significantly; ROS level of cells was increased with a significant difference (P < 0.05). Apoptotic protein, such as Bcl-2 expression of anti-apoptotic protein, was decreased, and the expression of pro-apoptotic protein Bax and cleaved caspase-3 was increased treated by YB16 after 24 h (P < 0.05). Conclusion: Steroidal saponin YB16 of Y. thibetica could inhibit the cell proliferation, reduce the mitochondrial membrane potential, enhance ROS level of A549 cells, and promote apoptosis. Therefore, it has a good anti-tumor activity.
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Objective: To study the chemical constituents of Solanum torvum. Methods: Column chromatography was used to isolate and purify the constituents, whose structures were identified on the basis of spectral data analyses. Results Eleven compounds were isolated and identified as N-trans-feruloyl tyramine (1), N-trans-P-coumaroyl tyramine (2), 3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2- methoxyethyl]-acrylamide (3), N-trans-P-coumaroyl octopamine (4), kaempferol (5), quercetin (6), trans-caffeic acid (7), solagenin 6-O-(β-D- quinovopyranoside) (8), (25S)-6α-hydroxy-5α-spirostan-3-one-6-O- [α-Z,-rhamnopyranosyl-(1→3)- β-D-quinovopyraposide] (9), torvosides M (10), and 6α-O-[β-D-xylopyranosyl-(1→3)-beta;-D- quinovopyranosyl]-(25S)-5α-spirostan- 3β-ol (11). Conclusion: Compound 3 is firstly reported as a new natural product. Compounds 1-7 are isolated from S. torvum for the first time.
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@# bjective To investigate the effect of Steroidal Saponin TSA on the recovery of sensorimotor function after cerebral ischemia in rats. Methods Cerebral ischemia was induced by middle cerebral artery occlusion in rats which were divided into 6 groups: vehicle, TSA 15 mg/kg, 30 mg/kg, 60 mg/kg，Angong Niuhuang (ANGH) 400 mg/kg and sham. Animals received drug administration 3～14 d after ischemia. Sensorimotor function was evaluated with beam-walking and adhesivetape-exposing performance 3 d, 7 d, 10 d, and 14 d after ischemia. Neural cell injury in the sensorimotor cortex ipsilateral to ischemia was studied with hematoxylin-eosin stain. Immunohistochemistry Methods were used to measure the vascular endothelial growth factor (VEGF) protein and the angiogenesis of the area around infarction tissue. Results Animals receiving TSA at a dosage of 30 mg/kg and 60 mg/kg recovered better in beam-walking and adhesivetape-exposing performance than vehicles, and the improvement became significant 14 d after ischemia. Treatment with TSA 30 mg/kg、60 mg/kg also significantly reduced the neural cell loss in sensorimotor cortex and increased the expression of VEGF protein and the microvascular density. Conclusion TSA can improve the recovery of sensorimotor function follwing focal cerebral ischemia in rats, which may involve the neural cells protection, promoting the expression of VEGF and angiogenesis after ischemia.
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Objective To develop a HPLC method for determining the content of riparsaponin in Homonoia riparia Lour.Methods The determination was performed on the HYPERSILBDS-C18(200 mm?4.6 mm,5 ?m) with mobile phase consisted of acetonitrile-water(75∶25) at a flow rate of 1.0 ml/min.The detection wavelength was set at 203 nm,the column temperature was 30 ℃,and the column pressure was 10.0 MPa.Results There was a good linear relationship for riparsaponin over the ranges of 5 to 500 ?g/ml(r=0.999 8).The average recovery was 99.44%,and RSD was 0.52%(n=15).Conclusion The method has good reproducibility and high precision.It can be applied in quality control of Homonoia riparia Lour.
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Objective To study the chemical constituents of Dioscorea zingiberensis.Methods The fresh rhizome of D.zingiberensis was extracted three times,3 h once with EtOH-H2O at 80 ℃.The EtOH was evaporated under reduced pressure to give a residue which was suspended in water and then was exacted with petroleum ether,ethyl acetate,and n-butanol fraction.The water fraction was isolated by the reversed-phase ODS column chromatography.The chemical structures were elucidated by means of 1H-NMR,13C-NMR,135DEPT,HMQC,and HMBC spectroscopic analyses.Results Three steroidal saponins were isolated from the fresh rhizome of D.zingiberensis.The compounds were identified as:diosgenin-3-O-?-D-glucopyranosyl(1→3)-?-D-glucopyranosyl(1→4)-[?-L-rhamnopyranosyl(1→2)]-?-D-glucopyranoside(Ⅰ),(25R)-26-O-?-D-glucopyranosyl-furost-5-en-3?,22?-diol-3-O-?-D-glucopyranosyl(1→3)-?-D-glucopyranosyl(1→4)-[?-L-rhamnopyranosyl(1→2)]-?-D-glucopyranoside(Ⅱ),and(25R)-26-O-?-D-glucopyranosyl-furost-5-en-3?,22?-diol-7-carbonyl-3-O-?-D-glucopyranosyl(1→3)-?-D-glucopyranosyl(1→4)-[?-L-rhamnopyranosyl(1→2)]-?-D-glucopyranoside(Ⅲ).Conclusion Compound Ⅲ is a novel compound named as zingiberenin H.
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Objective To study water-soluble constituents of Dioscorea zingiberensis in order to seek active components. Methods Various chromatographic techniques were used to isolate the constituents. Structures of compounds were elucidated by spectroscopic analyses of 1H-NMR, 13C-NMR, 135DEPT, HMQC, HMBC, and TOCSY. Results One new steroidal saponin was isolated and identified as 26-O-(?-D-glucopyranosyl)-(25R)-furost-5-en-3?, 26-diol-22-OMe-3-O-｛?-L-rhamnopyranosyl-(1→4)-[?-D-glucopyranosl-(1→3)-?-D-glucopyranosl-(1→2)]-?-D-glucopyranoside｝. Conclusion The compound is a novel compound named as zingierenin E. The other two compounds are reported for the first time from D. zingiberensis.