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This study was carried out to investigate the chemical constituents from Xanthii Fructus(the fruits of Xanthium sibiricum). The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 and ODS chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR and other spectral data, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW264.7 as a screening model. A total of twenty-one compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as uracil(1), thymine(2), uridine(3), indole-3-carbaldehyde(4), indole-3-carboxylic acid(5), 2'-O-methyluridine(6), guanosine(7), 2,4(1H,3H)-quinazolinedione(8), 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9), nicotinamide(10), N-acetyl-L-phenylalaninol(11), heliolactam(12), terresoxazine(13), caudatin(14), qingyangshengenin(15), caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(16), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(17), caudatin-3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(18), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(19), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside(20), rostratamine-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(21). Compounds 5-21 are obtained from genus Xanthium for the first time. Compounds 12 and 13 indirectly exhibited anti-inflammatory activity by suppressing LPS-induced NO production in RAW264.7 cells with IC_(50) values of(15.45±0.56) and(20.14±0.78) μmol·L~(-1), respectively.
Subject(s)
Chromatography, High Pressure Liquid , Fruit , Glycosides , Magnetic Resonance Spectroscopy , Molecular Structure , XanthiumABSTRACT
Objective To evaluate the applicability of small molecular markers of nephrotoxicity that in prediction of drug toxicity.Method Extracts of five kinds of traditional Chinese medicines (Tripterygium wilfordii,Strychni semen,Aristolochiafangchi,Rhei Radix et Rhizoma,and Xanthium sibiricum) that had known as nephrotoxicity were ig given to rats to establish renal injury models,and the blood samples were collected after administration for 1 and 7 d.Then blood samples were analyzed by UPLC/Q-TOF-MS for five kinds of small molecule biomarkers-thymidine,lyso-phosphatidylcholine (LPC 16:1),LPC (18:4),LPC (20:5),and LPC (22:5).The support vector machine (SVM) prediction model was established to determine the toxicity.The levels of Cr and BUN in serum were determined by automatic biochemical analyzer.The rats in each group were sacrificed after blood collection,and the kidneys were taken for HE staining.Result No toxicity was observed in the control group,and the biochemical test results showed no renal injury after mentioned five kinds Chinese herbs were given for 1 d,while SVM model of nephrotoxicity had been found abnormal.After administration for 7 d,the results of SVM model show renal toxicity,which were consistent with biochemical and pathological examination.Conclusion Metabonomics combined with the earlier established SVM model enabled prediction of drug nephrotoxicity more sensitively,quickly and \ccurately,and it is of great significance for the discovery of drug toxicity as well as the prevention and treatment of drug-induced renal injuries in clinic.
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Objective: To study the chemical constituents from the fruits of Xanthium sibiricum. Methods: The constituents were isolated and purified by silica gel column chromatography, ODS reverse phase column chromatography, Sephadex LH-20, MCI gel CHP 20P, and HPLC methods. The structures were identified by HR-ESI-MS and spectral analysis methods. Results: Fourteen compounds were isolated from the fruits of X. sibiricum and the structures were identified as xanthiazone (1), 2-hydroxy-xanthiside (2), uridine (3), indole-3-carbaldehyde (4), naphthisoxazol A (5), aminobenzene propanamide (6), N-benzoyl-2-aminoethyl β-D- glucopyranoside (7), ω-hydroxypropioguaiacone (8), arbutin (9), icariside D1 (10), lcariside F2 (11), (+)-erythro- guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (12), (-)-threo-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (13), and coniferine (14). Conclusion: Compounds 3-14 are obtained from the fruits of X. sibiricum for the first time.
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Objective:To analyze the changes of chemical compositions and relative contents of volatile constituents in raw Xanthi-um sibiricum Patr. and fried Xanthium sibiricum Patr. Methods: Headspace solid phase micro extraction ( HS-SPME) combined with gas chromatography-mass spectrometry ( GC-MS) was used to study the volatile components in raw and fried products of Xanthium sibir-icum Patr. . A peak area normalization method was applied to calculate the relative percentage content of each composition. Results:Totally 26 and 27 kinds of compounds were isolated and identified respectively from raw and fried xanthium including 19 species and re-spectively accounting for 68. 69% and 90. 08% of the total volatile components. In the raw products, the components with high con-tents were camphor (15. 3%), eucalyptus oil alcohol (9. 6%) and borneol (6. 89%), while in the fried products, those were men-thol (24. 09%), borneol (18. 48%) and eucalyptol (7. 19%). Conclusion:The relative contents of components with effects on rhi-nitis in the fried products are obviously higher than those in the raw products. HS-SPME-GC-MS can be used to detect the volatile com-positions and their relative contents in the raw products and fried products of Xanthium sibiricum Patr. . From the changes of volatile components, theoretical basis can be laid for the components with certain efficacy in raw and fried Xanthium sibiricum Patr. , and scien-tific basis can be provided for their further study and comprehensive utilization.
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By retrieving domestic and foreign literatures, the authors provided a systematic review for effects of Xanthii Fructus, toxicity recorded in ancient/current literatures and relevant toxicological experience, and summarized clinical characteristics of clinical cases related to Xanthii Fructus and influencing factors. In addition to liver and kidney injuries as the major side effects of Xanthii Fructus, neurotoxicity and cardio-toxicity of Xanthii Fructus were also common clinical adverse events. However, there have been a few animal experimental studies so far. Oral administration and external application with Xanthii Fructus have often caused skin reactions, even such severe cases as exfoliative dermatitis. The authors suggested standardizing the clinical medication, avoiding to use untreated prescriptions and unprocessed herbs, ensuring the effective and safety use of Xanthii Fructus in strict accordance with the recommended dosage and usage in pharmacopeia, paying attention to the accumulation of safety signals, strengthening studies on toxic substance, toxicity mechanism, and synergy and attenuation effects.
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Objective: To study the chemical constituents of Xanthii Fructus. Methods: The compounds were isolated and purified by chromatography on silica gel, ODS, and Sephadex LH-20 columns, and their structures were determined according to physicochemical properties and spectral analyses. Results: Fifteen compounds were obtained and identified as loliolide (1), (3S, 5R, 6S, 7E)-5, 6-epoxy-3-hydroxy-7-megastigmene-9-one (2), 7α-hydroxy-β-sitosterol (stigmast-5-ene-3β, 7α-diol) (3), stigmast-4-ene-3β, 6α-diol (4), 6'-palmitoxyl-β-daucosterin (5), β-sitosterol (6), daucosterol (7), balanophonin (8), pinoresinol (9), xanthatin (10), xanthinosin (11), xanthienopyran (12), p-hydroxybenzaldehyde (13), 3-methoxy-4-hydroxy-transcinnamaldehyde (14), and quercetin (15). Conclusion: Compounds 1-5 are obtained from the plants in Xanthium L. for the first time, and compound 8 is isolated from this plant for the first time.
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Objective To isolate and purify the antioxidant compounds from fructus xanthii and to study their antioxidant activity.Methods Compounds were isolated by repeated silica gel,macroreticular resin Diaion HP-20 and Sephadex LH-20 column chromatography and their antioxidant property was determined by scavenging activity to DPPH and ?OH.Results Five antioxidant compounds were isolated from the ethyl acetate extracts of Xanthium sibiricum fruits and their structures were identified as 5,7,3',4'-tetramethoxyisoflavone,myricetin-3'-methyl ether,falcalindiol,1,8-heptadecadiene-4,6-diyne-3,10-diol and 3,4-dihydroxybenzoic acid.Among them,3,4-dihydroxybenzoic acid had the highest radical scavenging activity.Conclusion All above 5 compounds have high antioxidant activities,and antioxidant activity of 3,4-dihydroxybenzoic acid is the highest.