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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
Xanthii Fructus (XF), the dry ripe involucrate fruit of Xanthium sibiricum, with the function of dispersing wind, dehumidification and dredging stuffy nose, plays an important role in the treatment of nasal diseases and has great development potential and market value. There were a large number of patents on XF in China with a wide range, which was in the leading position in the field of medicine. However, the patent development and basic research in the industrial chain and midstream reaches were relatively weak, the research was not deep enough, and the patent conversion rate was low. For the downstream products of XF, we should improve the quality of development and create the key products; The basic research in the upstream and midstream of the industrial chain should be combined with the application research, strengthen the technological breakthrough, enhance the awareness of patent protection and improve the patent quality in China. Based on the Incopat global patent database, the patent analysis method and SWOT analysis method were combined to analyze the current situation and development trend of patent application in XF industrial chain at home and abroad, to provide reference for the development and utilization of XF in the new era, the layout of industrial chain patents, and the improvement of international competitiveness of related industries.
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Objective:To investigate the pharmaceutical idiosyncratic hepatotoxicity effect of Xanthii Fructus on the immune-sensitive rat model induced by endotoxin lipopolysaccharide （LPS）. Method:The SD rats were randomly divided into five groups： control group， model group， and three Xanthii Fructucs groups. The immune-sensitive rat model was established by LPS （iv. 0.7 mg·kg-1， twice every 7 days）. Then， the rats in control and model groups received the equal volume of distilled water， while the rats in Xanthii Fructus groups were administrated with water extract of Xanthii Fructus intragastrically （1.67， 5.01， 16.7 g·kg-1， respectively） for 14 days. The serum and liver of the rats were collected on the 7th and 14th day to examine the levels of hepatotoxic biomarkers， including alanine aminotransferase （ALT）， aspartate aminotransferase （AST）， total bilirubin （TBil）， alkaline phosphatase （ALP）， and total bile acids （TBA）， and liver histopathology. In addition， inflammatory factors， including interleukin-1β（IL-1β）， interleukin-2（IL-2）， interleukin-6（IL-6）， interleukin-10（IL-10）and tumor necrosis factor-α（TNF-α）of the idiosyncratic hepatotoxicity rats， were determined by enzyme-linked immunosorbent assay（ELISA）. Result:The immune-sensitive model rats showed elevated levels of IL-1β， IL-6（P<0.05，P<0.01）， and mild inflammatory cells infiltrated in portal area of liver significantly （P<0.05）， with no significant changes in hepatotoxic biomarkers. Meanwhile， there was no significant change between Xanthii Fructus groups and model rats in the levels of hepatotoxic biomarkers， inflammatory factors and hepatic lesions. Conclusion:Water extract of Xanthii Fructus intragastrically does not affect the levels of hepatotoxic biomarkers， inflammatory factors and hepatic lesions in rats induced by LPS intravenously. That is to say， Xanthii Fructus does not induce pharmaceutical idiosyncratic hepatotoxicity.
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Objective:To discuss the effect of volatile oil from Xanthii Fructus on airway remodeling of rats with bronchial asthma, in order to discuss the mechanism of action through matrix metalloteinases-9 (MMP-9), tissue inhibitor of metalloproteinase-1 (TIMP-1), platelet derived growth factor (PDGF), transforming growth factor-β1 (TGF-β1), Smad2, Smad3 and Smad7 mRNA expressions. Method:Forty-eight rats (half males and half females) were randomly divided into six groups (n=8), namely normal saline group, model group, volatile oil from Xanthii Fructus (7.5, 15, 30 mg·kg-1) groups and dexamethasone group (0.5 mg·kg-1). Except for normal saline group, airway remodeling of rats were established through ovalbumin sensitization and atomization inhalation method. At volatile oil group, rats got volatile oil spray since the first time (the 4th week after modeling) of inspiration of asthma to the last day before the end of test. Histopathological changes of bronchus and lung were analyzed by htoxylin eosin (HE) stain. And airway remodeling was observed, and perimeter of bronchial lumen (Pi), smooth muscle area of bronchi (S), tube wall area (W) and nuclei of smooth muscle cells (N) were recorded. And levels of endothelin-1 (ET-1) and insulin-like growth factor-1(IGF-1) in irrigation solution of Alveoli (BALF) were detected. And mRNA expressions of MMP-9, TIMP-1, PDGF, TGF-β1, Smad2, Smad3 and Smad7 were detected by real-time quantitative-polymerase chain reaction (Real-time PCR). Result:In the model group, infiltration of a large number of inflammatory cells were found at the peribronchial wall, airway smooth muscle thickness and basement membrane increased, and bureaucratic cavity was narrower and flatter. Volatile oil from Xanthii Fructus can ameliorate pathological damage of bronchopulmonary tissue. Levels of S/Pi, W/Pi and N/Pi, BALF, ET-1, IGF-1 and MMP-9/TIMP-1 and mRNA expressions of MMP-9 and PDGF in volatile oil group and dexamethasone group were lower than those in model group (Pβ1, Smad2 and Smad3 were less than those in model group (PPConclusion:Volatile oil from Xanthii Fructus can regulate levels of MMP-9, TIMP-1, MMP-9/TIMP-1, TGF-β1/Smad, inhibit expressions of PDGF, ET-1 and IGF-1, and suppress subepithelial fibrosis, extracellular matrix synthesis, proliferation and migration of airway smooth muscle cells to relieve or inhibit airway remodeling, so as to prevent and treat asthma.
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Xanthii Fructus is a traditional Chinese medicine for the treatment of sinusitis and headache,rich in medicinal materials and is widely used for more than 1 800 years. Modern pharmacological studies have showed that Xanthii Fructus has anti-inflammatory,analgesic,anti-tumor,anti-bacterial,hypoglycemic,anti-allergic,immunomodulatory and other pharmacological effects,which can be commonly used in the treatment of diseases relating to immune abnormalities,such as rheumatoid arthritis,acute and chronic rhinitis,allergic rhinitis,and skin diseases,with a high medicinal value. Toxicological studies have shown that Xanthii Fructus poisoning can cause substantial damage to organs,such as the liver,kidney,and gastrointestinal tract,especially to liver. Because of the coexisting of its efficacy and toxicity,Xanthii Fructus often leads to a series of safety problems in the clinical application process. This study attempts to summarize its characteristics of adverse reactions,analyze the root cause of the toxicity of Xanthii Fructus from such aspects as processing,dose,course of treatment and eating by mistake,discuss the substance of its efficacy/toxicity from chemical compositions,and put forward exploratory thinking about how to promote its clinical rational application from the aspects such as strict processing,reasonable compatibility,medication information,contraindication,strict control of the dose,and course of treatment,so as to promote the safe and reasonable application of Xanthii Fructus.
Subject(s)
Humans , Drugs, Chinese Herbal/therapeutic use , Fruit/toxicity , Medicine, Chinese Traditional , Xanthium/toxicityABSTRACT
Xanthii Fructus (XF) is one of important drugs for the treatment of sinusitis and headache.It is commonly used in the treatment of diseases relating to immune abnormalities,such as rheumatoid arthritis,acute and chronic rhinitis,allergic rhinitis,and skin diseases,with a high medicinal value.Modern pharmacological studies have showed a wide range of pharmacological effect and a high medicinal value in XF.However,due to long-term or excessive intake,and improper processing of medicinal materials,toxic reactions have often occurred.Toxicological studies have shown that XF poisoning can cause substantial damage to organs,such as the liver,heart and kidney,especially to liver.This paper reviews the pharmacological action,toxic substances and hepatotoxicity mechanism of XF by systematically reviewing and summarizing relevant literatures on XF both at home and abroad.It is concluded that XF has anti-hypertension,anti-allergic,anti-bacterial,anti-inflammatory,analgesic,anti-tumor and lipid-decreasing effects.The toxic components are mainly atractyloside,carboxy atractyloside and 4'-desulphate-atractyloside.The mechanism of hepatotoxicity induced by XF is closely related to lipid peroxidation,bile cholestasis and hepatocyte energy metabolism.Meanwhile,the discovery of novel biomarkers of hepatotoxicity,such as miRNA-122,also provides new ideals for medical research.Toxic traditional Chinese medicine (TCM) is an important part of TCM.Compatibility or processing can reduce or eliminate toxicity and preserve or increase efficacy.At present,there are few reports on the principle of attenuating the production of XF.The author suggests further strengthening the study on the principle of attenuation of XF,giving full play to the unique curative effect of XF and developing its greater medicinal value.
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Xanthii Fructus has been traditionally used for the treatment of rhinitis, rheumatoid arthritis, and eczema. In this study, a high-performance liquid chromatography-photodiode array (HPLC-PDA) method was developed and then used for the simultaneous analysis of eight phenylpropanoids in Xanthii Fructus. The analytical column used for this separation was a SunFire™ C₁₈ column, maintained at 40℃. The mobile phase used was 1.0% acetic acid in distilled water and 1.0% acetic acid in acetonitrile with gradient elution. For identify of each component, the mass spectrometer (MS) was used a Waters triple quadrupole mass spectrometer requipped with electrospray ionization (ESI) source. The HPLC-PDA method showed good linearity: correlation coefficients were ≥ 0.9996. The limits of detection and quantification of the eight compounds were 0.02 – 0.04 and 0.06 – 0.14 µg/mL, respectively. The extraction recoveries ranged from 97.51 to 108.67%. The relative standard deviation values of intra- and inter-day precision were 0.06 – 1.55 and 0.09 – 1.68%, respectively. The validated HPLC-PDA method was applied to simultaneously analyse the amounts of eight phenlypropanoids in Xanthii Fructus.
Subject(s)
Acetic Acid , Arthritis, Rheumatoid , Eczema , Limit of Detection , Methods , Rhinitis , WaterABSTRACT
This project is to investigate lignans from the dried fruits of Xanthium sibiricum (Xanthii Fructus). The chemical constituents were extract by 70% ethanol and isolated by silica gel, ODS, Sephadex LH-20, MCI column chromatography. Based on comparison of their spectral data with those reported in literature, they were elucidated as (-)-pinoresinol (1), balanophonin A (2), diospyrosin (3), dehydrodiconiferyl alcohol (4), 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol (5), (-)-simulanol (6), (-)-7R,8S-dehydrodiconiferyl alcohol (7), chushizisin E (8), dihydrodehydrodiconiferyl alcohol (9), 7R,8S-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (10), erythro-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (11), leptolepisol D (12), 8-O-4' neolignan 4-O-β-glucopyranoside (13), (-)-1-O-β-D-glucopyranosyl-2-{2-methoxy-4-[1-(E)-propen-3-ol]phenoxyl}-propane-3-ol(14), 1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1,2,3-trihydroxypropyl)-2-methoxy]-phenoxy-1,3-propandiol (15), threo-dihydroxy dehydrodiconiferyl alcohol (16), (-)-(2R)-1-O-β-D-glucopyranosyl-2-{2-methoxy-4-[(E)-formylviny1]phenoxyl} propane-3-ol (17). Compound 2-17 were isolated from the genus Xanthium for the first time. Compound 1 were isolated form Xanthii Fructus for the first time.
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Objective:To establish the HPLC specific chromatogram and provide comprehensive evaluation of Xanthii fructus from different regions.Methods:The HPLC analysis was performed on an Alltima C18 column (250 mm ×4.6 mm,5μm) with acetonitrile-0.1％phosphoric acid solution as the mobile phase with gradient elution at a flow rate of 0.8 ml· min-1 .The detection wavelength was 278 nm.The column temperature was 25℃.The software"Similarity Evaluation System for Chromatographic Fingerprint of TCMs"was employed to carry out the similarity analysis of the samples from Henan , Jilin, Anhui and the other regions .Results:The specific chromatogram was preliminarily constructed and 5 common peaks with chlorogenic acid as the reference were identified .Conclusion:The method is scientific basis of the quality assessment of Xanthii fructus with convenient and reliable properties .
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Objective:To examine the content changes of neochlorogenic acid, chlorogenic acid, 1, 5- dicaffeoylquinic acid and total phenolic acids in the water extract from raw and fried Xanthii Fructus. Methods:The stir-frying method was used to process fried Xanthii Fructus from different habitats. The contents of neochlorogenic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid in the wa-ter extract were determined by HPLC, the total phenolic acids content was determined by UV. Results:The contents of neochlorogenic acid, chlorogenic acid, 1,5-dicaffeoylquinic acid and total phenolic acids in the water extract from fried Xanthii Fructus were all in-creased. Conclusion:Fried Xanthii Fructus can increase the contents of effective ingredients in the decoction resulting in the enhanc-ment of clinical curative effect.
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Objective: To analyze the difference of chemical compositions in Xanthii Herba and Xanthii Fructus. Methods: Eight batches of Xanthii Herba and Xanthii Fructus samples from different origins were determined by UPLC-Triple TOF-MS/MS. Through the analysis of the multistage tandem mass spectrometry, the characteristic peaks were extracted with mass spectrometry data peak matching, peak alignment, and noise filtering. Principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA) were used for data processing. The components were identified according to a mass spectrometry accurate mass and two mass spectrometry fragmentation information, combined with the software of database search and literature. Results: The chemical compositions in Xanthii Herba and Xanthii Fructus samples are clearly distinguished. Forty-four compositions have the differences between Xanthii Herba and Xanthii Fructus. Forty-one chemical compositions are identified. Among of them, there are 12 kinds of differential compositions which presented different changing laws. Conclusion: From the different compositions of Xanthii Herba and Xanthii Fructus, the material basis can be provided for revealing the property and efficacy in Xanthii Herba and Xanthii Fructus.
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OBJECTIVE: To establish a high performance capillary electrophoresis (HPCE) method for simultaneousn determination of nchlorogenic acid, caffeic acid, ferulic acid, isochlorogenic acid A, isochlorogenic acid C, neochlorogenic acid, and cynarin in the herbs of Xanthii Herba and Xanthii Fructus. METHODS: 50 mmol·L-1 borax-water was used as buffer solution (pH 9.54). The separation was performed on an uncoated fused silica capillary (64.5 cm×75 μm, 56 cm of effective length) maintained at 25℃ at voltage of 25 kV. The detection wavelength was 326 nm, and the sample was injected at 25 kPa×6 s. RESULTS: The calibration curves of the seven phenolic acid showed good linearity (r>0.9994) in the ranges of the tested concentrations, and the average recoveries of the method were between 99.85%-102.70%. CONCLUSION: The method is simple, accurate and reproducible, and can be used for the quality evaluation and control of Xanthii Herba and Xanthii Fructus.
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Objective: To identify Xanthii Fructus and secure its quality and safety in medication. Methods: Total ge-nomic DNA was extracted from Xanthii Fructus and its adulterants. ITS2 sequences were amplified, and purified PCR products were sequenced. Sequence assembly and consensus sequence generation were performed using the CodonCode Aligner V 4.2. The Kimura 2-Parameter (K2P) distances were calculated using MEGA 5.0. The neigh-bor-joining (NJ) phylogenetic trees were constructed. Results: The intraspecific genetic distances of Xanthii Fructus were 0. The interspecific genetic distances between Xanthii Fructus and its adulterants were ranged from 0.009 to 0.542. The NJ tree showed that Xanthii Fructus could differ from its adulterants obviously. Conclusion: ITS2 can be used to identify Xanthii Fructus from its adulterants effectively, and our study further confirmed the effectiveness of ITS2 to identify traditional Chinese medicinal materials.
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Objective To study the best processing technology of Xanthii Fructus by determining the contents of chlorogenic acid and 3,5-dicaffeoylquinic acid in which processed by different temperature and time. Methods Sixteen batchs samples of Xanthii Fructus were propressed by stir-frying with sand, and the propressed temperature and time were set at 150-220 ℃ and 0.5-7 minutes. Two phenolic acid components in Xanthii Fructus were simultaneously determined. The column was UPLC Acquity BEH C18 (2.1 mm×100 mm, 1.7 μm). The mobile phase was acetonitrile-0.1% phosphoric acid, gradient elution. The flow rate was 0.25 mL/min, and the detection wavelength was 327 nm. Results The sample with highest contents of chlorogenic acid and 3,5-dicaffeoylquinic acid was the batch processed by stir-frying with sand at 160 ℃ for 7 minute, which was 2.498, 2.004 mg/g, respectively. Conclusion According to the appearance of processed sample and the content of chlorogenic acid and 3,5-dicaffeoylquinic acid, the optimal processing technology of Xanthii Fructus was stir-frying with sand at 160 ℃ for 7 min.
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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 develop an UPLC method for determination of nine phenolic acid components in Xanthii Fructus from different habitats. METHODS: The analysis was carried out on BEH C18(2.1 mm×100 mm, 1.7 μm) column. The mobile phase was composed of acetonitrile and 0.1% phosphoric acid water in gradient elution mode.The flow rate was 0.25 mL·min-1 and the detect wavelengths were set at 220 and 327 nm for different components. RESULTS: The nine phenolic acid components showed good linearity(r>0.999) in the ranges of the tested concentrations, and the average recoveries of the method were between 96.99%-99.55%. CONCLUSION: This method is simple, rapid, reproducible and can be used to control the quality of Xanthii Fructus.