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.
Chromatography, High Pressure Liquid ; Fruit ; Glycosides ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Xanthium

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.
Drugs, Chinese Herbal/therapeutic use* ; Fruit/toxicity* ; Humans ; Medicine, Chinese Traditional ; Xanthium/toxicity*

Through the methods of polyamide resin， Sephadex LH-20， ODS column chromatography and preparative HPLC etc.， 7 compounds were isolated from the 70% ethanol extract of the fruits of Xanthium chinense. Based on ESI-MS and NMR data， the structures of these compounds were identified as pungiolide O(1)， grasshopper ketone(2)， icariside F₂(3)， 7-[(β-D-apiofuranosyl-(1→6)-β-D-glucopyranosyl)oxymethy]-8，8-dimethyl-4，8-dihydrobenzo[1，4]thiazine-3，5-dione(4)，(6R，9S)-3-oxo-α-ionol β-D-glucopyranoside(5)， cryptochlorogenic acid methyl ester(6)， and chlorogenic acid methyl ester(7). Among them， compound 1 is a new compound.
Chromatography, High Pressure Liquid ; Fruit ; chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Phytochemicals ; isolation & purification ; Sesquiterpenes ; isolation & purification ; Xanthium ; chemistry

Xanthii Fructus is a traditional medicine for the treatment of nasal diseases in clinic, mainly come from the burs of Xanthium sibiricum with a worldwide distribution. By sorting and studying literature of Chinese medicine and comparing different figures recorded with the morphological description of several species from Xanthium (Asteraceae) in the Flora of China, combining the biological investigation in resource survey, the article pointed out that the burs or the whole herbs of X. mongolicum, as well as X. sibiricum, has been used by the traditional Chinese medicine in ancient time. It provides a reference for further studies in the future.
China ; Herbal Medicine ; history ; History, Ancient ; Medicine in Literature ; Medicine, Chinese Traditional ; history ; Xanthium ; anatomy & histology ; classification

The experiment's aim was to optimize the processing technology of Xanthii Fructus which through comparing the difference of UPLC fingerprint and contents of toxicity ingredient in water extract of 16 batches of processed sample. The determination condition of UPLC chromatographic and contents of toxicity ingredient were as follows. UPLC chromatographic: ACQUITY BEH C18 column (2.1 mm x 100 mm, 1.7 microm) eluted with the mobile phases of acetonitrile and 0.1% phosphoric acidwater in gradient mode, the flow rate was 0.25 mL x min(-1) and the detection wavelength was set at 327 nm. Contents of toxicity ingredient: Agilent TC-C18 column (4.6 mm x 250 mm, 5 microm), mobile phase was methanol-0.01 mol x L(-1) sodium dihydrogen phosphate (35: 65), flow rate was 1.0 mL x min(-1), and detection wavelength was 203 nm. The chromatographic fingerprints 16 batches of samples were analyzed in using the similarity evaluation system of chromatographic, fingerprint of traditional Chinese medicine, SPSS16.0 and SIMCA13.0 software, respectively. The similarity degrees of the 16 batches samples were more than 0.97, all the samples were classified into four categories, and the PCA showed that the peak area of chlorogenic acid, 3,5-dicaffeoylquinic acid and caffeic acid were significantly effect index in fingerprint of processed Xanthii Fructus sample. The outcome of determination showed that the toxicity ingredient contents of all samples reduced significantly after processing. This method can be used in optimizing the processing technology of Xanthii Fructus.
Caffeic Acids ; analysis ; toxicity ; Chemistry, Pharmaceutical ; Chromatography, High Pressure Liquid ; methods ; Drugs, Chinese Herbal ; analysis ; toxicity ; Quinic Acid ; analogs & derivatives ; analysis ; toxicity ; Xanthium ; chemistry ; classification

BACKGROUND: Xanthium stramarium (XAS) and Psoralea corylifolia (PSC), phototoxic oriental medicinal plants, has been used in traditional medicines in Asian countries. OBJECTIVE: The effects of highly purified XAS or PSC extract combined with ultraviolet A1 (UVA1) irradiation on cell proliferation and transforming growth factor-beta1 (TGF-beta1) expression of the keloid fibroblast were being investigated to define potential therapeutic uses for keloid treatments. METHODS: The keloid fibroblasts were treated with XAS or PSC alone or in the combination with UVA1 irradiation. The cell viability, apoptosis, and expression of TGF-beta1 and collagen I were investigated. RESULTS: XAS and PSC in combination with UVA1 irradiation suppressed cell proliferation and induced apoptosis of keloid fibroblasts. Furthermore, the XAS and PSC in combination with UVA1 irradiation inhibited TGF-beta1 expression and collagen synthesis in keloid fibroblasts. CONCLUSION: These findings may open up the possibility of clinically used XAS or PSC in combination with UVA1 irradiation for keloid treatments.
Apoptosis ; Asian Continental Ancestry Group ; Cell Proliferation ; Cell Survival ; Collagen ; Fibroblasts ; Humans ; Keloid ; Plants, Medicinal ; Psoralea ; Therapeutic Uses ; Transforming Growth Factor beta1 ; Xanthium

BACKGROUND: Xanthium stramarium (XAS) and Psoralea corylifolia (PSC), phototoxic oriental medicinal plants, has been used in traditional medicines in Asian countries. OBJECTIVE: The effects of highly purified XAS or PSC extract combined with ultraviolet A1 (UVA1) irradiation on cell proliferation and transforming growth factor-beta1 (TGF-beta1) expression of the keloid fibroblast were being investigated to define potential therapeutic uses for keloid treatments. METHODS: The keloid fibroblasts were treated with XAS or PSC alone or in the combination with UVA1 irradiation. The cell viability, apoptosis, and expression of TGF-beta1 and collagen I were investigated. RESULTS: XAS and PSC in combination with UVA1 irradiation suppressed cell proliferation and induced apoptosis of keloid fibroblasts. Furthermore, the XAS and PSC in combination with UVA1 irradiation inhibited TGF-beta1 expression and collagen synthesis in keloid fibroblasts. CONCLUSION: These findings may open up the possibility of clinically used XAS or PSC in combination with UVA1 irradiation for keloid treatments.
Apoptosis ; Asian Continental Ancestry Group ; Cell Proliferation ; Cell Survival ; Collagen ; Fibroblasts ; Humans ; Keloid ; Plants, Medicinal ; Psoralea ; Therapeutic Uses ; Transforming Growth Factor beta1 ; Xanthium

OBJECTIVETo investigate the effects of Xanthium sibiricum Patrin ex Widder water extracts (CEW) on α-glucosidase activity (AG) and blood sugar in mice.

METHODSThe inhibition of AG by CEW was studied with enzyme-inhibitor screening external model with acarbose as control drug. The normal mice were administrated by gavage with 40.0g*kg(-1), or 10.0 g*kg(-1) of CEW, 0.375 g*kg(-1) of acarbose, and 0.3ml of normal saline, respectively in successive 5 days; then the animals were loaded with 2.0 g*kg(-1) of glucose, 4.0 g*kg(-1) of sucrose, and 2.0 g*kg(-1) of starch and blood sugar levels were measured within 15, 30, 60, and 120min. Diabetes was induced by injection of streptozotocin (STZ) in mice, then 40.0 g*kg(-1), or 10.0 g*kg(-1) of CEW was given to diabetic mice in successive 2 weeks and 4 weeks, then the blood sugar levels were measured.

RESULTSIn the enzyme inhibition test, when the concentration of CEW was between 0.3125 g*L(-1)-10.00 g*L(-1), the inhibition rate was 55.42%-92.73% when the concentration of acarbose was 1.5625 g*L(-1)-25.00 g*L(-1), the inhibition rate was 9.28%-64.87%. In the sugar tolerance test, the blood sugar value in starch-loaded mice decreased sharply (P<0.01), followed by sucrose-loaded group (P<0.05), and there was no change in glucose-loaded group (P>0.05). In diabetic mice CEW-40 and CEW-10 groups showed significant blood sugar lowering effect (P<0.01 or P<0.05).

CONCLUSIONCEW has stronger effect in inhibition of AG activity than acarbose. CEW can increase the sugar tolerance in normal mice and decrease the blood sugar level in diabetic mice..

Animals ; Blood Glucose ; drug effects ; metabolism ; Diabetes Mellitus, Experimental ; drug therapy ; Enzyme Inhibitors ; pharmacology ; Female ; Glycoside Hydrolase Inhibitors ; Male ; Mice ; Plant Extracts ; pharmacology ; Xanthium ; chemistry ; alpha-Glucosidases ; metabolism

This study was establish an UPLC fingerprint of Xanthii Fructus from different habitats, to provide a comprehensive evaluation for its quality control. UPLC-PDA was adopted to analysis of 26 baches of Xanthii Fructus from different habitats. The chromatographic condition was as follow: ACQUITY BEH C18 Column (2.1 mm x 100 mm,1.7 microm) eluted with the mobile phases of acetonitrile and 0.1% phosphoric acid water in gradient mode. The flow rate was 0.25 mL x min(-1) and the detection wavelength was set at 220 nm. The fingerprints of 26 batches Xanthii Fructus were carried out by similarity comparation, cluster and the principal component analysis (PCA). There were nineteen common peaks, nine of which had been identified, and the similarity degrees of the twenty-six batches of the samples were between 0.804 and 0.990. All the samples were classified into six categories, and the PCA value of each fingerprint peak was calculated, and six principal components accounted for over 81. 140% of the total variance were extracted from the original data This method can be used to assess the quality of Xanthii Fructus.
China ; Chromatography, High Pressure Liquid ; methods ; Drugs, Chinese Herbal ; analysis ; Ecosystem ; Fruit ; chemistry ; Quality Control ; Xanthium ; chemistry

OBJECTIVETo comparative study the acute toxicity of four extracts from Xanthii Fructus in mice.

METHODObserved the toxic manifestations in mice which were given the four extracts by intragastric administration and calculated the LD50 of the four extracts from Xanthii Fructus.

RESULTThe toxic manifestations of the mice given water extract by intragastric administration were repose, pilo-erection, cyanosis, intention tremor, respiratory inhibition, loss of righting reflex and convulsion . The toxic manifestations of the mice given ethanol extract by intragastric administration were repose, abdominal respiration, intention tremor, intermittent convulsions, incontinence. The LD50 of Xanthii Fructus processed water extract, processed ethanol extract, crude water extract, crude ethanol extract were material drug 155.93, 317.80, 167.6, 275.41 g x kg(-1), respectively.

CONCLUSIONThe acute toxicity of water extract is distinctly stronger than that of ethanol extract, but there is no marked distinguish between crude and processed extract.

Animals ; Chemistry, Pharmaceutical ; methods ; Drugs, Chinese Herbal ; administration & dosage ; isolation & purification ; toxicity ; Female ; Fruit ; chemistry ; Lethal Dose 50 ; Male ; Mice ; Reflex, Righting ; drug effects ; Respiration ; drug effects ; Xanthium ; chemistry