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@#Chemical constituents of n-butanol part of ethanol extract from the leaves of Cyclocarya paliurus (Batalin) Iljinskaja were studied.Eight glycosides were separated and purified by silica gel, MCI, ODS, Sephadex LH-20 column chromatography and semi-preparative high-performance liquid chromatography.Based on the physicochemical properties and spectral data, these compounds were 3-ethyl-4-methyl-pentyl ester-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1), juglanoside E (2), (4S)-α-terpineol-8-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (3), (4S)-α-terpineol-8-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (4), eugenyl-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (5), kaempferol-3-O-β-D-glucuronopyranosyl methylester (6), kaempferol-3-O-β-D-glucuronopyranoside (7), and quercetin-3-O-β-D-glucuronopyranoside (8).Among them, compound 1 was a new compound, and compounds 2-6 were isolated from the genus Cyclocarya for the first time.
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ObjectiveChemical components in ethanol extract of Cyclocarya paliurus dried leaves were analyzed by ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry （UHPLC-Q-TOF/MS）. MethodAn Agilent Poroshell 120 EC-C18 column （3.0 mm×100 mm， 2.7 μm） was used with 0.1% formic acid aqueous solution （A）-acetonitrile （B） as the mobile phase for gradient elution （0-26 min，2%-18%B； 26-60 min， 18%-72%B； 60-70 min， 72%-100%B； 70-71 min， 100%-2%B； 71-72 min， 2%B）， and the flow rate of 0.4 mL·min-1 and injection volume of 3 μL. The electrospray ionization （ESI） was used in positive and negative modes， and detection range was m/z 50-1 100. The collected data were processed by Agilent MassHunter workstation. According to the retention time and MS information of each compound， combined with existing literature and MS database information， the compounds were identified and analyzed for the fragmentation rule. ResultA total of 52， 55 components were identified in the positive and negative ion modes， respectively. Among them， 14 flavonoids， 3 triterpenoids， 15 organic acids and 20 other compounds were identified under positive ion mode， while 18 flavonoids， 9 triterpenoids， 18 organic acids and 10 other compounds were identified under the negative ion mode. By summarizing the positive and negative ion modes and removing the common compounds， 87 compounds were identified， including 22 flavonoids， 27 organic acids， 11 triterpenoids and 27 other compounds. ConclusionUHPLC-Q-TOF/MS can be used to quickly analyze the chemical constituents in C. paliurus dried leaves. 1-Kestose and 18β-glycyrrhetinic acid and other components related to hypoglycemic activity of this herb are identified for the first time， which can provide reference for clarifying the pharmacodynamic substance basis of C. paliurus dried leaves.
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Objective: Based on the method of UPLC fingerprint, multi-component quantification and chemical pattern recognition, the quality of Cyclocarya paliurus from different producing areas was evaluated to provide basis for further development and utilization. Methods: The UPLC fingerprints of 20 batches of C. paliurus from different habitats in five provinces were established to determine the common peaks. Three chemical components were identified and the content of the samples was determined by comparison with the reference materials. Cluster analysis and principal component analysis were carried out by SPSS 22.2 and SIMCA software. Results: A total of 16 chromatographic peaks were selected as the common peaks of the fingerprint, 20 batches of C. paliurus could be divided into six categories by cluster analysis, and the results of principal component analysis and cluster analysis were basically the same; By principal component analysis, the cumulative variance contribution rate of the five principal component factors was 86.765%. The quality of S14 and S15 samples from Enshi, Hubei Province was the best, and S4, S5, S8, and S16 of Xiushui, Jiangxi Province were the second. The content of isoquercetin, quercitrin and afzelin were 0.360%-0.884%, 0.263%-1.097%, and 0.092%-0.403%, respectively, among which the total content of S4, S8, S14, and S15 were the top 4, and that of S18 and S20 was in the last two places. Conclusion: Combined with fingerprint, cluster analysis and principal component analysis, we can evaluate the quality of C. paliurus more comprehensively. Isoquercetin, quercitrin and afzelin can be used as the index components for C. paliurus quality control.
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OBJECTIVE: To investigate the chemical constituents from the leaves of Cyclocarya paliurus. METHODS: Chemical constituents were isolated and purified by column chromatography with silicagel, Sephadex LH - 20, and semi-preparative HPLC. RESULTS: Eleven compounds were isolated from the ethyl acetate extracts of the leaves of Cyclocarya paliurus. Their structures were elucidated as hirsutrin (1), contigoside B (2), kaempferol (3), sterubin (4), syringic acid (5), vanillic acid (6), 2-hydroxy-5-ethoxybenzoic acid (7), 2-methoxy-4-hydroxycinnamic acid (8), cis-p-hydroxycinnamic acid (9), p-hydroxybenzonic acid (10), and phydroxybenzaldehyde (11). CONCLUSION: All the compounds except 3 and 6 are obtained from Cyclocarya paliurus for the first time.
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@#The purpose of this study was to investigate the hypoglycemic effect and the safety of medicinal formula composed of Cyclocarya paliurus and Mulberry leaves. An experimental diabetic rat model was established by high energy diet plus small dosage of auoxan(ALX). At the same time, each group rats were given distilled water(blank and model), metformin(Met), Cyclocarya paliurus aqueous extract(CP), Mulberry leaves aqueous extract(ML)and the different proportions of aqueous extract mixtures of Cyclocarya paliurus and Mulberry leaves(CM1, CM2 and CM3), respectively. Fasting blood glucose(FBG), OGTT, TC, TG, LDL-C, HDL-C, insulin and liver and kidney function related index were gauged to evaluate the hypoglycemic effect and the safety of samples. The results showed that FBG level of the rats in CM1, CM2 and CM3 groups decreased 21. 64%, 16% and 12. 55%, respectively, comparing with that of model group. Moreover, FBG, glucose tolerance and pancreatic tissue morphology were remarkably improved in CM1 group. TC and LDL-C levels of rats in ML and CM3 groups decreased significantly compared with the those of Model group(P< 0. 05), which showed ML and CM3 were beneficial to regulate the blood lipid level in diabetic rats. Furthermore, all the administration groups had no adverse effect on liver function index. The down regulation of kidney function index of CP, ML, CM1, CM2 and CM3 groups comparing with model group indicated that Cyclocarya paliurus and Mulberry leaves could alleviate the injury of liver and kidney. Our results demonstrated that the medicinal formula composed of Cyclocarya paliurus and Mulberry leaves were favorable to reduce blood glucose and can regulate lipid metabolism without liver and kidney toxicity.
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@#To investigate the effect and possible mechanisms of triterpenic acid-enriched fraction from Cyclocarya paliurus(TAE)on glucagon secretion in insulin-resistance pancreatic α cells, the model of insulin resistance in αTC1-6 cells was induced by long term exposure to high glucose. Experimental groups were divided as follow: control(5. 5 mmol/L glucose), model(25 mmol/L), TAE(1, 5, 10 μg/mL), and TAE(10 μg/mL)plus wortmannin(10 nmol/L)group. The supernatant and lysate of treated cells were collected to determine glucagon secretion by ELISA kit. The mRNA and protein abundance of IRS-1, PI3K and Akt were measured by qPCR and Western blot analysis. Results showed that TAE could not only significantly reduce glucagon secretion induce by high glucose in a dose-dependent manner, but also remarkably increased the mRNA and protein abundance of IRS-1, PI3K and Akt in αTC1-6 cells. However, these effects of TAE were reversed by PI3K inhibitor wortmannin. In conclusion, it suggested that TAE could improve the insulin resistance induced by high glucose in pancreatic α cells which may be related with the activation of IRS-1/PI3K/Akt signaling pathway.
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Modern research showed that components in the dried leaf of Cyclocarya paliurus. had various biological activities. The current quality control research was focused on content determination of polysaccharides and flavonoids, while there were less research on quantitative analysis of terpenes and phenolic acids. In this paper, the contents of 16 components of 3 kinds in C. paliurus leaf were determined by UPLC-QE-Orbitrap-MS. The results were as following: good linear relationship of 16 analytes existed within the studied concentration rages (²>0.996), and RSDs were of <3.0% in the precision test and replicate test, with the average recovery rates 95.20%-104.4%, respectively. The results indicatod that the method is simple and accurate, which can be used for the comprehensive quality evaluation of C. paliurus leaf. The established method was applied to determine the contents of 12 batches of C. paliurus leaf from different areas, and the 16 analvtes contents in the samples could be different from several times to dozens times, which indicated that there might be significant quality difference in C. paliurus leaf from different areas.
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Flavonoids , Juglandaceae , Chemistry , Phytochemicals , Plant Leaves , Chemistry , PolysaccharidesABSTRACT
To investigate the therapeutic effects of triterpenoids from Cyclocarya paliurus on non-alcoholic fatty liver disease (NAFLD),the model of NAFLD in HepG2 cells was induced by free fatty acids (FFAs). Cytotoxicity of the triterpenoids from C. paliurus was determined by MTT method,and the effects of triterpenoids without cytotoxicity on intracellular triglyceride (TG)and superoxide dismutase (SOD)were detected by the kits. Data indicated that compound 4 [2α,3α,23-trihydroxy-12,20 (30)-dien-28-ursolic acid,TUA]had hypolipidemic and antioxidant activities. After being treated with TUA and FFAs for 24 h,the intracellular lipid content was observed using Oil Red O staining,and intracellular TG,malondialdehyde (MDA ),SOD and reactive oxygen species (ROS)levels were determined by the assay kits. The protein expression of nuclear factor erythroid 2-related factor 2 (Nrf2),heme oxygenase-1 (HO-1 )and NAD (P)H quinone oxidoreductase 1 (NQO-1 )were measured by Western blot. The results showed that TUA significantly increased SOD activity,and decreased intracellular TG, ROS and MDA levels in FFAs-induced HepG2 cells. Moreover,TUA dramatically improved Nrf2,NQO-1 ,and HO-1 expression. However,the dramatic increase in TG,ROS,MDA levels and the reduction in SOD,NQO-1 and HO-1 expression following Nrf2 inhibitor brusatol treatment were observed. In conclusion,these results suggest that TUA has the therapeutic effect on NAFLD which may be associated with Nrf2 activation.
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AIM To speculate the hypoglycemic mechanism for rats with type 2 diabetes by exploring the therapeutic effects of leaf aqueous extract from Cyclocarya paliurus on liver insulin receptor (InsR) and insulin receptor substrate 2 (IRS-2).METHODS The diabetic rat model was established through intraperitoneal injection of streptozotocin and fed with high-fat diet.The moleled rats were equally assigned into the control group and leaf aqueous extract from Cyclocarya paliurus group (extract group).After the test extract was orally administrated for four weeks,body weight,urine output,food intake,water intake and fasting blood-glucose (FBG) were measured,and the levels of serum insulin,InsR and IRS-2 mRNA in liver tissue were investigated in rats.RESULTS Compared with the control group,the extract group showed a reduction in urine output,food intake,water intake,FBG and insulin levels.Meanwhile,the rats' body weights in extract group were presented a trend to increase.The gene expressions of InsR and IRS-2 in liver tissue were up-regulated.Moreover,the insulin sensitivity was improved.CONCLUSION The leaf aqueous extract from Cyclocarya paliurus can reduce FBS,improve insulin sensitivity,which may be associated with the increase of InsR and IRS-2 gene expression in liver tissue.
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AIM To establish the quality standard for Cyclocarya paliurus (Batal.) ljinsk..METHODS The contents of water,ash and extract in twelve batches of samples were determined.TLC and HPLC were adopted in the qualitative identification and quantitative determination of quercetin and kaempferol,respectively,and phenol-sulfuric acid method was used for the polysaccharide content assessment.RESULTS The average contents of water,total ash,acid-insoluble ash,water-soluble extract and alcohol-soluble extract were 11.05％,5.81％,1.70％,11.25％ and 10.16％,respectively.The clear TLC spots demonstrated their strong specificity.Quercetin and kaempferol showed good linear relationships within the ranges of 0.004 953-0.022 29 mg/mL and 0.005 748-0.028 74 mg/mL (r =0.999 9),whose average recoveries were 97.1％ (RSD =2.59％) and 97.9％ (RSD =2.86％),respectively.Polysaccharide showed a good linear relationship within the range of 0.021 22-0.095 58 mg/mL,whose average recovery was 97.2％ (RSD =2.42％).The contents of three constituents in various batches of samples showed obvious differences.CONCLUSION In C.paliurus,the contents of water,total ash,acid-insoluble ash,water-soluble extract and ethanol-soluble extract should not be more than 13.0％,7.0％,2.0％,13.5％ and 12.0％,while those of quercetin,kaempferol and polysaccharide (calculated by dry product) should not be less than 0.040％,0.070％ and 0.60％,respectively.
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s: Cyclocarya paliurus (Batal.) Iljinsk. polysaccharide (CPPC) has various biological activities including hypolipemic effect, hypoglycemic effect, anti-oxidant effect, anti-tumor effect and immunomodulatiry;especially that hypolipemic effect and hypoglycemic effect have become the research hotspots in recent years. This article reviewed extraction, purification, content determination and biological activity of CPPC in the latest decade, with a purpose to provide references for the deep research and industrial development CPPC.
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Objective: To extract and isolate polysaccharide from Cyclocarya paliurus leaves, characterize its structural features and study its α-glucosidase inhibitory effect. Methods: C. paliurus polysaccharide (CP50) was isolated and purified by water extraction and ethanol precipitation, deproteinization with 732 cation exchange resin and 50% ethanol precipitation. Molecular weight of CP50 was determined by high performance gel permeation chromatography-multiple angle laser light scattering (HPGPC-MALLS), and monosaccharide composition was analyzed by HPLC with PMP (1-phenyl-3-methyl-5-pyrazolone) pre-column derivatization. The structure of CP50 was characterized by methylation, Fourier transform infrared spectroscopy (FT-IR), and proton nuclear magnetic resonance spectrum (1H-NMR), respectively. The α-glucosidase inhibitory effect of CP50 was investigated by PNPG method. Results: The molecular weight of CP50 was 59 000. It contained eight kinds of monosaccharides including galacturonic acid, glucose, galactose, arabinose, mannose, xylose, rhamnose, and glucuronic acid with molar ratio of 29.1:25.6:16.5:9.3:6.7:6.1:4.1:2.6. CP50 was mainly composed of →4) GalA (1→, →4) Glc (1→ and →4) Gal (1→ with branches at C-6 position of galactose. Furthermore, our results showed that CP50 exhibited a potent inhibitory effect on α-glucosidase, and the value of IC50 was determined to be 3.3 μg/mL which was much lower than the anti-type 2 diabetes drug acarbose (193.6 μg/mL). The inhibitory mode belongs to the mixed noncompetitive inhibition. Conclusion: CP50 is a pectin-like acidic polysaccharide with complex structure. Moreover, CP50 possesses better α-glucosidase inhibitory effect and potential value for the drug development and utilization.
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Objective To study the chemical constituents from the leaves of Cyclocarya paliurus. Methods The compounds were isolated and purified by chromatographic techniques and their structures were identified on the basis of spectral features. Results Forteen known compounds, including 11 flavonoids and three phenolic acids, named kaempferol (1), quercetin (2), apigenin (3), tricin (4), eupatilin (5), 3,7,8,3'-tetrahydroxy-4'-methoxyflavone (6), myricetin (7), 3,5-dihydroxy-7-methoxy-3',4'-methylenedioxyflavone (8), isoquercitrin (9), quercetin-3-O-β-D-glucuronide (10), myricetin-3-O-β-D-glucuronide (11), caffeic acid (12), 5-caffeoylquinic acid (13), and 3-hydroxybenzoic acid-4-O-β-D-glucopyranoside (14) were isolated from the leaves of C. paliurus. Conclusion Compounds 3, 4, 5, and 14 are firstly obtained from C. paliurus. Compounds 6 and 8 are isolated from the genus of Cyclocarya for the first time. Compounds 1-11 showed moderate active against the brine shrimp larvae, and compounds 12-14 indicated significant growth inhibitory activity against the brine shrimp (Artemia salina) larvae.
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Cyclocarya paliurus(Batal.)Iljinskaja,a Chinese native plant,contains various components of bioactive constitu-ents in leaves. The main chemical constituents are triterpenes,flavonoids,organic acids,polysaccharides,steroids,etc. and among them,the dammarane-type triterpenoids are the main sweet components. Modern pharmacological research has demonstrated that these compounds or plant extracts show hypoglycemic,lipid-lowering,blood pressure lowering,antioxidation,and antibacterial activi-ties,and so on. The research advances in chemical constituents and pharmacological effect of C. paliurus are reviewed for a prospect reference of its further development and utilization.
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AIM To study the chemical constituents from the leaves of Cyclocarya paliurus (Batal.) lljinskaja.METHODS The ethyl acetate fraction of methanol extract from C.paliurus leaves was isolated and purified by silica,ODS and semi-preparative HPLC,then the structures of obtained compounds were identified by spectral data.RESULTS Eleven compounds were isolated and identified as (6S,7R,8R)-7α-[(β-glucopyranosyl) oxy] lyoniresinol (1),lyoniside (2),(-)-lyoniresinol 3 α-O-β-D-xylopyranoside (3),dihydrodehydrodiconiferyl alcohol 4'-O-β-D-glucoside (4),kaempferol-3-O-α-L-rhamnoside (5),kaempferol-3-O-α-L-(4"-Z-p-cumaroyl)-rhamnoside (6),naringenin (7),4'-hydroxywogonin (8),1-(3',4'-dihydroxyphenyl)-7-(4"-hydroxyphenyl)-4-hepten-3-one (9),grasshopper ketone (10),p-hydroxybenzoic acid (11).CONCLUSION Except for compounds 5,11,all the compounds are isolated from this plant for the first time.
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AIM:To investigate the therapeutic effect of Qingqianliu ( QQL) antidiabetic prescription , contai-ning Cyclocarya paliurus, on type 2 diabetic rats.METHODS: Ten rats were randomly chosen as normal control group , and other rats were used to establish diabetic rat models by high-fat diet feeding plus streptocin intraperitoneal injection . Successfully modeling rats were randomly divided into high (300 mg· kg -1· d-1), medium (150 mg· kg-1· d-1) and low (75 mg· kg-1· d-1) doses of QQL treatment groups, and model control group (10 rats in each group).The rats re-ceived daily treatment for 6 weeks.Meanwhile, the therapeutic effect of QQL on these type 2 diabetic rats were evaluated via the body weight , the levels of serum glucose , insulin and glycosylated hemoglobin , the glucose tolerance , the pathologi-cal changes of pancreatic islands , antioxidative indexes and inflammaory factors .RESULTS:Compared with model control group, the body weight, serum insulin, glucose tolerance, serum SOD and serum GSH were increased , the serum glucose, glycosylated hemoglobin , MDA, IL-1βand TNF-αwere decreased , and the pathological changes of pancreatic islands were improved in type 2 diabetic rats with QQL treatment at high and low doses (P<0.05 or P<0.01).CONCLUSION:The QQL reduces the blood glucose , improves the glucose tolerance , and attenuates the damage of pancreatic islands .Its me-chanism may be related to antioxidative and anti-inflammatory effects .
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AIM To study the chemical constituents from the leaves of Cyclocarya paliurus (Batal.) lljinskaja.METHODS The ethyl acetate fraction of methanol extract from C.paliurus leaves was isolated and purified by silica,ODS and semi-preparative HPLC,then the structures of obtained compounds were identified by spectral data.RESULTS Eleven compounds were isolated and identified as (6S,7R,8R)-7α-[(β-glucopyranosyl) oxy] lyoniresinol (1),lyoniside (2),(-)-lyoniresinol 3 α-O-β-D-xylopyranoside (3),dihydrodehydrodiconiferyl alcohol 4'-O-β-D-glucoside (4),kaempferol-3-O-α-L-rhamnoside (5),kaempferol-3-O-α-L-(4"-Z-p-cumaroyl)-rhamnoside (6),naringenin (7),4'-hydroxywogonin (8),1-(3',4'-dihydroxyphenyl)-7-(4"-hydroxyphenyl)-4-hepten-3-one (9),grasshopper ketone (10),p-hydroxybenzoic acid (11).CONCLUSION Except for compounds 5,11,all the compounds are isolated from this plant for the first time.
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AIM:To investigate the therapeutic effect of Qingqianliu ( QQL) antidiabetic prescription , contai-ning Cyclocarya paliurus, on type 2 diabetic rats.METHODS: Ten rats were randomly chosen as normal control group , and other rats were used to establish diabetic rat models by high-fat diet feeding plus streptocin intraperitoneal injection . Successfully modeling rats were randomly divided into high (300 mg· kg -1· d-1), medium (150 mg· kg-1· d-1) and low (75 mg· kg-1· d-1) doses of QQL treatment groups, and model control group (10 rats in each group).The rats re-ceived daily treatment for 6 weeks.Meanwhile, the therapeutic effect of QQL on these type 2 diabetic rats were evaluated via the body weight , the levels of serum glucose , insulin and glycosylated hemoglobin , the glucose tolerance , the pathologi-cal changes of pancreatic islands , antioxidative indexes and inflammaory factors .RESULTS:Compared with model control group, the body weight, serum insulin, glucose tolerance, serum SOD and serum GSH were increased , the serum glucose, glycosylated hemoglobin , MDA, IL-1βand TNF-αwere decreased , and the pathological changes of pancreatic islands were improved in type 2 diabetic rats with QQL treatment at high and low doses (P<0.05 or P<0.01).CONCLUSION:The QQL reduces the blood glucose , improves the glucose tolerance , and attenuates the damage of pancreatic islands .Its me-chanism may be related to antioxidative and anti-inflammatory effects .
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Objective To study the leaf morphology and structure of Cyclocarya paliurus.Methods Foliar maceration,preparation of venation order,sectioning paraffin blocks,and scanning electron microscope were used to study the leaf morphology and structure.Results Cuticular papillates,glandular hairs,peltate scales,and non-glandular hairs presented on the leaf epidermis of C.paliurus.Anomocytic stomata were confined to the lower epidermis.Large cluster crystals existed in the uppermost layer of palisade cells.Midrib included one closed vascular system and one additional vascular strand.Secondary veins are semicraspedodromous and form marginal loops,tertiary veins are percurrent,quaternary veins form orthogonal or polygonal areoles filled up by branched and freely ended veinlets.Conclusion These structure characteristics are first reported and are useful for leaf identification of C.paliurus from other Juglandaceae plants.