36 results on '"Xuan, Zhang"'
Search Results
2. Zeylleucapenoids A–D, Highly Oxygenated Diterpenoids with Anti-Inflammatory Activity from Leucas zeylanica (L.) R. Br.
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Ting Zhao, Xuan Zhang, Xu-Hua Nong, Xue-Ming Zhou, Ru-Ru Chai, Xiao-Bao Li, and Guang-Ying Chen
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Leucas zeylanica ,highly oxygenated ,diterpenoids ,anti-inflammatory activity ,molecular docking ,zebrafish model ,Organic chemistry ,QD241-441 - Abstract
Four previously undescribed highly oxygenated diterpenoids (1–4), zeylleucapenoids A–D, characterized by halimane and labdane skeletons, were isolated from the aerial parts of Leucas zeylanica. Their structures were elucidated primarily via NMR experiments. The absolute configuration of 1 was established using theoretical ECD calculations and X-ray crystallographic analysis, whereas those for 2–4 were assigned using theoretical ORD calculations. Zeylleucapenoids A–D were tested for anti-inflammatory activity against nitric oxide (NO) production in RAW264.7 macrophages, of which only 4 showed significant efficacy with an IC50 value of 38.45 μM. Further, active compound 4 was also evaluated for the inhibition of the release of pro-inflammatory cytokines TNF-α and IL-6 and was found to have a dose-dependent inhibitory effect, while it showed nontoxic activity for zebrafish embryos. A subsequent Western blotting experiment revealed that 4 inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, molecular docking analysis indicated that the possible mechanism of action for 4 may be bind to targets via hydrogen and hydrophobic bond interactions.
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- 2023
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3. Germacrane Sesquiterpene Dilactones from Mikania micrantha and Their Antibacterial and Cytotoxic Activity
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Li-Mei Dong, Qiao-Lin Xu, Shao-Bo Liu, Shan-Xuan Zhang, Meng-Fei Liu, Jin-Long Duan, Jin-Kui Ouyang, Jia-Tao Hu, Fen-Yu Fu, and Jian-Wen Tan
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Mikania micrantha ,germacrane sesquiterpene ,antibacterial ,anti-MRSA ,cytotoxicity ,Organic chemistry ,QD241-441 - Abstract
Four new germacrane sesquiterpene dilactones, 2β-hydroxyl-11β,13-dihydrodeoxymikanolide (1), 3β-hydroxyl-11β,13-dihydrodeoxymikanolide (2), 1α,3β-dihydroxy-4,9-germacradiene-12,8:15,6-diolide (3), and (11β,13-dihydrodeoxymikanolide-13-yl)-adenine (4), together with five known ones (5–9) were isolated from the aerial parts of Mikania micrantha. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compound 4 is featured with an adenine moiety in the molecule, which is the first nitrogen-containing sesquiterpenoid so far isolated from this plant species. These compounds were evaluated for their in vitro antibacterial activity against four Gram-(+) bacteria of Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC) and Curtobacterium. flaccumfaciens (CF), and three Gram-(–) bacteria of Escherichia coli (EC), Salmonella. typhimurium (SA), and Pseudomonas Solanacearum (PS). Compounds 4 and 7–9 were found to show strong in vitro antibacterial activity toward all the tested bacteria with the MIC values ranging from 1.56 to 12.5 µg/mL. Notably, compounds 4 and 9 showed significant antibacterial activity against the drug-resistant bacterium of MRSA with MIC value 6.25 µg/mL, which was close to reference compound vancomycin (MIC 3.125 µg/mL). Compounds 4 and 7–9 were further revealed to show in vitro cytotoxic activity toward human tumor A549, HepG2, MCF-7, and HeLa cell lines, with IC50 values ranging from 8.97 to 27.39 μM. No antibacterial and cytotoxic activity were displayed for the other compounds. The present research provided new data to support that M. micrantha is rich in structurally diverse bioactive compounds worthy of further development for pharmaceutical applications and for crop protection in agricultural fields.
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- 2023
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4. Polycyclic Phenol Derivatives from the Leaves of Spermacoce latifolia and Their Antibacterial and α-Glucosidase Inhibitory Activity
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Shao-Bo Liu, Lei Zeng, Qiao-Lin Xu, Ying-Le Chen, Tao Lou, Shan-Xuan Zhang, and Jian-Wen Tan
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Spermacoce latifolia ,phenol derivative ,antibacterial ,anti-MRSA ,α-glucosidase inhibitor ,Organic chemistry ,QD241-441 - Abstract
Three new polycyclic phenol derivatives, 2-acetyl-4-hydroxy-6H-furo [2,3-g]chromen-6-one (1), 2-(1′,2′-dihydroxypropan-2′-yl)-4-hydroxy-6H-furo [2,3-g][1]benzopyran-6-one (2) and 3,8,10-trihydroxy-4,9-dimethoxy-6H-benzo[c]chromen-6-one (8), along with seven known ones (3–7, 9 and 10) were isolated for the first time from the leaves of Spermacoce latifolia. Their structures were determined by spectroscopic analysis and comparison with literature-reported data. These compounds were tested for their in vitro antibacterial activity against four Gram-(+) bacteria: Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC), Bacillus subtilis (BS), and the Gram-(−) bacterium Escherichia coli. Compounds 1, 2, 5 and 8 showed antibacterial activity toward SA, BC and BS with MIC values ranging from 7.8 to 62.5 µg/mL, but they were inactive to MRSA. Compound 4 not only showed the best antibacterial activity against SA, BC and BS, but it further displayed significant antibacterial activity against MRSA (MIC 1.95 µg/mL) even stronger than vancomycin (MIC 3.9 µg/mL). No compounds showed inhibitory activity toward E. coli. Further bioassay indicated that compounds 1, 4, 5, 6, 8 and 9 showed in vitro α-glucosidase inhibitory activity, among which compound 9 displayed the best α-glucosidase inhibitory activity with IC50 value (0.026 mM) about 15-fold stronger than the reference compound acarbose (IC50 0.408 mM). These results suggested that compounds 4, 8 and 9 were potentially highly valuable compounds worthy of consideration to be further developed as an effective anti-MRSA agent or effective α-glucosidase inhibitors, respectively. In addition, the obtained data also supported that S. latifolia was rich in structurally diverse bioactive compounds worthy of further investigation, at least in searching for potential antibiotics and α-glucosidase inhibitors.
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- 2022
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5. Determination of Methylene Blue and Its Metabolite Residues in Aquatic Products by High-Performance Liquid Chromatography–Tandem Mass Spectrometry
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Xuan Zhang, Yunhua Hui, Changling Fang, Yuan Wang, Feng Han, Xiaoyi Lou, Essy Kouadio Fodjo, Youqiong Cai, and Cong Kong
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high-performance liquid chromatography–tandem mass spectrometry ,methylene blue ,disinfectant ,aquatic products ,Organic chemistry ,QD241-441 - Abstract
A sensitive and reliable method was developed to determine methylene blue (MB) and its metabolite residues, including azure A (AZA), azure B (AZB), and azure C (AZC) in aquatic products by HPLC–MS/MS. The samples were extracted by acetonitrile and cleaned up by alumina-neutral (ALN) cartridges. The analytes were separated on a Sunfire C18 column (150 mm × 2.1 mm, 5 µm). The method was validated according to the European criteria of Commission Decision 2002/657/CE. Good linearity between 1–500 µg/L was obtained with correlation coefficients (R2) greater than 0.99. The limit of quantification (LOQ) was 1.0 µg/kg. The average recoveries at three levels of each compound (1, 5, and 10 µg/kg) were demonstrated to be in the range of 71.8–97.5%, with relative standard deviations (RSDs) from 1.05% to 8.63%. This method was suitable for the detection of methylene blue and its metabolite residues in aquatic products.
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- 2021
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6. Carbon Nanotube Fibers Decorated with MnO2 for Wire-Shaped Supercapacitor
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Luman Zhang, Xuan Zhang, Jian Wang, David Seveno, Jan Fransaer, Jean-Pierre Locquet, and Jin Won Seo
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carbon nanotube fiber ,CNT–MnO2 hybrid composite ,wire-shaped supercapacitor ,flexible electrode ,Organic chemistry ,QD241-441 - Abstract
Fibers made from CNTs (CNT fibers) have the potential to form high-strength, lightweight materials with superior electrical conductivity. CNT fibers have attracted great attention in relation to various applications, in particular as conductive electrodes in energy applications, such as capacitors, lithium-ion batteries, and solar cells. Among these, wire-shaped supercapacitors demonstrate various advantages for use in lightweight and wearable electronics. However, making electrodes with uniform structures and desirable electrochemical performances still remains a challenge. In this study, dry-spun CNT fibers from CNT carpets were homogeneously loaded with MnO2 nanoflakes through the treatment of KMnO4. These functionalized fibers were systematically characterized in terms of their morphology, surface and mechanical properties, and electrochemical performance. The resulting MnO2–CNT fiber electrode showed high specific capacitance (231.3 F/g) in a Na2SO4 electrolyte, 23 times higher than the specific capacitance of the bare CNT fibers. The symmetric wire-shaped supercapacitor composed of CNT–MnO2 fiber electrodes and a PVA/H3PO4 electrolyte possesses an energy density of 86 nWh/cm and good cycling performance. Combined with its light weight and high flexibility, this CNT-based wire-shaped supercapacitor shows promise for applications in flexible and wearable energy storage devices.
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- 2021
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7. Quantitative 1H Nuclear Magnetic Resonance Method for Assessing the Purity of Dipotassium Glycyrrhizinate
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Yuan-Yuan Zhang, Jie Zhang, Wen-Xuan Zhang, Yue Wang, Ying-Hong Wang, Qing-Yun Yang, and Song Wu
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qNMR ,dipotassium glycyrrhizinate ,methodology validation ,purity ,Organic chemistry ,QD241-441 - Abstract
A simple, rapid, accurate, and selective quantitative method based on 1H nuclear magnetic resonance (qNMR) was successfully established and developed for assessing the purity of dipotassium glycyrrhizinate (KG). In this study, using potassium hydrogen phthalate and fumaric acid as internal standard (IS), several important experimental parameters, such as relaxation delay and pulse angle, were explored. Reliability, specificity, linearity, limit of quantification, precision, stability, and accuracy were also validated. Calibration results obtained from qNMR were consistent with those obtained from HPLC coupled with ultraviolet detection. The proposed method, independent of the reference standard substance, is a useful, reliable, and practical protocol for the determination of KG and glycyrrhizin analogs.
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- 2021
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8. A New and Efficient Synthesis of 6-O-Methylscutellarein, the Major Metabolite of the Natural Medicine Scutellarin
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Wei Zhang, Ze-Xi Dong, Ting Gu, Nian-Guang Li, Peng-Xuan Zhang, Wen-Yu Wu, Shao-Peng Yu, Yu-Ping Tang, Jian-Ping Yang, and Zhi-Hao Shi
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scutellarin ,scutellarein ,6-O-methylscutellarein ,metabolite ,synthesis ,Organic chemistry ,QD241-441 - Abstract
In this paper, a new and efficient synthesis of 6-O-methylscutellarein (3), the major metabolite of the natural medicine scutellarin, is reported. Two hydroxyl groups at C-4′ and C-7 in 2 were selectively protected by chloromethyl methyl ether after the reaction conditions were optimized, then 6-O-methyl-scutellarein (3) was produced in high yield after methylation of the hydroxyl group at C-6 and subsequent deprotection of the two methyl ether groups.
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- 2015
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9. Evaluation of a Triple-Helical Peptide with Quenched Fluorophores for Optical Imaging of MMP-2 and MMP-9 Proteolytic Activity
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Xuan Zhang, Jamee Bresee, Philip P. Cheney, Baogang Xu, Manishabrata Bhowmick, Mare Cudic, Gregg B. Fields, and Wilson Barry Edwards
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matrix metalloproteinase-2 (MMP-2) ,MMP-9 ,gelatinase ,triple-helical peptides ,optical imaging ,fluorescence molecular tomography (FMT) ,Organic chemistry ,QD241-441 - Abstract
Matrix metalloproteinases (MMP) 2 and 9, the gelatinases, have consistently been associated with tumor progression. The development of gelatinase-specific probes will be critical for identifying in vivo gelatinoic activity to understand the molecular role of the gelatinases in tumor development. Recently, a self-assembling homotrimeric triple-helical peptide (THP), incorporating a sequence from type V collagen, with high substrate specificity to the gelatinases has been developed. To determine whether this THP would be suitable for imaging protease activity, 5-carboxyfluorescein (5FAM) was conjugated, resulting in 5FAM3-THP and 5FAM6-THP, which were quenched up to 50%. 5FAM6-THP hydrolysis by MMP-2 and MMP-9 displayed kcat/KM values of 1.5 × 104 and 5.4 × 103 M−1 s−1, respectively. Additionally 5FAM6-THP visualized gelatinase activity in gelatinase positive HT-1080 cells, but not in gelatinase negative MCF-7 cells. Furthermore, the fluorescence in the HT-1080 cells was greatly attenuated by the addition of a MMP-2 and MMP-9 inhibitor, SB-3CT, indicating that the observed fluorescence release was mediated by gelatinase proteolysis and not non-specific proteolysis of the THPs. These results demonstrate that THPs fully substituted with fluorophores maintain their substrate specificity to the gelatinases in human cancer cells and may be useful in in vivo molecular imaging of gelatinase activity.
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- 2014
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10. A Ferulic Acid Derivative FXS-3 Inhibits Proliferation and Metastasis of Human Lung Cancer A549 Cells via Positive JNK Signaling Pathway and Negative ERK/p38, AKT/mTOR and MEK/ERK Signaling Pathways
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Shi-Jun Yue, Peng-Xuan Zhang, Yue Zhu, Nian-Guang Li, Yan-Yan Chen, Jia-Jia Li, Sai Zhang, Ru-Yi Jin, Hao Yan, Xu-Qin Shi, Yu-Ping Tang, and Jin-Ao Duan
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FA derivatives ,lung cancer A549 cells ,ERK/p38 ,JNK ,AKT/mTOR ,MEK/ERK ,Organic chemistry ,QD241-441 - Abstract
Lung cancer is one of the most common malignancies and is an increasing cause of cancer-related deaths. In our previous study, a series of ferulic acid (FA) derivatives were designed and synthesized; they exhibited positive anti-cancer activities, especially for a compound labelled FXS-3. In this study, a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay was performed, wherein it revealed the inhibitory effect of FXS-3 on the proliferation and metastasis of human lung cancer A549 cells. The further flow cytometry assay showed that FXS-3 induced apoptosis of A549 cells induced cell cycle arrest at the G0/G1 phase. The trans-well migration and Matrigel invasion assays revealed that FXS-3 inhibited the migration and invasion of A549 cells. By the western blotting analysis, FXS-3 increased the expression of B-cell lymphoma-2 (Bcl-2) associated X protein (Bax)/Bcl-2 ratio, inhibited matrix metalloproteinase (MMP)-2 and MMP-9, and regulated the extracellular signal-regulated kinase (ERK)/p38, c-Jun N-terminal kinase (JNK), protein kinase B (AKT)/mechanistic target of rapamycin (mTOR), as well as mitogen-activated protein kinase (MEK)/ERK signaling pathways. The subsequent A549 xenograft-bearing mouse model and tail vein injection of A549 cells induced pulmonary tumor metastasis model showed that FXS-3 significantly restrained the tumor growth and metastasis. In conclusion, FXS-3 might inhibit proliferation and metastasis of human lung cancer A549 cells by positively regulating JNK signaling pathway and negativly regulating ERK/p38, AKT/mTOR, and MEK/ERK signaling pathways, which provides important scientific basis for the development of anti-cancer drugs about FA derivatives.
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- 2019
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11. Effect of 2″-O-Rhamnosyl Icariside II, Baohuoside I and Baohuoside II in Herba Epimedii on Cytotoxicity Indices in HL-7702 and HepG2 Cells
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Lin Zhang, Ting Wang, Bao-Sheng Zhao, Jing-Xuan Zhang, Song Yang, Chun-Lan Fan, and Pin Li
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cytotoxicity ,2″-O-rhamnosyl icariside II ,baohuoside I ,baohuoside II ,Organic chemistry ,QD241-441 - Abstract
Herba Epimedii, a commonly used Chinese medicine, has attracted much attention recently because of its potential hepatotoxic effects. 2″-O-Rhamnosyl icariside II, baohuoside I and baohuoside II are the main components of Herba Epimedii, and previous research indicates that these three compounds are related to the hepatotoxicity of Herba Epimedii. To test this idea, in this study, HL-7702 and HepG2 cells were chosen as the in vitro models and the influences of these three compounds on a series of cytotoxicity indices, including ALT, AST, LDH, SOD, GSH, MDA, ROS and MMP, were determined. The results showed that at certain concentrations, the three compounds had different effects on the indices. Among them, baohuoside I at high concentration (32 μg/mL) displayed more significant cytotoxicity than the other two compounds; therefore, it was inferred to be more closely correlated with the liver injury induced by Herba Epimedii combined with the previous study, and its toxic mechanisms may be involved in increasing oxidative stress and inducing apoptosis. The findings of this study may provide evidence of the toxic composition of Herba Epimedii to preliminarily discuss the toxic mechanisms and provide improved guidance for its clinical safety.
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- 2019
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12. Phenolic Composition, Antioxidant Properties, and Inhibition toward Digestive Enzymes with Molecular Docking Analysis of Different Fractions from Prinsepia utilis Royle Fruits
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Xuan Zhang, Yijia Jia, Yanli Ma, Guiguang Cheng, and Shengbao Cai
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hydrogen bond ,oxidative stress ,phenolic composition ,pancreatic lipase inhibition ,α-glucosidase inhibitor ,UHPLC-ESI-HRMS/MS ,Organic chemistry ,QD241-441 - Abstract
The present study investigated the phenolic profiles and antioxidant properties of different fractions from Prinsepia utilis Royle fruits using molecular docking analysis to delineate their inhibition toward digestive enzymes. A total of 20 phenolics was identified and quantified. Rutin, quercetin-3-O-glucoside, and isorhamnetin-3-O-rutinoside were the major phenolic compounds in the total phenolic fraction and flavonoid-rich fraction. The anthocyanin-rich fraction mainly contained cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside. All of the fractions exhibited strong radical scavenging activities and good inhibition on cellular reactive oxygen species (ROS) generation in H2O2-induced HepG2 cells, as evaluated by DPPH and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays. Moreover, the powerful inhibitory effects of those fractions against pancreatic lipase and α-glucosidase were observed. The major phenolic compounds that were found in the three fractions also showed good digestive enzyme inhibitory activities in a dose-dependent manner. Molecular docking analysis revealed the underlying inhibition mechanisms of those phenolic standards against digestive enzymes, and the theoretical analysis data were consistent with the experimental results.
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- 2018
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13. The Design and Synthesis of a New Class of RTK/HDAC Dual-Targeted Inhibitors
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Wei Lu, Jia Li, Xuan Zhang, Yi Chen, and Mingbo Su
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receptor tyrosine kinases ,histone deacetylase ,antitumor ,synergistic effect ,dual inhibitor ,Organic chemistry ,QD241-441 - Abstract
Over the years, the development of targeted medicines has made significant achievements. As a typical example, receptor tyrosine kinases (RTK) inhibitors have become important chemotherapy drugs for a variety of cancers. However, the effectiveness of these agents is always hindered by poor response rates and acquired drug resistance. In order to overcome these limitations, several dual-targeted inhibitors with quinazoline core were designed and synthesized. Though these compounds can simultaneously inhibit histone deacetylases (HDAC) as well as RTK, the structure-activity relationship (SAR) is still not clear enough. To further explore this type of dual-targeted inhibitors, a new class of quinazoline derivatives were designed and synthesized. Their activity evaluations include in vitro inhibitory activity of HDAC, epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2). The SAR study indicated that the introduction of polar group such as hydroxamate on the 4-position of the quinazoline core is more likely to provide a potent HDACi/HER2i hybrid rather than HDACi/EGFRi molecule.
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- 2013
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14. Potent Anti-HIV Activities and Mechanisms of Action of a Pine Cone Extract from Pinus yunnanensis
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Yong-Tang Zheng, Hao-Zhi Li, Ya-Juan Liu, Guang-Ming Liu, Xuan Zhang, Liu-Meng Yang, Chang-Bo Zheng, and Yong-Jun Lv
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Pinus yunnanensis ,pine cone ,anti-HIV activity ,reverse transcriptase ,fusion ,Organic chemistry ,QD241-441 - Abstract
The anti-HIV activities of a pine cone extract (YNS-PY-F) from Pinus yunnanensis have been evaluated, and its mechanisms of action were also explored. The pine cone extract, YNS-PY-F, potently inhibited HIV-1IIIB, HIV-1RF, HIV-1A17, HIV-1AO18 and HIV-2ROD and induced cytopathic effect in C8166 cells with EC50 values of 0.96 μg/mL, 1.53 μg/mL, 0.88 μg/mL, 7.20 μg/mL and 6.17 μg/mL, respectively. The quantification of a p24 production assay showed that YNS-PY-F significantly inhibited the acute replication of HIV-1IIIB, HIV-1RF, HIV-1A17 and HIV-1AO18 in C8166 cells. An MTT assay showed that YNS-PY-F also significantly inhibited the HIV-1IIIB induced cytolysis in MT-4 cells with an EC50 value of 2.22 μg/mL. The mechanism assays showed that YNS-PY-F had potent inhibitory effects on the fusion between infected cells and uninfected cells, and the activity of HIV-1 reverse transcriptase, with EC50 values of 7.60 μg/mL and 4.60 μg/mL, respectively. Overall, these data suggest that the pine cone extract from Pinus yunnanensis has potent inhibitory activities against HIV-1IIIB, HIV-1RF, RT inhibitor-resistant strains HIV-1A17 and HIV-1AO18, and HIV-2ROD, and its anti-HIV mechanisms include inhibition of HIV entry and inhibition of reverse transcriptase activity.
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- 2012
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15. Synthesis of the Key Intermediate of Coenzyme Q10
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Yuan-Gang Zu, Ping Yu, Xuan Zhang, Yu-Jie Fu, Fan-Song Mu, and Meng Luo
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p-toluenesulfonyl chloride ,isoprene ,2,3,4,5-tetramethoxytoluene ,(2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene ,Organic chemistry ,QD241-441 - Abstract
(2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p-toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p-toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation to compound 3, followed by the addition of 2,3,4,5-tetramethoxytoluene (TeMT), assembled the two parts into compound 4. The key parameters of each reaction were optimized at the same time, and the four total operations needed to produced compound 4 had a 27.9% overall yield under the optimized conditions. The structures of the compounds were characterized by 1H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process.
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- 2011
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16. Efficient Lewis Acid Ionic Liquid-Catalyzed Synthesis of the Key Intermediate of Coenzyme Q10 under Microwave Irradiation
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Thomas Efferth, Guoyong Sun, Ping Yu, Yujie Fu, Xuan Zhang, Yue Chen, and Yuangang Zu
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ionic liquids ,FT-IR ,acidity ,microwave irradiation ,Organic chemistry ,QD241-441 - Abstract
An efficient synthesis of a valuable intermediate of coenzyme Q10 by microwave-assisted Lewis acidic ionic liquid (IL)-catalyzed Friedel-Crafts alkylation is reported. The acidity of six [Etpy]BF4-based ionic liquids was characterized by means of the FT-IR technique using acetonitrile as a molecular probe. The catalytic activities of these ionic liquids were correlated with their Lewis acidity. With increasing Lewis acid strength of the ionic liquids, their catalytic activity in the Friedel-Crafts reaction increased, except for [Etpy]BF4-AlCl3. The effects of the reaction system, the molar fraction of Lewis acid in the Lewis acid ILs and heating techniques were also investigated. Among the six Lewis acid ionic liquids tested [Etpy]BF4-ZnCl2 showed the best catalytic activity, with a yield of 89% after a very short reaction time (150 seconds). This procedure has the advantages of higher efficiency, better reusability of ILs, energy conservation and eco-friendliness. The method has practical value for preparation of CoQ10 on an industrial scale.
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- 2010
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17. Compound K Induces Endoplasmic Reticulum Stress and Apoptosis in Human Liver Cancer Cells by Regulating STAT3
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Xuan Zhang, Silin Zhang, Qitong Sun, Wenjun Jiao, Yan Yan, and Xuewu Zhang
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ginsenoside ,CK ,apoptosis ,STAT3 ,ERS ,hepatoma ,Organic chemistry ,QD241-441 - Abstract
The ginsenoside compound K (20-O-β-d-glucopyranosyl-20(S)-protopanaxadiol; CK) is an intestinal bacterial metabolite of ginseng protopanaxadiol saponin that has been reported to induce apoptosis in many cancer cells; however, the precise mechanisms of its activity in human hepatocellular carcinoma (HCC) cells remain unclear. Herein, we demonstrated that CK inhibited the growth and colony formation of HepG2 and SMMC-7721 cells, phenotypes that were mediated by inducing apoptosis. Meanwhile, CK showed lower toxicity in normal hepatoma cells. After treating HepG2 and SMMC-7721 cells with CK, p-STAT3 levels decreased, the three branches of the unfolded protein response were activated, and levels of endoplasmic reticulum stress (ERS)-related proteins were increased. We also revealed that CK decreased the DNA-binding capacity of STAT3. Moreover, silencing STAT3 with CRISPR/Cas9 technology enhanced CK-induced ERS and apoptosis. Finally, we showed that CK inhibited the growth of liver cancer xenografts with little toxicity. Mice bearing human HCC xenografts that were treated with CK showed increased GRP78 expression and decreased p-STAT3 levels. Taken together, these data showed that CK induced ERS and apoptosis by inhibiting p-STAT3 in human liver cancer cells; thus, CK might be a potential therapeutic candidate for human HCC.
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- 2018
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18. Determination of Methylene Blue and Its Metabolite Residues in Aquatic Products by High-Performance Liquid Chromatography–Tandem Mass Spectrometry
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Cong Kong, Youqiong Cai, Yuan Wang, Xiaoyi Lou, Feng Han, Essy Kouadio Fodjo, Yunhua Hui, Changling Fang, and Xuan Zhang
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Analyte ,Metabolite ,Pharmaceutical Science ,Organic chemistry ,Azure A ,Tandem mass spectrometry ,High-performance liquid chromatography ,Article ,Analytical Chemistry ,chemistry.chemical_compound ,QD241-441 ,Limit of Detection ,Tandem Mass Spectrometry ,Drug Discovery ,Physical and Theoretical Chemistry ,Acetonitrile ,Chromatography, High Pressure Liquid ,aquatic products ,Detection limit ,Chromatography ,high-performance liquid chromatography–tandem mass spectrometry ,Drug Residues ,chemistry ,Chemistry (miscellaneous) ,Linear Models ,Molecular Medicine ,methylene blue ,Methylene blue ,disinfectant - Abstract
A sensitive and reliable method was developed to determine methylene blue (MB) and its metabolite residues, including azure A (AZA), azure B (AZB), and azure C (AZC) in aquatic products by HPLC–MS/MS. The samples were extracted by acetonitrile and cleaned up by alumina-neutral (ALN) cartridges. The analytes were separated on a Sunfire C18 column (150 mm × 2.1 mm, 5 µm). The method was validated according to the European criteria of Commission Decision 2002/657/CE. Good linearity between 1–500 µg/L was obtained with correlation coefficients (R2) greater than 0.99. The limit of quantification (LOQ) was 1.0 µg/kg. The average recoveries at three levels of each compound (1, 5, and 10 µg/kg) were demonstrated to be in the range of 71.8–97.5%, with relative standard deviations (RSDs) from 1.05% to 8.63%. This method was suitable for the detection of methylene blue and its metabolite residues in aquatic products.
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- 2021
19. A Novel Synthesis of 4-Acetoxyl 5(4H)-Oxazolones by Direct α-Oxidation of N-Benzoyl Amino-Acid Using Hypervalent Iodine
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Gang Wen, Wen-Xuan Zhang, and Song Wu
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oxidation ,hypervalent iodine ,4-acetoxyl 5(4H)-oxazolones ,N-benzoyl amino-acid ,online FTIR ,Organic chemistry ,QD241-441 - Abstract
We have developed a new method to prepare 4-acetoxy substituted 5(4H)-oxazolones by direct oxidation of N-benzoyl amino-acids using hypervalent iodine. The method is efficient, economical and easy to perform for the synthesis of quaternary substituted amino acid derivatives. We used online FTIR monitoring techniques to analyze the reaction, and gave a plausible reaction mechanism.
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- 2017
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20. Triterpenoids from Ainsliaea yunnanensis Franch. and Their Biological Activities
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Jinjie Li, Bo Zhang, Hailing Liu, Xuan Zhang, Xiaoya Shang, and Changqi Zhao
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Ainsliaea yunnanensis ,triterpenoids ,NMR ,structures ,activity ,Organic chemistry ,QD241-441 - Abstract
One new pentacyclic triterpenoid, 3β-carboxylicfilic-4(23)-ene (1), and three known pentacyclic triterpenoids, adian-5-en-3α-ol (2), fernenol (3), and fern-7-en-3β-ol (4) were isolated from the petroleum ether phase of the ethanolic extract of Ainsliaea yunnanensis Franch. Their structures were established by spectroscopic methods including 1-D and 2-D NMR, and MS experiments. Compounds 1, 2, 3, and 4 showed significant selective cytotoxicity against human acute monocytic leukemia cell line (THP-1) with IC50 values of 5.12 μM, 1.78 μM, 1.74 μM, and 1.75 μΜ, respectively. Compound 1 also showed an anti-inflammatory effect through the inhibition of the activity of NF-κB by blocking the nuclear translocation of p65.
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- 2016
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21. TTF1, in the Form of Nanoparticles, Inhibits Angiogenesis, Cell Migration and Cell Invasion In Vitro and In Vivo in Human Hepatoma through STAT3 Regulation
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Bin Xiao, Dongjing Lin, Xuan Zhang, Meilan Zhang, and Xuewu Zhang
- Subjects
angiogenesis ,cell invasion ,cell migration ,Flavone derivative (TTF1) ,hepatoma ,STAT3 ,Organic chemistry ,QD241-441 - Abstract
TTF1-NP (5,2′,4′-trihydroxy-6,7,5′-trimethoxyflavone nanoparticles), derived from the traditional Changbai Mountain medicinal plant Sorbaria sorbifolia (SS), has been showed its anti-cancer effect in various liver cancer cell types and tissues. The present study was designed to evaluate the antitumor mechanism of the TTF1-NP against HepG2 hepatoma cells and HepG2 cells-induced hepatocarcinoma (HCC) in nude mouse model. Here we demonstrated that TTF1-NP inhibits tube formation of HUVECs and HepG2 cell migration and invasion, and inhibits tumor growth in nude mice implanted with HepG2 cells through the downregulation of STAT3 protein and activation, along with VEGF, KDR, bFGF, MMP2 and MMP9 levels. We further revealed that TTF1-NP decreased the DNA-binding capacity of STAT3. Together our results provide a mechanism by which TTF1-NP suppresses cancer cell migration, invasion and angiogenesis through the action of STAT3 and suggests TTF1-NP as a potential therapy for hepatocellular cancer treatment.
- Published
- 2016
- Full Text
- View/download PDF
22. An Efficient Chemical Synthesis of Scutellarein: An in Vivo Metabolite of Scutellarin
- Author
-
Ze-Xi Dong, Nian-Guang Li, Peng-Xuan Zhang, Ting Gu, Wen-Yu Wu, and Zhi-Hao Shi
- Subjects
scutellarin ,scutellarein ,metabolite ,efficient ,synthesis ,Organic chemistry ,QD241-441 - Abstract
Scutellarein (2), which is an important in vivo metabolite of scutellarin (1), was synthesized from 3,4,5-trimethoxyphenol (3) in high yield in four steps. This strategy relies on acetylation, aldolization, cyclization and hydrolysis reactions, respectively.
- Published
- 2016
- Full Text
- View/download PDF
23. The Synthesis of the Metabolites of 2′,3′,5′-Tri-O-acetyl-N6-(3-hydroxyphenyl) Adenosine (WS070117)
- Author
-
Wen-Xuan Zhang, Hong-Na Wu, Bo Li, Hong-Lin Wu, Dong-Mei Wang, and Song Wu
- Subjects
WS070117 ,metabolites ,synthesis ,Organic chemistry ,QD241-441 - Abstract
Seven metabolites of 2′,3′,5′-tri-O-acetyl-N6-(3-hydroxyphenyl) adenosine (WS070117) were synthesized by deacetylation, hydrolysis, cyclization, sulfonylation and glycosylation reactions, respectively. All these compounds, which could be useful as material standards for metabolic research, were characterized by NMR and HPLC-MS (ESI) analyses.
- Published
- 2015
- Full Text
- View/download PDF
24. A New and Efficient Synthesis of 6-O-Methylscutellarein, the Major Metabolite of the Natural Medicine Scutellarin
- Author
-
Zhi-Hao Shi, Wei Zhang, Shao-Peng Yu, Jian-Ping Yang, Ting Gu, Peng-Xuan Zhang, Wen-Yu Wu, Ze-Xi Dong, Yuping Tang, and Nian-Guang Li
- Subjects
Methyl Ethers ,synthesis ,Metabolite ,metabolite ,Pharmaceutical Science ,Glucuronates ,Ether ,Methylation ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Drug Discovery ,Humans ,Organic chemistry ,Apigenin ,Physical and Theoretical Chemistry ,Natural medicine ,Biotransformation ,scutellarein ,Scutellarin ,Scutellarein ,Communication ,Organic Chemistry ,scutellarin ,Flavones ,6-O-methylscutellarein ,Solutions ,chemistry ,Chemistry (miscellaneous) ,Yield (chemistry) ,Molecular Medicine ,Chloromethyl methyl ether - Abstract
In this paper, a new and efficient synthesis of 6-O-methylscutellarein (3), the major metabolite of the natural medicine scutellarin, is reported. Two hydroxyl groups at C-4' and C-7 in 2 were selectively protected by chloromethyl methyl ether after the reaction conditions were optimized, then 6-O-methyl-scutellarein (3) was produced in high yield after methylation of the hydroxyl group at C-6 and subsequent deprotection of the two methyl ether groups.
- Published
- 2015
25. Phenolic Composition, Antioxidant Properties, and Inhibition toward Digestive Enzymes with Molecular Docking Analysis of Different Fractions from Prinsepia utilis Royle Fruits
- Author
-
Yanli Ma, Yijia Jia, Xuan Zhang, Shengbao Cai, and Gui-Guang Cheng
- Subjects
Antioxidant ,DPPH ,medicine.medical_treatment ,α-glucosidase inhibitor ,Pharmaceutical Science ,Antioxidants ,Analytical Chemistry ,Rutin ,chemistry.chemical_compound ,Drug Discovery ,oxidative stress ,chemistry.chemical_classification ,ABTS ,biology ,Hep G2 Cells ,04 agricultural and veterinary sciences ,040401 food science ,Molecular Docking Simulation ,Biochemistry ,Chemistry (miscellaneous) ,Molecular Medicine ,UHPLC-ESI-HRMS/MS ,Composition (visual arts) ,Article ,lcsh:QD241-441 ,0404 agricultural biotechnology ,lcsh:Organic chemistry ,Phenols ,Picrates ,medicine ,Humans ,Benzothiazoles ,Physical and Theoretical Chemistry ,hydrogen bond ,Reactive oxygen species ,Plant Extracts ,Biphenyl Compounds ,Organic Chemistry ,alpha-Glucosidases ,Hydrogen Peroxide ,Lipase ,pancreatic lipase inhibition ,Enzyme Activation ,Enzyme ,chemistry ,Fruit ,Digestive enzyme ,biology.protein ,Sulfonic Acids ,Reactive Oxygen Species ,phenolic composition - Abstract
The present study investigated the phenolic profiles and antioxidant properties of different fractions from Prinsepia utilis Royle fruits using molecular docking analysis to delineate their inhibition toward digestive enzymes. A total of 20 phenolics was identified and quantified. Rutin, quercetin-3-O-glucoside, and isorhamnetin-3-O-rutinoside were the major phenolic compounds in the total phenolic fraction and flavonoid-rich fraction. The anthocyanin-rich fraction mainly contained cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside. All of the fractions exhibited strong radical scavenging activities and good inhibition on cellular reactive oxygen species (ROS) generation in H2O2-induced HepG2 cells, as evaluated by DPPH and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays. Moreover, the powerful inhibitory effects of those fractions against pancreatic lipase and α-glucosidase were observed. The major phenolic compounds that were found in the three fractions also showed good digestive enzyme inhibitory activities in a dose-dependent manner. Molecular docking analysis revealed the underlying inhibition mechanisms of those phenolic standards against digestive enzymes, and the theoretical analysis data were consistent with the experimental results.
- Published
- 2018
26. The Design and Synthesis of a New Class of RTK/HDAC Dual-Targeted Inhibitors
- Author
-
Jia Li, Xuan Zhang, Wei Lu, Yi Chen, and Mingbo Su
- Subjects
dual inhibitor ,Receptor, ErbB-2 ,Pharmaceutical Science ,Drug resistance ,Pharmacology ,Receptor tyrosine kinase ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,Inhibitory Concentration 50 ,synergistic effect ,lcsh:Organic chemistry ,Drug Discovery ,Quinazoline ,Humans ,Epidermal growth factor receptor ,Physical and Theoretical Chemistry ,Receptor ,Protein Kinase Inhibitors ,antitumor ,biology ,receptor tyrosine kinases ,Organic Chemistry ,fungi ,Receptor Protein-Tyrosine Kinases ,In vitro ,ErbB Receptors ,Histone Deacetylase Inhibitors ,Histone ,chemistry ,Chemistry (miscellaneous) ,Drug Design ,histone deacetylase ,biology.protein ,Molecular Medicine ,Histone deacetylase - Abstract
Over the years, the development of targeted medicines has made significant achievements. As a typical example, receptor tyrosine kinases (RTK) inhibitors have become important chemotherapy drugs for a variety of cancers. However, the effectiveness of these agents is always hindered by poor response rates and acquired drug resistance. In order to overcome these limitations, several dual-targeted inhibitors with quinazoline core were designed and synthesized. Though these compounds can simultaneously inhibit histone deacetylases (HDAC) as well as RTK, the structure-activity relationship (SAR) is still not clear enough. To further explore this type of dual-targeted inhibitors, a new class of quinazoline derivatives were designed and synthesized. Their activity evaluations include in vitro inhibitory activity of HDAC, epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2). The SAR study indicated that the introduction of polar group such as hydroxamate on the 4-position of the quinazoline core is more likely to provide a potent HDACi/HER2i hybrid rather than HDACi/EGFRi molecule.
- Published
- 2013
27. Potent Anti-HIV Activities and Mechanisms of Action of a Pine Cone Extract from Pinus yunnanensis
- Author
-
Guang-Ming Liu, Yong-Jun Lv, Yong-Tang Zheng, Ya-Juan Liu, Hao-Zhi Li, Xuan Zhang, Liu-Meng Yang, and Chang-Bo Zheng
- Subjects
Pinus yunnanensis ,Receptors, CXCR4 ,fusion ,Anti-HIV Agents ,Pharmaceutical Science ,HIV Integrase ,Microbial Sensitivity Tests ,Biology ,Inhibitory postsynaptic potential ,Article ,Cell Line ,Analytical Chemistry ,reverse transcriptase ,Drug Discovery ,Humans ,MTT assay ,Physical and Theoretical Chemistry ,pine cone ,EC50 ,Cytopathic effect ,Cell Nucleus ,Plant Extracts ,anti-HIV activity ,Organic Chemistry ,virus diseases ,Virus Internalization ,Pinus ,biology.organism_classification ,Virology ,Molecular biology ,Chemokine CXCL12 ,HIV Reverse Transcriptase ,Reverse transcriptase ,Protein Transport ,Cytolysis ,Chemistry (miscellaneous) ,HIV-1 ,Molecular Medicine ,Conifer cone - Abstract
The anti-HIV activities of a pine cone extract (YNS-PY-F) from Pinus yunnanensis have been evaluated, and its mechanisms of action were also explored. The pine cone extract, YNS-PY-F, potently inhibited HIV-1(IIIB), HIV-1(RF), HIV-1(A17), HIV-1(AO18) and HIV-2(ROD) and induced cytopathic effect in C8166 cells with EC₅₀ values of 0.96 μg/mL, 1.53 μg/mL, 0.88 μg/mL, 7.20 μg/mL and 6.17 μg/mL, respectively. The quantification of a p24 production assay showed that YNS-PY-F significantly inhibited the acute replication of HIV-1(IIIB), HIV-1RF, HIV-1(A17) and HIV-1(AO18) in C8166 cells. An MTT assay showed that YNS-PY-F also significantly inhibited the HIV-1(IIIB) induced cytolysis in MT-4 cells with an EC₅₀ value of 2.22 μg/mL. The mechanism assays showed that YNS-PY-F had potent inhibitory effects on the fusion between infected cells and uninfected cells, and the activity of HIV-1 reverse transcriptase, with EC₅₀ values of 7.60 μg/mL and 4.60 μg/mL, respectively. Overall, these data suggest that the pine cone extract from Pinus yunnanensis has potent inhibitory activities against HIV-1(IIIB), HIV-1(RF), RT inhibitor-resistant strains HIV-1(A17) and HIV-1(AO18), and HIV-2(ROD), and its anti-HIV mechanisms include inhibition of HIV entry and inhibition of reverse transcriptase activity.
- Published
- 2012
28. Compound K Induces Endoplasmic Reticulum Stress and Apoptosis in Human Liver Cancer Cells by Regulating STAT3
- Author
-
Wenjun Jiao, Yan Yan, Xuewu Zhang, Xuan Zhang, Qitong Sun, and Silin Zhang
- Subjects
0301 basic medicine ,Ginsenosides ,Pharmaceutical Science ,Analytical Chemistry ,STAT3 ,Mice ,chemistry.chemical_compound ,0302 clinical medicine ,Drug Discovery ,Endoplasmic Reticulum Chaperone BiP ,Mice, Inbred BALB C ,biology ,Chemistry ,Liver Neoplasms ,apoptosis ,Hep G2 Cells ,hepatoma ,Endoplasmic Reticulum Stress ,Neoplasm Proteins ,CK ,Chemistry (miscellaneous) ,030220 oncology & carcinogenesis ,Molecular Medicine ,Protopanaxadiol ,Female ,ERS ,Liver cancer ,STAT3 Transcription Factor ,Carcinoma, Hepatocellular ,Mice, Nude ,ginsenoside ,Article ,lcsh:QD241-441 ,03 medical and health sciences ,lcsh:Organic chemistry ,medicine ,Animals ,Humans ,Gene silencing ,Physical and Theoretical Chemistry ,Endoplasmic reticulum ,Organic Chemistry ,medicine.disease ,Xenograft Model Antitumor Assays ,030104 developmental biology ,Apoptosis ,Cancer cell ,Cancer research ,Unfolded protein response ,biology.protein - Abstract
The ginsenoside compound K (20-O-&beta, d-glucopyranosyl-20(S)-protopanaxadiol, CK) is an intestinal bacterial metabolite of ginseng protopanaxadiol saponin that has been reported to induce apoptosis in many cancer cells, however, the precise mechanisms of its activity in human hepatocellular carcinoma (HCC) cells remain unclear. Herein, we demonstrated that CK inhibited the growth and colony formation of HepG2 and SMMC-7721 cells, phenotypes that were mediated by inducing apoptosis. Meanwhile, CK showed lower toxicity in normal hepatoma cells. After treating HepG2 and SMMC-7721 cells with CK, p-STAT3 levels decreased, the three branches of the unfolded protein response were activated, and levels of endoplasmic reticulum stress (ERS)-related proteins were increased. We also revealed that CK decreased the DNA-binding capacity of STAT3. Moreover, silencing STAT3 with CRISPR/Cas9 technology enhanced CK-induced ERS and apoptosis. Finally, we showed that CK inhibited the growth of liver cancer xenografts with little toxicity. Mice bearing human HCC xenografts that were treated with CK showed increased GRP78 expression and decreased p-STAT3 levels. Taken together, these data showed that CK induced ERS and apoptosis by inhibiting p-STAT3 in human liver cancer cells, thus, CK might be a potential therapeutic candidate for human HCC.
- Published
- 2018
29. Evaluation of a Triple-Helical Peptide with Quenched Fluorophores for Optical Imaging of MMP-2 and MMP-9 Proteolytic Activity
- Author
-
W. B. Edwards, Jamee Bresee, Gregg B. Fields, Philip P. Cheney, Manishabrata Bhowmick, Baogang Xu, Xuan Zhang, and Mare Cudic
- Subjects
Gelatinases ,medicine.medical_treatment ,Proteolysis ,Pharmaceutical Science ,Peptide ,Matrix metalloproteinase ,Article ,Fluorescence ,Analytical Chemistry ,lcsh:QD241-441 ,03 medical and health sciences ,optical imaging ,0302 clinical medicine ,lcsh:Organic chemistry ,In vivo ,Cell Line, Tumor ,Drug Discovery ,medicine ,Gelatinase ,Humans ,Tomography, Optical ,fluorescence molecular tomography (FMT) ,Physical and Theoretical Chemistry ,030304 developmental biology ,Fluorescent Dyes ,chemistry.chemical_classification ,0303 health sciences ,matrix metalloproteinase-2 (MMP-2) ,Protease ,Microscopy, Confocal ,medicine.diagnostic_test ,Chemistry ,Organic Chemistry ,gelatinase ,triple-helical peptides ,Fluoresceins ,Molecular biology ,3. Good health ,Matrix Metalloproteinase 9 ,Microscopy, Fluorescence ,Chemistry (miscellaneous) ,Tumor progression ,030220 oncology & carcinogenesis ,MCF-7 Cells ,Molecular Medicine ,Matrix Metalloproteinase 2 ,Peptides ,MMP-9 ,Collagen Type V - Abstract
Matrix metalloproteinases (MMP) 2 and 9, the gelatinases, have consistently been associated with tumor progression. The development of gelatinase-specific probes will be critical for identifying in vivo gelatinoic activity to understand the molecular role of the gelatinases in tumor development. Recently, a self-assembling homotrimeric triple-helical peptide (THP), incorporating a sequence from type V collagen, with high substrate specificity to the gelatinases has been developed. To determine whether this THP would be suitable for imaging protease activity, 5-carboxyfluorescein (5FAM) was conjugated, resulting in 5FAM3-THP and 5FAM6-THP, which were quenched up to 50%. 5FAM6-THP hydrolysis by MMP-2 and MMP-9 displayed kcat/KM values of 1.5 × 104 and 5.4 × 103 M−1 s−1, respectively. Additionally 5FAM6-THP visualized gelatinase activity in gelatinase positive HT-1080 cells, but not in gelatinase negative MCF-7 cells. Furthermore, the fluorescence in the HT-1080 cells was greatly attenuated by the addition of a MMP-2 and MMP-9 inhibitor, SB-3CT, indicating that the observed fluorescence release was mediated by gelatinase proteolysis and not non-specific proteolysis of the THPs. These results demonstrate that THPs fully substituted with fluorophores maintain their substrate specificity to the gelatinases in human cancer cells and may be useful in in vivo molecular imaging of gelatinase activity.
- Published
- 2014
- Full Text
- View/download PDF
30. Synthesis of the Key Intermediate of Coenzyme Q10
- Author
-
Fan-Song Mu, Xuan Zhang, Ping Yu, Yuangang Zu, Yu-Jie Fu, and Meng Luo
- Subjects
p-toluenesulfonyl chloride ,(2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene ,Pharmaceutical Science ,Alkylation ,Chloride ,Coupling reaction ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,Hydrolysis ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Bromide ,Drug Discovery ,medicine ,Organic chemistry ,Physical and Theoretical Chemistry ,Isoprene ,Coenzyme Q10 ,2,3,4,5-tetramethoxytoluene ,Organic Chemistry ,chemistry ,Chemistry (miscellaneous) ,Yield (chemistry) ,Molecular Medicine ,isoprene ,medicine.drug - Abstract
(2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p-toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p-toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation to compound 3, followed by the addition of 2,3,4,5-tetramethoxytoluene (TeMT), assembled the two parts into compound 4. The key parameters of each reaction were optimized at the same time, and the four total operations needed to produced compound 4 had a 27.9% overall yield under the optimized conditions. The structures of the compounds were characterized by 1H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process.
- Published
- 2011
- Full Text
- View/download PDF
31. The Synthesis of the Metabolites of 2',3',5'-Tri-O-acetyl-N6-(3-hydroxyphenyl) Adenosine (WS070117).
- Author
-
Wen-Xuan Zhang, Hong-Na Wu, Bo Li, Hong-Lin Wu, Dong-Mei Wang, and Song Wu
- Subjects
- *
METABOLITES , *CHEMICAL synthesis , *DEACETYLATION , *HYDROLYSIS , *RING formation (Chemistry) - Abstract
Seven metabolites of 2',3',5'-tri-O-acetyl-N6-(3-hydroxyphenyl) adenosine (WS070117) were synthesized by deacetylation, hydrolysis, cyclization, sulfonylation and glycosylation reactions, respectively. All these compounds, which could be useful as material standards for metabolic research, were characterized by NMR and HPLC-MS (ESI) analyses. [ABSTRACT FROM AUTHOR]
- Published
- 2016
- Full Text
- View/download PDF
32. The Design and Synthesis of a New Class of RTK/HDAC Dual-Targeted Inhibitors.
- Author
-
Xuan Zhang, Mingbo Su, Yi Chen, Jia Li, and Wei Lu
- Subjects
- *
PROTEIN-tyrosine kinase inhibitors , *HISTONE deacetylase inhibitors , *ANTINEOPLASTIC agents , *CHEMICAL inhibitors , *DRUG therapy , *HER2 protein , *EPIDERMAL growth factor receptors - Abstract
Over the years, the development of targeted medicines has made significant achievements. As a typical example, receptor tyrosine kinases (RTK) inhibitors have become important chemotherapy drugs for a variety of cancers. However, the effectiveness of these agents is always hindered by poor response rates and acquired drug resistance. In order to overcome these limitations, several dual-targeted inhibitors with quinazoline core were designed and synthesized. Though these compounds can simultaneously inhibit histone deacetylases (HDAC) as well as RTK, the structure-activity relationship (SAR) is still not clear enough. To further explore this type of dual-targeted inhibitors, a new class of quinazoline derivatives were designed and synthesized. Their activity evaluations include in vitro inhibitory activity of HDAC, epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2). The SAR study indicated that the introduction of polar group such as hydroxamate on the 4-position of the quinazoline core is more likely to provide a potent HDACi/HER2i hybrid rather than HDACi/EGFRi molecule. [ABSTRACT FROM AUTHOR]
- Published
- 2013
- Full Text
- View/download PDF
33. Potent Anti-HIV Activities and Mechanisms of Action of a Pine Cone Extract from Pinus yunnanensis.
- Author
-
Xuan Zhang, Liu-Meng Yang, Guang-Ming Liu, Ya-Juan Liu, Chang-Bo Zheng, Yong-Jun Lv, Hao-Zhi Li, and Yong-Tang Zheng
- Subjects
- *
HIV infections , *THERAPEUTICS , *PINE cones , *CELL lines , *CELLULAR pathology , *REVERSE transcriptase - Abstract
The anti-HIV activities of a pine cone extract (YNS-PY-F) from Pinus yunnanensis have been evaluated, and its mechanisms of action were also explored. The pine cone extract, YNS-PY-F, potently inhibited HIV-1IIIB, HIV-1RF, HIV-1A17, HIV-1AO18 and HIV-2ROD and induced cytopathic effect in C8166 cells with EC50 values of 0.96 μg/mL, 1.53 μg/mL, 0.88 μg/mL, 7.20 μg/mL and 6.17 μg/mL, respectively. The quantification of a p24 production assay showed that YNS-PY-F significantly inhibited the acute replication of HIV-1IIIB, HIV-1RF, HIV-1A17 and HIV-1AO18 in C8166 cells. An MTT assay showed that YNS-PY-F also significantly inhibited the HIV-1IIIB induced cytolysis in MT-4 cells with an EC50 value of 2.22 μg/mL. The mechanism assays showed that YNS-PY-F had potent inhibitory effects on the fusion between infected cells and uninfected cells, and the activity of HIV-1 reverse transcriptase, with EC50 values of 7.60 μg/mL and 4.60 μg/mL, respectively. Overall, these data suggest that the pine cone extract from Pinus yunnanensis has potent inhibitory activities against HIV-1IIIB, HIV-1RF, RT inhibitor-resistant strains HIV-1A17 and HIV-1AO18, and HIV-2ROD, and its anti-HIV mechanisms include inhibition of HIV entry and inhibition of reverse transcriptase activity. [ABSTRACT FROM AUTHOR]
- Published
- 2012
- Full Text
- View/download PDF
34. Synthesis of the Key Intermediate of Coenzyme Q10.
- Author
-
Fan-Song Mu, Meng Luo, Yu-Jie Fu, Xuan Zhang, Ping Yu, and Yuan-Gang Zu
- Subjects
CHEMICAL reactions ,COENZYMES ,ISOPRENE ,NUCLEAR magnetic resonance ,MASS spectrometry - Abstract
(2'E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p-toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p-toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation to compound 3, followed by the addition of 2,3,4,5-tetramethoxytoluene (TeMT), assembled the two parts into compound 4. The key parameters of each reaction were optimized at the same time, and the four total operations needed to produced compound 4 had a 27.9% overall yield under the optimized conditions. The structures of the compounds were characterized by
1 H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process. [ABSTRACT FROM AUTHOR]- Published
- 2011
- Full Text
- View/download PDF
35. Efficient Lewis Acid Ionic Liquid-Catalyzed Synthesis of the Key Intermediate of Coenzyme Q10 under Microwave Irradiation.
- Author
-
Yue Chen, Yuangang Zu, Yujie Fu, Xuan Zhang, Ping Yu, Guoyong Sun, and Efferth, Thomas
- Subjects
LEWIS acids ,FRIEDEL-Crafts reaction ,IONIC liquids ,COENZYMES ,ACETYLCOENZYME A ,IRRADIATION - Abstract
An efficient synthesis of a valuable intermediate of coenzyme Q
10 by microwave-assisted Lewis acidic ionic liquid (IL)-catalyzed Friedel-Crafts alkylation is reported. The acidity of six [Etpy]BF4-based ionic liquids was characterized by means of the FT-IR technique using acetonitrile as a molecular probe. The catalytic activities of these ionic liquids were correlated with their Lewis acidity. With increasing Lewis acid strength of the ionic liquids, their catalytic activity in the Friedel-Crafts reaction increased, except for [Etpy]BF4 -AlCl3 . The effects of the reaction system, the molar fraction of Lewis acid in the Lewis acid ILs and heating techniques were also investigated. Among the six Lewis acid ionic liquids tested [Etpy]BF4 -ZnCl2 showed the best catalytic activity, with a yield of 89% after a very short reaction time (150 seconds). This procedure has the advantages of higher efficiency, better reusability of ILs, energy conservation and ecofriendliness. The method has practical value for preparation of CoQ10 on an industrial scale. [ABSTRACT FROM AUTHOR]- Published
- 2010
- Full Text
- View/download PDF
36. Synthesis of the Key Intermediate of Coenzyme Q10.
- Author
-
Fan-Song Mu, Meng Luo, Yu-Jie Fu, Xuan Zhang, Ping Yu, and Yuan-Gang Zu
- Subjects
- *
CHEMICAL reactions , *COENZYMES , *ISOPRENE , *NUCLEAR magnetic resonance , *MASS spectrometry - Abstract
(2'E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p-toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p-toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation to compound 3, followed by the addition of 2,3,4,5-tetramethoxytoluene (TeMT), assembled the two parts into compound 4. The key parameters of each reaction were optimized at the same time, and the four total operations needed to produced compound 4 had a 27.9% overall yield under the optimized conditions. The structures of the compounds were characterized by 1H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process. [ABSTRACT FROM AUTHOR]
- Published
- 2011
- Full Text
- View/download PDF
Catalog
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