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Accueil > Les équipes > Glycochimie Organique Biologique et Supramoléculaire (GOBS) > Publications

Publications

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2017


  • P. a Zhang, C. Tugny, J. Meijide Suárez, M. Guitet, E. Derat, N. Vanthuyne, Y. M. Zhang, O. Bistri, V. Mouries-Mansuy, M. Ménand, S. Roland, L. Fensterbank, et M. Sollogoub, « Artificial chiral metallo-pockets including a single metal serving as both structural probe and catalytic center », Chem, vol. 3, nᵒ 1, p. 174-191.
    Mots-clés : GOBS, MACO, POLE 3, POLE1.


  • P. a Zhang, J. Meijide Suárez, T. Driant, E. Derat, Y. Zhang, M. Ménand, S. Roland, et M. Sollogoub, « Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration », Angewandte Chemie International Edition, vol. 56, nᵒ 36, p. 10821-10825.


  • B. Doistau, L. Benda, J. - L. Cantin, L. - M. Chamoreau, E. Ruiz, V. Marvaud, B. Hasenknopf, et G. Vives, « Six states switching of redox-active molecular tweezers by three orthogonal stimuli », Journal of the American Chemical Society.
    Résumé : A six level molecular switch based on terpyridine(Ni-salphen)2 tweezers and addressable by three orthogonal stimuli (metal coordination, redox reaction and guest binding) is reported. By a metal coordination stimulus, the tweezers can be mechanically switched from an open “W”-shaped conformation to a closed “U”-shaped form. Theses two states can each be reversibly oxidized by the redox stimulus and bind to a pyrazine guest resulting in four additional states. All six states are stable and accessible by the right combination of stimuli and were studied by NMR, XRD, EPR spectroscopy and DFT calculations. The combination of the supramolecular concepts of mechanical motion and guest binding with the redox non-innocent and valence tautomerism properties of Ni-salphen complexes added two new dimensions to a mechanical switch.
    Mots-clés : E-POM, GOBS, POLE 2, POLE 3.


  • J. W. Fredy, J. Scelle, G. Ramniceanu, B. - T. Doan, C. S. Bonnet, É. Tóth, M. Ménand, M. Sollogoub, G. Vives, et B. Hasenknopf, « Mechanostereoselective One-Pot Synthesis of Functionalized Head-to-Head Cyclodextrin [3]Rotaxanes and Their Application as Magnetic Resonance Imaging Contrast Agents », Organic Letters, vol. 19, nᵒ 5, p. 1136-1139.
    Mots-clés : GOBS.
    Note Note
    <p>doi: 10.1021/acs.orglett.7b00153</p>


  • J. Malinge, B. Géraudie, P. Savel, V. Nataf, A. Prignon, C. Provost, Y. Zhang, P. Ou, K. Kerrou, J. - N. Talbot, J. - M. Siaugue, M. Sollogoub, et C. Ménager, « Liposomes for PET and MR Imaging and for Dual Targeting (Magnetic Field/Glucose Moiety): Synthesis, Properties, and in Vivo Studies », Molecular Pharmaceutics, vol. 14, nᵒ 2, p. 406-414.
    Résumé : We describe the potentiality of a new liposomal formulation enabling positron emission tomography (PET) and magnetic resonance MR imaging. The bimodality is achieved by coupling a 68Ga-based radiotracer on the bilayer of magnetic liposomes. In order to enhance the targeting properties obtained under a permanent magnetic field, a sugar moiety was added in the lipid formulation. Two new phospholipids were synthesized, one with a specific chelator of 68Ga (DSPE-PEG-NODAGA) and one with a glucose moiety (DSPE-PEG-glucose). The liposomes were produced according to a fast and safe process, with a high radiolabeling yield. MR and PET imaging were performed on mice bearing human glioblastoma tumors (U87MG) after iv injection. The accumulation of the liposomes in solid tumor is evidenced by MR imaging and the amount is evaluated in vivo and ex vivo according to PET imaging. An efficient magnetic targeting is achieved with these new magnetic liposomes.
    Mots-clés : GOBS, POLE 3.


  • C. K. O'Sullivan, M. Ortiz, A. , M. Debela, M. Svobodova, S. Thorimbert, D. Lesage, R. Cole, et B. Hasenknopf, « PCR Incorporation of Polyoxometalate Modified Deoxynucleotide Triphosphates and Their Application in Molecular Electrochemical Sensing of Yersinia pestis », Chemistry – A European Journal, vol. 23, nᵒ 44, p. 10597–10603.
    Résumé : Redox-labeled nucleotides are of increasing interest for the fabrication of next generation molecular tools and should meet requirements of being thermally stable, sensitive, and compatible with polymerase-mediated incorporation whilst also being electrochemically discriminable. The synthesis and characterization of Keggin and Dawson polyoxometalate-deoxynucleotide (POM-dNTP) bioconjugates linked through 7-deaza-modified purines is described. The modified POM-dNTPs were used for polymerase based amplification of a DNA sequence specific for Yersinia pestis and the amplified DNA detected via an electrochemical DNA sensor. This highlights the potential of polyoxometalates as thermally stable, sensitive and polymerase-compatible redox labels for exploitation in bioanalytical applications.
    Mots-clés : Biosensor, CHEMBIO, CSOB, Electroanalytical Chemistry, GOBS, Labelled nucleotides, PCR, POLE 3, Polyoxometalates.
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  • M. Petricevic, L. F. Sobala, P. Z. Fernandes, L. Raich, A. J. Thompson, G. Bernardo-Seisdedos, O. Millet, S. Zhu, M. Sollogoub, J. Jiménez-Barbero, C. Rovira, G. J. Davies, et S. J. Williams, « Contribution of Shape and Charge to the Inhibition of a Family GH99 endo-α-1,2-Mannanase », Journal of the American Chemical Society, vol. 139, nᵒ 3, p. 1089-1097.
    Résumé : Inhibitor design incorporating features of the reaction coordinate and transition-state structure has emerged as a powerful approach for the development of enzyme inhibitors. Such inhibitors find use as mechanistic probes, chemical biology tools, and therapeutics. Endo-α-1,2-mannosidases and endo-α-1,2-mannanases, members of glycoside hydrolase family 99 (GH99), are interesting targets for inhibitor development as they play key roles in N-glycan maturation and microbiotal yeast mannan degradation, respectively. These enzymes are proposed to act via a 1,2-anhydrosugar “epoxide” mechanism that proceeds through an unusual conformational itinerary. Here, we explore how shape and charge contribute to binding of diverse inhibitors of these enzymes. We report the synthesis of neutral dideoxy, glucal and cyclohexenyl disaccharide inhibitors, their binding to GH99 endo-α-1,2-mannanases, and their structural analysis by X-ray crystallography. Quantum mechanical calculations of the free energy landscapes reveal how the neutral inhibitors provide shape but not charge mimicry of the proposed intermediate and transition state structures. Building upon the knowledge of shape and charge contributions to inhibition of family GH99 enzymes, we design and synthesize α-Man-1,3-noeuromycin, which is revealed to be the most potent inhibitor (KD 13 nM for Bacteroides xylanisolvens GH99 enzyme) of these enzymes yet reported. This work reveals how shape and charge mimicry of transition state features can enable the rational design of potent inhibitors.
    Mots-clés : GOBS, POLE 3.


  • Y. Teng, X. Li, K. Yang, X. Li, Z. Zhang, L. Wang, Z. Deng, B. Song, Z. Yan, Y. Zhang, K. Lu, et P. Yu, « Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers », European Journal of Medicinal Chemistry, vol. 125, p. 335-345.
    Résumé : Four ring-closed analogs of natural prenylated chalcone desmethylxanthohumol (1) and their dimers were synthesized from the commercially available 1-(2,4,6-trihydroxyphenyl)ethan-1-one in five and six linear steps, respectively. The structures of the eight new derivatives were confirmed using1H NMR, 13C NMR and HRMS. The antioxidant activity of the new chalcone derivatives were evaluated in a PC12 cell model of H2O2-induced oxidative damage. The SAR studies suggested that the catechol motif was essential for the antioxidant activity. Moreover, the dimers showed better antioxidant activity than their corresponding monomers did. Among them, compound 14d was the most potent and increased PC12 cell viability from 25% to 85%. Flow cytometric analysis showed that compound 14d, the most potent compound, decreased the apoptotic PC12 cell percentage and significantly reduced the LDH release and 8-OHdG generation but increased the GSH levels in H2O2-treated PC12 cells. Furthermore, compound 14d had a higher FRAP value than that of gallic acid. It also reduced the stable ABTS+ free radical with a lower EC50 than that of gallic acid.
    Mots-clés : Antioxidant, Chalcone, Desmethylxanthohumol, Dimer, GOBS, POLE 3, Synthesis.


  • S. Wu, L. Yang, W. Sun, L. Si, S. Xiao, Q. Wang, L. Dechoux, S. Thorimbert, M. Sollogoub, D. Zhou, et Y. Zhang, « Design, synthesis and biological evaluation of gentiopicroside derivatives as potential antiviral inhibitors », European Journal of Medicinal Chemistry, vol. 130, p. 308-319.
    Résumé : Based on classical drug design theory, a novel series of gentiopicroside derivatives was designed and synthesized. All synthesized compounds were then biologically evaluated for their inhibition of influenza virus and anti-HCV activity in vitro. Some of the gentiopicroside derivatives, such as 11a, 13d and 16 showed interesting anti-influenza virus activity with IC50 at 39.5 μM, 45.2 μM and 44.0 μM, respectively. However, no significant anti-HCV activity was found for all of gentiopicroside derivatives. The preliminary results indicate that modification of the sugar moiety on gentiopicroside was helpful for enhancing the anti-influenza activities. Our works demonstrate the importance of secoiridoid natural products as new leads in the development of potential antiviral inhibitors.
    Mots-clés : Anti-influenza virus, antiviral agents, CHEMBIO, Gentiopicroside derivatives, GOBS, Natural product, POLE 3, Secoiridoid.


  • S. Wu, N. Yaoyao, Y. Zhao, W. Sun, S. Thorimbert, L. Dechoux, M. Sollogoub, et Y. Zhang, « Research Progress of Natural Product Gentiopicroside - a Secoiridoid Compound », Mini-Reviews in Medicinal Chemistry, vol. 17, nᵒ 1, p. 62-77.
    Résumé : Gentiopicroside is a secoiridoid compound isolated from Gentiana lutea which is called Qin Jiao in Chinese. It is one of the most common herbal medicines used in China. In this article, we review the pharmacological and biological activity (antiviral, anti-inflammatory, analgesia, antihepatotoxic and choleretic), as well as biotransformation of the gentiopicroside. In addition, attempt towards the total synthesis of gentiopicroside is also presented.
    Mots-clés : Biological activity, biotransformation, CHEMBIO, gentiopicroside, GOBS, natural product, POLE 3, secoiridoid, total synthesis..


  • N. Yu, Z. - Y. Zhu, Y. Liu, J. - Y. Zhang, et Y. - M. Zhang, « Chromatographic analysis and preparation of l-arabinose from corncob by acid hydrolysis », Industrial Crops and Products, vol. 95, p. 163-169.
    Résumé : l-arabinose, a kind of rare sugar, which has already become newly developed functional saccharide with many beneficial biomedical and health effects. In this study, we carried out several experiments to analyze the component of hydrolyzed corncob. Components in the hydrolysate were detected by the methods of ultraviolet spectrogram, HPLC, TLC and High-efficient Thin Layer scanning analysis. The hydrolysis temperature, holding time, concentration of oxalic acid and solid-liquid ratio were investigated as objects by single factor experiments. The results showed that the content of saccharides in the hydrolysate of corncob was up to 72.70%. Three kinds of monosaccharide (d-xylose, l-arabinose, d-glucose) were detected by HPLC analysis and the relative amount of the above three saccharides were 32.8%, 31.4% and 35.7%, respectively. The optimum conditions were: temperature 90 °C, holding time 5 h, concentration of oxalic acid 6%, solid-liquid ratio 1:12, and the highest l-arabinose yield was 14.89%.
    Mots-clés : Acid hydrolysis, Corncob, GOBS, l-arabinose, POLE 3, Yield.


  • X. Zhu, A. Quaranta, R. Bensasson, M. Sollogoub, et Y. Zhang, « Secondary-rim γ-cyclodextrin functionalization to conjugate with C60: improved efficacy as photosensitizer », Chemistry A European Journal, p. n/a-n/a.
    Résumé : DIBAL-H-mediated demethylation provides a novel entry to secondary rim functionalized γ-CD. 2A,3B-dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows the access to the most water-soluble C60 conjugate described so far. The water-solubility 0.12 M (550 mg/mL) is 150 times higher than that of native γ-CD/ C60 complex. Its singlet oxygen (¹O₂) quantum yield is 0.39, an increase by one or two orders of magnitude compared to that of α(β)CD-C60 conjugates.
    Mots-clés : gamma-CD * secondary rim * C60 * aggregation * photosensitizer, GOBS, POLE 3.
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2016



  • M. a Ménand, M. Sollogoub, B. Boitrel, et S. Le Gac, « Hexaphyrin–Cyclodextrin Hybrids: A Nest for Switchable Aromaticity, Asymmetric Confinement, and Isomorphic Fluxionality », Angewandte Chemie International Edition, vol. 55, nᵒ 1, p. 297-301.
    Résumé : Conformational control over the highly flexible π-conjugated system of expanded porphyrins is a key step toward the fundamental understanding of aromaticity and for the development of molecular electronics. We have synthesized unprecedented hexaphyrin–cyclodextrin (HCD) capped hybrids in which the hexaphyrin part is constrained in a planar rectangular conformation in either a 26 or a 28 π-electron oxidation state ([26]/[28]HCD). These structures display strong aromaticity and antiaromaticity, respectively, exhibit markedly different chiroptical properties, and are interconvertible upon the addition of DDQ or NaBH(OAc)3, thus affording a rare switchable aromatic–antiaromatic system with a free-base expanded porphyrin. Conformational analysis revealed discrimination of the two coordination sites of the hexaphyrin, one of which was coupled to a confined asymmetric environment, and fluxional behavior consisting of apparent rotation of the hexaphyrin cap through a shape-shifting mechanism.
    Mots-clés : aromaticity, conformation analysis, Cyclodextrins, degenerate equilibria, GOBS, POLE 3, porphyrinoids.
  • V. Calvez, A. G. Marcellin, L. Bouteiller, M. Menand, P. Evenou, A. Gothland, D. Colesnic, J. Rossignol, et M. Sollogoub, « Capped cyclodextrin-hydrophobic moiety conjugate, cyclodextrin supramolecular polymer, and cyclodextrin-siRNA complex and method of synthesis thereof », U.S. Patent PCT/ EP2016/070892.
    Mots-clés : GOBS, POLE 3, POLE 4, POLYMERES.


  • M. W. Cooke, M. - P. Santoni, B. Hasenknopf, et G. S. Hanan, « Heteroleptic ruthenium(II) chromophores based on tunable polytopic 4′-(benzamidinato)-2,2′:6′,2′′-terpyridines », Dalton Transactions, vol. 45, nᵒ 44, p. 17850-17858.
    Résumé : A modulable and simple approach towards heteroleptic ruthenium(II) complexes of amidine-based polypyridine ligands is presented. New complexes 1 and 2 ([(terpyridine)Ru(terpyridine-C6H4-C(NR)(NHR))]2+ with R = propyl and R = phenyl derivatives, respectively) were characterized by NMR spectroscopy in solution and by X-ray diffraction, which confirmed the obtention of the (E) stereoisomer alone. Depending on the bulkiness of the R-substituents introduced on the amidine moiety, rotational isomerism around the C–N bond could be observed at r.t. Spectroscopic and electrochemical studies showed that the nature of the R-substituents introduced on the amidine moiety can significantly influence the redox and ground-state acido-basic properties of the complexes, while maintaining their electronic features. This particular tunability of polytopic 4′-(amidinato)-terpyridines offers an interesting perspective for photoactive units in larger multi-functional arrays.
    Mots-clés : GOBS, POLE 3.


  • A. M. Debela, S. Thorimbert, B. Hasenknopf, C. K. O'Sullivan, et M. Ortiz, « Electrochemical primer extension for the detection of single nucleotide polymorphisms in the cardiomyopathy associated MYH7 gene », Chemical Communications, vol. 52, nᵒ 4, p. 757-759.
    Résumé : We report the labelling of dideoxy nucleotides (ddNTPs) for use in electrochemical array based primer extension for t

    he detection of single nucleotide polymorphisms (SNPs). The results confirm the extension of the immobilised primers for each of the four ddNTPs, representing a significant advance in achieving a cost-effective platform for screening of disease-specific SNPs.
    Mots-clés : CHEMBIO, GOBS, POLE 3.


  • L. Duarte, S. Nag, M. Castro, E. Zaborova, M. Ménand, M. Sollogoub, V. Bennevault, J. - F. Feller, et P. Guégan, « Chemical Sensors Based on New Polyamides Biobased on (Z) Octadec-9-Enedioic Acid and β-Cyclodextrin », Macromolecular Chemistry and Physics, vol. 217, nᵒ 14, p. 1620-1628.


  • S. L. Gac, B. Boitrel, M. Sollogoub, et M. Ménand, « Protonated hexaphyrin–cyclodextrin hybrids: molecular recognition tuned by a kinetic-to-thermodynamic topological adaptation », Chemical Communications, vol. 52, nᵒ 60, p. 9347-9350.
    Résumé : Protonation study of [26/28]hexaphyrin-capped cyclodextrins revealed a temperature controlled conformational transition of the cap. The hexaphyrin undergoes a rectangular-to-triangular shape-shifting which strongly modifies the shape of the confined environment featured by the hybrids, and ultimately affects the encapsulation of the counterions. It provides an attractive access to innovative allosteric host–guest systems.
    Mots-clés : GOBS, POLE 3.


  • Y. Gao, Z. Cao, C. Su, Z. Chen, X. He, F. Ding, H. Li, et Y. Zhang, « Chiron Approaches to the Antitumor Natural Product Fuzanin D », Synthesis, vol. 48, nᵒ 24, p. 4471-4476.
    Résumé : Thieme E-Books & E-Journals
    Mots-clés : GOBS, POLE 3.


  • Y. Gao, X. He, F. Ding, et Y. Zhang, « Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines », Synthesis, vol. 48, nᵒ 23, p. 4017-4037.
    Résumé : Thieme E-Books & E-Journals
    Mots-clés : GOBS, POLE 3.


  • X. Han, Y. Shi, L. Si, Z. Fan, H. Wang, R. Xu, P. Jiao, K. Meng, Z. Tian, X. Zhou, H. Jin, X. Wu, H. Chen, Y. Zhang, L. Zhang, S. Xiao, et D. Zhou, « Design, synthesis and biological activity evaluation of novel conjugated sialic acid and pentacyclic triterpene derivatives as anti-influenza entry inhibitors », MedChemCom, vol. 7, nᵒ 10, p. 1932-1945.
    Résumé : Influenza virus is a major human pathogen that causes annual epidemics and occasional pandemics. Recently, plant-derived pentacyclic triterpenes have been shown to act as highly potent anti-viral agents by efficiently preventing the attachment of the virion to the host cells. In this report, we conjugated sialic acid with oleanolic acid (OA), a natural product with broad antiviral entry activity, as well as three other analogs echinocystic acid (EA), ursolic acid (UA) and betulinic acid (BA). A total of 24 conjugated sialic acid and pentacyclic triterpene derivatives with different linkers were synthesized and evaluated for antiviral activity against influenza A/WSN/33 (H1N1) virus in MDCK cell culture. The most potent compound had an IC50 of 41.2 μM. Time-of-addition, hemagglutination inhibition (HI), surface plasmon resonance (SPR) and molecular docking assays demonstrated that compound 20a acted as an influenza virus entry inhibitor by preventing the binding of influenza virus hemagglutinin (HA) protein to host cells.
    Mots-clés : GOBS, POLE 3.

  • X. - C. Liu, Z. - Y. Zhu, Y. - L. Tang, M. -fei Wang, Z. Wang, A. - J. Liu, et Y. - M. Zhang, « Structural properties of polysaccharides from cultivated fruit bodies and mycelium of Cordyceps militaris », Carbohydrate Polymers, vol. 142, p. 63-72.
    Résumé : The structural properties of polysaccharides, respectively, obtained from the fermented mycelium and cultivated fruiting bodies of the Cordyceps militaris were investigated and compared in this paper. First, the crude polysaccharides were extracted from the mycelium and the fruiting bodies, respectively. The polysaccharides were successively purified by Sevag and chromatography on Sephadex G-100 column to produce two polysaccharides fractions termed CMPS-II and CBPS-II, respectively. The average molecular weights of CMPS-II and CBPS-II were 1.402×10(3) kDa and 1.273×10(3) kDa, respectively, and they were mainly composed of mannose, glucose and galactose in the mole ratios of 1:28.63:1.41 and 1:12.41:0.74, respectively, for CMPS-II and CBPS-II. Afterward, the structural features of CMPS-II and CBPS-II were investigated by a combination of chemical and instrumental analysis, such as FT-IR, periodate oxidation-Smith degradation, GC-MS, NMR and methylation analysis. The results indicated that structurally, both CMPS-II and CBPS-II were 1,3-branched-galactomannoglucan that had a linear backbone of (1→4)-linked α-D-glucopyranose (Glcp). Congo-red test revealed that CMPS-II and CBPS-II existed as triple-helical chains in 0.05-0.15 M NaOH solution.
    Mots-clés : Cordyceps militaris, GOBS, POLE 3, Polysaccharide, structure.


  • Z. Liu, Q. Zheng, W. Chen, S. Man, Y. Teng, X. Meng, Y. Zhang, P. Yu, et W. Gao, « Paris saponin I inhibits proliferation and promotes apoptosis through down-regulating AKT activity in human non-small-cell lung cancer cells and inhibiting ERK expression in human small-cell lung cancer cells », RCS Advances, vol. 6, nᵒ 75, p. 70816-70824.
    Résumé : Paris Saponin I (PSI), a steroidal saponin derivative extracted from a traditional Chinese herbal Paris polyphylla, has shown cytotoxic effects on several tumor cell lines. However, the mechanisms of its antitumor activity especially for lung cancers remain to be elucidated. In this present investigation, we continue to explore the efficacy and mechanisms underlying the cytotoxic effects of PSI in lung cancer cell lines. Three non-small cell lung cancer (NSCLC) cells (H1299, H520, H460) and one small cell lung cancer (SCLC) cell (H446) were treated with PSI for the first time. PSI significantly induced cell cycle arrest at the G2/M phase and mitochondrial-related apoptosis NSCLC cells but not SCLC cells. Additionally, PSI reduced phosphorylation of AKT in NSCLC and ERK in SCLC in general. Interestingly, we observed that PSI influenced different signaling pathways among the four kinds of lung cancer cells. After PSI treatment, p38 MAPK and ERK activation were observed in H1299, while p38 MAPK increased and JNK decreased in H520. On the contrary, we found JNK activation in H460 cells with PSI. However, PSI upregulated the AKT activity and inhibited the JNK expression in H446 cells. The results indicate that PSI exhibits the cytotoxicity in different pathways depending on the cancer types.
    Mots-clés : GOBS, POLE 3.


  • Y. Nie, M. Zhong, Z. Jiang, J. Sun, Y. Gao, F. Ding, H. Li, Y. Zhang, et X. He, « Synthesis and potential anticonvulsant activity of new aryl sulfonyl semicarbazide derivatives », Medicinal Chemistry Research, vol. 25, nᵒ 7, p. 1425-1432.
    Résumé : In the present study on the development of new anticonvulsants, twelve new aryl sulfonyl semicarbazide derivatives were synthesized and tested for anticonvulsant activity using maximal electroshock (MES), subcutaneous pentylenetetrazole screens. Their neurotoxicity was determined by the rotorod test. The most active compound 5i showed the MES-induced seizures with ED50 value of 7.3 mg/kg and TD50 value of 402.3 mg/kg after intraperitoneally injection to mice, which provided compound 5i with a protective index (TD50/ED50) of 55.1 in the MES test.
    Mots-clés : GOBS, POLE 3.


  • S. Roland, X. Ling, et M. - P. Pileni, « N-Heterocyclic Carbene Ligands for Au Nanocrystal Stabilization and Three-Dimensional Self-Assembly », Langmuir, vol. 32, nᵒ 31, p. 7683-7696.
    Résumé : N-Heterocyclic carbenes (NHCs) have emerged as a new class of ligands for materials chemistry that appears particularly relevant for the stabilization and functionalization of metal nanoparticles (NPs). The particular properties and high synthetic flexibility of NHCs make them highly attractive tools for the development of new (nano)materials and the fundamental study of their properties. The relationships between the NHC structure and NP structure/properties, including physical, biological, and self-assembly properties, remain largely unknown. In the past decade, many efforts have been made to gain more fundamental understanding in this area. In this feature article, we present our contribution in this field focusing on the formation of NHC-coated Au nanocrystals (NCs), their stability, and their ability to self-assemble into 3D crystalline structures called supracrystals. First, the formation of NHC-stabilized Au NCs is discussed by comparing different NHC structures, NHC-based Au precursors, and synthesis methods. This study shows the major role of the NHC structure in obtaining both stable NHC-coated Au NCs and narrow size distributions. In a second part, a comparative study of the oxygen resistance of NHC- and thiol-coated NCs is presented, demonstrating the enhanced stability of NHC-coated Au NCs to oxygen-based treatments. Finally, the self-assembly of NHC-coated Au NCs into 3D Au superlattices is presented. The formation of large organized domains of several micrometers is described from the design of NHCs tailored with long alkyl chains. In these different contexts, efforts have been made to gain a more in-depth understanding of the behavior of NHC ligands at the surface of NCs. These results show that the NHC-based approach to nanomaterials has many assets for opening a new research area in the supracrystal world.
    Mots-clés : GOBS, POLE 3.


  • Y. - O. Teng, H. - Y. Zhao, J. Wang, H. Liu, M. - L. Gao, Y. Zhou, K. - L. Han, Z. - C. Fan, Y. - M. Zhang, H. Sun, et P. Yu, « Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives », European Journal of Medicinal Chemistry, vol. 112, p. 145-156.
    Résumé : A series of novel di- or trisubstituted isatin derivatives were designed and synthesized in 5–6 steps in 25–45% overall yields. Their structures were confirmed by 1H NMR and 13C NMR as well as LC-MS. The anticancer activity of the fourty-three new isatin derivatives against human T lymphocyte cells Jurkat was evaluated by MTT assay in vitro. SAR study suggested that the combination of 1-benzyl and 5-[trans-2-(methoxycarbonyl)ethen-1-yl] substitution greatly enhanced their cytotoxic activity. Among them, compound 2h was shown to have a significant cytotoxic activity with an IC50 value of 0.03 μM, more than 330-fold higher than that of it's mother molecule isatin. Investigation of the cell morphology changes and annexin-V/PI staining study demonstrated that compound 2h inhibited the proliferation of Jurkat cells by inducing apoptosis. Since compound 2h induced the dissipation of mitochondrial membrane potential and the activation of caspase-3, it was obvious that compound 2h inhibited the proliferation of Jurkat cells through the mitochondrial apoptotic pathway. Other than this, compound 2h exerted inhibition effect to many other tumor cells and only showed weak cytotoxic to human normal cells suggesting that compound 2h possessed a broad range of anticancer spectrum and high safety to normal cells.
    Mots-clés : Anti-tumor agents, Apoptosis, GOBS, Isatin derivatives, Jurkat cells, POLE 3, proliferation.

  • H. Wang, R. Xu, Y. Shi, L. Si, P. Jiao, Z. Fan, X. Han, X. Wu, X. Zhou, F. Yu, Y. Zhang, L. Zhang, L. Zhang, D. Zhou, et S. Xiao, « Design, synthesis and biological evaluation of novel L-ascorbic acid-conjugated pentacyclic triterpene derivatives as potential influenza virus entry inhibitors », European Journal of Medicinal Chemistry, vol. 110, p. 376-388.
    Résumé : Since the influenza viruses can rapidly evolve, it is urgently required to develop novel anti-influenza agents possessing a novel mechanism of action. In our previous study, two pentacyclic triterpene derivatives (Q8 and Y3) have been found to have anti-influenza virus entry activities. Keeping the potential synergy of biological activity of pentacyclic triterpenes and l-ascorbic acid in mind, we synthesized a series of novel l-ascorbic acid-conjugated pentacyclic triterpene derivatives (18-26, 29-31, 35-40 and 42-43). Moreover, we evaluated these novel compounds for their anti-influenza activities against A/WSN/33 virus in MDCK cells. Among all evaluated compounds, the 2,3-O,O-dibenzyl-6-deoxy-l-ascorbic acid-betulinic acid conjugate (30) showed the most significant anti-influenza activity with an EC50 of 8.7 μM, and no cytotoxic effects on MDCK cells were observed. Time-of-addition assay indicated that compound 30 acted at an early stage of the influenza life cycle. Further analyses revealed that influenza virus-induced hemagglutination of chicken red blood cells was inhibited by treatment of compound 30, and the interaction between the influenza hemagglutinin (HA) and compound 30 was determined by surface plasmon resonance (SPR) with a dissociation constant of KD = 3.76 μM. Finally, silico docking studies indicated that compound 30 and its derivative 31 were able to occupy the binding pocket of HA for sialic acid receptor. Collectively, these results suggested that l-ascorbic acid-conjugated pentacyclic triterpenes were promising anti-influenza entry inhibitors, and HA protein associated with viral entry was a promising drug target.
    Mots-clés : Animals, antiviral agents, Ascorbic Acid, Dogs, Drug design, Entry inhibitor, GOBS, Hemagglutinin, Hemagglutinin Glycoproteins, Influenza Virus, humans, Influenza A Virus, H1N1 Subtype, Influenza virus, Influenza, Human, l-ascorbic acid, Madin Darby Canine Kidney Cells, Molecular Docking Simulation, Orthomyxoviridae Infections, Pentacyclic triterpene, pentacyclic triterpenes, POLE 3, Sialic acid receptor, Virus Internalization.

  • H. Wang, Y. Cui, R. Zou, Z. Cheng, W. Yao, Y. Mao, et Y. Zhang, « Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor », Carbohydrate Research, vol. 427, p. 1-5.
    Résumé : Trimethylsilyl (TMS) protecting group has been found to be very useful for the simultaneous protection of both the glycosyl donor- and the acceptor-substrates in oligosaccharide synthesis. Thus, while the per-O-trimethylsilylated glycosyl iodides served as the glycosyl donor, those bearing selectively exposed primary hydroxyl groups were found suitable as the glycosyl acceptor for the reaction. The cheap and commercially available trialkylamine, triethylamine was found to be an effective promoter for the glycosylation. Importantly, the reaction was α-stereospecific and gave the products in 58%-78% yields.
    Mots-clés : Glycosyl iodide, GOBS, POLE 3, triethylamine, Trimethylsilyl group, α-Glycosylation.

  • X. - T. Wang, Z. - Y. Zhu, L. Zhao, H. - Q. Sun, M. Meng, J. - Y. Zhang, et Y. - M. Zhang, « Structural characterization and inhibition on α-d-glucosidase activity of non-starch polysaccharides from Fagopyrum tartaricum », Carbohydrate Polymers, vol. 153, p. 679-685.
    Résumé : In the present study, the crude polysaccharide was extracted from Fagopyrum tartaricum and purified by Sephadex G-25 and G-75 column to produce a polysaccharide fraction termed TBP-II. Its average molecular weight was 26kDa. The structural characterization of TBP-II was investigated by gas chromatography, periodate oxidation-Smith degradation, Methylation and NMR. Congo red was applied to explore its advanced structures. The results revealed that chemical composition and structural characteristic of TBP-II was mainly consisted of galactose, arabinose, xylose and glucose with a molar ratio of 0.7:1:6.3:74.2. The backbone of TBP-II was composed of (1→4)-linked α-d-glucopyranosyl (Glcp), while the branches comprised of (1→3)-linked α-d-glucopyranosyl (Glcp), (1→6)-linked α-d-galactopyranosyl (Galp) and (1→2,4)-linked α-d-rhamnopyranosyl (Rhap). The structure of TBP-II was 1,3 and 1,6-branched-galactorhamnoglucan that had a linear backbone of (1→4)-linked α-d-glucopyranose (Glcp). Using Congo red assay showed that it was absent of triple helix structure. The α-d-glucosidase inhibitory activity of TBP-II was determined using acarbose as positive control. The result showed that the inhibition rate depended on the concentration of polysaccharides.
    Mots-clés : Acetic acid (PubChem CID: 176), Butanol (PubChem CID: 263), Characterization, Chloroform (PubChem CID: 6212), Dimethyl sulfoxide (PubChem CID: 679), Ethanol (PubChem CID: 702), Fagopyrum tartaricum, GOBS, POLE 3, Polysaccharide, Sodium hydroxide (PubChem CID:14798), Trifluoroacetic acid(PubChem CID: 6422), α-d-glucosidase.

  • S. Xiao, L. Si, Z. Tian, P. Jiao, Z. Fan, K. Meng, X. Zhou, H. Wang, R. Xu, X. Han, G. Fu, Y. Zhang, L. Zhang, et D. Zhou, « Pentacyclic triterpenes grafted on CD cores to interfere with influenza virus entry: A dramatic multivalent effect », Biomaterials, vol. 78, p. 74-85.
    Résumé : Multivalent effect plays an important role in biological processes, particularly in the specific recognition of virus with its host cell during the first step of infection. Here we report the synthesis of multivalent pentacyclic triterpene grafted on cyclodextrin core and potency of against influenza entry activity. Nine star-shaped compounds containing six, seven and eight pentacyclic triterpene pharmacophore on cyclodextrin scaffold were prepared by way of copper-catalyzed azide-alkyl cycloaddition reaction under microwave activation. Some of the multimers exhibited much potent antiviral activity against H1N1 virus (A/WSN/33), even equivalent or superior to oseltamivir. The most active compound 31, a heptavalent oleanolic acid-β-cyclodextrin conjugate, shows an up to 125-fold potency enhancement by its IC50 value over the corresponding monovalent conjugate and oleanolic acid, disclosing a clear multivalent effect. Further studies show that three compounds 31-33 exhibited broad spectrum inhibitory activity against other two human influenza A/JX/312 (H3N2) and A/HN/1222 (H3N2) viruses with the IC50 values at 2.47-14.90 μM. Most importantly, we found that compound 31, one of the best representative conjugate, binds tightly to the viral envelope hemagglutinin with a dissociation constant of KD = 2.08 μM, disrupting the interaction of hemagglutinin with the sialic acid receptor and thus the attachment of viruses to host cells. Our study might establish a strategy for the design of new pharmaceutical agents based on multivalency so as to block influenza virus entry into host cells.
    Mots-clés : Animals, Dogs, Entry inhibitor, GOBS, Hemagglutinin, Influenza A Virus, H1N1 Subtype, Influenza virus, Madin Darby Canine Kidney Cells, Membrane Fusion, Multivalent effect, Pentacyclic triterpene, POLE 3, Triterpenes.


  • S. Xiao, Q. Wang, L. Si, X. Zhou, Y. Zhang, L. Zhang, et D. Zhou, « Synthesis and biological evaluation of novel pentacyclic triterpene α-cyclodextrin conjugates as HCV entry inhibitors », European Journal of Medicinal Chemistry, vol. 124, p. 1-9.
    Résumé : Hepatitis C virus (HCV) entry is a key target for the treatment of chronic HCV infection. In our continuing efforts to identify novel potential anti-HCV entry inhibitors, a series of water-soluble triazole-bridged α-cyclodextrin-pentacyclic triterpene conjugates were easily synthesized with moderate to good yields. These novel compounds were fully identified and characterized by 1D and 2D NMR spectroscopy and ESI-HRMS. The anti-HCV entry activities were determined based on HCVpp/VSVGpp entry assays. The best results were found for compounds 15 and 18, which displayed the most promising anti-HCV entry activities with average IC50 values of 1.18 μM and 0.25 μM, respectively. In addition, the in vitro cytotoxicity activity of the two compounds against MDCK cells showed no toxicity at 100 μM. Five different binding assays were set up to identify the action mechanism. The results showed that the compounds exert their inhibitory activity at the post-binding step and subsequently prevent virus entry.
    Mots-clés : click chemistry, GOBS, HCV entry inhibitor, Pentacyclic triterpene, POLE 3, α-Cyclodextrin.

  • Y. Yang, J. He, Y. Suo, L. Lv, J. Wang, C. Huo, Z. Zheng, Z. Wang, J. Li, W. Sun, et Y. Zhang, « Anti-inflammatory effect of taurocholate on TNBS-induced ulcerative colitis in mice », Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, vol. 81, p. 424-430.
    Résumé : Taurocholate is a natural conjugated bile acid. The aim of this study was to evaluate the anti-inflammatory effect of taurocholate in TNBS-induced ulcerative colitis in mice. The colitis were induced by rectal administration of TNBS. After 24h, the experimental animals were treated with sulfasalazine (SASP, 500mg/kg/day) and taurocholate (20, 40 and 60mg/kg) for 7 consecutive days. The anti-inflammatory effects of taurocholate for colitis were assessed by body weight, colonic weight and length, macroscopic scores, and histopathological examinations. In addition, the colonic tissue levels of myeloperoxidase (MPO) activity, interleukin (IL)-1β, interferon (IFN-γ) and tumour necrosis factor-α (TNF-α) were also determined to assess the effect of taurocholate. Compared with the model group, treatment with taurocholate (20, 40 and 60mg/kg) significantly inhibited the body weight loss, improved colonic weight and length, and decreased macroscopic and histopathological scores. Furthermore, the activity accumulation of MPO and the colonic tissue levels of IL-1β, IFN-γ and TNF-α were also decreased by administration of taurocholate. All the findings of this study suggested that taurocholate has the anti-inflammatory effect in ulcerative colitis in mice and indicated it as a good candidate to treat inflammatory bowel disease.
    Mots-clés : Anti-inflammatory effect, Cytokines, GOBS, POLE 3, Taurocholate, TNBS, Ulcerative colitis.

  • Y. Yang, J. He, Y. Suo, Z. Zheng, J. Wang, L. Lv, C. Huo, Z. Wang, J. Li, W. Sun, et Y. Zhang, « Tauroursodeoxycholate improves 2,4,6-trinitrobenzenesulfonic acid-induced experimental acute ulcerative colitis in mice », International Immunopharmacology, vol. 36, p. 271-276.
    Résumé : Ulcerative colitis is a chronic nonspecific inflammatory disease of unknown cause. The aim of this study was to evaluate the anti-inflammatory effect of tauroursodeoxycholate in 2, 4, 6-trinitrobenzenesulfonic acid-induced experimental colitis in mice. After the induction of colitis for 24h, the mice were administrated orally with tauroursodeoxycholate (20, 40 and 60mg/kg) and sulfasalazine (500mg/kg) by gavage for 7 consecutive days. The inhibition effects were evaluated by the body of weight change, survival rate, macroscopical and histological evaluations. Besides, myeloperoxidase (MPO) activity, interleukin (IL)-1β, interferon (IFN)-γ and tumour necrosis factor-α (TNF-α) in colon tissue were also determined by enzyme-linked immunosorbent assay. Treatment with different doses of tauroursodeoxycholate (20, 40 and 60mg/kg) significantly improved the body weight change, decreased the macroscopic and histopathological scores. Compared with the model group, the accumulation of MPO activity, the colonic tissue levels of IL-1β, IFN-γ and TNF-α were significantly reduced in the tauroursodeoxycholate treated groups. Moreover, tauroursodeoxycholate assuaged the symptoms of colitis. These results suggested that tauroursodeoxycholate has an anti-inflammatory effect in TNBS-induced ulcerative colitis in mice.
    Mots-clés : Cytokines, GOBS, POLE 3, Tauroursodeoxycholate, Trinitrobenzenesulfonic acid, Ulcerative colitis.

  • Y. Zhang, D. Lu, M. Sollogoub, et Y. Zhang, « Carbohydrate–carbohydrate interaction: from hypothesis to confirmation », in Carbohydrate Chemistry, p. 238-254.
    Résumé : Carbohydrates play important roles in a wide range of biological processes. Since the first hypothesis about carbohydrate–carbohydrate interaction (CCI) was proposed by Hakomori et al., an increasing interest has been placed on CCI, using a variety of techniques. Based on all these studies, Lewisx–Lewisx interaction (a typical CCI) has been now confirmed to be specific, homotypic, and mediated by the presence of divalent cations such as Ca2+. In this review, a detailed overview of the process from hypothesis to confirmation of carbohydrate–carbohydrate interaction is summarized.
    Mots-clés : GOBS, POLE 3.

  • Y. Zhou, H. - Y. Zhao, D. Jiang, L. - Y. Wang, C. Xiang, S. - P. Wen, Z. - C. Fan, Y. - M. Zhang, N. Guo, Y. - O. Teng, et P. Yu, « Low toxic and high soluble camptothecin derivative 2-47 effectively induces apoptosis of tumor cells in vitro », Biochemical and Biophysical Research Communications, vol. 472, nᵒ 3, p. 477-481.
    Résumé : The cytotoxic activity of camptothecin derivatives is so high that these compounds need to be further modified before their successful application as anti-cancer agents clinically. In this study, we reported the synthesis and biological evaluation of a novel camptothecin derivative called compound 2-47. The changes in structure did not reduce its activity to inhibit DNA topoisomerase I. Compound 2-47 induced apoptosis of many tumor cells including leukemia cells K562, Jurkat, HL-60, breast cancer cell BT-549, colon cancer cell HT-29 and liver cancer cell HepG2 with a half maximal inhibitory concentration (IC50) of 2- to 3-fold lower than HCPT as a control. In particular, 2-47 inhibited the proliferation of Jurkat cells with an IC50 of as low as 40 nM. By making use of Jurkat cell as a model, following treatment of Jurkat cells, compound 2-47 activated caspase-3 and PARP, resulting in a decreased Bcl-2/Bax ratio. These data showed that compound 2-47 induces Jurkat cell death through the mitochondrial apoptotic pathway. In addition, compound 2-47 showed a decreased cytotoxic activity against normal cells and an improved solubility in low-polar solvent. For example, compound 2-47 solutes in CHCl3 130-fold higher than HCPT. Taken together, our data demonstrated that camptothecin derivative 2-47 notably inhibits the tumor cell proliferation through mitochondrial-mediated apoptosis in vitro.
    Mots-clés : Apoptosis, camptothecin, Camptothecin derivatives, Cell Line, Tumor, DNA topoisomerase I, Dose-Response Relationship, Drug, Drug design, GOBS, humans, Neoplasms, Experimental, POLE 3, Solubility, Treatment Outcome.

  • X. Zhu, M. Sollogoub, et Y. Zhang, « Biological applications of hydrophilic C60 derivatives (hC60s)- a structural perspective », European Journal of Medicinal Chemistry, vol. 115, p. 438-452.
    Résumé : Reactive oxygen species (ROS) generation and radical scavenging are dual properties of hydrophilic C60 derivatives (hC60s). hC60s eliminate radicals in dark, while they produce reactive oxygen species (ROS) in the presence of irradiation and oxygen. Compared to the pristine C60 suspension, the aqueous solution of hC60s is easier to handle in vivo. hC60s are diverse and could be placed into two general categories: covalently modified C60 derivatives and pristine C60 solubilized non-covalently by macromolecules. In order to present in detail, the above categories are broken down into 8 parts: C60(OH)n, C60 with carboxylic acid, C60 with quaternary ammonium salts, C60 with peptide, C60 containing sugar, C60 modified covalently or non-covalently solubilized by cyclodextrins (CDs), pristine C60 delivered by liposomes, functionalized C60-polymer and pristine C60 solubilized by polymer. Each hC60 shows the propensity to be ROS producer or radical scavenger. This preference is dependent on hC60s structures. For example, major application of C60(OH)n is radical scavenger, while pristine C60/γ-CD complex usually serves as ROS producer. In addition, the electron acceptability and innate hydrophobic surface confer hC60s with O2 uptake inhibition, HIV inhibition and membrane permeability. In this review, we summarize the preparation methods and biological applications of hC60s according to the structures.
    Mots-clés : Biological applications, GOBS, Hydrophilic C(60) derivatives, POLE 3, Radical scavenger, ROS generation.

  • Z. - Y. Zhu, D. Cui, H. Gao, F. - Y. Dong, X. -cui Liu, F. Liu, L. Chen, et Y. -min Zhang, « Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides », European Journal of Medicinal Chemistry, vol. 114, p. 8-13.
    Résumé : Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-derived oligosaccharides: one is 3-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,3-glycosidic bound, the other is 1-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,1-glycosidic bound, which were accomplished in seven steps from d-fructose and β-d-galactose and every step of yield above 75%. This synthetic route provided a practical and effective synthetic strategy for galactooligosaccharides, starting from commercially available monosaccharides. Then we evaluated on their prebiotic properties in the search for potential agents of regulating and improving the intestinal flora of human. The result showed that the prebiotic properties of Lactulose-derived oligosaccharides was much better than Lactulose. Among them, 3-O-β-d-galactopyranosyl-d-fructose displayed the most potent activity of proliferation of L. acidophilus.
    Mots-clés : GOBS, Lactobacillus acidophilus, Lactulose, Lactulose-derived oligosaccharides, POLE 3, Prebiotics.

  • Z. - Y. Zhu, F. Dong, X. Liu, Q. Lv, Y. Yang, F. Liu, L. Chen, T. Wang, Z. Wang, et Y. Zhang, « Effects of extraction methods on the yield, chemical structure and anti-tumor activity of polysaccharides from Cordyceps gunnii mycelia », Carbohydrate Polymers, vol. 140, p. 461-471.
    Résumé : This study was to investigate the effects of different extraction methods on the yield, chemical structure and antitumor activity of polysaccharides from Cordyceps gunnii (C. gunnii) mycelia. Five extraction methods were used to extract crude polysaccharides (CPS), which include room-temperature water extraction (RWE), hot-water extraction (HWE), microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE) and cellulase-assisted extraction (CAE). Then Sephadex G-100 was used for purification of CPS. As a result, the antitumor activities of CPS and PPS on S180 cells were evaluated. Five CPS and purified polysaccharides (PPS) were obtained. The yield of CPS by microwave-assisted extraction (CPSMAE) was the highest and its anti-tumor activity was the best and its macromolecular polysaccharide (3000-1000kDa) ratio was the largest. The PPS had the same monosaccharide composition, but their obvious difference was in the antitumor activity and the physicochemical characteristics, such as intrinsic viscosity, specific rotation, scanning electron microscopy and circular dichroism spectra.
    Mots-clés : Acetic acid (PubChem CID: 176), Acetic anhydride (PubChem CID: 7918), Antitumor activity, Cellulase (PubChem CID: 3084041), Chemical structure, Chloroform (PubChem CID: 6212), Cordyceps gunnii, Dimethylsulfoxide (PubChem CID: 21912085), Ethanol (PubChem CID: 702), Extraction method, GOBS, Methanol (PubChem CID: 887), N-butyl alcohol (PubChem CID: 263), POLE 3, Polysaccharide, Pyridine (PubChem CID: 1049), Trifluoroacetic acid (PubChem CID: 6422).


  • Z. - Y. Zhu, M. - Z. Guo, F. Liu, Y. Luo, L. Chen, M. Meng, X. - T. Wang, et Y. - M. Zhang, « Preparation and inhibition on α-d-glucosidase of low molecular weight polysaccharide from Cordyceps militaris », International Journal of Biological Macromolecules, vol. 93, Part A, p. 27-33.
    Résumé : The structural properties and the inhibition on α-d-glucosidase activity of the low molecular weight (LCMPs-II) obtained from the optimized acid hydrolysis of the Cordyceps militaris polysaccharides (CMPs) were investigated in this paper. The LCMPs-II with a molecular weight of 28 KDa mainly composed of rhamnose, xylose and glucose with the molar ratio of 1: 2.19: 6.73 was separated from LCMPs-I which was the acid hydrolysis product of CMPs by chromatography on Sephadex G-100 column. The solubility of LCMPs-II was tested to be 32.12 ± 1.05 g in 100 mL distilled water under 25 °C. Its solubility was almost as twice as that of CMPs. Afterward, the structural features of LCMPs-II was investigated by a combination of chemical and instrumental analysis such as the specific rotation determination, FT-IR, periodate oxidation-Smith degradation, Congo-red, GC, scanning electron microscope and NMR. The results showed that the optical rotation of LCMPs-II was +25° and it was 1,3-branched-rhamnoxyloglucan which had a linear backbone of (1 → 4)-linked α-d-glucopyranose (α-d-Glcp units).
    Mots-clés : Acid hydrolysis, Cordyceps militaris, GOBS, Inhibitory activity, POLE 3.
  • Z. - Y. Zhu, Y. Li, H. - Q. Sun, L. - J. Chen, Y. - L. Tang, X. - C. Liu, et Y. - M. Zhang, « Screening of Cordyceps Strains and Optimization of Its Solid-State Fermentation Conditions on Bioconversion of Astragalus Residue », Cellulose Chemistry and Technology, vol. 50, nᵒ 2, p. 257-263.
    Résumé : The Astragalus residue is produced after the extraction of Astragalus polysaccharides (APS). In Astragalus residue, the main ingredient is crude fiber. The crude fiber is considered to be the main source for green chemicals, bio-fuels and bio-based products. In this study, we used five kinds of Cordyceps as fermentation strains and Astragalus residue as fermentation substrate for solid-state fermentation. Crude fiber degradation rate after fermentation was considered as the main indicator. The mannitol content and soluble sugar content of the fermentation product were used as secondary indicators. The experiments were carried out by screening the solid-state fermentation strains, optimizing the solid-state fermentation conditions and studying the pilot-scale cultivation of solid-state fermentation. From the results of screening the solid-state fermentation strains, we selected the Paecilomyces bainier strain for further investigation. The fermentation conditions were optimized with four single factors, including fermentation time, solid fermentation inoculum size, pH value of solid medium and fermentation substrate thickness. The single-factor tests revealed that the optimum conditions were the following: fermentation time of 25 days, fermentation substrate pH of the initial value, inoculum of 20% and fermentation substrate thickness of 1.0 cm.
    Mots-clés : Astragalus residue, Cordyceps Paecilomyces sinensis, GOBS, POLE 3, solid-state fermentation.


  • Z. - Y. Zhu, F. Liu, H. Gao, H. Sun, M. Meng, et Y. - M. Zhang, « Synthesis, characterization and antioxidant activity of selenium polysaccharide from Cordyceps militaris », International Journal of Biological Macromolecules, vol. 93, Part A, p. 1090-1099.
    Résumé : A purified selenium-containing derivatives of Cordyceps militaris polysaccharide synthesized using H2SeO3/HNO3 and BaCl2 as a catalyst was investigated in this paper. The reaction condition was optimized by selecting different reaction temperature and period. Afterward, the one with the highest Se content was purified by ultra-filtration device with a molecular cut off size of 10KDa. Followed by its structural characterizations. Results of IFR and 13C NMR spectroscopy indicated that C-6 substitution was predominant in selenized polysaccharide. The modified polysaccharide with molecular weight of 1998 KDa was mainly consisted of mannose, glucose and galactose in the mole ratios of with the mole ratios of 1:28.63:1.41. Thermogravimetric and morphological analyses of the samples were carried out by AFS, SEM and AFM. In addition, the in vitro antioxidant results suggested that selenium-containing polysaccharide should be applied as a novel selenium source in dietary supplements, with potent antioxidant properties.
    Mots-clés : Cordyceps militaris, GOBS, POLE 3, polysaccharides, Selenize, structure.

  • Z. - Y. Zhu, X. - C. Liu, F. - Y. Dong, M. - Z. Guo, X. - T. Wang, Z. Wang, et Y. - M. Zhang, « Influence of fermentation conditions on polysaccharide production and the activities of enzymes involved in the polysaccharide synthesis of Cordyceps militaris », Applied Microbiology and Biotechnology, vol. 100, nᵒ 9, p. 3909-3921.
    Résumé : The influence of different fermentation conditions on intracellular polysaccharide (IPS) production and activities of the phosphoglucomutase (PGM), UDPG-pyrophosphorylase (UGP), phosphoglucose isomerase (PGI), UDPG-dehydrogenase (UGD), and glucokinase (GK) implicated in metabolite synthesis in Cordyceps militaris was evaluated. The highest IPS production (327.57 ± 6.27 mg/100 mL) was obtained when the strain was grown in the optimal medium containing glucose (40 g · L(-1)), beef extract (10 g · L(-1)), and CaCO3 (0.5 g · L(-1)), and the initial pH and temperature were 7 and 25 °C, respectively. The activities of PGM, UGP, and PGI were proved to be influenced by the fermentation conditions. A strong correlation between the activities of these enzymes and the production of IPS was found. The transcription level of the pgm gene (encoding PGM) was 1.049 times and 1.467 times compared to the ugp gene and pgi gene (encoding UGP and PGI), respectively, in the optimal culture medium. This result indicated that PGM might be the highly key enzyme to regulate the biosynthesis of IPS of C. militaris in a liquid-submerged culture. Our study might be helpful for further research on the pathway of polysaccharide biosynthesis aimed to improve the IPS production of C. militaris.
    Mots-clés : biosynthesis, Cordyceps militaris, Enzyme activity, GOBS, Intracellular polysaccharides, POLE 3.

  • Z. - Y. Zhu, X. - C. Liu, X. - N. Fang, H. - Q. Sun, X. - Y. Yang, et Y. - M. Zhang, « Structural characterization and anti-tumor activity of polysaccharide produced by Hirs

    utella sinensis », International Journal of Biological Macromolecules, vol. 82, p. 959-966.
    Résumé : HSP-III, a novel homogeneous polysaccharide with 513.89 kDa molecular weight, was fractionated from submerged cultures of Hirsutella sinensis by Sevag and chromatography on Sephadex G-100 column. The total sugar content of HSP-III was amounted to 89.87%. Based on the results of high performance gel permeation chromatogram (HPGPC), FT-IR, NMR spectroscopy, GC, periodate oxidation-smith degradation and methylation analysis, it showed that HSP-III was mainly composed of mannose and galactose, and a small amount of rhamnose, arabinose, xylose, and glucose. The molar ratio of Rha:Ara:Xyl:Man:Glu:Gal was 1.00:2.44:13.11:74.13:13.80:54.39. The main chain of HSP-III was majorly composed of (1→3) glucose. The tumor inhibition ratio on H22 cell was 79.04% at 100 μg/mL of HSP-III.
    Mots-clés : Anti-tumor activity, Antineoplastic Agents, Ascomycota, Cell Line, Tumor, Cell Survival, Fungal Polysaccharides, GOBS, humans, Magnetic Resonance Spectroscopy, Methylation, Molecular Weight, Periodic Acid, POLE 3, Polysaccharide, Spectroscopy, Fourier Transform Infrared, structure, Structure-Activity Relationship.


  • Z. - Y. Zhu, Y. Luo, G. - L. Dong, Y. - Y. Ren, L. - J. Chen, M. - Z. Guo, X. - T. Wang, X. - Y. Yang, et Y. Zhang, « Effects of the ultra-high pressure on structure and α-glucosidase inhibition of polysaccharide from Astragalus », International Journal of Biological Macromolecules, vol. 87, p. 570-576.
    Résumé : A novel homogeneous polysaccharide fraction (APS) was extracted from Astragalus by hot water and purified by Sephadex G-100 and G-75 column. Its molecular weight was 693 kDa. APS and APS with...
    Mots-clés : GOBS, POLE 3.


  • Z. - Y. Zhu, Y. Luo, Y. Liu, X. - T. Wang, F. Liu, M. - Z. Guo, Z. Wang, A. - J. Liu, et Y. - M. Zhang, « Inclusion of chrysin in β-cyclodextrin and its biological activities », Journal of Drug Delivery Science and Technology, vol. 31, p. 176-186.
    Résumé : Chrysin is a plant flavone that possesses some significant biological activities. β-Cyclodextrin (β-CD) due to its property of encapsulating molecules that are hydrophobic in nature is widely applied as drug delivery vehicle. The paper presents the preparation, characterization and properties of chrysin-β-cyclodextrin inclusion complex. The stoichiometry of the inclusion complex has been established to be 1:3 (chrysin to β-cyclodextrin), with the inclusion rate of 90.5 ± 2.63 at 55 °C. The process of inclusion not only increased the solubility of chrysin but also its antioxidant potential, antimicrobial activity and anti-tumor activity.
    Mots-clés : Biological activities, Chrysin, GOBS, inclusion complex, POLE 3, Water solubility, β-Cyclodextrin.

  • Z. - Y. Zhu, M. Meng, H. Sun, Y. Li, Y. - Y. Ren, et Y. Zhang, « Immunostimulatory activity of glycopeptides from Paecilomyces sinensis under normal and cyclophosphamide induced immunosuppressive conditions in mice models », Food & Function, vol. 7, nᵒ 8, p. 3566-3576.
    Résumé : The present study was designed to evaluate immune-modulating effects of the glycopeptide from Paecilomyces sinensis (CPS-II) by using mouse peritoneal macrophage and cytoxan (CTX) induced immunosuppression models. Our results from phagocytotic and mononuclear phagocytic system function assays showed that CPS-II stimulated phagocytosis of the phagocytes. A splenocyte proliferation assay showed that CPS-II acted to combine Concanavalin A (ConA) or lipopolysaccharides (LPS) in splenocyte proliferation. The results demonstrated that CPS-II increased the indices of the thymus and spleen. Hematological and histopathological analysis revealed the protective effect of CPS-II against CTX induced immunosuppression. CPS-II also significantly increased the expression of CD4(+) and CD8(+) splenic T lymphocytes, which were suppressed by CTX in peripheral blood. The expressions of serum cytokines related to immune function, including TNF-α, IL-6, and IFN-γ, were up-regulated in a dose-dependent manner. The expression of the transcription factor NF-κB in the spleen was enhanced after CPS-II-treatment. In conclusion, our results indicated that CPS-II was involved in immunostimulatory actions leading to its modulatory effects on immunosuppression, and one possible mechanism of action was to activate NF-κB.
    Mots-clés : GOBS, POLE 3.

  • Z. - Y. Zhu, M. Meng, H. Sun, Y. Li, N. Yu, et Y. - M. Zhang, « Structural analysis and immunostimulatory activity of glycopeptides from Paecilomyces sinensis », Food & Function, vol. 7, nᵒ 3, p. 1593-1600.
    Résumé : The parasitic fungus, Paecilomyces sinensis, is used to produce Cordyceps materials as a succedaneum of natural Cordyceps sinensis (C. sinensis) in China. In this work, a glycopeptide (CPS-II) was isolated and purified from Paecilomyces sinensis. The result of HPLC indicated that CPS-II was a glycopeptide. The estimated average molecular weight of CPS-II was 2 × 10(6) Da. FTIR, methylation, periodate oxidation, Smith degradation, (1)H NMR, (13)C NMR and CD were used for its structural analysis. The glycopeptide CPS-II was mainly composed of (1 → 3), (1 → 4) connected glucose and galactose as the backbone, there are (1 → 2,3,6) connected glucose, (1 → 3,6) connected mannose, and (1 → 6) connected galactose. Cell proliferation assay and morphological observations indicated that in a certain range of concentrations and time, CPS-II can significantly improve the proliferation activity of RAW264.7 cells.
    Mots-clés : GOBS, POLE 3.


  • Z. - Y. Zhu, Z. -qian Wang, F. Liu, X. - C. Liu, L. - J. Chen, X. - R. Ge, A. - J. Liu, et Y. - M. Zhang, « Synthesis and Antitumor Activity of a New Ergosterol Derivative », Chemistry of Natural Compounds, vol. 52, nᵒ 2, p. 252-255.
    Résumé : Ergosterol-3-O-(β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside) was efficiently synthesized and evaluated for its inhibitory activities against S180 cell lines compared with ergosterol. The structures of all synthesized compounds were fully characterized by spectroscopic data (NMR, MS). The antitumor activity of the new derivative was significantly enhanced compared with ergosterol.
    Mots-clés : GOBS, POLE 3.

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