Kun Zou

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Organization: China Three Gorges University

Department: Hubei Key Laboratory of Natural Products Research and Development, College of Biology and Pharmacy

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Chemicals
References

Three new terpenoids from the Eupatorium chinense

Co-reporter:Xiao-Qin Yu, Qing-Qing Zhang, Wei-Hong Yan, Lei Wang, ... Kun Zou

Phytochemistry Letters 2017 Volume 20(Volume 20) pp:

Publication Date(Web):1 June 2017

DOI:10.1016/j.phytol.2017.04.004

•Three new terpenoids compounds were isolated from the whole plant of Eupatorium chinense..•The structures of the isolated compounds were elucidated by spectroscopic means.•All of the isolated compounds were tested in vitro for their cytotoxic activities against four cancer cell lines.Three new terpenoids compounds (1–3) were obtained from ethyl acetate fraction, which was yielded from Eupatorium chinense’s ethanol extract. Their structures were determined on the basis of 1D and 2D NMR spectroscopy, including 1H-1H COSY, HMBC, HSQC and NOESY experiments. All of the isolated compounds were tested in vitro for their cytotoxic activities against the HepG2, HGC-27 and MDA-MB-231 cancer cell lines.Download high-res image (292KB)Download full-size image

Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and ‘click’ strategy

Co-reporter:Xiao-Feng Lu, Zheng Yang, Nian-Yu Huang, Hai-Bo He, Wei-Qiao Deng, Kun Zou

Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 17) pp:3726-3729

Publication Date(Web):1 September 2015

DOI:10.1016/j.bmcl.2015.06.028

To develop more effective antitumor steroidal drugs, we synthesized a library including twenty-two novel cytotoxic 2-alkyloxyl substituted (25R)-spirostan-1,4,6-triene-3-ones and corresponding 1,2,3-triazoles through an abnormal monoepoxide ring-opening/elimination and ‘click’ reactions. After the cytotoxic evaluations against HepG2, Caski and HeLa cell lines, three steroidal triazoles 5b, 5f and 5m in this library were found to possess potent anti-proliferative effects against Caski cells with the half-inhibitory concentrations (IC50) of 9.4–11.8 μM. The high-efficient and straightforward process was attractive feature for facile preparation of anti-tumor steroidal triazoles.

Paraconfuranones AH, eight new furanone analogs from the insect-associated fungus Paraconiothyrium brasiliense MZ-1

Co-reporter:Cheng-Xiong Liu;Lei Wang;Jian-Feng Chen;Zhi-Yong Guo;Xuan Tu;Zhang-Shuang Deng

Magnetic Resonance in Chemistry 2015 Volume 53( Issue 4) pp:317-322

Publication Date(Web):

DOI:10.1002/mrc.4197

Iron-catalyzed C(sp3)–H functionalization of methyl azaarenes with α-oxoesters: a facile approach to lactic acid derivatives

Co-reporter:Kun Jiang, Danwei Pi, Haifeng Zhou, Sensheng Liu, Kun Zou

Tetrahedron 2014 70(18) pp: 3056-3060

Publication Date(Web):

DOI:10.1016/j.tet.2014.02.069

Efficient Fixation of CO2 by a Zinc-Coordinated Conjugated Microporous Polymer

Co-reporter:Yong Xie;Ting-Ting Wang;Rui-Xia Yang;Dr. Nian-Yu Huang;Dr. Kun Zou;Dr. Wei-Qiao Deng

ChemSusChem 2014 Volume 7( Issue 8) pp:2110-2114

Publication Date(Web):

DOI:10.1002/cssc.201402162

Abstract

Zinc-coordinated conjugated microporous polymers (Zn-CMPs), prepared by linking salen zinc and 1,3,5-triethynylbenzene, exhibit extraordinary activities (turnover frequencies of up to 11600 h⁻¹), broad substrate scope, and group tolerance for the synthesis of functional organic carbonates by coupling epoxides with CO₂ at 120 °C and 3.0 MPa without the use of additional solvents. The catalytic activity of Zn-CMP is comparable to those of homogeneous catalysts and superior to those of other heterogeneous catalysts. This catalyst could be reused more than ten times without a significant decrease in performance.

Tupisteroide AC, three new polyhydroxylated steroidal constituents from the roots of Tupistra chinensis

Co-reporter:Cheng-Xiong Liu;Zhi-yong Guo;Yan-Hong Xue;Hong-Yan Zhang;Hong-Qi Zhang;Nian-Yu Huang

Magnetic Resonance in Chemistry 2012 Volume 50( Issue 4) pp:320-324

Publication Date(Web):

DOI:10.1002/mrc.2861

Three new steroidal compounds with polyhydroxy groups, tupisteroide A–C (1–3), were obtained from the roots of Tupistra chinensis, together with one known compound (4) that was isolated from this plant for the first time. The structures of tupisteroide A–C were determined on the basis of one- and two-dimensional NMR spectroscopy, including ¹H–¹H Correlation Spectroscopy, Heteronuclear Multiple Bond Correlation, and Heteronuclear Single Quantum Coherence experiments. The isolated compounds were evaluated for their cytotoxic activities against A549, HepG2, and CaSki cancer cell lines in vitro. Among them, compounds 1, 2, and 4 did not show significant inhibitory activity, but compound 3 showed cytotoxicity against A549 cancer cell lines with IC₅₀ values of 25.0 μM. Copyright © 2012 John Wiley & Sons, Ltd.

Docking study on trametenolic acid B as a α-glucosidase inhibitor

Co-reporter:Hua-Jun Luo;Jun-Zhi Wang;Yuan Zhou

Medicinal Chemistry Research 2012 Volume 21( Issue 9) pp:2141-2144

Publication Date(Web):2012 September

DOI:10.1007/s00044-011-9741-y

Trametenolic acid B is a potent, non-sugar α-glucosidase inhibitor with IC50 value 17.09 μM. The homology model structure of S. cerevisiae α-glucosidase was built based on the template provided by B. cereus oligo-1,6-glucosidase (PDB code: 1UOK) and used for molecular docking. Docking simulation between trametenolic acid B and α-glucosidase was performed using ArgusLab docking method and the binding free energy of the docked complex after the molecular dynamics simulation is –16.31 kcal/mol. The hydrogen bond could be formed between trametenolic acid B and the α-glucosidase amino acid residue Asp214. There may be hydrophobic space interactions between methyl groups of trametenolic acid B and the amino acid residues Tyr71, Phe157, Phe158, Thr215, Phe300, and Val303.

Docking study on chlorogenic acid as a potential H5N1 influenza A virus neuraminidase inhibitor

Co-reporter:Hua-Jun Luo;Jun-Zhi Wang;Jian-Feng Chen

Medicinal Chemistry Research 2011 Volume 20( Issue 5) pp:554-557

Publication Date(Web):2011 June

DOI:10.1007/s00044-010-9336-z

Docking simulation between chlorogenic acid and H5N1 influenza virus neuraminidase (NA) was performed and the binding free energies of the best pose and average for the best three different poses of H5N1 NA–chlorogenic acid complex are −9.71 and −9.27 kcal/mol, respectively, which is lower than those of H5N1 NA–oseltamivir complex (−7.13 and −6.39 kcal/mol) by using ArgusLab docking method. The hydrogen bonds could be formed between chlorogenic acid and the H5N1 NA amino acid residues Arg156 and Thr439. Arg152 from the 150-cavity makes polar contact with the –COOH group in chlorogenic acid. Chlorogenic acid could be a potential H5N1 influenza A virus NA inhibitor.

Structural elucidation of four new furostanol saponins from Tupistra chinensis by 1D and 2D NMR spectroscopy

Co-reporter:Kun Zou;Jun-zhi Wang;Zhi-yong Guo;Ming Du;Jun Wu;Yuan Zhou;Fei-jun Dan;Chuang Liu

Magnetic Resonance in Chemistry 2009 Volume 47( Issue 1) pp:87-91

Publication Date(Web):

DOI:10.1002/mrc.2332

Abstract

Four new furostanol saponins (1–4), two pairs of diastereoisomers, were isolated from methanolic extracts of Tupistra chinensis rhizomes and their structures were assigned from ¹H and ¹³C NMR spectra, DEPT, and by 2D COSY, NOESY, HMQC, and HMBC experiments. Copyright © 2008 John Wiley & Sons, Ltd.

Structural elucidation and NMR spectral assignment of three new furostanol saponins from the roots of Tupistra chinensis

Co-reporter:Zhiyong Guo;Junzhi Wang;Chuang Liu;Zichun Tang ;Chunyan Yang

Magnetic Resonance in Chemistry 2009 Volume 47( Issue 7) pp:613-616

Publication Date(Web):

DOI:10.1002/mrc.2436

Abstract

Three new furostanol saponins (1–3) were isolated from the roots of Tupistra chinensis (T. chinensis). And their structures were elucidated on the basis of NMR and mass spectrometry (MS) spectral analysis. Copyright © 2009 John Wiley & Sons, Ltd.

Diastereoisomeric saponins from the rhizomes of Tupistra chinensis

Co-reporter:Kun Zou, Jun Wu, Ming Du, Chuang Liu, Zi Chun Tang, Jun Zhi Wang

Chinese Chemical Letters 2007 Volume 18(Issue 1) pp:65-68

Publication Date(Web):January 2007

DOI:10.1016/j.cclet.2006.11.024

A pair of diastereoisomeric furostanol saponins was obtained from the n-butanol fraction of methanol extract from Tupistra chinensis rhizomes, a folk medicine of Shennongjia Forest District of Hubei Province. Their structures were determined, on the basis of chemical and spectroscopic evidences.

Furostanol saponins with inhibitory action against COX-2 production from Tupistra chinensis rhizomes

Co-reporter:Kun Zou, Jun Zhi Wang, Jun Wu, Yuan Zhou, Chuang Liu, Fei Jun Dan, Ya Xiong Zhang, Jin Yang

Chinese Chemical Letters 2007 Volume 18(Issue 10) pp:1239-1242

Publication Date(Web):October 2007

DOI:10.1016/j.cclet.2007.06.018

Two furostanol saponins were obtained from the n-butanol fraction of methanol extract from Tupistra chinensis rhizomes, a folk medicine of Shennongjia Forest District of Hubei Province. Their structures were determined as (25S)-26-O-(β-d-glucopyranosyl)-furost-1β, 3β, 22α, 26-tetrol-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside (1) and (25R)-26-O-(β-d-glucopyranosyl)-furost-1β, 3β 22α, 26-tetrol 3-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside (2), on basis of chemical and spectroscopic evidences. 1 and 2 displayed marked inhibitory action towards COX-2 production in macrophages of the rat abdomen induced by LPS at 20 μg/mL.

Comparison of cardioprotective effects of labeled and unlabeled oleanoic acids with new BOPIM dye on primary neonatal rat cardiomyocytes following hypoxia/reoxygenation injury

Co-reporter:Sa Wang, Hai-bo He, Shu-zhang Xiao, Jun-zhi Wang, ... Kun Zou

Pharmacological Reports (August 2014) Volume 66(Issue 4) pp:677-685

Publication Date(Web):1 August 2014

DOI:10.1016/j.pharep.2014.03.014

BackgroundIt is well known that fluorescent labeling has recently become a major research tool in molecular and cellular biology for demonstrating therapeutic mechanisms and metabolic pathways. However, few studies have reported the use of fluorescent labeling of natural products.MethodsWe recently explored the boron 2-(2′-pyridyl) imidazole (BOPIM) derivative analogs, which are highly fluorescent, non-aggregated, and nontoxic. In the present study, the natural product oleanolic acid (OA) was functionalized and labeled with BOPIM, thus yielding a highly fluorescent probe, the comparison of cardioprotective effects of labeled and unlabeled OAs with BOPIM on primary neonatal rat cardiomyocytes with hypoxia/reoxygenation (H/R) injury were investigated.ResultsPretreatment with OA and BOPIM-OA significantly prevented the H/R induced cell death in primary neonatal rat cardiomyocytes. However, BOPIM exhibited no improvements on the H/R injury cardiomyocytes, and which were similar to those of the H/R group. The results of comparison of cardioprotective effects between labeled and unlabeled OAs with BOPIM showed that introducing the BOPIM chromophore did not make a difference with H/R injury cardiomyocytes.ConclusionBOPIM chromophore is a suitable probe for investigating the pharmacological mechanisms of natural products.