4-酰基吡唑啉酮-5缩γ-氨基丁酸衍生物的合成及对白玉菇菌丝脱氢酶活性影响

doi:10.19640/j.cnki.jtau.2022.02.001

天津农学院学报 ›› 2022, Vol. 29 ›› Issue (2): 1-6.doi: 10.19640/j.cnki.jtau.2022.02.001

• 研究与简报 • 下一篇

4-酰基吡唑啉酮-5缩γ-氨基丁酸衍生物的合成及对白玉菇菌丝脱氢酶活性影响

王鑫^a, 史芯沂美^a, 谢芬兰^a, 付壮^a, 朱华玲^{a,通信作者}, 班立桐^b

天津农学院 a.基础科学学院,b.农学与资源环境学院,天津 300392

收稿日期:2020-10-30 出版日期:2022-06-30 发布日期:2022-07-05
通讯作者: 朱华玲（1975—）,女,副教授,硕士,主要从事功能化合物的合成与应用研究。E-mail: zhuhualing2004@126.com。
作者简介:王鑫（2000—）,女,本科在读,研究方向：功能化合物的合成与应用。E-mail: 1044569223@qq.com。
基金资助:
天津市大学生创新创业训练计划项目（202010061058）; 天津市蔬菜产业技术体系创新团队项目（ITTVRS2017015）

Synthesis of the derivatives from 4-acylpyrazolone-5 and γ-aminobutyric acid and their effects on the dehydrogenase activity of Hypsizygus marmoreus mycelia

Wang Xin^a, Shi Xinyimei^a, Xie Fenlan^a, Fu Zhuang^a, Zhu Hualing^{a,Corresponding Author}, Ban Litong^b

Tianjin Agricultural University, a. College of Basic Sciences, b. College of Agronomy and Resource Environment, Tianjin 300392, China

Received:2020-10-30 Online:2022-06-30 Published:2022-07-05

摘要/Abstract

摘要： 采用结构拼接法设计合成了4-三氟乙酰-3-甲基-1-苯基-5-吡唑啉酮缩γ-氨基丁酸（L1）、1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮缩γ-氨基丁酸（L2）两种新配体,以及两个配体的Ca、Zn配合物。采用红外分光光度法和紫外分光光度法对合成的6种化合物进行了结构表征,采用MTT法测定了6种化合物对白玉菇菌丝脱氢酶活性的影响。结果表明：6种化合物对白玉菇菌丝脱氢酶的活性均有抑制作用,其中配体L2对白玉菇菌丝脱氢酶活性的抑制能力最强,配体L1最差;采用分子对接法研究了菌丝脱氢酶与原始配体泛醌,以及配体L1和L2的相互作用,发现两个新配体与菌丝脱氢酶的结合能力均好于原始配体泛醌,且配体L2好于配体L1。该结果与MTT试验结果一致,说明配体L1和配体L2可能是通过与泛醌进行结合竞争表现出对琥珀酸脱氢酶的抑制活性。

关键词: γ-氨基丁酸, 衍生物, 合成, 表征, 白玉菇, 菌丝脱氢酶活性

Abstract: A new ligand（L1）derived from γ-aminobutyric acid and 4-trifluoroacetyl-3- methyl-1-phenyl-5-pyrazolone, and a new ligand（L2）derived from γ-aminobutyric acid and 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone were synthesized and characterized by IR and UV, so did their Ca, Zn complexes. The inhibititted effect of the compounds on the mycelium dehydrogenase activity of Hypsizygus marmoreus was determined by MTT methods. The results showed that ligand L2 had stronger inhibitition ability to mycelium dehydrogenase while ligand L1 was the weaker. Molecular docking method was used to analysize the interaction of the mycelium dehydrogenase and the ligands. The results suggested that the two new ligands showed higher interactions to mycelium dehydrogenase than original ubiquinone, and ligand L2 showed higher interactions to mycelium dehydrogenase than ligand L1.

Key words: γ-aminobutyric acid, derivatives, synthesis, scharacterization, Hypsizigus marmoreus, dehydrogenase activity

中图分类号:

O621.1

王鑫, 史芯沂美, 谢芬兰, 付壮, 朱华玲, 班立桐. 4-酰基吡唑啉酮-5缩γ-氨基丁酸衍生物的合成及对白玉菇菌丝脱氢酶活性影响[J]. 天津农学院学报, 2022, 29(2): 1-6.

Wang Xin, Shi Xinyimei, Xie Fenlan, Fu Zhuang, Zhu Hualing, Ban Litong. Synthesis of the derivatives from 4-acylpyrazolone-5 and γ-aminobutyric acid and their effects on the dehydrogenase activity of Hypsizygus marmoreus mycelia[J]. Journal of Tianjin Agricultural University, 2022, 29(2): 1-6.

导出引用管理器 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

链接本文: http://xuebao.tjau.edu.cn/CN/10.19640/j.cnki.jtau.2022.02.001

http://xuebao.tjau.edu.cn/CN/Y2022/V29/I2/1

参考文献

[1] WONG C G T,BOTTIGLIERI T,SNEAD O C. GABA,gamma-hydroxybutyric acid,and neurological disease[J]. Ann Neurol,2003,54(Suppl 6):S3-S12.
[2] 程传兴,刘晓飞,王薇. γ-氨基丁酸的生理功能及制备方法[J]. 哈尔滨商业大学学报(自然科学版),2017,33(6):693-697.
[3] 李珂,徐恩. γ-氨基丁酸在中枢神经系统发育中的作用及机制[J]. 神经科学通报(英文版),2008,24(3):195-200.
[4] 杨胜远,陆兆新,吕风霞,等. γ-氨基丁酸的生理功能和研究开发进展[J]. 食品科学,2005,26(9):546-551.
[5] PRIYA M,SHARMA L,KAUR R.et al.GABA (γ- aminobutyric acid),as a thermo-protectant,to improve the reproductive function of heat-stressed mungbean plants[J]. Sci Rep,2019,9(1):7788-7802.
[6] 林亲录,王婧,陈海军. γ-氨基丁酸的研究进展[J]. 现代食品科技,2008,24(5):496-500.
[7] 王姣姣,白卫东,梁彬霞. γ-氨基丁酸的生理功能及富集的研究进展[J]. 农产品加工(学刊),2012(1):40-42,45.
[8] SHILPA J,PRETTY M A,ANITHA M,et al.Gamma aminobutyric acid B and 5-hydroxy tryptamine 2A receptors functional regulation during enhanced liver cell proliferation by GABA and 5-HT chitosan nanoparticles treatment[J]. Eur J Pharmacol,2013,715(1/3):154-163.
[9] GAO Z F,XIE W J,ASHRAF U,et al.Exogenous γ-aminobutyric acid(GABA)application at different growth stages regulates 2-acetyl-1-pyrroline,yield,quality and antioxidant attributes in fragrant rice[J]. J Plant Interact,2020,15(1):139-152.
[10] 王辉,项丽丽,张锋华. γ-氨基丁酸(GABA)的功能性及在食品中的应用[J]. 食品工业,2013,34(6):186-189.
[11] ZHOU L,YAN P,BINGRU H.Alteration of transcripts of stress-protective genes and transcriptional factors by γ- aminobutyric acid(GABA)associated with improved heat and drought tolerance in creeping bentgrass(Agrostis stolonifera)[J]. Int J Mol Sci,2018,19(6):1623-1640.
[12] 张亚青. 高产γ-氨基丁酸(GABA)食用菌资源的筛选与利用[D]. 杭州:浙江科技学院,2020.
[13] 李俊华. 有机催化构建新型吡唑啉酮衍生物的研究[D]. 北京:北京理工大学,2019.
[14] OKAFOR E C.The metal complexes of heterocyclic β-diketones and their derivatives-VI. The synthesis, structure and i.r. spectral studies of some new metal(II)complexes of 1- phenyl-3-methyl-4-benzoyl-pyrazolone-5(HPMBP)[J]. Spectrochimica Acta Part A Molecular Spectroscopy,1981,37(11):945-950.
[15] MARCHETTI F,PETTINARI C,PETTINARI R.Acylp- yrazolone ligands:Synthesis,structures,metal coordination chemistry and applications[J]. Coordin Chem Rev,2005,249(24):2909-2945.
[16] 李锦州,蒋礼,安郁美. 呋喃甲酰基吡唑啉酮缩β-丙氨酸配合物的合成、表征及生物活性[J]. 应用化学,2004,21(2):150-153.
[17] SANNER M F.Python:A programming language for software integration and development[J]. J Mol Graph Model,1999,17(1):57-61.
[18] MORRIS G M,HUEY R,LINDSTROM W,et al.Autodock4 and AutoDockTools4:Automated docking with selective receptor flexiblity[J]. J Computat Chem,2009,30(16):2785-2791.
[19] 刘举,宫雪,徐亮,等. 光谱法联合分子对接研究人血清白蛋白与新的抗肿瘤活性小分子的体外结合[J]. 分析测试学报,2018,37(4):20-27.

4-酰基吡唑啉酮-5缩γ-氨基丁酸衍生物的合成及对白玉菇菌丝脱氢酶活性影响

Synthesis of the derivatives from 4-acylpyrazolone-5 and γ-aminobutyric acid and their effects on the dehydrogenase activity of Hypsizygus marmoreus mycelia

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价

[1]	罗希帆, 周灵美, 谢晓东, 陈帅君, 杨红澎, 吴疆. 一氧化氮合成酶的基因克隆与功能鉴定[J]. 天津农学院学报, 2022, 29(2): 13-17.
[2]	张莉, 刘洁, 吴倩, 贺攀华, 朱华玲, 黄治强. 含甘二肽甲酯结构的β-二酮衍生物的合成、除草抑菌活性及构效关系[J]. 天津农学院学报, 2017, 24(1): 52-57.
[3]	杨延波, 李恒, 潘虹, 石军, 赵蔚鑫. 氨基酸衍生物介入的支化聚乳酸的合成研究[J]. 天津农学院学报, 2017, 24(1): 62-65.
[4]	李萍, 许艳玲, 尚志强. 环氧亚麻油增塑剂的优化合成与表征[J]. 天津农学院学报, 2016, 23(1): 38-42.
[5]	朱华玲, 班立桐, 石军, 卜路霞, 尉震. 苯甲酰丙酮反应位点预测及金属配合物的合成、表征和抑菌活性[J]. 天津农学院学报, 2012, 19(4): 18-23.
[6]	张淼, 许玮, 任俊杰, 朱华玲, 白亚南, 王学荣. 新型4-氨基安替比林席夫碱的合成、表征和抑菌活性[J]. 天津农学院学报, 2012, 19(1): 30-33.