银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究

doi:10.3969/j.issn.0253-2417.2016.06.005

林产化学与工业 ›› 2016, Vol. 36 ›› Issue (6): 29-34.doi: 10.3969/j.issn.0253-2417.2016.06.005

银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究

陶冉^1,2, 王成章^1,2, 叶建中¹, 周昊^1,2, 陈虹霞¹

1. 中国林业科学研究院林产化学工业研究所, 生物质化学利用国家工程实验室, 国家林业局林产化学工程重点开放性实验室, 江苏省生物质能源与材料重点实验室, 江苏南京 210042;
2. 中国林业科学研究院林业新技术研究所, 北京 100091

收稿日期:2015-12-31 出版日期:2016-12-25 发布日期:2016-12-23
通讯作者: 王成章,男,研究员,博士,博士生导师,主要从事天然产物研究与利用工作;E-mail:wangczlhs@sina.com E-mail:wangczlhs@sina.com
作者简介:陶冉(1982-),男,江苏连云港人,助理研究员,博士,主要从事天然产物化学研究;E-mail:trmoon1949@163.com
基金资助:
江苏省自然科学青年基金项目（BK20150070）；中国林科院林业新技术所基本科研业务费专项资金（CAFINT2014C10）；江苏省林业三新工程项目（LYSX[2014]09）

Synthesis and Antibacterial Activity of Nitrogenated and Haloid Derivatives of Ginkgo Biloba Leaves Polyprenol

TAO Ran^1,2, WANG Cheng-zhang^1,2, YE Jian-zhong¹, ZHOU Hao^1,2, CHEN Hong-xia¹

1. Institute of Chemical Industry of Forest Products, CAF, National Engineering Lab. for Biomass Chemical Utilization, Key and Open Lab. of Forest Chemical Engineering, SFA, Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China;
2. Research Institute of Forestry New Technology, CAF, Beijing 100091, China

Received:2015-12-31 Online:2016-12-25 Published:2016-12-23

摘要/Abstract

摘要： 利用含氮和含卤素试剂对银杏叶聚戊烯醇末端羟基进行含氮和含卤素的衍生化改性，结果得到5种衍生物，分别为聚戊烯基邻苯二甲酰亚胺（GPH）、氨基聚戊烯醇（GAM）、聚戊烯基季铵盐（GAS）、聚戊烯基三氟乙酰（GTF）和聚戊烯基氯乙酰（GCH），并用¹H NMR分别表征并证实了产物结构。通过比较产物抑菌圈直径和最小抑质量浓度（MIC）来筛选出抗菌作用较强的衍生物，结果显示：GAS对于大肠杆菌和金黄色葡萄球菌的抗菌活性均为最高，其抑菌圈为19.1~19.8 mm，MIC均为31.3 mg/L。同时研究了GAS在亚抑菌质量浓度下（15.6 mg/L）对大肠杆菌和金黄色葡萄球菌的杀菌曲线，结果显示：GAS对大肠杆菌和金黄色葡萄球菌在48 h内具有一定抗菌性；在前8 h内，GAS对于大肠杆菌和金黄色葡萄球菌的杀菌作用较强，致使菌群数量迅速下降；8 h以后，两种菌群都有不同程度的再生，抑菌活性减弱。

关键词: 聚戊烯醇衍生物, 合成, 抗菌活性, 银杏叶

Abstract: Chemical structure modification of -OH in α-terminal unit of Ginkgo biloba leaves polyprenol (GBP) was conducted to prepare five nitrogenated and haloid derivatives of GBP,i.e., polyprenyl phthalimides (GPH), polyprenyl amines (GAM), polyprenyl quaternary ammonium salt (GAS), polyprenyl trifluoroacetate (GTF) and polyprenyl chloroacetate (GCH). All derivatives were identified by ¹H NMR. In the study of antibacterial activity, GAS had the highest antibacterial activity against strains Escherichia coli and Staphylococcus aureus with inhibition halos of 19.1-19.8 mm and the minimal inhibitory concentration(MIC) of 31.3 mg/L. At the same time, the time-killing curves of GAS against E.coli and S.aureus under sub-MIC of 15.6 mg/L were drawn and studied. And the results showed that GAS possessed antibacterial activity against E.coli and S.aureus in 48 h and the bacterial number was in a rapid decline within 8 h of exposure in the time-kill studies.

Key words: polyprenol derivatives, synthesis, antibacterial activity, Ginkgo biloba leaves

中图分类号:

TQ35

陶冉, 王成章, 叶建中, 周昊, 陈虹霞. 银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究[J]. 林产化学与工业, 2016, 36(6): 29-34.

TAO Ran, WANG Cheng-zhang, YE Jian-zhong, ZHOU Hao, CHEN Hong-xia. Synthesis and Antibacterial Activity of Nitrogenated and Haloid Derivatives of Ginkgo Biloba Leaves Polyprenol[J]. Chemistry and Industry of Forest Products, 2016, 36(6): 29-34.

参考文献

[1] 王成章,王婉苓,叶建中,等.分子短程蒸馏分离银杏叶聚戊烯醇的研究[J].林产化学与工业,2008,28(3):23-27. WANG Cheng-zhang,WANG Wan-ling,YE Jian-zhong,et al.Studies on seperation of polyprenols from leaves of Ginkgo biloba L.by molecular short distillation[J].Chemistry and Industry of Forest Products,2008,28(3):23-27.
[2] 王成章,沈兆邦,陈祥.落叶松和水杉针叶的聚戊烯醇[J].植物资源与环境,1996,5(4):21-25. WANG Cheng-zhang,SHEN Zhao-bang,CHEN Xiang.Polyprenols from Larixgmelini (Rupr.) Rupr.and Metasequoia glyptostroboides Huet Cheng needles[J].Journal of Plant Resources and Environment,1996,5(4):21-25.
[3] 王成章,沈兆邦,陈祥.五种针叶中聚戊烯醇的化学结构[J].林产化学与工业,1994,14(3):1-8. WANG Cheng-zhang,SHEN Zhao-bang,CHEN Xiang.Structure of polyprenols from five conifer needles[J].Chemistry and Industry of Forest Products,1994,14(3):1-8.
[4] 段鑫,陶冉,薛志革,等.桑叶中聚戊烯醇结构与含量测定[J].天然产物研究与开发,2014,26(6):886-889. DUAN Xin,TAO Ran,XUE Zhi-ge,et al.Identification and determination of polyprenols in Mulberry leaf[J].Natural Product Research and Development,2014,26(6):886-889.
[5] 陶冉,王成章,孔振武.Py-GC-MS研究水提取前后银杏叶化学成分的变化[J].林产化学与工业,2013,33(2):55-60. TAO Ran,WANG Cheng-zhang,KONG Zhen-wu.Component varieties of Ginkgo biloba L.leaves before and after extraction with water by Py-GC-MS[J].Chemistry and Industry of Forest Products,2013,33(2):55-60.
[6] FEDOTOVA J,SOULTANOV V,NIKITINA T,et al.Ropren is a polyprenol preparation from coniferous plants that ameliorates cognitive deficiency in a rat model of beta-amyloid peptide-(25-35)-induced amnesia[J].Phytomedicine,2012,19(5):451-456.
[7] PRONIN A V,DANILOV L L,NAROVLYANSKY A N,et al.Plant polyisoprenoids and control of cholesterol level[J].Archivum Immunologiae et Therapiae Experimentalis,2014,62(1):31-39.
[8] 王成章,沈兆邦,谭卫红,等.银杏叶聚戊烯醇的化学、纯化和药效研究[J].天然产物研究与开发,2001,13(2):43-45. WANG Cheng-zhang,SHEN Zhao-bang,TAN Wei-hong,et al.The studies on the chemistry,purification and pharmacology of polyprenols from Ginkgo biloba L.[J].Natural Product Research and Development,2001,13(2):43-45.
[9] YANG Lan,WANG Cheng-zhang,YE Jian-zhong,et al.Hepatoprotective effects of polyprenols from Ginkgo biloba L.leaves on CCl₄-induced hepatotoxicity in rats[J].Fitoterapia,2011,82:834-840.
[10] FEDOTOVA I O,SULTANOV V S,KUZNETSOVA N N,et al.Effect of new polyprenol drug ropren on anxiety-depressive-like behavior in rats with experimental Alzheimer disease[J].Eksp Klin Farmakol,2010,73:2-5.
[11] TAO Ran,WANG Cheng-zhang,KONG Zhen-wu.Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L.Leaves[J].Molecules,2013,18:2166-2182.
[12] GRIGOR'EVA N Y,AVRUTOV I M,PINSKER O A,et al.Directed aldol condensation as a stereoselective method for the synthesis of Z-trisubstituted olefins[J].Bulletin of the Academy of Sciences of the Ussr Division of Chemical Science,1985,34(34):1673-1685.
[13] TAHARA Y,KOYAMA H,KOMATSU Y,et al.Nonyl prenyl-N heterocyclics:U.S.4755601[P].1988-01-01
[14] DANILOV L L,MALTSEV S D,DEYEVA A V,et al.Phosprenyl:A novel drug with antiviral and immunomodulatory activity[J].Archivum Immunologiae Et Therapiae Experimentalis,1996,44(5/6):395-400.
[15] TAO Ran,WANG Cheng-zhang,YE Jian-zhong,et al.Antibacterial/antifungal activity and synergistic interactions between C₇₀-C₁₂₀ polyprenol homologs from Ginkgo Biloba L.leaves and the corresponding synthetic derivatives[J].European Food Research and Technology,2014,239(4):587-594.
[16] 周彦, 王成章, 李在均.银杏叶聚戊烯醇及其衍生物的抑菌活性研究[J].林产化学与工业, 2013, 33(4):53-56. ZHOU Yan,WANG Cheng-zhang,LI Zai-jun.Antibacterial activity of the Ginkgo biloba polyprenols and their derivatives[J].Chemistry and Industry of Forest Products,2013,33(4):53-56.
[17] SHANG Ruo-feng,WANG Guan-hua,XU Xi-ming,et al.Synthesis and biological evaluation of new pleuromutilin derivatives as antibacterial agents[J].Molecules,2014,19:19050-19065.
[18] VINCENT H T,SAMER K,GIAO V,et al.Comparative pharmacodynamics of gentamicin against Staphylococcus aureus and Pseudomonas aeruginosa[J].Antimicrob Agents Ch,2006,50(8):2626-2631.
[19] SIZOVA O V,UTKINA N S,KALINCHUK N A,et al.Synthesis of a quanternary polyprenyl ammonium salt[J].Acta Biochimica Polonica,2007,54(4):869.
[20] VESELOVSKY V V,LOZANOVA A V.Synthesis of polyprenylamines from plant polyprenols[J].Russian Chemical Bulletin,2003,52(10):2290-2291.
[21] KENAWY E,ABDEL-HAY F I,ABD E E,et al.Biologically active polymers.V:Synthesis and antimicrobial activity of modified poly(glycidyl methacrylate-co-2-hydroxyethyl methacrylate) derivatives with quaternary ammonium and phosphonium salts[J].Journal of Polymer Science Part A:Polymer Chemistry,2002,40(14):2384-2393.
[22] KANAZAWA A,IKEDA T,ENDOT.Novel polycationic biocides:Synthesis and antibacterial activity of polymeric phosphonium salts[J].Journal of Polymer Science Part A:Polymer Chemistry,1993,31(2):335-343.
[23] LU Gui-qian,WU Ding-cai,FU Ruo-wen.Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate[J].Reactive & Functional Polymers,2007,67(4):355-366.
[24] BAUDRION F,VACELET A P E.Influence of concentration and structure of quaternary ammonium salts on their antifouling efficiency tested against a community of marine bacteria[J].Biofouling,2000,14(4):317-331.
[25] KANAZAWA A,IKEDA T,ENDO T.Polymeric phosphonium salts as a novel class of cationic biocides.ix:Effect of side-chain length between main chain and active group on antibacterial activity[J].Jornal of Olymr N Ar A Olymr Hmry,1994,32(10):1997-2001.

银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究

Synthesis and Antibacterial Activity of Nitrogenated and Haloid Derivatives of Ginkgo Biloba Leaves Polyprenol

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

关于本刊

投稿指南

在线期刊

相关单位

联系我们

[1]	卢言菊, 赵振东, 王婧, 徐士超, 毕良武, 陈玉湘. 异海松酸糠醛类酰腙化合物的合成及生物活性研究[J]. 林产化学与工业, 2019, 39(3): 43-48.
[2]	杨小华, 诸进华, 张燕, 李守海, 李梅. 蓖麻油基水性环氧固化剂的合成及性能[J]. 林产化学与工业, 2019, 39(3): 65-71.
[3]	徐士超, 曾小静, 董欢欢, 赵振东. 萜类植物源除草活性物开发及应用研究进展[J]. 林产化学与工业, 2019, 39(2): 1-8.
[4]	冯雪贞, 肖转泉, 卢平英, 范国荣, 王宗德. 氢化诺卜基二甲基烷基卤化铵的合成及抑菌活性[J]. 林产化学与工业, 2019, 39(1): 35-40.
[5]	檀贯妮, 高亚楠, 高宏, 商士斌, 宋湛谦. 含双萘的脱氢枞酸三芳胺化合物的合成及光谱性能[J]. 林产化学与工业, 2019, 39(1): 61-66.
[6]	翟兆兰, 闫鑫焱, 许吉, 宋湛谦, 商士斌, 饶小平. 马来海松酸长链烷基酰(亚)胺钠的合成及其对小地老虎的拒食活性研究[J]. 林产化学与工业, 2018, 38(5): 23-29.
[7]	陶冉, 王成章, 张昌伟, 周昊, 陈虹霞. 桦木醇选择性氧化产物的合成及抗肿瘤活性研究[J]. 林产化学与工业, 2018, 38(4): 47-51.
[8]	李翔宇, 李学琴, 时君友, 雷廷宙. 生物质炭基磁性固体酸催化剂研究进展[J]. 林产化学与工业, 2017, 37(5): 9-18.
[9]	张瑞, 段文贵, 林桂汕, 陈智聪, 何冉, 雷福厚. 马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性[J]. 林产化学与工业, 2017, 37(5): 68-78.
[10]	袁晓敏, 张平辉, 涂永元, 王婧, 李冬梅, 赵振东. 合成冰片草酸酯中间体成分气相色谱分析方法的研究与应用[J]. 林产化学与工业, 2017, 37(5): 93-100.
[11]	李侨光, 刘鹤, 商士斌, 宋湛谦. 松香及其衍生物改性高分子材料的研究进展[J]. 林产化学与工业, 2017, 37(4): 23-29.
[12]	金霖霖, 肖转泉, 范国荣, 陈金珠, 王鹏, 王宗德, 陈尚钘. N-氢化诺卜基吡啶类卤化铵的合成及抑菌活性研究[J]. 林产化学与工业, 2017, 37(3): 122-128.
[13]	朱守记, 杨学兵, 徐士超, 赵振东, 蒋建新. 顺-1,8-对烷二胺双酰胺杂环类衍生物的合成及抑菌活性研究[J]. 林产化学与工业, 2017, 37(2): 79-84.
[14]	马媛, 段文贵, 林桂汕, 刘陆智, 黄正松, 雷福厚. 紫苏醛基席夫碱-(硫)脲化合物的合成及生物活性[J]. 林产化学与工业, 2017, 37(1): 54-62.
[15]	芮坚, 杨金来, 蔡涛, 徐徐, 王石发. 异长叶烯基噻唑类化合物的合成及其抑菌、抗肿瘤活性研究[J]. 林产化学与工业, 2016, 36(6): 41-48.