具类辣素结构乙酰胺的合成及其抑菌、抑藻性能
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摘要
以取代芳香烃和N-羟甲基乙酰胺为原料,采用傅-克烷基化反应设计合成了7种具类辣素结构乙酰胺化合物(Ⅰ～Ⅶ)。利用IR和~1HNMR对其结构进行了表征。以大肠杆菌和金黄色葡萄球菌为受试菌评价了其抑菌活性,以三角褐指藻、中肋骨条藻和旋链角毛藻为受试藻评价了其抑藻活性。结果表明:7种化合物对2种菌和3种藻均具有较好的抑制作用,其中以3-乙酰胺甲基-4-肉桂苯酚(Ⅶ)的抑制作用最好,最小抑菌浓度可达到0.0625 g/L,且质量浓度为3 g/L时抑菌率与抑藻率均超过90%。
Seven kind of new acetamide compounds containing capsaicin moieties(Ⅰ～Ⅶ) were synthesized from aromatic hydrocarbons with N-hydroxymethylacetamide via Friedel-Crafts alkylation reaction and characterized by IR and ~1HNMR. Their bacteriostatic activities were evaluated by Escherichia coli and Staphylococcus aureus. Their algal inhibition activities against Phaeodactylumtricornutum, Skeletonemacostatum and Chaetoceroscurvisetus were also evaluated.The results showed that all of compounds exhibited good inhibition effects against two kinds of bacteria and three kinds of algae. In particular, compound Ⅶ(N-[2-hydroxy-5-(1-methyl-1-phenyl-ethyl)-benzyl]-acetamide) had the best inhibition effect. The minimal antibacterial concentration was 0.0625 g/L, and both bacteriostasic rate and alga growth inhibition rate were over 90% at 3 g/L.
Seven kind of new acetamide compounds containing capsaicin moieties(Ⅰ～Ⅶ) were synthesized from aromatic hydrocarbons with N-hydroxymethylacetamide via Friedel-Crafts alkylation reaction and characterized by IR and ~1HNMR. Their bacteriostatic activities were evaluated by Escherichia coli and Staphylococcus aureus. Their algal inhibition activities against Phaeodactylumtricornutum, Skeletonemacostatum and Chaetoceroscurvisetus were also evaluated.The results showed that all of compounds exhibited good inhibition effects against two kinds of bacteria and three kinds of algae. In particular, compound Ⅶ(N-[2-hydroxy-5-(1-methyl-1-phenyl-ethyl)-benzyl]-acetamide) had the best inhibition effect. The minimal antibacterial concentration was 0.0625 g/L, and both bacteriostasic rate and alga growth inhibition rate were over 90% at 3 g/L.
引文
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[25]Feng Wen(冯文),Wang Xianghui(王向辉),Song Huangwang(宋煌旺),et al.Syntheses and QSAR study on anti-algae activities of benzisothiazolin-3-one derivatives[J].Chemistry(化学通报),2017,80(12):1133-1147.
[26]Wang Jin(汪瑾),Du Mingyong(杜明勇),Yu Yufeng(于玉凤),et al.The inhibitory effect of plant extracts on Microcystis aeruginosa and its algal inhibiting characteristics[J].Journal of Nanjing Agricultural University(南京农业大学学报),2014,37(4):91-94.
[27]Zhong Yunxiao(种云霄),Tang Zhongen(汤仲恩),Yu Guangwei(余光伟),et al.Growth inhibition of blue-green algae by submerged macrophytes culture solutions with existence of the low level of copper ion[J].Ecology and Environmental Sciences(生态环境学报),2012,21(9):1594-1598.
[28]Xu Huanzhi(徐焕志),Yu Liangmin(于良民),Li Changcheng(李昌诚),et al.Synthesis of acrylamides containing capsaicin derivative moiety and their growth inhibition against Nitzschia closterium[J].Chinese Journal of Applied Chemistry(应用化学),2007,24(8):911-916.
[2]Yu Xiaolin(于晓琳),Yu Liangmin(于良民),Jiang Xiaohui(姜晓辉).Synthesis,bacteriostasic activity and antifouling capability of acrylamides containing capsaicin moieties[J].Chinese Journal of Applied Chemistry(应用化学),2014,31(5):594-599.
[3]O’Neill J,Brock C,Olesen A E,et al.Unravelling the mystery of capsaicin:A tool to understand and treat pain[J].Pharmacological Reviews,2012,64(4):939-971.
[4]Jin Yong(金涌),Li Jun(李俊),Yao Hongwei(姚宏伟),et al.Antiinflammatory and analgesic effects of extract of capsicum[J].Acta Universitatis Medicinalis Anhui(安徽医药大学学报),2001,36(6):430-431.
[5]Jiang Xiayun(江霞云),Ma Fengsen(马凤森),Wu Xiaojuan(吴小娟).Study of capsaicin emulgel on in vitro transdermal permeation,analgesic actions,and irritation[J].Chinese Traditional and Herbal Drugs(中草药),2018,49(7):1569-1575.
[6]Inés D L.Effect of capsaicin on prostate cancer cells[J].Future Oncology,2010,6(10):1545-1550.
[7]Thoennissen N H,O’Kelly J,Lu D,et al.Capsaicin causes cell-cycle arrest and apoptosis in ER-positive and-negative breast cancer cells by modulating the EGFR/HER-2 pathway[J].Oncogene,2010,29:285-296.
[8]Xie Zhiqin(谢智钦),Li Hongxia(李弘夏),Tang Caixi(唐才喜),et al.Capsaicin induces apoptosis in HepG2 cells through ROSactivation[J].China Cancer(中国肿瘤),2018,27(6):470-475.
[9]Bode A M,Dong Z G.The two faces of capsaicin[J].Cancer Research,2011,71(8):2809-2814.
[10]Bley K,Boorman G,Mohammad B,et al.A comprehensive review of the carcinogenic and anticarcinogenic potential of capsaicin[J].Toxicolgic Pathology,2012,40:847-873.
[11]Lee E J,Jeon M S,Kim B D,et al.Capsiate inhibits ultraviolet B-induced skin inflammation by inhibiting Src family kinases and epidermal growth factor receptor signaling[J].Free Radical Biology&Medicine,2010,48:1133-1143.
[12]Frydas S,Varvara G,Murmura G,et al.Impact of capsaicin on mast cell inflammation[J].International Journal of Immunop-athology and Pharmacology,2013,26(3):597-600.
[13]Pan Yongping(潘永萍),Jiang Xiaohui(姜晓辉),Yu Liangmin(于良民).Synthesis of benzamide derivatives containing capsaicin with active structure and their bacteriostatic activity and antifouling capability[J].Fine Chemicals(精细化工),2014,31(1):7-11.
[14]Zhang Xiaochun(张晓春),Yu Liangmin(于良民),Jiang Xiaohui(姜晓辉).Synthesis,bacterioststic and anti-alga capability of monomers and polymers containing capsaicin[J].Materials Review B:Research Paper(材料导报B:研究篇),2018,32(1):194-202.
[15]Zheng Shaojun(郑绍军),Wang Yu(王瑜),Zhu Rui(朱瑞),et al.Recent research progress of synthetic substances as antifoulants[J].Journal of Chinese Society for Corrosion and Protection(中国腐蚀与防护学报),2016,36(5):390-397.
[16]Zhang Ran(张然),Li Biao(李彪),Wei Yong(韦勇),et al.Study on the antimicrobial activity of natural capsaicin on some phytopathogen[J].Hubei Agricultural Science(湖北农业科学),2018,57(8):66-69.
[17]Jiang Xiaohui(姜晓辉),Pan Yongping(潘永萍),Cong Weiwei(丛巍巍),et al.Synthesis,bacteriostasic activity activityand antifouling capability of dibenzamides containing capsaicin moietie[J].Periodical of Ocean University of China(中国海洋大学学报),2018,48(2):79-84.
[18]Han Yongping(韩永萍),Gong Ping(龚平),Li Keyi(李可意).Study on antibacterial activity of phenol hydroxyl from N-aryl Schiff COSderivatives[J].Food&Machinery(食品与机械),2015,31(1):127-131.
[19]Pernak J,Rogo?a J,Mirska I.Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides[J].European Journal of Medicinal Chemistry,2001,36(4):313-320.
[20]Bodor N.Soft drugs.1.Liable quaternary ammonium salts as soft antimicrobials[J].Journal of Medidnal Chemistry,1980,23(50):469-474.
[21]Klancnik A,Piskernik S,Jersek B,et al.Evaluation of diffusion and dilution methods to determine the antibacterial activity of plant extracts[J].Journal of Microbiological Methods,2010,81(2):121-126.
[22]Sun Haijing(孙海静),Gao Xueli(高学理),Wang Jian(王剑),et al.Preparation and characterization of antifouling and bacteriostatic polyamide nanofiltration membrane[J].Periodical of Ocean University of China(中国海洋大学学报),2017,47(5):88-93.
[23]Wang Xue(王雪),Xu Jia(徐佳),Jiang Yuye(蒋钰烨),et al.Preparation and properties of new antibacterial polysulfone ultrafiltration membranes[J].Chemical Journal of Chinese Universities(高等学校化学学报),2012,33(9):2129-2134.
[24]Zhang Yunling(张云玲),Zheng Yimin(郑一敏),Hu Shaonan(胡少南),et al.Anti-Helicobacter pylori effect of 6-gingerol in vitro[J].Modern Food Science and Technology(现代食品科技),2013,29(6):1259-1305.
[25]Feng Wen(冯文),Wang Xianghui(王向辉),Song Huangwang(宋煌旺),et al.Syntheses and QSAR study on anti-algae activities of benzisothiazolin-3-one derivatives[J].Chemistry(化学通报),2017,80(12):1133-1147.
[26]Wang Jin(汪瑾),Du Mingyong(杜明勇),Yu Yufeng(于玉凤),et al.The inhibitory effect of plant extracts on Microcystis aeruginosa and its algal inhibiting characteristics[J].Journal of Nanjing Agricultural University(南京农业大学学报),2014,37(4):91-94.
[27]Zhong Yunxiao(种云霄),Tang Zhongen(汤仲恩),Yu Guangwei(余光伟),et al.Growth inhibition of blue-green algae by submerged macrophytes culture solutions with existence of the low level of copper ion[J].Ecology and Environmental Sciences(生态环境学报),2012,21(9):1594-1598.
[28]Xu Huanzhi(徐焕志),Yu Liangmin(于良民),Li Changcheng(李昌诚),et al.Synthesis of acrylamides containing capsaicin derivative moiety and their growth inhibition against Nitzschia closterium[J].Chinese Journal of Applied Chemistry(应用化学),2007,24(8):911-916.