咖啡酸酯类和酰胺类衍生物的合成和应用研究进展
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摘要
咖啡酸是一种天然(种子、咖啡、果蔬)来源的酚酸类活性物质,在药物化学、化妆品、食品等领域有较为广泛的应用,关于咖啡酸衍生物的合成和应用研究受到了研究者们的广泛关注,本文综述了近年来咖啡酸酯类和酰胺类衍生物合成及应用的研究新进展。
Caffeic acid, which was found in seeds, coffee, fruits and vegetables, is a natural source of phenolic acid active substances. Caffeic acid has a wide range of applications in the fields of medicinal chemistry, cosmetics,food, etc. The research on the synthesis and application of derivatives of caffeic acid has received extensive atten-tion. This paper reviews recent advances in the synthesis and application of caffeic acid esters and caffeic acid amide derivatives.
Caffeic acid, which was found in seeds, coffee, fruits and vegetables, is a natural source of phenolic acid active substances. Caffeic acid has a wide range of applications in the fields of medicinal chemistry, cosmetics,food, etc. The research on the synthesis and application of derivatives of caffeic acid has received extensive atten-tion. This paper reviews recent advances in the synthesis and application of caffeic acid esters and caffeic acid amide derivatives.
引文
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[10]DE CAMPOS BUZZI F,FRANZOI C L,ANTONINI G,et al.Antinociceptive properties of caffeic acid derivatives in mice[J].European Journal of Medicinal Chemistry,2009,44(11):4596-4602.
[11]XIE J,YANG F,ZHANG M,et al.Antiproliferative Activity and SARs of Caffeic Acid Esters with Mono-substituted Phenylethanols Moiety[J].Bioorganic&Medicinal Chemistry Letters,2016,27(2):131.
[12]SANDERSON J T,CLABAULT H,PATTON C,et al.Antiproliferative,antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells[J].Bioorganic&Medicinal Chemistry,2013,21(22):7182-7193.
[13]MOOSAVI F,HOSSEINI R,RAJAIAN H,et al.Derivatives of caffeic acid,a natural antioxidant,as the basis for the discovery of novel nonpeptidic neurotrophic agents[J].Bioorganic&Medicinal Chemistry,2017,25(12):S0968089617302146.
[14]SINGH P,SINGH GREWAL A,PANDITA D,et al.Synthesis and evaluation of a series of caffeic acid derivatives as anticancer agents[J].Future Journal of Pharmaceutical Sciences,2018,4(2):124-130.
[15]XIE Y,BING H,YU K,et al.Caffeic acid derivatives:A new type of influenza neuraminidase inhibitors[J].Bioorganic&Medicinal Chemistry Letters,2013,23(12):3556-3560.
[16]XIE Y,HUANG B,YU K,et al.Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors[J].Bioorganic&Medicinal Chemistry,2013,21(24):7715-7723.
[17]JO H,ZHOU Y,VIJI M,et al.Synthesis,biological evaluation,and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of l±-MSH-stimulated melanogenesis[J].Bioorganic&Medicinal Chemistry Letters,2017,27(21).
[18]BENCHEKROUN M,PACH N-ANGONA I,LUZET V,et al.Synthesis,antioxidant and Aβanti-aggregation properties of new ferulic,caffeic and lipoic acid derivatives obtained by the Ugi fourcomponent reaction[J].Bioorganic Chemistry,2019,85:221-228.
[2]杨九凌,祝晓玲,李成文,等.咖啡酸及其衍生物咖啡酸苯乙酯药理作用研究进展[J].中国药学杂志,2013,48(8):577-581.
[3]范金波,蔡茜彤,冯叙桥,等.咖啡酸体外抗氧化活性的研究[J].中国食品学报,2015,15(3):65-73.
[4]朱敏,王芳权.咖啡酸等羟基肉桂酸化合物抗氧化性能的测定及评估[J].食品工业科技,2004,(9):74-74.
[5]BASSIL D,MAKRIS D P,KEFALAS P.Oxidation of caffeic acid in the presence of l-cysteine:isolation of 2-S-cysteinylcaffeic acid and evaluation of its antioxidant properties[J].Food Research International,2005,38(4):395-402.
[6]LIAO C C,OU T T,WU C H,et al.Prevention of diet-induced hyperlipidemia and obesity by caffeic acid in C57BL/6 mice through regulation of hepatic lipogenesis gene expression[J].Journal of A-gricultural&Food Chemistry,2013,61(46):11082-11088.
[7]ALMAJANO M P,CARB R,DELGADO M E,et al.Effect of pH on the antimicrobial activity and oxidative stability of oil-in-water emulsions containing caffeic acid[J].Journal of Food Science,2010,72(5):C258-C263.
[8]LIN C L,CHEN R F,CHEN Y F,et al.Protective Effect of Caffeic Acid on Paclitaxel Induced Anti-Proliferation and Apoptosis of Lung Cancer Cells Involves NF-κB Pathway[J].International Journal of Molecular Sciences,2012,13(5):6236-6245.
[9]DANIELA D V,LAURA F,FELICIA DIODATA D A,et al.Activity of caffeic acid derivatives against Candida albicans biofilm[J].Bioorganic&Medicinal Chemistry Letters,2014,24(6):1502-1505.
[10]DE CAMPOS BUZZI F,FRANZOI C L,ANTONINI G,et al.Antinociceptive properties of caffeic acid derivatives in mice[J].European Journal of Medicinal Chemistry,2009,44(11):4596-4602.
[11]XIE J,YANG F,ZHANG M,et al.Antiproliferative Activity and SARs of Caffeic Acid Esters with Mono-substituted Phenylethanols Moiety[J].Bioorganic&Medicinal Chemistry Letters,2016,27(2):131.
[12]SANDERSON J T,CLABAULT H,PATTON C,et al.Antiproliferative,antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells[J].Bioorganic&Medicinal Chemistry,2013,21(22):7182-7193.
[13]MOOSAVI F,HOSSEINI R,RAJAIAN H,et al.Derivatives of caffeic acid,a natural antioxidant,as the basis for the discovery of novel nonpeptidic neurotrophic agents[J].Bioorganic&Medicinal Chemistry,2017,25(12):S0968089617302146.
[14]SINGH P,SINGH GREWAL A,PANDITA D,et al.Synthesis and evaluation of a series of caffeic acid derivatives as anticancer agents[J].Future Journal of Pharmaceutical Sciences,2018,4(2):124-130.
[15]XIE Y,BING H,YU K,et al.Caffeic acid derivatives:A new type of influenza neuraminidase inhibitors[J].Bioorganic&Medicinal Chemistry Letters,2013,23(12):3556-3560.
[16]XIE Y,HUANG B,YU K,et al.Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors[J].Bioorganic&Medicinal Chemistry,2013,21(24):7715-7723.
[17]JO H,ZHOU Y,VIJI M,et al.Synthesis,biological evaluation,and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of l±-MSH-stimulated melanogenesis[J].Bioorganic&Medicinal Chemistry Letters,2017,27(21).
[18]BENCHEKROUN M,PACH N-ANGONA I,LUZET V,et al.Synthesis,antioxidant and Aβanti-aggregation properties of new ferulic,caffeic and lipoic acid derivatives obtained by the Ugi fourcomponent reaction[J].Bioorganic Chemistry,2019,85:221-228.