十一碳烯酰基苯丙氨酸的合成及其抑制酪氨酸酶二酚酶活性的研究

doi:10.13218/j.cnki.csdc.2016.10.009

日用化学工业 ›› 2016, Vol. 46 ›› Issue (10): 591-595.doi: 10.13218/j.cnki.csdc.2016.10.009

十一碳烯酰基苯丙氨酸的合成及其抑制酪氨酸酶二酚酶活性的研究

徐凯,许虎君

江南大学化工与材料工程学院,江苏无锡 214122

出版日期:2016-10-22 发布日期:2019-04-18
通讯作者: 许虎君,副教授,博士,电话:13338103707,E-mail:xu6209@163.com。
作者简介:徐凯(1991-),男,江苏人,硕士,电话:18762670225,E-mail:xukaijiangnan@163.com。

Synthesis and inhibitory effect on tyrosinase diphenolase activity of N-undecenoyl-L-phenylalanine

XU Kai,XU Hu-jun

School of Chemical &Material Engineering,Jiangnan University,Wuxi,Jiangsu 214122,China

Online:2016-10-22 Published:2019-04-18

摘要/Abstract

摘要： 以十一烯酸和苯丙氨酸为原料,使用氯化亚砜将十一烯酸酰氯化,采用肖顿-鲍曼法(Schotten-Baumann)缩合反应合成了十一碳烯酰基苯丙氨酸钠,再经酸化分离后得到了十一碳烯酰基苯丙氨酸。利用IR,MS和¹H NMR对合成产物的结构进行了表征,同时考察了十一碳烯酰基苯丙氨酸对酪氨酸酶二酚酶活性抑制的机制。结果表明,十一碳烯酰基苯丙氨酸对酪氨酸酶二酚酶活性的抑制作用为竞争性可逆抑制,其半抑制浓度为3.711 g/L,抑制常数(K_i)为3.651 g/L。

关键词: 美白化妆品添加剂, 十一碳烯酰基苯丙氨酸, 酪氨酸酶抑制剂, 竞争性可逆抑制

Abstract: Undecylenic acid and L-phenylalanine were used as main materials to prepare N-undecenoyl-L-phenylalanine.The undecylenic acid was acyl-chlorinated with thionyl chloride via Schotten-Baumann reaction,followed by acidification;then the target product,N-undecenoyl-L-phenylalanine was obtained.The product was characterized by IR,MS and ¹H NMR.Meanwhile,the mechanism for inhibitory effect on tyrosinase diphenolase activity of N-undecenoyl-L-phenylalanine was investigated.Results showed that the inhibitory effect on tyrosinase diphenolase activity of N-undecenoyl-L-phenylalanine is competitive and reversible inhibition.Its 50% effective inhibitory concentration is 3.711 g/L,and its inhibition constant (K_i) is 3.651 g/L.

Key words: additives of whitening cosmetics, N-undecenoyl-L-phenylalanine, tyrosinase inhibitor, competitive and reversible inhibition

中图分类号:

TQ658

徐凯,许虎君. 十一碳烯酰基苯丙氨酸的合成及其抑制酪氨酸酶二酚酶活性的研究[J]. 日用化学工业, 2016, 46(10): 591-595.

XU Kai,XU Hu-jun. Synthesis and inhibitory effect on tyrosinase diphenolase activity of N-undecenoyl-L-phenylalanine[J]. China Surfactant Detergent & Cosmetics, 2016, 46(10): 591-595.

参考文献

[1] SLOMINSKI,TOBIN D J,SHIBAHARA S.Melanin pigmentation in mammalian skin and its hormonal regulation [J] .Physiological Reviews,2004,84:1155-1228.
[2] GODING C R.Melanocytes:the new Black [J] .The International Journal of Biochemistry & Cell Biology,2007,39:275-279.
[3] CHEN Q X,KUBO I.Kinetics of mushroom tyrosinase inhibition by quercetin [J] .Journal of Agricultural and Food Chemistry,2002,50:4108-4112.
[4] MAEDA K,FUKUDA M.Arbutin:mechanism of its depigmenting action in humanmelanocyte culture [J] .Journal of Pharmacology and Experimental Therapeutics,1996,276:765-769.
[5] NIHEI K,KUBO I.Identification of oxidation product of arbutin in mushroomtyrosinase assay system [J] .Bioorganic & Medicinal Chemi-stry Letters,2003,13:2409-2412.
[6] MAEDA L,YOSHIZAKI K.Intestinal term pregnancy without rupture [J] .Nippon SankaFujinka Gakkai Zasshi,1991,43:361-363.
[7] SEO S Y,SHARMA V K,SHARMA N.Mushroom tyrosinase:recent prospects [J] .Journal of Agricultural and Food Chemistry,2003,51:2837-2853.
[8] CORINNE S,CHRISTINE G.Use of a compound inactivating the kinase a protein in a composition containg a cosmetically acceptable medium in order to lighten the skin:US2005118119(A1)[P] .2005-06-02.
[9] JUNGERMANN E,KREMS I J.The preparation of long chain N-acylamino acids [J] .Journal of the American Chemical Society,1956,78(3):172-174.
[10] SINIAWSKI M T,SANIEI N,ADHIKARI B,et al.Influence of fatty acid composition on the tribological performance of two vegetable-based lubricants [J] .Journal of Synthetic Lubrication,2007,24(2):101-110.
[11] CHEN Q,KUBO I.Kinetics of mushroom tyrosinase inhibition by quercetin [J] .Journal of Agricultural and Food Chemistry,2002,50(14):4108-4112.
[12] XIE L P,CHEN Q X,HUANG H,et al.Inhibitory effects of cupferron on the monophenolase and diphenolase activity of mushroom tyrosinase [J] .International Journal of Biochemistry & Cell Biology,2003,35(12):1658-1666.
[13] CHEN Q X,SONG K K,WANG Q,et al.Inhibitory effects of hexyl-resorcinol and dodecyleresorcinol on mushroom (Agrices bisporus) tyrosinase [J] .Protein Journal,2004,23(2):135-141.

十一碳烯酰基苯丙氨酸的合成及其抑制酪氨酸酶二酚酶活性的研究

Synthesis and inhibitory effect on tyrosinase diphenolase activity of N-undecenoyl-L-phenylalanine

PDF (PC)

赞

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 9

Metrics

本文评价

推荐阅读 10

[1]	郑曦,陈智多,张德蒙,秦益民,易彩霞,黄啸. 海藻酸钠对酪氨酸酶的抑制作用[J]. 日用化学工业, 2019, 49(6): 388-392.
[2]	郝谜谜, 王艳, 刘园园, 鲍炎, 李红艳, 郑琳. 苯乙基间苯二酚抑制黑色素形成的机理研究[J]. 日用化学工业, 2018, 48(5): 293-298.
[3]	孙劲毅, 蔡春辉, 梁蓉, 杨成. 茶皂素的纯化及抑制酪氨酸酶活性的研究[J]. 日用化学工业, 2017, 47(6): 312-316.
[4]	陈宇霞, 张凯, 龚盛昭. 茯苓提取物对酪氨酸酶抑制动力学及刺激性研究[J]. 日用化学工业, 2017, 47(6): 317-321.
[5]	李倩, 李晨阳, 詹羽娇, 买吾拉江·阿不都热衣木, 徐芳, 赵军. 睡莲花提取物对酪氨酸酶的抑制作用及其动力学研究[J]. 日用化学工业, 2017, 47(4): 219-222.
[6]	罗碧, 李国柱, 王立军, 孟庆艳, 卢亚玲, 刘文杰. 薰衣草花提取物对酪氨酸酶的抑制作用研究[J]. 日用化学工业, 2015, 45(2): 90-93.
[7]	李杨, 杨子佳, 祝钧, 董银卯. 壬二酸的化学改性及产物抑制酪氨酸酶活性的研究[J]. 日用化学工业, 2014, 44(9): 494-496.
[8]	杨培, 张逸伟. 曲酸金属配合物的合成与酪氨酸酶抑制性能研究[J]. 日用化学工业, 2014, 44(12): 688-691.
[9]	付建红, 祁瑞, 郑静, 周晨婕, 陈清西. 桑叶黄酮抑制酪氨酸酶活性的动力学研究[J]. 日用化学工业, 2014, 44(10): 564-567.