•  
  •  
 

Abstract

This study investigated the inhibitory effects of p-coumaric acid, ferulic acid and feruloylated oligosaccharides on catalytic activities of tyrosinase by analysising tyrosinase steady state activity and enzyme kinetics. The results showed that the three compounds were found to efficiently inhibit tyrosinase monophenolase activities. The p-Coumaric acid was the strongest inhibitor followed by feruloylated oligosaccharides and ferulic acid, with the IC50 value of 0.75, 3.20, 9.30 mmol/L respectively. Moreover, p-coumaric acid and ferulic acid were found to inhibit the activities of diphenolase with IC50 value of 4.3, 12.7 mmol/L respectively; however, feruloylated oligosaccharides showed no inhibitory effect on diphenolase activity. p-Coumaric acid increased the lag time of monophenolase activity, but ferulic acid showed little effect; while feruloylated oligosaccharides reduced the lag time of monophenolase activity. Enzyme kinetics analysis indicated that p-coumaric acid is a competitive inhibitor of the monophenolase, while ferulic acid and feruloylated oligosaccharides showed a mixed inhibitory effect.

Publication Date

11-28-2016

First Page

9

Last Page

12,63

DOI

10.13652/j.issn.1003-5788.2016.11.002

References

[1] KANTEEV M, GOLDFEDER M, FISHMAN A. Tyrosinase: Structure-function correlations in tyrosinases[J]. The Prorein Society, 2015, 24(9): 1 360-1 369.
[2] LEE S Y, BAEK N, NAM T G. Natural, semisynthetic and synthetic tyrosinase inhibitors[J]. Journal of Enzyme Inhibtion and Medicinal Chemistey, 2016, 31(1): 1-13.
[3] CHANG Te-sheng. An updated review of tyrosinase[J]. International Journal of Molecular Sciences, 2009, 10(6): 2 440-2 475.
[4] PEI Ke-han, OU Juan-ying, HUANG Jun-qing, et al. p-Coumaric acid and its conjugates: dietarysources, pharmacokinetic propertiesand biological activities[J]. Journal of the Science of Food and Agriculture, 2016, 96(9): 2 952-2 962.
[5] PEI Ke-han, OU Juan-ying, HUANG Cai-huan, et al. Derivatives of ferulic acid: Structure, preparation and biological activities[J]. Annual Research & Review in Biology, 2015, 5(6): 512-528.
[6] YAO Sheng-wen, WEN Xiao-xiao, HUANG Ru-qing, et al. Protection of feruloylated oligosaccharides from corn bran against oxidative stress in PC 12 cells[J]. Journal of Agriculture and Food Chemistry, 2014, 62(3): 668-674.
[7] 刘晓丹, 黄璜, 陈清西. 苯甲酸对蘑菇酪氨酸酶抑制作用机理的研究[J]. 厦门大学学报, 2003, 42(1): 102-106
[8] CUI Yi, LIANG Ge, HU Yong-hua, et al. Alpha-Substituted derivatives of cinnamaldehyde as tyrosinase inhibitors: Inhibitory mechanism and molecular analysis[J]. Journal of Agriculture and Food Chemistry, 2015, 63(2): 716-722.
[9] AN S M, KOH J S, BOO Y C. p-Coumaricacid not only inhibits human tyrosinase activity in vitro but also melanogenesis in cells exposed to UVB [J]. Phytotherapy Research, 2010, 24(8): 1 175-1 180.
[10] SANCHEZ F A, RODRIGUEZ J N, GARCIA C F. Tyrosinase: A comprehensive review of its mechanism[J]. Biechem Biophys Aeta, 1995, 1 247(1): 1-11.
[11] RAMSDEN C A, RILEY P A. Tyrosinase: The four oxidation states of the active site and theirrelevance to enzymatic activation, oxidation and inactivationitors[J]. Bioorganic & Medicinal Chemistry, 2014, 22(8): 2 388-2 395.
[12] LIN Qi-ling, OU Shi-yi, WEN Qi-biao. In vitro antioxidant activity of feruloyl arabinose isolated from maize bran by acid hydrolysis[J]. Journal of Food Science and Technology, 2014, 51(7): 1 356-1 362.
[13] 陈清西, 林建峰, 宋康康. 酪氨酸酶抑制剂的研究[J]. 厦门大学学报, 2007, 46(2): 274-282.
[14] 郑穗平, 郭勇, 潘力. 酶学[M]. 北京: 科学出版社, 2009: 106-117.
[15] DECKER H, SCHWEIKARDT T, TUCZEK F. The rst crystal structure of tyrosinase: all questions answered?[J]. Angewandte Chemie International Edition, 2006, 45(28): 4 546-4 550.
[16] OU Juan-ying, SUN Zheng. Feruloylated oligosaccharides:Stucture, metabolism and function[J]. Journal of Functional Foods, 2014, 7: 90-100.

Share

COinS
 
 

To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.