Journal of Food and Nutrition Research
ISSN (Print): 2333-1119 ISSN (Online): 2333-1240 Website: https://www.sciepub.com/journal/jfnr Editor-in-chief: Prabhat Kumar Mandal
Open Access
Journal Browser
Go
Journal of Food and Nutrition Research. 2014, 2(10), 698-703
DOI: 10.12691/jfnr-2-10-8
Open AccessArticle

Inhibitory Mechanism of Salidroside on Tyrosinase

Yaxin Zhu1, Chaoyin Chen1, , Shenglan Zhao2, , Jiong Yang1, Hao Song1, Feng Ge1 and Diqiu Liu1

1Faculty of life science, Kunming University of Science and Technology, Kunming, Yunnan, China

2Yunnan University of Traditional Chinese Medicine, Kunming, Yunnan, China

Pub. Date: September 26, 2014

Cite this paper:
Yaxin Zhu, Chaoyin Chen, Shenglan Zhao, Jiong Yang, Hao Song, Feng Ge and Diqiu Liu. Inhibitory Mechanism of Salidroside on Tyrosinase. Journal of Food and Nutrition Research. 2014; 2(10):698-703. doi: 10.12691/jfnr-2-10-8

Abstract

Tyrosinase is a key rate-limiting enzyme in melanin synthesis which can be blocked to reduce melasma and freckles by inhibiting the activity of tyrosinase. Salidroside showed certain inhibitory effects on tyrosinase by enzyme kinetics with inhibition of 33.04%. Besides it was also a competitive inhibitor of tyrosinase which served as a substrate analogue to combine with enzyme to produce quinones with stronger light absorption. Furthermore, docking results implied that inhibitory mechanisms might be attributed to the weak interactions between salidroside and tyrosinase such as hydrogen bonds and van del waals. Salidroside is a main kind of plant flavonoids from Rhodiola rosea, walnut and so on. Studying inhibitory mechanism of salidroside on tyrosinase is not only helpful for developing anti-freckle products in which salidroside is one of the most important components, but also beneficial for making better use of plant flavonoids to seek for a new generation of natural skin care cosmetics.

Keywords:
tyrosinase salidroside inhibitor mechanism flavonoid

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

Figures

Figure of 6

References:

[1]  Ryu YB, W IM, Kang NS, Kim HY, Kim JH, Moon YH, Park KH: Kurarinol, tyrosinase inhibitor isolated from the root of Sophora flavescens. Phytomedicine 2008, 15(8): 612-618.
 
[2]  Kang Y, Choi JU, Lee EA, Park HR: Flaniostatin, a new flavonoid glycoside isolated from the leaves of Cudrania tricuspidata as a tyrosinase inhibitor. Food Sci Biotechnol 2013, 22(5): 1449-1452.
 
[3]  Yamaguchi Y, Brenner M, Hearing VJ: The regulation of skin pigmentation. J Biol Chem 2007, 282(38): 27557-27561.
 
[4]  Eller MS, Ostrom K, Gilchrest BA: DNA damage enhances melanogenesis. P Natl Acad Sci USA 1996, 93(3): 1087-1092.
 
[5]  Ortonne JP: Photoprotective properties of skin melanin. Brit J Dermatol 2002, 146(s61): 7-10.
 
[6]  Kim YJ, No JK, Lee JH, Chung HY: 4,4'-Dihydroxybiphenyl as a new potent tyrosinase inhibitor. Biol Pharm Bull 2005, 28(2): 323-327.
 
[7]  Gawande SS, Warangkar SC, Bandgar BP, Khobragade CN: Synthesis of new heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds as potent inhibitors of tyrosinase. Bioorgan Med Chem 2013, 21(10): 2772-2777.
 
[8]  Lou SN, Yu MW, Ho CT: Tyrosinase inhibitory components of immature calamondin peel. Food Chem 2012, 135(3): 1091-1096.
 
[9]  Kim YJ, Uyama H: Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 2005, 62(15): 1707-1723.
 
[10]  Lin YF, Hu YH, Lin HT, Liu X, Chen YH, Zhang S, Chen QX: Inhibitory effects of propyl gallate on tyrosinase and its application in controlling pericarp browning of harvested longan fruits. J Agr Food Chem 2013, 61(11): 2889-2895.
 
[11]  Chang TS: An updated review of tyrosinase inhibitors. Int J Mol Sci 2009, 10(6): 2440-2475.
 
[12]  Solano F, Briganti S, Picardo M, Ghanem G: Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigm Cell Res 2006, 19(6): 550-571.
 
[13]  Kondo T, Hearing VJ: Update on the regulation of mammalian melanocyte function and skin pigmentation. Expert Rev Dermatol 2011, 6(1): 97-108.
 
[14]  Lim YJ, Lee EH, Kang TH, Ha SK, Oh MS, Kim SM, Yooh TJ, Kang CH, Park JH, Kim SY: Inhibitory effects of arbutin on melanin biosynthesis of ɑ-melanocyte stimulating hormone-induced hyperpigmentation in cultured brownish guinea pig skin tissues. Arch Pharm Res 2009, 32(3): 367-373.
 
[15]  Cabanes J, Chazarra S, Garcia-Carmona F: Kojic Acid, a Cosmetic Skin Whitening Agent, is a Slow-binding Inhibitor of Catecholase Activity of Tyrosinase. J Pharm Pharmacol 1994, 46(12): 982-985.
 
[16]  Briganti S, Camera E, Picardo M: Chemical and instrumental approaches to treat hyperpigmentation. Pigm Cell Res 2003, 16(3): 101-110.
 
[17]  Kim KS, Kim JA, Eom SY, Lee SH, Min KR, Kim Y: Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression. Pigm Cell Res 2006, 19(1): 90-98.
 
[18]  Nakayama T, Sato T, Fukui Y, Yonekura-Sakakibara K, Hayashi H, Tanaka Y, Kusumi T, Nishino T: Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration. FEBS Letters 2001, 499(1): 107-111.
 
[19]  Lin J, Chiang H, Lin Y, Wen K: Natural products with skin-whitening effects. J Food Drug Anal 2008, 16(2): 1-10.
 
[20]  Peng LH, Liu S, Xu SY, Chen L, Shan YH, Wei W, Liang WQ, Gao JQ: Inhibitory effects of salidroside and paeonol on tyrosinase activity and melanin synthesis in mouse B16F10 melanoma cells and ultraviolet B-induced pigmentation in guinea pig skin. Phytomedicine 2013, 20(12): 1082-1087.
 
[21]  Chen SF, Tsai HJ, Hung TH, Chen CC, Lee CY, Wu CH, Wang PY, Liao NC: Salidroside improves behavioral and histological outcomes and reduces apoptosis via PI3K/Akt signaling after experimental traumatic brain injury. Plos One 2012, 7(9): e45763.
 
[22]  Liu CY, Tai ZG, Feng SQ, Fang YS, Cai L, Ding ZT: Chemical constituents from the seed coat of Juglans regia. China. J Chin Mater Med 2012, 37(10): 18.
 
[23]  Calcabrini C, De Bellis R, Mancini U, Cucchiarini L, Potenza L, De Sanctis R, Patrone V, Scesa C, Dachà M: Rhodiola rosea ability to enrich cellular antioxidant defences of cultured human keratinocytes. Arch Dermatol Res 2010, 302(3): 191-200.
 
[24]  Kang HS, Kim HR, Byun DS, Son BW, Nam TJ, Choi JS: Tyrosinase inhibitors isolated from the edible brown algaEcklonia stolonifera. Arch Pharm Res 2004, 27(12): 1226-1232.
 
[25]  Kucinskaite A, Briedis V, Savickas A: Experimental analysis of therapeutic properties of Rhodiola rosea L. and its possible application in medicine. Med 2003, 40(7): 614-619.
 
[26]  Zhong H, Xin H, Wu LX, Zhu YZ: Salidroside attenuates apoptosis in ischemic cardiomyocytes: a mechanism through a mitochondria-dependent pathway. J Pharmacol Sci 2009, 114(4): 399-408.
 
[27]  Momtaz S, Lall N, Basson A: Inhibitory activities of mushroom tyrosine and DOPA oxidation by plant extracts. S Afr J Bot 2008, 74(4): 577-582.
 
[28]  Mu Y, Li L, Hu SQ: Molecular inhibitory mechanism of tricin on tyrosinase. Spectrochim Acta A 2003, 107(15): 235-240.
 
[29]  Xie LP, Chen QX, Huang H, Wang HZ, Zhang RQ: Inhibitory effects of some flavonoids on the activity of mushroom tyrosinase. Biochemistry (Moscow) 2003, 68(4): 487-491.
 
[30]  Kubo I, Kinst-Hori I: Flavonols from saffron flower: tyrosinase inhibitory activity and inhibition mechanism. J Agr Food Chem 1999, 47(10): 4121-4125.
 
[31]  Kim D, Park J, Kim J, Han C, Yoon J, Kim N, Seo J, Lee C: Flavonoids as mushroom tyrosinase inhibitors: a fluorescence quenching study. J Agr Food Chem 2006, 54(3): 935-941.
 
[32]  Trott O, Olson AJ: AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010, 31(2): 455-461.
 
[33]  Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, Sugiyama M: Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem 2006, 281(13): 8981-8990.
 
[34]  Kubo I, Nihei K, Tsujimoto K: Methy p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells. Bioorg Med Chem 2004, 12(20): 5349-5354.
 
[35]  Kim D, Park J, Kim J, Han C, Yoon J, Kim N, Seo J, Lee C: Flavonoids as mushroom tyrosinase inhibitors: a fluorescence quenching study. J Agr Food Chem 2006, 54(3): 935-941.
 
[36]  Si YX, Yin SJ, Oh S, Wang ZJ, Ye S, Yan L, Yang JM, Park YD, Lee J, Qian GY: An integrated study of tyrosinase inhibition by rutin: progress using a computational simulation. J Biomol Struct Dyn 2012, 29(5): 999-1012.