Citation: JIN Yuting, ZHI Defu, GUO Yongtai, SUI Yue, SUN Lei, ZWANG Qian, HAO Longxuan, ZHAO Chunhui. Whitening and Antioxidant Activities of Phenolic Derivatives[J]. Chinese Journal of Applied Chemistry, ;2019, 36(11): 1257-1265. doi: 10.11944/j.issn.1000-0518.2019.11.190139 shu

Whitening and Antioxidant Activities of Phenolic Derivatives

JIN Yuting ^a ,
ZHI Defu ^c ,
GUO Yongtai ^a ,
SUI Yue ^a ,
SUN Lei ^a ,
ZWANG Qian ^a ,
HAO Longxuan ^a,b,, ,
ZHAO Chunhui ^b,,

a.
Liaoning Normal University, School of Chemistry and Chemical Engineering, Dalian, Liaoning 116029, China
b.
Liaoning Normal University Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Dalian, Liaoning 116029, China
c.
Dalian Nationalities University College of Life Science, Dalian, Liaoning 116600, China

Corresponding author: HAO Longxuan, lxzhao@lnnu.edu.cn ZHAO Chunhui, zch@lnnu.edu.cn
Received Date: 14 May 2019
Revised Date: 23 July 2019
Accepted Date: 19 August 2019

Fund Project: Supported by the National Natural Science Foundation of China(No.21101067)the National Natural Science Foundation of China 21101067

Figures(1)

A series of phenolic derivatives was synthesized and characterized by Fourier transform infrared spectrometer(FTIR), nuclear magnetic resonance spectroscopy(NMR) and electrospray ionisation mass spectrometry(ESI-MS). Their whitening activity was also tested. The results showed that the tyrosinase inhibitory activities HB-1(0.229±0.026), HB-3a(0.829±0.135), HB-3b(0.446±0.047), HMB-3a(1.747±0.215), HMB-3b(1.307±0.058) and HPE-4b(2.501±0.261) were significantly better than those of the positive control, α-arbutin (3.60±0.029). The antioxidant activities of these compounds were tested to whitening potentials. The results showed that the antioxidant activities of HB-3b and HMB-3a were comparable to the positive control substance quercetin and lycopene. Therefore, such compounds can be developed and utilized as whitening agents and antioxidants.>
- penolic compounds,
- tyrosinase inhibitor,
- anti-oxidant
1. [1]
  Lee T H, Seo J O, Do M H. Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue[J]. Biomol Ther, 2014,22(5):431-437. doi: 10.4062/biomolther.2014.098
2. [2]
  Garcia-Jimenez A, Teruel-Puche J A, Berna J. Action of Tyrosinase on Alpha and Beta-Arbutin:A Kinetic Study[J]. Plos One, 2017,12(5)e0177330. doi: 10.1371/journal.pone.0177330
3. [3]
  Kazuhisa S, Takahisa N, Koji N. Syntheses of Arbutin-Aglycosides and a Comparison of Their Inhibitory Effects with Those of α-Arbutin and Arbutin on Human Tyrosinase[J]. Chem Pharm Bull, 2003,51(7):798-801. doi: 10.1248/cpb.51.798
4. [4]
  Hassan M, Ashraf Z, Abbas Q. Exploration of Novel Human Tyrosinase Inhibitors by Molecular Modeling, Docking and Simulation Studies[J]. Interdiscip Sci, 2016,10(1):1-13.
5. [5]
  Kim J, Kang S, Kwon H. Dual Functional Bioactive-Peptide, AIMP1-Derived Peptide(AdP), for Anti-aging[J]. J Cosmet Dermatol-US, 2018,18(1):251-257.
6. [6]
  Hung V, Ph am. Phenolic Compounds of Cereals and Their Antioxidant Capacity[J]. Crit Rev Food Sci, 2016,56(1):25-35. doi: 10.1080/10408398.2012.708909
7. [7]
  Wen K C, Chang C S, Chien Y C. Tyrosol and Its Analogues Inhibit Alpha-melanocyte-stimulating Hormone Induced Melanogenesis[J]. Int J Mol Sci, 2013,14(12):23420-23440. doi: 10.3390/ijms141223420
8. [8]
  Bhutto A A, Kalay S, Sherazi S T H. Quantitative Structure-Activity Relationship Between Antioxidant Capacity of Phenolic Compounds and the Plasmonic Properties of Silver Nanoparticles[J]. Talanta, 2018,189:174-181. doi: 10.1016/j.talanta.2018.06.080
9. [9]
  Kosieradzki M, Rowiński W. Ischemia/Reperfusion Injury in Kidney Transplantation:Mechanisms and Prevention[J]. Transpl Proc, 2008,40(10):3279-3288. doi: 10.1016/j.transproceed.2008.10.004
10. [10]
  Kaulmann A, Bohn T. Bioactivity of Polyphenols:Preventive and Adjuvant Strategies Toward Reducing Inflammatory Bowel Diseases-Promises, Perspectives, and Pitfalls[J]. Oxid Med Cell Longev, 2016,2016:1-29.
11. [11]
  Chen W, Zhang Z, Shen Y. Effect of Tea Polyphenols on Lipid Peroxidation and Antioxidant Activity of Litchi(Litchi Chinensis Sonn.) Fruit During Cold Storage[J]. Molecules, 2014,19(10):16837-16850. doi: 10.3390/molecules191016837
12. [12]
  Singh C K, Siddiqui I A, Elabd S. Combination Chemoprevention with Grape Antioxidants[J]. Mol Nutr Food Res, 2016,60(6):1406-1415. doi: 10.1002/mnfr.201500945
13. [13]
  Hamid H A, Ramli A N M, Zamri N. UPLC-QTOF/MS-Based Phenolic Profiling of Melastomaceae, Their Antioxidant Activity and Cytotoxic Effects Against Human Breast Cancer Cell MDA-MB-231[J]. Food Chem, 2018,256(1):253-259.
14. [14]
  Zhang G, Chen S, Zhou W. Rapid Qualitative and Quantitative Analyses of Eighteen Phenolic Compounds from Lycium Ruthenicum Murray by UPLC-Q-Orbitrap MS and Their Antioxidant Activity[J]. Food Chem, 2018,269(15):150-156.
15. [15]
  Bissantz C, Kuhn B, Stahl M. A Medicinal Chemist's Guide to Molecular Interactions[J]. J Med Chem, 2010,53(14):061-5084.
16. [16]
  FU Xiaolei, ZHAO Chunhui, ZHANG Yixuan. Synthesis, Characterization and Whitening Activity of Amino Acid-Hydroquinone Conjugates[J]. Chinese J Appl Chem, 2015,32(2):158-165.
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
4. [4]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
5. [5]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
6. [6]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
9. [9]
  Yan Xiao , Shuling Li , Yifan Li , Jianing Fan , Linlin Shi . Discovering the Beauty of Life: Adding Some “Ingredients” to Crystals. University Chemistry, 2024, 39(6): 366-372. doi: 10.3866/PKU.DXHX202312025
10. [10]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
11. [11]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
12. [12]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
13. [13]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
14. [14]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
15. [15]
  Ming Li , Zhaoyin Li , Mengzhu Liu , Shaoxiang Luo . Unveiling the Artistry of Mordant Dyeing: The Coordination Chemistry Beneath. University Chemistry, 2024, 39(5): 258-265. doi: 10.3866/PKU.DXHX202311085
16. [16]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
17. [17]
  Xueyu Lin , Ruiqi Wang , Wujie Dong , Fuqiang Huang . 高性能双金属氧化物负极的理性设计及储锂特性. Acta Physico-Chimica Sinica, 2025, 41(3): 2311005-. doi: 10.3866/PKU.WHXB202311005
18. [18]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
19. [19]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
20. [20]
  Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1250)
HTML views(156)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142