Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates

doi:10.11944/j.issn.1000-0518.2016.07.160031

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (7): 780-791.DOI: 10.11944/j.issn.1000-0518.2016.07.160031

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Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates

LI Chang^a,SUN Jingyang^a,ZHI Defu^c,TIAN Tian^a,CHEN Yanhua^a,ZHAO Longxuan^a^b^*(),ZHAO Chunhui^b^*()

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

Received:2016-01-19 Accepted:2016-05-11 Published:2016-06-30 Online:2016-06-30
Contact: ZHAO Longxuan,ZHAO Chunhui
Supported by:
Supported by the National Natural Science Foundation of China(No.21101067)

Abstract

Abstract:

Three alcohol intermediates were synthesized through protection of one side phenolic hydroxyl group, coupling with methyl bromoacetate, and reduction using p-dihydroxybenzene, m-dihydroxybenzene and o-dihydroxybenzene as lead compounds. These three intermediates coupled with three different glycogens to get nine targeting compounds. Similarly, we protected phenolic hydroxyl of 3-(4-hydroxyphenyl)-1-propanol, and then coupled it with three different glycogens to yield three target compounds. The twelve target compounds were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. The study of whitening activity of these conjugates shows that compounds p-HQ-6a, m-HQ-7a, p-HQ-6b, m-HQ-6b, o-HQ-6b, p-HQ-6c, m-HQ-7c, L-3a and L-4b have significant inhibition to tyrosinase, among of them compounds o-HQ-6b and p-HQ-6c against tyrosinase are obviously better than the positive control of α-Abutin.

Key words: arbutin, glycoside, whitening activity

LI Chang, SUN Jingyang, ZHI Defu, TIAN Tian, CHEN Yanhua, ZHAO Longxuan, ZHAO Chunhui. Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates[J]. Chinese Journal of Applied Chemistry, 2016, 33(7): 780-791.

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Synthesis, Characterization and Whitening Activity of Glucoside-phenols Conjugates

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[1]	FU Xiaolei, ZHAO Chunhui, ZHANG Yixuan, CHEN Yanhua, LI Chang, ZHAO Longxuan. Synthesis, Characterization and Whitening Activity of Amino Acid-hydroquinone Conjugates [J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 158-165.
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