Synthesis,Characterization And Study On Whitening Activity Of Glucoside-phenols Conjugates

Glucoside-phenols conjugates shows a variety of biological activities,such as whitening effect,remove the body of free radical,cardiovascular protection,enhance immunity,etc.Representative compounds are ?-Arbutin and salidroside.Position of phenolic hydroxyl groups,length of carbon chain and different glycogen are important to activities.So more researchers focused development of novel glucoside-phenols conjugates.To further study of the phenolic glycoside conjugates,according to the combination principles,we are trying to couple the analogues of tyrosol and different glycogens and getting a series of phenolic glycoside conjugates,and evaluated the inhibition of tyrosinase activity of intermediates and final products,in order to get a better whitening activity compounds.There are three parts in this dissertation:Part ?:Reviewed the research progress of arbutin and salidroside,as well as their applications in medicine and drugs.Part ?:Describes the design,synthesis and characterization of phenolic glycoside conjugate.We synthesized 33 compounds,24 compounds have not been reported.1.Using o-dihydroxybenzene,m-dihydroxybenzene and p-dihydroxybenzene as starting material,through the protection of one side phenolic hydroxyl,the other side of phenolic hydroxyl coupling with methyl bromoacetate and reduction.We get three different alcohol intermediates(p-HQ-4,o-HQ-4,m-HQ-4).Similarly phenolic hydroxyl of 3-(4-hydroxyphenyl)-1-propanol was protected,we get another alcohol intermediates(L-1).2.The four kinds of the alcohol intermediate coupled with bromo-tetraacetyl glucose and four kinds of phenolic glycoside conjugate(p-HQ-6a,m-HQ-6a,o-HQ-6a,L-3a)were obtained,four kinds of target compounds(p-HQ-7a,m-HQ-7a,o-HQ-7a,L-4a)were gotten by the removal of benzyl group.3.The four kinds of the alcohol intermediate coupled with bromo-tetraacetyl xylose and four kinds of phenolic glycoside conjugate(p-HQ-6b,m-HQ-6b,o-HQ-6b,L-3b)were obtained,four kinds of target compounds(p-HQ-7b,m-HQ-7b,o-HQ-7b,L-4b)were gotten by the removal of benzyl group.4.The four kinds of the alcohol intermediate coupled with bromo-tetraacetyl galactose and four kinds of phenolic glycoside conjugate(p-HQ-6c,m-HQ-6c,o-HQ-6c,L-3b)were obtained,four kinds of target compounds(p-HQ-7c,m-HQ-7c,o-HQ-7c,L-4b)were gotten by the removal of benzyl group.24 new compounds were characterized by IR,1H NMR,13C NMR and ESI-MS.etc.Part III:Their in vitro inhibition activities towards tyrosinase were evaluated and the results indicate that 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 the inhibition of tyrosinase.o-HQ-6b,p-HQ-6c against tyrosinase are better than the positive control a-Arbutin.But the inhibition of p-HQ-6a,m-HQ-7a,p-HQ-6b,m-HQ-6b,m-HQ-7c,L-3a and L-4b were weaker than the positive control a-Arbutin.