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:20089,:2008123Correspondingauthore2mail:jiangyy@sz.tsinghua.edu.cn1,22,321,23(1.100084;2.518055;3.100084),,,,,:O62919;R91412;R962:A:10052281X(2009)07P821500207StructureModificationofResveratrolandPharmacologicalActivityLiuHuachen1,2DongAijun2,3GaoChunmei2JiangYuyang1,23(11KeyLaboratoryofBioorganicPhosphorusChemistry&ChemicalBiology,MinistryofEducation,DepartmentofChemistry,TsinghuaUniversity,Beijing100084,China;21TheKeyLaboratoryofChemicalBiology,GuangdongProvince,GraduateSchoolatShenzhen,TsinghuaUniversity,Shenzhen518055,China;31DepartmentofBiologicalScienceandBiotechnology,TsinghuaUniversity,Beijing100084,China)AbstractInordertoimproveactivityanddecreasetoxicity,searchingforleadcompoundswithbiologicalactivityexistedinthenatureandmodifyingtheirstructuresisanimportantmeansofinnovationofnewdrugs.Resveratrol,aphytoalexinisolatedfromgrapesandotherplants,iswell2knownforitspotentchemopreventivepropertiestowardsthemostseverecontemporaryhumandiseases,suchascancer,vasculardisease,neurodegenerativediseaseandviralinfection,etc.Inrecentyears,moreandmorescientistsmodifythedoublebondorbenzeneringofresveratroltogethigheractivity,lowertoxicityderivates.Inthispaper,thestructure2activityrelationshipsandpharmacologicalpropertiesoftheresveratrolderivativesasapotentchemopreventiveagentarereviewedanddiscussed.Keywordsresveratrol;pharmacologicalactivity;structure2activityrelationshipsContents1Anti2tumoractivityofresveratrol2Structuremodificationofresveratrol211Structuremodificationofresveratrolonethylenicbond212Structuremodificationofresveratrolonbenzenering3Conclusion(resveratrol),21,3172,,,,[17],,Zhang[8]21820098PROGRESSINCHEMISTRYVol.21No.7P8Aug.,2009,,,,SIRT1P53[9][10,11][12,13][14][15],[16][17][18][19],1(DNA,),,[20],,,,[2123]Jang[21],,,DNA,RNADNADNA,RNAP815K562RNA[24]DNA,DNA,[25];(COX)[26],COXCOX(COX21)COX(COX22)COX22,C(PKC)COX22(TGF2),Suenaga[27](A549),TGF2;P53Bax[28],232(PI3K)PAKt21DNA[29]NO2cGMP,[30];,(NOS)[3133](ED)(ED)[34]P38MAP[35][36]2,,,,2111,A,B,[37,38],CardileKageura,[39,40]Pettit[37]2,;,Simoni[41]2,Roberti[42]SAR,HL260,34IC50,,G0G1Pettit[43],5,[44]6MCF27H446231L02,Solladie[45]7,Panzella[46]8,9Tsai[47],10COX21P10517P8COX2211,Lin[48],4011,NMe240Roberti[49],(1213141516),HL60,15G0G1,,1314Minutolo[50]16,MDA2MB2231,Song[51]2,16,1718IC500149M01034MKim[52]19,Mu[53]20,Zhou[54],,2122P2714Pagliai[55],2327,Qu[56]2829,2Tron[57],3031SH2SY5YPirali[58]3233SH2SY5YWang[59]3435HCT215NCI2H460Kim[60]363738A549SK2MEL22MCF27Nam[61],39B16HCT116A431Fuji[62]40,Vilar[63]2,,,4126Mortimer[64],42MCF27MDA468KM12HCC2998Russell[65]4346,Qin[66]4752,205121Li[67]53Nicolaou[68],54Vessieres[69]55,MCF27MDA2MB231Mai[70]SAR,56Reddy[71],57BT20DU145H157DLD1Pandit[72]B,A,5866PC23MDA2MB223111PC23MDA2MB2231[72]Table1InhibitionofPC23(A)andMDA2MB2231(B)cellsbydifferentderivates[72]No.R1R2EorZAPIC50nMBPIC50nM583,4,5,OCH3HE8019593,4,5,OCH3HZ34410602,3,4,OCH3HE58001100612,4,5,OCH3HE6410622,4,5,OCH3HZ9110632,4,6,OCH3HE2210642,4,6,CH3HE1600940652,4,6,C2H5HE114002600663,4,5,OCH3CH3E3137Jung[73],,,6768Liou[74],B,(69)30517P8,Eddarir[75](70),212,Huang[76]2,,,71Hauss[77]A4,72,Cardile[39],7374,73,Zhang[78],,,,75,,[79]76,Matsuoka[80]77,77,4Fukuhara[81],7881,Su[82]8283,COX21COX22NF2BHeynekamp[83]NF2B(TNF2),8485100Lion[84]MDAMB468Kim[52]cytochromeP4501B1,86Murias[85],E28788COX21COX22(COX21IC50COX22IC50)405121546141719123Chen[86]SAR,B,A3,5Mannich,Mannich,899091Botella[87]BA3,59293Qu[88]94X,,Andrus[89]95,HL60,DeMedina[90],,,96Lee[91],,97Botella[87]98Chang[92]99100Wang[93]AB3,,,,,,,,,,[1]SandersTH,McMichaelRW,HendrixKW,etal.J.Agric.FoodChem.,2000,48:12431246[2]LyonsMM,YuC,TomaRB,etal.J.Agric.FoodChem.,2003,51:58675870[3]IbernM,Roig2PerezS,LamuelaRM,etal.J.Agric.FoodChem.,2000,48:63526354[4]GerogiannakiCM,AthanasopoulosP,KyriakidisN,etal.FoodControl,2006,17:700706[5]CounetC,CallemienD,CollinS.FoodChem.,2006,98:649657[6]BavarescoL,VezzulliS,CivardiS,etal.J.Agric.FoodChem.,2008,56:20852089[7]SobolevVS.J.Agric.FoodChem.,2008,56:19491954[8]ZhangY,LiSZ,LiJ,etal.J.Am.Chem.Soc.,2006,128:1303013031[9]HowitzKT,BittermanKJ,CohenHY,etal.Nature,2003,425:191196[10]EnerGS,TokluHZ,EhirliAO,etal.Hepatol.Res.,2006,35:6268[11]ChanWH,ChangYJ.Toxicol.Lett.,2006,161:19[12]LiY,CaoZ,ZhuH.Pharmacol.Res.,2006,53:615[13]CengizA,HaleK,AysunBK,etal.J.Surg.Res.,2005,127:112117[14]KeremZ,RegevSG,FlaishmanMA,etal.J.Nat.Prod.,2003,66:12701272[15]CignarellaA,MiniciC,BolegoC,BolegoI,PeloslV,PuglisiL,GaionRM.InternationalSymposiumonAtherosclerosis,Rome:Elsevier,2006.1822[16]HornTL,CwikMJ,MorrisseyRL,etal.FoodandChem.Toxicol.,2007,45:5563[17](ZhangBH).(ModernHospital),2008,8(3):6668[18](LiXB),(XieRM).(PharmacyofWestChina),2007,4(1):3739[19]LiuH,DongA,GaoC,etal.Bioorg.Med.Chem.,2008,16:1001310021[20]SurhYJ.Nat.Rev.Cancer,2003,3:768780[21]JangM,CaiL,UdeaniGO,etal.Science,1997,275:218220[22]KelloffGJ,CrowellJA,SteeleVE,etal.J.Nutr.,2000,130:467S471S[23]GusmanJ,MalonneH,AtasstG,etal.Carcinogenesis,2001,22:11111117[24]FontecaveM,LepoivreM,ElleingandE,etal.FEBSLett.,1998,421:277279[25]SunNJ,WooS,CassadyJM,etal.J.Nat.P