烟草去甲基尼古丁产生的机理

ChineseBulletinofBotany2007,24(4):544-552,:2006-12-04*E-mail:[e-mail]..1,1,2,1,1*1,130021;2,130062,,(tobacco-specificnitrosamines,TSNAs)——(nitrosonornicotine,NNN),,,,,,,,,,,(2007)..24,544-552.()(nicotine),45,()(nornicotine)(anabasine)(anatabine)4(Leete,1983),,90%95%,35%10%,,(tobacco-specificnitrosamines,TSNAs)(Hecht,1998)TSNAs7,(nitrosonornicotine,NNN)4--1-3--1-(4-N-methylnitrosamino-1-3-pyridyl-1-butanone,NNK)(Hecht,1998,2003),N-:(1)(Bushetal.,2001),NNN5%,N-95%NNN,,DickersonJanda(2002),DickersonJanda(2002),,(),545:1N-,2040Dawson(1945)(N.otophora)(N.tomentosformis),,(Goossensetal.,2003),,,,,,,(Chelvarajanetal.,1993)?22.1,(Dawson,1945)Bose(1956)(N.tabacum),LeeteBell(1959),14C-,90%,,James(1975)(N.tabacum),,,,N-,,,,(HaoandYeoman,1998)2.21978,WallexNowacki(WallexandNowicki,1978),KisakiTamaki(1961),()-(())N.tabacumN.glutinosa,1N-Figure1NicotineN-demethylationandnornicotinenitrosation54624(4)2007,,()-nornicotine,,,LeeteChedekel(1974),(2),,,()--N'-(()-nicotine-N'-oxide)(BoothandBoyland,1971;Nwosuetal.,1988),-N'-,(Nwosuetal.,1988),-N'-HaoYeoman(1996a)(N'-formylnornicotine),-NH,,Bartholomeusz(2005a)(GC-MS)(N.plumbaginifolia),,,LeeteChedekel(1972),C/H-2',(+)-Leete(1977),()-(3),,,()-(HaoandYeoman,1996a)Mesnard(2001)(N.plumbaginifolia),(±)-,(±)-,2Figure2Hypothesisfordemethylationofnicotine(LeeteandChedekel,1974)547:31955,Griffith(N.tabacum),,N-,1993,HaoYeoman,,(HaoandYeoman,1993,1996b),(Chelvarajanetal.,1993),,HaoYeoman(1996b)(KmpH),NADPHO2,,,5000MWN'-(HaoandYeoman,1998),P450,(4),P450()N'-N'-,P450NADPH-P450(P450)β-NADPH,2,,N'-,(HaoandYeoman,1998)(Bartholomeuszetal.,2005b),N'-,N'-,,,,3Figure3Hypothesisfordemethylationofnicotinetoracemicnornicotineviatheiminiumsalt(Leete,1977)54824(4)2007(Mesnardetal.,2002),P450,N'-P450,,NADPH(Fanninetal.,2000),,,,,,,,·cDNA,6P450,CYP82E2,90%CYB82E4v1(Siminszkyetal.,2005),,,N-,P450,(,2001)P4504,4.160,30%40%,(N.sylvestris)(N.tomentosformis)(N.otophora)(N.tabacum),,,4Figure4Hypothesisforenzymaticdemethylationofnicotinetonornicotine(HaoandYeoman,1998)549:(2001)76,,,Shi(2004)TN9031,,,10%,,(Shi,2004)Griffith(1955),12MannWebrew(1958),2CsCt(MannandWebrew,1958)2,(DavisandNielson,1999),ctct3%9%();Ctct17%51%;CtCt73%94%ct,,,,,(Shi,2004)4.2,,15%(3),(Shi,2004),,,,,,,,,,(,2006)4.3(N.sylvestris),419,9,1410(,1993)4.4(2006),,IAA,GA3,ABA1,IAA,——ABAGA3(,1998),(2001),IAAGA3,IAA,ABA6-(6-BA)(TIBA)6-BA55024(4)2007TIBA,,(2006),,4.52-2-,(,2006),,37°C,95%23,46(Shietal.,2003)5,,,,(ABA),,20021760,(),2007,90%,,RNAi,,NNN,,,,,(2001)..7,2225.,(2001).P450.:.pp.23.,BushLP,WangJ,(2001)..4,68.,BushLP,,KraussM(2004)..10,2833.(2006)..3,276280.(1998)..22,2527,3437.(1993)..:.pp.306352.BartholomeuszTA,BhogalRK,MolinieR,FelpinFX,MoniqueMA,MeierC,DragerB,LebretonJ,RoscherA,RobinsRJ,MesnardF(2005a).NicotinedemethylationinNicotianaplumbaginifoliacellsuspensioncultures:N'-formylnornicotineisnotinvoled.Phytochemistry66,24322440.BartholomeuszTA,MoliniéR,RoscherA,FelpinFX,GilletF,LebretonJ,MesnardF,RobinsRJ(2005b).StereoselectivityofthedemethylationofnicotinepiperidinehomologuesbyNicotianaplumbaginifoliacellsuspensioncultures.Phytochemistry66,18901897.BoothJ,BoylandE(1971).Enzymaticoxidationof()-nicotinebyguinea-pigtissuesinvitro.BiochemPharmacol20,407415.BoseBC,DeHN,DalalIH(1956).Micro-methodsforestimationofnicotinegroupofalkaloidsintobaccoplants.JIndianChemSoc33,131134.BushLP,CuiM,ShiH,BurtonHR,FanninFF,LeiL,DyeN(2001).Formationoftobacco-specificnitrosaminesinair-cured551:tobacco.RecAdvTobSci27,2346.ChelvarajanRL,FanninFF,BushLP(1993).StudyofnicotinedemethylationinNicotianaotophora.JAgricFoodChem41,858862.DawsonRF(1945).Onthebiosynthesisofnornicotineandanabasine.JAmChemSoc67,503504.DavisDL,NielsonMT(1999).Tobaccoproduction,chemistryandtechnology.Oxford:BlackwellScience.pp.285287.DickersonFJ,JandaKD(2002).Glycationoftheamyloidβ-proteinbyanicotinemetabolite:afortuitouschemicaldynamicbetweensmokingandAlzheimer’sdisease.ProcNatlAcadSciUSA99,1508415088.FanninFF,ShiHZ,BurtonHR(2000).Nicotinetonornicotineconversioninburlytobacco.In:JohnD,ed.AgronomyandPhytopathology.Paris:St.Martin’sPress.pp.5151.GoossensA,HakkinenST,LaaksoI(2003).Afunctionalgenomicsapproachtowardtheunderstandingofsecondarymetabolisminplantcells.ProcNatlAcadSciUSA100,85958600.GriffithRB,ValleauWD,StokesGW(1955).Determinationandinheritanceofnicotinetonornicotineconversionintobacco.Science121,343344.HaoDY,YeomanMM(1993).Bioconversionofadded()-nico-tineto()-nornicotinebycellsuspensionculturesofNicoti-anatabacumL.cv.‘Wisconsin-38’.In:RichardL,ed.Ab-stractandPosterProceedingsofthe15thInternationalBotani-calCongress.NewYork:PlenumPress.40374369.HaoDY,YeomanMM(1996a).MechanismofnicotineN-demethylationintobaccocellsuspensioncultures.Phytochem-istry41,477482.HaoDY,YeomanMM(1996b).NicotineN-demethylaseincell-freepreparationsfromtobaccocellcultures.Phytochemistry42,325329.HaoDY,YeomanMM(1998).EvidenceinfavourofanoxidativeN-demethylationofnicotinetonornicotineintobaccocellcultures.J