芥子油苷代谢途径图解概要

1、芥子油甘代谢途径图解R YOHCO2N乙醛的0 HaldoximeNADPH+O 2NH2侧链延长side-chain elongation RCYP450CYP79HCYP450CYP83amino acidNADPH+OR次级修饰secondary modificationG-ST: glutathione-S GluCO2RN+O-氧化睛nitrile oxide半胱氨酸cysteineN-O OH酸式硝基化合物aci-nitro compoundG-STH2NSCOOHNOHs-alkyl thiohydroximateNO SO3-芥子油昔glucosinolateG-ST :谷胱甘

2、肽转移酶S-transferase S-GT:图1芥子油昔的合成途径（STS GluNOH脱硫芥子油音desulfoglucosin01ateS-GTRc-s裂解酶0C-S lyaseSHN 一 OHthiohydroximateS-GT : S-糖基转移酶ST:磺基转移酶S-glucosyltransferase ST: sulfotransferaseWittstock U and Halkier B A, 2002H3C一S CH2TlR44-methylthiobutylR= H3CS-GluN-OSO3-ONS4-methylsufinylbutylHO GS-OHBGS-ALKCH

3、2H2C = CH一CH3-butenylR4-hydroxybutylGS-OHOHOBzh2c=ch ch2ch3h2c ch2- R34-benzoyloxybutyl2-hydroxy-3-butenylBzOH2C = CHch2-ch3- R2-benzoyloxy-3-butenyl图2芥子油昔的次级修饰(Kliebenstein D J 2001)+ GluOxazolidine-2-thionesepithionitriles+ snitrile图3 芥子油昔的水解途径(Wittstock U and Halkier B A, 2002)单亚甲基甲硫氨酸homomethion

4、ine双亚甲基甲硫氨酸 dihomomethionine 三亚甲基甲硫氨酸 trihomomethionine 四亚甲基甲硫氨酸tetrahomomethionine五亚甲基甲硫氨酸pentahomomethionine六亚甲基甲硫氨酸hexahomomethionine苯丙氨酸phenylalanine高苯丙氨酸homophenlalanineCYP79C1CYP79C2CYP79F1a CYP79F2CYP79A2色氨酸 tryptophanCYP79B2CYP79B3>图4 CYP450 与芥子油音的生物合成脂肪族醉的aliphatic aldoximes芳香族和吧噪族醉的arom

5、atic and indolealdoximes(Wittstock & Halkier, 2002)CYP83A1CYP83B1芥子油甘glucosinolate叶绿体线粒体elongationMet / H-MetCYP79B2CY079B3Trpside-shianUDPGPAPSSulfo-tansferase卜一GluN O SO3-液泡图6色氨酸与芥子油音、IAA的合成途径的联系NHnh2OH色氨酸from Chen 2001 Plant Physiology Biochemistry 39: 743-758ASA ASB* OHQ /x'O-PO3 NH indo

6、le-3-glycerolphosphate一 _ _p TSATrp-independent去一,indole- C00H 1PATSBOTrpaminoQ O一OHindole-3-pyruvic acidxyQl Nh2ipaehyTrp /Trp步%八 八父CYP79B2/NHCYP79B3 pH dependent人人 lOnh NH2|below 4CrY°,t 八 H spontaneous .?tryptamine1, , '一一NH/ nindole-3-acetaldehydeFLOOZY/ NHOHIAAld/YUCCA/IAOx、/CYP83B1unk

7、nown compound ,/1./sur2/red1/atr4 - 5 NH0HCtA ""ohN-hydroxy tryptamine'H NohS-alkyl thiohydroximate C-S Lyase sur1 QTG NHOHthiohydroximate,UGT74B1、XX- S Gl1ugt74b1N NNH"" OHdesulphoglucosinolateXOH二9 nH 工 威/ /；AA产 / nit1NIT2/NIT3:NIT4/ OTN/NHIAN_SHNH1 SO 3-thiohydroximate-O-s

8、ulfateAmyrosinaseQ-、S- Gluu一 Q （丫NHN O SO 3-indole glucosinolateanthranilateanthranilate一 synthaseASA ASBchorismate图8芥子油音合成与亚麻葬素(camalexin )合成的联系OHOHO PO3NHindole-3-glycerolphosphateTSANH indoleCYP71B15/PAD3 decarboxylationOIAOxCYP79B2CYP79B3HOH nh2 NHTrpcysteineNH dihydrocamalexic acidNHOcamalexinO

9、HNH indole-3-carboxylic acidOHOHS-alkyl thiohydroximateNH brassininCYP83B1 sur2/red1/atr4NH indole-3-acetaldehyde IAAldNH N OHnh2S COOHase一/HNH NNHOHthiohydroximateUGT74B1ugt74b1CH3SNHNH O spirobrassininN QS CHSbrassilexinCH3ScyclobrassininOH desulphoglucosinolateS -GluS GluNHNO SO3-indole glucosino

10、late图9芥子油昔合成与苯丙烷途径(phenylpropanoid pathway)的联系OHPONHindole-3-glycerolphosphateanthranilateanthranilate synthase chorismate .ASA ASBTSAindole NHOOHshikimate pathwayONH TrpOH NH2methionineMAMHCYP79B2CYP79B3NHIAOx(n)homomethionineCYP79F1/F2NHCYP83B1 sur2/red1/atr4NH2 SCOOHN OHS-alkyl thiohydroximateLig

11、ninCOOHFlavonoidsCCoAOMTconiferaldehyde/ coniferyl alcoholNH2Phenylalanine (Phe)t-Cinnamic AcidN OHaldoximethiohydroximateF5HCOMTsinapaldehyde/ sinapyl alcoholsyringyl ligninsinapate estersindole glucosinolatealkyl glucosinolatechorismateanthranilateAgAsynthase anthranilateindole-3-glycerolphosphate

12、MeJAATR1herbivoreMeJA wounding IAATrpIANSATLipaseTryptophanO-AcetylserineLinolenic acidTRPCysteineHydroperoxyTryptamineCgslinolenic acidAOS |i：TCystathionineGlutathioneCYP83B1CbLS-GTAHCSAHCHomocysteineMSAOCCMTMethionine12-Oxo-phytosMMTSAMdienoc acidHMTydSAMSMMOPRGlucoseSAM-DCSulfateJasmonic acidDC-SAMilaseEthyleneCYP79B2CYP79B3Cysteine SynthaseTPR-S bataSpermidine Synthaselipoxygenasee s a 慎 s, Sulfate transpoterIndole-3- acetaldoximeIndole-3- acetaldehydeSAM: JACMTIndole- pyruvic aci