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1、1.17DiterpenesTomonobuToyomasuandTakeshiSassa,YamagataUniversity,Tsuruoka,Japanª2010ElsevierLtd.Allrightsreserved.1.17.1Introduction6431.17.2Labdane-TypeDiterpenes6441.17.2.1FormationofFourCopalylDiphosphateStereoisomers6441.17.2.2FromCopalylDiphosphat
2、e6461.17.2.2.1Diterpeneresinacidsinconifers6461.17.2.2.2Phyllocladane-relatedditerpenesinafungus6471.17.2.3Froment-CopalylDiphosphate6501.17.2.3.1ent-Labdane-relatedditerpenesinrice6501.17.2.3.2ent-Kaurane-relatedditerpenesinmoss6521.17.2.3.3ent-Pimara
3、ne-relatedditerpenesineubacteria6521.17.2.3.4Gibberellins6531.17.2.3.5Steviolglycosides6561.17.2.4Fromsyn-CPP6561.17.2.4.1syn-Labdane-relatedditerpenesinrice6561.17.2.4.2Aphidicolane-relatedditerpenesinafungus6591.17.3Clerodane-andHalimane-TypeDiterpen
4、es6601.17.3.1Clerodane6601.17.3.2Halimane6611.17.4OthertypesofDiterpenes6621.17.4.1TaxaneandPhomactane6621.17.4.2CasbeneandCembratriene6631.17.4.3Fusicoccane6651.17.5SummaryandFutureProspects668References6691.17.1IntroductionAvarietyofcyclicditerpenesa
5、rederivedfromgeranylgeranyldiphosphate(GGPP)throughthecyclizationofGGPPandthechemicalmodificationofcarbonskeletons,suchasoxidation,reduction,acetylation,methyla-tion,andglycosylation.Cyclizationisanimportantandinterestingprocess,fromtheperspectiveofthe
6、formationofavarietyofcarbonskeletons,andisamajorbranchofthebiosynthesisofcyclicditerpenes.In1994,thecasbenesynthasegenefromcasterbean(Ricinuscommunis)wasfirstreportedasaditerpenecyclase1(seeSection1.17.4.2),aswellastheent-copalyldiphosphate(ent-CPP)syn
7、thase(seeSection1.17.2.1)from2Arabidopsisthaliana,whichfunctionsingibberellinbiosynthesis.Asforlabdane-relatedditerpenecyclases,cDNAsencodingtheent-kaurenesynthase(seeSection1.17.2.3)inpumpkin(Cucurbitamaxima)andtheabietadienesynthase(seeSection1.17.2.
8、2.1)ingrandfir(Abiesgrandis),whichfunctioningibberellinbiosynth-3,4esisandabieticacidbiosynthesis,respectively,wereisolatedin1996.Thetaxadienesynthasegene(see5Section1.17.4.1),whichfunctionsintaxolbiosynthesis,wasisolatedfromPacificyew(