The origin and biosynthesis of the naphthalenoid moiety of juglone in black walnut

作     者：Rachel M.McCoy Sagar M.Utturkar Joseph W.Crook Jyothi Thimmapuram Joshua R.Widhalm 

作者机构：Department of Horticulture and Landscape ArchitecturePurdue University625 Agriculture Mall DriveWest LafayetteIN47907USA Purdue Center for Plant BiologyPurdue UniversityWest LafayetteIN47907USA Bioinformatics CorePurdue University155 South Grant StreetWest LafayetteIN47907USA 

出 版 物：《Horticulture Research》 (园艺研究（英文）)

年 卷 期：2018年第5卷第1期

页      面：159-169页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 070303[理学-有机化学] 0710[理学-生物学] 0831[工学-生物医学工程（可授工学、理学、医学学位）] 1001[医学-基础医学(可授医学、理学学位)] 0817[工学-化学工程与技术] 0901[农学-作物学] 0703[理学-化学] 0836[工学-生物工程] 0902[农学-园艺学] 0834[工学-风景园林学（可授工学、农学学位）] 

基　　金：This work was supported by start-up funds and a Showalter Trust Fund award for bioinformatics support from Purdue University to J.R.W This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under Grant No. DGE-1333468 to J.W.C. We thank Jim McKenna (Hardwood Tree Improvement and Regeneration Center, Purdue University) for providing black walnut seedlings and collecting tissues from mature trees, Elena Yakubova for technical assistance, and Jing Yuan for assistance with microscopy 

主　　题：moiety roots synthesizing 

摘      要：Several members of the Juglandaceae family produce juglone,a specialized 1,4-naphthoquinone(1,4-NQ)natural product that is responsible for the notorious allelopathic effects of black walnut(Juglans nigra).Despite its documented ecological roles and potential for being developed as a novel natural product-based herbicide,none of the genes involved in synthesizing juglone have been *** on classical labeling studies,we hypothesized that biosynthesis of juglone’s naphthalenoid moiety is shared with biochemical steps of the phylloquinone ***,using comparative transcriptomics in combination with targeted metabolic profiling of 1,4-NQs in various black walnut organs,we provide evidence that phylloquinone pathway genes involved in 1,4-dihydroxynaphthoic acid(DHNA)formation are expressed in roots for synthesis of a compound other than *** experiments using axenic black walnut root cultures revealed that stable isotopically labeled L-glutamate incorporates into juglone resulting in the same mass shift as that expected for labeling of the quinone ring in *** together,these results indicate that in planta,an intermediate from the phylloquinone pathway provides the naphthalenoid moiety of ***,this work shows that juglone can be de novo synthesized in roots without the contribution of immediate precursors translocated from aerial *** present study illuminates all genes involved in synthesizing the juglone naphthoquinone ring and provides RNA-sequencing datasets that can be used with functional screening studies to elucidate the remaining juglone pathway *** of the generated knowledge is expected to inform future metabolic engineering strategies for harnessing juglone as a novel natural product-based herbicide.