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Recently duplicated sesterterpene(C25) gene clusters in Arabidopsis thaliana modulate root microbiota

Science China(Life Sciences) 2019年第7期62卷 947-958页

作者： Qingwen Chen Ting Jiang Yong-Xin Liu Haili Liu Tao Zhao Zhixi Liu Xiangchao Gan Asis Hallab Xuemei Wang Juan He Yihua Ma Fengxia Zhang Tao Jin M. Eric Schranz Yong Wang Yang Bai Guodong Wang State Key Laboratory of Plant Genomics and National Center for Plant Gene Research Institute of Genetics and Developmental BiologyThe Innovative Academy of Seed DesignChinese Academy of SciencesBeijing 100101China Key Laboratory of Synthetic Biology Institute of Plant Physiology and EcologyShanghai Institutes far Biological SciencesChinese Academy of SciencesShanghai 200032China Biosystematics Group Wageningen University6708 PB WageningenThe Netherlands CAS-JIC Centre of Excellence for Plant and Microbial Sciences (CEPAMS) Institute of Genetics and Developmental BiologyChinese Academy of SciencesBeijing 100101China Max Planck Institute for Plant Breeding Research Carl-von-Linne-Weg 1050829 KolnGermany Forschungszentrum Jiilich Plant Sciences (IBG-2) Wilhelm-Johnen-Straβe52428 JillichGermany China National Genebank-Shenzhen the Beijing Genomics Institute (BGI-Shenzhen)Shenzhen 518083China College of Advanced Agricultural Sciences University of Chinese Academy of SciencesBeijing 100039China

Land plants co-speciate with a diversity of continually expanding plant specialized metabolites(PSMs) and root microbial communities(microbiota).Homeostatic interactions between plants and root microbiota are essential for plant survival in natural environments.A growing appreciation of microbiota for plant health is fuelling rapid advances in genetic mechanisms of controlling microbiota by host *** have long been proposed to mediate plant and single microbe ***,the effects of PSMs,especially those evolutionarily new PSMs,on root microbiota at community level remain to be ***,we discovered sesterterpenes in Arabidopsis thaliana,produced by recently duplicated prenyltransferase-terpene synthase(PT-TPS) gene clusters,with neo-functionalization.A single-residue substitution played a critical role in the acquisition of sesterterpene synthase(sesterTPS) activity in Brassicaceae ***,we found that the absence of two root-specific sesterterpenoids,with similar chemical structure,significantly affected root microbiota assembly in similar *** results not only demonstrate the sensitivity of plant microbiota to PSMs but also establish a complete framework of host plants to control root microbiota composition through evolutionarily dynamic PSMs.

关键词： plant specialized metabolites microbiota sesterterpene terpene synthase

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Molecular Basis for sesterterpene Diversity Produced by Plant Terpene Synthases

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Plant Communications 2020年第5期1卷 41-52页

作者： Qingwen Chen Jianxu Li Zhixi Liu Takaaki Mitsuhashi Yuting Zhang Haili Liu Yihua Ma Juan He Tetsuro Shinada Tsutomu Sato Yong Wang Hongwei Liu Ikuro Abe Peng Zhang Guodong Wang State Key Laboratory of Plant Genomics and National Center for Plant Gene Research Institute of Genetics and Developmental BiologyThe Innovative Academy of Seed DesignChinese Academy of SciencesBeijing 100101China National Key Laboratory of Plant Molecular Genetics Center for Excellence in Molecular Plant SciencesShanghai Institute of Plant Physiology and EcologyChinese Academy of SciencesShanghai 200032China Graduate School of Pharmaceutical Sciences University of Tokyo7-3-1 HongoBunkyo-kuTokyo 113-0033Japan State Key Laboratory of Mycology Institute of MicrobiologyChinese Academy of SciencesBeijing 100101China Key Laboratory of Synthetic Biology Institute of Plant Physiology and EcologyShanghai Institutes for Biological SciencesChinese Academy of SciencesShanghai 200032China University of Chinese Academy of Sciences Beijing 100039China Graduate School of Science Osaka City University3-3-138 SugimotoSumiyoshiOsaka 558-8585Japan Department of Applied Biological Chemistry Faculty of AgricultureGraduate School of Science and TechnologyNiigata University8050 Ikarashi-2Niigata 950-2181Japan

Class I terpene synthase(TPS)generates bioactive terpenoids with diverse *** synthase(sester-TPS,C25),a branch of class I TPSs,was recently identified in ***,the catalytic mechanisms of sester-TPSs are not fully ***,we first identified three nonclustered functional sester-TPSs(AtTPS06,AtTPS22,and AtTPS29)in Arabidopsis ***06 utilizes a type-B cyclization mechanism,whereas most other sester-TPSs produce various sesterterpene backbones via a type-A cyclization *** then determined the crystal structure of the AtTPS18–FSPP complex to explore the cyclization mechanism of plant *** used structural comparisons and site-directed mutagenesis to further elucidate the mechanism:(1)mainly due to the outward shift of helix G,plant sester-TPSs have a larger catalytic pocket than do mono-,sesqui-,and di-TPSs to accommodate GFPP;(2)type-A sester-TPSs have more aromatic residues(five or six)in their catalytic pocket than classic TPSs(two or three),which also determines whether the type-A or type-B cyclization mechanism is active;and(3)the other residues responsible for product fidelity are determined by interconversion of AtTPS18 and its close ***,this study improves our understanding of the catalytic mechanism of plant sester-TPS,which ultimately enables the rational engineering of sesterterpenoids for future applications.

关键词： terpenoid terpene synthase sesterterpene cyclization mechanism crystal structure

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Phyllofenone A, a New Scalarane sesterterpene from the Sponge Phyllospongia Foliascens(Pallas)

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Chemical Research in Chinese Universities 1991年第2期7卷 100-106页

作者： John K. Snyder Department of Chemistry Boston University Boston USAhe present paper covers the structure of a new sesterterpene phyllofenone A(1) isolated from the South China Sea sponge Phyllospongia foliascens. Phyllofenone A is a member of the scalarane class of sesterterpenes with a (C-20 C-24)-bishomo-(C-25)-nortetra-cyclic skeleton. The structure charcterization was based on one- and two-dimensional NMR and mass spectroscopy with the assistance of molecular modeling. Phyllofenone A shows weak antifungal activity against Candida pseudotropicalis.

The present paper covers the structure of a new sesterterpene, phyllofenone A(1) , isolated from the South China Sea sponge Phyllospongia foliascens. Phyllofenone A is a member of the scalarane class of sesterterpenes with a (C-20, C-24)-bishomo-(C-25)-nortetra-cyclic skeleton. The structure charcterization was based on one- and two-dimensional NMR and mass spectroscopy with the assistance of molecular modeling. Phyllofenone A shows weak antifungal activity against Candida pseudotropicalis.

关键词： Sponge sesterterpene Selective INEPT 2D NMR

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Expanding catalytic promiscuity of a bifunctional terpene synthase through a single mutation-induced change in hydrogen-bond network within the catalytic pocket

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Synthetic and Systems Biotechnology 2024年第2期9卷 380-387页

作者： Xinye Wang Yiyi Huang Weiyan Zhang Kangjie Lv Xiaoying Li Zhixin Wang Li Zhang Tom Hsiang Lixin Zhang Liming Ouyang Xueting Liu State Key Laboratory of Bioreactor Engineering East China University of Science and TechnologyShanghai200237China Department of Chemistry Boston UniversityBostonMAUSA School of Environmental Sciences University of Guelph50 Stone Road EastGuelphOntarioN1G 2W1Canada

Fungal bifunctional terpene synthases(BFTSs)catalyze the formation of numerous di-/sester-/tri-terpenes ***,the mechanism in controlling the cyclization pattern of terpene scaffolds is rarely deciphered for further application of tuning the catalytic promiscuity of terpene synthases for expanding the chemical *** this study,we expanded the catalytic promiscuity of Fusarium oxysporum fusoxypene synthase(FoFS)by a single mutation at L89,leading to the production of three new *** computational analysis revealed that the reconstitution of the hydrogen-bond(H-bond)network of second-shell residues around the active site of FoFS influences the orientation of the aromatic residue W69 within the first-shell catalytic ***,the dynamic orientation of W69 alters the carbocation transport,leading to the production of diverse ring system *** findings enhance our knowledge on understanding the molecular mechanisms,which could be applied on protein engineering terpene synthases on regulating the terpene skeletons.

关键词： Bifunctional terpene synthase sesterterpene Carbocation transportation Density functional theory calculations Molecular dynamics simulations

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Heteromerization of short-chain trans-prenyltransferase controls precursor allocation within a plastidial terpenoid network

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Journal of Integrative Plant Biology 2023年第5期65卷 1170-1182页

作者： Yihua Ma Qingwen Chen Yaoyao Wang Fengxia Zhang Chengyuan Wang Guodong Wang State Key Laboratory of Plant Genomics Institute of Genetics and Developmental BiologyThe Innovative Academy of Seed DesignChinese Academy of SciencesBeijing 100101China UniversityofChineseAcademyof Sciences Beijing100039China Center for Microbes Development and HealthInstitut Pasteur of ShanghaiChinese Academy of SciencesShanghai 200031China

Terpenes are the largest and most diverse class of plant specialized ***(C25),which are derived from the plastid methylerythritol phosphate pathway,were recently characterized in *** Arabidopsis thaliana,four genes encoding geranylfarnesyl diphosphate synthase(GFPPS)(AtGFPPS1 to 4)are responsible for the production of GFPP,which is the common precursor for sesterterpene ***,the interplay between sesterterpenes and other known terpenes remain ***,we first provide genetic evidence to demonstrate that GFPPSs are responsible for sesterterpene production in *** of the sesterterpene pathway at the GFPPS step increased the production of geranylgeranyl diphosphate(GGPP)-derived ***,co-expression of sester TPSs in GFPPSOE(overexpression)plants rescued the phenotypic changes of GFPPS-OE plants by restoring the endogenous *** further demonstrated that,in addition to precursor(DMAPP/IPP)competition by GFPPS and GGPP synthase(GGPPS)in plastids,GFPPS directly decreased the activity of GGPPS through protein-protein interaction,ultimately leading to GGPP deficiency in *** study provides a new regulatory mechanism of the plastidial terpenoid network in plant cells.

关键词： Arabidopsis geranylfarnesyl diphosphate synthase geranylgeranyl pyrophosphate synthase plastid sesterterpene terpene network

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