Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity
Abstract
Terpenoids comprise tens of thousands of small molecule natural products that are widely distributed across all domains of life. Plants produce by far the largest array of terpenoids with various roles in development and chemical ecology. Driven by selective pressure to adapt to their specific ecological niche, individual species form only a fraction of the myriad plant terpenoids, typically representing unique metabolite blends. Terpene synthase (TPS) enzymes are the gatekeepers in generating terpenoid diversity by catalyzing complex carbocation-driven cyclization, rearrangement, and elimination reactions that enable the transformation of a few acyclic prenyl diphosphate substrates into a vast chemical library of hydrocarbon and, for a few enzymes, oxygenated terpene scaffolds. The seven currently defined clades (a-h) forming the plant TPS family evolved from ancestral triterpene synthase- and prenyl transferase-type enzymes through repeated events of gene duplication and subsequent loss, gain, or fusion of protein domains and further functional diversification. Lineage-specific expansion of these TPS clades led to variable family sizes that may range from a single TPS gene to families of more than 100 members that may further function as part of modular metabolic networks to maximize the number of possible products. Accompanying gene family expansion, the TPS family shows amore »
- Authors:
- Publication Date:
- Research Org.:
- Univ. of California, Davis, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER). Biological Systems Science Division
- OSTI Identifier:
- 1567897
- Alternate Identifier(s):
- OSTI ID: 1633652
- Grant/Contract Number:
- SC0019178
- Resource Type:
- Published Article
- Journal Name:
- Frontiers in Plant Science
- Additional Journal Information:
- Journal Name: Frontiers in Plant Science Journal Volume: 10; Journal ID: ISSN 1664-462X
- Publisher:
- Frontiers Research Foundation
- Country of Publication:
- Switzerland
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; terpenoids; terpene synthases; plant specialized metabolism; plant chemical diversity; terpenoid biosynthesis; natural products
Citation Formats
Karunanithi, Prema S., and Zerbe, Philipp. Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity. Switzerland: N. p., 2019.
Web. doi:10.3389/fpls.2019.01166.
Karunanithi, Prema S., & Zerbe, Philipp. Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity. Switzerland. https://doi.org/10.3389/fpls.2019.01166
Karunanithi, Prema S., and Zerbe, Philipp. Tue .
"Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity". Switzerland. https://doi.org/10.3389/fpls.2019.01166.
@article{osti_1567897,
title = {Terpene Synthases as Metabolic Gatekeepers in the Evolution of Plant Terpenoid Chemical Diversity},
author = {Karunanithi, Prema S. and Zerbe, Philipp},
abstractNote = {Terpenoids comprise tens of thousands of small molecule natural products that are widely distributed across all domains of life. Plants produce by far the largest array of terpenoids with various roles in development and chemical ecology. Driven by selective pressure to adapt to their specific ecological niche, individual species form only a fraction of the myriad plant terpenoids, typically representing unique metabolite blends. Terpene synthase (TPS) enzymes are the gatekeepers in generating terpenoid diversity by catalyzing complex carbocation-driven cyclization, rearrangement, and elimination reactions that enable the transformation of a few acyclic prenyl diphosphate substrates into a vast chemical library of hydrocarbon and, for a few enzymes, oxygenated terpene scaffolds. The seven currently defined clades (a-h) forming the plant TPS family evolved from ancestral triterpene synthase- and prenyl transferase-type enzymes through repeated events of gene duplication and subsequent loss, gain, or fusion of protein domains and further functional diversification. Lineage-specific expansion of these TPS clades led to variable family sizes that may range from a single TPS gene to families of more than 100 members that may further function as part of modular metabolic networks to maximize the number of possible products. Accompanying gene family expansion, the TPS family shows a profound functional plasticity, where minor active site alterations can dramatically impact product outcome, thus enabling the emergence of new functions with minimal investment in evolving new enzymes. This article reviews current knowledge on the functional diversity and molecular evolution of the plant TPS family that underlies the chemical diversity of bioactive terpenoids across the plant kingdom.},
doi = {10.3389/fpls.2019.01166},
journal = {Frontiers in Plant Science},
number = ,
volume = 10,
place = {Switzerland},
year = {2019},
month = {10}
}
https://doi.org/10.3389/fpls.2019.01166
Web of Science
Works referenced in this record:
Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis
journal, December 2010
- Köksal, Mustafa; Jin, Yinghua; Coates, Robert M.
- Nature, Vol. 469, Issue 7328
Terpene synthase genes in eukaryotes beyond plants and fungi: Occurrence in social amoebae
journal, October 2016
- Chen, Xinlu; Köllner, Tobias G.; Jia, Qidong
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 43
Functional divergence of diterpene syntheses in the medicinal plant Salvia miltiorrhiza Bunge
journal, June 2015
- Cui, Guanghong; Duan, Lixin; Jin, Baolong
- Plant Physiology
Chrysanthemyl diphosphate synthase: Isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium
journal, April 2001
- Rivera, S. B.; Swedlund, B. D.; King, G. J.
- Proceedings of the National Academy of Sciences, Vol. 98, Issue 8
Terpenoid metabolism.
journal, July 1995
- McGarvey, D. J.; Croteau, R.
- The Plant Cell, Vol. 7, Issue 7
Breaking new ground in the regulation of the early steps of plant isoprenoid biosynthesis
journal, June 2015
- Rodríguez-Concepción, Manuel; Boronat, Albert
- Current Opinion in Plant Biology, Vol. 25
Plant metabolism, the diverse chemistry set of the future
journal, September 2016
- Wurtzel, E. T.; Kutchan, T. M.
- Science, Vol. 353, Issue 6305
The Eucalyptus terpene synthase gene family
journal, June 2015
- Külheim, Carsten; Padovan, Amanda; Hefer, Charles
- BMC Genomics, Vol. 16, Issue 1
Identification of Syn -Pimara-7,15-Diene Synthase Reveals Functional Clustering of Terpene Synthases Involved in Rice Phytoalexin/Allelochemical Biosynthesis
journal, August 2004
- Wilderman, P. Ross; Xu, Meimei; Jin, Yinghua
- Plant Physiology, Vol. 135, Issue 4
Long-distance signalling in plant defence
journal, June 2008
- Heil, Martin; Ton, Jurriaan
- Trends in Plant Science, Vol. 13, Issue 6
Demonstration That Menthofuran Synthase of Mint (Mentha) Is a Cytochrome P450 Monooxygenase: Cloning, Functional Expression, and Characterization of the Responsible Gene
journal, June 2001
- Bertea, Cinzia M.; Schalk, Michel; Karp, Frank
- Archives of Biochemistry and Biophysics, Vol. 390, Issue 2
Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants
journal, July 2015
- Henry, Laura K.; Gutensohn, Michael; Thomas, Suzanne T.
- Proceedings of the National Academy of Sciences, Vol. 112, Issue 32
Structure of the ent -Copalyl Diphosphate Synthase PtmT2 from Streptomyces platensis CB00739, a Bacterial Type II Diterpene Synthase
journal, August 2016
- Rudolf, Jeffrey D.; Dong, Liao-Bin; Cao, Hongnan
- Journal of the American Chemical Society, Vol. 138, Issue 34
Lettuce Costunolide Synthase ( CYP71BL2 ) and Its Homolog ( CYP71BL1 ) from Sunflower Catalyze Distinct Regio- and Stereoselective Hydroxylations in Sesquiterpene Lactone Metabolism
journal, April 2011
- Ikezawa, Nobuhiro; Göpfert, Jens Christian; Nguyen, Don Trinh
- Journal of Biological Chemistry, Vol. 286, Issue 24
Isoprenyl diphosphate synthases: the chain length determining step in terpene biosynthesis
journal, November 2018
- Nagel, Raimund; Schmidt, Axel; Peters, Reuben J.
- Planta, Vol. 249, Issue 1
Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster
journal, January 2012
- Wang, Qiang; Hillwig, Matthew L.; Okada, Kazunori
- Journal of Biological Chemistry, Vol. 287, Issue 9
Cross-talk between the Cytosolic Mevalonate and the Plastidial Methylerythritol Phosphate Pathways in Tobacco Bright Yellow-2 Cells
journal, May 2003
- Hemmerlin, Andréa; Hoeffler, Jean-François; Meyer, Odile
- Journal of Biological Chemistry, Vol. 278, Issue 29
Promiscuous terpene synthases from Prunella vulgaris highlight the importance of substrate and compartment switching in terpene synthase evolution
journal, April 2019
- Johnson, Sean R.; Bhat, Wajid Waheed; Sadre, Radin
- New Phytologist, Vol. 223, Issue 1
Product Rearrangement from Altering a Single Residue in the Rice syn -Copalyl Diphosphate Synthase
journal, February 2016
- Potter, Kevin C.; Jia, Meirong; Hong, Young J.
- Organic Letters, Vol. 18, Issue 5
Identification of Diterpene Biosynthetic Gene Clusters and Functional Analysis of Labdane-Related Diterpene Cyclases in Phomopsis amygdali
journal, April 2008
- Toyomasu, Tomonobu; Niida, Rie; Kenmoku, Hiromichi
- Bioscience, Biotechnology, and Biochemistry, Vol. 72, Issue 4
A Single Residue Switch Converts Abietadiene Synthase into a Pimaradiene Specific Cyclase
journal, December 2007
- Wilderman, P. Ross; Peters, Reuben J.
- Journal of the American Chemical Society, Vol. 129, Issue 51
A database-driven approach identifies additional diterpene synthase activities in the mint family (Lamiaceae)
journal, November 2018
- Johnson, Sean R.; Bhat, Wajid Waheed; Bibik, Jacob
- Journal of Biological Chemistry, Vol. 294, Issue 4
Molecular and functional evolution of the fungal diterpene synthase genes
journal, October 2015
- Fischer, Marc JC; Rustenhloz, Camille; Leh-Louis, Véronique
- BMC Microbiology, Vol. 15, Issue 1
Structure of limonene synthase, a simple model for terpenoid cyclase catalysis
journal, March 2007
- Hyatt, D. C.; Youn, B.; Zhao, Y.
- Proceedings of the National Academy of Sciences, Vol. 104, Issue 13
Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens
journal, June 2006
- Keeling, Christopher I.; Bohlmann, Jörg
- New Phytologist, Vol. 170, Issue 4
Structure, mechanism and function of prenyltransferases: Structure, mechanism and function of prenyltransferases
journal, July 2002
- Liang, Po-Huang; Ko, Tzu-Ping; Wang, Andrew H. -J
- European Journal of Biochemistry, Vol. 269, Issue 14
Formation of the Unusual Semivolatile Diterpene Rhizathalene by the Arabidopsis Class I Terpene Synthase TPS08 in the Root Stele Is Involved in Defense against Belowground Herbivory
journal, March 2013
- Vaughan, Martha M.; Wang, Qiang; Webster, Francis X.
- The Plant Cell, Vol. 25, Issue 3
Structure of a Three-Domain Sesquiterpene Synthase: A Prospective Target for Advanced Biofuels Production
journal, December 2011
- McAndrew, Ryan P.; Peralta-Yahya, Pamela P.; DeGiovanni, Andy
- Structure, Vol. 19, Issue 12
Emergence of terpene cyclization in Artemisia annua
journal, February 2015
- Salmon, Melissa; Laurendon, Caroline; Vardakou, Maria
- Nature Communications, Vol. 6, Issue 1
Abietadiene Synthase Catalysis: Conserved Residues Involved in Protonation-Initiated Cyclization of Geranylgeranyl Diphosphate to (+)-Copalyl Diphosphate †
journal, February 2002
- Peters, Reuben J.; Croteau, Rodney B.
- Biochemistry, Vol. 41, Issue 6
Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis
journal, April 2013
- Vranová, Eva; Coman, Diana; Gruissem, Wilhelm
- Annual Review of Plant Biology, Vol. 64, Issue 1
Terpenes in Cannabis sativa – From plant genome to humans
journal, July 2019
- Booth, Judith K.; Bohlmann, Jörg
- Plant Science, Vol. 284
Biochemical characterization of microbial type terpene synthases in two closely related species of hornworts, Anthoceros punctatus and Anthoceros agrestis
journal, May 2018
- Xiong, Wangdan; Fu, Jianyu; Köllner, Tobias G.
- Phytochemistry, Vol. 149
Functional Characterization of Two Class II Diterpene Synthases Indicates Additional Specialized Diterpenoid Pathways in Maize (Zea mays)
journal, October 2018
- Murphy, Katherine M.; Ma, Li-Ting; Ding, Yezhang
- Frontiers in Plant Science, Vol. 9
Towards Elucidating Carnosic Acid Biosynthesis in Lamiaceae: Functional Characterization of the Three First Steps of the Pathway in Salvia fruticosa and Rosmarinus officinalis
journal, May 2015
- Božić, Dragana; Papaefthimiou, Dimitra; Brückner, Kathleen
- PLOS ONE, Vol. 10, Issue 5
Molecular Diversity of Terpene Synthases in the Liverwort Marchantia polymorpha
journal, September 2016
- Kumar, Santosh; Kempinski, Chase; Zhuang, Xun
- The Plant Cell
A terpene synthase-cytochrome P450 cluster in Dictyostelium discoideum produces a novel trisnorsesquiterpene
journal, May 2019
- Chen, Xinlu; Luck, Katrin; Rabe, Patrick
- eLife, Vol. 8
Interaction with the Small Subunit of Geranyl Diphosphate Synthase Modifies the Chain Length Specificity of Geranylgeranyl Diphosphate Synthase to Produce Geranyl Diphosphate
journal, December 2001
- Burke, Charles; Croteau, Rodney
- Journal of Biological Chemistry, Vol. 277, Issue 5
Carnosic acid biosynthesis elucidated by a synthetic biology platform
journal, March 2016
- Ignea, Codruta; Athanasakoglou, Anastasia; Ioannou, Efstathia
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 13
Unknown components of the plastidial permeome
journal, August 2014
- Pick, Thea R.; Weber, Andreas P. M.
- Frontiers in Plant Science, Vol. 5
Molecular cloning, expression and characterization of cDNA encoding cis-prenyltransferases from Hevea brasiliensis: A key factor participating in natural rubber biosynthesis
journal, November 2003
- Asawatreratanakul, Kasem; Zhang, Yuan-Wei; Wititsuwannakul, Dhirayos
- European Journal of Biochemistry, Vol. 270, Issue 23
Functional plasticity of paralogous diterpene synthases involved in conifer defense
journal, January 2008
- Keeling, C. I.; Weisshaar, S.; Lin, R. P. C.
- Proceedings of the National Academy of Sciences, Vol. 105, Issue 3
P450s controlling metabolic bifurcations in plant terpene specialized metabolism
journal, September 2017
- Banerjee, Aparajita; Hamberger, Björn
- Phytochemistry Reviews, Vol. 17, Issue 1
cis or trans with class II diterpene cyclases
journal, January 2017
- Jia, Meirong; Peters, Reuben J.
- Organic & Biomolecular Chemistry, Vol. 15, Issue 15
The Gymnosperm Cytochrome P450 CYP750B1 Catalyzes Stereospecific Monoterpene Hydroxylation of (+)-Sabinene in Thujone Biosynthesis in Western Redcedar
journal, March 2015
- Gesell, Andreas; Blaukopf, Markus; Madilao, Lina
- Plant Physiology, Vol. 168, Issue 1
Predicting pathways for terpene formation from first principles – routes to known and new sesquiterpenes
journal, January 2014
- Isegawa, Miho; Maeda, Satoshi; Tantillo, Dean J.
- Chemical Science, Vol. 5, Issue 4
Biosynthesis of the Diterpenoid Lycosantalonol via Nerylneryl Diphosphate in Solanum lycopersicum
journal, March 2015
- Matsuba, Yuki; Zi, Jiachen; Jones, A. Daniel
- PLOS ONE, Vol. 10, Issue 3
Structure and Mechanism of an Arabidopsis Medium/Long-Chain-Length Prenyl Pyrophosphate Synthase
journal, January 2011
- Hsieh, Fu-Lien; Chang, Tao-Hsin; Ko, Tzu-Ping
- Plant Physiology, Vol. 155, Issue 3
Predicting Productive Binding Modes for Substrates and Carbocation Intermediates in Terpene Synthases—Bornyl Diphosphate Synthase As a Representative Case
journal, March 2018
- O’Brien, Terrence E.; Bertolani, Steven J.; Zhang, Yue
- ACS Catalysis, Vol. 8, Issue 4
Predicting the Functions and Specificity of Triterpenoid Synthases: A Mechanism-Based Multi-intermediate Docking Approach
journal, October 2014
- Tian, Bo-Xue; Wallrapp, Frank H.; Holiday, Gemma L.
- PLoS Computational Biology, Vol. 10, Issue 10
Diterpene cyclases and the nature of the isoprene fold
journal, April 2010
- Cao, Rong; Zhang, Yonghui; Mann, Francis M.
- Proteins: Structure, Function, and Bioinformatics, Vol. 78, Issue 11
Identification of the single amino acid involved in quenching the ent-kauranyl cation by a water molecule in ent-kaurene synthase of Physcomitrella patens: Quenching of ent-kauranyl cation in PpCPS/KS
journal, December 2010
- Kawaide, Hiroshi; Hayashi, Ken-ichiro; Kawanabe, Ryo
- FEBS Journal, Vol. 278, Issue 1
Arabidopsis thaliana isoprenyl diphosphate synthases produce the C 25 intermediate geranylfarnesyl diphosphate
journal, December 2015
- Nagel, Raimund; Bernholz, Carolin; Vranová, Eva
- The Plant Journal, Vol. 84, Issue 5
Two rings in them all: The labdane-related diterpenoids
journal, January 2010
- Peters, Reuben J.
- Natural Product Reports, Vol. 27, Issue 11
One amino acid makes the difference: the formation of ent-kaurene and 16α-hydroxy-ent-kaurane by diterpene synthases in poplar
journal, October 2015
- Irmisch, Sandra; Müller, Andrea T.; Schmidt, Lydia
- BMC Plant Biology, Vol. 15, Issue 1
The formation and function of plant volatiles: perfumes for pollinator attraction and defense
journal, June 2002
- Pichersky, Eran; Gershenzon, Jonathan
- Current Opinion in Plant Biology, Vol. 5, Issue 3
Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase
journal, September 1997
- Starks, C. M.
- Science, Vol. 277, Issue 5333
Correction to Structural and Chemical Biology of Terpenoid Cyclases
journal, December 2018
- Christianson, David W.
- Chemical Reviews, Vol. 118, Issue 24
Biosynthesis of mono- and sesquiterpenes in carrot roots and leaves ( L.): metabolic cross talk of cytosolic mevalonate and plastidial methylerythritol phosphate pathways
journal, February 2005
- Hampel, D.; Mosandl, A.; Wust, M.
- Phytochemistry, Vol. 66, Issue 3
The early stages of taxol biosynthesis: An interim report on the synthesis and identification of early pathway metabolites
journal, January 2012
- Guerra-Bubb, Jennifer; Croteau, Rodney; Williams, Robert M.
- Natural Product Reports, Vol. 29, Issue 6
Both methylerythritol phosphate and mevalonate pathways contribute to biosynthesis of each of the major isoprenoid classes in young cotton seedlings
journal, February 2014
- Opitz, Stefan; Nes, W. David; Gershenzon, Jonathan
- Phytochemistry, Vol. 98
Cyclopentane-forming di/sesterterpene synthases: widely distributed enzymes in bacteria, fungi, and plants
journal, January 2018
- Minami, Atsushi; Ozaki, Taro; Liu, Chengwei
- Natural Product Reports, Vol. 35, Issue 12
An integrated genomic, proteomic and biochemical analysis of (+)-3-carene biosynthesis in Sitka spruce (Picea sitchensis) genotypes that are resistant or susceptible to white pine weevil: (+)-3-carene biosynthesis in Sitka spruce
journal, February 2011
- Hall, Dawn E.; Robert, Jeanne A.; Keeling, Christopher I.
- The Plant Journal, Vol. 65, Issue 6
Functional Characterization of Nine Norway Spruce TPS Genes and Evolution of Gymnosperm Terpene Synthases of the TPS-d Subfamily
journal, August 2004
- Martin, Diane M.; Fäldt, Jenny; Bohlmann, Jörg
- Plant Physiology, Vol. 135, Issue 4
Slow-Starter Enzymes: Role of Active-Site Architecture in the Catalytic Control of the Biosynthesis of Taxadiene by Taxadiene Synthase
journal, May 2018
- Ansbacher, Tamar; Freud, Yehoshua; Major, Dan Thomas
- Biochemistry, Vol. 57, Issue 26
Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits
journal, May 2013
- Gutensohn, Michael; Orlova, Irina; Nguyen, Thuong T. H.
- The Plant Journal, Vol. 75, Issue 3
A Single Residue Switch for Mg 2+ -dependent Inhibition Characterizes Plant Class II Diterpene Cyclases from Primary and Secondary Metabolism
journal, April 2010
- Mann, Francis M.; Prisic, Sladjana; Davenport, Emily K.
- Journal of Biological Chemistry, Vol. 285, Issue 27
A Copal-8-ol Diphosphate Synthase from the Angiosperm Cistus creticus subsp. creticus Is a Putative Key Enzyme for the Formation of Pharmacologically Active, Oxygen-Containing Labdane-Type Diterpenes
journal, July 2010
- Falara, Vasiliki; Pichersky, Eran; Kanellis, Angelos K.
- Plant Physiology, Vol. 154, Issue 1
Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): Functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1)
journal, August 2006
- Ro, Dae-Kyun; Bohlmann, Jörg
- Phytochemistry, Vol. 67, Issue 15
CYP701A8: A Rice ent -Kaurene Oxidase Paralog Diverted to More Specialized Diterpenoid Metabolism
journal, January 2012
- Wang, Qiang; Hillwig, Matthew L.; Wu, Yisheng
- Plant Physiology, Vol. 158, Issue 3
Plant diterpene synthases: exploring modularity and metabolic diversity for bioengineering
journal, July 2015
- Zerbe, Philipp; Bohlmann, Jörg
- Trends in Biotechnology, Vol. 33, Issue 7
Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of the Salvia divinorum clerodienyl diphosphate synthase
journal, February 2017
- Pelot, Kyle A.; Mitchell, Rod; Kwon, Moonhyuk
- The Plant Journal, Vol. 89, Issue 5
Cloning of a Full-length cDNA Encoding ent -Kaurene Synthase from Gibberella fujikuroi : Functional Analysis of a Bifunctional Diterpene Cyclase
journal, January 2000
- Toyomasu, Tomonobu; Kawaide, Hiroshi; Ishizaki, Atsuko
- Bioscience, Biotechnology, and Biochemistry, Vol. 64, Issue 3
The MutT Proteins or “Nudix” Hydrolases, a Family of Versatile, Widely Distributed, “Housecleaning” Enzymes
journal, October 1996
- Bessman, Maurice J.; Frick, David N.; O'Handley, Suzanne F.
- Journal of Biological Chemistry, Vol. 271, Issue 41
Microbial engineering for the production of advanced biofuels
journal, August 2012
- Peralta-Yahya, Pamela P.; Zhang, Fuzhong; del Cardayre, Stephen B.
- Nature, Vol. 488, Issue 7411
A Novel Pathway for Sesquiterpene Biosynthesis from Z,Z -Farnesyl Pyrophosphate in the Wild Tomato Solanum habrochaites
journal, January 2009
- Sallaud, Christophe; Rontein, Denis; Onillon, Sandrine
- The Plant Cell, Vol. 21, Issue 1
Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis
journal, January 2016
- Andersen-Ranberg, Johan; Kongstad, Kenneth Thermann; Nielsen, Morten Thrane
- Angewandte Chemie International Edition, Vol. 55, Issue 6
Silencing the lettuce homologs of small rubber particle protein does not influence natural rubber biosynthesis in lettuce (Lactuca sativa)
journal, May 2015
- Chakrabarty, Romit; Qu, Yang; Ro, Dae-Kyun
- Phytochemistry, Vol. 113
Discovery of a metabolic alternative to the classical mevalonate pathway
journal, December 2013
- Dellas, Nikki; Thomas, Suzanne T.; Manning, Gerard
- eLife, Vol. 2
A P450-centric view of plant evolution: P450-centric evolution
journal, March 2011
- Nelson, David; Werck-Reichhart, Danièle
- The Plant Journal, Vol. 66, Issue 1
Biochemical and Molecular Genetic Aspects of Floral Scents
journal, March 2000
- Dudareva, Natalia; Pichersky, Eran
- Plant Physiology, Vol. 122, Issue 3
Structure, function and inhibition of ent-kaurene synthase from Bradyrhizobium japonicum
journal, October 2014
- Liu, Wenting; Feng, Xinxin; Zheng, Yingying
- Scientific Reports, Vol. 4, Issue 1
Functional diversity of 2-oxoglutarate/Fe(II)-dependent dioxygenases in plant metabolism
journal, October 2014
- Farrow, Scott C.; Facchini, Peter J.
- Frontiers in Plant Science, Vol. 5
Gibberellin biosynthesis in bacteria: Separate ent -copalyl diphosphate and ent -kaurene synthases in Bradyrhizobium japonicum
journal, December 2008
- Morrone, Dana; Chambers, Jacob; Lowry, Luke
- FEBS Letters, Vol. 583, Issue 2
A Third Class: Functional Gibberellin Biosynthetic Operon in Beta-Proteobacteria
journal, November 2018
- Nagel, Raimund; Bieber, John E.; Schmidt-Dannert, Mark G.
- Frontiers in Microbiology, Vol. 9
Hedycaryol Synthase in Complex with Nerolidol Reveals Terpene Cyclase Mechanism
journal, January 2014
- Baer, Philipp; Rabe, Patrick; Citron, Christian A.
- ChemBioChem, Vol. 15, Issue 2
Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane
journal, July 2003
- Bick, Julie Ann; Lange, B. Markus
- Archives of Biochemistry and Biophysics, Vol. 415, Issue 2
Evolution of Conifer Diterpene Synthases: Diterpene Resin Acid Biosynthesis in Lodgepole Pine and Jack Pine Involves Monofunctional and Bifunctional Diterpene Synthases
journal, December 2012
- Hall, Dawn E.; Zerbe, Philipp; Jancsik, Sharon
- Plant Physiology, Vol. 161, Issue 2
Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare
journal, July 2014
- Zerbe, Philipp; Chiang, Angela; Dullat, Harpreet
- The Plant Journal, Vol. 79, Issue 6
Molecular Cloning, Expression, and Functional Analysis of a cis -Prenyltransferase from Arabidopsis thaliana : IMPLICATIONS IN RUBBER BIOSYNTHESIS
journal, April 2000
- Oh, Soo Kyung; Han, Kyung Hwan; Ryu, Stephen B.
- Journal of Biological Chemistry, Vol. 275, Issue 24
Plant P450s as versatile drivers for evolution of species-specific chemical diversity
journal, February 2013
- Hamberger, Björn; Bak, Søren
- Philosophical Transactions of the Royal Society B: Biological Sciences, Vol. 368, Issue 1612
De novo formation of an aggregation pheromone precursor by an isoprenyl diphosphate synthase-related terpene synthase in the harlequin bug
journal, August 2018
- Lancaster, Jason; Khrimian, Ashot; Young, Sharon
- Proceedings of the National Academy of Sciences, Vol. 115, Issue 37
Identification in Haloferax volcanii of Phosphomevalonate Decarboxylase and Isopentenyl Phosphate Kinase as Catalysts of the Terminal Enzyme Reactions in an Archaeal Alternate Mevalonate Pathway
journal, December 2013
- VanNice, J. C.; Skaff, D. A.; Keightley, A.
- Journal of Bacteriology, Vol. 196, Issue 5
Isoprenoid biosynthesis in Archaea – Biochemical and evolutionary implications
journal, January 2011
- Matsumi, Rie; Atomi, Haruyuki; Driessen, Arnold J. M.
- Research in Microbiology, Vol. 162, Issue 1, p. 39-52
Biosynthesis of the oxygenated diterpene nezukol in the medicinal plant Isodon rubescens is catalyzed by a pair of diterpene synthases
journal, April 2017
- Pelot, Kyle A.; Hagelthorn, Lynne M.; Addison, J. Bennett
- PLOS ONE, Vol. 12, Issue 4
From The Cover: The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers
journal, January 2005
- Dudareva, N.; Andersson, S.; Orlova, I.
- Proceedings of the National Academy of Sciences, Vol. 102, Issue 3
Computational-guided discovery and characterization of a sesquiterpene synthase from Streptomyces clavuligerus
journal, April 2015
- Chow, Jeng-Yeong; Tian, Bo-Xue; Ramamoorthy, Gurusankar
- Proceedings of the National Academy of Sciences, Vol. 112, Issue 18
Identification of amino acid networks governing catalysis in the closed complex of class I terpene synthases
journal, February 2016
- Schrepfer, Patrick; Buettner, Alexander; Goerner, Christian
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 8
A Tandem Array of ent -Kaurene Synthases in Maize with Roles in Gibberellin and More Specialized Metabolism
journal, November 2015
- Fu, Jingye; Ren, Fei; Lu, Xuan
- Plant Physiology, Vol. 170, Issue 2
Mutational analysis of white spruce (Picea glauca) ent-kaurene synthase (PgKS) reveals common and distinct mechanisms of conifer diterpene synthases of general and specialized metabolism
journal, February 2012
- Zerbe, Philipp; Chiang, Angela; Bohlmann, Jörg
- Phytochemistry, Vol. 74
Biosynthesis, elicitation and roles of monocot terpenoid phytoalexins
journal, March 2014
- Schmelz, Eric A.; Huffaker, Alisa; Sims, James W.
- The Plant Journal, Vol. 79, Issue 4
Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential
journal, February 2006
- Gross, Harald; König, Gabriele M.
- Phytochemistry Reviews, Vol. 5, Issue 1
Contribution of isopentenyl phosphate to plant terpenoid metabolism
journal, August 2018
- Henry, Laura K.; Thomas, Suzanne T.; Widhalm, Joshua R.
- Nature Plants, Vol. 4, Issue 9
Terpenoid Synthases—From Chemical Ecology and Forest Fires to Biofuels and Bioproducts
journal, December 2011
- Bohlmann, Joerg
- Structure, Vol. 19, Issue 12
The essence of being extremophilic: the role of the unique archaeal membrane lipids
journal, August 1998
- van de Vossenberg, Jack L. C. M.; Driessen, Arnold J. M.; Konings, W. N.
- Extremophiles, Vol. 2, Issue 3
Plant diterpenoid metabolism for manufacturing the biopharmaceuticals of tomorrow: prospects and challenges
journal, May 2017
- Mafu, Sibongile; Zerbe, Philipp
- Phytochemistry Reviews, Vol. 17, Issue 1
Heterologous Expression and Characterization of a “Pseudomature” Form of Taxadiene Synthase Involved in Paclitaxel (Taxol) Biosynthesis and Evaluation of a Potential Intermediate and Inhibitors of the Multistep Diterpene Cyclization Reaction
journal, July 2000
- Williams, David C.; Wildung, Mark R.; Jin, Alan Qingwu
- Archives of Biochemistry and Biophysics, Vol. 379, Issue 1
Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes
journal, May 2014
- Brückner, Kathleen; Božić, Dragana; Manzano, David
- Phytochemistry, Vol. 101
The terpene synthase gene family in Tripterygium wilfordii harbors a labdane-type diterpene synthase among the monoterpene synthase TPS-b subfamily
journal, February 2017
- Hansen, Nikolaj L.; Heskes, Allison M.; Hamberger, Britta
- The Plant Journal, Vol. 89, Issue 3
Plasticity and Evolution of (+)-3-Carene Synthase and (−)-Sabinene Synthase Functions of a Sitka Spruce Monoterpene Synthase Gene Family Associated with Weevil Resistance
journal, July 2014
- Roach, Christopher R.; Hall, Dawn E.; Zerbe, Philipp
- Journal of Biological Chemistry, Vol. 289, Issue 34
Formation of Monoterpenes in Antirrhinum majus and Clarkia breweri Flowers Involves Heterodimeric Geranyl Diphosphate Synthases
journal, March 2004
- Tholl, Dorothea; Kish, Christine M.; Orlova, Irina
- The Plant Cell, Vol. 16, Issue 4
Nonlinear partial differential equations and applications: Bornyl diphosphate synthase: Structure and strategy for carbocation manipulation by a terpenoid cyclase
journal, November 2002
- Whittington, D. A.; Wise, M. L.; Urbansky, M.
- Proceedings of the National Academy of Sciences, Vol. 99, Issue 24
CYP76M7 Is an ent -Cassadiene C11α-Hydroxylase Defining a Second Multifunctional Diterpenoid Biosynthetic Gene Cluster in Rice
journal, October 2009
- Swaminathan, Sivakumar; Morrone, Dana; Wang, Qiang
- The Plant Cell, Vol. 21, Issue 10
HpDTC1, a Stress-Inducible Bifunctional Diterpene Cyclase Involved in Momilactone Biosynthesis, Functions in Chemical Defence in the Moss Hypnum plumaeforme
journal, May 2016
- Okada, Kazunori; Kawaide, Hiroshi; Miyamoto, Koji
- Scientific Reports, Vol. 6, Issue 1
A Novel Labda-7,13E-dien-15-ol-Producing Bifunctional Diterpene Synthase from Selaginella moellendorffii
journal, July 2011
- Mafu, Sibongile; Hillwig, Matthew L.; Peters, Reuben J.
- ChemBioChem, Vol. 12, Issue 13
CYP725A4 from Yew Catalyzes Complex Structural Rearrangement of Taxa-4(5),11(12)-diene into the Cyclic Ether 5(12)-Oxa-3(11)-cyclotaxane
journal, December 2007
- Rontein, Denis; Onillon, Sandrine; Herbette, Gaëtan
- Journal of Biological Chemistry, Vol. 283, Issue 10
Crystal Structure of Human Squalene Synthase: A KEY ENZYME IN CHOLESTEROL BIOSYNTHESIS
journal, July 2000
- Pandit, Jayvardhan; Danley, Dennis E.; Schulte, Gayle K.
- Journal of Biological Chemistry, Vol. 275, Issue 39
Functional characterization of the rice kaurene synthase-like gene family
journal, February 2007
- Xu, Meimei; Ross Wilderman, P.; Morrone, Dana
- Phytochemistry, Vol. 68, Issue 3
Total biosynthesis of the cyclic AMP booster forskolin from Coleus forskohlii
journal, March 2017
- Pateraki, Irini; Andersen-Ranberg, Johan; Jensen, Niels Bjerg
- eLife, Vol. 6
Substitution of Two Active-Site Residues Alters C9-Hydroxylation in a Class II Diterpene Synthase
journal, October 2016
- Mafu, Sibongile; Fischer, Emil; Addison, J. Bennett
- ChemBioChem, Vol. 17, Issue 24
The Application of Synthetic Biology to Elucidation of Plant Mono-, Sesqui-, and Diterpenoid Metabolism
journal, January 2015
- Kitaoka, Naoki; Lu, Xuan; Yang, Bing
- Molecular Plant, Vol. 8, Issue 1
The terpenoid theory of the origin of cellular life: the evolution of terpenoids to cholesterol
journal, September 1994
- Ourisson, Guy; Nakatani, Yoichi
- Chemistry & Biology, Vol. 1, Issue 1
Probing the Role of the DXDD Motif in Class II Diterpene Cyclases
journal, May 2007
- Prisic, Sladjana; Xu, Jianjun; Coates, Robert M.
- ChemBioChem, Vol. 8, Issue 8
Terpene synthases and the regulation, diversity and biological roles of terpene metabolism
journal, June 2006
- Tholl, Dorothea
- Current Opinion in Plant Biology, Vol. 9, Issue 3
Production of Bioactive Diterpenoids in the Euphorbiaceae Depends on Evolutionarily Conserved Gene Clusters
journal, August 2014
- King, Andrew J.; Brown, Geoffrey D.; Gilday, Alison D.
- The Plant Cell, Vol. 26, Issue 8
Abietadiene Synthase from Grand Fir ( Abies grandis ): Characterization and Mechanism of Action of the “Pseudomature” Recombinant Enzyme †
journal, December 2000
- Peters, Reuben J.; Flory, Janice E.; Jetter, Reinhard
- Biochemistry, Vol. 39, Issue 50
Genome-wide identification and characterization of novel genes involved in terpenoid biosynthesis in Salvia miltiorrhiza
journal, January 2012
- Ma, Yimian; Yuan, Lichai; Wu, Bin
- Journal of Experimental Botany, Vol. 63, Issue 7
Two residues determine the product profile of the class II diterpene synthases TPS14 and TPS21 of Tripterygium wilfordii
journal, June 2017
- Hansen, Nikolaj L.; Nissen, Jakob N.; Hamberger, Björn
- Phytochemistry, Vol. 138
Insights into Diterpene Cyclization from Structure of Bifunctional Abietadiene Synthase from Abies grandis
journal, January 2012
- Zhou, Ke; Gao, Yang; Hoy, Julie A.
- Journal of Biological Chemistry, Vol. 287, Issue 9
Towards a comprehensive understanding of the structural dynamics of a bacterial diterpene synthase during catalysis
journal, September 2018
- Driller, Ronja; Janke, Sophie; Fuchs, Monika
- Nature Communications, Vol. 9, Issue 1
Blocking Deprotonation with Retention of Aromaticity in a Plant ent -Copalyl Diphosphate Synthase Leads to Product Rearrangement
journal, November 2015
- Potter, Kevin C.; Zi, Jiachen; Hong, Young J.
- Angewandte Chemie International Edition, Vol. 55, Issue 2
Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana
journal, May 2003
- Laule, O.; Furholz, A.; Chang, H. -S.
- Proceedings of the National Academy of Sciences, Vol. 100, Issue 11
The function of terpene natural products in the natural world
journal, June 2007
- Gershenzon, Jonathan; Dudareva, Natalia
- Nature Chemical Biology, Vol. 3, Issue 7
Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining reveals convergent evolution
journal, July 2017
- Huang, Ancheng C.; Kautsar, Satria A.; Hong, Young J.
- Proceedings of the National Academy of Sciences, Vol. 114, Issue 29
The Primary Diterpene Synthase Products of Picea abies Levopimaradiene/Abietadiene Synthase (PaLAS) Are Epimers of a Thermally Unstable Diterpenol
journal, April 2011
- Keeling, Christopher I.; Madilao, Lina L.; Zerbe, Philipp
- Journal of Biological Chemistry, Vol. 286, Issue 24
Microbial-type terpene synthase genes occur widely in nonseed land plants, but not in seed plants
journal, October 2016
- Jia, Qidong; Li, Guanglin; Köllner, Tobias G.
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 43
Terpenoid biomaterials
journal, May 2008
- Bohlmann, Jörg; Keeling, Christopher I.
- The Plant Journal, Vol. 54, Issue 4
The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom: Terpene synthase family
journal, March 2011
- Chen, Feng; Tholl, Dorothea; Bohlmann, Jörg
- The Plant Journal, Vol. 66, Issue 1
An annotated transcriptome of highly inbred Thuja plicata (Cupressaceae) and its utility for gene discovery of terpenoid biosynthesis and conifer defense
journal, April 2018
- Shalev, Tal J.; Yuen, Macaire M. S.; Gesell, Andreas
- Tree Genetics & Genomes, Vol. 14, Issue 3
Functional Diversity of Diterpene Synthases in the Biofuel Crop Switchgrass
journal, July 2018
- Pelot, Kyle A.; Chen, Ruibing; Hagelthorn, David M.
- Plant Physiology, Vol. 178, Issue 1
Unusual P450 reactions in plant secondary metabolism
journal, March 2011
- Mizutani, Masaharu; Sato, Fumihiko
- Archives of Biochemistry and Biophysics, Vol. 507, Issue 1
Gibberellin Biosynthetic Pathway in Gibberella fujikuroi: Evidence for a Gene Cluster
journal, December 1998
- Tudzynski, Bettina; Hölter, Katja
- Fungal Genetics and Biology, Vol. 25, Issue 3, p. 157-170
Cloning and Characterization of Ginkgo biloba Levopimaradiene Synthase, Which Catalyzes the First Committed Step in Ginkgolide Biosynthesis
journal, August 2001
- Schepmann, Hala G.; Pang, Jihai; Matsuda, Seiichi P. T.
- Archives of Biochemistry and Biophysics, Vol. 392, Issue 2
Allelopathic potential of Tagetes minuta terpenes by a chemical, anatomical and phytotoxic approach
journal, December 2008
- López, M. Liza; Bonzani, Norma E.; Zygadlo, Julio A.
- Biochemical Systematics and Ecology, Vol. 36, Issue 12
Geranyllinalool Synthases in Solanaceae and Other Angiosperms Constitute an Ancient Branch of Diterpene Synthases Involved in the Synthesis of Defensive Compounds
journal, July 2014
- Falara, Vasiliki; Alba, Juan M.; Kant, Merijn R.
- Plant Physiology, Vol. 166, Issue 1
Biosynthesis via carbocations: Theoretical studies on terpene formation
journal, January 2011
- Tantillo, Dean J.
- Natural Product Reports, Vol. 28, Issue 6
Functional identification of rice syn -copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products
journal, August 2004
- Xu, Meimei; Hillwig, Matthew L.; Prisic, Sladjana
- The Plant Journal, Vol. 39, Issue 3
Biological functions of ent - and syn -copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis
journal, September 2004
- Otomo, Kazuko; Kenmoku, Hiromichi; Oikawa, Hideaki
- The Plant Journal, Vol. 39, Issue 6
A (–)-kolavenyl diphosphate synthase catalyzes the first step of salvinorin A biosynthesis in Salvia divinorum
journal, February 2017
- Chen, Xiaoyue; Berim, Anna; Dayan, Franck E.
- Journal of Experimental Botany, Vol. 68, Issue 5
Toward a Biosynthetic Route to Sclareol and Amber Odorants
journal, November 2012
- Schalk, Michel; Pastore, Laurence; Mirata, Marco A.
- Journal of the American Chemical Society, Vol. 134, Issue 46
Improving peppermint essential oil yield and composition by metabolic engineering
journal, September 2011
- Lange, B. M.; Mahmoud, S. S.; Wildung, M. R.
- Proceedings of the National Academy of Sciences, Vol. 108, Issue 41
Trichome specific expression of the tobacco (Nicotiana sylvestris) cembratrien-ol synthase genes is controlled by both activating and repressing cis-regions
journal, May 2010
- Ennajdaoui, Hanane; Vachon, Gilles; Giacalone, Cécile
- Plant Molecular Biology, Vol. 73, Issue 6
MTPSLs: New Terpene Synthases in Nonseed Plants
journal, February 2018
- Jia, Qidong; Köllner, Tobias G.; Gershenzon, Jonathan
- Trends in Plant Science, Vol. 23, Issue 2
Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis
journal, April 2012
- Smanski, Michael J.; Peterson, Ryan M.; Huang, Sheng-Xiong
- Current Opinion in Chemical Biology, Vol. 16, Issue 1-2
Enzymatic 13 C Labeling and Multidimensional NMR Analysis of Miltiradiene Synthesized by Bifunctional Diterpene Cyclase in Selaginella moellendorffii
journal, October 2011
- Sugai, Yoshinori; Ueno, Yohei; Hayashi, Ken-ichiro
- Journal of Biological Chemistry, Vol. 286, Issue 50
Rational Conversion of Substrate and Product Specificity in a Salvia Monoterpene Synthase: Structural Insights into the Evolution of Terpene Synthase Function
journal, June 2007
- Kampranis, Sotirios C.; Ioannidis, Daphne; Purvis, Alan
- The Plant Cell, Vol. 19, Issue 6
Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase
journal, May 2005
- Ro, D. -K.; Arimura, G. -I.; Lau, S. Y. W.
- Proceedings of the National Academy of Sciences, Vol. 102, Issue 22
Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals
journal, December 2012
- Zhou, Ke; Xu, Meimei; Tiernan, Mollie
- Phytochemistry, Vol. 84
The carbocation continuum in terpene biosynthesis—where are the secondary cations?
journal, January 2010
- Tantillo, Dean J.
- Chemical Society Reviews, Vol. 39, Issue 8
Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals
journal, December 2012
- Wu, Yisheng; Zhou, Ke; Toyomasu, Tomonobu
- Phytochemistry, Vol. 84
Functional Annotation, Genome Organization and Phylogeny of the Grapevine (Vitis vinifera) Terpene Synthase Gene Family Based on Genome Assembly, FLcDNA Cloning, and Enzyme Assays
journal, January 2010
- Martin, Diane M.; Aubourg, Sébastien; Schouwey, Marina B.
- BMC Plant Biology, Vol. 10, Issue 1
Novel Product Chemistry from Mechanistic Analysis of ent -Copalyl Diphosphate Synthases from Plant Hormone Biosynthesis
journal, May 2014
- Potter, Kevin; Criswell, Jared; Zi, Jiachen
- Angewandte Chemie International Edition, Vol. 53, Issue 28
Gene Discovery of Modular Diterpene Metabolism in Nonmodel Systems
journal, April 2013
- Zerbe, Philipp; Hamberger, Björn; Yuen, Macaire M. S.
- Plant Physiology, Vol. 162, Issue 2
Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis
journal, September 2016
- Jia, Meirong; Potter, Kevin C.; Peters, Reuben J.
- Metabolic Engineering, Vol. 37
Synthesizing specificity: multiple approaches to understanding the attack and defense of plants
journal, May 2012
- Agrawal, Anurag A.; Heil, Martin
- Trends in Plant Science, Vol. 17, Issue 5
Discovery, Biosynthesis and Stress-Related Accumulation of Dolabradiene-Derived Defenses in Maize
journal, February 2018
- Mafu, Sibongile; Ding, Yezhang; Murphy, Katherine M.
- Plant Physiology, Vol. 176, Issue 4
Investigating the Phylogenetic Range of Gibberellin Biosynthesis in Bacteria
journal, April 2017
- Nagel, Raimund; Peters, Reuben J.
- Molecular Plant-Microbe Interactions, Vol. 30, Issue 4
Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate
journal, June 2009
- Schilmiller, A. L.; Schauvinhold, I.; Larson, M.
- Proceedings of the National Academy of Sciences, Vol. 106, Issue 26
Exploring diterpene metabolism in non-model species: transcriptome-enabled discovery and functional characterization of labda-7,13 E -dienyl diphosphate synthase from Grindelia robusta
journal, July 2015
- Zerbe, Philipp; Rodriguez, Selina M.; Mafu, Sibongile
- The Plant Journal, Vol. 83, Issue 5
Crystal structure of CYP76AH1 in 4-PI-bound state from Salvia miltiorrhiza
journal, April 2019
- Gu, Mingyue; Wang, Mingzhu; Guo, Juan
- Biochemical and Biophysical Research Communications, Vol. 511, Issue 4
Traversing the fungal terpenome
journal, January 2014
- Quin, Maureen B.; Flynn, Christopher M.; Schmidt-Dannert, Claudia
- Nat. Prod. Rep., Vol. 31, Issue 10
Biotechnological production of natural zero-calorie sweeteners
journal, April 2014
- Philippe, Ryan N.; De Mey, Marjan; Anderson, Jeff
- Current Opinion in Biotechnology, Vol. 26
A Lettuce ( Lactuca sativa ) Homolog of Human Nogo-B Receptor Interacts with cis -Prenyltransferase and Is Necessary for Natural Rubber Biosynthesis
journal, December 2014
- Qu, Yang; Chakrabarty, Romit; Tran, Hue T.
- Journal of Biological Chemistry, Vol. 290, Issue 4
X-ray Crystallographic Studies of Substrate Binding to Aristolochene Synthase Suggest a Metal Ion Binding Sequence for Catalysis
journal, April 2008
- Shishova, Ekaterina Y.; Yu, Fanglei; Miller, David J.
- Journal of Biological Chemistry, Vol. 283, Issue 22
A raison d’être for two distinct pathways in the early steps of plant isoprenoid biosynthesis?
journal, April 2012
- Hemmerlin, Andréa; Harwood, John L.; Bach, Thomas J.
- Progress in Lipid Research, Vol. 51, Issue 2
Cloning of casbene and neocembrene synthases from Euphorbiaceae plants and expression in Saccharomyces cerevisiae
journal, September 2010
- Kirby, James; Nishimoto, Minobu; Park, J. Genevieve
- Phytochemistry, Vol. 71, Issue 13
Cytochrome P450 enzymes: A driving force of plant diterpene diversity
journal, May 2019
- Bathe, Ulschan; Tissier, Alain
- Phytochemistry, Vol. 161
The tomato cis- prenyltransferase gene family
journal, December 2012
- Akhtar, Tariq A.; Matsuba, Yuki; Schauvinhold, Ines
- The Plant Journal, Vol. 73, Issue 4
Diterpene Synthase‐Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers
journal, November 2018
- Pelot, Kyle A.; Hagelthorn, David M.; Hong, Young J.
- ChemBioChem, Vol. 20, Issue 1
A Pair of Residues That Interactively Affect Diterpene Synthase Product Outcome
journal, February 2017
- Jia, Meirong; Zhou, Ke; Tufts, Samuel
- ACS Chemical Biology, Vol. 12, Issue 3
Characterization of the kaurene oxidase CYP701A3, a multifunctional cytochrome P450 from gibberellin biosynthesis
journal, October 2010
- Morrone, Dana; Chen, Xiaoming; Coates, Robert M.
- Biochemical Journal, Vol. 431, Issue 3
Geranyl diphosphate synthase: Cloning, expression, and characterization of this prenyltransferase as a heterodimer
journal, November 1999
- Burke, C. C.; Wildung, M. R.; Croteau, R.
- Proceedings of the National Academy of Sciences, Vol. 96, Issue 23
Origins and Early Evolution of the Mevalonate Pathway of Isoprenoid Biosynthesis in the Three Domains of Life
journal, July 2010
- Lombard, J.; Moreira, D.
- Molecular Biology and Evolution, Vol. 28, Issue 1
Uptake of isopentenyl diphosphate by plastids isolated from Vitis vinifera L. cell suspensions
journal, August 1993
- Soler, E.; Clastre, M.; Bantignies, B.
- Planta, Vol. 191, Issue 3
Following evolution's lead to a single residue switch for diterpene synthase product outcome
journal, April 2007
- Xu, M.; Wilderman, P. R.; Peters, R. J.
- Proceedings of the National Academy of Sciences, Vol. 104, Issue 18
Parsing a multifunctional biosynthetic gene cluster from rice: Biochemical characterization of CYP71Z6 & 7
journal, October 2011
- Wu, Yisheng; Hillwig, Matthew L.; Wang, Qiang
- FEBS Letters, Vol. 585, Issue 21
Gene Networks Underlying Cannabinoid and Terpenoid Accumulation in Cannabis
journal, May 2019
- Zager, Jordan J.; Lange, Iris; Srividya, Narayanan
- Plant Physiology, Vol. 180, Issue 4
Synthetic biology and the development of tools for metabolic engineering
journal, May 2012
- Keasling, Jay D.
- Metabolic Engineering, Vol. 14, Issue 3
Biosynthesis of bioactive diterpenoids in the medicinal plant Vitex agnus‐castus
journal, February 2018
- Heskes, Allison M.; Sundram, Tamil C. M.; Boughton, Berin A.
- The Plant Journal, Vol. 93, Issue 5
Crystal Structure of (+)-δ-Cadinene Synthase from Gossypium arboreum and Evolutionary Divergence of Metal Binding Motifs for Catalysis
journal, July 2009
- Gennadios, Heather A.; Gonzalez, Veronica; Di Costanzo, Luigi
- Biochemistry, Vol. 48, Issue 26
The chemical logic of plant natural product biosynthesis
journal, June 2014
- Anarat-Cappillino, Gülbenk; Sattely, Elizabeth S.
- Current Opinion in Plant Biology, Vol. 19
Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture
journal, January 2012
- Caniard, Anne; Zerbe, Philipp; Legrand, Sylvain
- BMC Plant Biology, Vol. 12, Issue 1
Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens
journal, October 2006
- Hayashi, Ken-ichiro; Kawaide, Hiroshi; Notomi, Miho
- FEBS Letters, Vol. 580, Issue 26
Changing Face: A Key Residue for the Addition of Water by Sclareol Synthase
journal, March 2018
- Jia, Meirong; O’Brien, Terrence E.; Zhang, Yue
- ACS Catalysis, Vol. 8, Issue 4
Characterization of CYP71Z18 indicates a role in maize zealexin biosynthesis
journal, January 2016
- Mao, Hongjie; Liu, Jiang; Ren, Fei
- Phytochemistry, Vol. 121
1.55Å-resolution structure of ent-copalyl diphosphate synthase and exploration of general acid function by site-directed mutagenesis
journal, January 2014
- Köksal, Mustafa; Potter, Kevin; Peters, Reuben J.
- Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 1840, Issue 1
Oxidation and cyclization of casbene in the biosynthesis of Euphorbia factors from mature seeds of Euphorbia lathyris L.
journal, August 2016
- Luo, Dan; Callari, Roberta; Hamberger, Britta
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 34
Efficient heterocyclisation by (di)terpene synthases
journal, January 2015
- Mafu, S.; Potter, K. C.; Hillwig, M. L.
- Chemical Communications, Vol. 51, Issue 70
A Single Residue Change Leads to a Hydroxylated Product from the Class II Diterpene Cyclization Catalyzed by Abietadiene Synthase
journal, November 2012
- Criswell, Jared; Potter, Kevin; Shephard, Freya
- Organic Letters, Vol. 14, Issue 23
Terpenoid synthase structures: a so far incomplete view of complex catalysis
journal, January 2012
- Gao, Yang; Honzatko, Richard B.; Peters, Reuben J.
- Natural Product Reports, Vol. 29, Issue 10
Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast
journal, October 2016
- Scheler, Ulschan; Brandt, Wolfgang; Porzel, Andrea
- Nature Communications, Vol. 7, Issue 1
Domain loss has independently occurred multiple times in plant terpene synthase evolution: Complex evolutionary origins for terpene synthases
journal, October 2011
- Hillwig, Matthew L.; Xu, Meimei; Toyomasu, Tomonobu
- The Plant Journal, Vol. 68, Issue 6
Gibberellin biosynthesis in fungi: genes, enzymes, evolution, and impact on biotechnology
journal, December 2004
- Tudzynski, Bettina
- Applied Microbiology and Biotechnology, Vol. 66, Issue 6
Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals
journal, April 2011
- Morrone, Dana; Hillwig, Matthew L.; Mead, Matthew E.
- Biochemical Journal, Vol. 435, Issue 3
Isoprenoid biosynthesis: The evolution of two ancient and distinct pathways across genomes
journal, November 2000
- Lange, B. M.; Rujan, T.; Martin, W.
- Proceedings of the National Academy of Sciences, Vol. 97, Issue 24
High-level semi-synthetic production of the potent antimalarial artemisinin
journal, April 2013
- Paddon, C. J.; Westfall, P. J.; Pitera, D. J.
- Nature, Vol. 496, Issue 7446
Catalytic Bases and Stereocontrol in Lamiaceae Class II Diterpene Cyclases
journal, May 2018
- Schulte, Samuel; Potter, Kevin C.; Lemke, Cody
- Biochemistry, Vol. 57, Issue 25
Evolution of Diterpene Metabolism: Sitka Spruce CYP720B4 Catalyzes Multiple Oxidations in Resin Acid Biosynthesis of Conifer Defense against Insects
journal, October 2011
- Hamberger, Björn; Ohnishi, Toshiyuki; Hamberger, Britta
- Plant Physiology, Vol. 157, Issue 4
Terpenoid biosynthesis in trichomes-current status and future opportunities
journal, September 2012
- Markus Lange, B.; Turner, Glenn W.
- Plant Biotechnology Journal, Vol. 11, Issue 1
Functional analysis of (4 S )-limonene synthase mutants reveals determinants of catalytic outcome in a model monoterpene synthase
journal, March 2015
- Srividya, Narayanan; Davis, Edward M.; Croteau, Rodney B.
- Proceedings of the National Academy of Sciences, Vol. 112, Issue 11
Biosynthesis of Sandalwood Oil: Santalum album CYP76F Cytochromes P450 Produce Santalols and Bergamotol
journal, September 2013
- Diaz-Chavez, Maria L.; Moniodis, Jessie; Madilao, Lufiani L.
- PLoS ONE, Vol. 8, Issue 9
Transport of Isoprenoid Intermediates Across Chloroplast Envelope Membranes
journal, January 2005
- Flügge, U. ‐I.; Gao, W.
- Plant Biology, Vol. 7, Issue 1
Diversity, regulation, and evolution of the gibberellin biosynthetic pathway in fungi compared to plants and bacteria
journal, October 2009
- Bömke, Christiane; Tudzynski, Bettina
- Phytochemistry, Vol. 70, Issue 15-16
Unearthing the roots of the terpenome
journal, April 2008
- Christianson, David W.
- Current Opinion in Chemical Biology, Vol. 12, Issue 2
CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts
journal, June 2013
- Guo, J.; Zhou, Y. J.; Hillwig, M. L.
- Proceedings of the National Academy of Sciences, Vol. 110, Issue 29
Diterpene resin acids in conifers
journal, November 2006
- Keeling, Christopher I.; Bohlmann, Jörg
- Phytochemistry, Vol. 67, Issue 22
Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants.
journal, August 1994
- Mau, C. J.; West, C. A.
- Proceedings of the National Academy of Sciences, Vol. 91, Issue 18
Integrative analysis of transcript and metabolite profiling data sets to evaluate the regulation of biochemical pathways during photomorphogenesis
journal, April 2006
- Ghassemian, Majid; Lutes, Jason; Tepperman, James M.
- Archives of Biochemistry and Biophysics, Vol. 448, Issue 1-2
Combining metabolomics and transcriptomics to characterize tanshinone biosynthesis in Salvia miltiorrhiza
journal, January 2014
- Gao, Wei; Sun, Hai-Xi; Xiao, Hongbin
- BMC Genomics, Vol. 15, Issue 1
Metabolic cross-talk between pathways of terpenoid backbone biosynthesis in spike lavender
journal, October 2015
- Mendoza-Poudereux, Isabel; Kutzner, Erika; Huber, Claudia
- Plant Physiology and Biochemistry, Vol. 95
Accumulation of terpenoid phytoalexins in maize roots is associated with drought tolerance: Maize root phytoalexins play a role in drought tolerance
journal, January 2015
- Vaughan, Martha M.; Christensen, Shawn; Schmelz, Eric A.
- Plant, Cell & Environment, Vol. 38, Issue 11
Synthetic biology for microbial production of lipid-based biofuels
journal, December 2015
- d’Espaux, Leo; Mendez-Perez, Daniel; Li, Rachel
- Current Opinion in Chemical Biology, Vol. 29
The Gibberellin perception system evolved to regulate a pre-existing GAMYB-mediated system during land plant evolution
journal, September 2011
- Aya, Koichiro; Hiwatashi, Yuji; Kojima, Mikiko
- Nature Communications, Vol. 2, Issue 1
Catalytic control in terpenoid cyclases: multiscale modeling of thermodynamic, kinetic, and dynamic effects
journal, August 2014
- Major, Dan Thomas; Freud, Yehoshua; Weitman, Michal
- Current Opinion in Chemical Biology, Vol. 21
Biosynthesis of monoterpene scent compounds in roses
journal, July 2015
- Magnard, Jean-Louis; Roccia, Aymeric; Caissard, Jean-Claude
- Science, Vol. 349, Issue 6243
Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle
journal, March 2016
- Beran, Franziska; Rahfeld, Peter; Luck, Katrin
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 11
Cloning of a Gene Cluster Responsible for the Biosynthesis of Diterpene Aphidicolin, a Specific Inhibitor of DNA Polymerase α
journal, January 2004
- Toyomasu, Tomonobu; Nakaminami, Kentaro; Toshima, Hiroaki
- Bioscience, Biotechnology, and Biochemistry, Vol. 68, Issue 1
Comprehensive Analysis of Cytosolic Nudix Hydrolases in Arabidopsis thaliana
journal, May 2005
- Ogawa, Takahisa; Ueda, Yayoi; Yoshimura, Kazuya
- Journal of Biological Chemistry, Vol. 280, Issue 26
Defining the Product Chemical Space of Monoterpenoid Synthases
journal, August 2016
- Tian, Boxue; Poulter, C. Dale; Jacobson, Matthew P.
- PLOS Computational Biology, Vol. 12, Issue 8
A Red Algal Bourbonane Sesquiterpene Synthase Defined by Microgram-Scale NMR-Coupled Crystalline Sponge X-ray Diffraction Analysis
journal, November 2017
- Kersten, Roland D.; Lee, Shoukou; Fujita, Daishi
- Journal of the American Chemical Society, Vol. 139, Issue 46
The Role of Momilactones in Rice Allelopathy
journal, February 2013
- Kato-Noguchi, Hisashi; Peters, Reuben J.
- Journal of Chemical Ecology, Vol. 39, Issue 2
Terpene Biosynthesis in Red Algae Is Catalyzed by Microbial Type But Not Typical Plant Terpene Synthases
journal, December 2018
- Wei, Guo; Jia, Qidong; Chen, Xinlu
- Plant Physiology, Vol. 179, Issue 2
Glandular Trichomes of Leucosceptrum canum Harbor Defensive Sesterterpenoids
journal, June 2010
- Luo, Shi-Hong; Luo, Qian; Niu, Xue-Mei
- Angewandte Chemie International Edition, Vol. 49, Issue 26
Identification and Functional Characterization of Monofunctional ent -Copalyl Diphosphate and ent -Kaurene Synthases in White Spruce Reveal Different Patterns for Diterpene Synthase Evolution for Primary and Secondary Metabolism in Gymnosperms
journal, December 2009
- Keeling, Christopher I.; Dullat, Harpreet K.; Yuen, Mack
- Plant Physiology, Vol. 152, Issue 3
Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi
journal, February 2007
- Toyomasu, T.; Tsukahara, M.; Kaneko, A.
- Proceedings of the National Academy of Sciences, Vol. 104, Issue 9
Nonseed plant Selaginella moellendorffii has both seed plant and microbial types of terpene synthases
journal, August 2012
- Li, G.; Kollner, T. G.; Yin, Y.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 36
Bifunctional cis -Abienol Synthase from Abies balsamea Discovered by Transcriptome Sequencing and Its Implications for Diterpenoid Fragrance Production
journal, February 2012
- Zerbe, Philipp; Chiang, Angela; Yuen, Macaire
- Journal of Biological Chemistry, Vol. 287, Issue 15
Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase
journal, January 2017
- Mafu, Sibongile; Karunanithi, Prema Sambandaswami; Palazzo, Teresa Ann
- Proceedings of the National Academy of Sciences, Vol. 114, Issue 5