Plant Terpenoids: Biosynthesis and Ecological Functions

Among plant secondary metabolites terpenoids are a structurally most diverse group; they function as phytoalex- ins in plant direct defense, or as signals in indirect defense responses which involves herbivores and their natural enemies. In recent years, more and more attention has been paid to the investigation of the ecological role of plant terpenoids. The biosynthesis pathways of monoterpenes, sesquiterpenes, and diterpenes include the synthesis of C5 precursor isopentenyl diphosphate (IPP) and its allylic isomer dimethylallyl diphosphate (DMAPP), the synthe- sis of the immediate diphosphate precursors, and the formation of the diverse terpenoids. Terpene synthases (TPSs) play a key role in volatile terpene synthesis. By expression of the TPS genes, significant achievements have been made on metabolic engineering to increase terpenoid production. This review mainly summarizes the recent research progress in elucidating the ecological role of terpenoids and characterization of the enzymes involved in the terpenoid biosynthesis. Spatial and temporal regulations of terpenoids metabolism are also discussed.

[1]  D. Tholl.  Terpene synthases and the regulation, diversity and biological roles of terpene metabolism. , 2006, Current opinion in plant biology.

[2]  C. Kost,et al.  Herbivore‐induced plant volatiles induce an indirect defence in neighbouring plants , 2006 .

[3]  J. Gershenzon,et al.  The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[4]  I. Baldwin,et al.  Using 'mute' plants to translate volatile signals. , 2006, The Plant journal : for cell and molecular biology.

[5]  Lei Zhang,et al.  Characterization and expression profile analysis of a new cDNA encoding taxadiene synthase from Taxus media. , 2005, Journal of biochemistry and molecular biology.

[6]  A. Aharoni,et al.  Genetic Engineering of Terpenoid Metabolism Attracts Bodyguards to Arabidopsis , 2005, Science.

[7]  D. Llewellyn,et al.  Antisense Suppression of a (+)-δ-Cadinene Synthase Gene in Cotton Prevents the Induction of This Defense Response Gene during Bacterial Blight Infection But Not Its Constitutive Expression1[w] , 2005, Plant Physiology.

[8]  Ted C. J. Turlings,et al.  Recruitment of entomopathogenic nematodes by insect-damaged maize roots , 2005, Nature.

[9]  W. Boland,et al.  Effects of Feeding Spodoptera littoralis on Lima Bean Leaves. II. Continuous Mechanical Wounding Resembling Insect Feeding Is Sufficient to Elicit Herbivory-Related Volatile Emission , 2005, Plant Physiology.

[10]  M. Reichelt,et al.  The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[11]  J. Bohlmann,et al.  Insect-Induced Conifer Defense. White Pine Weevil and Methyl Jasmonate Induce Traumatic Resinosis, de Novo Formed Volatile Emissions, and Accumulation of Terpenoid Synthase and Putative Octadecanoid Pathway Transcripts in Sitka Spruce1[w] , 2005, Plant Physiology.

[12]  Meimei Xu,et al.  Rice Contains Two Disparate ent-Copalyl Diphosphate Synthases with Distinct Metabolic Functions1 , 2004, Plant Physiology.

[13]  J. Gershenzon,et al.  Biochemistry of Plant Volatiles1 , 2004, Plant Physiology.

[14]  Diane M. Martin,et al.  Functional Characterization of Nine Norway Spruce TPS Genes and Evolution of Gymnosperm Terpene Synthases of the TPS-d Subfamily1[w] , 2004, Plant Physiology.

[15]  J. Bohlmann,et al.  Herbivore-Induced Defense Response in a Model Legume. Two-Spotted Spider Mites Induce Emission of (E)-β-Ocimene and Transcript Accumulation of (E)-β-Ocimene Synthase in Lotus japonicus1 , 2004, Plant Physiology.

[16]  Marcel Dicke,et al.  Combined Transcript and Metabolite Analysis Reveals Genes Involved in Spider Mite Induced Volatile Formation in Cucumber Plants1 , 2004, Plant Physiology.

[17]  J. Gershenzon,et al.  The Variability of Sesquiterpenes Emitted from Two Zea mays Cultivars Is Controlled by Allelic Variation of Two Terpene Synthase Genes Encoding Stereoselective Multiple Product Enzymes , 2004, The Plant Cell Online.

[18]  Jia-Wei Wang,et al.  Characterization of GaWRKY1, a Cotton Transcription Factor That Regulates the Sesquiterpene Synthase Gene (+)-δ-Cadinene Synthase-A1 , 2004, Plant Physiology.

[19]  J. Gershenzon,et al.  Formation of Monoterpenes in Antirrhinum majus and Clarkia breweri Flowers Involves Heterodimeric Geranyl Diphosphate Synthases , 2004, The Plant Cell Online.

[20]  J. Bohlmann,et al.  Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa x deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (-)-germacrene D synthase, PtdTPS1. , 2004, The Plant journal : for cell and molecular biology.

[21]  C. Rodriguez‐Saona,et al.  Volatile Emissions Triggered by Multiple Herbivore Damage: Beet Armyworm and Whitefly Feeding on Cotton Plants , 2003, Journal of Chemical Ecology.

[22]  M. Dicke,et al.  Herbivore-Induced Volatile Production by Arabidopsis thaliana Leads to Attraction of the Parasitoid Cotesia rubecula: Chemical, Behavioral, and Gene-Expression Analysis , 2001, Journal of Chemical Ecology.

[23]  A. Aharoni,et al.  Terpenoid Metabolism in Wild-Type and Transgenic Arabidopsis Plants Online version contains Web-only data. Article, publication date, and citation information can be found at www.plantcell.org/cgi/doi/10.1105/tpc.016253. , 2003, The Plant Cell Online.

[24]  C. Poulter,et al.  Enzymes Encoded by the Farnesyl Diphosphate Synthase Gene Family in the Big Sagebrush Artemisia tridentata ssp. spiciformis* , 2003, Journal of Biological Chemistry.

[25]  A. Hemmerlin,et al.  Cross-talk between the Cytosolic Mevalonate and the Plastidial Methylerythritol Phosphate Pathways in Tobacco Bright Yellow-2 Cells* , 2003, Journal of Biological Chemistry.

[26]  Jörg Bohlmann,et al.  Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce1 , 2003, Plant Physiology.

[27]  A. Fürholz,et al.  Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[28]  Diane M. Martin,et al.  (E)-beta-ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: function and expression of three terpene synthase genes of a new terpene synthase subfamily. , 2003, The Plant cell.

[29]  J. Gershenzon,et al.  Attracting friends to feast on foes: engineering terpene emission to make crop plants more attractive to herbivore enemies. , 2003, Current opinion in biotechnology.

[30]  J. Gershenzon,et al.  Biosynthesis and Emission of Terpenoid Volatiles from Arabidopsis Flowers Article, publication date, and citation information can be found at www.plantcell.org/cgi/doi/10.1105/tpc.007989. , 2003, The Plant Cell Online.

[31]  J. Gershenzon,et al.  The Maize Gene terpene synthase 1 Encodes a Sesquiterpene Synthase Catalyzing the Formation of (E)-β-Farnesene, (E)-Nerolidol, and (E,E)-Farnesol after Herbivore Damage1 , 2002, Plant Physiology.

[32]  R. Croteau,et al.  A cDNA clone for β-caryophyllene synthase from Artemisia annua , 2002 .

[33]  Shan Lu,et al.  Cloning and Functional Characterization of a β-Pinene Synthase from Artemisia annua That Shows a Circadian Pattern of Expression1 , 2002, Plant Physiology.

[34]  S. Aubourg,et al.  Genomic analysis of the terpenoid synthase (AtTPS) gene family of Arabidopsis thaliana , 2002, Molecular Genetics and Genomics.

[35]  R. Croteau,et al.  Interaction with the Small Subunit of Geranyl Diphosphate Synthase Modifies the Chain Length Specificity of Geranylgeranyl Diphosphate Synthase to Produce Geranyl Diphosphate* , 2002, The Journal of Biological Chemistry.

[36]  X. Chen,et al.  Molecular cloning and functional identification of (+)-delta-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis. , 2001, The Plant journal : for cell and molecular biology.

[37]  Natalia Dudareva,et al.  Regulation of Circadian Methyl Benzoate Emission in Diurnally and Nocturnally Emitting Plants , 2001, The Plant Cell Online.

[38]  I. Baldwin,et al.  Defensive function of herbivore-induced plant volatile emissions in nature. , 2001, Science.

[39]  P. Gallusci,et al.  LEFPS1, a tomato farnesyl pyrophosphate gene highly expressed during early fruit development. , 2000, Plant physiology.

[40]  T. Nishioka,et al.  Involvement of jasmonate- and salicylate-related signaling pathways for the production of specific herbivore-induced volatiles in plants. , 2000, Plant & cell physiology.

[41]  J. Gershenzon,et al.  Regulation of monoterpene accumulation in leaves of peppermint. , 2000, Plant physiology.

[42]  C. Liu,et al.  Expression pattern of genes encoding farnesyl diphosphate synthase and sesquiterpene cyclase in cotton suspension-cultured cells treated with fungal elicitors. , 1999, Molecular plant-microbe interactions : MPMI.

[43]  R. Croteau,et al.  Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[44]  Hartmut K. Lichtenthaler,et al.  THE 1-DEOXY-D-XYLULOSE-5-PHOSPHATE PATHWAY OF ISOPRENOID BIOSYNTHESIS IN PLANTS. , 1999, Annual review of plant physiology and plant molecular biology.

[45]  Phillips,et al.  Resin-based defenses in conifers. , 1999, Trends in plant science.

[46]  T. Koyama,et al.  2.04 – Isopentenyl DiphosphateIsomerase and Prenyltransferases , 1999 .

[47]  J. Chappell,et al.  Isoprenoid biosynthesis in plants: carbon partitioning within the cytoplasmic pathway. , 1999, Critical reviews in biochemistry and molecular biology.

[48]  J. Bohlmann,et al.  Plant terpenoid synthases: molecular biology and phylogenetic analysis. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[49]  I. Alchanati,et al.  The enzymatic cyclization of nerolidyl diphosphate by δ-cadinene synthase from cotton stele tissue infected with verticillium dahliae , 1998 .

[50]  D. Cane,et al.  Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. , 1997, Science.

[51]  J. Tumlinson,et al.  De Novo Biosynthesis of Volatiles Induced by Insect Herbivory in Cotton Plants , 1997, Plant physiology.

[52]  J. B. Reid,et al.  The LS locus of pea encodes the gibberellin biosynthesis enzyme ent-kaurene synthase A. , 1997, The Plant journal : for cell and molecular biology.

[53]  R. Croteau,et al.  Abietadiene Synthase from Grand Fir (Abies grandis) cDNA ISOLATION, CHARACTERIZATION, AND BACTERIAL EXPRESSION OF A BIFUNCTIONAL DITERPENE CYCLASE INVOLVED IN RESIN ACID BIOSYNTHESIS* , 1996, The Journal of Biological Chemistry.

[54]  R. Croteau,et al.  A cDNA Clone for Taxadiene Synthase, the Diterpene Cyclase That Catalyzes the Committed Step of Taxol Biosynthesis , 1996, The Journal of Biological Chemistry.

[55]  F. Karst,et al.  Arabidopsis thaliana Contains Two Differentially Expressed Farnesyl-Diphosphate Synthase Genes (*) , 1996, The Journal of Biological Chemistry.

[56]  V. Davisson,et al.  Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis. , 1995, Archives of biochemistry and biophysics.

[57]  R. Croteau,et al.  4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. , 1993, The Journal of biological chemistry.

[58]  P. Facchini,et al.  Gene family for an elicitor-induced sesquiterpene cyclase in tobacco. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[59]  J. Chappell,et al.  Induction of sesquiterpene cyclase and suppression of squalene synthetase activities in plant cell cultures treated with fungal elicitor. , 1988, Plant physiology.