Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes

BMC Plant Biology

Volumn 9, Issue , 2009, Pages

  Göpfert, Jens C ^a   MacNevin, Gillian ^b   Ro, Dae Kyun ^b   Spring, Otmar ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ASTERACEAE; ESCHERICHIA COLI; HELIANTHUS; HELIANTHUS ANNUUS; SACCHAROMYCES CEREVISIAE;

LACTONE; PLANT RNA; SESQUITERPENE; TRANSFERASE; VEGETABLE PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; DNA SEQUENCE; ENZYMOLOGY; ESCHERICHIA COLI; FLOWER; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; MOLECULAR GENETICS; SACCHAROMYCES CEREVISIAE; SEQUENCE ALIGNMENT; SUNFLOWER;

ALKYL AND ARYL TRANSFERASES; AMINO ACID SEQUENCE; ESCHERICHIA COLI; FLOWERS; GENE EXPRESSION REGULATION, DEVELOPMENTAL; GENE EXPRESSION REGULATION, PLANT; HELIANTHUS; LACTONES; MOLECULAR SEQUENCE DATA; PLANT PROTEINS; RNA, PLANT; SACCHAROMYCES CEREVISIAE; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SESQUITERPENES;

EID: 68349157140     PISSN: None     EISSN: 14712229     Source Type: Journal    
DOI: 10.1186/1471-2229-9-86     Document Type: Article

References (71)

1. Enzymatic formation of sesquiterpenes. DE Cane, Chemical Reviews 1990 90 7 1089 1103
2. Sesquiterpene biosynthesis: cyclization mechanisms. DE Cane, Comprehensive Natural Products Chemistry Amsterdam: Elsevier, Cane DE, 1999 2 155 200
3. Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes. EM Davis R Croteau, Topics in Current Chemistry Berlin Heidelberg: Springer-Verlag 2000 209 54 95
4. Solid phase microextraction for quantitative headspace sampling of apple volatiles. AJ Matich DD Rowan NH Banks, Analytical Chemistry 1996 68 23 4114 4118 8946792
5. α-farnesene in the natural coating of apples. FE Huelin KE Murray, Nature 1966 210 42 1260 1261 5967802
6. Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. F Chen D Tholl JC D'Auria A Farooq E Pichersky J Gershenzon, Plant Cell 2003 15 2 481 494 12566586
7. Attracting friends to feast on foes: Engineering terpene emission to make crop plants more attractive to herbivore enemies. J Degenhardt J Gershenzon IT Baldwin A Kessler, Current Opinion in Biotechnology 2003 14 2 169 176 12732318
8. Airborne signals prime plants against insect herbivore attack. J Engelberth HT Alborn EA Schmelz JH Tumlinson, Proceedings of the National Academy of Sciences of the United States of America 2004 101 6 1781 1785 14749516
9. Plant science: Genetic engineering of terpenoid metabolism attracts bodyguards to Arabidopsis. IF Kappers A Aharoni TWJM Van Herpen LLP Luckerhoff M Dicke HJ Bouwmeester, Science 2005 309 5743 2070 2072 16179482
10. Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens. CI Keeling J Bohlmann, New Phytologist 2006 170 4 657 675 16684230
11. Defensive function of herbivore-induced plant volatile emissions in nature. A Kessler IT Baldwin, Science 2001 291 5511 2141 2144 11251117
12. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. M Wink, Phytochemistry 2003 64 1 3 19 12946402
13. Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. A Aharoni AP Giri F Griepink W-J De Kogel FWA Verstappen HA Verhoeven MA Jongsma HJ Bouwmeester S Deuerlein W Schwab, Plant Cell 2003 15 12 2866 2884 14630967
14. Identification of Vitis vinifera (-) - terpineol synthase by silico screening of full-lenght cDNA ESTs and functional characterization of recombinant terpene synthase. DM Martin J Bohlmann, Phytochemistry 2004 65 1223 1229 15184006
15. Biosynthesis of plant volatiles: Nature's diversity and ingenuity. E Pichersky JP Noel N Dudareva, Science 2006 311 5762 808 811 16469917
16. 1-Deoxy-D-xylulose 5-phosphate reductoisomerase and plastid isoprenoid biosynthesis during tomato fruit ripening. M Rodríguez-Concepcin I Ahumada E Diez-Juez S Sauret-Geto L María Lois F Gallego L Carretero-Paulet N Campos A Boronat, Plant Journal 2001 27 3 213 222 11532167
17. Biological activities of sesquiterpene lactones. AK Picman, Biochemical Systematics and Ecology 1986 14 255 281
18. Sesquiterpene Latones as Taxonomic Characters in the Asteraceae. FC Seaman, The Botanical Review 1982 48 121 592
19. Metabolite profiling of sesquiterpene lactones from Lactuca species: Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives. RA Sessa MH Bennett MJ Lewis JW Mansfield MH Beale, Journal of Biological Chemistry 2000 275 35 26877 26884 10858433
20. Chemotaxonomy Based on Metabolites from Glandular Trichomes. O Spring, Plant Trichomes San Diego: Academic Press, Hallahan DL, Gray JC, 31 2000 31 153 169
21. Feverfew: Chemistry and biological activity. DW Knight, Natural Product Reports 1995 12 3 271 276 7792073
22. Synthesis of mono- and sesquiterpenoids; XXIV: (-)-Homogynolide A, an insect antifeedant isolated from Homogyne alpina. K Mori Y Matsushima, Synthesis 1995 7 845 850
23. Feeding and toxic effects of floral sesquiterpene lactones, diterpenes, and phenolics from sunflower (Helianthus annuus L.) on western corn rootworm. CA Mullin AA Alfatafta JL Harman SL Everett AA Serino, Journal of Agricultural and Food Chemistry 1991 39 12 2293 2299
24. Distribution and antifeedant associations of sesquiterpene lactones in cultivated sunflower (Helianthus annuus L.) on western corn rootworm (Diabrotica virgifera virgifera LeConte). JC Chou CA Mullin, Journal of Chemical Ecology 1993 19 7 1439 1452
25. Annuithrin, a new biologically active germacranolide from Helianthus annuus. O Spring K Albert W Gradmann, Phytochemistry 1981 20 8 1883 1885
26. Qinghaosu (artemisinin): an antimalarial drug from China. DL Klayman, Science 1985 228 1049 1055 3887571
27. The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. N Dudareva S Andersson I Orlova N Gatto M Reichelt D Rhodes W Boland J Gershenzon, Proceedings of the National Academy of Sciences of the United States of America 2005 102 3 933 938 15630092
28. Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana. O Laule A Fürholz HS Chang T Zhu X Wang PB Heifetz W Gruissem BM Lange, Proceedings of the National Academy of Sciences of the United States of America 2003 100 11 6866 6871 12748386
29. (+)-Germacrene A biosynthesis The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory. JW De Kraker MCR Franssen A De Groot WA König HJ Bouwmeester, Plant Physiology 1998 117 4 1381 1392 9701594
30. cDNA isolation and characterization of (+)-germacrene A synthase from Ixeris dentata form. albiflora Hara. MY Kim YJ Chang MH Bang NI Baek J Jin CH Lee SU Kim, Journal of Plant Biology 2005 48 2 178 186
31. Isolation and characterization of two germacrene A synthase cDNA clones from chicory. HJ Bouwmeester J Kodde FWA Verstappen IG Altug JW De Kraker TE Wallaart, Plant Physiology 2002 129 1 134 144 12011345
32. Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.). MH Bennett JW Mansfield MJ Lewis MH Beale, Phytochemistry 2002 60 3 255 261 12031443
33. Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. CM Bertea A Voster FWA Verstappen M Maffei J Beekwilder HJ Bouwmeester, Archives of Biochemistry and Biophysics 2006 448 1-2 3 12
34. Sesquiterpenes from noncapitate glandular trichomes of Helianthus annuus. O Spring U Rodon FA Macias, Phytochemistry 1992 31 5 1541 1544
35. Microsampling, an alternativ approach to use sesquiterpene lactones for systematics. Part I in the series "The sesquiterpene lactone chemistry of Helianthus (Asteraceae)". O Spring, Biochemical Systematics and Ecology 1989 17 509 517
36. 5-Deoxynevadensin, a novel flavone in sunflower and aspects of biosynthesis during trichome development. J Göpfert J Conrad O Spring, Natural Products Communications 2006 1 11 335 340
37. Trichome microsampling of sesquiterpene lactones for the use of systematic studies. O Spring, Recent Advances in Phytochemistry 1991 25 319 345
38. Cytological development and sesquiterpene lactone secretion in capitate glandular trichomes of sunflower. JC Göpfert N Heil O Spring J Conrad, Plant Biology 2005 7 2 148 155 15822010
39. Enantiospecific (+)- and (-)-germacrene D synthases, cloned from goldenrod, reveal a functionally active variant of the universal isoprenoid-biosynthesis aspartate-rich motif. I Prosser IG Altug AL Phillips WA König HJ Bouwmeester MH Beale, Archives of Biochemistry and Biophysics 2004 432 2 136 144
40. A cDNA clone for -caryophyllene synthase from Artemisia annua. Y Cai JW Jia J Crock ZX Lin XY Chen R Croteau, Phytochemistry 2002 61 5 523 529 12409018
41. Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L. P Mercke M Bengtsson HJ Bouwmeester MA Posthumus PE Brodelius, Archives of Biochemistry and Biophysics 2000 381 2 173 180
42. Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L. P Mercke J Crock R Croteau PE Brodelius, Archives of Biochemistry and Biophysics 1999 369 2 213 222
43. Amorpha-4,11-diene synthase: Cloning and functional expression of a key enzyme in the biosynthetic pathway of the novel antimalarial drug artemisinin. TE Wallaart HJ Bouwmeester J Hille L Poppinga NCA Maijers, Planta 2001 212 3 460 465 11289612
44. Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases. K Back J Chappell, The Journal of Biological Chemistry 1995 13 7375 7381
45. Plant terpenoid synthases: Molecular biology and phylogenetic analysis. J Bohlmann R Croteau G Meyer-Gauen, Proceedings of the National Academy of Sciences of the United States of America 1998 95 8 4126 4133 9539701
46. Genomic organization of plant terpene synthases and molecular evolutionary implications. SC Trapp RB Croteau, Genetics 2001 158 2 811 832 11404343
47. Genomic analysis of the terpenoid synthase (AtTPS) gene family of Arabidopsis thaliana. S Aubourg A Lecharny J Bohlmann, Mol Genet Genomics 2002 267 6 730 745 12207221
48. Cloning, expression, and characterization of (+) - cadinene synthase: A catalyst for cotton phytoalexin biosynthesis. XY Chen Y Chen P Heinstein VJ Davisson, Archives of Biochemistry and Biophysics 1995 324 2 255 266
49. Cloning and heterologous expression of a second (+) - cadinene synthase from Gossypium arboreum. XY Chen M Wang Y Chen VJ Davisson P Heinstein, Journal of Natural Products 1996 59 10 944 951 8904844
50. Antisense suppression of a (+) - cadinene synthase gene in cotton prevents the induction of this defence response gene during bacterial blight infection but not its constitutive expression. BJ Townsend A Poole CJ Blake DJ Llewellyn, Plant Physiology 2005 138 1 516 528 15849309
51. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. DK Ro EM Paradise M Quellet KJ Fisher KL Newman JM Ndungu KA Ho RA Eachus TS Ham J Kirby, Nature 2006 440 7086 940 943 16612385
52. Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce the anti-malarial drug precursor, artemisinic acid. DK Ro M Quellet EM Paradise H Burd D Eng C Paddon JD Newman JD Keasling, BMC Biotechnology 2008 8 83 18983675
53. Sesquiterpene synthases from grand fir (Abies grandis): Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of -selinene synthase and -humulene synthase. CL Steele J Crock J Bohlmann R Croteau, Journal of Biological Chemistry 1998 273 4 2078 2089 9442047
54. Purification of (+) - cadinene synthase, a sesquiterpene cyclase from bacteria-inoculated cotton foliar tissue. EM Davis J Tsuji GD Davis ML Pierce M Essenberg, Phytochemistry 1996 41 4 1047 1055 8728715
55. Coordinated accumulation of (+) - cadinene synthase mRNAs and gossypol in developing seeds of Gossypium hirsutum and a new member of the cad1 family from G. arboreum. YL Meng JW Jia CJ Liu WQ Liang P Heinstein XY Chen, Journal of Natural Products 1999 62 2 248 252 10075752
56. Emissions of volatile organic compounds from sunflower and beech: Dependence on temperature and light intensity. G Schuh AC Heiden T Hoffmann J Kahl P Rockel J Rudolph J Wildt, Journal of Atmospheric Chemistry 1997 27 3 291 318
57. The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions. TG Köllner C Schnee J Gershenzon J Degenhardt, Phytochemistry 2004 65 13 1895 1902 15279995
58. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. F Chen DK Ro J Petri J Gershenzon J Bohlmann E Pichersky D Tholl, Plant Physiology 2004 135 4 1956 1966 15299125
59. Biochemical and genomic characterization of terpene synthases in Magnolia grandiflora. S Lee J Chappell, Plant Physiology 2008 147 3 1017 1033 18467455
60. Monoterpene biosynthesis in lemon (Citrus limon). J Lücker MK El Tamer W Schwab FWA Verstappen LHW van der Plas HJ Bouwmeester HA Verhoeven, European Journal of Biochemistry 2002 269 3160 3171 12084056
61. Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. J Bohlmann EJ Stauber B Krock NJ Oldham J Gershenzon IT Baldwin, Phytochemistry 2002 60 2 109 116 12009313
62. Isoprenoid metabolism and plastid reorganization in arbuscular mycorrhizal roots. D Strack T Fester, New Phytologist 2006 172 1 22 34 16945086
63. Microarray expression profiling and functional characterization of AtTPS genes: Duplicated Arabidopsis thaliana sesquiterpene synthase genes At4g13280 and At4g13300 encode root-specific and wound-inducible (Z) - bisabolene synthases. DK Ro J Ehlting CI Keeling R Lin N Mattheus J Bohlmann, Archives of Biochemistry and Biophysics 2006 448 1-2 104 116
64. Factors affection infection of sunflowers by Plasmopara halstedii. Y Cohen W Sackston, Canadian Journal of Botany 1973 51 15 22
65. Molecular Cloning - A Laboratory Manual. J Sambrook DW Russell, New York: Cold Spring Harbor Laboratoty Press 3 2001 1
66. Oligodeoxyribonucleotide ligation to single-stranded cDNAs: A new tool for cloning 5' ends of mRNAs and for constructing cDNA libraries by in vitro amplification. JBDM Edwards J Delort J Mallet, Nucleic Acids Research 1991 19 19 5227 5232 1923806
67. Ligation-anchored PCR: A simple amplification technique with single-sided specificity. AB Troutt MG McHeyzer-Williams B Pulendran GJV Nossal, Proceedings of the National Academy of Sciences of the United States of America 1992 89 20 9823 9825 1409706
68. The primary structure of sunflower (Helianthus annuus) ubiquitin. M-N Binet A Steinmetz L-H Tessier, Nucleic Acids Research 1989 17 5 2119 2538802
69. A new mathematical model for relative quantification in real-time RT-PCR. MW Pfaffl, Nucleic acids research 2001 29 9 11328886
70. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of rotein-dye bindung. MM Bradford, Analytical Biochemistry 1976 72 248 254 942051
71. Transformation of yeast by lithium acetate/single-stranded carrier DNA/polyethylene glycol method. RD Gietz RA Woods, Methods in Enzymology 2002 350 87 96 12073338