Genetic mapping and characterization of the globe artichoke (+)-germacrene A synthase gene, encoding the first dedicated enzyme for biosynthesis of the bitter sesquiterpene lactone cynaropicrin

Plant Science

Volumn 190, Issue , 2012, Pages 1-8

  Menin, Barbara ^a   Comino, Cinzia ^a   Portis, Ezio ^a   Moglia, Andrea ^a   Cankar, Katarina ^b   Bouwmeester, Harro J ^b   Lanteri, Sergio ^a   Beekwilder, Jules ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

(+) Germacrene a; Cynara cardunculus; Cynaropicrin; Sesquiterpene lactones; Terpene synthase

Indexed keywords

COMPLEMENTARY DNA; CYNAROPICRIN; LACTONE; PHENOL DERIVATIVE; SESQUITERPENE; TRANSFERASE; VEGETABLE PROTEIN;

ANTIBODY SPECIFICITY; ARTICHOKE; ARTICLE; BIOSYNTHESIS; CHEMISTRY; CHROMOSOME MAP; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION; GENETIC LINKAGE; GENETICS; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PHYLOGENY; PLANT GENE; SINGLE NUCLEOTIDE POLYMORPHISM; TASTE;

ALKYL AND ARYL TRANSFERASES; BIOSYNTHETIC PATHWAYS; CHROMATOGRAPHY, LIQUID; CHROMOSOME MAPPING; CYNARA SCOLYMUS; DNA, COMPLEMENTARY; ESCHERICHIA COLI; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION, PLANT; GENES, PLANT; GENETIC LINKAGE; LACTONES; MOLECULAR SEQUENCE DATA; ORGAN SPECIFICITY; PHENOLS; PHYLOGENY; PLANT PROTEINS; POLYMORPHISM, SINGLE NUCLEOTIDE; SESQUITERPENES; TASTE;

ASTERACEAE; CYNARA CARDUNCULUS; CYNARA SCOLYMUS; ESCHERICHIA COLI; SCOLYMUS;

EID: 84859648923     PISSN: 01689452     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plantsci.2012.03.006     Document Type: Article

References (43)

1. Lanteri S., Portis E. Globe artichoke and cardoon. Vegetables I: Asteraceae, Brassicaceae, Chenopodicaceae, and Cucurbitaceae 2008, 49-74. Springer. J. Prohens, F. Nuez (Eds.).
2. Comino C., Lanteri S., Portis E., Acquadro A., Romani A., Hehn A., Larbat R., Bourgaud F. Isolation and functional characterization of a cDNA coding a hydroxycinnamoyltransferase involved in phenylpropanoid biosynthesis in Cynara cardunculus L. BMC Plant Biology 2007, 7:14.
3. Moglia A., Lanteri S., Comino C., Acquadro A., de Vos R., Beekwilder J. Stress-induced biosynthesis of dicaffeoylquinic acids in globe artichoke. Journal of Agricultural and Food Chemistry 2008, 56:8641-8649.
4. Comino C., Hehn A., Moglia A., Menin B., Bourgaud F., Lanteri S., Portis E. The isolation and mapping of a novel hydroxycinnamoyltransferase in the globe artichoke chlorogenic acid pathway. BMC Plant Biology 2009, 9:30.
5. Moglia A., Comino C., Portis E., Acquadro A., De Vos R., Beekwilder J., Lanteri S. Isolation and mapping of a C3'H gene (CYP98A49) from globe artichoke, and its expression upon UV-C stress. Plant Cell Reports 2009, 28:963-974.
6. Menin B., Comino C., Moglia A., Dolzhenko Y., Portis E., Lanteri S. Identification and mapping of genes related to caffeoylquinic acid synthesis in Cynara cardunculus L. Plant Science 2010, 179:338-347.
7. Schneider G., Thiele K. Die Verteilung des Bitter-stoffes Cynaropicrin in der Artischocke. Planta Medica 1974, 26:174-183.
8. Fritsche J., Beindorff C., Dachtler M., Zhang H., Lammers J. Isolation, characterization and determination of minor artichoke (Cynara scolymus L.) leaf extract compounds. European Food Research and Technology 2002, 215:149-157.
9. Cravotto G., Nano G., Binello A., Spagliardi P., Seu G. Chemical and biological modification of cynaropicrin and grosheimin: a structure-bitterness relationship study. Journal of the Science of Food and Agriculture 2005, 85:1757-1764.
10. Shimoda H., Ninomiya K., Nishida N., Yoshino T., Morikawa T., Matsuda H., Yoshikawa M. Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action. Bioorganic & Medicinal Chemistry Letters 2003, 13:223-228.
11. Cho J., Kim A., Jung J., Chun T., Rhee M., Yoo E. Cytotoxic and pro-apoptotic activities of cynaropicrin, a sesquiterpene lactone, on the viability of leukocyte cancer cell lines. European Journal of Pharmacology 2004, 492:85-94.
12. Schinor E., Salvador M., Ito I., de Albuquerque S., Dias D. Trypanocidal and antimicrobial activities of Moquinia kingii. Phytomedicine 2004, 11:224-229.
13. Emendörfer F., Emendörfer F., Bellato F., Noldin V., Cechinel-Filho V., Yunes R., Delle Monache F., Cardozo A. Antispasmodic activity of fractions and cynaropocrin from Cynara scolymus on guinea-pig ileum. Biological & Pharmaceutical Bulletin 2005, 28:902-904.
14. Ishida K., Kojima R., Tsuboi M., Tsuda Y., Ito M. Effects of artichoke leaf extract on acute gastric mucosal injury in rats. Biological & Pharmaceutical Bulletin 2010, 33:223-229.
15. Yasukawa K., Matsubara H., Sano Y. Inhibitory effect of the flowers of artichoke (Cynara cardunculus) on TPA-induced inflammation and tumor promotion in two-stage carcinogenesis in mouse skin. Journal of Natural Medicines 2010, 64:388-391.
16. Seaman F.C. Sesquiterpene lactones as taxonomic characteristics in the Asteraceae. The Botanical Review 1982, 48:123-595.
17. De Kraker J., Franssen M., Joerink M., de Groot A., Bouwmeester H. Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome P450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory. Plant Physiology 2002, 129:257-268.
18. Ikezawa N., Gopfert J., Nguyen D., Kim S., O'Maille P., Spring O., Ro D. Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism. Journal of Biological Chemistry 2011, 286:21601-21611.
19. Liu Q., Majdi M., Cankar K., Goedbloed M., Charnikhova T., Verstappen F.W.A., de Vos R.C.H., Beekwilder J., van der Krol S., Bouwmeester H. Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana. PLoS One 2011, 6:e23255.
20. Bouwmeester H., Kodde J., Verstappen F., Altug I., de Kraker J., Wallaart T. Isolation and characterization of two germacrene A synthase cDNA clones from chicory. Plant Physiology 2002, 129:134-144.
21. Bennett M., Mansfield J., Lewis M., Beale M. Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.). Phytochemistry 2002, 59:255-261.
22. Prosser I., Phillips A., Gittings S., Lewis M., Hooper A., Pickett J., Beale M. (+)-(10R)-germacrene A synthase from goldenrod, Solidago canadensis: cDNA isolation, bacterial expression and functional analysis. Phytochemistry 2002, 59:691-702.
23. Kim M., Chang Y., Bang M., Baek N., Jin J., Lee C., Kim S. cDNA isolation and characterization of (+)-germacrene A synthase from Ixeris dentata form. albiflora Hara. Journal of Plant Biology 2005, 48:178-186.
24. Bertea C., Voster A., Verstappen F., Maffei M., Beekwilder J., Bouwmeester H. Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Archives of Biochemistry and Biophysics 2006, 448:3-12.
25. Gopfert J., MacNevin G., Ro D., Spring O. Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes. BMC Plant Biology 2009, 9:86.
26. Thorup T., Tanyolac B., Livingstone K., Popovsky S., Paran I., Jahn M. Candidate gene analysis of organ pigmentation loci in the Solanaceae. Proceedings of the National Academy of Sciences of the United States of America 2000, 97:11192-11197.
27. Chen X., Salamini F., Gebhardt C. A potato molecular-function map for carbohydrate metabolism and transport. Theoretical and Applied Genetics 2001, 102:284-295.
28. Cadalen T., Morchen M., Blassiau C., Clabaut A., Scheer I., Hilbert J., Hendriks T., Quillet M. Development of SSR markers and construction of a consensus genetic map for chicory (Cichorium intybus L.). Molecular Breeding 2010, 25:699-722.
29. Portis E., Mauromicale G., Mauro R., Acquadro A., Scaglione D., Lanteri S. Construction of a reference molecular linkage map of globe artichoke (Cynara cardunculus var. scolymus). Theoretical and Applied Genetics 2009, 120:59-70.
30. Portis E., Acquadro A., Scaglione D., Mauromicale G., Mauro R., Taylor C.A., Knapp S.J., Lanteri S. Construction of an SSR-based linkage map for Cynara cardunculus. 8th Plant Genomics European Meeting 2009.
31. Menin B., Lanteri S., Comino C., Moglia A., Barba M., Van Herpen T.W.J.M., Beekwilder J. Setting up a callogenesis and transformation system for globe artichoke. Journal of Biotechnology 2010, 150S:497. (abstracts).
32. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning: A Laboratory Manual 1989, Laboratory Press, Cold Spring Harbor, NY, USA. second ed.
33. Scaglione D., Acquadro A., Portis E., Taylor C.A., Lanteri S., Knapp S.J. Ontology and diversity of transcript-associated microsatellites mined from a globe artichoke EST database. BMC Genomics 2009, 10:454.
34. Degenhardt J., Kollner T., Gershenzon J. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 2009, 70:1621-1637.
35. Kumar S., Tamura K., Nei M. MEGA3: integrated software for molecular evolutionary genetics analysis and sequence alignment. Briefings in Bioinformatics 2004, 5:150-163.
36. ® v.4, Software for the Calculation of Genetic Linkage Maps in Experimental Populations 2006, B.V. Kyazma, Wageningen, Netherlands.
37. Kosambi D. The estimation of map distances from recombination values. Annals of Eugenics 1944, 12:172-175.
38. Hay A., Hamburger M., Hostettmann K., Hoult J. Toxic inhibition of smooth-muscle contractility by plant-derived sesquiterpenes caused by their chemically reactive alpha-methylenebutyrolactone functions. British Journal of Pharmacology 1994, 112:9-12.
39. Van Beek T.A., Maas P., King B.M., Leclercq E., Voragen A.G.J., De Groot A.E. Bitter sesquiterpene lactones from chicory roots. Journal of Agricultural and Food Chemistry 1990, 38:1035-1038.
40. Dittrich M. Cynarae-systemic review. The Biology and Chemistry of the Compositae 1977, 999-1015. V.H. Heywood, J.B. Harborne, B.L. Turner (Eds.).
41. Moth Wiklund A. Arcyna, a new genus segregated from Cynara (Compositae). Willdenowia 2003, 33:63-68.
42. Nguyen D., Gopfert J., Ikezawa N., MacNevin G., Kathiresan M., Conrad J., Spring O., Ro D. Biochemical conservation and evolution of germacrene A oxidase in Asteraceae. Journal of Biological Chemistry 2010, 285:16588-16598.
43. Graham1 I.A., Besser K., Blumer S., Branigan C.A., Czechowski T., Elias L., Guterman I., Harvey D., Isaac P.G., Khan A.M., Larson T.R., Li Y., Pawson T., Penfield T., Rae A.M., Rathbone D.A., Reid S., Ross J., Smallwood M.F., Segura V., Townsend T., Vyas D., Winzer T., Bowles D. The genetic map of Artemisia annua L. identifies loci affecting yield of the antimalarial drug artemisinin. Science 2010, 327:328-331.