A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate

Phytochemistry

Volumn 91, Issue , 2013, Pages 93-99

  Günnewich, Nils ^a,b,c   Higashi, Yasuhiro ^a   Feng, Xiaohong ^a   Choi, Kum Boo ^b   Schmidt, Jürgen ^b   Kutchan, Toni M ^a,b  

^a DONALD DANFORTH PLANT SCIENCE CENTER   (United States)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^c SAARLAND UNIVERSITY   (Germany)

Author keywords

Clary sage; Hydroxy copalyl diphosphate; Lamiaceae; Salvia sclarea; Sclareol; Terpene synthase

Indexed keywords

(8R) HYDROXY COPALYL DIPHOSPHATE; (8R)-HYDROXY-COPALYL DIPHOSPHATE; GERANYLGERANYL PYROPHOSPHATE; ISOPRENOID PHOSPHATE; ORGANOPHOSPHATE; TERPENE SYNTHASE; TRANSFERASE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; ENZYMOLOGY; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PLANT SEED; SALVIA;

ALKYL AND ARYL TRANSFERASES; BIOCATALYSIS; CYCLIZATION; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; ORGANOPHOSPHATES; POLYISOPRENYL PHOSPHATES; SALVIA; SEEDS;

ESCHERICHIA COLI; LAMIACEAE; SALVIA; SALVIA SCLAREA;

EID: 84878934045     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.07.019     Document Type: Article

References (31)

1. K. Back, and J. Chappell Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases J. Biol. Chem. 270 1995 7375 7381
2. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem. 72 1976 248 254
3. E. Cho, A. Okada, H. Kenmoku, K. Otomo, T. Toyomasu, W. Mitsuhashi, T. Sassa, A. Yajima, G. Yabuta, K. Mori, H. Oikawa, H. Toshima, N. Shibuya, H. Nojiri, T. Omori, M. Nishiyama, and H. Yamane Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor Plant J. 37 2004 1 8 (Pubitemid 38078261)
4. P. Chomczynski, and N. Sacchi Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction Anal. Biochem. 162 1987 156 159 (Pubitemid 17064313)
5. W. Eisenreich, M. Schwarz, A. Cartayrade, D. Arigoni, M.H. Zenk, and A. Bacher The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms Chem. Biol. 5 1998 221 233
6. V. Falara, E. Pichersky, and A.K. Kanellis 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 Plant Physiol. 154 2010 301 310
7. J. Gershenzon, D. McCaskill, J.I. Rajaonarivony, C. Mihakiak, F. Karp, and R. Croteau Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products Anal. Biochem. 200 1992 130 138
8. Z. Guo, R.F. Severson, and G.J. Wagner Biosynthesis of the diterpene cis-abienol in cell-free extracts of tobacco trichomes Arch. Biochem. Biophys. 308 1994 103 108 (Pubitemid 24172610)
9. Z. Guo, and G.J. Wagner Biosynthesis of labdenediol and sclareol in cell-free extracts from trichomes of Nicotiana glutinosa Planta 197 1995 627 632 (Pubitemid 3008137)
10. K.-i. Hayashi, H. Kawaide, M. Notomi, Y. Sakigi, A. Matsuo, and H. Nozaki Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens FEBS Lett. 580 2006 6175 6181 (Pubitemid 44666801)
11. O. Jaillon, J.M. Aury, B. Noel, A. Policriti, C. Clepet, A. Casagrande, N. Choisne, S. Aubourg, N. Vitulo, C. Jubin, A. Vezzi, F. Legeai, P. Hugueney, C. Dasilva, D. Horner, E. Mica, D. Jublot, J. Poulain, C. Bruyere, and A. Billault The grapevine genome sequence suggests ancestral hexaploidization in major angiosperm phyla Nature 449 2007 463 467 (Pubitemid 47509545)
12. K. Keegstra, L.J. Olsen, and S.M. Theg Chloroplastic precursors and their transport across the envelope membranes Annu. Rev. Plant Physiol. Plant Mol. Biol. 40 1989 471 501
13. C.I. Keeling, L.L. Madilao, P. Zerbe, H.K. Dullat, and J. Bohlmann The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol J. Biol. Chem. 286 2011 21145 21153
14. H.J. Nicholas Biosynthesis of 14C-sclareol and β-sitosterol from 2-14C-mevalonic acid Nature 189 1961 143 144
15. 14 J. Biol. Chem. 237 1961 1481 1484
16. 14C]sclareol Biochim. Biophys. Acta 84 1964 80 90
17. G. Ohloff Riechstoffe und Geruchssinn: Die molekulare Welt der Düfte 1990 Springer Verlag Berlin, Heidelberg, New York pp. 208-214
18. R.J. Peters, M.M. Ravn, R.M. Coates, and R.B. Croteau Bifunctional abietadiene synthase: free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites J. Am. Chem. Soc. 123 2001 8974 8978 (Pubitemid 32884718)
19. R.J. Peters Two rings in them all: the labdane-related diterpenoids Nat. Prod. Rep. 27 2010 1521 1530
20. M. Pietsch, and W.A. König Enantiomers of sesquiterpene and diterpene hydrocarbons in Araucaria species Phytochem. Anal. 11 2000 99 105 (Pubitemid 30153718)
21. S. Prisic, J. Xu, R.M. Coates, and R.J. Peters Probing the role of the DXDD motif in class II diterpene cyclases ChemBioChem 8 2007 869 874 (Pubitemid 47194834)
22. C. Schmiderer, P. Grassi, J. Novak, M. Weber, and C. Franz Diversity of essential oil glands of clary sage (Salvia sclarea, L., Lamiaceae) Plant Biol. 10 2008 433 440 (Pubitemid 351832383)
23. C.M. Starks, K. Back, J. Chappell, and J.P. Noel Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase Science 277 1997 1815 1820 (Pubitemid 27449192)
24. T.P. Sun, and Y. Kamiya The arabidopsis GA1 locus encodes the cyclase ent-kaurene synthetase A of gibberellin biosynthesis Plant Cell 6 1994 1509 1518 (Pubitemid 24976505)
25. G.A. Tuskan, S. Difazio, S. Jansson, J. Bohlmann, I. Grigoriev, U. Hellsten, N. Putnam, S. Ralph, S. Rombauts, A. Salamov, J. Schein, L. Sterck, A. Aerts, R.R. Bhalerao, R.P. Bhalerao, D. Blaudez, W. Boerjan, A. Brun, A. Brunner, and V. Busov The Genome of Black Cottonwood, Populus trichocarpa (Torr. & Gray) Science 313 2006 1596 1604 (Pubitemid 44414027)
26. B.S. Vogel, M.R. Wildung, G. Vogel, and R. Croteau Abietadiene synthase from grand fir (Abies grandis). cDNA Isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis J. Biol. Chem. 38 1996 23262 23268 (Pubitemid 26314767)
27. Y. Volmar, and A. Jermstad Le sclaréol, principal constituent de l'essence absolue de Sauge Sclarée A. C. R. Acad. Sci. Paris 186 1928 783 785
28. M. Xu, M.L. Hillwig, S. Prisic, R.M. Coates, and R.J. Peters Functional identification of rice syn-copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products Plant J. 39 2004 309 318 (Pubitemid 39040137)
29. S. Yamaguchi, T. Saito, H. Abe, H. Yamane, N. Murofushi, and Y. Kamiya Molecular cloning and characterization of a cDNA encoding the gibberellin biosynthetic enzyme ent-kaurene synthase B from pumpkin (Cucurbita maxima L.) Plant J. 10 1996 203 213 (Pubitemid 27111473)
30. S. Yamaguchi Gibberellin metabolism and its regulation Annu. Rev. Plant Biol. 59 2008 225 251 (Pubitemid 351813030)
31. D. Zhang, and C.D. Poulter Analysis and purification of phosphorylated isoprenoids by reversed-phase HPLC Anal. Biochem. 213 1993 356 361 (Pubitemid 23271263)