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(12) United States Patent (10) Patent No.: US 9,115,366 B2 Tissier Et Al

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(12) United States Patent (10) Patent No.: US 9,115,366 B2 Tissier Et Al USOO9115366B2 (12) United States Patent (10) Patent No.: US 9,115,366 B2 Tissier et al. (45) Date of Patent: *Aug. 25, 2015 (54) SYSTEM FOR PRODUCING TERPENOIDS IN WO WO99,38957 * 8, 1999 .......... C12N 15/82 PLANTS WO WO99,38957 A1 8/1999 WO WOOOf 17327 A3 3.2000 Fre WO WO 01/20008 A2 3, 2001 (75) Inventors: Alain Tissier, Pertuis (FR); Christophe WO WO 2004/111183 A2 12/2004 Sallaud, Montpellier (FR); Denis WO WO 2006/04.0479 4/2006 Rontein,ontein, GreouxG les Bains (FR(FR) OTHER PUBLICATIONS (73) Assignee: PHILIP MORRIS PRODUCTS S.A., Aharoni, Aetal. The Plant Cell (Dec. 2003), vol. 15: pp. 2866-2884.* Neuchatel (CH) Besumbes, O. et al. Biotechnology and Bioengineering; Oct. 20. 2004; vol. 88, No. 2: pp. 168-175.* (*) Notice: Subject to any disclaimer, the term of this Wang, E. et al. Nature Biotechnology, Apr. 2001; vol. 19, pp. 371 patent is extended or adjusted under 35 37.4% U.S.C. 154(b) by 900 days. Wang, E. et al. Journal of Experimental Botany, Sep. 2002, vol. 53, No. 376; pp. 1891-1897.* This patent is Subject to a terminal dis Walker K. et al. Phytochemistry (2001) vol. 58; pp. 1-7.* claimer. Gutiérrez-Alcalá et al., A versatile promoter for the expression of proteins in glandular and non-glandular trichomes from a variety of plants, 56 J of Exp Botany No. 419, 2487-2494 (2005).* (21) Appl. No.: 11/814,943 Besumbes et al. (Metabolic Engineering of Isoprenoid Biosynthesis in Arabidopsis for the Production of Taxadiene, the First Committed (22) PCT Filed: Jan. 27, 2006 Precursor of Taxol. 88 Biotechnology and Bioengineering No. 2, 165-175 (2004)).* (86). PCT No.: PCT/FR2006/OOO188 Wang et al. (Isolation and characterization of the CYP71D16 trichome-specific promoter from Nicotiana tabacum L., 53J of Exp S371 (c)(1), Botany No. 37, 1891-1897 at 1895-1897 (2002) (hereinafter Wang et (2), (4) Date: Jul. 27, 2007 al.2002)).* Wang et al. (Suppression of a P450 hydroxylase gene in plant (87) PCT Pub. No.: WO2006/079727 trichome glands enhances natural-product-based aphid resistance, 19 Nature Biotechnology, 371-374 (2001) (hereinafter Wang et PCT Pub. Date: Aug. 3, 2006 al.2001).* Walker et al. (Taxol biosynthetic genes, 58 Phytochemistry, 1-7 (65) Prior Publication Data (2001)).* Stegemann et al. (Experimental Reconstruction of Functional gene US 2008/O281135A1 Nov. 13, 2008 Transfer from the Tobacco Plastid Genome to the Nucleus, 18 Plant Cell, 2869-2878 (2006)).* (30) Foreign Application Priority Data Lange, B. M. etal. "Genetic engineering of essential oil production in mint' Current Opinion in Plant Biology, 1999, pp. 139-144, vol. 2, Jan. 27, 2005 (FR) ...................................... O5 OO855 XP-00910.1099. Wang, E. et al. “Isolation and characterization of the CYP7 ID 16 (51) Int. Cl. trichome-specific promoter from Nicotiana tabacum L. Journal of CI2N IS/II3 (2010.01) Experimental Botany, Sep. 2002, pp. 1891-1897, vol. 53, No. 376, CI2N 5/14 (2006.01) XP-002318244. AOIH I/O (2006.01) (Continued) CI2N 15/82 (2006.01) CI2N 9/88 (2006.01) Primary Examiner — Russell Kallis CI2P 5/00 (2006.01) Assistant Examiner — Rebecca Stephens CI2P 15/00 (2006.01) (74) Attorney, Agent, or Firm — Saliwanchik, Lloyd & (52) U.S. Cl. Eisenschenk CPC .............. CI2N 15/8243 (2013.01); C12N 9/88 (2013.01); C12N 15/8223 (2013.01); C12P (57) ABSTRACT 5/007 (2013.01); CI2P 15/00 (2013.01); C12N The invention concerns a method for producing terpenes of 15/I 137 (2013.01); C12N 15/8205 (2013.01) interestin plants having glandular trichomes, as well as plants (58) Field of Classification Search useful for producing said terpenes of interest. Said plants USPC .......................................................... 800/278 comprise a sequence encoding a heterologous terpene Syn See application file for complete search history. thase under the control of a promoter enabling it to be spe cifically expressed in the trichomes. Moreover, the pathway (56) References Cited for producing endogenous diterpenes is preferably blocked in U.S. PATENT DOCUMENTS the trichomes of the plants, to increase the flow in the heter ologous pathway. The secretion of heterologous terpenes is 6,730,826 B2 5/2004 Wagner et al. spontaneous resulting in easy collection. The present inven 2004/0234968 A1 11/2004 Croteau et al. tion also concerns plants exhibiting a blocked production of a 2006/0150283 A1* 7/2006 Alexandrov et al. ......... 800,288 compound having antibiotic properties at the Surface of 2009/03OO791 A1 12/2009 Tissier et al. leaves exhibiting enhanced efficiency of transformation by a FOREIGN PATENT DOCUMENTS bacterium. WO WO 93.07.266 A1 4f1993 19 Claims, 10 Drawing Sheets WO WO99, 1946O A1 4f1999 (1 of 10 Drawing Sheet(s) Filed in Color) US 9,115,366 B2 Page 2 (56) References Cited the Peltate Glands of Three Cultivars of Basil” Plant Physiology, Nov. 2004, pp. 3724-3736, vol. 136. OTHER PUBLICATIONS Liu, H.-C. etal. “Cloning and Promoter Analysis of the Cotton Lipid Aharoni, A. et al. “Terpenoid Metabolism in Wild-Type and Transfer Protein Gene Lip3" Biochimica et Biophysica Acta, 2000, Transgenic Arabidopsis Plants' The Plant Cell, Dec. 2003, pp. 2866 pp. 106-111, vol. 1487. 2884, vol. 15. Mahmoud, S.S. etal. "Metabolic Engineering of Essential Oil Yield Besumbes, O. et al. "Metabolic Engineering of Isoprenoid and Composition in Mint by Altering Expression of Deoxyxylulose Biosynthesis in Arabidopsis for the Production of Taxadiene, the Phosphate Reductoisomerase and Menthofuran Synthase” PNAS, First Committed Precursor of Taxol” Biotechnology and Jul. 17, 2001, pp. 8915-8920, vol. 98, No. 15. Bioengineering, Oct. 20, 2004, pp. 168-175, vol. 88, No. 2. Wang, E. et al. “Elucidation of the Functions of Genes Central to Hermann, S. R. et al. “Promoters Derived from Banana Bunchy Top Diterpene Metabolism in Tobacco Trichomes Using Post Virus-Associated Components S1 and S2 Drive Transgene Expres transcriptional Gene Silencing” Planta, 2003, pp. 686-691, vol. 216. sion in Both Tobacco and Banana' Plant Cell Rep. 2001, pp. 642-646, Hohn, T. et al. “Expression of a Fungal Sesquiterpene Cyclase Gene vol. 20. in Transgenic Tobacco” Plant Physiol. 1991, pp. 460-462, vol. 97. Iijima, Y. etal. “The Biochemical and Molecular Basis for the Diver gent Patterns in the Biosynthesis of Terpenes and Phenylpropenes in * cited by examiner U.S. Patent Aug. 25, 2015 Sheet 3 of 10 US 9,115,366 B2 20 - 15 - H 10 9. o 3. .9 o s X t 5 - O -T ----- - WT 35s TS NSTPS-02a TS FIGURE 5 U.S. Patent Aug. 25, 2015 Sheet 4 of 10 US 9,115,366 B2 100 s a. 50 C O - WT ihpTPS 10 FIGURE 6 s s CYPD16p s f C e35S-CYPD16p o 0.1 t s O s 0.01 - 0.001 FIGURE 7 U.S. Patent US 9,115,366 B2 IH8GHRHQ5) U.S. Patent US 9,115,366 B2 6CHRIÍTIÐIH U.S. Patent US 9,115,366 B2 {}ICHRIÍTIÐIH U.S. Patent Aug. 25, 2015 Sheet 9 of 10 US 9,115,366 B2 U.S. Patent Aug. 25, 2015 Sheet 10 of 10 US 9,115,366 B2 FIGURE 13A FIGURE 13B TS TS -- T5H CBT-dio CBT-diol Taxadiene FIGURE 3C FIGURE 3D Oxidized Taxadienc Taxadiene Af US 9,115,366 B2 1. 2 SYSTEM FOR PRODUCING TERPENOIDS IN division between primary and secondary metabolites takes PLANTS place through a tight regulation of the metabolic availability of GGPP. In this respect, it is relevant to note that plant species CROSS-REFERENCE TO RELATED which accumulate large amounts of diterpenes are equipped APPLICATION with specialised organs, the Secreting trichomes, dedicated to the synthesis thereof. Tobacco and in particular Nicotiana This application is the U.S. national stage application of Sylvestris, are a typical example where there is an abundant International Patent Application No. PCT/FR2006/000188, GGPP pool in the trichomes in order to ensure a high flow of filed Jan. 27, 2006, the disclosure of which is hereby incor cembranoid synthesis, and hence the high accumulation porated by reference in its entirety, including all figures, 10 thereof at the surface of the aerial parts. tables and amino acid or nucleic acid sequences. The steps leading to the biosynthesis of CBT-diol in tobacco have been partially elucidated and can be broken FIELD OF THE INVENTION down into two different parts: biosynthesis of the universal precursor of all diterpenes, The invention relates to a method for producing com 15 geranylgeranyl pyrophosphate (GGPP), via the pounds of interest in plants and to genetically modified plants so-called “Rohmer pathway (Rohmer et al., 1996), prepared for use in said method. The invention also relates to takes place in the chloroplast. genetically modified plants enabling an enhanced efficiency biosynthesis of CBT-diol from GGPP. Wang and Wagner of transformation. (2003) have proposed the following biosynthetic path INTRODUCTION way: Trichomes are organs located at the Surfaces of the aerial GGPP-CBT-o-eCBT-dio. parts of higher plants (reviewed in Wagner et al., 2004). They The first cyclization step would be carried out by an take various forms and are classified into two main categories. 25 enzyme from a large family of enzymes known as terpene The first includes hairs, or non-secreting trichomes, unicel synthases (Bohlmann et al., 1998). The diterpene synthase of lular or multicellular. They do not secrete substances to the tobacco would use GGPP as substrate to form CBT-ol. The exterior, or at least not in appreciable amounts. The second second step whereby CBT-diol is produced from CBT-ol is a group comprises all trichomes described as secreting or glan hydroxylation catalyzed by an enzyme from the cytochrome dular, which have an increased capacity to synthesize and 30 P450 family.
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