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Improved Cottonseed Oil and Uses Verbessertes Leinsamenöl Und Seine Verwendung Huile De Coton Améliorée Et Utilisations

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Improved Cottonseed Oil and Uses Verbessertes Leinsamenöl Und Seine Verwendung Huile De Coton Améliorée Et Utilisations (19) TZZ ¥___T (11) EP 2 315 519 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C12N 9/02 (2006.01) C12N 9/10 (2006.01) 17.08.2016 Bulletin 2016/33 C12N 9/16 (2006.01) C12N 5/14 (2006.01) C12N 15/82 (2006.01) (21) Application number: 09799857.9 (86) International application number: (22) Date of filing: 21.07.2009 PCT/AU2009/000929 (87) International publication number: WO 2010/009499 (28.01.2010 Gazette 2010/04) (54) IMPROVED COTTONSEED OIL AND USES VERBESSERTES LEINSAMENÖL UND SEINE VERWENDUNG HUILE DE COTON AMÉLIORÉE ET UTILISATIONS (84) Designated Contracting States: WO-A2-2004/000871 JP-A- S57 208 957 AT BE BG CH CY CZ DE DK EE ES FI FR GB GR US-A- 5 955 650 US-A1- 2002 104 124 HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL US-A1- 2004 107 460 US-A1- 2006 053 512 PT RO SE SI SK SM TR US-A1- 2006 206 963 US-B1- 7 109 392 (30) Priority: 21.07.2008 US 135554 P • DÖRMANN PETER ET AL: "Accumulation of palmitate in Arabidopsis mediated by the (43) Date of publication of application: acyl-acyl carrier protein thioesterase FATB1", 04.05.2011 Bulletin 2011/18 PLANT PHYSIOLOGY, AMERICAN SOCIETY OF PLANT PHYSIOLOGISTS, ROCKVILLE, MD, US, (73) Proprietor: Commonwealth Scientific and vol. 123, no. 2, 1 June 2000 (2000-06-01), pages Industrial Research 637-643, XP002517758, ISSN: 0032-0889, DOI: Organisation DOI:10.1104/PP.123.2.637 Acton ACT 2601 (AU) • BAO XIAOMING ET AL: "Carbocyclic fatty acids in plants: Biochemical and molecular genetic (72) Inventors: characterization of cyclopropane fatty acid •LIU,Qing synthesis of Sterculia foetida", PROCEEDINGS Giralang OF THE NATIONAL ACADEMY OF SCIENCES, Australian Capital Territory 2617 (AU) NATIONAL ACADEMY OF SCIENCES, • GREEN, Allan, Graham WASHINGTON, DC; US, vol. 99, no. 10, 14 May Red Hill 2002 (2002-05-14), pages 7172-7177, Australian Capital Territory 2603 (AU) XP002335028, ISSN: 0027-8424, DOI: • SINGH, Surinder, Pal DOI:10.1073/PNAS.092152999 Downer • LIU, Q. ET AL.: ’High-Stearic and High-Oleic Australian Capital Territory 2602 (AU) Cottonseed Oils Produced by Hairpin RNA-Mediated Post-Transcriptional Gene (74) Representative: Almond-Martin, Carol et al Silencing’ PLANT PHYSIOLOGY vol. 129, no. 4, Ernest Gutmann - Yves Plasseraud S.A.S. 2002, pages 1732 - 1743, XP002291940 88, Boulevard des Belges • LIU, Q. ET AL.: ’Genetic modification of cotton 69452 Lyon Cedex 06 (FR) seed oil using inverted-repeat gene-silencing techniques’ BIOCHEMICAL SOCIETY (56) References cited: TRANSACTIONS. vol. 28, no. 6, 2000, pages 927 EP-A1- 1 806 398 EP-A1- 1 837 397 - 929, XP002306925 EP-A1- 1 944 375 WO-A1-2008/006171 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 315 519 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 315 519 B1 • DATABASE GENBANK 02 October 2005 XP008143321 Database accession no. AY574036 • DATABASE GENBANK 02 October 2005 XP008143323 Database accession no. AY574037 • DATABASE GENBANK 02 October 2005 XP008143324 Database accession no. AY574038 • BAO XIAOMING ET AL: "Characterization of cyclopropane fatty-acid synthase from Sterculia foetida", JOURNAL OF BIOLOGICAL CHEMISTRY, AMERICAN SOCIETY FOR BIOCHEMISTRY AND MOLECULAR BIOLOGY, US, vol. 278, no. 15, 11 April 2003 (2003-04-11), pages 12846-12853, XP002335027, ISSN: 0021-9258, DOI: 10.1074/JBC.M212464200 2 EP 2 315 519 B1 Description FIELD 5 [0001] The present specification relates to the production of cotton plants and seeds and oil prepared therefrom having elevated levels of oleic and reduced levels of palmitic and linoleic acids. Furthermore, cottonseeds having low levels of cyclopropane and/or cyclopropene fatty acids and/or reduced levels of gossypol are described herein. The specification also describe FatB and CPA-FAS nucleotide and amino acid sequences derived from cotton facilitating,inter alia the direct modification of plant oil content and/or composition. 10 BACKGROUND [0002] Cotton is a dual purpose crop, producing both fiber and seed as valuable primary agricultural products. Normally, cottonseed products, including hulls (26%), linters (9%), oil (16%) and cottonseed meal (45%) represent approximately 15 15% of the farm value of the cotton crop (Cherry and Leffler, Seed. In "Cotton, agronomy monograph No. 24" (eds RJ Kohel, CF Lewis) pp. 511-569. Crop Science Society of America, Madison, WI, USA, 1984), while lint provides most of the remaining 85% of the value. Cottonseed oil is the most valuable product derived from cottonseed. [0003] Cottonseed oil has a long tradition of use in food processing. Since cottonseed oil has a bland, neutral flavor that does not mask the inherent flavor of food, it is a popular and widely used oil for deep frying in the snack food and 20 food service sector (Jones and King, Cottonseed Oil. National Cottonseed Products Associations, Inc. and the Cotton Foundation, Memphis, TN, USA, 1993). Cottonseed oil is also commonly used as an ingredient in marinades, dressings, pastries, margarines, and shortenings. [0004] The nutritional and industrial value of cottonseed oil, like other vegetable oils, is affected by the composition of fatty acids in the oil, ie. the relative level of each the fatty acids in the oil, and the properties conferred by the carbo n 25 chain length and level of unsaturation of each fatty acid. [0005] Isolated and purified cottonseed oil is composed mostly (>95%) of triacylglycerols (TAGs) that are synthesized and deposited during seed development. TAG molecules consist of three fatty acids esterified to a glycerol backbone, designated the sn-1, sn-2 and sn-3 positions. Briefly, the de novo biosynthesis of fatty acids in cotton seed, as in other oilseeds, occurs in the stroma of plastids during development and growth of the seeds, ie. before maturation. Fatty acids 30 are then exported from the plastids in the form of acyl-CoA thioesters to the cytoplasmic endomembrane systems (endoplasmic reticulum, ER) where modification of fatty acids occurs after transfer of the acyl groups from the CoA thioesters to phospholipids by acyltransferases. This is followed by TAG assembly and storage in the oleosomes. [0006] The biotin-containing enzyme acetyl-CoA carboxylase (ACCase) catalyses the first committed step in the path- way by activating acetyl-CoA to the three carbon intermediate, malonyl-CoA, by addition of a carboxyl group. The malonyl 35 group is then transferred from CoA to an acyl-carrier protein (ACP), which serves as the carrier for the growing fatty acid chain. Malonyl-ACP is reacted with a second acetyl-CoA condensing enzyme, ketoacyl-ACP synthase III (KASIII), re- sulting in a four carbon chain. The repeated process of adding two-carbon units on the elongated fatty acid chain is catalyzed by KASI leading to the formation of palmitoyl-ACP. KASII catalyzes the elongation of palmitoyl-ACP to stearoyl- ACP. A soluble stearoyl-ACP Δ9-desaturase introduces the first double bond into stearoyl-ACP to convert it to oleoyl- 40 ACP in the plastid. The extended, saturated fatty acyl chain and the monounsaturated oleate are cleaved off the ACP by a specific thioesterase enzyme, FatB or FatA, respectively, enabling them to exit the plastid and enter the cytoplasm. Saturated fatty acids released into the cytoplasm are not further modified. However, oleic acid can be further modified on the endoplasmic reticulum (ER) membranes by the action of membrane-bound desaturases. Phosphatidylcholine (PC)-bound acyl chains serve as a substrate for ER localized, lipid modifying enzymes, such as fatty acid desaturase 45 2 (FAD2) which introduces a double bond into oleic acid on the sn-2 position of PC to produce linoleic acid. All the modified and unmodified fatty acyl groups then form a pool while attached to CoA. In cotton, but not in other temperate zone oilseeds, oleic acid may be used as substrate for cyclopropanation catalysed by cyclopropane fatty acid synthase to produce dihydrosterculic acid. This fatty acid is subsequently desaturated to produce sterculic acid and then α-oxidased to produce malvalic acids. Finally fatty acyl groups are incorporated into storage lipids via the Kennedy pathway by the 50 sequential esterification of glycerol-3-phosphate by the action of a series of TAG assembly enzymes. [0007] The enzyme acyl-ACP thioesterase (FatB) (EC 3.1.2.14) catalyses the hydrolysis of the thioester bond between the acyl moiety and ACP in acyl-ACP and the release of free fatty acid in the plastid. The free fatty acid is then re- esterified to CoA in the plastid envelope as it is transported out of the plastid. FatB belongs to a class of nuclear encoded, soluble, fatty acid thioesterase (FAT) enzymes which are first translated as a precursor proteins. The substrate specificity 55 of the FAT enzymes in the plastid is therefore involved in determining the spectrum of chain length and degree of saturation of the fatty acids exported from the plastid. FAT enzymes can be classified into two classes based on their substrate specificity and nucleotide sequences, FatA and FatB (Jones et al., Plant Cell 7: 359-371, 1995). FatA prefers oleoyl-ACP as substrate, while FatB shows higher activity towards saturated acyl-ACPs of different chain lengths. Genes 3 EP 2 315 519 B1 encoding FatB enzyme were first isolated from plant species accumulating medium chain-length saturated fatty acids such as lauric acid (C12:0) from California bay tree ( Umbellularia californica).
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