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(12) United States Patent (10) Patent No.: US 9,725,399 B2 Petrie Et Al

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(12) United States Patent (10) Patent No.: US 9,725,399 B2 Petrie Et Al USO09725399B2 (12) United States Patent (10) Patent No.: US 9,725,399 B2 Petrie et al. (45) Date of Patent: Aug. 8, 2017 (54) LPID COMPRISING LONG CHAN (51) Int. Cl. POLYUNSATURATED FATTY ACDS C07C 69/587 (2006.01) CIIB I/O (2006.01) (71) Applicants: Commonwealth Scientific and (Continued) Industrial Research Organisation, (52) U.S. Cl. Acton, Australian Capital Territory CPC .............. C07C 69/587 (2013.01); A23D 9/00 (AU): Nuseed Pty Ltd, Laverton North, (2013.01); A61K 36/31 (2013.01): CIIB I/10 Victoria (AU); Grains Research and (2013.01); A61 K 2.236/00 (2013.01) Development Corporation, Barton, (58) Field of Classification Search Australian Capital Territory (AU) CPC .......................... C12N 15/8247; CO7C 69/587 See application file for complete search history. (72) Inventors: James Robertson Petrie, Goulburn (AU); Surinder Pal Singh, Downer (56) References Cited (AU); Pushkar Shrestha, Lawson U.S. PATENT DOCUMENTS (AU); Jason Timothy McAllister, Portarlington (AU); Robert Charles De 4,399.216 A 8, 1983 Axel et al. Feyter, Monash (AU); Malcolm David 5,004,863. A 4, 1991 Umbeck Devine, Vernon (CA) (Continued) (73) Assignees: COMMONWEALTH SCIENTIFIC FOREIGN PATENT DOCUMENTS AND INDUSTRIAL RESEARCH AU 667939 1, 1994 ORGANISATION, Campbell (AU): AU 200059710 B2 12/2000 NUSEED PTY LTD, Laverton North (Continued) (AU); GRAINS RESEARCH AND DEVELOPMENT CORPORATION, Barton (AU) OTHER PUBLICATIONS Ruiz-Lopez, N. et al., “Metabolic engineering of the omega-3 long (*) Notice: Subject to any disclaimer, the term of this chain polyunsaturated fatty acid biosynthetic pathway into trans patent is extended or adjusted under 35 genic plants' Journal of Experimental botany, 2012, vol. 63, pp. U.S.C. 154(b) by 0 days. 2397-2410. (Continued) (21) Appl. No.: 14/575,756 Primary Examiner – Yate K Cutliff (22) Filed: Dec. 18, 2014 (74) Attorney, Agent, or Firm — John P. White; Gary J. Gershik; Cooper & Dunham LLP (65) Prior Publication Data (57) ABSTRACT US 2015/O166928 A1 Jun. 18, 2015 The present invention relates to extracted plant lipid or microbial lipid comprising docosahexaenoic acid, and/or (30) Foreign Application Priority Data docosapentaenoic acid, and processes for producing the extracted lipid. Dec. 18, 2013 (AU) ................................ 2O139.05033 Jun. 27, 2014 (AU) ................................ 2O14902471 33 Claims, 10 Drawing Sheets . Y 8:3AS.215 (ALA) -- 8,,2, 3 (SA; 2:3:4,7 \ 2:SAS8, 4. EPAs - J & &i. : & :: 3. 3.9 (3A) -- 4:59,3,5,8,2; 22:6.4,, , 3.3f. A s----- 24:33.8125.8.2. 3-oxiciatic US 9,725,399 B2 Page 2 (51) Int. Cl. 7,081,356 B2 7/2006 Putten et al. A6 IK 36/3 (2006.01) 7,091,005 B2 8, 2006 Petrukhin et al. 7,109,392 B1 9/2006 Broglie et al. 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