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(12) United States Patent (10) Patent No.: US 9,351,507 B2 Zaplin Et Al US009351507 B2 (12) United States Patent (10) Patent No.: US 9,351,507 B2 Zaplin et al. (45) Date of Patent: May 31, 2016 (54) METHOD OF PREPARING FOOD USING 7,045,326 B2 5, 2006 Cases et al. RCE OL 7,109,392 B1 9/2006 Broglie et al. 7,135,617 B2 11/2006 Lardizabal et al. 7,244,599 B2 7/2007 Tanner et al. (71) Applicants: Ella Zaplin, Wagga Wagga (AU); 7,417, 176 B2 8/2008 Lardizabal et al. Sadequr Rahman, Nicholls (AU); 7,521,593 B2 4/2009 Regina et al. Zhongyi Li, Kaleen (AU); Qing Liu, 7,589,253 B2 9, 2009 Green et al. Girralang (AU); Surinder Pal Singh, 7,619, 105 B2 11/2009 Green et al. 7,667,114 B2 2/2010 Morell et al. Downer (AU); Robert Charles de 7,700,139 B2 4/2010 Bird et al. Feyter, Monash (AU) 7,700,826 B2 4/2010 Morell et al. 7,741,532 B2 6/2010 Lardizabal et al. (72) Inventors: Ella Zaplin, Wagga Wagga (AU); 7,790,955 B2 9/2010 Li et al. Sadequr Rahman, Nicholls (AU); 7,807,849 B2 10/2010 Singh et al. 7,812,221 B2 10/2010 Morell et al. Zhongyi Li, Kaleen (AU); Qing Liu, 7,834,248 B2 11/2010 Green et al. Girralang (AU); Surinder Pal Singh, 7,834,250 B2 11/2010 Singh et al. Downer (AU); Robert Charles de 7,888.499 B2 2/2011 Morell et al. Feyter, Monash (AU) 7,892,803 B2 2/2011 Tanner et al. 7.919, 132 B2 4/2011 Regina et al. 7,932.438 B2 4/2011 Singh et al. (73) Assignee: COMMONWEALTH SCIENTIFIC 7,932.440 B2 4/2011 Reid et al. AND INDUSTRIAL RESEARCH 7.993,686 B2 8, 2011 Bird et al. ORGANISATION, Campbell (AU) 8,049,069 B2 11/2011 Wu et al. 8,071,341 B2 12/2011 Singh et al. (*) Notice: Subject to any disclaimer, the term of this 8, 106,226 B2 1/2012 Singh et al. patent is extended or adjusted under 35 8, 115,087 B2 2/2012 Regina et al. 8, 158,392 B1 4/2012 Singh et al. U.S.C. 154(b) by 187 days. 8, 178,759 B2 5, 2012 Morell et al. 8, 188,336 B2 5, 2012 Li et al. (21) Appl. No.: 14/021,173 8,269,082 B2 9/2012 Millar et al. 8,288,572 B2 10/2012 Singh et al. (22) Filed: Sep. 9, 2013 8,501,262 B2 8, 2013 Bird et al. 8,530,724 B2 9, 2013 Whitelaw et al. (65) Prior Publication Data 8,535,917 B2 9/2013 Singh et al. 8,716,555 B2 5, 2014 Liu et al. US 2014/O12O225A1 May 1, 2014 8,735,111 B2 5, 2014 Vanhercke et al. 8,809,026 B2 8/2014 Vanhercke et al. 8,921,652 B2 12/2014 Liu et al. Related U.S. Application Data 9,057,075 B2 6, 2015 Liu et al. (62) Division of application No. 12/309.276, filed as (Continued) application No. PCT/AU2007/000977 on Jul. 13, 2007. FOREIGN PATENT DOCUMENTS (30) Foreign Application Priority Data EP 1806398 7/2007 EP 1837397 9, 2007 Jul. 14, 2006 (AU) ................................ 2OO6903810 (Continued) (51) Int. Cl. OTHER PUBLICATIONS CI2N 15/82 (2006.01) A2.3L I/OI (2006.01) Greenwell et al. (2010) “Placing microalgae on the biofuels priority A23D 9/00 (2006.01) list: a review of the technological challenges' J. R. Soc. Interface CIIB I/O (2006.01) 7:7O3-726. (52) U.S. Cl. CPC ................. A23L I/0107 (2013.01); A23D 9/00 (Continued) (2013.01); CIIB I/10 (2013.01); C12N 15/8218 (2013.01); C12N 15/8247 (2013.01) (58) Field of Classification Search Primary Examiner — Elizabeth McElwain None (74) Attorney, Agent, or Firm — John P. White; Gary J. See application file for complete search history. Gershik; Cooper & Dunham LLP (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS The present invention relates to methods of preparing food 4,948,811 A 8/1990 Spinner et al. using rice oil which has increased levels of oleic acid and 5,500,361 A 3/1996 Kinney et al. 6,100,077 A 8/2000 Sturley et al. decreased palmitic and linoleic acids, for increased Stability 6,344.548 B1 2/2002 Farese et al. to oxidation and health benefits. 6,432,684 B1 8/2002 Mukerji et al. 6,998,516 B2 2/2006 Brar et al. 7,001,771 B1 2/2006 Morell et al. 7 Claims, 38 Drawing Sheets US 9,351,507 B2 Page 2 (56) References Cited Jain et al., (2000) “Enhancement of seed oil content by expression of glycerol-3-phosphate acyltransferase genes' Biochemical Society U.S. PATENT DOCUMENTS Transactions 28(6): 958-961. Jako et al., Seed-Specific Over-Expression of an Arabidopsis cDNA 2002/0104124 A1 8, 2002 Green et al. Encoding a Diacylglycerol Acyltransferase Enhances Seed Oil Con 2004/0221335 A1 11/2004 Shewmaker et al. tent and Seed Weight. Plant Physiology, 2001, 126:861-874. 2005/01066.97 A1 5, 2005 Cases et al. 2005, O262.588 A1 11/2005 Dehesh et al. James et al (2010) “Disruption of the Arabidopsis CGI-58 2006.0053512 A1 3, 2006 Bao et al. homologue produces Chanarin-Dorfman-like lipid droplet accumu 2006/0094.088 A1 5/2006 Picataggio et al. lation in plants.” 107(41):17832-17838 and supporting information 2006/0206963 A1 9, 2006 Voelker et al. pp. 1-3. 2008/0268539 A1 10/2008 Singh et al. Kargiotidou et al., (2008) “Low temperature and light regulate delta 2008/0311580 A1 12/2008 Abrahams et al. 12 fatty acid desaturases (FAD2) at a transcriptional level in cotton 2009 OO61492 A1 3/2009 Benning et al. (Gossypiumhirsutum)” Journal of Experimental Botany 2008 59(8): 2009,0308041 A1 12/2009 Whitelaw et al. 2043-2056. 2010, O184130 A1 7/2010 Koprowski et al. Karmakar et al. (2010) “Properties of various plants and animals 2010, 0221400 A1 9/2010 Chapman et al. feedstocks for biodiesel production” Bioresource Technology 2011 OO15415 A1 1/2011 Singh et al. 101:72O1-7210. 2011/0045127 A1 2/2011 Ralet al. Kelly et al. (2012) “Suppression of the Sugar-DEPENDENT1 2011/0054198 A1 3/2011 Singh et al. 2011/O190521 A1 8/2011 Damcevski et al. triacylglycerol lipase family during seed development enhances oil 2011/02O1065 A1 8/2011 Singh et al. yield in oilseed rape (Brassica napus L.) Plant Biotechnology Jour 2011/0218348 A1 9, 2011 Zhou et al. nal, pp. 1-7. 2011/02233.11 A1 9, 2011 Liu et al. Kelly et al., (2011) “Seed Storage Oil Mobilization Is Important But 2011/0229623 A1 9, 2011 Liu et al. Not Essential for Germination or Seedling Establishment in 2011/0281.818 A1 11/2011 Jenkins et al. Arabidopsis' Plant Physiology, vol. 157, pp. 866-875. 2011/0314725 A1 12/2011 Petrie et al. Kozell et al. (1996) "Optimizing expression of transgenes with an 2012fOO16144 A1 1/2012 Petrie et al. emphasis on post-transcriptional events.” Plant Molecular Biology, 2012/0041218 A1 2/2012 Singh et al. 32:393-405. 2012/0114770 A1 5/2012 Regina et al. Lardizabal et al. (2001) “DGAT2 Is a New Diacylglycerol 2012/0129805 A1 5, 2012 Li et al. Acyltransferase Gene Family” J. Biol. Chem. 276:38862-38869. 2012/0208198 A1 8/2012 Bogs et al. 2013, O115362 A1 5/2013 Regina et al. Lardizabal et al. (2008) “Expression of Umbellopsis ramanniana 2013,0164.798 A1 6, 2013 Vanhercke et al. DGAT2A in Seed Increases Oil in Soybean” Plant Physiol. 148: 2013,0247451 A1 9, 2013 Vanhercke et al. 89-96. 2014/0256006 A1 9, 2014 Vanhercke et al. Liu etal. (2010) “Producing biodiesel from high free fatty acids waste 2015,0176017 A1 6/2015 Liu et al. cooking oil assisted by radio frequency heating” Fuel 89:2735-2740. Liu et al., Genetic modification of cotton seed oil using inverted FOREIGN PATENT DOCUMENTS repeat gene-silencing techniques. Biochemical Society Transations, 2000, 28(6):927-929. EP 1944375 T 2008 Liu et al., (1999) “Cloning and Sequence Analysis of a Novel Mem WO WO98,55631 12/1998 ber (Accession No. Y 101 12) of the Microsomal w-6 Fatty Acid WO WO99/49050 9, 1999 Desaturase Family from Cotton” Plant Physiol. (PGR 99-063) WO WO99.67268 12/1999 120:339. WO WO99,67403 12/1999 Luetal. (2011) “New frontiers in oilseed biotechnology: meeting the WO WOOO/O1713 1, 2000 global demand for vegetable oils for food, feed, biofuel, and indus WO WOOOf 11176 3, 2000 trial applications' Current Opinion in Biotechnology, 22:252-259. WO WOOO,32756 6, 2000 WO WOOO,32793 6, 2000 Maher and Bressler (2007) “Pyrolysis of triglyceride materials for WO WOOO,361.14 6, 2000 the production of renewable fuels and chemicals' Bioresource Tech WO WOOOf 60.095 10, 2000 nology 98:2351-2368. WO WOOOf 66750 10, 2000 O'Brien, (2002) Cottonseed Oil. In: F.D. Gunstone (Ed.) Vegetable WO WOOOf 66749 11, 2000 Oils in Food Technology: Composition, Properties and Uses. WO WOO3,O78639 9, 2003 Blackwell Publishing, Oxford, pp. 203-223. WO WO 03/080802 10, 2003 Okuley et al. Arabidopsis FAD2 Gene Encodes the Enzyme that is WO WO 04/001001 12/2003 Essential for Polyunsaturated Lipid Synthesis. Plant Cell, 1994, WO WO 2004/O11671 2, 2004 6:147-158. WO WO 2005/003322 1, 2005 Parthibane etal. (2012) "Oleosin Isa Bifunctional Enzyme That Has WO WO 2005/063988 7/2005 Both Monoacylglycerol Acyltransferase and Phospholipase Activi WO WO 2005,103253 11, 2005 ties J.
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