Source: https://patents.justia.com/patent/8841097
Timestamp: 2019-05-24 03:34:43
Document Index: 84815898

Matched Legal Cases: ['Application No. 8', 'application No. 10', 'Art 112', 'Application No. 97937813', 'Application No. 97937813', 'Application No. 97937813']

US Patent for Process for producing unsaturated fatty acid-containing oils Patent (Patent # 8,841,097 issued September 23, 2014) - Justia Patents Search
Justia Patents Fat; Fatty Oil; Ester-type Wax; Higher Fatty Acid (i.e., Having At Least Seven Carbon Atoms In An Unbroken Chain Bound To A Carboxyl Group); Oxidized Oil Or FatUS Patent for Process for producing unsaturated fatty acid-containing oils Patent (Patent # 8,841,097)
Apr 21, 2006 - Suntory Holdings Limited
An edible oil obtained by culturing a microorganism belong to the genus Mortierella subgenus Mortierella in a medium containing a nitrogen source derived from soybean is discussed. The oils obtained have a low 24,25-methylenecholest-5-en-3β-ol content.
This is a Continuation of application Ser. No. 09/254,152, filed Feb. 26, 1999, now U.S. Pat. No. 7,091,244, which is a PCT National Stage of PCT/JP97/02989 filed Aug. 27, 1997, which claim priority to Japanese Patent Application No. 8-230210 filed Aug. 30, 1996. Each listed U.S. patent and/or application is incorporated by reference in its entirety.
Microorganisms belonging to the genus Mortierella, subgenus Mortierella are known as microorganisms which produce unsaturated fatty acids such as arachidonic acid, dihomo-γ-linolenic acid and eicosapentaenoic acid, and processes have been developed for efficient production of arachidonic acid, dihomo-γ-linolenic acid and eicosapentaenoic acid by fermentation using these microorganisms Japanese Unexamined Patent Publications No. 63-44891, No. 63-12290, No. 63-14696, No. 5-91887, No. 63-14697). In addition there is also known a process for producing Mead acid using mutant strains having reduced or defective in Δ12 desaturating activity, which are obtained by mutating microorganisms belonging to the genus Mortierella, subgenus Mortierella(Japanese Unexamined Patent Publication No. 5-91888).
Specifically, Lanting et al. (LANCET, Vol. 344, 1319-1322(1994)) have examined infants raised on breast milk and infants raised on infant powdered milk for 3 weeks or more after birth, with follow-up to 9 years of age, studying the incidence of minor damage to cranial nerves from a behavioral perspective, and have reported that the incidence of brain damage in children raised on infant powdered milk is twice that of children raised on breast milk. This shocking result suggests that higher unsaturated fatty acids such as DHA and arachidonic acid which are present in breast milk but virtually absent in infant powdered milk play a role in the development of the brain. Subsequent reports have also shown results suggesting that higher unsaturated fatty acids are connected with the development of the brain and retina.
Nevertheless, while unsaturated fatty acid-containing oils are considered to be highly safe, the issue of their microbial sources has prevented them from wide use throughout the world; meanwhile, in LIPIDS, Vol. 27, No. 6, 481-483(1992), Mortierella alpina 1S-4 was reported to produce 24,25-methylenecholest-5-en-3β-ol which to that time was not known to occur naturally. Thus, it has been desired to develop unsaturated fatty acid-containing oils obtained from microorganisms belonging to the genus Mortierella subgenus Mortierella which can be more safely utilized for foods and animal feeds.
According to the invention, unsaturated fatty acids are fatty acids with at least 16 carbon atoms and at least one double bond, among which higher unsaturated fatty acids are generally fatty acids with at least 1.8 carbon atoms and at least two double bonds, and as examples there may be mentioned γ-linolenic acid, dihomo-γ-linolenic acid, arachidonic acid, eicosapentaenoic acid and Mead acid.
The microorganisms used according to the invention include mutant strains or recombinant strains of microorganisms belonging to the genus Mortierella subgenus Mortierella(wild strains), i.e. those designed either to give a higher unsaturated fatty acid content in the oil, a higher total oil content, or both, compared to the amount produced by the original wild strain, when cultured using the same substrate.
The soybean-derived nitrogen source used for the invention is one with a nitrogen content of at least 2 wt %, preferably at least 3 wt % and more preferably at least 5% with respect to the total components except for water. The soybean-derived nitrogen source may be one or a combination of different types of defatted soybean or soybean subjected to heat treatment; acid treatment; alkali treatment; enzyme treatment; chemical modification; denaturation and/or renaturation by chemical and/or physical processing including heat treatment, acid treatment, alkali treatment, enzyme treatment, chemical modification, etc.; removal of a portion of the components with water and/or organic solvents; removal of a portion of the components by filtration and/or centrifugation; freezing; crushing; drying; sifting; etc., or a product of processing in the same manner as non-defatted soybean; as common candidates there may be mentioned soybean, defatted soybean, soybean flakes, edible soybean protein, okara, soy milk and roasted-soybean flour (kinako), among which are particularly preferred heat-denatured defatted soybean, and especially heat-denatured defatted soybean from which the ethanol-soluble components have been further removed.
Also, when necessary trace nutrient sources may be used, including inorganic salts such as potassium phosphate, potassium dihydrogen phosphate and other phosphate salts, ammonium sulfate, sodium sulfate, magnesium sulfate, iron sulfate, copper sulfate, magnesium chloride, calcium chloride, etc. and vitamins.
A fermenter, especially culturing fermenter with aeration and agitation or air-lift culturing fermenter may be used for submerged culturing with aeration to enable production with yields suited for unsaturated fatty acid-containing oils as commercial products. In such cases, the unsaturated fatty acid-containing oil can be even more efficiently produced by maintenance during the culturing to a glucose concentration of at least 0.3 wt % and/or an average glucose concentration of at least 0.5 wt %, preferably a glucose concentration of at least 0.5 wt % and/or an average glucose concentration of at least 0.7 wt %, and more preferably a glucose concentration of 0.5-5 wt % and/or an average glucose concentration of 0.7-3 wt %, for at least 3 days after the start of culturing. For example, arachidonic acid can be produced at 100 mg or more, and preferably 120 mg or more to one gram of dry cells.
The oil properties of the arachidonic acid containing oil are such that the triglyceride content is 90% or greater, the moisture content is 0.1% or lower, the acid value is 0.5 or lower and the peroxide value is 5 or lower, while the color is ≦50 yellow and ≦10 by the Lovibond method in a 133.4 mm cell, and the fatty acid composition is 20 to 54%, with preferably 30 to 50% arachidonic acid, 0.2 to 0.7% myristic acid, 10 to 16% palmitic acid, 4 to 10% stearic acid, 5 to 15% oleic acid, 5 to 15% linolic acid, 1 to 5% γ-linolenic acid, 0.1 to 2% α-linolenic acid, 1 to 6% dihomo-γ-linolenic acid, 0 to 1% eicosapentoenoic acid and 2 to 7% lignoceric acid.
Using Mortierella elongata IFO8570 as the arachidonic acid-producing cell line, 1400 L of a medium containing 2% glucose, 1% edible soybean protein trade name: Esusan Meat, product of Ajinomoto Co.) and 0.1% rapeseed oil was placed in a 2000 L fermenter equipped with an agitator and aerator and culturing with aeration and agitation was initiated under conditions of 28° C. temperature, 1.0 vvm aeration 80 rpm agitation and 1.0 kg/cm2G headspace pressure. The glucose concentration was kept at 1.5% by feeding glucose, and after culturing for 7 days the cells were recovered by filtration and subjected to oil extraction. As a comparative example, culturing and oil extraction were carried out in the same manner using 1% yeast extract instead of the edible soybean protein.
TABLE 1 Desmos- 24,25-methylene terol Total cholest-5-en-3β-ol compo- sterol Arachidonic compositional sitional cont- acid ratio (A) ratio (B) A/B ent* content**
Exam- 30% 65% 0.46 1% 8% ple Comp. 65% 27% 2.41 1% 9% Exam- ple *Sterol content in oil **Arachidonic acid content with respect to total fatty acids in oil
TABLE 2 Desmos- 24,25-methylene terol Total cholest-5-en-3β-ol compo- sterol Arachidonic compositional sitional cont- acid ratio (A) ratio (B) A/B ent* content**
Exam- 25% 53% 0.47 1.2% 48% Comp. 68% 16% 4.25 1.1% 46% Exam- ple *Sterol content in oil **Arachidonic acid content with respect to total fatty acids in oil
TABLE 3 24,25- methylene cholest-5- Desmos- en-3β-ol terol Total compo- compo- sterol Arachidonic sitional sitional cont- acid ratio (A) ratio (B) A/B ent* content**
Mortierella 5% 67% 0.07 0.9% 25% alpina ATCC32221 Comp. 37% 28% 1.32 0.8% 20% Example Mortierella 5% 35% 0.14 0.9% 18% alpina ATCC42430 Comp. 40% 25% 1.60 1.0% 18% Example *Sterol content in oil **Arachidonic acid content with respect to total fatty acids in oil
Color (Lovibond method, 133.4 mm cell): yellow: 20.1, red: 1.4
arachidonic acid 44.4% myristic acid 0.6% palmitic acid 14.6% stearic acid 8.8% oleic acid 6.3% linolic acid 10.2% γ-linolenic acid 3.2% α-linolenic acid 0.8% dihomo-γ-linolenic acid 5.2% eicosapentoenoic acid 0.2% lignoceric acid 4.8%
Total sterol content: 1.0%
24,25-methylenecholest-5-en-3β-ol compositional ratio: 24%
The arachidonic acid-containing oil obtained in Example 4 was appropriately mixed with fish oil and vegetable oil to obtain an essential fatty acid-adjusted oil. In addition to the essential fatty acid-adjusted oil the raw materials and components listed below were prepared for formulation of 100 kg of powdered infant formula. After dissolving, mixing and refining the raw materials according to conventional methods, they were sterilized, concentrated and homogenized, and then spray dried to obtain powdered infant formula.
1. A process for producing an unsaturated fatty acid-containing oil comprising:
(a) culturing a microorganism belonging to the genus Mortierella subgenus Mortierella in a liquid medium containing a nitrogen source derived from soybean in a fermenter, wherein the ratio of the nitrogen source derived from soybean with respect to the total nitrogen source in the medium is at least 86%, and
(b) collecting the unsaturated fatty acid-containing oil from the cultured product,
wherein the unsaturated fatty acid-containing oil has a 24,25-methylenecholest-5-en-3β-ol compositional ratio of 35% or lower, a 24,25-methylenecholest-5-en-3β-ol compositional ratio in a proportion of 1.2 or less with respect to the desmosterol compositional ratio, and an arachidonic acid content of 30 to 50%, and wherein the culture step is carried out while maintaining i) a glucose concentration within the range of 0.5 to 5 wt % during the first 3 days of culturing, and/or ii) an average glucose concentration within the range of 0.7 to 3 wt % during the first 3 days of culturing.
2. The process of claim 1, wherein said nitrogen source derived from soybean has a nitrogen content of at least 2 wt % with respect to the total components except for water.
3. The process of claim 1, wherein said nitrogen source derived from soybean is from defatted soybean subjected at least to heat denaturation.
4. The process of claim 1, wherein said cultured product is (a) culture broth taken during production of the oil by the cultured microorganisms or after sterilization of the culture broth, (b) culture broth obtained at the end of culturing or after sterilization of the culture broth, (c) the cultured microorganisms collected from either (a) or (b), or (d) a dry form of the cultured product.
5. The process of claim 1, wherein said fermentor is a fermentor equipped with agitator and air sparger or an air-lift fermentor.
6. The process of claim 1, wherein the culturing step is carried out for 3 to 20 days.
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Declaration of Angela Tsetsis submitted in opposition to EP 0 957 173 B1 Jun. 22, 2005.
Declaration of Chris Lindsay submitted in opposition to EP 0 957 173 B1 Jun. 22, 2005.
Declaration of Sandy Diltz submitted in opposition to EP 0 957 173 B1 Jun. 22, 2005.
First declaration of Dr Fujikawa submitted in opposition to EP 0 957 173 B1 Sep. 5, 2006.
Declaration of Kenji Katano submitted in opposition to EP 0 957 173 B1 Sep. 5, 2006.
Exhibit entitled “D23: Sixteen invoices and ‘Packing Slip’ documents in respect of A017-40-DS oil with dates in the period from Apr. 19, 1996 to Aug. 23, 1996,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Second Declaration by Angela Tsetsis including two Annexes submitted in opposition to EP 0 957 173 B1.
Exhibit entitled “D25: Nutricia press release,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D26: Certificate of analysis for A017-40-DS,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Second Declaration by Chris Lindsay submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D28: Two invoices in respect of sales of AO11-DS oil,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Second Declaration of Sandy Diltz submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D30: Two invoices in respect of sales of A013-DS oil,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D31: Text of email from publishers of Boswell et al, Food Chem. Toxicology 34 (1995) 585-593,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Description of Opponent I fermentation experiments submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D32(8): Peak assignment of 24,25-methylenecholest-5-en-3β-01 (24,25-M) and ergosta-5,25-dien-3b-ol (ergosta-5,25) by GC-MS,” submitted in opposition to EP 0 957 173 B1 Jul. 3, 2008.
Label from Arasco A017-40-DS submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Analysis of Arasco A017-40DS submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Declaration of Dr J. H. Wolf submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Declaration of Dr. A. Carvalho De Souza submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
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Exhibit entitled “D24a: Product information on Sigma S9633 soy flour,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Exhibit entitled “D25a: Product information on soy flour from Cargill,” submitted in opposition to EP 0 957 173 B1 Dec. 21, 2007.
Second declaration of Dr. Fujikawa submitted in opposition to EP 0 957 173 B1 Feb. 13, 2008.
Declaration of Dr. Higashiyama submitted in opposition to EP 0 957 173 B1 Feb. 13, 2008.
Exhibit entitled “D41: Extracts from Fungal Nutrition and Physiology, Michael Garraway and Robert Evans, Wiley 1984,” submitted in opposition to EP 0 957 173 B1 Nov. 30, 2008. ( Fungal Nutrition and Physiology, Michael Garraway and Robert Evans, eds., Wiley, New York, pp. 172-173, 193-195, 1984.).
Exhibit entitled “D42: Fermentation of M. alpina ATCC32222 using the protocol as described in Example 7 of WO 96/21037 and analysis of oil obtained therefrom (Joe Pfeifer & Sandy Diltz),” submitted in opposition to EP 0 957 173 B1 Nov. 30, 2008.
Exhibit entitled “D43: HOSO Sterol Analysis,” submitted in opposition to EP 0 957 173 B1 Nov. 30, 2008.
Exhibit entitled “D45: Analysis of Arasco AO17-40-DS oil by silica gel chromatography,” submitted in opposition to EP 0 957 173 B1 Nov. 3, 2008.
Exhibit entitled “Determination [of] desmosterol and 24,25-methylenecholest-5-en-3β-ol in high oleic sunflower oil (HOSO),” submitted in opposition to EP 0 957 173 B1 Jul. 3, 2008.
Second declaration by Dr. Higashiyama and third declaration by Dr. Fujikawa submitted in opposition to EP 0 957 173 B1, Jan. 29, 2009.
Opposition to EP 0 957 173 B1, Decision Revoking the European Patent, filed Jun. 6, 2008.
Exhibit entitled “D53: Sterol analysis of oils produced in fermentors using defatted soybean as nitrogen source,” submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Mar. 23, 2009.
Exhibit entitled “D52: Peak assignment of 24,25-methylenecholest-5-en-3β-ol (24,25M) and ergosta-5,25-dien-3β-ol (egosta-5,25) by means of NMR, GC-FID and GC-MS,” submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Mar. 23, 2009.
Exhibit entitled “D50: Results of sterol analysis of oils obtained as described in D49,” submitted in In re EP 0 957 173 Bl, Appeal T1540/08-3304, Mar. 25, 2009.
Exhibit entitled “D49: Fermentation of ATCC 32222 using soy derived nitrogen at two nitrogen levels and two dissolved oxygen levels,” submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Mar. 25, 2009.
Declaration by Raymond Michael Gladue, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Mar. 31, 2009.
Letter relating to Appeal Procedure, submitted in in re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 16, 2011.
Marked OD Decision of Jan. 15, 2010 from In re EP 1 454 990 B1, Appeal T0716/10, pp. 5-7, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 16, 2011.
Exhibit D56, Collated Data & Graph Annex, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 16, 2011.
Exhibit D54, Declaration of Nozomu Kamada, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 16, 2011.
Exhibit D55, Declaration No. 2 of Nozomu Kamada, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 16, 2011.
Response to further submissions letter of the patent proprietor, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Aug. 5, 2011.
Communication relating to Appeal Procedure, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Aug. 8, 2011.
Exhibit D57 from In re EP 1 454 990 B1, Appeal T0716/10, Declaration of Cindy Panker, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Aug. 8, 2011.
Exhibit D59 from In re EP 1 454 990 B1, Appeal T0716/10, Declaration of Ray Gladue, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Aug. 8, 2011.
Letter dealing with oral proceedings during the appeal procedure and Exhibits D56A, D56B, and D56C, submitted In re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 11, 2011.
Exhibit D60, Fourth Declaration of Shigeaki Fujikawa (first submitted Sep. 11, 2011, without execution), submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 14, 2011.
Letter dealing with oral proceedings during the appeal procedure, submitted in re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 11, 2011.
Exhibit D57, graph compositional ratio relative to total sterols, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 11, 2011.
Exhibit D58, graph compositional ratio relative to desmosterol, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 11, 2011.
Exhibit D59, graph compositional ratio relative to total sterols with lower limit of 5%, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Sep. 11, 2011.
Letter dealing with oral proceedings during the appeal procedure, submitted In re EP 0 957 173 B1, Appeal T1540/08-3304, Oct. 4, 2011.
Exhibit D60, Statistical analysis of premise of Suntory with respect to ergosta as submitted by Suntory on Sep. 12, 2011, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Oct. 4, 2011.
Communication of the Board of Appeal, mailed in In re EP 0 957 173 B1, Appeal T1540/08-3304, Oct. 6, 2011.
Minutes of the public oral proceedings before the Technical Board of Appeal 3.3.04 of Oct. 12, 2011, mailed in In re EP 0 957 173 B1, Appeal T1540/08-3304, Oct. 19, 2011.
Decision of the Technical Board of Appeal 3.3.04 of Oct. 12, 2011, mailed in In re EP 0 957 173 B1, Appeal T1540/08-3304, Mar. 7, 2012.
Petitions for Review of Decision No. T1540/08-3.3.04 according to Art 112a EPC, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, May 16, 2012.
Communication from the Enlarged Board of Appeal pursuant to Articles 13 and 14(2) RPEBA, mailed in In re EP 0 957 173 B1, Appeal T1540/08-3304, Jan. 25, 2013.
Letter relating to review procedure, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Apr. 3, 2013.
Letter relating to review procedure with Declaration of Gerard Patrick Stoner and Annexes 1-5, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Jul. 16, 2013.
Letter relating to review procedure, submitted in In re EP 0 957 173 B1, Appeal T1540/08-3304, Jul. 17, 2013.
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Declaration of Professor Andrew James Sinclair submitted in opposition to European Patent Application No. 97937813.0, 2005.
Declaration of Assistant Professor Ann Campbell Lawrie submitted in opposition to European Patent Application No. 97937813.0, 2005.
Declaration of Mr. William R. Egbert submitted in opposition to European Patent Application No. 97937813.0, 2005.
Notice of Opposition against EP 0957137 by Martek Biosciences Corporation, 2005.
Patent Publication Number: 20060189588
Inventors: Kenichi Higashiyama (Mishima-gun), Kengo Akimoto (Mishima-gun), Sakayu Shimizu (Kyoto)
Application Number: 11/407,984
Current U.S. Class: Fat; Fatty Oil; Ester-type Wax; Higher Fatty Acid (i.e., Having At Least Seven Carbon Atoms In An Unbroken Chain Bound To A Carboxyl Group); Oxidized Oil Or Fat (435/134); Carbon To Carbon Unsaturation (514/560); Zc(=o)oy, Wherein Z Is An Acyclic Radical Bonded To The C=o By A Carbon And Y Is An Organic Radical Bonded To The Oxygen By A Carbon (514/546); Fatty Compounds Having An Acid Moiety Which Contains The Carbonyl Of A Carboxylic Acid, Salt, Ester, Or Amide Group Bonded Directly To One End Of An Acyclic Chain Of At Least Seven (7) Uninterrupted Carbons, Wherein Any Additional Carbonyl In The Acid Moiety Is (1) Part Of An Aldehyde Or Ketone Group, (2) Bonded Directly To A Noncarbon Atom Which Is Between The Additional Carbonyl And The Chain, Or (3) Attached Indirectly To The Chain Via Ionic Bonding (554/1); Pediatric (426/801); Poultry Or Ruminant Feed (426/807)
International Classification: C12P 7/64 (20060101); A61K 31/20 (20060101); C07C 53/00 (20060101); A23L 1/30 (20060101); A23D 9/00 (20060101); A23K 1/16 (20060101); A23L 1/29 (20060101);