[go: up one dir, main page]

WO2007071800A1 - Procede microbien de production d'isomeres specifiques d'acides linoleiques conjugues - Google Patents

Procede microbien de production d'isomeres specifiques d'acides linoleiques conjugues Download PDF

Info

Publication number
WO2007071800A1
WO2007071800A1 PCT/ES2006/000638 ES2006000638W WO2007071800A1 WO 2007071800 A1 WO2007071800 A1 WO 2007071800A1 ES 2006000638 W ES2006000638 W ES 2006000638W WO 2007071800 A1 WO2007071800 A1 WO 2007071800A1
Authority
WO
WIPO (PCT)
Prior art keywords
conjugated linoleic
trans
isomer
production
cect
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/ES2006/000638
Other languages
English (en)
Spanish (es)
Inventor
Salvator Genoves Martinez
David Barreras Martinez
Marta Tortajada Serra
Daniel RAMÓN VIDAL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratorio Reig Jofre SA
Original Assignee
Natraceutical SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Natraceutical SA filed Critical Natraceutical SA
Publication of WO2007071800A1 publication Critical patent/WO2007071800A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
    • C12P7/6431—Linoleic acids [18:2[n-6]]
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D13/00—Finished or partly finished bakery products
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D13/00—Finished or partly finished bakery products
    • A21D13/06—Products with modified nutritive value, e.g. with modified starch content
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/123—Fermented milk preparations; Treatment using microorganisms or enzymes using only microorganisms of the genus lactobacteriaceae; Yoghurt
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats

Definitions

  • This invention relates to a method of producing conjugated linoleic acids, particularly the cis-9, trans-11 isomer, using microorganisms.
  • the use of said acids can be applied to the bio-feed and biotechnology sector.
  • conjugated linoleic acids abbreviated CLAs for the acronym of conjugated linoleic acids
  • PUFAs polyunsaturated fatty acids
  • CLAs have been shown to be able to act as preventive and therapeutic agents in many tumor models in experimental animals (Margot M e ⁇ al. (2003). J. Mammary Gland Biol. Neoplas. 8: 103-118) .
  • the inhibition by CLAs of the induction of breast carcinogenesis has been demonstrated (Ip C e ⁇ al. (1991). Cancer Res. 51 .: 6118-6124; Ip e ⁇ al. (1997).
  • CLAs CLAs
  • Other properties of CLAs refer to their ability to inhibit atherogenesis in hamsters and rabbits (from Deckere EA ef al. (1999). Br. J. Nutr. 82: 309-317; Lee KN e ⁇ al. (1994). Atherosclerosis 108: 19-25; Kritchevsky D ef al. (2000). J. Am. CoII. Nutr. 19: 472S-477S; and Wilson TA ef al. (2000). Nutr. Res. 20: 1795-1805, 32-34) and also, in pre-diabetic rats, their ability to increase insulin sensitivity and improve glucose tolerance (Houseknecht KL ⁇ t al. (1998). Biochem. Biophys. Res. Commun.
  • the natural biological source of linoleic acid is vegetable oils.
  • the natural biological source of CLAs is dairy products and ruminant meat. In fact, in the latter case it is a rumen bacterium that produces the CLAs and fixes them on the animal's tissue.
  • a combination of CLAs is commercialized for the food industry (an isomolar mixture of the two isomers with 80% purity) and the pure isomers are also sold although their price is very high, probably due to the difficulty of purification of both isomers.
  • the present invention describes the tests of five strains of bacteria, seven strains of yeasts Saccharomyces cer ⁇ visiae, seven strains of yeasts different from Saccharomyces and two species of fungi, to evaluate their production capacity of the cis-9 isomer, trans-11 of conjugated linoleic acid, both in the presence and absence of vaccenic acid.
  • the results are a new procedure for obtaining cis-9, trans-11 acid from conjugated linoleic acid.
  • the present invention describes several processes for the specific production of the cis-9-trans-11 isomer of conjugated linoleic acid.
  • the first of these describes the incorporation of the trans-11 isomer of vaccenic acid as a substrate to culture media where a bacterium, a yeast or a filamentous fungus grows and the microbial bioconversion of said substrate in the isomer of interest measured by the generation of a new configuration link Z (cis) in position 9 of the chain.
  • the second deals with the endogenous production by some microorganisms of the cis9-trans11 isomer without precursors in the culture medium.
  • the constitutive production of the trans-11 isomer of vaccenic acid by some yeasts is described.
  • the present invention is based on several facts related to the microbial metabolism of fatty acids.
  • the addition as a substrate of the trans-11 isomer of vaccenic acid to different microorganisms allows the production of a polyunsaturated fatty acid (the cis-9-trans-11 isomer of conjugated linoleic acid) with an additional unsaturation of configuration Z (cis) in position 9 of the chain of said substrate caused by the action of the enzyme ⁇ 9 -desaturase present in all microorganisms tested.
  • certain microorganisms are capable of producing said isomer without the need for any precursor substrate by containing fatty acids (vaccenic acid, oleic acid or others) in their cytoplasm and / or cell membranes that can act as substrates for the aforementioned enzymatic activities. In this sense, the production has been verified constitutive of the trans-11 isomer of vaccenic acid by some microorganisms.
  • the induction medium 5 ⁇ l of a 0.5 M ethanolic solution of the trans-11 isomer of the vaccenic acid was added to 5 ml of liquid medium, using the same means used to obtain colonies or mycelium but without agar and with the addition of 1% v / v tergitol.
  • the trans-11 isomer of vaccenic acid was at a final concentration of 0.5 mM.
  • the mixture was inoculated with a colony isolated from the microorganism in question and incubated for 48 hours at the corresponding temperature in each case and with a stirring of 200 rpm, with the exception of the Leuconostoc citreum strain that was incubated without stirring.
  • the culture was transferred to a 10 ml tube and centrifuged at 4000 rpm for 5 minutes. The supernatant was removed and the cells were resuspended in 1.5 ml of distilled water and the suspension was transferred to a 2 ml eppendorf vial. The culture was centrifuged under the same conditions, repeating again the washing operation with the same volume of distilled water. Finally it was centrifuged at 5000 rpm for 5 minutes to completely eliminate the water. 1 ml of CHCI 3 : MeOH (2: 1) was added to the obtained cells and the mixture was left in incubation for 1 hour. Finally, it was centrifuged at 13200 rpm for 15 seconds and the organic extract was transferred to a new 2 ml vial where the solvent was evaporated.
  • the fatty acid residue is methyl by adding 500 ⁇ l of a 0.5N solution of KOH in MeOH, followed by neutralization after 30 minutes with 500 ⁇ l of 1 N HCI and extraction with 500 ⁇ l of hexane. The organic layer was separated and concentrated to an approximate volume of 20 ⁇ l.
  • the cis-9-trans-11 isomer of the conjugated linoleic acid was then analyzed.
  • the methyl ester was analyzed by gas chromatography-mass spectrometry (GC-MS) in a apolar column HP-VOC (0.2mm * 30m * 1.12 ⁇ m) with the following temperature program: 80 0 C (0 min.); 2.5 ° C / min up to 220 0 C (0 min.); 2.0 ° C / min up to 260 0 C (15 min.).
  • Pregrowth for generating colonies isolated from bacteria of the species Lactobacillus pentosus and Leuconostoc citreum was performed on MRS agar plates by inoculating a groove-Agar and incubation at 30 0 C for 48 hours.
  • Colonies of Bacillus species subtilis and the Escherichia coli precrecieron in agar plates Agar MC-incubating at 3O 0 C and 37 0 C respectively for 24 hours.
  • the colonies of the species Zymomonas mobilis were grown in YPD-Agar solid medium incubating at 3O 0 C for 48 hours.
  • the culture was transferred to a 10 ml tube and centrifuged at 4000 rpm for 5 minutes. The supernatant was removed and the cells were resuspended in 1.5 ml of distilled water and the suspension was transferred to a 2 ml eppendorf vial. The culture was centrifuged under the same conditions, repeating again the washing operation with the same volume of distilled water. Finally it was centrifuged at 5000 rpm for 5 minutes to completely eliminate the water. 1 ml of CHCI 3 : MeOH (2: 1) was added to the obtained cells and the mixture was left in incubation for 1 hour.
  • the fatty acid residue is methyl by adding 500 ⁇ l of a 0.5N solution of KOH in MeOH, followed by neutralization after 30 minutes with 500 ⁇ l of 1N HCI and extraction with 500 ⁇ l of hexane. The organic layer was separated and concentrated to an approximate volume of 20 ⁇ l.
  • the cis-9-trans-11 isomer of the conjugated linoleic acid was then analyzed.
  • the methyl ester was analyzed by gas chromatography-mass spectrometry (GC-MS) in a apolar column HP-VOC (0.2mm * 30m * 1.12 ⁇ m) with the following temperature program: 80 0 C (0 min.); 2.5 ° C / min up to 22O 0 C (0 min.);
  • yeasts S. cerevisiae CECT 1176 and anomalous Pichia CECT 10590 were used. The pre-growth of the yeasts was carried out in YPD-agar medium plates inoculating a stretch mark of the microbial suspension and incubating at 3 ° C for 48 hours. A colony isolated from the microorganism in question was inoculated in 5 ml of YPD liquid medium with 1% tergitol (v / v). The mixture was incubated for 48 hours at the corresponding temperature for each microorganism with a stirring of 200 rpm.
  • the culture was transferred to a 10 ml tube and centrifuged at 4000 rpm for 5 minutes. The supernatant was removed and the cells were resuspended in 1.5 ml of distilled water and the suspension was transferred to a 2 ml eppendorf vial. The culture was centrifuged under the same conditions, repeating again the washing operation with the same volume of distilled water. Finally it was centrifuged at 5000 rpm for 5 minutes to completely eliminate the water. 1 ml of CHCI 3 : MeOH (2: 1) was added to the obtained cells and the mixture was left in incubation for 1 hour. Finally, it was centrifuged at 13200 rpm for 15 seconds and the organic extract was transferred to a new 2 ml vial where the solvent was evaporated.
  • the fatty acid residue is methyl by adding 500 ⁇ l of a 0.5N solution of KOH in MeOH, followed by neutralization after 30 minutes with 500 ⁇ l of 1N HCI and extraction with 500 ⁇ l of hexane. The organic layer was separated and concentrated to an approximate volume of 20 ⁇ l.
  • the trans-11 isomer of vaccenic acid was then analyzed.
  • the methyl ester was analyzed by gas chromatography-mass spectrometry (GC-MS) on an HP-VOC apolar column (0.2mm * 30m * 1.12 ⁇ m) with the following temperature program: 8O 0 C (0 min.); 2.5 ° C / min up to 22O 0 C (0 min.); 2.0 ° C / min up to 26O 0 C
  • Table 4 shows the results obtained.
  • the yeast S. cerevisiae CECT 1176 produces a residual amount of the trans-11 isomeric isomer of vaccenic acid.
  • the anomalous P. yeast CECT 10590 produces approximately 0.5 mM of said compound, defining culture conditions for the production of this compound with possible activity as a functional ingredient.
  • these results suggest that the production of the 9-cis, 11-trans-isomer of linoleic acids conjugated by the microorganisms of Table 1 is due to the fact that said microorganisms are to a greater or lesser extent producing 11-trans-acid. vaccenic
  • Saccharomyces cerevisiae CECT 1176 Laboratory strain Saccharomyces cerevisiae CECT 1326 Yeast for bread production Saccharomyces cerevisiae CECT 1479 Yeast for wine production Saccharomyces cerevisiae CECT 1894 Yeast for wine production Saccharomyces cerevisiae CECT 1929 Yeast for cider production Saccharomyces cerevisiae CECT 1929 Saccharomyces cerevisiae CECT 12660 Yeast for cava production
  • Saccharomyces cerevisiae CECT 1176 0.1799 Saccharomyces cerevisiae CECT 1326 0,1493 Saccharomyces cerevisiae CECT 1479 0,0401 Saccharomyces cerevisiae CECT 1894 0,1962 Saccharomyces cerevisiae CECT 1929 0,1582 Saccharomyces cerevisiae CECT 10029 0,0587 Saccharomyces cerevisiae CECT 10094 0,0257 Cerecharome CECT 10094 0,0257 cerebriae CECT 10094 0,0257 cerebriae CECT 10094 0,0257 cerebriae CECT 10094 0,0257 Cerecharomia
  • Saccharomyces cerevisiae CECT 1176 0.0131 Saccharomyces cerevisiae CECT 1326 0.0209 Saccharomyces cerevisiae CECT 1479 0.0156 Saccharomyces cerevisiae CECT 1894 0.0052 Saccharomyces cerevisiae CECT 1929 0.0056 Saccharomyces cerevisiae CECT 10094 0.0060 Saccharomyces CECT 10094 0.0060 Saccharomyces CECT 10094 0.0060 Saccharomyces CECT 10094 0.0060 Saccharomyces CECT 10094 0.0060
  • the levaduriform biomass enriched in the cis-9-trans-11 isomer was collected by centrifugation, washed twice by resuspension in 50 mM sodium phosphate buffer pH 6.8 and subsequent centrifugation.
  • the resulting biomass pulp was characterized in terms of its content in the cis-9-trans-11 isomer of conjugated linoleic acid, determining a concentration of 0.16 mM.
  • yeasts bread was manufactured in a pilot oven following an established industrial protocol. The concentration of the cis-9-trans-11 isomer was evaluated on the breads produced.
  • the fatty acid residue is methyl by the addition of 50OjC /! of a 0.5N solution of KOH in MeOH, followed by neutralization after 30 minutes with 500 // I of 1N HCI and extraction with 500 // I of hexane.
  • the organic layer was separated and concentrated to an approximate volume of 20 // I.
  • the cis-9-trans-11 isomer of the conjugated linoleic acid was then analyzed.
  • the methyl ester was analyzed by gas chromatography-mass spectrometry (GC-MS) on an HP-VOC apolar column (0.2mm * 30m * 1.12 ⁇ m) with the following temperature program: 8O 0 C (0 min.); 2.5 ° C / min up to 22O 0 C (0 min.);
  • a specific value within the concentration range of the c9-t11 isomer obtained was 0.35 ⁇ g / gram of bread.
  • This phase was dried and subsequently resuspended in 500 // I of a 0.5N solution of KOH in methanol for 30 minutes to methylate the extracted fatty acids and obtain their methyl esters.
  • the solution was then neutralized with 500 ⁇ l of 1N HCI and finally the fatty acid methyl esters were extracted with 500 // I hexane. Finally, they were concentrated to an approximate volume of 20 // I and the methyl esters were analyzed by gas chromatography.
  • Yogurt c9-t11 15,096 ⁇ 1,030 Industrial productions of cured sausages have also been carried out using fermentation initiators (lactic acid bacteria) loaded with the cis-9-trans-11 isomer of conjugated linoleic acid by pre-growth in media with the trans-11 isomer of vaccenic acid.
  • fermentation initiators lactic acid bacteria

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention concerne un procédé microbien de production d'isomères spécifiques d'acides linoléiques conjugués, notamment l'isomère classe-9, trans-11, faisant intervenir des micro-organismes. Le procédé implique l'incorporation facultative de l'isomère trans-11 de l'acide vaccénique servant de substrat à un milieu de culture où les micro-organismes tels que les bactéries, les levures ou les champignons produisent la bioconversion vers l'isomère d'intérêt par génération d'une nouvelle liaison de configuration Z (cis) en position 9 de la chaîne. L'utilisation de ces acides linoléiques conjugués trouve une application dans les secteurs de l'alimentation biologique et de la biotechnologie.
PCT/ES2006/000638 2005-11-21 2006-11-17 Procede microbien de production d'isomeres specifiques d'acides linoleiques conjugues Ceased WO2007071800A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP200502849 2005-11-21
ES200502849A ES2277546B1 (es) 2005-11-21 2005-11-21 Procedimiento microbiano de produccion de isomeros especificos de acidos linoleicos conjugados.

Publications (1)

Publication Number Publication Date
WO2007071800A1 true WO2007071800A1 (fr) 2007-06-28

Family

ID=38188295

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/ES2006/000638 Ceased WO2007071800A1 (fr) 2005-11-21 2006-11-17 Procede microbien de production d'isomeres specifiques d'acides linoleiques conjugues

Country Status (2)

Country Link
ES (1) ES2277546B1 (fr)
WO (1) WO2007071800A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7662979B2 (en) 2006-05-25 2010-02-16 Wyeth Oxindoledioxans, synthesis thereof, and intermediates thereto

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997037546A1 (fr) * 1996-04-11 1997-10-16 Loders Croklaan B.V. Compositions coulantes a base de graisses
WO1999029886A1 (fr) * 1997-12-05 1999-06-17 Bjoerck Lennart Formation d'acides gras non satures et conjugues
WO2001036653A1 (fr) * 1999-11-19 2001-05-25 Valio Ltd Procede de preparation d'acide linoleique conjugue
WO2003080850A1 (fr) * 2002-03-27 2003-10-02 Valio Ltd Procede de preparation d'acide linoleique conjugue
ES2204328A1 (es) * 2002-10-04 2004-04-16 Consejo Sup. De Invest. Cientificas Procedimiento de produccion de acidos grasos polinsaturados con levaduras por incorporacion de sustratos olefinicos o acetilenicos.
EP1500706A1 (fr) * 2002-04-12 2005-01-26 Kabushiki Kaisha Yakult Honsha Procede de production d'acide gras conjugue et aliment /boisson obtenus grace a ce procede

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997037546A1 (fr) * 1996-04-11 1997-10-16 Loders Croklaan B.V. Compositions coulantes a base de graisses
WO1999029886A1 (fr) * 1997-12-05 1999-06-17 Bjoerck Lennart Formation d'acides gras non satures et conjugues
WO2001036653A1 (fr) * 1999-11-19 2001-05-25 Valio Ltd Procede de preparation d'acide linoleique conjugue
WO2003080850A1 (fr) * 2002-03-27 2003-10-02 Valio Ltd Procede de preparation d'acide linoleique conjugue
EP1500706A1 (fr) * 2002-04-12 2005-01-26 Kabushiki Kaisha Yakult Honsha Procede de production d'acide gras conjugue et aliment /boisson obtenus grace a ce procede
ES2204328A1 (es) * 2002-10-04 2004-04-16 Consejo Sup. De Invest. Cientificas Procedimiento de produccion de acidos grasos polinsaturados con levaduras por incorporacion de sustratos olefinicos o acetilenicos.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7662979B2 (en) 2006-05-25 2010-02-16 Wyeth Oxindoledioxans, synthesis thereof, and intermediates thereto

Also Published As

Publication number Publication date
ES2277546A1 (es) 2007-07-01
ES2277546B1 (es) 2008-06-16

Similar Documents

Publication Publication Date Title
Wada et al. Temperature-induced changes in the fatty acid composition of the cyanobacterium, Synechocystis PCC6803
EP3385371B1 (fr) Utilisation d'un composé antioxydant pour la culture de bactéries anaerobies
James et al. Fatty acid metabolism by cutaneous bacteria and its role in axillary malodour
Wang et al. Heterotrophic cultivation of Chlorella pyrenoidosa using sucrose as the sole carbon source by co-culture with Rhodotorula glutinis
Vadivelan et al. Production and Enhancement of Omega‐3 Fatty Acid from Mortierella alpina CFR‐GV15: Its Food and Therapeutic Application
US5856149A (en) Method of producing conjugated fatty acids
Maneerat et al. Bile acids are new products of a marine bacterium, Myroides sp. strain SM1
US12203121B2 (en) Protists enriched with lipids rich in polyunsaturated fatty acids
CN102137922B (zh) 从硒代羟酸化合物开始富集了硒的光合微生物，其在营养学、美容学和药学中的应用
Jo et al. γ-Dodecelactone production from safflower oil via 10-hydroxy-12 (Z)-octadecenoic acid intermediate by whole cells of Candida boidinii and Stenotrophomonas nitritireducens
Liang et al. Identification and quantitation of hydroxy fatty acids in fermented sausage samples
Fiorino et al. Triacylglycerols hydrolysis and hydroxy-and epoxy-fatty acids release during lactic fermentation of plant matrices: An extensive study showing inter-and intra-species capabilities of lactic acid bacteria
Barsanti et al. Fatty acid content in wild type and WZSL mutant of Euglena gracilis
Hao et al. Fatty acid secretion by the white-rot fungus, Trametes versicolor
Gurovic et al. Lactic acid bacteria isolated from fish gut produce conjugated linoleic acid without the addition of exogenous substrate
Čertík et al. Effect of selenium on lipid alternations in pigment-forming yeasts
Alasmary et al. Evaluation of the chemical constituents and potential biological activities of Cunninghamella blakesleeana
He et al. Enhancement of intracellular accumulation of copper by biogenesis of lipid droplets in Saccharomyces cerevisiae revealed by transcriptomic analysis
Khaskheli et al. A highly selective whole cell biocatalysis method for the production of two major bioactive conjugated linoleic acid isomers
FI115842B (fi) Menetelmä konjugoidun linolihapon valmistamiseksi
Ruiz et al. Lipid content and fatty acid composition of a marine-derived Trichoderma longibrachiatum strain cultured by agar surface and submerged fermentations
ES2277546B1 (es) Procedimiento microbiano de produccion de isomeros especificos de acidos linoleicos conjugados.
Dedyukhina et al. Biosynthesis of arachidonic acid by micromycetes
Vahvaselkä et al. Enrichment of conjugated linoleic acid in oats (Avena sativa L.) by microbial isomerization
KR100417390B1 (ko) 신규 미생물 비피도박테리움 브레베 ｌｍｃ7 비피더스균주, 동 균주를 이용한 공액이중결합 지방산의 생산방법및 동 균주를 이용한 발효유의 제조방법

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06847053

Country of ref document: EP

Kind code of ref document: A1