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WO2004020647A1 - Procede de production et de recuperation de lipides de mannosylerythritol a partir du milieu de culture les contenant - Google Patents

Procede de production et de recuperation de lipides de mannosylerythritol a partir du milieu de culture les contenant Download PDF

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Publication number
WO2004020647A1
WO2004020647A1 PCT/EP2003/008929 EP0308929W WO2004020647A1 WO 2004020647 A1 WO2004020647 A1 WO 2004020647A1 EP 0308929 W EP0308929 W EP 0308929W WO 2004020647 A1 WO2004020647 A1 WO 2004020647A1
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Prior art keywords
mannosylerythritol lipids
oil
lipids
fermentation
mannosylerythritol
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English (en)
Inventor
Udo Rau
Siegmund Lang
La Anh Nguyen
Harald Wilhelm Walter RÖPER
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Cerestar Holding BV
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Cerestar Holding BV
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Priority to AU2003260404A priority Critical patent/AU2003260404A1/en
Publication of WO2004020647A1 publication Critical patent/WO2004020647A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/60—Salad dressings; Mayonnaise; Ketchup
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • 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
    • C12P7/62—Carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi

Definitions

  • the present invention relates to a fermentative process for producing mannosylerythritol lipids, and recovering mannosylerythritol lipids by heat treatment and extraction with alcohol-like solvent.
  • Microbial surfactants have unique characteristics (i.e. mild production conditions, biodegradability, wide range of biological activities) in comparison with their chemical counterparts. They may be applied at extreme temperatures, acidity, and salt concentrations. Due to these advantages they can be used not only as ingredients in food, cosmetics and pharmaceutics, but also in environmental and energy-saving technology (Banat et al., Appl. Microbiol. Biotech., 2000, 53, page 495-508).
  • Mannosylerythritol lipids are examples of such microbial surfactants. Like a typical natural product, mannosylerythritol lipids do not possess a single defined structure but consist of similar compounds depending on the producing microorganism and the substrate used.
  • DE 198 02 450 describes a process and an application for ustilipids. These are mannosylerythritol lipids produced by micro-organisms of the genus Ustilago. In particular, a fermentation process in presence of a deposited strain Ustilago maydis DSM 11494 is described. The product is isolated by applying solvent extraction or chromatography. The crude extract contained 5.3 g/L ustilipids. After purification the yield reduced to 0.8 g L. In Agric. Biol. Chem (1990, 54(1), page 31-36) D. Kitamoto describes the accumulation of mannosylerythritol lipids by a Candida antarctica strain.
  • Kitamoto describes mannosylerythritol lipids production by different strains of Candida antarctica. Under the optimal conditions in a shake culture, the concentration of the total lipids amounted to about 40 g/L after 8 days, corresponding to a productivity of 5 g/Ld. The same yield and productivity was also reported by Kim et al. (Biotechnol. Letters, 2002, 24, pages 225- 229) but they used Candida antarctica (SY16) as production strain with oleic acid and glycerol as substrates. Kitamoto et al.
  • the current invention provides such a process.
  • the present invention discloses a fermentative process for producing and recovering mannosylerythritol lipids, said process comprising the following steps: a) Preparing a pre-culture containing a carbon source and nitrogen source for a micro-organism of the species Pseudozyma aphidis, b) preparing a fermentation culture medium comprising a nitrogen source and a fatty oil, c) adding the micro-organisms containing pre-culture to the fermentation culture medium, d) allowing the micro-organisms to grow until at least 45 g/L mannosylerythritol lipids are obtained in the fermentation medium, e) recovering of mannosylerythritol lipids.
  • the current invention relates to a process wherein the fermentation culture medium is prepared -from a nitrogen source based on nitrate and the fatty oil is selected from the group consisting of soybean oil, sunflower oil, rapeseed oil, coconut oil, palm or palm kernel oil, canola oil, corn oil, cottonseed oil, olive oil, peanut oil, rice bran oil, safflower oil, sesame oil, almond kernel oil or any other oil suitable for use in cosmetic or food products, and mixtures of two or more thereof.
  • the fatty oil is selected from the group consisting of soybean oil, sunflower oil, rapeseed oil, coconut oil, palm or palm kernel oil, canola oil, corn oil, cottonseed oil, olive oil, peanut oil, rice bran oil, safflower oil, sesame oil, almond kernel oil or any other oil suitable for use in cosmetic or food products, and mixtures of two or more thereof.
  • the current invention relates to a process wherein productivity of step d) of said process is higher than 8 g/Ld.
  • the current invention further relates to a process wherein recovering mannosylerythritol lipids from fermentation medium comprises the following steps: a) heating the fermentation medium to disintegrate the emulsified fermentation medium, b) cooling to obtain phase separation into liquid and solid phase, c) treating the solid phase with alcohol-like solvent to obtain dissolution of mannosylerythritol lipids, d) collecting mannosylerythritol lipids from the alcohol-like solution, e) optionally treating the liquid phase of step b) with alcohol-like solvent to obtain mannosylerythritol lipids, and f) optionally combining collected mannosylerythritol lipids of step d) and e).
  • the current invention discloses a process wherein the fermentation medium is heated to a temperature above 100°C, preferably 105°C - 120°C and the alcohol-like solvent is ethanol.
  • the current invention relates to a process wherein the recovery yield of mannosylerythritol lipids is higher than 85%, preferably higher than 90%.
  • the current invention relates to a fermentative process comprising the following steps: a) Preparing a pre-culture containing a nitrate as nitrogen source and glucose as carbon source for the micro-organism Pseudozyma aphidis deposited on 16/04/2002 under number DSM 14930, b) preparing a fermentation culture medium comprising a glucose, nitrate and a fatty oil, c) adding the micro-organisms containing pre-culture to the fermentation culture medium, d) allowing the micro-organisms to grow until at least 70 g/L mannosylerythritol lipids are obtained in the fermentation medium, e) heating the fermentation medium to a temperature above 100°C to disintegrate the emulsified fermentation medium, f) cooling to obtain phase separation into liquid and solid phase, g) treating the solid phase with ethanol to obtain dissolution of mannosylerythritol lipids, h) collecting mannosylerythr
  • the current invention relates to a process wherein in step d) the productivity is at least 10 g/Ld.
  • the current invention discloses a Pseudozyma aphidis strain characterised in that it produces more than 70 g/L mannosylerythritol lipids.
  • the current invention relates to a process wherein in step d) at least 120 g/L mannosylerythritol lipids with a productivity of more than 12 g/Ld are obtained.
  • the current invention further discloses a Pseudozyma aphidis strain deposited under the Budapest Treaty at DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen by Technische Universitat Braunschweig on 16/04/2002 under number DSM 14930.
  • the current invention relates to the use of mannosylerythritol lipids in cosmetics for skin care and in food products.
  • Figure 1 is a microscope (Nikon Optiphot; amplification: 1500) picture of Pseudozyma aphidis DSM 14930 grown on glucose and said picture is taken with a microscope. It is shown that the cells contain prominent highly refractive globules, which were even much more abundant if soybean oil was used as carbon source.
  • the present invention discloses a fermentative process for producing and recovering mannosylerythritol lipids, said process comprising the following steps: 2004/020647
  • the pre-culture can be prepared from glucose as carbon source and ammonium nitrate as nitrogen source.
  • the pre-culture is prepared from 20 to 30 g/L glucose and 0.2 - 1.8 g/L ammonium nitrate.
  • the preculture can be enriched with 0.1 to 0.9 g/L potassium dihydrogen phosphate, 0.1 to 0.9 g/L magnesium sulphate and 0.5 to 3.0 g/L yeast extract.
  • the pre-cultivation can be performed in 2 L shake flasks filled with 500 ml medium at 30°C and at 100 rpm on a rotary shaker.
  • the current invention relates to a process wherein the fermentation culture medium is prepared from a nitrogen source based on nitrate.
  • the fatty oil can be any fatty oil and preferably is selected from the group consisting of soybean oil, sunflower oil, rapeseed oil, coconut oil, palm or palm kernel oil, canola oil, corn oil, cottonseed oil, olive oil, peanut oil, rice bran oil, safflower oil, sesame oil, almond kernel oil or any other oil suitable for use in cosmetic or food preparations, and mixtures of two or more thereof.
  • At least 45 g/L mannosylerythritol lipids with a productivity higher than 8 g/Ld is obtainable by applying a fermentation culture medium which is containing sodium nitrate.
  • the fermentation can be performed in a bioreactor.
  • Conductivity sensors can be used for the controlled addition of fatty oils as foam inhibitors.
  • the controlled addition of these compounds, which also act as substrates, enables the microorganism to enhance the yield and productivity.
  • High yields of mannosylerythritol lipids are obtainable by applying soybean oil as fatty oil and sodium nitrate as nitrogen source.
  • the current invention further relates to a process wherein recovering mannosylerythritol lipids from fermentation medium comprises the following steps: a) heating the fermentation medium to disintegrate the emulsified fermentation medium, b) cooling to obtain phase separation into liquid and solid phase, c) treating the solid phase with alcohol-like solvent to obtain dissolution of mannosylerythritol lipids, d) collecting mannosylerythritol lipids from the alcohol-like solution, e) optionally treating the liquid phase of step b) with alcohol-like solvent to obtain mannosylerythritol lipids, and f) optionally combining collected mannosylerythritol lipids of step d) and e).
  • Mannosylerythritol lipids are surfactant-like or emulsifying products. By virtue of the nature of these products it is very difficult to separate and recover these products in high yields and high purity.
  • the current invention discloses a recovery process wherein the emulsified fermentation medium is disintegrated by a heating step.
  • the current invention discloses a process wherein the fermentation medium is heated to a temperature above 100°C, preferably 105°C - 120°C.
  • the fermentation medium is heated to a temperature above 100°C, preferably 110°C during 10 minutes.
  • phase separation occurs into a liquid phase containing the cell debris and a solid sticky phase comprising mannosylerythritol lipids.
  • An alcohol-like solvent such as methanol, ethanol, propanol and/or butanol can be applied to collect the mannosylerythritol lipids.
  • ethanol is added to the solid sticky phase and mannosylerythritol lipids can be collected from the alcohol-like solution by filtration.
  • the liquid phase containing the cell debris can likewise be 2004/020647
  • alcohol-like solvent preferably ethanol.
  • centrifugation can be applied.
  • the current invention relates to a process wherein the recovery yield of mannosylerythritol lipids is higher than 85%, preferably higher than 90%.
  • the mannosylerythritol lipids, thus recovered, have a purity of at least 90%.
  • the current invention relates to a fermentative process comprising the following steps: a) Preparing a pre-culture containing a nitrate as nitrogen source and glucose as carbon source for the micro-organism Pseudozyma aphidis deposited on 16/04/2002 under number DSM 14930, b) preparing a fermentation culture medium comprising glucose, a nitrate and a fatty oil, c) adding the micro-organisms containing pre-culture to the fermentation culture medium, d) allowing the micro-organisms to grow until at least 70 g/L mannosylerythritol lipids are obtained in the fermentation medium, e) heating the fermentation medium to a temperature above 100°C to disintegrate the emulsified fermentation medium, f) cooling to obtain phase separation into liquid and solid phase, g) treating the solid phase with ethanol to obtain dissolution of mannosylerythritol lipids, h) collecting mannosylerythr
  • the current invention relates to a process wherein in step d) the productivity is at least 10 g/Ld. In fact, it relates to a process wherein in step d) at least 120 g/L mannosylerythritol lipids with a productivity of more than 12 g Ld are obtained.
  • the feed solution can contain high concentrations of substrates such as glucose at 200-400 g/L, a nitrate, preferably sodium nitrate, at 10-30 g/L, and yeast extract at a concentration of 10-30 g/L.
  • substrates such as glucose at 200-400 g/L, a nitrate, preferably sodium nitrate, at 10-30 g/L, and yeast extract at a concentration of 10-30 g/L.
  • the strain Pseudozyma aphidis is synonym to Sterigmatos aphidis which was described in detail by Henninger and Windisch (Arch. Microbiol., 1975, 105, page 49- 50).
  • the strain was isolated from the secretions of Aphididae on leaves of Solarium pseudocapsicum and is able to assimilate both inositol and potassium nitrate.
  • a broad range of carbon sources can be used by this fungi such as pentoses, hexoses, sugar alcohols, soluble starch, ethanol and organic acids. Urease reaction is positive. Staining with Dazionium Blue B salt is also positive.
  • the fungi is anamorph to Ustilaginales because the comparison of the 26S ribosomal DNA placed it in the same group with Ustilago maydis (Boekhout, J. Gen. Appl. Microbiol., 1995, 41, page 359- 366).
  • the current invention further discloses a Pseudozyma aphidis strain deposited under the Budapest Treaty at DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen by Technische Universitat Braunschweig on 16/04/2002 under number DSM 14930. Pseudozyma aphidis DSM 14930 was isolated from soil.
  • the current invention relates to the use of mannosylerythritol lipids in cosmetics for skin care.
  • Essential criteria for identifying products that are applicable as cosmetics for skin care are skin compatibility and protection, efficacy, sensory properties, no critical impurities and environmental compatibility.
  • Mannosylerythritol lipids fulfil these criteria.
  • the current invention further relates to the use of mannosylerythritol lipids (as an ingredient or additive) in food products and preparations.
  • mannosylerythritol lipids of the present invention can be used as non-toxic emulsifiers in salad dressings, mayonnaise, margarine and other fat-based products, and in dairy (e.g. ice-cream), confectionery (e.g. chocolate) and bakery products.
  • - downstream processing is comprising a simple heating step followed by cooling with simultaneous formation of a sticky solid phase enriched with mannosylerythritol lipids, 4/020647
  • mannosylerythritol lipids can be added for further purification, high recovery yields of mannosylerythritol lipids are obtainable by the current disclosed process, mannosylerythritol lipids are obtainable in high purity because nearly all of the triglycerides added and enzymatically released fatty acids are consumed at the end of the cultivation run.
  • 132 g Glucose H 2 O was dissolved in 1 L tap water.
  • the sugar solution was prepared in double concentration and had to be sterilized separately from the likewise double concentrated salt and yeast extract solution. After cooling down the two 1 L solutions were combined at a ratio of 1 : 1 under aseptic conditions in order to yield 500 ml medium filled in two shake flasks equipped with two baffles. The starting pH was 6.
  • the medium was inoculated with a few colonies of Pseudozyma aphidis DSM 70725, provided by the DSMZ Deutschen Stammsammlung fur Mikroorganismen und Stammkulturen, Braunschweig, and incubated for 3 days at 27°C and 100 rpm on a rotary shaker.
  • the 72 L bioreactor was equipped with two Rushton turbines of 14.5 cm diameter. The upper impeller was installed 5 cm below the medium surface.
  • the bioreactor was filled with 30 L tap water and the salts and yeast extract were added in appropriate concentrations.
  • the soybean oil was sterilized separately and added aseptically to the medium. The resulting pH of 6.2 was not adjusted throughout the cultivation.
  • the pre-culture, separately prepared, was added and fermentation was continued for 9 days. During the cultivation the stirrer speed and aeration rate were gradually reduced from 300 rpm to 250 rpm and 720 L/h to 108 L/h, respectively, in order to reduce foam formation and to manually control the pO 2 at approximately 60%.
  • Cell protein was chosen as equivalent for bio dry mass because the gravimetric determination of bio dry mass was erroneous due to the incorporation of storage compounds inside the cell which leads to an increase of biomass after N-limitation.
  • the mass ratio between cell protein and bio dry mass before N- limitation was approximately 1:5 so that a cell protein concentration of 2.5 g/L is roughly equivalent to a bio dry mass of 12.5 g L.
  • Cell protein was determined using the well known method of Lowry after solvent extraction of the biomass and subsequent alkaline cell disruption (Spoeckner et al., Appl. Microbiol. Biotechnol, 1999, 51, pages 33-39).
  • soybean oil After 2.6 days the addition of soybean oil was started at a rate of 0.35 ml/Lh and stopped after 7.7 days. After one day addition of soybean oil, the formation of MEL- beads indicated the enhanced product formation. Overall 123 ml/L soybean oil (80 ml/L initial, 43 ml/L added) was converted into maximum 74 g/L of mannosylerythritol lipids resulting in a yield coefficient of 0.65 (g/g) and a maximum productivity of 9.6 g/Ld.
  • the fermentation medium was heated to 110°C for 10 minutes followed by cooling to room temperature.
  • MEL mannosylerythritol lipids
  • the former heavier than water MEL-beads containing mannosylerythritol lipids and unconsumed fatty acids and triglycerides turned to a sticky solid phase enriched by MEL and depleted by fatty acids and triglycerides. Lower temperatures or a shorter processing time did not lead to a clear formation of the new sticky solid phase.
  • the residue was treated as follows: the aqueous phase containing cell debris was decanted and extracted by ethanol. Cell debris were separated by centrifugation. The solid sticky phase was dissolved in ethanol and cell debris were separated by filtration. Both mannosylerythritol lipids containing fractions were combined and ethanol was removed by vacuum evaporation. The residual highly viscous product was lyophilized and mannosylerythritol lipids were recovered at 88% recovery yield with a purity of 91%).
  • Mannosylerythritol lipids Purity of mannosylerythritol lipids was determined by HPLC analysis on a silica column with evaporative light scattering detector and applying a gradient solvent program of chloroform and methanol at a flow rate of 1 ml/min.
  • the preculture was prepared as described in Example 1, but the medium was inoculated with a few colonies of Pseudozyma aphidis deposited on 16/4/2002 under number DSM 14930.
  • the 72 L bioreactor was equipped with two Rushton turbines of 14.5 cm diameter. The upper impeller was installed 5 cm below the medium surface.
  • the bioreactor was filled with 30 L tap water and the salts, glucose and yeast extract were added in appropriate concentration.
  • the soybean oil was sterilized separately and added aseptically to the medium. Glucose was used as additional carbon source beside soybean oil. The resulting pH of 6.2 was not adjusted throughout the cultivation. The pre-culture, separately prepared, was added and fermentation was continued for 12 days.
  • nitrate was completely consumed and growth turned to the stationary phase.
  • a concentrated solution (3.1 L) of glucose (342 g/L), sodium nitrate (20 g/L) and yeast extract (14 g/L) was started at 1.75 days and at a rate of 2.2 ml/min.
  • the complete solution was fed after 2.8 days.
  • the addition of soybean oil for foam reduction was necessary between 0.75 and 3.75 days and in total 6.12 L soybean oil was added under controlled conditions. After 11.75 days, 165 g/L mannosylerythritol lipids were formed with a yield coefficient of 0.86 (w/w) and a productivity of 14.04 g/Ld.
  • Mannosylerythritol lipids were recovered as described in example 1.

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Abstract

La présente invention concerne un procédé qui permet de produire par fermentation des lipides de mannosylérythritol et de récupérer des lipides de mannosylérythritol avec un rendement considérable et une pureté élevée. Le procédé de récupération comprend une étape de chauffage et un traitement avec un solvant de type alcool. On peut obtenir un bon rendement de fermentation en utilisant une souche de Pseudozyma aphidis.
PCT/EP2003/008929 2002-08-24 2003-08-12 Procede de production et de recuperation de lipides de mannosylerythritol a partir du milieu de culture les contenant Ceased WO2004020647A1 (fr)

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Cited By (27)

* Cited by examiner, † Cited by third party
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JP2007252280A (ja) * 2006-03-23 2007-10-04 National Institute Of Advanced Industrial & Technology マンノシルエリスリトールリピッドの分離回収方法
EP2074985A3 (fr) * 2006-08-11 2010-01-13 Toyo Boseki Kabushiki Kasisha Activateur incluant un biosurfactant en tant qu'ingrédient actif, lipide de mannosyl érythritol et son procédé de fabrication
WO2011151819A3 (fr) * 2010-06-01 2012-03-29 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Pseudozyma aphidis en tant qu'agent de biocontrôle contre différents pathogènes de plantes
WO2013032189A3 (fr) * 2011-08-26 2013-06-13 (주)다미화학 Huile végétale fermentée et composition la comprenant
EP1964546A4 (fr) * 2005-11-25 2013-11-27 Toyo Boseki Produit cosmétique de soin de la peau et agent servant à empêcher la peau de devenir rêche contenant des biotensioactifs
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PT106959A (pt) * 2013-05-17 2014-11-17 Inst Superior Tecnico Processos para a produção de glicolípidos microbianos do tipo manosileritritolípidos, a partir de materiais lenhocelulósicos e suas aplicações
WO2017167914A1 (fr) 2016-03-31 2017-10-05 Oleon N.V. Procédé d'extraction de glycolipides et glycolipides obtenus
EP3290500A1 (fr) 2016-08-29 2018-03-07 Richli, Remo Composition de lavage, de nettoyage et de soin contenant de carboxylate polyoxyalkyléné
EP3290501A1 (fr) 2016-08-29 2018-03-07 Richli, Remo Compositions detergentes contentant des amides d'acides gras alcoxylés
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CN108619996A (zh) * 2018-04-26 2018-10-09 南京理工大学 一种甘露糖赤癣糖醇脂的分离纯化方法
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EP3955750A4 (fr) * 2019-04-16 2023-01-11 Locus IP Company, LLC Additifs alimentaires émulsifiants à base de microbes
CN115873729A (zh) * 2022-09-27 2023-03-31 中国海洋大学 产mel的蚜虫莫氏黑粉xad01工程菌株及其应用
US11759544B2 (en) 2018-05-25 2023-09-19 Locus Solutions Ipco, Llc Therapeutic compositions for enhanced healing of wounds and scars
WO2024019627A1 (fr) * 2022-07-19 2024-01-25 Instituto Superior Técnico Dispositif, système et procédé pour la production améliorée de lipides de mannosylérythritol (mel) intégrant la fermentation et la séparation de produits à partir d'un bouillon de fermentation selon des procédés non invasifs
US11963528B2 (en) 2018-02-26 2024-04-23 Locus Solutions Ipco, Llc Materials and methods for control of insect pests using entomopathogenic fungi
EP4361238A1 (fr) 2022-10-26 2024-05-01 ChemTEK UG (haftungsbeschränkt) Compositions comprenant des glycamines
US12187999B2 (en) 2017-12-28 2025-01-07 Locus Solutions Ipco, Llc Reactors and submerged fermentation methods for producing microbe-based products
WO2025051594A1 (fr) 2023-09-08 2025-03-13 Basf Se Utilisation de compositions contenant des tensioactifs non ioniques et compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61205450A (ja) * 1985-03-08 1986-09-11 Kao Corp 小麦粉製品の品質改良方法
US5273898A (en) * 1986-10-17 1993-12-28 Noro Nordisk A/S Thermally stable and positionally non-specific lipase isolated from Candida
WO2001096536A2 (fr) * 2000-06-13 2001-12-20 Novozymes A/S Proteases de l'acide aspartique et acides nucleiques codant pour elles
JP2002101847A (ja) * 2000-09-29 2002-04-09 Higashimaru Shoyu Co Ltd しょうゆ油の処理方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61205450A (ja) * 1985-03-08 1986-09-11 Kao Corp 小麦粉製品の品質改良方法
US5273898A (en) * 1986-10-17 1993-12-28 Noro Nordisk A/S Thermally stable and positionally non-specific lipase isolated from Candida
WO2001096536A2 (fr) * 2000-06-13 2001-12-20 Novozymes A/S Proteases de l'acide aspartique et acides nucleiques codant pour elles
JP2002101847A (ja) * 2000-09-29 2002-04-09 Higashimaru Shoyu Co Ltd しょうゆ油の処理方法

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ADAMCZAK MAREK ET AL: "Influence of medium composition and aeration on the synthesis of biosurfactants produced by Candida antarctica.", BIOTECHNOLOGY LETTERS, vol. 22, no. 4, February 2000 (2000-02-01), pages 313 - 316, XP008014840, ISSN: 0141-5492 *
DATABASE WPI Section Ch Week 198643, Derwent World Patents Index; Class D11, AN 1986-281674, XP002263708 *
DATABASE WPI Section Ch Week 200257, Derwent World Patents Index; Class D13, AN 2002-531592, XP002263703 *
HENNINGER W ET AL: "A NEW YEAST OF STERIGMATOMYCES-APHIDIS NEW-SPECIES", ARCHIVES OF MICROBIOLOGY, vol. 105, no. 1, 1975, pages 49 - 50, XP008025198, ISSN: 0302-8933 *
KIM H -S ET AL: "Characterization of a biosurfactant, mannosylerythritol lipid produced from Candida sp. SY16.", APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, vol. 52, no. 5, November 1999 (1999-11-01), pages 713 - 721, XP002234056, ISSN: 0175-7598 *
KITAMOTO D ET AL: "PRODUCTION OF MANNOSYLERYTHRITOL LIPIDS BY CANDIDA-ANTARCTICA FROM VEGETABLE OILS", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 54, no. 1, 1990, pages 37 - 40, XP002234057, ISSN: 0002-1369 *
KITAMOTO DAI ET AL: "Microbial conversion of n-alkanes into glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma (Candida antarctica).", BIOTECHNOLOGY LETTERS, vol. 23, no. 20, October 2001 (2001-10-01), pages 1709 - 1714, XP008014848, ISSN: 0141-5492 *

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