WO2017220298A1 - Emulsion grasse continue comestible contenant de la 1-désoxynojirimycine et de la lécithine - Google Patents

Emulsion grasse continue comestible contenant de la 1-désoxynojirimycine et de la lécithine Download PDF

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Publication number
WO2017220298A1
WO2017220298A1 PCT/EP2017/063093 EP2017063093W WO2017220298A1 WO 2017220298 A1 WO2017220298 A1 WO 2017220298A1 EP 2017063093 W EP2017063093 W EP 2017063093W WO 2017220298 A1 WO2017220298 A1 WO 2017220298A1
Authority
WO
WIPO (PCT)
Prior art keywords
emulsion
weight
lecithin
dnj
fat
Prior art date
Application number
PCT/EP2017/063093
Other languages
English (en)
Inventor
Gustaaf Servaas Marie Joseph Emile Duchateau
Frederik Michiel Meeuse
Original Assignee
Unilever N.V.
Unilever Plc
Unilever BCS Europe B.V.
Unilever Bcs Limited
Unilever Bcs Us Inc.
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 Unilever N.V., Unilever Plc, Unilever BCS Europe B.V., Unilever Bcs Limited, Unilever Bcs Us Inc. filed Critical Unilever N.V.
Publication of WO2017220298A1 publication Critical patent/WO2017220298A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, 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
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • 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
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • 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
    • A21D2/16—Fatty acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/013—Spread compositions

Definitions

  • the present invention relates to an edible fat- or oil-continuous emulsion, which edible emulsion comprises a continuous fat or oil phase, a dispersed water phase, the emulsion further comprising 1 -deoxynojirimycin (DNJ) and lecithin, wherein the lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and
  • DNJ 1 -deoxynojirimycin
  • lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and
  • phosphatidylethanolamine wherein the weight ratio (PC+PI)/PE in the emulsions is at least 2.5.
  • the invention further relates to a process for preparing such emulsion, as well as the use of such emulsion, wherein the emulsion is combined with edible matter comprising carbohydrates, in such an amount that the resulting foodstuff contains from 0.001 to 0.03 wt % of DNJ on carbohydrate basis.
  • the compound 1 -deoxynojirimycin (generally abbreviated as "DNJ") is a potent o glucosidase inhibitor, and as such may suppress postprandial blood glucose concentrations.
  • DNJ is present in e.g. various parts of the mulberry plant, such as leaves, bark and fruit.
  • teas containing mulberry are commercially supplied as functional foods in many countries. Such teas are (e.g. from a taste-perspective) not preferred by all consumers, and for efficacy would need to be consumed within a fairly short time frame of consuming carbohydrate-rich foods.
  • a DNJ-rich food can be provided that can contain and supply the right dose of DNJ to the person consuming such, and which food can easily be combined with carbohydrate-rich foods, such as e.g. bread or cookies.
  • Edible fat continuous emulsions are well known in the art and include for example spreads, margarines, and (ingredients for use in) confectionary products. Spreads are usually intended and used for spreading on bread (slices or rolls), whereas margarines often are considered the harder products sold e.g. in wrappers and which are e.g. used for making baked goods such as cookies and cakes. These fat-continuous emulsions like spreads and margarines could be a good carrier of DNJ (e.g. from an extract of mulberry such as mulberry fruit), as they are combined often with carbohydrate-rich foods. Spread is rarely consumed on its own, but generally used for spreading on bread, and margarines are e.g. used for baking cakes or cookies.
  • DNJ e.g. from an extract of mulberry such as mulberry fruit
  • these emulsions would be an excellent carrier for DNJ and DNJ-containing extracts of mulberry (leaf, bark, fruit) in terms of being consumed generally with carbohydrate-rich foods, and often the ratio emulsion : carbohydrate consumed is fairly predictable, and thus the DNJ content on the emulsion can be tailored fairly well so that an optimal ratio DNJ : carbohydrate is consumed.
  • the DNJ-containing food should also be able to release the DNJ in the stomach quickly, as it is believed that a slow release may render the DNJ not fully effective: the alpha-glucosidase inhibitory effect should be available in the stomach quickly after ingestion of the carbohydrate-rich food, i.e. in a similar time frame of the breakdown of starch to glucose.
  • fat-continuous emulsions such as spreads and margarines are not a very suitable vehicle for DNJ, and that rather DNJ is separately added just before consumption.
  • incorporation of DNJ e.g. in the form of an aqueous extract of white mulberry fruit
  • DNJ e.g. in the form of an aqueous extract of white mulberry fruit
  • an edible fat-continuous emulsion such as e.g. a spread or margarine, containing DNJ, in particular in the form of an (aqueous) extract of mulberry white fruit, which shows good release of the DNJ when such emulsion is spread on a slice of bread and such slice of bread with DNJ-containing spread is tested in a model of a stomach.
  • the release of the DNJ should be more close to what can be achieved when the DNJ (in the form of an aqueous mulberry fruit extract) is sprinkled on top of a slice of bread spread with the same emulsion without DNJ.
  • such DNJ-release should not only be good in a model stomach, but also in a human, but such is more difficult to measure than a model stomach.
  • an edible fat-continuous emulsion which emulsion comprises from 20 to 85% by weight of a continuous fat phase, from 15 to 80% by weight of a dispersed water phase, the amount of water and fat and oil together being at least 75% by weight, wherein the emulsion product further comprises from 0.001 to 0.08 % by weight of 1 - deoxynojirimycin (DNJ) and from 0.05 to 1 % by weight of lecithin, wherein the lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and
  • phosphatidylethanolamine wherein the weight ratio (PC+PI)/PE in the emulsion is at least 2.5.
  • the invention also relates to a process for preparing such emulsions, which process comprises the steps of preparing a aqueous phase containing the desired amount of 1- deoxynojirimycin, preparing an oil phase containing the desired amount of lecithin, wherein the lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and phosphatidylethanolamine (PE) wherein the weight ratio (PC+PI)/PE in the emulsion is at least 2.5, and mixing and emulsifying the aqueous phase and oil phase so that a fat- continuous emulsion is obtained.
  • PC phosphatidylcholine
  • PI phosphatidylinositol
  • PE phosphatidylethanolamine
  • the invention further relates to the use of the emulsion according to this invention, wherein the emulsion is combined with edible matter comprising carbohydrates, in such an amount that the resulting foodstuff contains from 0.001 to 0.03 % by weight of DNJ on carbohydrate basis.
  • the compound 1 -deoxynojirimycin is commonly abbreviated in literature as "DNJ".
  • the lUPAC name for it is: (2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol.
  • the compound is an alpha-glucosidase inhibitor, and is commonly found in parts of the mulberry plant (e.g. leaves, bark, fruit).
  • DNJ is herein to be understood as to comprise both DNJ and the edible salts thereof. The measurement method measures the sum of these.
  • Lecithin is herein to be understood as commercial lecithin as used by food
  • Lecithin can be obtained by water degumming the extracted oil of seeds. It is a mixture of various phospholipids and other components, and the composition depends on the origin of the lecithin. A major source of lecithin is soybean oil. Most relevant phospholipids found in lecithin include phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.
  • fat and oil are used interchangeably herein, and refer to edible triacylglycerides of fatty acids.
  • the person of average skill in the art will know that for such emulsion products to be spreadable (e.g. as a "spread") and in order to satisfy criteria such as health, mouthfeel and appearance, at least part of the continuous (lipid) phase (the fat and oil together) needs to be solid at room temperature. Still, for health reasons part of the continuous phase is preferably oil.
  • Weight percentages are herein to be understood as to be based on weight % based on the total emulsion, unless specified differently.
  • the emulsion according to the present invention it is preferred (e.g. for reasons of product properties) that the emulsion comprises from 35 to 80%, more preferably from 40 to 80%, by weight on the emulsion of a continuous fat phase.
  • the emulsions according to the present invention are preferably spreads or
  • the fat phase of such fat-continuous emulsions like spreads and margarines are preferably a mixture of liquid oil (i.e. fat that is liquid at ambient temperature) and fat which is solid at ambient temperatures.
  • the solid fat also called structuring fat or hardstock fat, serves to structure the fat phase and helps to stabilize the aqueous phase by forming a fat crystal network.
  • preferably 20 to 90 % by weight (more preferably 40 to 90%) of the continuous fat phase is oil, and 10 to 80% by weight (more preferably 10 to 60%) is preferably a hardstock fat.
  • a preferred oil in this connection is vegetable oil, such as sunflower oil, rapeseed oil, linseed oil, or soy bean oil.
  • the emulsion of the present invention preferably comprises from 0.002 to 0.05 % by weight, more preferably from 0.003 to 0.04 % by weight, of 1- deoxynojirimycin (DNJ), on the emulsion.
  • DNJ 1- deoxynojirimycin
  • the emulsion of the present invention preferably comprises from 0.08 to 0.6 % by weight of lecithin, more preferably from 0.1 to 0.4%. It was found by the present inventors that in terms of speed of release of DNJ in the stomach, as determined by the stomach model as used herein, not each and every lecithin behaves the same.
  • the proportions of the various phospholipids vary, e.g. depending on origin and method of production, isolation, and purification. It was found that for speedy release of the DNJ, yet not affecting properties like emulsion stability and mouthfeel not too negatively, it is required that the lecithin in the present emulsion comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and phosphatidylethanolamine (PE) wherein the weight ratio (PC+PI)/PE in the emulsion is at least 2.5. More preferably, for such reasons of efficacy and product properties, said weight ratio (PC+PI)/PE is at least 3.0.
  • PC phosphatidylcholine
  • PI phosphatidylinositol
  • PE phosphatidylethanolamine
  • the emulsions according to the present invention are preferably spreads or margarines, as such spreads can be used for spreading on bread, and thus
  • the spreads and margarines according to the present invention preferably will have a Stevens value of between 50 and 350.
  • the Stevens value of a W/O emulsion according to the invention is determined as follows. A product, whereof the Stevens-value is to be measured is stabilized at 5 degrees Celsius. The hardness of the product is measured with a Stevens
  • the emulsion according to the invention has a Stevens-value below 300, more preferably below 250, even more preferably below 220, most preferably below 200.
  • the Stevens value of the spreads according to the present invention have a Stevens value of from 80 to 250, more preferably from 90 to 220, even more preferably 100 to 200 and still even more preferably of from 120 to 200.
  • the values in this are measured after cycling.
  • the DNJ is preferably incorporated into the emulsion according to the invention as an extract of part of a plant of the Mulberry family (the Morus sp tree), more preferably an extract of the fruit of mulberry. Plants of the Mulberry family are known to contain DNJ. Even more preferably, the extracts as described above are obtained by aqueous extraction, which may be dried to provide a powder.
  • the emulsion according to the present invention comprises from 0.5 to 10% of extract of mulberry, preferably from mulberry fruit, more preferably from fruits from the white mulberry tree (Morus alba).
  • Mulberry fruit extract can be obtained from the fruit of the Morus sp tree.
  • Morus sp is widely cultivated in Asia, especially in China, where the leaves are used to feed silkworms employed in the commercial production of silk.
  • white mulberry varieties such as Morus alba L
  • other varieties such as Morus nigra L or Morus rubra L
  • the ripe mulberry fruits are widely used in juice, beverages, wine, jams, pies and tarts in many countries, such as China, Japan and India.
  • Dried mulberry fruit has been used as a traditional Chinese medicine for more than 2000 years, and its uses are shown in the Chinese Pharmacopeia.
  • Mulberry fruit is also mentioned in the Ayuverdic Materia Medica.
  • the emulsion according to the present invention preferably comprises 0.1-1.5% by weight of edible salt (i.e. NaCI and/or KCI).
  • the formulations according to the present invention may further comprise emulsifiers.
  • the emulsion product according to the present invention may further comprise a mono acyl glyceride emulsifier.
  • An ingredient that also may be present is sorbate, as a preservative.
  • the emulsion according to the invention has water droplet size with a D3,3 below 12, more preferably from 12 to 3, even more preferably from 8 to 3, yet even more preferably from to 6 to 3.2 and most preferably from 4.5 to 3.5.
  • the emulsion according to the invention has water droplet size distribution with an e-sigma of at most 3, more preferably at most 2.5, yet more preferably of at most 2.3, even more preferably of at most 1.8 and most preferably of at most 1 .4.
  • Water droplet size and distribution is herein measured by the following method.
  • the normal terminology for Nuclear Magnetic Resonance (NMR) is used throughout this method.
  • the D3,3 is the volume weighted mean droplet diameter and ⁇ (e-sigma) is the standard deviation of the logarithm of the droplet diameter.
  • the NMR signal (echo height) of the protons of the water in a water -in-oil emulsion are measured using a sequence of 4 radio frequency pulses in the presence (echo height E) and absence (echo height E * ) of two magnetic field gradient pulses as a function of the gradient power.
  • the oil protons are suppressed in the first part of the sequence by a relaxation filter.
  • the products according to the present invention have no free water (as measured with Wator test-paper).
  • the full model is based on three consecutive steps
  • Digestive enzymes are pepsin and li
  • Digestion temperature was 37 °C
  • example D had the same overall composition as A, except that it further contained a lecithin (which lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and phosphatidylethanolamine (PE) wherein the weight ratio (PC+PI)/PE in the emulsion was about 4.4).
  • lecithin comprises phosphatidylcholine (PC), phosphatidylinositol (PI), and phosphatidylethanolamine (PE) wherein the weight ratio (PC+PI)/PE in the emulsion was about 4.4.
  • Table 2 spread composition
  • Aqueous phase sample B sample A sample D
  • the USP dissolution apparatus was used for simulating the gastric step.
  • the temperature of the water was set up to 37°C.
  • the slow shear in the stomach was simulated with a special paddle at a stirring rate of 100 rpm.
  • DNJ was quantified in the water phase of gastric digestion of USP by a quantitative LC- MS method (see below).
  • Quantitative analysis was carried out on an Agilent HPLC system equipped with a triple quadrupole mass spectrometer (6410 Agilent, Amstelveen, the Netherlands).
  • the column used in all experiments was a TSK gel Amide-80 HPLC column of 2.0 mm inner diameter and a length of 150 mm, packed with 5 ⁇ particles (TOSOH, Japan). Injection volume was 5 ⁇ . Column temperature was 30 ° C. A mobile phase consisting of 0.1 % formic acid in acetonitrile (A) and 0.1 % formic acid in Milli-Q water (B) and a flow rate of 0.2 ml/min was used in all experiments.
  • a mobile phase consisting of 0.1 % formic acid in acetonitrile (A) and 0.1 % formic acid in Milli-Q water (B) and a flow rate of 0.2 ml/min was used in all experiments.
  • MRM Multiple reaction monitoring
  • MRM Multiple reaction monitoring
  • Quadrupole tandem MS system (6410 Agilent, Amstelveen, the Netherlands)
  • Mobile phase B Milli-Q water + 0.1 % formic acid

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une émulsion grasse continue comestible contenant de la 1-désoxynojirimycine (DNJ) et de la lécithine, la lécithine contenant de la phosphatidylcholine (PC), du phosphatidylinositol (PI) et de la phosphatidyléthanolamine (PE), le rapport en poids (PC+PI)/PE étant d'au moins 2/5. L'invention concerne également un procédé de préparation, ainsi que l'utilisation de cette émulsion.
PCT/EP2017/063093 2016-06-22 2017-05-31 Emulsion grasse continue comestible contenant de la 1-désoxynojirimycine et de la lécithine WO2017220298A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16175822 2016-06-22
EP16175822.2 2016-06-22

Publications (1)

Publication Number Publication Date
WO2017220298A1 true WO2017220298A1 (fr) 2017-12-28

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413674A2 (fr) * 1989-08-17 1991-02-20 Monsanto Company Prodrogues phosphorylées inhibitrices de la glycosidase
US20010018090A1 (en) * 1999-01-28 2001-08-30 Shinzo Noda Calorie reducing agent
KR20020015806A (ko) * 2000-08-23 2002-03-02 이영종 뽕잎을 함유하는 유중수형 유화물 및 이의 제조방법
KR20060111341A (ko) * 2005-04-22 2006-10-27 사회복지법인 삼성생명공익재단 1-데옥시노지리마이신을 포함하는 비만 예방 또는 치료용조성물
WO2009101698A1 (fr) * 2008-02-15 2009-08-20 Project M Co., Ltd. Composition et procédé pour supprimer l'accumulation de graisse
WO2015052037A1 (fr) * 2013-10-07 2015-04-16 Unilever N.V. Procédé de préparation d'émulsions continues émulsifiant-graisse comestible libre

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413674A2 (fr) * 1989-08-17 1991-02-20 Monsanto Company Prodrogues phosphorylées inhibitrices de la glycosidase
US20010018090A1 (en) * 1999-01-28 2001-08-30 Shinzo Noda Calorie reducing agent
KR20020015806A (ko) * 2000-08-23 2002-03-02 이영종 뽕잎을 함유하는 유중수형 유화물 및 이의 제조방법
JP2002065159A (ja) * 2000-08-23 2002-03-05 Lotte Samkang Co Ltd 桑の葉を含有する油中水型乳化物及びその製造方法
KR20060111341A (ko) * 2005-04-22 2006-10-27 사회복지법인 삼성생명공익재단 1-데옥시노지리마이신을 포함하는 비만 예방 또는 치료용조성물
WO2009101698A1 (fr) * 2008-02-15 2009-08-20 Project M Co., Ltd. Composition et procédé pour supprimer l'accumulation de graisse
WO2015052037A1 (fr) * 2013-10-07 2015-04-16 Unilever N.V. Procédé de préparation d'émulsions continues émulsifiant-graisse comestible libre

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