WO2023080785A1 - Inhibition de la patatine - Google Patents

Inhibition de la patatine Download PDF

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Publication number
WO2023080785A1
WO2023080785A1 PCT/NL2022/050624 NL2022050624W WO2023080785A1 WO 2023080785 A1 WO2023080785 A1 WO 2023080785A1 NL 2022050624 W NL2022050624 W NL 2022050624W WO 2023080785 A1 WO2023080785 A1 WO 2023080785A1
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WIPO (PCT)
Prior art keywords
patatin
lipid
food product
inhibitor
native
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PCT/NL2022/050624
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English (en)
Inventor
Robin Eric Jacobus Spelbrink
Christina Lamberta Catharina SEEGERS
Stevina Cornelia STOTER
David Ignacio Habeych NARVAEZ
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Coöperatie Koninklijke Avebe U.A.
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Application filed by Coöperatie Koninklijke Avebe U.A. filed Critical Coöperatie Koninklijke Avebe U.A.
Publication of WO2023080785A1 publication Critical patent/WO2023080785A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00—Working-up of proteins for foodstuffs
    • A23J3/22—Working-up of proteins for foodstuffs by texturising
    • A23J3/225—Texturised simulated foods with high protein content
    • A23J3/227—Meat-like textured foods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/03—Organic compounds
    • A23L29/035—Organic compounds containing oxygen as heteroatom

Definitions

  • the invention is in the field of food additives, in particular food additives which suppress off-flavor formation in food products prepared from native patatin.
  • Potato is a generally known source of starch as well as protein.
  • Potato protein can be divided into three groups: (i) a high molecular weight fraction of highly homologous acidic 35 - 50 kDa glycoproteins (40-50 w% of total potato protein), which is generally called the “patatin” fraction; (ii) low molecular weight (LMW) protein of 5-25 kDa which is generally called the “protease inhibitor” fraction (30-40 w% of total potato protein) and (iii) other proteins (10-20 w% of total potato protein).
  • PGW low molecular weight
  • Patatin is a protein which is generally known to be present as the main storage protein in potato tubers.
  • Native patatin can be isolated from potato, as described in EP 2 083 634, and can among others be used as a binding agent, a gelling agent or emulsifier in food products.
  • the application of patatin even provides for additional flavor development due to a specific hydrolytic action on C4 - C8 triglycerides, which can be used in the production of cheese (WO 2014/007621).
  • Off-flavors in food can have various origins. Off-flavors can be caused by the action of oxygen on one or more compounds present in a food product, resulting in oxidized compounds that act as off-flavors (oxidative off-flavor formation”). Off-flavors may also be caused by enzymatic action on compounds present in the food product. It has been found that the action of patatin on certain lipids can be responsible for the formation of hydrolytic off-flavor formation (rancidity) in certain food products. The present invention provides food products on the basis of lipids which in combination with patatin would normally cause off-flavors, but in which off- flavor formation is suppressed.
  • the invention pertains to the insight that native patatin may cause off- flavor formation in systems where it is present in combination with water and a lipid. This off-flavor formation can be suppressed or reduced by addition of an inhibitor of patatin, as defined below.
  • the invention thus pertains to food products comprising or prepared from water, a lipid, and native patatin, which furthermore comprise a patatin inhibitor.
  • a food product which is “prepared from” a mixture comprising native patatin may (still) comprise native patatin if the food product has not been subjected to processing steps which lead to denaturation, but that a food product which is “prepared from” a mixture comprising native patatin may also be a food product in which patatin is no longer native, due to processing steps of the food product which lead to denaturation. Therefore, a food product which is “prepared from” a mixture comprising native patatin encompasses both food products “comprising” native patatin (which may later be processed, e.g.
  • the advantage of addition of the patatin inhibitor of the invention is that off-flavor reduction caused by the action of patatin elsewhere defined is avoided, during the period in which native patatin, water and the lipid are simultaneously present.
  • off-flavor formation is avoided up to the time that the food product is processed in such a way so as to result in patatin inactivation by partial or full denaturation. From the moment of inactivation, off-flavors from an interaction between patatin and lipid do no longer form, as inactivation results in loss of the patatin off-flavor forming potential.
  • the invention is based on the insight that patatin hydrolytic action on certain lipids (specifically lipids comprising a significant quantity of C4 - C14 fatty acids, in particular C12 and C14 fatty acids) causes the formation of off-flavors, and that this off-flavor formation can be suppressed by addition of a patatin inhibitor.
  • the patatin inhibitor of the invention is a 3,4-dihydro-2H-chromen- 3-ol derivative, preferably a 2-phenyl-3,4-dihydro-2H-chromen-3-ol derivative (derivatives of the compounds known as a flavanol or flavan-3-ol).
  • Patatin inhibitors of the invention derive their strong inhibitory potency from the presence of a galloyl moiety, which provides for strong binding in the patatin active site. It has been found that patatin inhibitors of the invention bind to patatin, thereby decreasing or eliminating the off-flavor formation caused by the hydrolytic activity of patatin.
  • the invention thus provides a food product prepared from a mixture comprising water, native patatin and a lipid, which lipid is defined as a substance comprising fatty acid tri-esters of glycerol, said mixture further comprising a patatin inhibitor of formula (1): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are independently H, Cl - C4 alkyl, wherein R 8 and
  • R 9 are independently H or OH; provided that at least one of R 1 - R 7 comprises
  • formula 1 represents the 3,4-dihydro-2H-chromen-3-ol derivative of the invention.
  • a 3,4-dihydro-2H-chromen-3-ol derivative of the invention comprises at least one galloyl moiety, said galloyl moiety defined as a 3,4,5- trihydroxyphenyl moiety,
  • the patatin inhibitor of the invention is a compound according to formula 2: wherein R 3 , R 4 and R 7 are independently H or C1-C4 alkyl, and wherein preferably, R 3 , R 4 and R 7 are all H, and wherein R 2 , R 8 and R 9 are as defined above.
  • formula 2 represents the 2-phenyl-3,4-dihydro-2H-chromen-3- ol derivative of the invention.
  • the patatin inhibitor of formula 2 comprises at least one galloyl moiety, defined above.
  • the patatin inhibitor of the invention is a compound according to formula 3: wherein R 8 and R 9 are independently, on each occurrence, H or OH, which compound comprises at least one galloyl moiety, defined above.
  • the patatin inhibitor of formula 1 is a compound according to formula 4: wherein R 8 , on each occurrence, is independently H or OH, provided that the compound comprises at least one galloyl moiety, defined above. Most preferably, in the compound according to formula 4, R 8 is OH on each occurrence.
  • Patatin inhibitors of the invention comprise at least two adjacent chiral centers, the stereochemistry of which is not particularly limiting.
  • the substitution pattern on the two adjacent chiral centers is syn, and the general name is, in the exemplary case of formula 2, an “epi” catechin.
  • the substitution pattern on the two adjacent chiral centers is anti, and the general name is a “catechin”.
  • Appropriate naming of patatin inhibitors based on catechin- and gallocatechin- derivatives as described herein is generally known in the art.
  • the patatin inhibitor of the invention comprises epigallocatechin gallate (EGCG), preferably (-)-EGCG (formula 5), and/or epigallocatechin (EGO), preferably (-)-EGC (formula 6), most preferably EGCG.
  • EGCG epigallocatechin gallate
  • EGO epigallocatechin gallate
  • EGO epigallocatechin gallate
  • the patatin inhibitor can be a single, chemically pure compound, of a formula as defined above.
  • a patatin inhibitor of the invention can also be a mixture of different patatin inhibitors according to any of formulas 1 - 6.
  • the patatin inhibitor of the invention preferably comprises at least 10 % epigallocatechin gallate (EGCG).
  • the patatin inhibitor mixture comprises, in addition to the at least 10 % epigallocatechin gallate (EGCG), over 20% of different catechins, preferably as defined above.
  • the food product of the invention is prepared from a mixture comprising water, native patatin and a lipid, which lipid is defined as a substance comprising fatty acid tri-esters of glycerol.
  • Off-flavor development may occur at any time that the patatin is native, and is present in a mixture comprising water and a lipid. This off-flavor formation is suppressed by the addition of a patatin inhibitor of the invention.
  • Native patatin is a protein which occurs in tubers, such as tubers of potato (Solanum tuberosum). The skilled person is aware which of the protein in a tuber can be considered patatin.
  • Patatin is a protein which is naturally present in the tuber as storage protein.
  • Storage protein is protein which functions as a store for nitrogen, sulphur and/or carbon, enabling the plant to survive periods of adverse growth conditions or between growing seasons.
  • Storage protein (patatin) is generally present in a quantity of 40 - 50 wt.% of all protein in the tuber.
  • Storage protein can generally be characterized by a molecular weight of 35 - 50 kDa, preferably 38 - 45 kDa and/or by an isoelectric point of 4.8 - 5.6.
  • the molecular weight can be determined by commonly known methods, such as SDS page.
  • the isoelectric point can also be determined by commonly known methods, such as for example isoelectric focusing.
  • native patatin is preferably provided to the mixture in the form of a protein isolate comprising native patatin.
  • the protein isolate comprising native patatin is a native tuber protein isolate, preferably a native potato protein isolate.
  • protein is preferably present in a quantity of at least 75 wt.%, preferably at least 85 wt.%, relative to dry matter.
  • the native tuber protein isolate such as the native potato protein isolate, comprises, by wt.% of total protein, at least 35 wt.% of native patatin, preferably at least 40 wt.%. In embodiments where there is from 35 up to 60 wt.% of native patatin, relative to total protein, the tuber protein isolate can be called a total tuber protein isolate.
  • the native tuber protein isolate such as the native potato protein isolate, comprises, by wt.% of total protein, at least 75 wt.% of native patatin, preferably at least 80 wt.%. In embodiments where there is 60 wt.% or more up to 85 wt.% of native patatin, relative to total protein, the tuber protein isolate can be called a HMW (high molecular weight) isolate comprising patatin.
  • HMW high molecular weight
  • the native tuber protein isolate such as the native potato protein isolate, comprises, by wt.% of total protein, at least 90 wt.%, more preferably at least 95 wt.% of native patatin. In embodiments where there is 90 wt.% or more up to and including 100 wt.% of native patatin, relative to total protein, the tuber protein isolate can be called a patatin isolate.
  • a patatin isolate is Solanic 200 from Avebe.
  • Native patatin can be isolated from potato tubers, or from other potato- derived processing streams such as potato juice (for example the juice obtained as a side product in potato starch manufacturing), or potato cutting water (the processing water which is obtained when potatoes are being shaped for consumption as for example fries or chips). Native patatin is commercially available, as an isolate or as a mixture comprising other native tuber proteins.
  • potato juice for example the juice obtained as a side product in potato starch manufacturing
  • potato cutting water the processing water which is obtained when potatoes are being shaped for consumption as for example fries or chips.
  • Native patatin is commercially available, as an isolate or as a mixture comprising other native tuber proteins.
  • native patatin is used in the state in which it occurs in nature. That is, native patatin is preferably not modified, such as by crosslinking or complexation.
  • native patatin is by definition a non-denatured protein; that is, native patatin is patatin which is capable of performing its natural biochemical function(s). Native patatin thus is not appreciably denatured, and has not been subjected to for example coagulation, such as heat coagulation or acid coagulation. Native patatin in this definition means that less than 25% of the protein is denatured relative to total protein.
  • Native patatin can be present in the mixture comprising water, native patatin and a lipid at any quantity, such as from 0.1 - 25 wt.%, preferably 0.5 - 20 wt.%, more preferably 0.75 - 15 wt.%, based on the total weight of the mixture.
  • native patatin can be present in a quantity of 0.1 - 50 wt.%, preferably 0.2 - 45 wt.%, more preferably 0.3 - 40 wt.%, more preferably 0.3 - 30 wt.%, more preferably 0.3 - 30 wt.%, more preferably 0.3 - 25 wt.%, more preferably 0.3 - 20 wt.%, most preferably 0.4 - 10 wt.%.
  • the lipid can be present in the mixture comprising water, native patatin and a lipid in any quantity, such as from 0.1 - 50 wt.%, preferably 0.5 - 25 wt.%, more preferably 5 - 15 wt.%, relative to the total weight of the mixture. Relative to the dry matter, the lipid can be present in a quantity of 0.2 - 50 wt. %, preferably 1 - 40 wt.%, more preferably 5 - 35 wt.%, even more preferably 10 - 30 wt. %.
  • the patatin inhibitor can be present in the mixture comprising water, native patatin and a lipid in a quantity of 0.01 - 1 wt.%, preferably 0.02 - 0.5 wt .%, relative to the total weight of the mixture. Relative to the dry matter, the patatin inhibitor can be present in a quantity of 0.02 - 2 wt.%, preferably 0.04 - 1.0 wt. %, more preferably 0.1 - 0.5 wt.%.
  • the patatin inhibitor is preferably present in the mixture comprising water, native patatin and a lipid in quantity of at least 0.9 mg patatin inhibitor per 100 mg native patatin, preferably at least 4.5 mg inhibitor per 100 mg native patatin, more preferably at least 7.9 mg patatin inhibitor per 100 mg native patatin, such as preferably 10 - 50 mg patatin inhibitor per 100 mg native patatin, more preferably 15 - 40 mg patatin inhibitor per 100 mg native patatin.
  • the patatin inhibitor is preferably present in a quantity of at least 1 molar equivalent to the native patatin, more preferably at least 3 molar equivalents, more preferably at least 5 molar equivalents, most preferably at least 10 molar equivalents.
  • the patatin inhibitor is present in a quantity of 5 - 45 molar equivalents, more preferably 10 - 35 molar equivalents, even more preferably 15 - 30 molar equivalents.
  • Water also, can be present in any quantity, such as in a quantity of 5 - 95 wt.%, preferably 10 - 90 wt.%, more preferably 15 - 85 wt.%, even more preferably 25 - 75 wt.%, most preferably 35 - 65 wt.%, relative to the total weight of the mixture.
  • the quantity of water varies with the type of food product being prepared, as is well known in the art. The exact mechanism behind off-flavor formation in food products comprising native patatin is at present not understood.
  • patatin which causes off-flavors may be hydrolytic, but may also be another, yet unknown enzymatic activity of patatin, which activity is suppressed by combination with a patatin inhibitor as herein defined.
  • off-flavor formation by patatin will be called “hydrolytic” off-flavor formation.
  • the examples show that formulating a food product in line with the present invention suppresses off-flavor formation, in particular hydrolytic off-flavor formation.
  • Hydrolytic off-flavor formation is the formation of off-flavors through an enzymatic hydrolytic action of patatin on certain lipids. Hydrolytic off-flavor formation is distinct from oxidative off-flavor formation.
  • Off-flavors in the present context are defined as a lingering bitter sensation upon ingestion, which is accompanied by a stingy smell that can be described as “paint” or “vomit”.
  • the off-flavors which may be suppressed following the present invention may also be called rancidity.
  • Off-flavor can preferably be determined by sensory evaluation. Off flavor can also be determined in model systems by measuring the release of free fatty acids using a chemical titration method after hexane extraction. Off- flavor can be defined as not present provided that the release of free fatty acids from the lipid is less than 50 mmol/kg oil, preferably less than 40 mmol. /kg oil.
  • suitable food products to prepare using the present invention include food products in which patatin is present in native form.
  • Such food products include preferably food products which have not been subjected to a heating step, such as a step of heating the food product to a temperature of higher than 75 °C.
  • patatin is preferably present as a binding agent, a gelling agent or an emulsifier.
  • the food product is prepared by a method comprising a step of retaining the mixture comprising native patatin, the lipid and the compound according to formula 1 at a temperature of -35 - 20 °C, preferably 0 - 20 °C for a period of at least 1 hour, preferably at least 12 hours, more preferably at least 24 hours.
  • the food product is made without subjecting it to a heating step as defined and while keeping the food product cool as defined until consumption by a consumer.
  • the food product comprises native patatin in a mixture with water and the lipid throughout the period from production until consumption.
  • a patatin inhibitor as defined herein, off-flavor formation, in particular hydrolytic off-flavor formation, is suppressed, thereby prolonging the shelf-life of the food product.
  • the food product may be heated prior to consumption by a consumer.
  • Such heating may include cooking customary for the food product in question.
  • patatin reactivity is first accelerated, thereby accelerating off-flavor development, prior to denaturation and concomitant inactivation of the patatin.
  • off-flavor development during heating is also suppressed by a patatin inhibitor as herein defined.
  • Food products include any food product which comprises, or has been prepared from, a mixture comprising water, native patatin and a lipid.
  • Such food products include for example a meat substitute, batter, dough, bakery product, cheese, cream cheese, butter, yoghurt, sauce, dressing, mayonnaise, cream, or a fried snack.
  • two types of food product may be distinguished, on the basis of the mechanisms by which off-flavors develop: food products which develop off-flavors due to a prolonged period in which native patatin is in contact with the lipid (“cold storage” type food product), and food products which develop off-flavors due to a brief heat shock in which native patatin is in contact with the lipid (“heat shock” type food products).
  • the prolonged period in which native patatin is in contact with the lipid is generally a storage period, preferably cold storage.
  • Storage includes any prolonged period in which no active steps are taken on the food product. Storage thus means that the food product is left to stand, for any reason, including one or more of storage prior to sale or transport, a period of gelation, or a period of ripening, maturing or fermenting.
  • Cold storage type food products are food products where making the food product comprises a step of cooling to a temperature of from -35 °C to 20 °C, preferably 0 - 20 °C.
  • a cold storage type food product has not been heated to a temperature above 60 °C prior to cooling.
  • Cold storage type food products are food products comprising water, patatin and a lipid, in which the native patatin is in contact with the lipid during a period of storage, wherein during the period of storage, the patatin is native, thereby having the potential to cause off-flavor formation, which off-flavor formation is suppressed by combination with a patatin inhibitor as herein defined.
  • Heat shock type food products are food products where making the food product comprises a step of heating the food product to a temperature of at least 75 °C, preferably at least 125 °C, more preferably at least 150 °C for a period of at least 1 minute, preferably at least 15 minutes.
  • Heat shock type food products are food products which are prepared from a mixture of water, native patatin and a lipid, in which the native patatin is in contact with the lipid, and in which the rise in temperature during heating causes off-flavor formation prior to denaturation and concomitant inactivation of the patatin.
  • heat shock type food products are generally bakery products, such as a muffin, cookie, cake, pie, macaron, sponge cake or waffle.
  • a further preferred heat shock type food product is a fried snack (a product with a crust and an inner filling, which may be prepared by heating to a temperature of 150 - 200 °C in fat or oil), such as a croquette, nugget, fish finger, spring roll or lumpia, most preferably a plant-based (vegan) fried snack.
  • the invention pertains to a food product comprising a mixture comprising water, native patatin and a lipid, which lipid is defined as a substance comprising fatty acid tri-esters of glycerol, said mixture further comprising a patatin inhibitor as defined above, as well as to a food product obtained by heating a mixture comprising water, native patatin and a lipid, which lipid is defined as a substance comprising fatty acid tri-esters of glycerol, said mixture further comprising a patatin inhibitor as defined above.
  • Heating a food product in the context of this invention, is intended to refer to the core temperature of the food product.
  • a meat substitute preferably a raw-type meat substitute (defined as a meat substitute which has not been subjected to heating to a temperature of higher than 75 °C prior to cooking by a consumer).
  • a patatin inhibitor of the invention By including in said mixture a patatin inhibitor of the invention, off-flavor development is suppressed, which prolongs shelf-life of the meat substitute. In addition, off-flavor formation occurring during cooking of the meat substitute is also suppressed.
  • a food product of the invention is a vegan food product, defined as a food product based only on plant-derived ingredients.
  • a vegan food product can also be defined as a food product free of animal-derived ingredients.
  • a vegan food product is much preferred, because lipids in such food products are generally plant -based lipids, which are provided separately to the mixture, thereby allowing greater control over the composition of the lipids in the food product.
  • Any lipid may be used in a food product of the invention, as lipids of any composition will in time result in off-flavor formation caused at least in part by the presence of native patatin.
  • Much preferred lipids are plant-based lipids, such as a seed oil, nut oil, or fruit oil. Mixtures of different lipids may also be used.
  • Particularly preferred lipids comprise one or more of the lipids in the group of coconut fat, palm oil, corn oil, soybean oil, rapeseed oil, sunflower oil, grape seed oil, peanut oil, sesame oil, canola oil, olive oil, shea butter, cocoa butter, and rice bran oil.
  • the lipid may be partially hydrogenated.
  • off-flavor formation is particularly fast when native patatin is present in a mixture comprising water and a lipid (which lipid is defined as a substance comprising fatty acid tri-esters of glycerol), in cases where the fatty acids in said lipid comprise more than 2 % by mass of fatty acids having a chain length of 4 - 14 carbon atoms, in particular wherein the fatty acids in said lipid comprise more than 2 % by mass of fatty acids having a chain length of 12 - 14 carbon atoms.
  • lipid which lipid is defined as a substance comprising fatty acid tri-esters of glycerol
  • the invention thus provides a food product in which the fatty acids in the lipid comprise more than 2 % by mass of fatty acids having a chain length of 4 - 14 carbon atoms, in particular wherein the fatty acids in said lipid comprise more than 2 % by mass of fatty acids having a chain length of 12 - 14 carbon atoms.
  • the food product of the invention is prepared from a mixture comprising a coconut or palm derived lipid, preferably coconut fat or palm oil.
  • the lipid to be provided to the mixture is preferably as pure as possible.
  • the quantity of free fatty acids (“FEA”) in the lipid is preferably less than 18 mmol per kg lipid, more preferably less than 9 mmol per kg lipid, even more preferably less than 3 mmol per kg lipid.
  • the quantity of free fatty acids in the lipid can be determined by a chemical titration method, as described below.
  • the quantity of free fatty acids can also be determined by HPLC, as is generally known in the art.
  • the total quantity of diacylglycerols (“DAG”) and monoacylglycerols (“MAG”) in the lipid to be provided to the mixture is preferably less than 10 wt.%, more preferably less than 6 wt.%, even more preferably less than 4 wt.%, relative to the total lipid.
  • the quantity of DAG and MAG in the lipid can be determined by column chromatography or capillary gas chromatography as described in “Standard Methods for the Analysis of Oils, Fats and Derivatives”, 1 st supplement to the 7 th edition (IUPAC, 1987).
  • the invention furthermore provides a method for making a food product comprising a lipid, comprising a step of mixing a patatin inhibitor as defined in formula 1, preferably formula 2, more preferably formula 3, and even more preferably formula 4, with native patatin in water.
  • the patatin inhibitor comprises EGCG or EGO, as defined above. This method has the effect that off-flavor formation caused by patatin, in particular hydrolytic off-flavor formation, is reduced.
  • the food product thus has reduced off-flavors, as compared to a food product which does not comprise the patatin inhibitor of the invention but which is otherwise the same.
  • the type of food product which may be prepared using the present method is not particularly limited.
  • the method for preparing the food product is preferably conventional for the preparation of the type of food product in question; reference is made to common general knowledge on the preparation of food products.
  • the preparation of food products according to the invention, as well as the food products resulting from said preparation are distinguished from known food products and methods in that a patatin inhibitor is combined with (mixed with) native patatin during the preparation of said food product.
  • the method comprises a step of combining native patatin with the patatin inhibitor of the invention in water prior to combination with the lipid.
  • the invention further provides a method for reducing off-flavor formation caused by the action of patatin on a lipid, preferably the hydrolytic action of patatin, said method comprising a step of mixing a patatin inhibitor as defined in formula 1, preferably formula 2, more preferably formula 3, and even more preferably formula 4, with native patatin in water, thereby providing a mixture comprising inhibited patatin.
  • the method of the invention reduces hydrolytic off-flavors.
  • the method further comprises steps conventional for making the food product in question.
  • the method for reducing off-flavor formation caused by the action of patatin on a lipid preferably further comprises a step of mixing the mixture of inhibited patatin with a lipid.
  • the lipid may already be comprised in the mixture comprising inhibited patatin, by a preceding step of lipid addition.
  • the method for reducing off-flavors caused by the hydrolytic action of patatin comprises one or more steps for making a food product, said food product comprising or being prepared from a lipid, native patatin and water, wherein said method further comprises a step of addition of a patatin inhibitor as herein defined so as to provide a food product comprising a lipid and inhibited patatin.
  • Another embodiment of the invention is an emulsion comprising water, lipid, native patatin and patatin inhibitor as defined above. This emulsion is an intermediate which may be used to prepare a food product of the invention.
  • the emulsion of the invention is used as an intermediate product for obtaining a sauce, mayonnaise, dressing, cream, or a cheese, but the emulsion can also be used, as an intermediate product, as carrier for lipids, for example by combining the emulsion with further ingredients, to obtain the food product.
  • emulsion comprising water, lipid, native patatin and patatin inhibitor as defined above, which can be combined with vegetable protein in order to obtain a meat substitute.
  • an emulsion of the invention comprises a quantity of 10 - 90 wt.%, preferably 20 - 80 wt.% of the lipid, and/or a quantity of native patatin of 0.5 - 10 wt.%, preferably 1.0 - 5.0 wt.%, and/or a quantity of patatin inhibitor of 0.01 - 1.0 wt.%, preferably 0.1 to 0.5 wt.%, relative to the total weight of the emulsion.
  • An emulsion of the invention can be obtained by mixing patatin and patatin inhibitor in water, and subsequent addition of the lipid and homogenization to obtain the emulsion.
  • the invention thus also provides a method for preparing an emulsion, comprising mixing the native patatin and the patatin inhibitor in water to obtain a patatin -inhibited premix, combining the patatin-inhibited premix with the lipid to obtain a lipid premix, and homogenizing the lipid premix to obtain the emulsion.
  • the patatin used is commercially available as a native patatin isolate (Solanic 200®, Avebe).
  • the lipid used was solid at room temperature: 100 % pure coconut oil (KTC).
  • a patatin solution was prepared of 6.6 % in demineralized water.
  • a patatin inhibitor solution was prepared in demineralized water.
  • the patatin and patatin inhibitor solution were mixed to obtain a final concentration of 5 wt. % patatin.
  • Solid lipids were melted at 50 °C.
  • the lipid was added in a 1:1 (w/w) ratio to the patatin solution or to demineralized water, which served as a control.
  • the solutions were mixed by turrax for 1 minute at about 10.000 rpm. Then, the solutions were left at room temperature overnight under gently shaking so that release of fatty acids and fat oxidation could occur.
  • hexane was added in a quantity of about 5 ml per 2-gram solution, and the sample was vortexed several times in a time frame of 30 minutes to extract the lipids from the aqueous phase. Subsequently, the layers were separated by centrifugation (5 minutes, 4700 rpm, swing-out). The hexane layer (top layer) was used for determination of free fatty acids. The protocol above was followed unless indicated otherwise.
  • Patatin cleaves the ester linkage between a fatty acid and the glycerol core, producing free fatty acids, which are at least partially responsible for off- flavor formation. Titrimetry was used to determine the free fatty acid content of mixtures of patatin and a lipid after hexane extraction. The method is based on chemical titration method published by the Cyberlipid Center (Leray).
  • a solvent mixture (ethanol I tert-butyl methyl ether, 1/1 v/v) was prepared and 10 ml phenolphthalein solution was added.
  • As titrant a 10 mM KOH in ethanol solution was prepared by dissolving an accurately weighed quantity of potassium hydroxide of approximately 561 mg in an accurately weighed quantity of ethanol of approximately 1000 grams.
  • the hexane layer of the oil phase was transferred by a glass pipet to a 100 ml Erlenmeyer with cap. Solvent mixture was added to obtain approximately 30 - 50 ml solution. Titrant was added while stirring the solution on a magnetic stirrer to the end point of the indicator. The titration was judged complete when the solution turned a purple color that persisted for at least 10 seconds. The amount of titrant added was determined by weighting the Erlenmeyer before and after titrant addition. The weight was used to calculate the mmol alkaline / kg of oil was used. The value was corrected for a control determination on a sample without added lipid.
  • Mtitrant is the molar mass in mmol KOH / g titrant
  • m O ii is the mass of oil in the sample in g.
  • PBRMB plant-based raw meat burgers
  • Table 1 Recipe of the plant based raw meat burger
  • Solanic 200 (Avebe; 90 wt.% native patatin) 5 5
  • the green tea extract comprises at least 10 % epigallocatechin gallate (EGCG) and over 20% catechins
  • Textured soy protein and textured wheat protein was hydrated for 60 minutes at ambient temperature.
  • the other ingredients shown in table 1 except for the lipids were premixed.
  • the hydrated proteins were transferred to a Hobart mixer set for low mixing with a paddle blade and the sunflower oil was added over 30 seconds. Then the other pre-mixed ingredients were added and the resulting composition was mixed for two minutes.
  • liquid coconut fat 50 °C was mixed into the material, followed by one more minute of mixing.
  • the resulting mass was pressed into uniform 100 gram patties with a hamburger mold.
  • the burgers were either baked within 30 minutes of manufacture in a non-stick pan or stored in a refrigerator at 4-7 C for 24 hours.
  • Burgers were baked to a core temperature of 75 °C and examined by a sensory panel consisting of 3 persons on the typical patatin-coconut fat off-flavor.
  • Table 2 Sensory results of taste session of plant based raw meat burgers
  • Off-flavor formation in various food products prepared from native patatin and a lipid can be suppressed by suppressing free fatty acid development.
  • This off-flavor formation can be modelled by preparation of an emulsion comprising native patatin, a lipid and a patatin inhibitor as herein defined.
  • a 10 wt. % solution of a native patatin isolate (about 90 wt.% native patatin, Solanic 200, Avebe) was prepared in demineralized water.
  • Coconut fat (KTC Premium Quality) was melted at 50 °C. 2 grams of molten coconut fat were added to an aqueous phase consisting of 1 gram of the patatin solution and optionally in combination with patatin inhibitor solutions and enough water to bring the total weight of the aqueous phase to 2 grams.
  • the mixture was emulsified by turrax for 30 seconds at 10.000 rpm using an IKA T25 Ultraturrax with T25N disperging tool.
  • the emulsion was left at room temperature overnight (or for as long as indicated) under gently shaking.
  • 10 mL of hexane were added and the samples were vigorously agitated to extract the lipids from the emulsion.
  • the layers were separated by centrifugation (5 minutes, 4700 rpm, in a Multifuge 1S-R (Thermo Scientifc) equipped with a swing-out rotor).
  • the hexane layer was used for determination of free fatty acids as described above.
  • the results show a time-dependent increase in free fatty acid content.
  • Table 3 free fatty acid contents in the oil phase of coconut fat emulsions after exposure to potato protein comprising native patatin when stored at room temperature.
  • Table 4 suppression of free fatty acid release after 24 hours at room temperature by catechin and ECGC.
  • Table 5 binding energy of catechin and EGCG to native patatin in silico.
  • Table 6 residual free fatty acid release at varying quantities of EGCG.
  • the patatin inhibitors herein defined may also be obtained from a biological origin. Modelling emulsions were prepared as described in example 2, using (for the inventive compositions), green tea extract in various quantities, rather than pure catechin or EGCG.
  • the green tea extract obtained from bulkpowders.com
  • the results of incubation for 24 hrs at room temperature are shown in table 7.
  • Table 7 residual free fatty acid release at varying quantities of green tea extract.
  • Table 8 Compositions of test solutions for gel strength measurement
  • Gelation was induced by heating the beakers in a water bath at 90 °C for 45 minutes.
  • the water level in the bath was such that the water in the bath and in the beakers was the same.
  • the beakers were then removed from the bath and cooled overnight in a refrigerator until the core temperature was between 7 and 10 °C.
  • a series of raw meat burgers were prepared according to the recipes in Table 10. The burgers were prepared and stored for 2 hours and baked in non-stick pans in a small quantity of sunflower oil.
  • PBRMB standard In Table 10, “PBRMB standard”, “PBRMB porcine lipase”, and “PBRMB porcine lipase Green Tea Extract” recipes relate to control experiments.
  • the “PBRMB Green Tea Extract” recipe relates to food products according to the invention.
  • the prepared burgers were then evaluated on the characteristic off taste that is associated with coconut fat lipolysis, by two sensory panelists that had experience with the product.
  • the burger prepared with native potato protein but without green tea extract had developed a mild but noticeable flavour defect.
  • the burger with green tea extract did not have any noticeable off flavours.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Preparation And Processing Of Foods (AREA)

Abstract

La présente invention repose sur l'idée que la patatine native peut provoquer une formation de flaveur anormale dans des systèmes où elle est présente en combinaison avec de l'eau et un lipide. Cette formation de flaveur anormale peut être supprimée ou réduite par ajout d'un inhibiteur de patatine. L'invention concerne ainsi des produits alimentaires comprenant de l'eau, un lipide et de la patatine native ou préparés à partir de ceux-ci, qui comprennent en outre un inhibiteur de patatine.
PCT/NL2022/050624 2021-11-03 2022-11-03 Inhibition de la patatine WO2023080785A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1754702A1 (fr) * 2004-05-27 2007-02-21 Suntory Limited Dimères ou trimères d'épigallocatéchine ayant une activité d'inhibition de la lipase et/ou une activité antioxydante
EP1920662A1 (fr) * 2006-11-10 2008-05-14 Coöperatie Avebe U.A. Isolat de protéine de pomme de terre à l'ètat naturel
WO2014007621A1 (fr) 2012-07-04 2014-01-09 Coöperatie Avebe U.A. Procédés d'utilisation de patatine
WO2015126716A1 (fr) * 2014-02-19 2015-08-27 Abbott Laboratories Compositions nutritionnelles liquides comprenant de la gcg et de la egcg
EP3628173A1 (fr) * 2014-03-31 2020-04-01 Impossible Foods Inc. Répliques de viande hachée
CN111528483A (zh) * 2020-05-21 2020-08-14 青岛自然珍萃生物科技有限公司 一种均衡营养的功能代餐粉及其制备方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1754702A1 (fr) * 2004-05-27 2007-02-21 Suntory Limited Dimères ou trimères d'épigallocatéchine ayant une activité d'inhibition de la lipase et/ou une activité antioxydante
EP1920662A1 (fr) * 2006-11-10 2008-05-14 Coöperatie Avebe U.A. Isolat de protéine de pomme de terre à l'ètat naturel
EP2083634A1 (fr) 2006-11-10 2009-08-05 Coöperatie AVEBE U.A. Isolats de protéine native de pomme de terre
WO2014007621A1 (fr) 2012-07-04 2014-01-09 Coöperatie Avebe U.A. Procédés d'utilisation de patatine
WO2015126716A1 (fr) * 2014-02-19 2015-08-27 Abbott Laboratories Compositions nutritionnelles liquides comprenant de la gcg et de la egcg
EP3628173A1 (fr) * 2014-03-31 2020-04-01 Impossible Foods Inc. Répliques de viande hachée
CN111528483A (zh) * 2020-05-21 2020-08-14 青岛自然珍萃生物科技有限公司 一种均衡营养的功能代餐粉及其制备方法

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Title
O. TROTTA. J. OLSON: "AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading", JOURNAL OF COMPUTATIONAL CHEMISTRY, vol. 31, 2010, pages 455 - 461
ROBIN E. J. SPELBRINK ET AL: "Potato Patatin Generates Short-Chain Fatty Acids from Milk Fat that Contribute to Flavour Development in Cheese Ripening", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 176, no. 1, 27 March 2015 (2015-03-27), New York, pages 231 - 243, XP055648817, ISSN: 0273-2289, DOI: 10.1007/s12010-015-1569-3 *

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