WO2014027139A1 - A method for reducing the content of gluten proteins in a cereal fraction - Google Patents
A method for reducing the content of gluten proteins in a cereal fraction Download PDFInfo
- Publication number
- WO2014027139A1 WO2014027139A1 PCT/FI2013/050796 FI2013050796W WO2014027139A1 WO 2014027139 A1 WO2014027139 A1 WO 2014027139A1 FI 2013050796 W FI2013050796 W FI 2013050796W WO 2014027139 A1 WO2014027139 A1 WO 2014027139A1
- Authority
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- WIPO (PCT)
- Prior art keywords
- cereal starch
- cereal
- fraction
- present
- gluten
- Prior art date
Links
- 235000013339 cereals Nutrition 0.000 title claims abstract description 84
- 108010068370 Glutens Proteins 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 48
- 229920002472 Starch Polymers 0.000 claims abstract description 89
- 235000019698 starch Nutrition 0.000 claims abstract description 83
- 239000008107 starch Substances 0.000 claims abstract description 83
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 230000001590 oxidative effect Effects 0.000 claims abstract description 19
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 16
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 14
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000000593 degrading effect Effects 0.000 claims abstract description 7
- 241000209219 Hordeum Species 0.000 claims description 20
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 235000021312 gluten Nutrition 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 10
- 235000007238 Secale cereale Nutrition 0.000 claims description 9
- 241000209056 Secale Species 0.000 claims description 8
- 241000209140 Triticum Species 0.000 claims description 8
- 235000021307 Triticum Nutrition 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 7
- 229940100445 wheat starch Drugs 0.000 claims description 6
- 235000018102 proteins Nutrition 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 235000012041 food component Nutrition 0.000 claims description 4
- 239000005417 food ingredient Substances 0.000 claims description 4
- 238000000265 homogenisation Methods 0.000 claims description 4
- 238000000527 sonication Methods 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 241000209763 Avena sativa Species 0.000 claims description 2
- 235000007558 Avena sp Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000000727 fraction Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- 108060006613 prolamin Proteins 0.000 description 12
- 208000015943 Coeliac disease Diseases 0.000 description 11
- XXRYFVCIMARHRS-UHFFFAOYSA-N propan-2-yl n-dimethoxyphosphorylcarbamate Chemical compound COP(=O)(OC)NC(=O)OC(C)C XXRYFVCIMARHRS-UHFFFAOYSA-N 0.000 description 11
- 230000008901 benefit Effects 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 9
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 8
- 230000000975 bioactive effect Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 108010061711 Gliadin Proteins 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 206010052805 Drug tolerance decreased Diseases 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 230000031787 nutrient reservoir activity Effects 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241001329985 Triticeae Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000002805 Triticum turgidum Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 108010051489 calin Proteins 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- -1 proline amino acid Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- 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
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
- A23L7/10—Cereal-derived products
-
- 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
- A21D13/00—Finished or partly finished bakery products
- A21D13/06—Products with modified nutritive value, e.g. with modified starch content
- A21D13/064—Products with modified nutritive value, e.g. with modified starch content with modified protein content
-
- 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
- A21D13/00—Finished or partly finished bakery products
- A21D13/06—Products with modified nutritive value, e.g. with modified starch content
- A21D13/064—Products with modified nutritive value, e.g. with modified starch content with modified protein content
- A21D13/066—Gluten-free products
-
- 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
-
- 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
-
- 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
- A23J3/14—Vegetable proteins
- A23J3/18—Vegetable proteins from wheat
-
- 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
- A23J3/30—Working-up of proteins for foodstuffs by hydrolysis
-
- 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
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/212—Starch; Modified starch; Starch derivatives, e.g. esters or ethers
- A23L29/219—Chemically modified starch; Reaction or complexation products of starch with other chemicals
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/18—Oxidised starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/04—Starch derivatives, e.g. crosslinked derivatives
- C08L3/10—Oxidised starch
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the invention relates to a method for reduc ⁇ ing the content of gluten proteins in a cereal starch fraction, to a cereal starch fraction obtained by the method, and to the uses thereof.
- Proline is an amino acid frequently occurring in the sequence of cereal storage proteins. Proline makes a polypeptide chain to turn in a tight helical structure packing it effectively in the storage pro- tein bodies of the seed. Prolamins are gluten proteins rich in proline, and in addition to their high proline content they are also rich in glutamine. Prolamins are characterized by their water-insolubility, but instead they are typically soluble in aqueous alcohol. The prolamins of three cereals, i.e. wheat, rye and bar ⁇ ley, which are also called Triticeae cereals, are con ⁇ sidered to contain sequences harmful to those having gluten intolerance or celiac disease.
- Celiac disease also referred to as gluten enteropathy or non-tropical sprue
- gluten enteropathy is an autoimmune disorder of the small intestine that occurs in genet ⁇ ically predisposed people of all ages.
- the character ⁇ istic symptom of this disease is the damage of the ep ⁇ ithelium of small bowel and intolerance to wheat glu- ten.
- the products containing wheat proteins as well as barley and rye should be eliminated from the diet of people suffering from this disease.
- the triggering peptide causing celiac disease still remains somewhat unclear.
- the toxic sequence is present in prolamins of some cereals, and that these proteins, which are generally called as gluten proteins, are characterised by a high content of proline amino acid.
- the inventors have recognized a need for an effective method for reducing the content of gluten proteins in a cereal starch fraction in a non- enzymatic manner.
- the purpose of the invention is to provide a new type of method for reducing the content of gluten proteins in a cereal starch fraction, and to provide a cereal starch fraction with reduced gluten content for different applications.
- the cereal starch fraction according to the present invention is characterized by what is present ⁇ ed in claim 10.
- the food ingredient according to the present invention is characterized by what is presented in claim 11.
- the food product according to the present in ⁇ vention is characterized by what is presented in claim
- the use according to the present invention is characterized by what is presented in claim 13.
- Fig. 1 shows pasting properties of barley starch oxidized by Cu 2+ /H 2 0 2 at pH 4.5 and 7.4 as ana ⁇ lyzed by rapid visco analyser (RVA) .
- the control was native barley starch.
- the present invention relates to a method for reducing the content of gluten proteins in a cereal fraction, wherein gluten protein comprises proline, and wherein the method comprises the step of: a) sub ⁇ jecting the cereal fraction to an oxidative treatment for degrading the gluten proteins into peptides.
- the present invention relates to a method for reducing the content of gluten proteins in a cereal starch fraction, wherein gluten protein comprises proline, and wherein the method comprises the step of: a) subjecting the cereal starch fraction to an oxidative treatment for degrading the gluten proteins into pep ⁇ tides .
- gluten proteins or any corresponding expression should be understood in this specification, unless otherwise stated, as proteins found in cereal that are considered to be harmful to a person with celiac disease and/or an intolerance to gluten.
- the gluten proteins are cereal prolamins and/or glutelins found in the Triticeae cereals, i.e. in wheat, rye and barley.
- the prolamins of these cereals in particular are considered to contain protein sequences harmful to those having gluten intolerance or celiac disease.
- These prolamins include gliadin, which can be found in wheat, hordein which can be found in barley, and se- calin, which can be found in rye.
- step a) is carried out in an aqueous suspension.
- the cereal fraction used in the present in ⁇ vention is a cereal starch fraction.
- the cereal starch frac ⁇ tion comprises wheat, rye, barley, oat, or any combi ⁇ nation thereof.
- the cereal starch is selected from a group consisting of wheat starch, rye starch, barley starch, and any combination thereof.
- the cereal starch fraction comprises wheat, rye, barley, or any combination thereof.
- step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to at least one oxidizing agent.
- step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch frac ⁇ tion to the presence of at least one oxidizing agent.
- the at least one oxidizing agent is selected from a group consisting of hydrogen peroxide, ascorbic acid, tita ⁇ nium oxide, and any combination thereof.
- step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to heat, shear forces, homogenisation, sonication, or to any combination thereof.
- Such treatments can also be used to control structural proper ⁇ ties, e.g. viscosity and sliminess of polysaccharides, of the cereal starch fraction while at the same time promoting gelling properties of polysaccharide frag- ments.
- step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to heat, shear forces, homogenisation, sonication, or to any combination thereof before, simultaneously and/or after subjecting the cereal starch fraction to at least one oxidizing agent.
- the ox ⁇ idizing treatment affects proline present in the amino acid sequence of gluten proteins.
- the bond between proline and an adjacent amino acid in the amino acid sequence is cleaved resulting in the gluten protein being degraded.
- the degradation of the gluten proteins results in smaller peptides being formed.
- the formed peptides are found to be bioactive and potentially health promoting and/or flavouring agents, and are not harmful to persons suffering from celiac disease or to individuals being gluten intolerants.
- the advantage of the method according to the present invention is that the cereal starch fraction can be treated such that it can be consumed by persons suffering from celiac dis ⁇ ease or being gluten intolerants.
- the degradation of gluten proteins can result in the release of bioactive peptides that can have health promoting effects such as controlling blood pressure.
- the method according to the present invention can be applied for modifying ce- real gluten proteins, also called as cereal prolamin proteins, like wheat gliadin and barley hordein.
- the molar mass of the resulting peptide is less than 4000 Da, preferably less than 2000 Da, and more pref- erably less than 1000 Da.
- step a) comprises subjecting the cereal starch frac ⁇ tion to an oxidative treatment in the presence of at least one catalyzing agent, wherein the catalyzing agent comprises metal and/or transition metal.
- the catalyzing agent comprises copper and/or iron.
- the catalyzing agent compris ⁇ es Cu(II) and/or Fe(II).
- a so-called Fenton-type metal catalyzed oxidation reaction can take place, e.g. in the following manner:
- the method comprises adjusting the pH in step a) to a value of 3 - 7, preferably 4 - 5, and more preferably to about 4,5.
- the method comprises adjusting the pH in step a) for modifying the properties of the cereal starch fraction.
- the pH can be adjusted in step a) such that e.g. cereal starch being treated, is simultaneously gelatinized.
- the degradation or cleavage of gluten proteins or prolamins was found to be efficient at an acidic pH, and especially at a pH of 3 - 6. Further, it was surprisingly found out that when using acidic pH conditions in step a) , the oxidative treatment has no effect on cereal starch gelatinization .
- the oxidation step affects the gelatini- zation properties of cereal starch modifying its past ⁇ ing properties.
- the method according to the present invention it is possible to modify the properties of cereal starch simultaneously with de ⁇ grading the gluten proteins present therein.
- the acidic pH affects the radical attack, resulting from the oxidative treatment, on the cereal starch fraction.
- the peptides formed in step a) are flavor enhancing and/or bioactive.
- step a) is performed at a temperature of 5 - 50 °C .
- step a) is allowed to continue until the content of gluten proteins in the cereal starch fraction is at most 100 ppm, preferably at most 20 ppm. In one embod- iment of the present invention step a) is allowed to continue for up to 50 hours. In one embodiment of the present invention step a) is allowed to continue for 1 - 50 hours, preferably 1 - 4 hours.
- step a) is stopped by adding at least one chelating agent. In one embodiment of the present invention step a) is stopped by adding ethylenediaminetetraacetic ac ⁇ id (EDTA) .
- EDTA ethylenediaminetetraacetic ac ⁇ id
- the present invention further relates to a cereal starch fraction obtainable by the method ac- cording to the present invention.
- the present invention further relates to a food ingredient comprising the cereal starch fraction according to the present invention.
- the present invention further relates to a food product produced using the cereal starch fraction according to the present invention.
- the present invention further relates to the use of the method according to the present invention for providing a gluten-free cereal starch fraction.
- the present invention further relates to the use of the method according to the present invention for providing flavour enhancing and/or bioactive peptides .
- the method according to the present invention can be used for removing gluten proteins from a cereal starch fraction.
- the removal of the gluten proteins can be carried out by degrading the gluten proteins into peptides.
- the method according to the pre ⁇ sent invention can result in gluten proteins being degraded into peptides which can be flavour enhancing and/or bioactive. I.e. simultaneously with reducing the gluten content level of the cereal starch fraction beneficial, e.g. bioactive, peptides are being formed.
- the method according to the present invention can be used in order to produce food that meets the requirements for gluten-free standards.
- the cereal starch fraction obtained by the present invention can be consumed by persons having gluten sensitivity.
- Fibre products, baked products, and beer can be mentioned as examples of such food products.
- a method, a cereal composition, a food ingredient, a food or a use, to which the invention is related, may comprise at least one of the embodiments of the inven ⁇ tion described hereinbefore.
- An advantage of the method according to the present invention is that gluten proteins in a cereal starch fraction, i.e. plant storage proteins, can be degraded such that the cereal starch fraction treated is suitable to be used by e.g. a person suffering from celiac disease.
- An advantage of the obtained cereal starch fraction is that it is tolerated by a person being gluten intolerant or gluten sensitive.
- An advantage of the present invention is that it provides an effective, low cost, and gentle method to be used for degrading gluten proteins in a cereal starch fraction without any need for e.g. thermal in- activation as the reaction can end when the compounds, e.g. oxidizing agent and catalyzing agent, for the re- action are consumed.
- An advantage of the present invention is that it is possible to produce e.g. cereal starch, having reduced or eliminated content of gluten proteins.
- An advantage of the present invention is that when gluten proteins present in a cereal starch frac ⁇ tion are degraded by the method according to the pre ⁇ sent invention small peptides that can act as flavor precursors or health beneficial bioactive peptides are produced .
- the present invention has an advantage of providing a new method for the production of gluten- free foods .
- the pasting property of the oxidized barley starch was analyzed by Rapid Visco Analyser (Newport Scientific RVA-4) .
- the reaction mixture was stirred and heated, causing the barley starch to gelatinize and to form a paste.
- the treatment caused breakdown of residual gluten proteins present in the barley starch.
- the deg- radation of the gluten proteins, or prolamins, of the treated barley starch was confirmed by Western blot analysis.
- the analysis of the barley starch with the R5 ELISA test indicated that the content of gluten proteins in the treated barley starch was below 3 ppm.
- the oxidative treatment is carried out by using an oxidizing agent, but the oxidation treatment could also had been initiated or boosted by other means such as by using e.g. homogeni- zation, heating or sonication, as will be obvious to a skilled person in light of this specification.
- the invention is not limited to using the aforementioned oxidative treatment in particular and the ad ⁇ vantages of the invention can be readily obtained by the skilled person in light of this specification also with the oxidative treatments mentioned above.
Abstract
The present invention relates to a method for reducing the content of gluten proteins in a cereal starch fraction, wherein gluten protein comprises proline, and wherein the method comprises the step of: a) subjecting the cereal starch fraction to an oxidative treatment for degrading the gluten proteins into peptides.
Description
A METHOD FOR REDUCING THE CONTENT OF GLUTEN PROTEINS IN A CEREAL FRACTION
FIELD OF THE INVENTION
The invention relates to a method for reduc¬ ing the content of gluten proteins in a cereal starch fraction, to a cereal starch fraction obtained by the method, and to the uses thereof. BACKGROUND OF THE INVENTION
Proline is an amino acid frequently occurring in the sequence of cereal storage proteins. Proline makes a polypeptide chain to turn in a tight helical structure packing it effectively in the storage pro- tein bodies of the seed. Prolamins are gluten proteins rich in proline, and in addition to their high proline content they are also rich in glutamine. Prolamins are characterized by their water-insolubility, but instead they are typically soluble in aqueous alcohol. The prolamins of three cereals, i.e. wheat, rye and bar¬ ley, which are also called Triticeae cereals, are con¬ sidered to contain sequences harmful to those having gluten intolerance or celiac disease.
Celiac disease, also referred to as gluten enteropathy or non-tropical sprue, is an autoimmune disorder of the small intestine that occurs in genet¬ ically predisposed people of all ages. The character¬ istic symptom of this disease is the damage of the ep¬ ithelium of small bowel and intolerance to wheat glu- ten. The products containing wheat proteins as well as barley and rye should be eliminated from the diet of people suffering from this disease.
The triggering peptide causing celiac disease still remains somewhat unclear. However, it has been known that the toxic sequence is present in prolamins
of some cereals, and that these proteins, which are generally called as gluten proteins, are characterised by a high content of proline amino acid.
By degrading the harmful prolamins it is pos¬ sible to decrease or even eliminate their toxicity and to produce products or ingredients, which can safely be used by persons being gluten intolerants. Prior art recognizes the use of enzymes for the hydrolysis or degradation of prolamins or gluten proteins. However, the use of enzymes has the drawback of being expensive to use in this kind of process.
The inventors have recognized a need for an effective method for reducing the content of gluten proteins in a cereal starch fraction in a non- enzymatic manner.
PURPOSE OF THE INVENTION
The purpose of the invention is to provide a new type of method for reducing the content of gluten proteins in a cereal starch fraction, and to provide a cereal starch fraction with reduced gluten content for different applications.
SUMMARY
The method according to the present invention is characterized by what is presented in claim 1.
The cereal starch fraction according to the present invention is characterized by what is present¬ ed in claim 10.
The food ingredient according to the present invention is characterized by what is presented in claim 11.
The food product according to the present in¬ vention is characterized by what is presented in claim
The use according to the present invention is characterized by what is presented in claim 13.
BRIEF DESCRIPTION OF THE DRAWINGS
The accompanying drawing, which is included to provide a further understanding of the invention and constitutes a part of this specification, illus¬ trates one embodiment of the invention and together with the description helps to explain the principles of the invention. In the drawing:
Fig. 1 shows pasting properties of barley starch oxidized by Cu2+/H202 at pH 4.5 and 7.4 as ana¬ lyzed by rapid visco analyser (RVA) . The control was native barley starch.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a method for reducing the content of gluten proteins in a cereal fraction, wherein gluten protein comprises proline, and wherein the method comprises the step of: a) sub¬ jecting the cereal fraction to an oxidative treatment for degrading the gluten proteins into peptides.
The present invention relates to a method for reducing the content of gluten proteins in a cereal starch fraction, wherein gluten protein comprises proline, and wherein the method comprises the step of: a) subjecting the cereal starch fraction to an oxidative treatment for degrading the gluten proteins into pep¬ tides .
The expression "gluten proteins" or any corresponding expression should be understood in this specification, unless otherwise stated, as proteins found in cereal that are considered to be harmful to a person with celiac disease and/or an intolerance to gluten. In one embodiment of the present invention the gluten proteins are cereal prolamins and/or glutelins
found in the Triticeae cereals, i.e. in wheat, rye and barley. The prolamins of these cereals in particular are considered to contain protein sequences harmful to those having gluten intolerance or celiac disease. These prolamins include gliadin, which can be found in wheat, hordein which can be found in barley, and se- calin, which can be found in rye.
The expression "cereal fraction" or any corresponding expression should be understood in this specification, unless otherwise stated, as any suita¬ ble fraction of cereal that can be used in the method according to the present invention.
In one embodiment of the present invention step a) is carried out in an aqueous suspension.
The cereal fraction used in the present in¬ vention is a cereal starch fraction. In one embodiment of the present invention the cereal starch frac¬ tion comprises wheat, rye, barley, oat, or any combi¬ nation thereof. In one embodiment of the present in- vention the cereal starch is selected from a group consisting of wheat starch, rye starch, barley starch, and any combination thereof. In one embodiment of the present invention the cereal starch fraction comprises wheat, rye, barley, or any combination thereof.
In one embodiment of the present invention step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to at least one oxidizing agent. In one embodiment of the present invention step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch frac¬ tion to the presence of at least one oxidizing agent. In one embodiment of the present invention the at least one oxidizing agent is selected from a group consisting of hydrogen peroxide, ascorbic acid, tita¬ nium oxide, and any combination thereof.
In one embodiment of the present invention step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to heat, shear forces, homogenisation, sonication, or to any combination thereof. Such treatments can also be used to control structural proper¬ ties, e.g. viscosity and sliminess of polysaccharides, of the cereal starch fraction while at the same time promoting gelling properties of polysaccharide frag- ments.
In one embodiment of the present invention step a) of subjecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch fraction to heat, shear forces, homogenisation, sonication, or to any combination thereof before, simultaneously and/or after subjecting the cereal starch fraction to at least one oxidizing agent.
The inventors surprisingly found out that the content of gluten proteins could be reduced in a cere- al starch fraction by using an oxidizing treatment. Without limiting the invention to any specific theory about why the method of the present invention results in this advantage, it is to be considered that the ox¬ idizing treatment affects proline present in the amino acid sequence of gluten proteins. The bond between proline and an adjacent amino acid in the amino acid sequence is cleaved resulting in the gluten protein being degraded. The degradation of the gluten proteins results in smaller peptides being formed. The formed peptides are found to be bioactive and potentially health promoting and/or flavouring agents, and are not harmful to persons suffering from celiac disease or to individuals being gluten intolerants. The advantage of the method according to the present invention is that the cereal starch fraction can be treated such that it can be consumed by persons suffering from celiac dis¬ ease or being gluten intolerants. The degradation of
gluten proteins can result in the release of bioactive peptides that can have health promoting effects such as controlling blood pressure. The method according to the present invention can be applied for modifying ce- real gluten proteins, also called as cereal prolamin proteins, like wheat gliadin and barley hordein.
In one embodiment of the present invention the molar mass of the resulting peptide is less than 4000 Da, preferably less than 2000 Da, and more pref- erably less than 1000 Da.
In one embodiment of the present invention step a) comprises subjecting the cereal starch frac¬ tion to an oxidative treatment in the presence of at least one catalyzing agent, wherein the catalyzing agent comprises metal and/or transition metal. In one embodiment of the present invention the catalyzing agent comprises copper and/or iron. In one embodiment of the present invention the catalyzing agent compris¬ es Cu(II) and/or Fe(II).
When using at least one catalyzing agent in step a) together with at least one oxidizing agent, e.g. hydrogen peroxide, a so-called Fenton-type metal catalyzed oxidation reaction can take place, e.g. in the following manner:
Cu+/Fe2+ + H202→ ·ΟΗ + OH" + Cu2+/Fe3+
AH2 + 2Cu2+/Fe3+→ A + 2H+ + 2Cu+/Fe2+
AH2 + 02→ A + H202 The use of the at least one catalysing agent will speed up the reactions taking place in step a) .
In one embodiment of the present invention the method comprises adjusting the pH in step a) to a value of 3 - 7, preferably 4 - 5, and more preferably to about 4,5. In one embodiment of the present inven¬ tion the method comprises adjusting the pH in step a) for modifying the properties of the cereal starch
fraction. The pH can be adjusted in step a) such that e.g. cereal starch being treated, is simultaneously gelatinized. The degradation or cleavage of gluten proteins or prolamins was found to be efficient at an acidic pH, and especially at a pH of 3 - 6. Further, it was surprisingly found out that when using acidic pH conditions in step a) , the oxidative treatment has no effect on cereal starch gelatinization . When using a neutral pH, the oxidation step affects the gelatini- zation properties of cereal starch modifying its past¬ ing properties. By the use of the method according to the present invention it is possible to modify the properties of cereal starch simultaneously with de¬ grading the gluten proteins present therein. Without limiting the invention to any specific theory about why the method of the present invention results in the aforementioned advantage, it is to be considered that the acidic pH affects the radical attack, resulting from the oxidative treatment, on the cereal starch fraction.
In one embodiment of the present invention the peptides formed in step a) are flavor enhancing and/or bioactive.
In one embodiment of the present invention step a) is performed at a temperature of 5 - 50 °C .
In one embodiment of the present invention step a) is allowed to continue until the content of gluten proteins in the cereal starch fraction is at most 100 ppm, preferably at most 20 ppm. In one embod- iment of the present invention step a) is allowed to continue for up to 50 hours. In one embodiment of the present invention step a) is allowed to continue for 1 - 50 hours, preferably 1 - 4 hours.
In one embodiment of the present invention step a) is stopped by adding at least one chelating agent. In one embodiment of the present invention step
a) is stopped by adding ethylenediaminetetraacetic ac¬ id (EDTA) .
The inventors surprisingly found out that by the method according to the present invention it is possible to reduce the gluten proteins content of a cereal composition. Especially it was found out that the content of gluten proteins in cereal starch could be reduced by the oxidative treatment according to the present invention such that the cereal starch is suit- able to be used by persons suffering from celiac dis¬ ease or being gluten intolerants. It was surprisingly found out that by subjecting a cereal starch fraction, such as cereal starch fraction, to e.g. an oxidizing agent in accordance with the present invention the gluten proteins present therein were degraded while maintaining the desired properties of the cereal starch fraction. Degradation of the gluten proteins results in the toxic effects of gluten being removed from the cereal starch fraction. It was found out that the method according to the present invention affected the properties of the treated cereal starch fraction in a desired manner.
The present invention further relates to a cereal starch fraction obtainable by the method ac- cording to the present invention.
The present invention further relates to a food ingredient comprising the cereal starch fraction according to the present invention.
The present invention further relates to a food product produced using the cereal starch fraction according to the present invention.
The present invention further relates to the use of the method according to the present invention for providing a gluten-free cereal starch fraction.
The present invention further relates to the use of the method according to the present invention
for providing flavour enhancing and/or bioactive peptides .
The method according to the present invention can be used for removing gluten proteins from a cereal starch fraction. The removal of the gluten proteins can be carried out by degrading the gluten proteins into peptides. Thus, the method according to the pre¬ sent invention can result in gluten proteins being degraded into peptides which can be flavour enhancing and/or bioactive. I.e. simultaneously with reducing the gluten content level of the cereal starch fraction beneficial, e.g. bioactive, peptides are being formed.
The method according to the present invention can be used in order to produce food that meets the requirements for gluten-free standards. The cereal starch fraction obtained by the present invention can be consumed by persons having gluten sensitivity.
Fibre products, baked products, and beer can be mentioned as examples of such food products.
The embodiments of the invention described hereinbefore may be used in any combination with each other. Several of the embodiments may be combined to¬ gether to form a further embodiment of the invention. A method, a cereal composition, a food ingredient, a food or a use, to which the invention is related, may comprise at least one of the embodiments of the inven¬ tion described hereinbefore.
An advantage of the method according to the present invention is that gluten proteins in a cereal starch fraction, i.e. plant storage proteins, can be degraded such that the cereal starch fraction treated is suitable to be used by e.g. a person suffering from celiac disease. An advantage of the obtained cereal starch fraction is that it is tolerated by a person being gluten intolerant or gluten sensitive.
An advantage of the present invention is that it provides an effective, low cost, and gentle method
to be used for degrading gluten proteins in a cereal starch fraction without any need for e.g. thermal in- activation as the reaction can end when the compounds, e.g. oxidizing agent and catalyzing agent, for the re- action are consumed.
An advantage of the present invention is that it is possible to produce e.g. cereal starch, having reduced or eliminated content of gluten proteins.
An advantage of the present invention is that when gluten proteins present in a cereal starch frac¬ tion are degraded by the method according to the pre¬ sent invention small peptides that can act as flavor precursors or health beneficial bioactive peptides are produced .
The present invention has an advantage of providing a new method for the production of gluten- free foods .
EXAMPLES
Reference will now be made in detail to the embodiments of the present invention, an example of which is illustrated in the accompanying drawings.
The description below discloses some embodi¬ ments of the invention in such a detail that a person skilled in the art is able to utilize the invention based on the disclosure. Not all steps of the embodi¬ ments are discussed in detail, as many of the steps will be obvious for the person skilled in the art based on this specification.
EXAMPLE 1 - Oxidation of a wheat starch fraction with hydrogen peroxide catalyzed by copper
In this example 2 mg/ml of wheat starch was incubated in the presence of 0.05 mM CuS04 and 5 mM hydrogen peroxide at pH 4.5. The incubation tempera¬ ture was 37 °C. The reaction was stopped by 1 mM EDTA.
The gliadin content of the wheat starch frac¬ tion was determined by using a SDS-PAGE gel. From the results it could be seen that the treatment caused breakdown of gliadin present in the wheat starch frac- tion. With a longer incubation time the degradation of gliadin went further. The gliadin was almost totally degraded after eight hours of incubation, and totally degraded after 24 hours of incubation. EXAMPLE 2 - Oxidation of a barley starch fraction by a copper catalyzed hydrogen peroxide induced reaction
In this example 3 g of barley starch was in¬ cubated in 25 ml of 0.1 M phosphate buffer with the presence of 0.05 mM CuS04 and 5 mM hydrogen peroxide at pH values of 4.5 and 7.4. The incubation tempera¬ ture was 37 °C. After 4 hours the reaction was stopped by adding catalase.
The pasting property of the oxidized barley starch was analyzed by Rapid Visco Analyser (Newport Scientific RVA-4) . The reaction mixture was stirred and heated, causing the barley starch to gelatinize and to form a paste.
Oxidation of the barley starch at pH 7.4 re- suited in a decrease of its final viscosity, while at pH 4.5 the final viscosity was comparable to native starch. The results are presented in Fig. 1.
The treatment caused breakdown of residual gluten proteins present in the barley starch. The deg- radation of the gluten proteins, or prolamins, of the treated barley starch was confirmed by Western blot analysis. The analysis of the barley starch with the R5 ELISA test indicated that the content of gluten proteins in the treated barley starch was below 3 ppm.
In the example above the oxidative treatment is carried out by using an oxidizing agent, but the oxidation treatment could also had been initiated or boosted by other means such as by using e.g. homogeni- zation, heating or sonication, as will be obvious to a skilled person in light of this specification. Thus, the invention is not limited to using the aforementioned oxidative treatment in particular and the ad¬ vantages of the invention can be readily obtained by the skilled person in light of this specification also with the oxidative treatments mentioned above.
It is obvious to a person skilled in the art that with the advancement of technology, the basic idea of the invention may be implemented in various ways. The invention and its embodiments are thus not limited to the examples described above; instead they may vary within the scope of the claims.
Claims
1. A method for reducing the content of glu¬ ten proteins in a cereal starch fraction, wherein gluten protein comprises proline, c h a r a c t e r i z e d in that the method comprises the step of:
a) subjecting the cereal starch fraction to an oxidative treatment for degrading the gluten pro¬ teins into peptides.
2. The method according to claim 1, c h a r - a c t e r i z e d in that the cereal starch is selected from a group consisting of wheat starch, rye starch, barley starch, and any combination thereof.
3. The method according to -claim 1, c h a r a c t e r i z e d in that the cereal starch frac- tion comprises wheat, rye, barley, oat, or any combi¬ nation thereof.
4. The method according to any one of claims 1 - 3, c h a r a c t e r i z e d in that step a) of sub¬ jecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch frac¬ tion to the presence of at least one oxidizing agent.
5. The method according to claim 4, c h a r a c t e r i z e d in that the at least one oxidizing agent is selected from a group consisting of hydrogen peroxide, ascorbic acid, titanium oxide, and any com¬ bination thereof.
6. The method according to any one of claims 1 - 3, c h a r a c t e r i z e d in that step a) of sub¬ jecting the cereal starch fraction to an oxidative treatment comprises subjecting the cereal starch frac¬ tion to heat, shear forces, homogenisation, sonication, or to any combination thereof.
7. The method according to any one of claims 1 - 6, c h a r a c t e r i z e d in that step a) compris- es subjecting the cereal starch fraction to an oxidative treatment in the presence of at least one cata-
lyzing agent, wherein the catalyzing agent comprises metal and/or transition metal.
8. The method according to claim 7, c h a r a c t e r i z e d in that the catalyzing agent comprises copper and/or iron.
9. The method according to any one of claims 1 - 8, c h a r a c t e r i z e d in that the method com¬ prises adjusting the pH in step a) to a value of 3 - 7, preferably 4 - 5, and more preferably to about 4,5.
10. A cereal starch fraction obtainable by the method according to any one of claims 1 - 9.
11. Food ingredient comprising the cereal starch fraction of claim 10.
12. Food product produced using the cereal starch fraction of claim 10.
13. Use of the method according to any one of claims 1 - 9 for providing a gluten-free cereal starch fraction .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13829706.4A EP2884854A4 (en) | 2012-08-14 | 2013-08-13 | A method for reducing the content of gluten proteins in a cereal fraction |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20125841A FI125288B (en) | 2012-08-14 | 2012-08-14 | A method for reducing the gluten protein content of a cereal fraction |
| FI20125841 | 2012-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014027139A1 true WO2014027139A1 (en) | 2014-02-20 |
Family
ID=50101270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FI2013/050796 WO2014027139A1 (en) | 2012-08-14 | 2013-08-13 | A method for reducing the content of gluten proteins in a cereal fraction |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2884854A4 (en) |
| FI (1) | FI125288B (en) |
| WO (1) | WO2014027139A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016156009A1 (en) | 2015-03-30 | 2016-10-06 | Ambiente E Nutrizione S.R.L. | Process for the oxidation of starch-based materials |
| WO2016210408A1 (en) | 2015-06-25 | 2016-12-29 | Manildra Milling Corporation | Gluten-free starch and methods of producing same |
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| GB182829A (en) * | 1921-01-11 | 1922-07-11 | Frederick Harper Campbell | Manufacture of starch |
| GB300515A (en) * | 1927-05-12 | 1928-11-12 | Noury & Van Der Lande S Handel | A process for manufacturing a flour improver and products treated therewith |
| US3085014A (en) * | 1959-06-23 | 1963-04-09 | Herbert O Renner | Methods for oxidatively treating flour |
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| US3901725A (en) * | 1971-09-15 | 1975-08-26 | Staley Mfg Co A E | Size classified cereal starch granules |
| US5833755A (en) * | 1996-03-25 | 1998-11-10 | National Starch And Chemical Investment Holding Corporation | Starch degradation using metal-based coordination complexes |
| SE526999C2 (en) * | 2001-02-26 | 2005-12-06 | Biovelop Internat Bv | Process for extracting cell wall components and less accessible cereal clay proteins substantially free of soluble compounds |
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-
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- 2013-08-13 EP EP13829706.4A patent/EP2884854A4/en not_active Withdrawn
- 2013-08-13 WO PCT/FI2013/050796 patent/WO2014027139A1/en active Application Filing
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| GB182829A (en) * | 1921-01-11 | 1922-07-11 | Frederick Harper Campbell | Manufacture of starch |
| GB300515A (en) * | 1927-05-12 | 1928-11-12 | Noury & Van Der Lande S Handel | A process for manufacturing a flour improver and products treated therewith |
| US3085014A (en) * | 1959-06-23 | 1963-04-09 | Herbert O Renner | Methods for oxidatively treating flour |
| EP0282038A1 (en) * | 1987-03-12 | 1988-09-14 | Nisshin Flour Milling Co., Ltd. | New modified gluten product and bread improver composition |
| EP0301278A2 (en) * | 1987-07-27 | 1989-02-01 | Katayama Chemical Works Co., Ltd. | A particle-dispersing agent |
| US5274079A (en) * | 1987-07-27 | 1993-12-28 | Katayama Chemical Works Co., Ltd. | Protein partial degradation products that are useful as surface active agents and dispersing agents |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016156009A1 (en) | 2015-03-30 | 2016-10-06 | Ambiente E Nutrizione S.R.L. | Process for the oxidation of starch-based materials |
| CN107667122A (en) * | 2015-03-30 | 2018-02-06 | 安宾特营养食品有限责任公司 | The method for aoxidizing the material based on starch |
| WO2016210408A1 (en) | 2015-06-25 | 2016-12-29 | Manildra Milling Corporation | Gluten-free starch and methods of producing same |
| US11730179B2 (en) | 2015-06-25 | 2023-08-22 | Manildra Milling Corporation | Gluten-free starch and methods of producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FI125288B (en) | 2015-08-14 |
| EP2884854A1 (en) | 2015-06-24 |
| EP2884854A4 (en) | 2016-03-09 |
| FI20125841A (en) | 2014-02-15 |
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