WO2010066661A1 - Procédé de préparation d'un agent à l'arôme de viande - Google Patents

Procédé de préparation d'un agent à l'arôme de viande Download PDF

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Publication number
WO2010066661A1
WO2010066661A1 PCT/EP2009/066481 EP2009066481W WO2010066661A1 WO 2010066661 A1 WO2010066661 A1 WO 2010066661A1 EP 2009066481 W EP2009066481 W EP 2009066481W WO 2010066661 A1 WO2010066661 A1 WO 2010066661A1
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WO
WIPO (PCT)
Prior art keywords
cysteine
source
process according
hydrogen sulfide
flavouring agent
Prior art date
Application number
PCT/EP2009/066481
Other languages
English (en)
Inventor
Christoph Hendrik Beckmann
Leon Marcel Van Der Blom
Sara Isabel Da Fonseca Selgas Martins Van Der Maaten
Amir Maximiliaan Batenburg
Original Assignee
Unilever Nv
Unilever Plc
Hindustan Unilever Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Nv, Unilever Plc, Hindustan Unilever Limited filed Critical Unilever Nv
Publication of WO2010066661A1 publication Critical patent/WO2010066661A1/fr

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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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/26—Meat flavours
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/201—Compounds of unspecified constitution characterised by the chemical reaction for their preparation
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning

Definitions

  • the invention relates to the preparation of a meat flavouring agent, in particular a process to prepare a meat flavouring agent using lyases.
  • the characterising taste of meats like chicken, beef, and pork is for an important part due to certain volatile sulphur-containing substances such as volatile thiols.
  • meat is relatively costly, many processed food products do not contain sufficient meat to provide a desirable meaty taste. This is easily solved by adding artificial meat flavours to such food products. For example, soups, sauces, bouillons often contain added flavouring agents to boost the meaty notes.
  • Flavouring agents with a meaty note are known in the art.
  • US 5 747 302 discloses a process to prepare flavouring ingredients to add a meaty taste to food products.
  • Starting point for this process are specific cysteine precursors like cysteine-benzyl aldehyde, and certain cysteine furfural complexes like 2- (2-furyl) -1, 3- thiazolidine-4-carboxylic acid.
  • Bakers yeast Sacharomyces cervisiae
  • is incubated in a medium containing these specific cysteine complexes e.g.
  • WO98/42208 discloses another way of adding a meat flavour to a food composition by adding flavour precursors to food which upon heating generate the flavour.
  • flavour precursors disclosed are cysteine hydrochloride and 4- methoxy-2,5 dimethyl-3 (2H) -furanone used in a weight ratio of 4 to 1, spray dried on a carrier of modified starch and gum acacia. The spray dried powder is then added as a flavouring agent to a food product. Upon heating the food product a meaty aroma is said to be generated.
  • the profile of the meat flavour is important. It would be desirable to provide a meat flavour whereby the meaty note is preferentially enhanced compared to the coffee note. Furthermore, traditionally prepared flavouring agents tend to be rather dark which limits the applications in some food products.
  • the present invention provides a process to prepare meat flavouring agents such as 2-methyl-3- furanthiol (MFT) and 2-furfurylthiol (FFT) which obviates the need to add artificial meaty flavouring agents or artificial precursors such as 2- (2-furyl) -1, 3-thiazolidine- 4-carboxylic acid and 4-methoxy-2, 5 dimethyl-3 (2H) - furanone.
  • meat flavouring agents such as 2-methyl-3- furanthiol (MFT) and 2-furfurylthiol (FFT)
  • MFT 2-methyl-3- furanthiol
  • FFT 2-furfurylthiol
  • Artificial precursors often need complicated synthesis which complicates production processes.
  • cysteine and natural precursors thereof may be used provided the process includes a step of hydrogen sulfide formation.
  • the present invention provides a process to prepare a meat flavouring agent whereby the meaty note is preferentially increased compared to the coffee note.
  • the inventive meat flavouring agents are
  • a process of preparing a meat flavouring agent comprising the steps of a) providing a source of cysteine selected from the free amino acid cysteine, a peptide, a hydrolysed protein, a partially hydrolysed protein preferably from vegetable or animal sources and mixtures thereof; b) forming an hydrogen sulfide-containing reaction mixture from said cysteine source by contacting said cysteine source with a suitable enzyme capable of generating hydrogen sulfide from cysteine; and c) heating the hydrogen sulfide containing reaction mixture formed in the previous step with at least one reducing carbohydrate source, and optionally at least one additional source of amino acid and/or peptide thereby generating a meat flavouring agent.
  • the inventive process is able to provide a meat flavouring agent whereby the meaty note is preferentially increased compared to the coffee note as defined by a preferential increase in the amount of MFT vs FFT in the meat flavouring agent.
  • MFT vs FFT preferential increase of MFT vs FFT when the percentage increase of MFT in the meat flavouring agent is higher than the percentage increase of FFT when compared to meat flavouring agent produced in the same process except that no enzyme was present .
  • a cysteine source is provided.
  • the source may be the free amino acid itself.
  • the cysteine source will include a peptide, a hydrolysed protein, a partially hydrolysed protein, and mixtures thereof.
  • the source will be vegetable or animal. Examples are (partially) hydrolysed whey protein, (partially) hydrolysed egg protein, (partially) hydrolysed soy protein, cystine, glutathione, oligo-peptides with about less than 10 amino acids, preferably oligo-peptides whereby the cysteine is in a terminal position.
  • the cysteine source is preferably such to provide a sufficient amount of hydrogen sulfide in the next step of the process.
  • the level of the cysteine source is preferably equivalent to an amount of from 0.045 mM to 200 mM of free cysteine, more preferably 0.045 mM to 80 mM, more preferably 0.045 mM to 60 mM, more preferably 0.1 mM to 50 mM, most preferably from 0.2 mM to 40 mM of free cysteine.
  • 0. ImM of cystine which is a di-peptide containing two cysteine molecules is equivalent to 0.2mM of free cysteine.
  • a second step of the process comprises forming a hydrogen sulfide-containing reaction mixture from said cysteine source by contacting said cysteine source with a suitable enzyme capable of generating hydrogen sulfide from cysteine.
  • a suitable class of enzymes includes at least one carbon-sulphur-lyase (EC 4.4) able to generate hydrogen sulfide from cysteine via elimination.
  • lyases include beta and gamma C-S lyases such as cystathionine beta-lyase (EC 4.4.1.8), cystathionine gamma-lyase (EC 4.4.1.1), cysteine lyase (EC 4.4.1.10) and methionine gamma-lyase (EC 4.4.1.11) and mixtures thereof. Lyases are well known in the art of cheese making to ferment milk.
  • Organisms producing lyases include Lactobacillus fermentum, L. easel. Lactococcus lactis , Lactobacillus helveticus , Lactobacillus casei, Brevibacterium linens and more specific references can be found in "Yvon and Rijnen, ⁇ Cheese flavour formation by amino acid catabolism' ,
  • lyase is obtainable from Lactobacillus fermentum such as L. fermentum L61 (deposited under nr CBS123838 at CBS, PO Box 85167,3508 AD Utrecht, The Netherlands) .
  • Formation of the hydrogen sulfide containing reaction mixture from cysteine may occur at a temperature of from 2 to 80 degrees C, preferably from 4 to 60 degrees C, more preferably of from 15 to 50 degrees C.
  • the pH may range from 3 to 9, preferably from 5 to 8.5 and most preferably from 6 to 8.3.
  • the formation of the hydrogen sulfide containing reaction mixture may be carried out as long as needed to obtain a sufficient amount of hydrogen sulfide for the next step.
  • the formation of hydrogen sulfide is preferably carried out for a period of between 5 min and 4h. It is preferred that the step of hydrogen sulphide formation avoids prolonged exposure to high temperatures. Preferably, it is carried out at most 70 degrees C, more preferably at most 50 degrees C, more preferably at most 45 degrees C and preferably at least 10 degrees C, more preferably at least 20 degrees C.
  • the formation of the hydrogen sulfide containing reaction mixture is preferably carried out in the presence of a coenzyme such as pyridoxal-5-phosphate .
  • a subsequent third step of the process comprises heating the hydrogen sulfide containing reaction mixture formed in the previous step with at least one reducing carbohydrate source, and optionally at least one additional source of amino acid and/or peptide, thereby generating a meat flavour.
  • the carbohydrate source may be a reducing sugar.
  • the carbohydrate source is preferably selected from free monosaccharide or partially hydrolysed polymeric carbohydrate containing a pentose, hexose or degradation products thereof.
  • Preferred hexoses include glucose, fructose, rhamnose and mixtures thereof.
  • Preferred pentoses include xylose, arabinose, ribose and mixtures thereof.
  • the reducing carbohydrate source is selected from free monosaccharide or partially hydrolysed polymeric carbohydrate containing glucose, fructose, rhamnose, xylose, arabinose, ribose and mixtures thereof.
  • the amount of carbohydrate source will preferably be equivalent to an amount of from 0.045 mM to 20OmM, preferably 0.045 to 4OmM, more preferably 0.1 to 8OmM, preferably 0.2 to 4OmM, preferably 0.1 mM to 30 mM, most preferably from 0.2 mM to 20 mM of carbohydrate source.
  • the carbohydrate source and cysteine source are present in equimolar amounts.
  • the at least one additional source of amino acid and/or peptide may be (partially) hydrolysed protein, the free amino acid glycine, glycine containing peptides and mixtures thereof.
  • the amount of the source of amino acid and/or peptides will usually be equivalent to 0.045 mM to 7 M of free glycine, more preferably 0.1 M to 4 M, most preferably from 0.4 mM to 1 M of free glycine.
  • Another additional source of amino acid and/or peptide is yeast extract.
  • This heating step is carried out at a temperature of from 45 to 200 degrees C, preferably from 60 to 160 degrees C, more preferably of from 75 to 130 degrees C.
  • the heating step is typically carried out for about 15 min at 180 0 C with correspondingly longer times at lower temperature - doubling of time for every 1OC drop, although this is not linear.
  • the heating step is carried out for about 10 min to 32 hours, preferably 1 to 4 hrs, more preferably 30 min to 8 hours.
  • the pH of the heating step is usually 8 or less, preferably between 3 and 8, more preferably between 5 and 7.5.
  • the meat flavour formed may comprise sulphur containing compounds like furanthiols, thiophenes and mixtures thereof. Preferably with a thiol group in the 3-position.
  • the meat flavour may comprise disulfide compounds formed by oxidation of furanthiols and furfuryl thiols, and combinations of thereof.
  • 2-Methyl-3-furanthiol (MFT), and furfuryl thiol (FFT) are especially preferred. MFT is associated with a meaty note whereas FFT is more often described as a coffee note.
  • a process of preparing a food product comprising the step of adding a meat flavouring agent obtainable according to a process as described above to a food product.
  • the amount of meat flavouring agent is at least 0.0001 wt%, preferably at least 0.001 wt%, more preferably at least 0.01 wt%, and preferably at most 10 wt%, more preferably at most 5 wt%, even more preferably at most 3 wt% by weight of the total food product.
  • the inventive meat flavouring agent may be used in any food product where a meat flavour is desired.
  • Preferred food products are selected from the group consisting of soup, bouillon, sauce, seasoning, sausage, meal, side dish, and mixtures thereof.
  • Preferred ranges will often be described in the following format: preferably at least xl, more preferably at least x2, even more preferably x3, preferably at most yl, more preferably at most y2, even more preferably at most y3, whereby xl ⁇ x2 ⁇ x3 ⁇ y3 ⁇ y2 ⁇ yl .
  • This format is meant to include the preferred ranges xl to yl, more preferably x2 to y2 and even more preferably x3 to y3 whereby the endpoints are included and also all subranges subsumed therein (e.g. xl to y3 and x3 to yl) .
  • preferred ranges are described as xl to yl, more preferably x2 to y2 and even more preferably x3 to y3
  • the endpoints are meant to be included and also all subranges subsumed therein (e.g. xl to y3 and x3 to yl) .
  • all open ended ranges are meant to be included: preferably at least xl, more preferably at least x2, even more preferably x3, preferably at most yl, more preferably at most y2, even more preferably at most y3.
  • Lactobacillus fermentum L61 was grown overnight (2% inoculum) on MRS broth supplemented with 0.025% L- methionine at 37 degree C. Cells were harvested and washed twice with with 20 mM potassium phosphate buffer (pH 7.2) containing ImM EDTA, O.OlmM pyridoxal-5-phosphate and ImM phenylmethylsulfonyl fluoride. The cells were re-suspended in a minimum amount of the same buffer and disrupted with ultrasonic waves 30 cycles of 30 seconds sonication and 30 seconds of cooling on ice) . After sonication the suspension was centrifuged at 15000 rpm to remove the cell debris and the obtained cell free extract was stored at -80 C until further use.
  • Example 2 Hydrogen sulfide formation from 0.5mM cysteine with carbon-sulphur lyase compared to thermal decomposition
  • Hydrogen sulfide formation was compared between one process whereby hydrogen sulfide was formed from cysteine by thermal decomposition (in absence of carbon-sulphur lyase) and another process with carbon-sulphur lyase according to the invention.
  • the conditions for thermal decomposition were 0.5 mM cysteine in 0. IM phosphate buffer pH 8 for Ih at 100 0 C.
  • the process with carbon-sulphur lyase was carried out at 30 0 C, using 0.5 mM cysteine in 0. IM phosphate buffer pH 8 in the presence of 1 ml carbon-sulphur lyase extract as prepared in example 1 and O.OlmM pyridoxal-5-phosphate (PLP) .
  • Example 3 Hydrogen sulfide formation from 10 mM cysteine with carbon-sulphur lyase compared to thermal decomposition As example 2, except that the cysteine initial concentration was 1OmM.
  • Example 4 Hydrogen sulfide formation from 3OmM cysteine with carbon-sulphur lyase compared to thermal decomposition
  • Example 5 Process to prepare meat flavouring agents from cysteine in the presence of lyase: preferential increase in MFT vs FFT 1 ml of cell free extract as prepared in Example 1 was added to 10 mL phosphate buffer (100 mM, pH 8) containing O.OlmM pyridoxal-5-phosphate (PLP), 30 mM cysteine, 30 mM xylose and 0.67 M glycine was prepared. This solution was incubated for 30 minutes at 30 0 C and hydrogen sulfide formation was monitored by PTR-MS. After that period, the mixture was heated for 2.5h at 100 0 C. Identical samples were prepared except that no enzyme was present.
  • PDP O.OlmM pyridoxal-5-phosphate
  • MFT 2-methyl-3-furanthiol
  • FFT 2- furfurylthiol
  • the resulting preparation had a clear fresh meaty note, in particular fresh roasted beef flavour, clearly intensified in the preparation where the enzyme was used.
  • the results showed that the process according to the invention provided a meat flavouring agent with a preferential increase in meaty notes (MFT) over coffee notes (FFT) .
  • Example 6 Process to prepare meat flavouring agents from cysteine in the presence of lyase: preferential increase in MFT vs FFT.
  • Example 2 1 ml of cell free extract as prepared in Example 1 was added to 5 mL phosphate buffer (100 mM, pH 8) containing 60 mM cysteine and O.OlmM pyridoxal-5-phosphate (PLP) . This solution was incubated for 120 minutes at 30 0 C. After the incubation, the product was mixed 1:1 by volume with a mixture of xylose and glycine in 100 mM phosphate buffer to obtain concentrations 30 mM xylose and 0.67 M glycine. This mixture was heated for 120 min at 100 0 C at pH 6. Identical samples were prepared except that no enzyme was present in first incubation at 30 0 C. The increase of MFT vs FFT was compared between the non-enzymatic route and the enzymatic process according to the invention, using the analytical methodology described in example 5.
  • PDP O.OlmM pyridoxal-5-phosphate
  • the inventive meat flavouring agent was diluted to the same MFT level found in the non-enzymatic prepared meat flavouring agent.
  • the results showed the meat flavouring agent prepared according to the invention had a lighter colour than the meat flavouring agent prepared without enzyme. This was confirmed by measuring the absorbance (OD 420nm) .
  • Example 7 Process to prepare meat flavouring agents from cysteine in the presence of lyase: preferential increase in MFT vs FFT.
  • Example 6 was repeated except that the concentrations of cysteine, xylose and glycine were halved, i.e. 30 mM cysteine, 15 mM xylose and 0.33 M glycine.
  • the increase of MFT vs FFT was compared between the non-enzymatic route and the enzymatic process according to the invention.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Meat, Egg Or Seafood Products (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un agent à l'arôme de viande. Le procédé comprend les étapes consistant a) à utiliser une source de cystéine choisie dans le groupe consistant en cystéine d'acide aminé libre, peptide, protéine hydrolysée, protéine partiellement hydrolysée de préférence d'origine végétale ou animale et des mélanges de ceux-ci; b) à former un mélange réactionnel contenant du sulfure d'hydrogène à partir de ladite source de cystéine par la mise en contact de ladite source de cystéine avec une enzyme adaptée capable de générer du sulfure d'hydrogène à partir de la cystéine; et c) à chauffer le sulfure d'hydrogène contenant un mélange réactionnel formé à l'étape précédente avec au moins une source de glucide réducteur et, facultativement, au moins une source supplémentaire d'acide aminé et/ou de peptide, ce qui donne un agent à l'arôme de viande.
PCT/EP2009/066481 2008-12-10 2009-12-07 Procédé de préparation d'un agent à l'arôme de viande WO2010066661A1 (fr)

Applications Claiming Priority (2)

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EP08171184 2008-12-10
EP08171184.8 2008-12-10

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102894335A (zh) * 2012-11-07 2013-01-30 成都大帝汉克生物科技有限公司 一种具有豆瓣酱香的香精及其制备方法
CN103960458A (zh) * 2014-05-12 2014-08-06 江南大学 一种控制大豆蛋白贮藏过程中溶解度下降的方法
CN109306332A (zh) * 2018-09-22 2019-02-05 南京农业大学 发酵乳杆菌cd110及其在发酵香肠制备中的应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2934437A (en) * 1955-04-07 1960-04-26 Lever Brothers Ltd Flavoring substances and their preparation
EP0160794A1 (fr) * 1984-04-16 1985-11-13 Societe Des Produits Nestle S.A. Arômes de poulet et leur procédé de préparation
EP0277688A2 (fr) * 1987-01-30 1988-08-10 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé pour préparer des thiols
EP0770686A1 (fr) * 1995-10-25 1997-05-02 Societe Des Produits Nestle S.A. Procédé de préparation de thiols

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2934437A (en) * 1955-04-07 1960-04-26 Lever Brothers Ltd Flavoring substances and their preparation
EP0160794A1 (fr) * 1984-04-16 1985-11-13 Societe Des Produits Nestle S.A. Arômes de poulet et leur procédé de préparation
EP0277688A2 (fr) * 1987-01-30 1988-08-10 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Procédé pour préparer des thiols
EP0770686A1 (fr) * 1995-10-25 1997-05-02 Societe Des Produits Nestle S.A. Procédé de préparation de thiols

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102894335A (zh) * 2012-11-07 2013-01-30 成都大帝汉克生物科技有限公司 一种具有豆瓣酱香的香精及其制备方法
CN102894335B (zh) * 2012-11-07 2013-09-04 成都大帝汉克生物科技有限公司 一种具有豆瓣酱香的香精及其制备方法
CN103960458A (zh) * 2014-05-12 2014-08-06 江南大学 一种控制大豆蛋白贮藏过程中溶解度下降的方法
CN109306332A (zh) * 2018-09-22 2019-02-05 南京农业大学 发酵乳杆菌cd110及其在发酵香肠制备中的应用

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