JP2004215559A - Acrylamide production inhibitor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a safe acrylamide production inhibitor using an edible plant-derived component, excellent in the effect of inhibiting acrylamide production in processed food products ( including deep-fried food products ) with slight adverse effects such as offensive taste and odor on the processed food products ( including the deep-fried food products ). <P>SOLUTION: This acrylamide production inhibitor comprises as the active ingredient luteolin as a component found in perilla as a labiate, which is obtained preferably by extraction from the perilla as the labiate with a lower alcohol and water. <P>COPYRIGHT: (C)2004,JPO&NCIPI

Description

備考
ｎｄ：検出されず。
表中の（）内の数字は、検出限界の値を示した。
【００６３】
以上の結果、油脂に溶解する酸化防止剤（参考例３）は対照区（参考例４）の値より高い値が得られ、加熱時の熱と空気の暴露あるいはＢＨＴの揮発によって酸化防止剤の効果を失っている可能性が示唆された。一方、シソ抽出物に含まれる成分である試料１は対照区及び参考例１〜５に比べ、検出されないか（検出限界５０ｐｐｂ）、対照区の約１０分の１の値となり、本発明のルテオリンは食品のアクリルアミドの生成を有意に抑制することがわかった。また、配糖体から糖を分離しているナリンゲニンは対照区（参考例４）の値に比べ、半分（約５５％）の抑制効果を示した。そのため、フラボノイド化合物の構造式の違いによってアクリルアミドの生成量に影響を与えることが示唆された。さらに、フラボンを含めた上位概念にあたるポリフェノールの例として緑茶抽出物を利用した場合、油性食品の系ではアクリルアミドの生成を阻害しないことがわかった。
この結果は、フラボンを代表とするルテオリンに見られた顕著な効果である。そして本実施例で用いたルテオリンは高温加熱した油（非水）中でのアクリルアミド生成阻害剤、広くはアミノ・カルボニル反応を阻害する物質として作用することがわかった。
【図面の簡単な説明】
【図１】図１は、実施例１で得たルテオリンの吸収スペクトルを示す。
【図２】図２は、実施例１で得たルテオリンのＨＰＬＣクロマトグラムを示す。
【図３】図３は、実施例２で得たシソ実抽出濃縮液のＨＰＬＣクロマトグラムを示す。[0001]
[Industrial applications]
The present invention relates to an acrylamide formation inhibitor that can suppress acrylamide formation that occurs in a food cooking / processing step. More specifically, the present invention relates to a preparation containing luteolin as an active ingredient and suppressing acrylamide products in foods produced by using luteolin in food preparation and processing steps.
[0002]
[Prior art]
Conventionally, many methods have been studied in order to prevent a browning reaction of fried or fried cooked processed foods and the like. In particular, when frying processed foods such as starch, amino acids, foods containing oil or flour, the final food taste, flavor and color are affected by the browning reaction, and processed foods that emphasize the golden color The commercial value itself is affected by the browning reaction.
[0003]
Such a browning reaction is considered to be caused by an amino-carbonyl reaction. Specifically, as in ascorbic acid and glucose, the enediol structure (such as -C (OH) = C (OH)-) is quinonated (-CO = CO-) or aminated (- This is because the structure in which C (NHR) = C (NHR)-) is easily browned in the air. Oxidation occurs at each stage of the amino-carbonyl reaction, indicating that the final product is browning. Further, the browning reaction referred to in the present invention is a reaction in which an amino group (derived from asparagine or methionine) and a carbonyl group (derived from a reducing sugar) react at a high temperature at the stage of cooking a food to produce brown or black. In addition, coffee, bread, miso, and the like include a function of generating an aromatic component and imparting an appropriate baking color (Non-Patent Document 1).
[0004]
On the other hand, it has recently been reported that acrylamide, a highly carcinogenic substance, is produced from foods cooked at high temperatures, such as fried bread such as french fries and rusk, which has become a major problem in the food industry. I have.
[0005]
There have been few reports on the generation of acrylamide in fried foods, and recent reports on hazards such as carcinogenesis (Stockholm Report) (Non-Patent Documents 2 to 5). The cause of the production of acrylamide has already been published, and it has been reported that it is caused by the amino-carbonyl reaction due to the reaction between asparagine and glucose (Non-Patent Documents 6 and 7). There is an urgent need to consider substances to stop.
[0006]
It is known that acrylamide is not produced when food is boiled, but is produced when it is fried in oil or baked at a high temperature.
When inhibiting the amino-carbonyl reaction under conditions where water derived from vegetables and oil used are mixed, organic acids including vitamin C, vitamin E or citric acid are used to stop reactions such as oxidation and browning. It can easily be guessed that the combination use of anti-browning agents or antioxidants exhibits the effect of prevention, but under conditions where the oil is easily oxidized at high temperatures, the deterioration of the browning agent or the oxidation of the antioxidant itself is also rapid. It is difficult to expect the effect.
[0007]
In addition, fried foods cooked with oil such as french fries, potato chips, biscuits, fried chicken, French fries are provided in the form of processed foods and prepared dishes for business use such as the restaurant industry or to general consumers, or prepared dishes or prepared dishes. It is often used as a lunch box material, and appearance change due to amino-carbonyl reaction or browning reaction is an important problem to be solved in order to keep these commercial values high.
[0008]
Conventionally, browning includes browning due to an enzymatic reaction and browning due to a non-enzymatic reaction. Of the non-enzymatic browning reactions, the reaction that occurs between the amino compound and the reducing sugar and other carbonyl compounds is important, and this reaction is called the amino-carbonyl reaction. This reaction is also called a Maillard reaction. This reaction mechanism is divided into three stages, an initial stage, a middle stage, and a late stage. Among them, the initial stage shows the process from the formation of a nitrogen glycoside to the formation of an Amadori transfer compound by binding of an amino compound (such as an amino acid) and a carbonyl compound. The middle stage is a process from the decomposition of the enol form of the Amadori transfer compound to the formation of furfurals. In the latter stage, various compounds having a strong browning activity undergo a complicated reaction to form a high molecular color pigment (Non-Patent Document 8).
[0009]
The amino-carbonyl reaction involves amino compounds (amino acids, peptides, proteins, amines, etc.) and carbonyl compounds (sugars, decomposed sugars, compounds formed by oxidation of fats, etc.). Are divided into three groups: (2) those with ascorbic acid in the center, and (3) those with oil in the center. Although the reaction mechanism is various, at present, there is no definitive method for suppressing the aminocarbonyl reaction of food (Non-Patent Documents 9 to 11).
[0010]
Examples of the amino-carbonyl reaction (Maillard reaction) inhibitor include 3-hydroxy-4-aminomethylpyridine derivatives (Patent Document 1), cyclic α-hydroxyketone compounds (Patent Document 2), and 5-aminoalkyl-4. -Aminomethyl-3-hydroxypyridine derivative (Patent Literature 3), plant extract from carcade, hibiscus, chazensi, tonin, horse chestnut, syrup, gossypium, sicon, senna, toshishi, liquorice, or plantagoside, 5,7, 3 ', 4', 5'-Pentahydroxyflavanone (Patent Document 4) and the like are disclosed, and addition of these inhibitors to foods is also disclosed. However, these inhibitors involve proteins in vivo. It is an inhibitor of the Maillard reaction that occurs, preventing retinopathy, nephropathy, diabetic complications and other diseases and skin aging. A intended for the treatment, starch, amino acid, is not even any suggestion disclosed for inhibition of processed foods amino-carbonyl reaction in the case of frying, such as foods containing oil and flour.
[0011]
The problem of the amino-carbonyl reaction that occurs during cooking of food is when the food browns. Conventionally, methods for suppressing the browning reaction of such foods and methods for suppressing the browning reaction have relied on any one of (1) temperature and time control, and (2) the combined use of a browning reaction inhibitor, and combinations thereof. For example, the following method has been reported as a method for inhibiting a browning reaction by preventing oxidation.
[0012]
It is reported that the fatty acid composition of potato that easily produces acrylamide is 25% of saturated fatty acid, 5% of oleic acid, and 40% of linoleic acid, and is a foodstuff that is susceptible to deterioration by oxidation. In addition, the content of asparagine / aspartic acid contained in the potato is 0.82 g / 100 g, which is the second highest after glutamic acid, and indicates that the potato contains a large amount of a substance which causes the production of acrylamide. Therefore, in order to prevent browning of potato products, a combination of BHA, an antioxidant, and citric acid or propyl gallate (catechins) has been attempted to prevent oxidation at a stage prior to the browning reaction. It is said that the use amount of BHA is preferably 0.001 to 0.1%. However, in the case of fried food, BHA is easily volatilized, and at present, the expected effect is not obtained due to the volatility of the used antioxidant (Non-Patent Document 12).
[0013]
In addition, the antioxidant effect (prevention of browning) of potato flakes is being studied with quercetin, which contains onions and the like, but it has been reported that quercetin and caffeic acid should be used in combination, and that use of quercetin alone would be ineffective. (Non-Patent Document 13).
[0014]
It is also reported that potato flakes prevent sodium acid pyrophosphate from reacting with iron and prevent the color of potatoes from becoming black.However, it was reported that they were very effective in preventing oxidation or browning due to oxidation. Is not performed (Non-patent Document 14).
[0015]
When preparing starch-based foods, one or two kinds of antioxidants such as vitamin C and vitamin E, organic acids having a redox action such as citric acid and acetic acid, polymerized phosphates, alum and kojic acid, etc. Methods using combinations of more than one species have been proposed. However, there is a report that vitamin C has no remarkable browning reaction inhibitory effect, and there is a problem that the browning reaction inhibitory effect is lost when the used vitamin C is oxidized by air oxidation or the like. In addition, antioxidants other than those described above have a weak browning reaction inhibitory effect, or even if they have an effect, affect the taste, and are not necessarily preferable (Non-Patent Documents 15 and 16).
[0016]
Therefore, in order to inhibit the production of acrylamide in foods, investigations have been made in search of an acrylamide production inhibitor from a material that has experienced eating or a material derived from nature.
[0017]
Patent Literature 5 discloses a method for producing an edible oil, which uses linseed seeds, perilla seeds, perilla seeds, perilla seeds, evening primrose seeds, and borage seeds to produce an edible oil rich in linolenic acid. Focusing on the fatty acid portion, the use of antioxidant substances such as tocopherol, lecithin, and green tea extract in combination has led to discussions on the stability of plant seed oils and fats.
[0018]
Further, the use of a glycoside at the 7-position (cinaroside, Non-Patent Document 17) isolated from leaves of spring chrysanthemum and safflower as an antioxidant is being studied, but is not studied in oily foods. .
[0019]
Patent Document 6 considers an extract from a Labiatae plant as a deodorant. Ascorbic acid must be used in combination with a material containing a water-soluble extract as an active ingredient, and antioxidation must be left to the combination, and no inhibition of acrylamide formation during frying has been studied.
[0020]
Patent Document 7 discloses that the use of spices such as mustard, salmon and perilla in combination with polyphenolic compounds such as green tea extract and oolong tea extract in the roll material for fried foods prevents oil sickness during frying. However, there is no content that points out the relationship with acrylamide, and there is no use of perilla in the examples, and it is difficult to foresee the production of acrylamide because it has been studied. It was difficult to consider.
[0021]
As described above, no ingredient that suppresses the production of acrylamide during frying has been found from ingredients that have been eaten or ingredients that are derived from nature.
[0022]
In addition, when used in foods, the products themselves have no taste or odor so that they do not affect the original taste, flavor and color of the foods, and the products produced by the safety and heating of the foods used It is hoped that the safety of the building can be ensured.
[0023]
[Patent Document 1]
Japanese Patent Application Laid-Open No. 9-221473 [Patent Document 2]
JP-A-9-315960 [Patent Document 3]
JP-A-10-158244 [Patent Document 4]
JP-A-11-106336 [Patent Document 5]
JP 2000-316473 A [Patent Document 6]
JP-A-11-197222 [Patent Document 7]
Japanese Patent Application Laid-Open No. 2002-27933 [Non-Patent Document 1]
Toshiro Nakamura, Susumu Kimura, Hiromichi Kato: Discoloration of Food and Its Chemistry, Korin (1967), p. 291 [Non-Patent Document 2]
Swedish National Food Agency website http: // www. slv. se
[Non-Patent Document 3]
Rosen, J.A. & Hellenas, K.M. E. FIG. The Analyst 127 (2002) pp. 880-882 [Non-Patent Document 4]
WHO FAO / WHO Consultation on the Health Implications of Acrylamide in Foods (Geneva, 25-June 2002)
[Non-Patent Document 5]
IARC IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 60, (1994) p. 389 [Non-Patent Document 6]
D. S. Mototram, B .; L. Wedzicha, A .; T. Dodson, Nature, No. 419, 2002, pages 448-449 [Non-Patent Document 7]
R. H. Stadler, I .; Blank, N.M. Varga, F .; Robert, J. et al. Hau, P .; A. Guy, MC. Robert, S.M. Riediker, Nature, No. 419, (2002) p. 449 [Non-Patent Document 8]
Eiichi Tanikawa, Encyclopedia of Food Hygiene, Medical and Dental Medicine Publishing (1977), p. 122 [Non-Patent Document 9]
Toshiro Nakamura, Susumu Kimura, Hiromichi Kato: Discoloration of Food and Its Chemistry, Korin (1967) p.233 [Non-Patent Document 10]
Eiki Kamata, Osamu Katayama: Color of Food, Korin (1965), 108 pages [Non-Patent Document 11]
Yutaro Hosugai: Encyclopedia of Food Hygiene, Medical and Dental Medicine Publishing (1977), p. 21 [Non-Patent Document 12]
Shizuyuki Ota, Ed .: Foods and Antioxidants (1987), published by the Food Materials Research Association, 138 pages [Non-Patent Document 13]
Shizuyuki Ota, Ed .: Foods and Antioxidants (1987), published by the Food Materials Research Association, 227 pages [Non-patent Document 14]
Shizuyuki Ota, Ed .: Foods and Antioxidants (1987), Food Materials Research Association, 227 pages [Non-Patent Document 15]
Toshiro Nakamura, Susumu Kimura, Hiromichi Kato: Discoloration of Food and Its Chemistry, Korin (1967) p.233 [Non-Patent Document 16]
Ed. Fujimaki, M. et al .; Revised New Edition Food Chemistry (1976) Asakura Shoten, pp. 249-257 [Non-patent Document 17]
See Horhammer et al. , Acta Cim. Acad. Sci. Hung. 40, 4638 (1964)
[0024]
[Problems to be solved by the invention]
An object of the present invention is to provide an acrylamide formation inhibitor containing, as an active ingredient, an ingredient contained in a plant having experience in eating. More specifically, it is an object of the present invention to provide an acrylamide formation inhibitor which is safe and does not adversely affect the food to be treated in terms of color and odor. Furthermore, an object of the present invention is to provide a method for producing the acrylamide formation inhibitor, and a method for suppressing acrylamide formation in foods using the acrylamide formation inhibitor.
[0025]
[Means for Solving the Problems]
The present inventors have conducted intensive studies for solving the above problems, and found that luteolin, a kind of flavones contained in Lamiaceae plant perilla, has an excellent inhibitory effect on acrylamide formation in foods. I found it. In addition, the present inventors have found that a precursor of an extract prepared by extracting from a Labiatae plant perilla in the presence of a solvent such as a lower alcohol has the same effect.
[0026]
The present inventors have found that these precursors of luteolin and plant extract can be effectively used for acrylamide formation suppression treatment without giving any adverse effects such as color or odor to the food to be treated, and that the acrylamide formation Since deterioration of vegetables and processed foods (fruited foods) can be significantly prevented, it has been confirmed that it is extremely effective in suppressing acrylamide production and maintaining quality of processed foods (fried foods).
[0027]
The present invention has been completed based on such findings.
That is, the present invention is a food acrylamide formation inhibitor listed in the following (1) to (5):
(1) A food acrylamide formation inhibitor containing luteolin as an active ingredient.
(2) The acrylamide formation inhibitor according to (1), which is luteolin.
(3) The acrylamide production inhibitor according to (1) or (2), comprising luteolin of a Labiatae plant as an active ingredient.
(4) The acrylamide formation inhibitor according to (3), wherein luteolin of a Labiatae plant is derived from a water-soluble fraction of a Labiatae plant.
(5) The Lamiaceae plant is one or two or more species selected from perilla (blue perilla or red perilla), or spring chrysanthemum (Asteraceae), celery (Apiaceae), or bell pepper (Solanaceae). ) Or the acrylamide inhibitor according to (4).
(6) The acrylamide inhibitor according to (3) or (4), wherein the Lamiaceae plant is at least one member selected from perilla leaves or perilla seeds.
In addition, the present invention is a composition listed in the following (7), which is used for treating foods, regardless of the intended purpose or application such as suppression of acrylamide formation and quality retention:
(7) A food composition comprising the food acrylamide formation inhibitor according to any one of (1) to (6).
Further, the present invention relates to a method for suppressing acrylamide formation and a food product described in the following (8) to (9):
(8) A step of adhering the acrylamide production inhibitor for food according to any one of (1) to (6) or the composition for food according to claim 7 to oil at the time of frying or the surface of food. A method for suppressing the production of acrylamide in foods, including:
(9) A food treated with the acrylamide formation inhibitor for food according to any one of (1) to (6) or the food composition according to claim 7.
In the present invention, “acrylamide formation” refers to a reaction in which asparagine and glucose contained in vegetables such as potatoes cause an amino-carbonyl reaction (maillard reaction) to produce acrylamide when fried or fried vegetables. means. However, not limited to the reaction between asparagine and glucose, amino acids other than asparagine (for example, methionine, glutamine or cysteine) and sugars other than glucose (for example, amino carbonyl reaction processes such as fructose, galactose, lactose, sugar or butanedione) (The resulting intermediate substance) and an amino-carbonyl reaction to produce acrylamide.
[0028]
BEST MODE FOR CARRYING OUT THE INVENTION
The acrylamide formation inhibitor of the present invention is characterized by containing luteolin as an active ingredient. Luteolin is a flavones contained in perilla (Lamiacea perilla) leaves or fruits, spring chrysanthemums, celery, peppers, ginkgo leaves and safflowers. Its structural formula is 5,7,3 ', 4'-OH-Flavone. It has long been reported as an arabinose glycoside (Perkins, J. Chem. Soc. 69, 80 (1896)). Luteolin hydrate forms yellow needles when precipitated from alcohol. Glycosides are soluble in water and are yellow solutions in alkaline solutions (Merck Index 12th edition).
[0029]
Luteolin used in the present invention is classified as a flavonoid. Flavonoids are a general term for a group of phenyl compounds having a structure in which two benzene rings (rings A and B) are connected by three carbon atoms (diphenylpropane structure). The flavonoids are classified according to the structure of the C-ring attached to the moiety consisting of three carbon atoms. The flavone has one double bond in the C ring and has a carbonyl group at the 4-position of the C ring. Similarly, flavanone (naringenin) refers to a substance having no double bond in the C ring and having a carbonyl group at the 4-position of the C ring. A compound having a flavone skeleton. The skeleton may be modified with any functional group. For example, a sugar, preferably glucose, is bound to sinaloside (7-position glycoside), and garteolin (5-position glycoside) is included.
[0030]
The acrylamide formation inhibitor of the present invention only needs to contain luteolin as an active ingredient, and may contain a luteolin-containing fraction of a Labiatae plant.
[0031]
Here, as a Labiatae plant, for example, perilla (leaves, seeds, whole plants), sage, basil, rosemary, lavender, mannenrou, perilla, koganebana (ogon), hansilen, tobana, peppermint, oregano, thyme, salvia, There are marjoram, melissa and the like, and examples of plants containing luteonin include spring chrysanthemum, celery, peppers, ginkgo leaves, safflower leaves, safflower seeds and the like. The perilla plant is preferably perilla.
[0032]
Similarly, flavonoids (apigenin, chrysin, luteolin, baicalein, ougonin, baicalin, tangeretin), as well as flavonols (galangin, quercetin, rutin, kaempferol, myricetin, fisetin, morin, tamarixetine, isorhamnetin, gelcitrin) , Isoflavones (daidzein, daidzin, genistein), flavan, flavanols (catechin, epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, theaflavin), flavanones (naringenin, naringin, eriodictyol, boncillin, hesperetin, hesperidin) ), Flavanonol, chalcone and anthocyanidin (cyanidin, cyanine, delphinidin, delphinin, peral Blurred, there pelargonin, Roikoan, cyanidin, propeller Ugo two gin, procyanidins, is prodelphinidin). These flavonoids include celery, parsley, peppers, spring chrysanthemums, lettuce, broccoli, apples, strawberries, onions, tea, buckwheat, chive, radish, grapefruit, cranberries, grapes, soy, tea, cacao, black tea, pomelo, buntan, lemon, It is derived from citrus fruits such as citrus, eggplant, blueberry, and cabbage plant (Junji Terao: antioxidant activity and all antioxidants of flavonoids, pp 121-128, (1998), Advanced Medical Co., Ltd.).
[0033]
Among these, it is preferable to select a solvent that is easily soluble in low-polarity solvents such as alcohol and edible oil. Naringenin, which is a kind of flavanone, other than luteolin is contained in the skin of pomelo and the skin of buntan. In addition, in order to obtain naringenin, it is possible to remove sugar from glycoside naringin contained in grapefruit or the like and use it for this purpose.
[0034]
As the Labiatae plant perilla used in the present invention, perilla commonly used for food can be widely mentioned. Specifically, Lamiaceae perilla (Lamiacea perilla) can be exemplified. The site to be used is not particularly limited, and may be an entire plant of the Labiatae plant or a partial site, for example, any of leaves, stems, roots, flowers, or seeds (edible portion). Preferably, it is a leaf or a seed (edible portion).
[0035]
There are many cultivated varieties of Lamiaceae plants, and different varieties are produced by selection and breeding. There are two types of perilla varieties, L. perilla, and L. perilla, and any of them can be suitably used in the present invention. These perillas can be easily obtained from agricultural cooperatives and retailers such as supermarkets and shops.
[0036]
Luteolin-containing fractions of these Labiatae plants can be prepared and obtained by extracting a Labiatae plant (for example, preferably perilla) in the presence of a solvent. Here, the perilla leaf or fruit of the Labiatae plant may be subjected to the extraction process as it is (raw), or the raw or sliced or shredded crushed material, crushed material, or squeezed liquid may be extracted. It may be subjected to processing. Furthermore, the dried product of the Labiatae plant perilla can be subjected to an extraction treatment as it is or by crushing and crushing. A preferred embodiment for the extraction treatment is a squeezed liquid obtained by crushing raw and then squeezing. Alternatively, compression, distillation (steam distillation, fractional distillation, aroma distilate, recovery essence), extraction (tincture, maceration, percolation, oleoresin, concrete, absolute), and sub-components for preparing components containing a water-soluble fraction It is not limited to a preparation method such as a critical or supercritical extraction method.
[0037]
Examples of the solvent include lower alcohols having 1 to 4 carbon atoms such as methanol, ethanol, 1-butanol, 2-butanol, 1-propanol and 2-propanol; and polyhydric alcohols such as glycerin, propylene glycol, ethylene glycol and butylene glycol. Dihydric alcohol; acetone, ethyl methyl ketone, ethyl acetate, methyl acetate, diethyl ether, cyclohexane, dichloromethane, edible fat, hexane, 1,1,1,2-tetrafluoroethane, 1,1,2-trichloroethene and water Can be mentioned. Preferred are lower alcohols such as ethanol, and water.
[0038]
The solvents listed above may be used alone or in combination of two or more. More preferred is a mixture of water and other components, particularly a mixture of lower alcohol and water (hydrous alcohol), and more preferred is a mixture of ethanol and water (hydrous ethanol). As the hydrated alcohol, specifically, a hydrated alcohol containing water at a ratio of 10 to 99.5% by weight can be suitably used. Luteolin (without sugar) is hardly soluble in ethanol of 40% or less and precipitates in water. Furthermore, the water-soluble fraction may be selectively collected as in the case of alcohol reflux extraction, and the above-mentioned solvent may be distilled off in the purification step to constitute the luteolin or luteolin-containing extract according to the present invention. In addition, a water-soluble fraction, a natural chemical or a synthetic chemical contained in oleoresin, may be used alone or in combination as a constituent. Further, luteolin glycoside may be provided as luteolin easily solubilized in water, and it may be coordinated at the 5-position, 7-position or other positions, and monosaccharides, oligosaccharides and polysaccharides may be provided. Can also be applied.
[0039]
The ratio of the solvent used for the Labiatae plant is not particularly limited, but is usually 50 to 20, when the solvent used for 100 parts by weight of the raw Labiatae or Labiatae plant is converted into a weight ratio. 000 parts by weight, preferably 10 to 10,000 parts by weight.
[0040]
The acrylamide formation inhibitor of the present invention may be composed of only the luteolin or the luteolin-containing plant extract (luteolin-containing fraction of Labiatae plant), or a food-hygienically acceptable agent as long as the effect of the present invention is not impaired. Carriers and additives may be used. Examples of the carrier include water; lower alcohols such as ethanol; polyhydric alcohols such as propylene glycol and glycerin; sugars such as sugar, fructose, glucose, dextrin, cyclodextrin, and cyclic oligosaccharides; It is also possible to make sugar adducts with transferases; sugar alcohols such as sorbitol; gums such as gum arabic, chitosan, xanthan gum; distilled spirits such as sake, vodka and shochu; directly added to emulsifiers, fats and oils or solid fats and oils May be heated, and luteolin or an extract thereof may be mixed and solidified in the molten state. Examples of manufacturing agents such as glycine and sodium acetate can be given. In addition, using an emulsifier such as a glycerin fatty acid ester or a sucrose fatty acid ester as an additive, dissolving in these emulsifiers and mixing, and then providing a liquid or solid state, or luteolin or an extract thereof dissolved in oil with an emulsifier. Any method can be exemplified, such as emulsifying and then providing in the form of a liquid, emulsion, microcapsule, adsorbate or powder or solid.
[0041]
In addition, the acrylamide formation inhibitor of the present invention can also contain other components which have been pointed out as a browning reaction suppressing effect, as long as the effects of the present invention are not impaired. Other browning reaction inhibiting components include vitamin C, sodium erythorbate, vitamin E, bayberry extract, enzyme-treated rutin, and salt.
[0042]
The form of the acrylamide formation inhibitor of the present invention is not particularly limited. For example, the acrylamide formation inhibitor of the present invention, tablets, solids such as granules or powders, liquids such as liquids or emulsions, or semi-solids such as pastes, or water-soluble fractions, as oleoresin, Further, it can be used in the form of a liquid preparation in which the water-soluble fraction is emulsified with an emulsifier. In the powder state, for example, the above-mentioned luteolin or luteolin-containing plant extract (luteolin-containing fraction of Labiatae plant) may be added with saccharides such as dextrin or cyclodextrin or excipients such as sugar alcohols or calcium carbonate, if necessary. In addition to porous inorganic organic substances such as ceramics, silica gel, and activated carbon, it can be prepared by a technique such as freeze drying, spray drying, or freeze pulverization. Preferably, it is in the form of granules in which a powder, particularly an ethanol preparation containing ethanol at a ratio of 10 to 99.5% by weight, is adsorbed on calcium carbonate.
[0043]
The acrylamide formation inhibitor of the present invention can be suitably used in acrylamide formation suppression processing of processed foods, acrylamide formation suppression processing in the process of manufacturing processed foods, and processing steps for quality retention. In this sense, the acrylamide formation inhibitor of the present invention can be defined as a food treatment agent regardless of the purpose of use.
[0044]
Examples of a method for preventing the production of acrylamide in the food include a method in which the above-mentioned acrylamide production inhibitor (treatment agent) of the present invention is brought into contact with food.
[0045]
The contact method is not particularly limited, but a method of applying or spraying an acrylamide formation inhibitor on the surface or cut surface of the food, a method of immersing the food in a solution containing the acrylamide formation inhibitor, a method of applying the acrylamide formation inhibitor to the food. A method of adding and mixing to the compounding can be exemplified.
[0046]
In addition, the addition and mixing of the acrylamide formation inhibitor to foods (including those processed to the state where the original form is not retained) may be performed during the processing of the foods, or the processed products finally obtained. May be performed on. Specifically, it is possible to point out a method of adding to edible oils and fats at the time of frying, adding to fats and oils, and then using for frying or frying.
[0047]
The amount of the acrylamide formation inhibitor of the present invention to be applied to the object to be treated varies depending on the type of the object to be treated, the treatment method, and the like, and cannot be unconditionally specified. When spraying, the amount of luteolin contained in the treatment liquid used for the coating or spraying may be, for example, a ratio of 1 to 100,000 μg / ml, preferably 1 to 1000 μg / ml.
[0048]
When the food is immersed, the amount of luteolin contained in the solution used for the immersion may be 1 to 100,000 μg / ml, preferably 1 to 10,000 μg / ml. it can. When added to edible fats and oils, they can be added in the same ratio.
[0049]
Furthermore, when the acrylamide formation inhibitor is added to and mixed with the food, an amount such that luteolin is contained in the final processed product at a ratio of 1 μg / ml or more, preferably 2 μg / ml or more can be blended. The upper limit is not particularly limited, but is usually 10,000 μg / ml, preferably 2,000 μg / ml.
[0050]
The present invention also provides a food treated with the acrylamide formation inhibitor. The food is not particularly limited as long as it is treated with the acrylamide formation inhibitor.
[0051]
As described above, the acrylamide formation inhibitor of the present invention is characterized in that it has almost no adverse effects such as color, taste, and odor on the object to be processed even when used in food processing. Therefore, the present invention covers a wide range of foods such as foods to be heated and fried, and foods such as retort foods (sealed packaged foods), lunch boxes, and frozen foods to be cooked and eaten when reheated with a stove or boiling water before eating. It can be.
[0052]
Examples of foods targeted by the present invention include fried foods (French fries, potato chips, fried potatoes, corn snacks), sweet chestnuts, bean confectionery, waffles, karinto, senbei, crackers, cereals, barley, almonds, pretzels, Sweets such as cookies and biscuits; processed foods such as croquettes, tonkatsu, french fries, dumplings, spring rolls, etc., sandwiches of fried foods in bread; curry foods using stew, curry, curry powder, Retort foods such as risotto and pasta: grilled onigiri and rice; foods containing tempura such as pork, seafood, and vegetables or noodles with food (kitsune udon with fried food, Nagasaki champon noodles, udon, cold noodles, buckwheat, oil) Fried instant noodles, ramen, etc .; Stir-fried vegetables and rice (Chinese Baking, fried rice, etc.); foods and vegetables seasoned with soy sauce, baked goods (chicken, turkey) of foods and fruits; various types of side dishes such as tempura, vegetable fried fish, fried fish cake, and various ingredients tempura. Preferred drinks to be roasted, such as bento, barley tea, roasted tea, and coffee drinks, can be exemplified. Note that the above is merely an example, and the present invention is not limited to these foods, but can be applied to other foods.
[0053]
【The invention's effect】
The acrylamide formation inhibitor of the present invention contains luteolin, which is a component contained in Labiatae plants such as perilla, whose safety has been confirmed based on food experience, as an active ingredient. Therefore, it can be suitably used as a treatment agent for edible vegetables, foods and foods.
[0054]
In addition, the acrylamide formation inhibitor of the present invention has little problem with odor or coloring derived from Labiatae plants, hardly impairs the flavor of processed foods (oil fried foods), and has the acrylamide of processed foods (oil fried foods). It can be effectively used for suppressing generation and maintaining quality.
[0055]
【Example】
Hereinafter, the content of the present invention will be specifically described with reference to the following Reference Examples, Examples, and Experimental Examples. However, the present invention is not limited to these.
[0056]
Example 1 Luteolin In this test, a reagent luteolin (Mw = 286.24, manufactured by Wako Pure Chemical Industries, Ltd.) was used as a standard substance. Luteolin 0.1 g was accurately weighed and adjusted to 10 ml with 95% ethanol to prepare a 1% ethanol solution. This solution was used for calibration curve preparation, UV spectrum measurement, and HPLC measurement. General information on luteolin was as follows.
UV spectrum data (Figure 1)
The maximum absorption (λmax) of luteolin was found at four peaks at 227, 253, 291 and 343 nm, respectively (0.1% ethanol solution, 0.2 μm membrane filtered). The absorption around 253 nm and 343 nm seems to be derived from the absorption of three OH groups at 5, 7, and 4 '(from the Merck index (12th edition), 268, 333 nm in MeOH).
HPLC data (Figure 2)
HPLC analysis was performed using the sample used in the UV spectrum measurement. As a result, the obtained elution time (RT) was 7.03 min, and one clear peak was observed in the wavelength range (200 to 400 nm). Using this sample, the peak area at λmax (the value of λmax in parentheses) was determined. Their values were 48.7637 (227), 44.4369 (253), 26.2715 (291) and 47.1066 (343).
HPLC condition column: Devosil C30-UG-5 φ4.6 mm × length 250 mm (Nomura Chemical Co., Ltd.)
Solvent: acetonitrile / water (50/50)
Detector: Multi-channel (200-400nm)
Flow rate: 0.6ml
Injection volume: 10 μl
Time: At 45 minutes, the above data was used as basic data and used as an index of luteolin content.
[0057]
Example 2
117 g of perilla (fruit, dried) previously ground with a food cutter is mixed with 300 g of 75% ethanol, and left overnight at room temperature. The above extract was subjected to suction filtration to obtain 191 g of a slightly brown aqueous solution. Next, 110 ml of ethyl acetate, 115 ml of ether and 215 g of water were added to 100 g of the obtained extract, liquid-liquid partitioned, and separated into two layers.
260 g of the upper layer liquid (clear yellow) and 221 g of the lower layer liquid (colorless and transparent light brown) were obtained, and 120 g of the upper layer was concentrated about 5-fold to obtain 23.5 g of an extract concentrate. This solution was filtered through a 0.22 μm membrane filter to obtain an HPLC chromatograph (FIG. 3). In order to determine the content of the obtained luteonin, the concentration was calculated using a calibration curve (Y = 46.261X, r ＾ 2 = 1) obtained from the area and concentration at λ 343 nm in FIG. 1 (peak 4). The content of luteolin contained in the liquid was 0.06%.
[0058]
Example 3
A 10 μg / g sample was added to 600 g of edible salad oil, using the same standard (sample 1) as luteolin found by HPLC chromatography obtained with the Lamiaceae plant perilla extract concentrate prepared in Example 2.
Sample 2: Naringenin (a kind of flavanone)
Naringenin used a reagent (Nacalai Tesque, 98% or more). The addition amount was 10 μg / g with respect to the oil.
Reference Example 1: (±) -α-tocopherol (Wako Pure Chemical Industries, purity 98% or more, density (20 ° C) 0.950 g / ml, reagent, 100 g / g added to 600 g of oil)
Reference Example 2: Butylhydroxyanisole (BHA) (Kishida Chemical Co., Ltd., purity 99%, first grade reagent, 100 g / g added to 600 g of oil)
Reference Example 3: Butylhydroxytoluene (BHT) (Wako Pure Chemical Industries, purity 98% or more, 100 μg / g added to 600 g of reagent and oil)
Reference Example 4: Test plot not using antioxidant, etc. (control product)
Reference Example 5: Sancatechin tea extract (manufactured by Mitsui Norin Co., Ltd., catechin content 10%, 100 μg / g of catechin added to 600 g of oil) (representative example of polyphenol)
[0059]
Example 4 Cooking Method of Frozen Sliced Potato Next, each of the samples prepared in the above Example 3 was added to 600 g of edible salad oil, and 50 g of thawed sliced potato (a shoot ring produced by Pacific Valley Company, USA) was fried (Panasonic). (NF-F150), heat cooking (180 ° C), fry for 2 minutes, take out potatoes immediately, cool at room temperature, cool potatoes in refrigerator (5 ° C) for 12 hours, Was subjected to analysis.
[0060]
Example 5: Pretreatment method and GC-MS analysis method In the pretreatment method, 2 g of a sample was dispersed in 20 ml of a 0.1% formic acid aqueous solution, stirred for 30 minutes, and then centrifuged (8,000 rpm, 30 minutes). Next, the solution is passed through a column cartridge, and the passed solution is collected. An internal standard substance (2,3-dibromo-N, N'-dimethylpropionamide) is added to the collected solution to make the total volume 100 ml. The pH is adjusted to 1.0 or less using 5 M sulfuric acid, and 20 ml of 0.1 M potassium bromate and 50 g of potassium bromide are added thereto, followed by bromination. Subsequently, excess bromine was removed with 1 M sodium thiosulfate, extracted three times with 50 ml of ethyl acetate, dehydrated and concentrated, and then made up to 1 ml with ethyl acetate, followed by GC-MS analysis. Using the above method, the amount of acrylamide contained in the clothes attached to the potato surface was analyzed, and the value of the amount of acrylamide was used to evaluate the effect of inhibiting acrylamide production. (E. Tareke et al: Chem. Res. Toxicol., No. 13, 517-522 (2000), A. Arikawa et al: Bunseki Kagaku, No. 29, T33-T38 (1980), L. Castle et al. : J. Agric. Food Chem., No. 41, 1261-1263 (1993))
GC-MS analysis conditions The GC-MS conditions were as follows.
Equipment: GC 3800 (Varian), MS Saturn2000 (Varian)
Column: DB-5 msitd (J & W), 0.25 mmi. d. × 30m
Injection volume: 1 μl, splitless
Injection temperature: 250 ° C
Column temperature: 60 ° C (1 minute hold, 15 ° C / min) → 250 ° C (10 minute hold)
Transfer line temperature: 280 ° C
Carrier gas: Helium gas Ion trap temperature: 220 ° C
Ionization voltage: 70 eV
Ionization mode: EI +
[0061]
Results The results are shown in Table 1.
[0062]
[Table 1]

Remarks nd: not detected.
The numbers in parentheses in the table indicate the detection limit values.
[0063]
As a result, the value of the antioxidant dissolved in fats and oils (Reference Example 3) was higher than that of the control group (Reference Example 4), and the value of the antioxidant was increased by exposure to heat and air during heating or volatilization of BHT. It was suggested that the effect was lost. On the other hand, Sample 1 which is a component contained in the perilla extract was not detected (detection limit: 50 ppb) as compared with the control group and Reference Examples 1 to 5, or the value was about 1/10 of the control group. Was found to significantly inhibit the production of acrylamide in foods. In addition, naringenin, which separates sugar from glycosides, showed a half (about 55%) inhibitory effect as compared with the value of the control group (Reference Example 4). Therefore, it was suggested that the difference in the structural formula of the flavonoid compound affects the production amount of acrylamide. Furthermore, it was found that when green tea extract was used as an example of a polyphenol that corresponds to the general concept including flavone, the production of acrylamide was not inhibited in the oil-based food system.
This result is a remarkable effect seen in luteolin represented by flavone. Luteolin used in this example was found to act as an acrylamide formation inhibitor in oil (non-aqueous) heated at a high temperature, and as a substance to inhibit the amino-carbonyl reaction.
[Brief description of the drawings]
FIG. 1 shows an absorption spectrum of luteolin obtained in Example 1.
FIG. 2 shows an HPLC chromatogram of luteolin obtained in Example 1.
FIG. 3 shows an HPLC chromatogram of a concentrated solution of perilla seed extract obtained in Example 2.

Claims (9)

An acrylamide formation inhibitor for food, containing luteolin as an active ingredient. The acrylamide formation inhibitor according to claim 1, which is luteolin. The acrylamide production inhibitor according to claim 1 or 2, which contains luteolin derived from a Labiatae plant as an active ingredient. The acrylamide formation inhibitor according to claim 3, wherein the luteolin derived from the Labiatae plant is derived from the water-soluble fraction of the Labiatae plant. The said Labiatae plant is one or two or more species selected from perilla (blue perilla or red perilla) leaves, seeds, or spring chrysanthemum (Asteraceae), celery (Apiaceae), peppers (Solanaceae). Item 5. The acrylamide formation inhibitor according to item 3 or 4. 5. The acrylamide production inhibitor according to claim 3, wherein the Lamiaceae plant is at least one member selected from perilla leaves or perilla seeds. 6. A food composition comprising the food acrylamide formation inhibitor according to any one of claims 1 to 6. A method for producing a food, comprising the step of adhering the acrylamide production inhibitor for food according to any one of claims 1 to 6 or the composition for food according to claim 7 to oil at the time of frying or the surface of food. Acrylamide formation suppression method. A food treated with the food acrylamide formation inhibitor according to any one of claims 1 to 6 or the food composition according to claim 7.

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