JP2022136547A - Meat texture improver - Google Patents

Abstract

To provide a meat texture improver which can obtain meat processed food which is tender and has juicy feeling even when processing such as heating cooking is applied to meat such as livestock meat and fish meat.SOLUTION: A meat texture improver containing a pentacyclic triterpene is used to treat meat such as livestock meat and fish meat.SELECTED DRAWING: Figure 1

Description

The present invention relates to meat quality improvers.

Meat, including livestock meat such as beef, pork, and chicken, and seafood such as fish and shellfish, may have a soft texture and a juicy texture that retains moisture after being cooked. Desired. However, when meat is cooked with oil, heated in an oven, heated in a frying pan, or heated in a microwave oven, the moisture and fat content from the inside of the meat is lost due to scattering and leakage, etc., so the texture of the heated meat is It tends to be hard and dry. In addition, the proteins that make up the meat are denatured by heating, causing shrinkage and coagulation, which tends to make the hard and dry texture more conspicuous.
Various investigations have been made to solve such problems. For example, food modifiers containing oil-processed starch and egg white decomposition products (Patent Document 1), meat additives containing water-soluble cellulose ethers that gel with heat agent (Patent Document 2), livestock meat improver containing proteolytic enzymes such as protease (Patent Document 3), powder composition for cooking simple meat products containing polysaccharides such as xanthan gum (Patent Document 4), and modified starch. A meat processing mix containing sodium bicarbonate (Patent Document 5) and the like have been proposed.

As for fried meat products, a method of injecting a proteolytic enzyme solution to soften the meat quality and a method of allowing the proteolytic enzyme to act on the meat for a relatively long period of time are known as pretreatment methods. As one of such techniques, a cooking method called marinating, in which meat used for fried food is immersed in a seasoning liquid, has been used for a long time. Marinade is a cooking method in which a seasoning liquid is impregnated into meat by immersion for the purpose of producing juicy and voluminous fried chicken without losing flavor and meat juices. A tumbling process is also performed in which the seasoning liquid is permeated into the meat, etc., without soaking. Other methods for obtaining softness and juiciness include a method of using a pickling liquid for meat processing containing polyglycerin fatty acid ester (Patent Document 6), and a method of blending a protease in the marinade (Patent Document 7). etc. are known. Furthermore, it is also known that by including a specific diglyceride, it is possible to provide a fried product that melts in the mouth (Patent Document 8).

On the other hand, it is widely known that pentacyclic triterpenes have various physiological functions. For example, maslinic acid is known to have physiological functions such as an anti-obesity effect (Non-Patent Document 1) and a lipid metabolism improving effect (Non-Patent Document 2). Attempts have been made to use pentacyclic triterpenes having such physiological functions in foods. Patent Document 9 discloses a carbohydrate diet, a food containing at least one triterpene selected from the group consisting of corosolic acid, maslinic acid and tormentic acid, and a food containing such food ingredients, wherein glycemic It is stated that the index can be reduced. Patent Document 10 discloses a skin-whitening food, drink or oral whitening agent containing, as an active ingredient, a compound selected from the group consisting of pentacyclic triterpenes and their physiologically acceptable salts or derivatives thereof. It is described that the production of melanin was suppressed. All of the inventions are expected to exhibit the physiological functions of pentacyclic triterpenes in living bodies, and do not describe or suggest that pentacyclic triterpenes improve the texture of meat.

JP 2007-300918 A JP 2011-087490 A JP 2015-211654 A JP 2017-112852 A WO2018/174229 JP 2007-043949 A JP-A-05-252911 JP-A-2005-237391 JP 2006-121949 A Retable 2002-043736

Liou CJ et al., FASEB J. 2019.Nov;33(11):11791-11803 Perez-Jimenez A et al., Phytomedicine. 2016. Nov 15;23(12):1301-1311

It is an object of the present invention to provide a meat quality improving agent capable of obtaining a soft and juicy processed meat food even when meat such as livestock meat and fish meat is processed by heat cooking or the like.

As a result of intensive studies to solve the above problems, the present inventors have found that by treating meat such as livestock meat and fish meat with a meat quality improving agent containing a pentacyclic triterpene, processing such as cooking is performed on meat. The inventors have found that a processed meat food with a soft and juicy feeling can be obtained even if they are applied, and have completed the present invention.

That is, the present invention includes the following aspects.
[1] A meat quality improving agent containing a pentacyclic triterpene.
[2] The meat quality improving agent according to [1], wherein the pentacyclic triterpene is one or more selected from the group consisting of oleanane-type triterpene, ursan-type triterpene, lupine-type triterpene and hopane-type triterpene.
[3] A method for improving meat quality, comprising the step of treating meat with the meat quality improving agent according to [1] or [2].
[4] A method for producing a processed meat food comprising the steps of treating meat with the meat quality improving agent according to [1] or [2] and heating the treated meat.

According to the present invention, by treating meat such as livestock meat, animal meat, and seafood meat with the meat quality improving agent of the present invention, the meat quality does not become dry and hard even when subjected to processing such as cooking, and is soft. A juicy processed meat food can be obtained. Furthermore, physiological health functions such as anti-obesity and improvement of lipid metabolism inherent to pentacyclic triterpenes can also be expected.

1 is an HPLC analysis chart of pentacyclic triterpene powder 1 (oleanane-type triterpene powder derived from olive fruit).

<Pentacyclic triterpene>
A triterpene is a compound having a basic skeleton of 30 carbon atoms, and a pentacyclic triterpene is a pentacyclic compound composed of 6 isoprene units. Since pentacyclic triterpene is a type of triterpene, it basically has 30 carbon atoms, but it also includes those that are rearranged, oxidized, eliminated or alkylated during the biosynthetic process and the number of carbon atoms fluctuates. Pentacyclic triterpenes are generally classified by their backbone. Examples include oleanane-type triterpenes, ursan-type triterpenes, lupine-type triterpenes, hopane-type triterpenes, serratane-type triterpenes, Friederan-type triterpenes, taraxerane-type triterpenes, taraxastane-type triterpenes, multifloran-type triterpenes, Germanican-type triterpenes, and the like.

（式１）オレアナン型（Oleanane）トリテルペン

（式２）マスリン酸（Maslinic acid）

（式３）オレアノール酸（Oleanolic acid）

（式４）グリチルレチン酸（Glycyrrhetinic acid） The oleanane-type triterpene is a pentacyclic triterpene having a structure represented by the following formula 1 as a basic skeleton, and maslinic acid (formula 2), oleanolic acid (formula 3), glycyrrhetinic acid (formula 4), etc. are classified into one group. be done.

(Formula 1) Oleanane triterpene

(Formula 2) Maslinic acid

(Formula 3) Oleanolic acid

(Formula 4) Glycyrrhetinic acid

（式５）ウルサン型（Ursane）トリテルペン

（式６）コロソリン酸（Corosolic acid）

（式７）ウルソール酸（Ursolic acid） Ursane-type triterpenes are pentacyclic triterpenes having a structure represented by the following formula 5 as a basic skeleton, and corosolic acid (formula 6), ursolic acid (formula 7) and the like are classified into this group.

(Formula 5) Ursane triterpene

(Formula 6) Corosolic acid

(Formula 7) Ursolic acid

（式８）ルパン型（Lupane）トリテルペン

（式９）ベツリン酸（Betulinic acid）

（式１０）アルフィトール酸（Alphitolic acid） Lupine-type triterpenes are pentacyclic triterpenes having a structure represented by the following formula 8 as a basic skeleton, and betulinic acid (formula 9), alphytolic acid (formula 10) and the like are classified into this group.

(Formula 8) Lupane triterpene

(Formula 9) Betulinic acid

(Formula 10) Alphitolic acid

（式１１）ホパン型（Hopane）トリテルペン

（式１２）ロイコチル酸（Leucotylic acid） Hopane-type triterpenes are pentacyclic triterpenes having a structure represented by the following formula 11 as a basic skeleton, and leucotylic acid (formula 12) and the like are classified into this group.

(Formula 11) Hopane triterpene

(Formula 12) Leucotylic acid

In the meat quality improving agent of the present invention, the pentacyclic triterpene is preferably one or more selected from the group consisting of oleanane-type triterpene, ursan-type triterpene, lupine-type triterpene and hopane-type triterpene, more preferably oleanane-type triterpene. and ursan-type triterpenes, more preferably any one or more selected from the group consisting of maslinic acid, oleanolic acid and ursolic acid. In addition, when it has a carboxyl group in its molecule, it is generally called a pentacyclic triterpenoic acid, but in this specification, the pentacyclic triterpenoic acid is included in the pentacyclic triterpene.

Pentacyclic triterpenes are biosynthesized by various plants and are ubiquitous or localized in fruits, petals, cotyledons, stems, roots, etc. of the plants. For example, maslinic acid, which is classified as a group of oleanane-type triterpenes, is contained in olive fruits and leaves, jujubes, almonds, banaba leaves, sage, apples, cranberries, Chinese quince, and the like. Oleanolic acid, which is classified into a group of oleanane-type triterpenes, is used in olive fruits and leaves, grapes, beets, jujubes, almonds, banaba leaves, sage, hawthorn, raspberries, quince, rosemary leaves, guava, perilla leaves, blueberries, prunes, It is contained in loquat, pomegranate, lemon balm, basil, rosehip, persimmon, and assembly. Ursolic acid, which is classified as a group of ursan-type triterpenes, is contained in apples, basil, bilberries, cranberries, elderflowers, peppermint, rosemary, lavender, oregano, thyme, hawthorn, prunes, and the like.

A pentacyclic triterpene can be obtained by extraction, fractionation, and purification from a plant containing it by a known method, and can also be obtained by chemical synthesis. Moreover, a commercial item can also be used suitably. It can also be used in the form of pharmacologically acceptable salts and/or derivatives. The pentacyclic triterpene may be a single component or a mixture (combination) of two or more components.

Pentacyclic triterpenes may be used in the form of plant extracts containing them. If it is an oleanane-type triterpene, its content is reasonably high, it has been eaten for a long time, and secondary use after oil extraction is possible. is preferred. Ursane-type triterpenes are preferably used in the form of apple peel extracts, since they can be used for secondary purposes after squeezing or food processing.

If it is an olive fruit extract, dried or semi-dried or undried olive fruit containing water, olive oil residue generated in the oil extraction process, defatted product from which oil is removed with a fat-soluble organic solvent such as n-hexane, etc. can be used as a starting material to obtain an olive fruit extract. Specifically, when olive oil residue is used as a starting material, a lower alcohol capable of extracting an oleanane-type triterpene (e.g., ethanol, methanol, n-propanol, isopropanol, n-butanol, etc.) or a water-containing lower alcohol thereof The pentacyclic triterpene is extracted with alcohol, optionally subjected to saponification and neutralization, and fractionated and purified using octadecyl silica (ODS), silica gel, synthetic adsorbents, etc. as adsorbents to obtain oleanane type. Mixtures of pentacyclic triterpenes containing triterpenes as main components can be obtained. The pentacyclic triterpene fraction extracted from the olive oil residue in this way contains maslinic acid and oleanolic acid in a ratio of 4:1, but the growing conditions of the olive fruit, the growing region, Alternatively, the ratio may be 1:1 to 7:1 depending on the oil extraction conditions. By further fractionating and purifying to a high degree, individual oleanane-type triterpenes such as maslinic acid and oleanolic acid can be obtained alone or as fractions containing trace amounts of other pentacyclic triterpenes. There are no particular restrictions on the variety of olives used, and olives can be used regardless of whether they are domestic or foreign, whether they are for food, for oil extraction, or for ornamental purposes.

In the case of almond seed extract, semi-dried or undried almond seeds containing dry or moist almonds, almond oil residue, by-products discharged from the manufacture of processed foods such as snacks, or husks discharged during threshing of almonds. Using by-products such as and husks as starting materials, pentacyclic triterpenes are extracted with lower alcohols or hydrous lower alcohols, optionally saponified or neutralized, and octadecyl silica (ODS), silica gel, and synthetic adsorption are used as adsorbents. A mixture of pentacyclic triterpenes containing maslinic acid and/or oleanolic acid as main components can also be obtained by fractionating and purifying using agents or the like. In general, almond shells are used as a fuel material, and the outer skins are used as compost.

In the case of apple peel extract, by-products such as apple juice lees and apple peel peeled at food factories etc. are used as starting materials, pentacyclic triterpenes are extracted with lower alcohols or hydrous lower alcohols, and optionally saponified. To obtain a mixture of pentacyclic triterpenes containing ursolic acid as a main component by performing treatment and neutralization treatment, and fractionating and purifying using octadecyl silica (ODS), silica gel, synthetic adsorbents, etc. as adsorbents. can also

When plants other than olive fruits, almonds, and apple peels are used as starting materials, the pentacyclic triterpene can be obtained by a method suitable for the plant used as the starting material. In addition, the type and composition ratio of the components of the pentacyclic triterpene to be obtained depend on the plant used as the raw material.

Pentacyclic triterpenes have functional groups such as hydroxyl groups, carboxyl groups, aldehyde groups, ketone groups, etc. These functional groups are modified or intramolecularly crosslinked by various compounds in the plant body. For example, glycyrrhizin, which is contained in licorice and used as a sweetener, is a glycoside in which two glucuronic acids are ether-bonded through the 3β hydroxyl group of glycyrrhetinic acid, which is classified as an oleanane-type triterpene. In general, such compounds having modified functional groups are eliminated during extraction, fractionation, and purification processes, and pentacyclic triterpenes obtained through extraction, fractionation, and purification processes are generally in the free form.

Physiologically acceptable salts of pentacyclic triterpenes include salts with inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, nitric acid, pyrosulfuric acid, and metaphosphoric acid. salts with organic acids such as citric acid, benzoic acid, acetic acid, propionic acid, fumaric acid, maleic acid and sulfonic acid; and alkali metal salts such as sodium salts and potassium salts.

<Meat quality improving agent>
The meat quality improving agent of the present invention contains a pentacyclic triterpene as an active ingredient. Preferably, the pentacyclic triterpene is one or more selected from the group consisting of oleanane-type triterpene, ursan-type triterpene, lupine-type triterpene and hopane-type triterpene, more preferably oleanane-type triterpene and ursan-type triterpene. Any one or more selected from the group, more preferably any one or more selected from the group consisting of maslinic acid, oleanolic acid and ursolic acid.

The meat quality improving agent of the present invention may consist of a pentacyclic triterpene, and may be mixed with other ingredients depending on the purpose of use or mode of use, and may be in the form of powder, granules, tablets, liquid, or the like. can be
When used in the form of powder, granules, tablets, etc., other ingredients include agar, gelatin, carrageenan, gellan gum, xanthan gum, locust bean gum, tamarind seed gum, sodium alginate, pectin, curdlan, and cellulose derivatives. thickening polysaccharides such as; excipients such as dextrin, lactose, mannitol, starch (raw starch, modified starch); ferric ammonium citrate, anhydrous sodium phosphate, calcium phosphate, anhydrous magnesium sulfate, magnesium chloride, calcium chloride, carbonate Anti-caking agents such as magnesium, calcium carbonate, fine silicon dioxide and magnesium oxide; inclusion compounds such as cyclodextrin and highly branched cyclic dextrin; be done.

When used in a liquid form, it can be obtained by selecting a liquid as another component and dissolving or dispersing it in the liquid. Such liquids include water, ethanol, propylene glycol, starch syrup, honey, etc., and may be a mixture of one or more of these.

In addition, a fat composition in which a pentacyclic triterpene is dissolved or dispersed in an edible fat or oil, or a W/O or O/W emulsified composition of an edible fat, water and an emulsifier may be used. Such edible oils and fats include soybean oil, cottonseed oil, safflower oil, rice oil, corn oil, rapeseed oil, perilla oil, perilla oil, linseed oil, olive oil, sesame oil, wheat germ oil, rice bran oil, sunflower oil, and peanut oil. oil, avocado oil, egg yolk oil, fish oil, whale oil, chicken oil, lard, beef tallow, milk fat, cacao butter, shea butter, coconut oil, palm oil, palm kernel oil, etc., and hydrogenation, fractionation and esterification of these Examples include processed oils and fats that have been subjected to one or more treatments such as exchange treatment. Emulsifiers include natural emulsifiers such as lecithin (derived from soybean, egg yolk, etc.), saponin (derived from quillaja, soybean, etc.), sodium caseinate (derived from milk); Synthetic emulsifiers which are composed of unsaturated fatty acids and whose hydrophilic groups are composed of glycerin, polyglycerin, sucrose, propylene glycol, sorbitan, etc., and which can be used for foods are mentioned. When making it into an emulsified composition, a pentacyclic triterpene, fats and oils, water|moisture content, and an emulsifier can be manufactured by a well-known method using a high-pressure homogenizer, a high-speed stirrer, etc.

The meat quality improving agent of the present invention can be used in combination with various quality improving agents and additives as other components other than those mentioned above as long as the effects of the present invention are not impaired. Such ingredients include sweeteners such as glucose, fructose, sucrose, maltose, sorbitol, trehalose, and stevia; umami seasonings such as sodium glutamate and sodium inosinate; Vitamins; Organic acids such as acetic acid, lactic acid, and citric acid; Antioxidants such as tocopherol, propyl gallate, chlorogenic acid, sodium sulfite, butylhydroxyanisole, and catechin; Colorants such as β-carotene, caramel, and Monascus pigment Extracts such as consommé, bouillon, bonito stock, and yeast extract; fermented seasonings such as yogurt, cheese, and soy sauce; enzymes such as amylase, protease, cellulase, lipase, and transglutaminase; fragrances; Eggs; milk; preservatives; fruit juice; spices and the like.

The content of the pentacyclic triterpene in the meat quality improving agent of the present invention is not particularly limited, and can be appropriately adjusted so that the effects of the present invention can be obtained when processed meat foods are produced. For example, it may be 1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, relative to the total amount of the meat quality improving agent.
The meat quality improving agent of the present invention can be produced by mixing and/or dissolving the pentacyclic triterpene and any of the above components, and the production method is not particularly limited.

Meat to which the meat quality improving agent of the present invention is applied is not particularly limited, and any commonly eaten meat can be suitably applied.
Examples of such meat include mammals such as cattle, pigs, horses, sheep, goats, rabbits, wild boars and deer; birds such as chickens, quails, ducks, geese, ducks, turkeys and ostriches; tuna, salmon, cod, Fish such as sea bream, marlin, sardine, mackerel, horse mackerel, saury, eel, carp, crucian carp; sea mammals such as whales, dolphins, seals and walruses; reptiles such as crocodiles, turtles and snakes; amphibians such as frogs and salamanders; mollusks such as squid; shellfish such as scallops, clams and clams; crustaceans such as spiny lobster and tiger prawn. These meats may be used alone or in combination of two or more.
There are no particular restrictions on the parts of the meat. Beef can be sirloin, fillet, loin, belly, rib loin, rump, etc. Pork can be loin, fillet, belly, thigh, etc. Chicken can be breast, thigh, chicken wings, etc. Chicken fillet etc. are mentioned. The shape of the meat is also not particularly limited, and examples include block-shaped, fillet-shaped, diced, stick-shaped, slice-shaped, minced-shaped, minced meat-shaped lumps of meat, and the like.

<Meat quality improvement method>
The method for improving meat quality of the present invention includes the step of treating meat with the meat quality improving agent containing the pentacyclic triterpene of the present invention. Here, "treating meat with a meat quality improving agent" is not particularly limited as long as it is a processing method that can bring the pentacyclic triterpene and meat into contact. etc.), tumbling (process of mechanically infiltrating seasoning liquid etc. into meat), pickling (process of adding seasoning liquid etc. to meat and allowing it to stand still), spraying (seasoning liquid etc. into meat) etc.), coating (applying seasoning liquid, etc., to meat using a brush, etc.), mabushi (coating meat with powdered seasoning, etc.), stewing (cooking meat with soup stock, etc.) and the like, and one or two or more methods selected from these methods can be employed.

The amount of the meat quality improving agent to be used can be appropriately set in consideration of the type, quality, size and shape of the meat to be used, the meat quality improving method to be employed, and the like. From the viewpoint of effectively improving meat quality, the amount of pentacyclic triterpene used is 0.001 parts by mass or more, preferably 0.003 parts by mass or more, more preferably 0 parts by mass per 100 parts by mass of meat. 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more. The upper limit of the amount of pentacyclic triterpene used is not particularly limited, but from the viewpoint of production efficiency, it is 20 parts by mass or less, preferably 10 parts by mass or less, more preferably 10 parts by mass or less per 100 parts by mass of meat. It is 5 parts by mass or less. By using the pentacyclic triterpene in this range, the meat quality can be improved satisfactorily.
The treatment time of meat with a meat quality improving agent (pentacyclic triterpene) is not particularly limited, but is preferably 10 seconds to 24 hours, more preferably 1 minute to 2 hours, and still more preferably 2 minutes to 1 hour. The longer the treatment time, the better the meat quality improvement effect, but from the viewpoint of production efficiency, it is desirable to set the treatment time to 1 hour or less.

<Method for producing processed meat food>
In the present invention, processed meat food refers to food processed by heating meat.
The method for producing the processed meat food of the present invention includes the steps of treating meat with the meat quality improving agent and heating the meat modified with the meat quality improving agent.
The processed meat food obtained by the method for producing the processed meat food of the present invention is not particularly limited, and includes fried chicken, fried Tatsuta, fried chicken, pork cutlet, beef cutlet, fried tuna, fried salmon, fried shrimp, fried scallops, and fritters. Fried meat such as fried meat and non-fried fried meat; Grilled meat such as steak, roast beef, roast pork, grilled chicken, grilled fish; Stewed meat such as curry, stew, pot-au-feu; Boneless ham, bacon, sausage, smoked salmon, etc. Smoked meats; minced meats such as hamburgers, meatballs, meatballs, fish cakes, kamaboko, and chikuwa; dried meats such as beef jerky and horse mackerel.
Among them, fried foods, grilled meats, and stewed meats, more preferably fried meats and grilled meats, from the viewpoint that the effects of the present invention can be obtained well. Moreover, it is preferably a processed meat food using lump meat that has not been ground or minced.

In the method for producing the processed meat food of the present invention, the treatment method in the step of treating the meat with the meat quality improving agent is not particularly limited. , tumbling (a process of mechanically permeating meat with a seasoning liquid, etc.), marinating (a process of adding a seasoning liquid, etc., to the meat and allowing it to stand still), spraying (a process of mechanically spraying the seasoning liquid, etc., onto the meat), Methods such as coating (a process of applying a seasoning liquid, etc. to the meat using a brush, etc.), glazing (a process of coating the meat with a powdered seasoning, etc.), and simmering (a process of simmering the meat with soup stock, etc.), etc., can be mentioned. One or two or more methods selected from methods can be employed.
The amount of the meat quality improving agent to be used can be appropriately set in consideration of the type, quality, size and shape of the meat to be used, the meat quality improving method to be employed, and the like. From the viewpoint of effectively improving the meat quality, the amount of the pentacyclic triterpene used is 0.001 parts by mass or more, preferably 0.003 parts by mass or more, relative to 100 parts by mass of the meat used in the production of the processed meat food. , more preferably 0.01 parts by mass or more, still more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more. The upper limit of the amount of pentacyclic triterpene used is not particularly limited, but from the viewpoint of production efficiency, it is 20 parts by mass or less, preferably 10 parts by mass, based on 100 parts by mass of meat used in the production of processed meat foods. or less, more preferably 5 parts by mass or less. By using the pentacyclic triterpene in this range, the meat quality can be improved satisfactorily.
The treatment time of meat with the meat quality improving agent is not particularly limited, but is preferably 10 seconds to 24 hours, more preferably 1 minute to 2 hours, and still more preferably 2 minutes to 1 hour. be. The longer the treatment time, the better the meat quality improvement effect, but from the viewpoint of production efficiency, it is desirable to set the treatment time to 1 hour or less.

The method for producing the processed meat food of the present invention further includes a step of heating the meat treated with the meat quality improving agent. The heating method is not particularly limited, and includes frying (boiled oil) heating, frying pan heating, oven heating, direct fire heating, smoked heating, steam heating, steam convection heating, superheated steam heating, simmering heating, microwave heating, and the like. are mentioned. The heating temperature is not particularly limited, and can be appropriately adjusted according to the processed meat food to be produced. For example, 160-220°C for frying, 170-240°C for frying, 70-300°C for oven heating, 30-100°C for smoked heating, and 50-100°C for steam heating. °C, 120 to 300°C for steam convection heating, 100 to 350°C for superheated steam heating, and 50 to 100°C for stew heating.

The resulting processed meat food may be stored frozen after quick freezing, and reheated after thawing or without thawing. For example, in the case of fried chicken, the chicken thigh meat to which the meat quality improving agent is applied is coated with a coating material, fried in a hot oil bath, and after removing the rough heat, it is quickly frozen at -40 ° C and frozen. The fried chicken can be obtained by storing the fried chicken in a freezer of a home freezer-refrigerator for 10 days and re-frying in a hot oil bath or heating in a microwave oven without thawing.

In the present invention, the meat can also be processed into frozen processed meat or chilled processed meat without heating after being treated with the meat quality improving agent. For example, in the case of fried chicken, chicken thigh meat treated with a meat quality improving agent is coated with a coating material, placed in a container, and then quickly frozen at -40 ° C. to deep-fried frozen non-oiled chicken. can. After being stored in a freezer or the like of a household freezer/refrigerator, fried chicken can be obtained by frying the chicken in a thawed or unthawed state in a heated oil bath.

EXAMPLES Hereinafter, examples will be given in order to specifically describe the present invention, but the present invention is not limited only to the following examples.

<Production Example 1 Production of pentacyclic triterpene powder 1>
(1) Olive fruit was pressed to obtain olive oil by a cold press method to obtain olive fruit residue.
(2) Add 250 parts by mass of 90% hydrous ethanol (v/v) to 100 parts by mass of olive fruit pomace, heat at 70°C for 2 hours while stirring, and remove the liquid portion obtained by solid-liquid separation with an evaporator. It was distilled off under reduced pressure to obtain a concentrate.
(3) The concentrate was dispersed in water, subjected to column chromatography using synthetic adsorption resin Amberlite XAD4 (Organo Co., Ltd.) as a carrier, and stepwise elution from 50% hydrous ethanol to 100% ethanol in increments of 10%. A triterpene-rich fraction was collected.
(4) The triterpene-rich fraction was distilled off under reduced pressure to prepare a liquid oil-like olive fruit-derived triterpene-containing liquid.
(5) Add 100 parts by mass of 20% hydrous ethanol to 100 parts by mass of this triterpene-containing liquid, mix well and dissolve, allow to stand overnight at 4°C to precipitate, collect and wash the precipitate by filtration. , and after drying under reduced pressure, the pentacyclic triterpene powder 1 was obtained by pulverizing using a pin mill.
(6) 1 g of pentacyclic triterpene powder 1 was dissolved in methanol and subjected to HPLC analysis. FIG. 1 is its HPLC chart, and the peak of A was maslinic acid and the peak of B was oleanolic acid. The peaks were identified by comparison of retention times with standard products and LC/MS analysis, and quantitative values were calculated based on the peak areas of standard products. As a result, it was found that pentacyclic triterpene powder 1 contained 50% by mass of maslinic acid and 30% by mass of oleanolic acid (both oleanane-type triterpenes derived from olive fruits).

<Production Example 2 Production of pentacyclic triterpene powder 2>
(1) A liquid oil-like olive fruit-derived triterpene-containing liquid was prepared according to Production Example 1, except that gradient elution from 50% hydrous ethanol to 100% ethanol was performed instead of the stepwise elution, and powdered. A cyclic triterpene powder 2 was obtained.
(2) When the obtained pentacyclic triterpene powder 2 was subjected to HPLC analysis (HPLC chart is omitted), the content of oleanane-type triterpene was 90% by mass, the content of maslinic acid was 90% by mass, and the content of oleanolic acid was 90% by mass. The content was 0% by mass.

<Production Example 3 Production of Marinade>
0.2 parts by mass of common salt, 0.3 parts by mass of sodium glutamate and 13.6 parts by mass of water were put into a mixer and dissolved, and then 0.2 parts by mass of pentacyclic triterpene powder 1 was added. Mix until homogeneous to produce a marinating liquid (meat quality improver).

<Production Example 4 Production of fried chicken>
(1) A 250 g chunk of chicken thigh was cut into 10 pieces of about 25 g of chicken thigh.
(2) The total amount of the marinade liquid (14.3 parts by mass) obtained according to Production Example 3 and 100 parts by mass of chicken thigh pieces were combined and tumbled for 30 minutes (0.2 parts by mass per 100 parts by mass of chicken thigh pieces pentacyclic triterpene powder 1). After tumbling, almost no marinate liquid remained in the tumbler.
(3) The seasoned chicken thigh pieces were put into a batter liquid (Nippon Co., Ltd., soy sauce from Paris), and the chicken thigh pieces were coated with the batter liquid to obtain non-oil fried chicken. When the batter weight before and after coating was measured, each chicken thigh piece was coated with 10 g of batter liquid.
(4) The obtained non-oil fried chicken is placed in an oil bath preheated to 170 ° C and fried for 4 minutes, arranged so that it does not overlap on a metal oil drainer, drained, and fried chicken. Obtained.

<Evaluation Example 1 Sensory evaluation of fried chicken>
The resulting deep-fried chicken was evaluated by 10 skilled panelists according to the following criteria. The fried chicken (Reference Example 1) prepared using a marinate solution containing no pentacyclic triterpene powder by substituting water for the pentacyclic triterpene powder was given 3 points.

Texture (tenderness of meat)

Texture (meat juiciness)

<Test Example 1 Effect of pentacyclic triterpenes on the texture of fried chicken>
A marinate liquid was prepared according to Production Example 3 except that the pentacyclic triterpene powder of the parts by mass shown in Table 1 was used, fried chicken was produced according to Production Example 4, and evaluated according to Evaluation Example 1. SD stands for standard deviation. In preparing the marinade, the pentacyclic triterpene powder was added as an external blend to the total amount of components other than the pentacyclic triterpene powder.
As a result, in Example 1 using 0.008 parts by mass of olive fruit-derived oleanane-type triterpene (pentacyclic triterpene) per 100 parts by mass of chicken thigh pieces, the meat tenderness and meat juiciness were slightly improved. Both the tenderness and juiciness of the meat were improved as the amount of the olive fruit-derived oleanane-type triterpene used was increased. Similarly, in Examples 6 and 7, in which the olive fruit-derived oleanane-type triterpene was only maslinic acid, both the tenderness and the juiciness of the meat improved with an increase in the amount used. Example 4 in which the olive fruit-derived oleanane-type triterpene consists of maslinic acid and oleanolic acid and Example 6 in which the maslinic acid contains oleanane-type triterpene were equivalent in evaluation of meat tenderness and juiciness. It was found that the texture of deep-fried chicken was improved if the type triterpene was included.

５ＴＴは五環性トリテルペンの略である。
ＯＴＴはオレアナン型トリテルペンの略である。
＊：鶏モモ肉片１００質量部当たりのタンブリング量（質量部）である。 Table 1

5TT is an abbreviation for pentacyclic triterpene.
OTT is an abbreviation for oleanane-type triterpene.
*: Amount of tumbling (parts by mass) per 100 parts by mass of chicken thigh pieces.

<Test Example 2 Consideration of tumbling treatment time>
Fried chicken was produced according to Production Example 4 and evaluated according to Evaluation Example 1, except that the tumbling treatment time shown in Table 2 was used. The amount of marinating liquid remaining in the tumbler was determined by removing the chicken from the tumbler after tumbling, weighing the tumbler together with the remaining marinating liquid, and subtracting the weight of the empty tumbler.
As a result, both the tenderness and juiciness of the meat were improved, depending on the reduction in marinating liquid remaining in the tumbler. From this, it was found that the texture of the meat (chicken) is improved depending on the amount of the olive fruit-derived oleanane-type triterpene attached to or absorbed by the meat (chicken). The reason why the meat of Example 11 was slightly more tender than that of Example 2 was that the fibers of the meat were loosened by the impact of tumbling.

Table 2

<Production Example 5 Production of beef steak>
(1) Water was added to the marinade liquid of Production Example 3 to make the total amount 20 parts by mass, and this was used as a pickle liquid (meat quality improving agent).
(2) Australian beef lean meat was trimmed into a substantially rectangular parallelepiped with a thickness of 2 cm.
(3) Lean beef meat was completely laid on a tray, and 20 parts by mass of pickling liquid was injected with respect to 100 parts by mass of lean beef meat.
(4) Lean beef injected with a pickling liquid was placed on an iron plate preheated to 220° C. and baked to a medium rare to obtain a beef steak.

<Test Example 3 Effects of pentacyclic triterpenes on texture of beef steak>
A beef steak was produced according to Production Example 5 except that the amount of pentacyclic triterpene shown in Table 3 was used, and evaluated according to Evaluation Example 1. Pentacyclic triterpene powder is included in the preparation of the pickling solution. In the evaluation, the tenderness and juiciness of the beef steak (Reference Example 2) injected with the pickling liquid in which the pentacyclic triterpene was replaced with water was rated as 3 points.
As a result, the tenderness and juiciness of the meat improved with an increase in the amount of oleanane-type triterpenes injected into lean beef. In Example 14 containing maslinic acid and oleanolic acid having the same oleanane-type triterpene content and Example 15 containing only maslinic acid, both the tenderness and juiciness of the meat were equivalent.

５ＴＴは五環性トリテルペンの略である。
ＯＴＴはオレアナン型トリテルペンの略である。
＊：牛赤身肉１００質量部当たりのインジェクション量（質量部）である。 Table 3

5TT is an abbreviation for pentacyclic triterpene.
OTT is an abbreviation for oleanane-type triterpene.
*: Injection amount (parts by mass) per 100 parts by mass of lean beef.

<Production Example 6 Production of fried squid>
(1) After removing the viscera and thin skin, the squid was opened, thoroughly wiped dry, cut into grid-like cuts on both sides, and cut into strips of 5 cm x 2 cm to obtain squid fillets.
(2) 97.5 parts by mass of cake flour, 1.5 parts by mass of powdered chicken stock and 1 part by mass of pentacyclic triterpene powder 1 are added to a mixer, mixed until homogeneous and sprinkled with powder (meat quality improving agent ).
(3) 100 parts by mass of squid fillets and 5 parts by mass of glazing powder were placed in a resin bag, and tapped for 1 minute until the glazing powder was evenly attached to the squid fillets.
(4) The squid fillets coated with glazed powder were placed in an oil bath preheated to 170°C and fried for 2 minutes.

<Test Example 4 Effects of pentacyclic triterpenes on the texture of fried squid>
Fried squid was produced according to Production Example 6 except that the pentacyclic triterpene powder of the parts by mass shown in Table 4 was used, and evaluated according to Evaluation Example 1. In the preparation of the dusting powder, the pentacyclic triterpene powder was replaced with soft flour. In the evaluation, the softness and juiciness of the meat of fried squid (Reference Example 3) using the glazing powder containing no pentacyclic triterpene was rated as 3 points.
As a result, the softness and juiciness of the meat improved with an increase in the amount of olive fruit-derived oleanane-type triterpene (pentacyclic triterpene) adhering to the squid fillet. The trend of improvement was equivalent to that of the deep-fried chicken of Test Example 1 and the beef steak of Test Example 3.

５ＴＴは五環性トリテルペンの略である。
ＯＴＴはオレアナン型トリテルペンの略である。
＊：まぶし粉１００質量部当たりの含有量（質量部）である。
＊＊：イカ切り身１００質量部当たりの付着量（まぶし粉５質量部当たりの含有量、単位は質量部）である。 Table 4

5TT is an abbreviation for pentacyclic triterpene.
OTT is an abbreviation for oleanane-type triterpene.
*: Content (parts by mass) per 100 parts by mass of dust powder.
**: Attachment amount per 100 parts by mass of fillet of squid (content per 5 parts by mass of glazing powder, unit: parts by mass).

<Test Example 5 Effects of pentacyclic triterpenes on the texture of various fried chicken>
Fried chicken was produced in the same manner as in Test Example 4 using beef fillet, duck fillet, horse mackerel fillet, scallop adductor muscle, and vannamei shrimp as fried seeds. As in the case of the squid fillets, the tenderness and juiciness of the meat improved with an increase in the amount of oleanane-type triterpenes (pentacyclic triterpenes) derived from olive fruits.

<Production Example 7 Production of pentacyclic triterpene powder 3>
(1) The apple peel was peeled off from the apple fruit and put into a desktop mixer to obtain a pulverized apple peel.
(2) A pentacyclic triterpene powder 3 was obtained according to Production Example 2, except that pulverized apple peel was used as the starting material.
(3) When the obtained pentacyclic triterpene powder 3 was subjected to HPLC analysis (HPLC chart is omitted), the content of ursane-type triterpene was 90% by mass and the content of ursolic acid was 90% by mass.

<Test Example 6 Effect of ursan-type triterpene on the texture of fried chicken>
A marinate liquid was prepared according to Production Example 3 except that the pentacyclic triterpene powder of the parts by weight shown in Table 5 was used, fried chicken was produced according to Production Example 4, and evaluated according to Evaluation Example 1. Therefore, fried chicken was produced. and evaluated according to Evaluation Example 1. Table 5 shows the results. Examples 2 and 3 are repeated.
As a result, even when ursolic acid, which is a ursan-type triterpene, is used, the tenderness and juiciness of the meat are improved depending on the amount used. and 3 were almost equivalent.

５ＴＴは五環性トリテルペンの略である。
＊：鶏モモ肉片１００質量部当たりのタンブリング量（質量部）である。 Table 5

5TT is an abbreviation for pentacyclic triterpene.
*: Amount of tumbling (parts by mass) per 100 parts by mass of chicken thigh pieces.

From the above results, it is necessary to wait for elucidation of the action mechanism of the pentacyclic triterpene to improve the meat quality, but the lipophilic pentacyclic triterpene skeleton and It was considered that the amphipathic properties of the attached hydrophilic functional groups such as hydroxyl groups and carboxyl groups combined with the properties of the pentacyclic triterpene skeleton itself brought about the effect of improving meat quality. Since pentacyclic triterpenes generally have hydrophilic groups such as hydroxyl groups and carboxyl groups, it is assumed that all pentacyclic triterpenes have the effect of improving meat quality shown in this test example. inferred.

Claims (4)

A meat quality improving agent containing a pentacyclic triterpene. The meat quality improving agent according to claim 1, wherein the pentacyclic triterpene is one or more selected from the group consisting of oleanane-type triterpene, ursan-type triterpene, lupine-type triterpene and hopane-type triterpene. A method for improving meat quality, comprising the step of treating meat with the meat quality improving agent according to claim 1 or 2. A method for producing a processed meat food comprising the steps of treating meat with the meat quality improving agent according to claim 1 or 2 and heating the treated meat.

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