JPH0761927A - Lipase inhibitor and food and beverage containing the same added thereto - Google Patents

Abstract

PURPOSE:To obtain a lipase inhibitor, capable of effectively inhibiting a pancreatic lipase participating in the digestion and absorption of lipids in living bodies and contributing to the suppression or prevention of obesity and having high safety. CONSTITUTION:This lipase inhibitor contains flavonoids expressed by the formula (R<1> to R<3> are each H or OH), e.g. apigenin (all thereof are H) or myricetin (all thereof are OH) as an active ingredient. The flavonoids can directly be used or as a solution or a suspension prepared by diluting the flavonoids with a suitable solvent, further can be mixed with other additives and used as a powdery or a pasty form according to usual operation such as mixing or drying or suitably formulated into a pharmaceutical preparation and used as the lipase inhibitor or previously added and mixed with a food and a beverage, etc., for use. The lipase inhibitor can be utilized for preventing the food and beverage, etc., from deteriorating and malodor from emitting due to the lipase.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a lipase inhibitor, and more specifically, it can effectively inhibit pancreatic lipase involved in digestion and absorption of lipids in vivo and contribute to suppression and prevention of obesity. High lipase inhibitor. Further, this lipase inhibitor can be used for preventing deterioration of foods and drinks and generation of malodor due to lipase.

[0002]

2. Description of the Related Art Lipase (pancreatic lipase) in humans
Is the first enzyme for digestion and absorption of lipids, and development of a drug for inhibiting or preventing obesity by inhibiting pancreatic lipase has already been attempted. Examples include anti-obesity and triglyceride reducing agents described in JP-A-55-98114, oxetanones described in JP-A-61-252663, and obesity-preventing agents described in JP-A-1-102022. can do.

For the same purpose, foods and drinks to which an inhibitor separated from cereals and beans is added (Japanese Patent Laid-Open No. 3426/1988).
No. 4) and a method for extracting an inhibitory substance from seeds rich in fat (JP-A-49-41580).

On the other hand, fodder plan
The tannins of t) are known to inhibit lipase (British J. Nutrition,
60 , 275 (1988)). In addition, proteins from soybeans, cereals, and radish seeds have been reported to inhibit this (Agric. Biol. Chem., 37 , 37) .
1225 (1973), Nurt. Rep. In
t. , 32 , 1107 (1985), Japan Food Manufacturers Association, 35, 430 (1988)). In addition, hemicellulose, wheat bran and the like (J. Food Sci., 49 ,
956 (1984), Am. J. Clin. Nut
r. , 42, 629 (1985)), phosphatidylcholine of radish seeds (Faculty of Agriculture, Meiji University, 73 , 9)
(1986)), myo-inositol (J. Food).
Sci. , 53 , 250 (1988)) and the like, and reports on lipase inhibition.

Regarding crude drugs, as extracts against microbial lipase, extracts of 14 kinds of crude drugs such as peony, oren, psyllium, button pie, ginkgo biloba, and tea have been disclosed (JP-A-64-90131). Also,
The results of investigating the lipase inhibitory action of various natural product extracts have been reported (Meiji University Faculty of Agriculture, Research Report, 6
9 , 15 (1985)).

Further, recently, a lipase inhibitor comprising a water extract of bell pepper, pumpkin, shimeji mushrooms, maitake mushrooms, hijiki, green tea, black tea, and oolong tea (JP-A-3-21987).
No. 2) and epigallocatechin gallate, which is a main component in green tea, are incorporated into the patent (JP-A-3-228664) concerning a lipid absorption-suppressing food.

On the other hand, regarding flavonoids, the effects of flavones on rat small intestinal α-glucosidase have been investigated for the purpose of preventing obesity and diabetes, and it has been reported that myricetin and synthetic flavones have an inhibitory effect. (Chem. Pharm. Bull., 34 ,
838 (1986)). In addition, for the purpose of preventing tooth decay,
Quercetin which is a flavonol is S. It has been reported to inhibit Mutans dextran sucrase (Agric. Biol. Chem., 48 , 214.
3 (1984)). In addition, the activity of glyoxalase I, which is involved in inflammatory reaction, was evaluated by quercetin, fisetin, morin,
Inhibition of flavonols such as myricetin (Agricultural Journal, 57 , 765 (1983)), and xanthine oxidase, which is considered to be involved in gout, against apigenin,
Inhibition of luteolin by flavones and some glycosides thereof and flavonols such as kaempferol and quercetin and their glycosides has been reported (Biopharmaceutical Journal, 41 , 116 (1987)). Others, yeast α
-Glucosidase (Agric. Biol. Che
m. , 48 , 1559 (1984)), and an action against alkaline phosphatase (Agricultural Journal, 54 , 171 (1980)).

Regarding the effect of flavonoids on lipase, only studies on soybean isoflavones have been reported, in which soybean isoflavone inhibits soybean germination lipase but weakly inhibits pancreatic lipase. Only (Bulletin of Kumamoto Women's University, 3
3 , 60 (1981)).

As described above, although there are many reports on flavonoids, there is no reference that the flavonoids of the present invention have a lipase inhibitory effect.

[0010]

The present invention controls digestion and absorption of lipids in vivo and exhibits a remarkably high inhibitory effect on pancreatic lipase, which is a key to obesity. It is an object of the present invention to provide a highly safe lipase inhibitor that can contribute to prevention and can be used for preventing deterioration of foods and the like caused by lipase and generation of malodor, and foods and drinks to which the lipase inhibitor is added.

[0011] As a result of extensively searching for a highly safe natural component for a component having an inhibitory effect on lipase activity for many years, it has been found that the flavonoids represented by the formula (1) have a high lipase inhibitory effect.

[0012]

According to the present invention, the formula (1) is used as an active ingredient of a lipase inhibitor.

[0013]

[Chemical 2]

There is provided a lipase inhibitor characterized by containing flavonoids represented by the formula: wherein R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydroxyl group. It

These flavonoids can be used individually or as a mixture of several kinds. In addition, these flavonoids can be used as they are or as a solution or suspension diluted with an appropriate solvent. Furthermore, it can be used in the form of powder or paste by mixing with other additives by a usual operation such as mixing and drying.

These flavonoids can be used as a lipase inhibitor after being appropriately formulated. In addition, it can be used by adding it to foods and drinks and mixing it in advance. Furthermore, these flavonoids can be appropriately glycosylated before use.

[0017]

[Effect] These flavonoids have a higher inhibitory effect than epigallocatechin gallate, which is a green tea ingredient which is said to have a higher lipase inhibitory effect than before, and is a highly safe lipase inhibitor because it is derived from natural plants. Can be provided.

These lipase inhibitors can be used for obesity prevention based on the inhibition of digestion and absorption of fats and oils, and can be used for preventing deterioration of foods and the like and generation of malodor due to lipase.

[0019]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples.

Example 1 (Method for measuring lipase activity ) Lipase activity was measured by using 4-methylumbelliferone oleate (4-MUO), which is a fluorescent substance, as a substrate. This was done by measuring the fluorescence of beryferon.

In a small test tube, 100 μl of 4-MUO suspension which is a substrate, and porcine pancreatic lipase (manufactured by Sigma) solution 5
Take 0 μl and 50 μl of buffer, and finally 4-MUO
0.05 mM, porcine pancreatic lipase 2.2 μg, Mclv
20 at 37 ° C under the condition of aine buffer (pH 7.4)
Let react for minutes. The reaction was stopped by adding 1 ml of 0.1 N hydrochloric acid, and 2 ml of 0.1 M sodium citrate was added to adjust the pH of the solution to around 4.3, and then fluorescence of 4-methylumbelliferone produced by the reaction (Excitation wavelength 3
20 nm, fluorescence wavelength 450 nm) was measured with a fluorimeter.

Example 2 (Measurement of lipase inhibitory effect) The inhibitory effect of the sample on the lipase activity was measured by adding the sample to the lipase activity measuring system shown in Example 1 and allowing the reaction to examine the effect on the activity. I went by.

Each sample contained 50% tetrahydrofuran (T
HF) and dissolved in the reaction system shown in Example 1
Instead of 5 μl of aine buffer, 5 μl of 50% THF solution of the sample was added and reacted. Control is 50% TH
5 μl of F was added and reacted in the same manner. The inhibitory activity is
Amount of added sample (IC
₅₀ (μg)).

Example 3 (Inhibitory effect of flavonoids) The inhibitory effect of the flavonoids of the present invention on lipase was examined according to the above-mentioned Example. The results are shown in Table 1.

[0025]

[Table 1]

[0026]

[Chemical 3]

It is known that epigallocatechin gallate, which is the main component of green tea, has a high lipase inhibitory effect, but the flavonols of the present invention have a significantly higher inhibitory effect than epigallocatechin gallate. It was

[0028]

INDUSTRIAL APPLICABILITY According to the present invention, it exerts a remarkably high inhibitory effect on pancreatic lipase, which controls digestion and absorption of lipids in vivo and plays a key role in obesity, and inhibits this to suppress or prevent obesity. Provided is a highly safe lipase inhibitor which can contribute to the deterioration of foods and the like caused by lipase and the prevention of offensive odor.

The lipase inhibitor containing flavonoids as an active ingredient according to the present invention has a higher lipase inhibitory effect than the green tea ingredient epigallocatechin gallate, which has a known lipase inhibitory activity, and inhibits the action of the digestive enzyme lipase, It is possible to suppress digestion and absorption of lipids and prevent obesity due to fat intake. .

The lipase inhibitor containing flavonoids as an active ingredient according to the present invention does not have a marked astringency like epigallocatechin gallate and can be added or blended without deteriorating the taste of food or the like. In addition, it is a highly safe lipase inhibitor that is contained in a small amount in vegetables and drinks that are ingested daily. Further, it can be used for preventing deterioration of foods and generation of malodor due to lipase.

Front Page Continuation (72) Inventor Susumu Shimura 1-23-6 Numakage, Urawa-shi, Saitama (72) Ino Yoshio 3-26-11 Noshio, Kiyose-shi, Tokyo

Claims (2)

[Claims] 1. A compound represented by the formula (1): (In the formula, R ¹ , R ² and R ³ each independently represent a hydrogen atom or a hydroxyl group.) A lipase inhibitor characterized by containing a flavonoid. 2. A lipase inhibitor according to claim 1 is added,
Food and drink characterized by being mixed.