JP3142411B2 - Antioxidants and methods for producing antioxidants - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a food containing fats and oils,
The present invention relates to an antioxidant that can be used for improving the preservability of feed for livestock and fisheries, feed for pets, cosmetics, and the like.

[0002]

2. Description of the Related Art Fats and oils and fatty acids are easily oxidized by oxygen in the air, and the resulting oxides not only impair the flavor of foods but also cause food poisoning. Therefore, foods and cosmetics containing fats and oils are generally preserved under the condition of being shielded from oxygen as much as possible, while adding an antioxidant (antioxidant) to enhance the preservability.

Heretofore, natural products such as tocopherol and spice extracts have been used as antioxidants in addition to synthetic products such as BHT and BHA. However, although the synthetic product has a strong antioxidant effect, carcinogenicity and adverse effects on various internal organs are feared, and its frequent use is not preferable. Natural products are highly safe, but generally have poor antioxidant activity, and many have problems in taste, smell, color, solubility in water, etc., and have antioxidant properties for food and cosmetics. Considering the important properties of the agent comprehensively, few are satisfactory.

[0004]

In recent years, as the public interest in the safety of foods and cosmetics, which have a great influence on health maintenance, has been increasing, natural products of high safety and excellent in antioxidant action, taste An antioxidant that does not adversely affect the quality of the object to be added in terms of smell and smell has been strongly demanded. An object of the present invention is to provide an antioxidant capable of meeting such a demand and a method for producing the same.

[0005]

DISCLOSURE OF THE INVENTION The present invention has been completed based on the finding that a strong antioxidant action was found in a Salix extract as a result of screening a large number of plant extracts from the viewpoint of antioxidant action. The present invention provides an antioxidant containing, as an active ingredient, an extract (hereinafter referred to as "Salix edulis extract") obtained by extracting Salix edulis with water or a hydrophilic organic solvent or a mixture thereof .
The present invention also provides an antioxidant effect of the Salix
Quercetin sulfate identified as a causative agent of
Extract from Salix edulis and use it as the active ingredient
And a method for producing an antioxidant characterized by the following:
(Hereinafter, meaning including antioxidants obtained by this production method
In the "antioxidant of the present invention") .

[0006]

[Action] Salix (Polygonum hydropiper L.)
It is a plant of the family Polygonaceae, also known as the Polygonum and the Polygonum,
The sprout has been used for foods since ancient times, such as sashimi pinna and tadpole vinegar. It is known that the fat-soluble component of this plant contains an antibacterial substance such as polygodial and can be used as an antibacterial agent. Had not been. It is also known that quercetin sulfate is contained in willow extract and that quercetin sulfate isolated from the extract can exhibit a strong antioxidant effect and constitute an excellent antioxidant. Had not been. Quercetin sulfate dissolves up to about 150 mg in 100 ml of water, and within this solubility range, its antioxidant effect can be fully utilized.

[0007] The willow extract used in the present invention is obtained by extracting ground materials such as stem, leaves, roots and the like of waterweed with water or a hydrophilic organic solvent, or a mixture thereof. As the hydrophilic organic solvent used for the extraction, a lower alcohol such as methanol or ethanol, or acetone is particularly preferable. Extraction material is hexane,
It is desirable to extract with a non-polar organic solvent such as ether to remove the pungent components contained in the Salix. The extraction method is not particularly limited, and the extraction can be performed at any temperature from room temperature to around the boiling point of the extraction solvent.

The extract obtained by distilling the extraction solvent from the extract can be used as an antioxidant as it is,
Purification treatment for deodorization, decolorization, etc. may be performed as long as the antioxidant effect is not adversely affected. Furthermore, those that have been subjected to separation and purification treatments such as liquid-liquid distribution extraction, various types of chromatography, ion exchange, and membrane separation to increase the content of quercetin sulfate can be used as antioxidants that exhibit stronger effects. You. The antioxidant of the present invention is optionally used
Can be used in combination with other antioxidants .

The antioxidant of the present invention is to be added to an aqueous substance because the extract of Salix edulis is substantially water-soluble and quercetin sulfate is also completely soluble in water at a practical concentration as described above. In this case, it can be easily melted and used, and the usage efficiency is high. The antioxidant of the present invention can be used not only in foods containing fats and oils, feeds for livestock and marine products, feeds for pets, cosmetics and the like to improve storage stability, but also to produce these fats and oils containing foods and the like. Can also be used to prevent oxidation in the heat treatment step and the like.

The preferred addition rate of the antioxidant of the present invention to oil-containing products and the like depends on the quercetin sulfate content of the antioxidant to be used, the type of the substance to be added, the storage conditions, and the like. The extract is approx.
By adding 0.01 to 1.0% by weight (preferably about 0.1 to 0.5% by weight), and quercetin sulfate is added to about 0.001 to 1.0% by weight (preferably about 0.01 to 0.5% by weight).
(0.1% by weight) effectively prevents oxidation of fats and oils, and prevents generation of unpleasant tastes, smells, harmful oxides and the like.

[0011]

The present invention will be described below with reference to examples. The antioxidant activity in each example was measured by the following method according to the method of Mitsuda et al. (Nutrition and Food, Vol. 19, page 210, 1966). Antioxidant activity measurement method: 0.2 ml of a 10 ^-2 M ethanol solution of linoleic acid to which an antioxidant has been added is kept at 38 ° C for 4 days. Thereafter, 4.7 ml of 75% ethanol and 1 ml of a 30% rhodamon ammonium solution are added, and the mixture is stirred well. Further, 0.1 ml of a ferrous chloride reagent is added. After exactly 3 minutes, the absorbance at 500 nm is measured. Since the absorbance at 500 nm was determined by measuring the red color of hydroxy peroxide generated by the peroxidation of linoleic acid, the absorbance at 500 nm was evaluated as the peroxide value. The same operation was performed for linoleic acid without an antioxidant.

Example 1 100 g of the stem and leaf portion of Salix serrata was immersed in 1000 ml of hot water for 1 day, and the obtained extract was freeze-dried to obtain 6.1 g of Salix sativa extract (hereinafter referred to as an antioxidant). A.). Extraction was performed in the same manner except that 50% ethanol was used instead of hot water as the extraction solvent to obtain antioxidant B (yield 8.7 g). C (yield 7.6 g) was obtained. Further, a portion of the antioxidant B was fractionated and purified by column chromatography using ion exchange resin / diaion HP-20, silica gel, and Sephadex LH-20 sequentially to obtain quercetin sulfate. (1.72% yield). Table 1 shows the results of measuring the antioxidant activity of these antioxidants.

[0013] (The concentration of antioxidants in the linoleic acid solution is 200 ppm for all)

Example 2 0.02% of the antioxidant A or quercetin sulfate obtained in Example 1 was added to a mixture of lard and harm oil, and the mixed oil was heated to 145 ± 5 ° C. 200 g of molded ramen was fried for 2 minutes. For comparison, fried ramen was manufactured in the same manner as described above except that no antioxidant was added or tocopherol (purity 70%) or BHT was used. Immediately after production, each fried ramen was sealed in a bag made of polypropylene film and stored at 50 ° C. Immediately after production, and after 40 and 80 days of storage, a part of the above-mentioned fried ramen was taken, the fat and oil was extracted with ethyl ether, and the peroxide value of the extracted fat and oil was measured. Table 2 shows the results.

Table 2 Change in peroxide value by storage 40 days after production of antioxidant 80 days after addition No addition 2.5 31.5 165.0 Tocopherol 2.8 15.8 69.0 BHT 2.5 8.5 18 .5 Antioxidant A 3.0 7.5 18.0 Quercetin sulfate 2.8 4.5 8.2

Example 3 2.4 kg of pork (minced meat), 1.2 kg of lard (shredded), 1 g of sodium nitrite, 5 g of sugar, 5 g of granular pepper, 20 g of wine, and the antioxidant obtained in Example 1 Agent B0.
9 g were mixed. The obtained mixture was filled in a casing having a diameter of 3 cm and dried at 5 ° C. for 30 days to produce salami sausage. In addition, salami sausage was produced in the same manner as described above except that 0.5 g of quercetin sulfate obtained in Example 1 was used in place of antioxidant B. Further, a control product was prepared in the same manner as described above except that no antioxidant was added. A sensory test was carried out on the flavor of these sausages. The control product showed oil burns, whereas the antioxidant B or quercetin sulfate did not show such a taste. No undesired taste or smell due to the addition of the oxidizing agent was also felt.

Example 4 1 kg of anchovy was washed with water, and 1 g of a 5% saline solution containing 1.0 g of the antioxidant C obtained in Example 1 was added.
Boil at 95 ° C. for 0 minutes. Then, it dried with 30 degreeC warm air overnight, and manufactured the boiled-dried. This was stored in a polyethylene film bag at room temperature. Separately, a control product was prepared in the same manner as described above except that the antioxidant C was not added.
The peroxide value of these dried sardines was measured 10 days and 20 days after the production. Table 3 shows the results.

Table 3 Changes in peroxide value upon storage 40 days after production of antioxidant 80 days after addition No addition 2.7 56.9 150.5 Antioxidant C 2.6 12.3 18.5

[0019]

As described above, the antioxidant of the present invention exhibits excellent performance in antioxidant action comparable to that of a synthetic product. In addition, since quercetin sulfate contained in the extract of Salix edulis, which has been used for a long time, is an active ingredient, it has high safety and has almost no adverse effect on the flavor of food. Since quercetin sulfate is substantially water-soluble, even when the substance to be added is aqueous, it can be easily and uniformly mixed and has good utilization efficiency, which is an advantage of the antioxidant of the present invention. It is a point.

Continuation of the front page (56) References JP-A-1-179678 (JP, A) JP-A-59-75978 (JP, A) JP-A-63-21062 (JP, A) JP-A-60-208908 (JP, A) , A)

Claims (2)

(57) [Claims] An antioxidant comprising, as an active ingredient, an extract obtained by extracting Salix edulis with water or a hydrophilic organic solvent or a mixture thereof. 2. Quercetin sulfate extracted from Salix
Characterized by using acid esters as active ingredients
Manufacturing method of antioxidants.