JPH11318377A - Extraction and production of sulfur-containing ingredient of garlic and production of oil and fat containing sulfur-containing ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for extracting and producing the sulfur-containing ingredients of garlic, capable of efficiently extracting and producing the pharmaceutically effective sulfur-containing compounds of the garlic. SOLUTION: This method for extracting and producing the sulfur-containing ingredients of garlic comprises adding 0-50 pts.wt. of water to 100 pts.wt. of garlic bulges, grinding the bulges, squeezing the ground product, controlling the juice to pH 6-8, adding an oil or fat to the juice, and subsequently leaving the mixture in a temperature range of 0-50 deg.C for 3 hr to 3 days to extract the sulfur-containing ingredients originated from the garlic in the oil or fat. The sulfur-containing ingredients contain two or more kinds of compounds among ajoene, propenylallyl thiosulfinate, methylallyl thiosulfinate, methyl ajoene and dithiin. When treating conditions are suitably selected, >=200 μg/g of ajoene, >=100 μg/g of the propenylallyl thiosulfinate, >=20 μg/g of the methylallyl thiosulfinate, >=20 μg/g of the methyl ajoene and >=300 μg/g of the dithin can be extracted in the oil or fat.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an extraction method for extracting and producing a sulfur-containing component from garlic under specific conditions, and a method for producing a sulfur-containing component-containing fat or oil.

[0002]

2. Description of the Related Art Garlic is a plant belonging to the genus Allium belonging to the family Lily and is widely used as a spice. Garlic is also known as a folk medicine, with atherosclerosis, pulmonary tuberculosis,
It has been widely used as a treatment for bronchitis, an antibacterial agent and an anthelmintic such as roundworm. The main causative agents showing these effects are allicin, propenyl allyl thiosulfinate,
It is a sulfur-containing organic compound such as methyl allyl thiosulfinate, ajoene, methyl ajoene, and dithiin. It has been reported that the inhibitory effect of ajoene on platelet aggregation is inhibited by garlic as a sulfur-containing drug. Lawson et al. Have reported the antibacterial action of thiosulfinates such as methylallyl thiosulfinate. The antibacterial properties of methylajoene have been reported by Yoshida et al. Nishimura et al. Reported that dithiin inhibits platelet aggregation.

[0003] The sulfur-containing compound in garlic exists as alkylcysteine sulfoxide, but is converted to allicin, methylallylthiosulfinate, propenylallylthiosulfinate, etc. by the action of alliinase. Ajoene, methyl ajoene, dithiin is the decomposition of allicin or allyl methyl thiosulfinate,
It is known to be formed by polymerization. With respect to the method for producing ajoene, the methods disclosed in JP-A-62-129224 and JP-A-8-84570 are known, but no report has been found on the comprehensive extraction and formation of sulfur-containing components.

[0004]

DISCLOSURE OF THE INVENTION The present invention has been made based on the above facts, and an object of the present invention is to mix a slicing liquid of garlic with an oil or fat to thereby obtain a sulfur-containing medicinal compound in the oil or fat. An object of the present invention is to provide an extraction generation method for efficiently extracting and generating.

[0005]

According to a first aspect of the present invention, there is provided a method for extracting and producing a sulfur-containing component of garlic, wherein 0 to 50 parts by weight of water is added to 100 parts by weight of a garlic bulb to pulverize, and the pulverized product is crushed. By squeezing, the pH of the squeezed liquid is adjusted to 6-8, fats and oils are added to the squeezed liquid, mixed, and maintained at a temperature of 0-50 ° C for 3 hours to 3 days, whereby the sulfur-containing component is contained in the fats and oils. Is extracted and generated.

According to a second aspect of the present invention, there is provided the method for extracting and producing a sulfur-containing component of garlic according to the first aspect, wherein the sulfur-containing component is ajoene, propenyl allyl thiosulfinate, methyl allyl thiosulfate. Nate,
It is characterized by being at least two of methyl ajoene and dithiin.

According to a third aspect of the present invention, there is provided a method for extracting and producing a sulfur-containing component of garlic according to the first or second aspect, wherein the amount of the sulfur-containing component extracted into fats and oils is ajoene. 200 μg / g or more, propenyl allyl thiosulfinate 100 μg / g or more, methyl allyl thiosulfinate 20 μg / g or more, methyl ajoene 20 μg / g or more, and dithiin 300 μg / g or more.

According to a fourth aspect of the present invention, there is provided a method for producing a sulfur-containing component-containing fat or oil, which comprises adjusting the sulfur-containing component-containing fat or oil according to any one of the first to third aspects. .

[0009]

Embodiments of the present invention will be described below in detail. Garlic used as a raw material when carrying out the method for extracting and producing a sulfur-containing component of garlic according to any one of claims 1 to 3 or the method for producing a fat-and-oil containing a sulfur-containing component according to claim 4, is arium Sativam L ( Alliu
m sativum L), which means its bulb here. The raw garlic, regardless of its form, such as raw, cryopreserved and dried products, as long as the active ingredients, alkyl cysteine sulfoxide and alliinase (EC 4.4.1.4.), Are sufficient. All can be used.

Ajoene in the present invention is (E, Z)-
4,5,9-trithiaddeca-1,6,11-triene-9-oxide, and propenyl allylthiosulfinate is (E, Z) -4,5-dithiaocta-2,
7-diene-5-oxide, methylallylthiosulfinate is 2,3-dithiahex-5-monoene-3-oxide, and methylajoene is (E,
Z) -4,5,9-Trithiadeca-1,6-diene-9
-Oxide, and dithiin is 3-vinyl-4H-
1,2-dithiin and 2-vinyl-4H-1,3-dithiin.

The garlic can be crushed by any method such as grinding and shredding, but in order to increase the amount of juice and obtain a sulfur-containing compound efficiently, an appropriate amount of water is added to the garlic. Fine grinding is effective. The method of pulverization is not particularly limited, and for example, a food processor, a homogenizer, or the like can be used.

However, if the amount of water is large, the pulverization efficiency is improved, but the yield of sulfur-containing components may be reduced. For example, the amount of the extracted product in fats and oils is 200 µg / g of Ajoene.
Above, methyl allyl thiosulfinate 20 μg / g or more, propenyl allyl thiosulfinate 100 μg / g
g or more, methyl ajoene 20 μg / g or more, dithiin 3
In order to extract and generate a concentration of at least 00 μg / g, the amount of water is preferably 50 parts by weight or less based on 100 parts by weight of garlic.

The method of squeezing subsequent to pulverization is not particularly limited, but it is convenient to use a juicer, a hydraulic press or the like.
When the pH of the squeezed liquid is lower than 6, the yields of ajoene, methylajoene and dithiin are particularly reduced, and when the pH is higher than 8, ajoene, methylallylthiosulfinate, propenylallylthiosulfinate, methylajoene and dithiin are obtained. Squeezed liquid has pH
Those adjusted in the range of 6-8 are suitable. Normally, the pH of the garlic juice is around neutrality of about 6.6 and usually does not require pH adjustment.

In order to extract and produce a sulfur-containing compound from the squeezed liquid, it is mixed with an oil or fat. The fat used is not particularly limited, and any of vegetable fats and oils, animal fats and oils, hydrogenated products thereof, and synthetic fats and oils can be used.

By mixing the squeezed liquid and the fat or oil, a sulfur-containing component derived from garlic can be extracted and produced in the fat or oil. At that time, the sulfur-containing compound can be extracted and produced in a relatively long time if kept at a low temperature, and in a short time if kept at a high temperature. For example, when the amount of extraction and production in fats and oils is
μg / g or more, methyl allyl thiosulfinate 20μ
g / g or more, propenyl allyl thiosulfinate 10
In order to extract and produce to a concentration of 0 μg / g or more, methyl ajoene 20 μg / g or more, and dithiin 300 μg / g or more, 50 ° C. for 3 days, 20 ° C. for 12 hours, 30 ° C. for 6 hours, and 30 ° C. Approximately 3 hours is a standard, but it is not limited because it changes depending on the amount of water added, pH of the juice, and the like.

In order to obtain a sulfur-containing component-containing fat or oil, it is necessary to separate water. For this treatment, a known treatment for oil-water separation may be employed. For example, when the sulfur-containing compound is allowed to extract and generate, the upper layer becomes an oil layer, which may be collected. Further, centrifugation or the like may be performed.

As described above, the method for extracting and producing sulfur-containing components of garlic according to the present invention makes it possible to stably obtain fats and oils containing a large amount of sulfur-containing components.

[0018]

The embodiments of the present invention will be described more specifically with reference to the following examples. It goes without saying that these examples do not limit the invention. In addition,
In the following examples, “% and part” mean “% by weight” and “part by weight” unless otherwise specified.

(Quantitative Analysis of Sulfur-Containing Components) First, before giving a specific example of the extraction and production of sulfur-containing components derived from garlic, the quantification of the sulfur-containing components will be described. Quantitative analysis of ajoene, methyl allyl thiosulfinate, propenyl allyl thiosulfinate, methyl ajoene and dithiin was performed as follows. That is, after centrifuging (5000 rpm × 10 minutes) 10 g of the sulfur-containing component extraction product fat, 2.5 g of the supernatant liquid
Was taken up, the volume was adjusted to 25 ml with dichloromethane, and the solution was filtered through a tetrafluoroethylene (PTFE) filter (0.2 μm, manufactured by Toyo Roshi Kaisha, Ltd.) to obtain a sample solution. Ajoene, methylallylthiosulfinate, propenylallylthiosulfinate, methylajoene, and dithiin standard were similarly dissolved in dichloromethane and analyzed by high performance liquid chromatography (HPLC) as a standard solution.

The measurement conditions are as follows. 3. Ajoene, methyl allyl thiosulfinate, propenyl allyl thiosulfinate, methyl ajoene Separation column: SUPELCOSIL LC-Si
6 (inner diameter) x 250 mm (manufactured by Spelco Japan Co., Ltd.) Eluent: hexane: isopropanol (95: 5) (V
/ V) Flow rate: 2 ml / min Detection wavelength: 240 nm

3. Dithiin separation column: SUPERCOSIL LC-18
6 (inner diameter) x 250 mm (manufactured by Spelco Japan KK) Eluent: acetonitrile: water: tetrahydrofuran (7
0: 27: 3) (V / V) Flow rate: 1 ml / min Detection wavelength: 240 nm

(Example 1, Comparative Example 1) To 500 g of raw garlic (6 pieces of white), 150 g of water was added, and a food processor (manufactured by Cuisinart, DLC-XP) was added.
(LUS type) and squeezed by hand using a nylon filter cloth to obtain 400 g of juice. From this, 80 g of each sample was taken to prepare 5 samples, of which 4 samples were each pH 5 with citric acid (Comparative Example 1-1) and pH 6 with citric acid.
(Example 1-1), pH 8 with sodium hydroxide
(Examples 1-3), pH 9 with sodium hydroxide
(Comparative Example 1-2), and one sample without adjustment (pH 6.5)
7, a total of five kinds of samples were prepared in combination with Example 1-3), and 80 g of medium-chain fatty acid fat (Panasate 810, manufactured by NOF CORPORATION) was added. Next, after mixing with a homomixer (M type, manufactured by Tokushu Kika Kogyo Co., Ltd.), the mixture was kept at 30 ° C. for 24 hours, and an analysis sample was prepared by the above-described procedure to analyze the sulfur-containing component.

The results are as shown in Table 1. From the results, p
It is understood that H is preferably 6-8 near neutrality.

[0024]

[Table 1]

Example 2 80 g of the squeezed juice obtained in the same manner as in Example 1 was taken for each of the four specimens, and 80 g of medium-chain fatty acid fat was added to each sample, mixed as in Example 1, and mixed at 0 ° C. , 2
It was kept at 0 ° C, 30 ° C, and 50 ° C to extract and generate sulfur-containing components. The pH of the juice was 6.59, and the pH was not adjusted. Samples were collected from these samples over time (3 hours, 12 hours, 1 day, 2 days, 3 days) and the components were analyzed in the same manner as in Example 1.

The results are shown in Tables 2 to 5, wherein the desired sulfur-containing component content can be obtained at 0 ° C. for 3 days and at 50 ° C. for 3 hours.

[0027]

[Table 2]

[0028]

[Table 3]

[0029]

[Table 4]

[0030]

[Table 5]

(Example 3) Raw garlic (6 pieces of white)
0 g, 25 g, 5 g
0 parts, crushed and squeezed as in Example 1 as 100 parts,
From each of these squeezed liquids, 80 g of each was taken as a sample, and 80 g of medium-chain fatty acid fat was added to each of them.
C. for 24 hours, and the components were analyzed. In addition,
The pH of the squeezed liquid was 6.58 for 0 parts of water, 6.59 for 25 parts of water, 6.59 for 50 parts of water, and 6.65 for 100 parts of water, and the pH was not adjusted. .

The results are shown in Table 6. The desired sulfur-containing component content can be obtained with 0 to 50 parts of water.

[0033]

[Table 6]

[0034]

As described above, according to the method of the first aspect, a sulfur-containing component derived from garlic which can be expected to have a pharmacological effect can be efficiently extracted and produced. According to the method of claim 2, a sulfur-containing component containing at least two of ajoene, methylallylthiosulfinate, propenylallylthiosulfinate, methylajoene, and dithiin is efficiently and comprehensively extracted. Can be generated.

Further, by selecting the processing condition,
As described above, the amount of sulfur-containing components extracted and extracted into fats and oils is 200 μg / g or more of ajoene, 100 μg / g or more of propenyl allyl thiosulfinate, 20 μg / g or more of methyl allyl thiosulfinate, and 20 μg / methyl ajoene /
g or more, and dithiin 300 μg / g or more.

According to the method for producing a sulfur-containing component-containing fat or oil according to the fourth aspect, a fat or oil containing a high ratio of a sulfur-containing component which can be expected to have a pharmacological effect can be efficiently obtained.

Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 31/095 ADZ A61K 31/095 AEC AEC 35/78 ACDV 35/78 ACD A23D 9/00 504

Claims (4)

[Claims] 1. A garlic bulb with 100 parts by weight of 0
-50 parts by weight of water is added and pulverized, the pulverized product is squeezed, the pH of the squeezed liquid is adjusted to 6-8, oil and fat are added to the squeezed liquid and mixed, and the squeezed liquid is mixed at a temperature range of 0-50 ° C. A method for extracting and producing a sulfur-containing component of garlic, wherein a sulfur-containing component is extracted and generated in the fat or oil by holding for 3 hours to 3 days. 2. The method according to claim 1, wherein the sulfur-containing component is at least two members selected from the group consisting of ajoene, propenyl allyl thiosulfinate, methyl allyl thiosulfinate, methyl ajoene, and dithiin. . 3. The amount of the sulfur-containing component extracted and extracted into the fat or oil is 200 μg / g or more of ajoene, 100 μg / g or more of propenyl allyl thiosulfinate, 20 μg / g or more of methyl allyl thiosulfinate, and methyl ajoene 2
The method for producing and extracting a sulfur-containing component of garlic according to claim 1 or 2, wherein the amount is at least 0 µg / g and at least 300 µg / g of dithiin. 4. A method for producing a sulfur-containing component-containing fat or oil which is prepared by the method for extracting and producing garlic according to any one of claims 1 to 3.