JP2015010083A - Method of producing ginger extract processed product - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method which makes it possible to efficiently produce a ginger extract processed product with improved content of shogaol in ginger extract.SOLUTION: A method of producing ginger extract processed product comprises the step of heating ginger extract in the presence of lactic acid at 110-150°C.

Description

  The present invention relates to a method for producing a processed ginger extract enriched with gingerol.

  Ginger (Zingiber officinale) contains pungent components such as gingerol, gingerone, and gingerol, and gingerol and gingerol have various pharmacological effects such as antioxidant action, blood circulation promotion action, and diabetes improvement action. It is known. In recent years, it has been reported that gingerol is preferable to gingerol in terms of pharmacological action such as imparting warmth and palatability.

  However, gingerol is very little contained in raw ginger, most of which is gingerol (mainly 6-gingerol). Therefore, conventionally, a method for enriching gingerol that increases the abundance ratio of gingerol in ginger has been studied. For example, a ginger extract is heated at a temperature of 100 to 150 ° C. for 0.5 to 5 hours ( Patent Document 1), heating Japanese pepper at a temperature of 70 to 95 ° C. for 1 to 150 hours (Patent Document 2), and the like have been reported. Moreover, it has been reported that a ginger extract is equilibrated and stabilized in a state containing a large amount of 6-shogaol by heating the ginger extract at 100 to 130 ° C. for 24 to 60 hours (Patent Document 3).

JP 2010-124786 A JP 2008-0779562 A JP 2012-50377 A

  The present invention relates to providing a method capable of efficiently producing a processed ginger extract with a higher content of gingerol in the ginger extract.

  The present inventors examined a method for enriching gingerol in a ginger extract. As a result, the ginger extract was heat-treated at 110 to 150 ° C. in the presence of lactic acid to convert gingerol to gingerol. It was found that a processed ginger extraction product in which ginger was promoted and conversion was performed without loss and the content of gingerol was further increased can be obtained efficiently.

That is, this invention relates to the manufacturing method of a ginger extract processed product including the process of heating a ginger extract at 110-150 degreeC in presence of lactic acid.
Moreover, this invention is a ginger extraction processed product manufactured by said method, Comprising: Ratio (B / A) of content of 6-shogaol (B) with respect to 6-gingerol (A) is 3 or more. , The ginger extraction processed product.

  ADVANTAGE OF THE INVENTION According to this invention, the ginger extraction processed material containing much 6-shogaol can be manufactured efficiently, without losing a raw material and a product. Since the processed ginger extract obtained by the method of the present invention contains a large amount of 6-shogaol, various pharmacological actions attributable to 6-shogaol can be more effectively exhibited.

The ginger used in the present invention means ginger (Zingiber officinale) which is a perennial plant of the ginger family. Such ginger is composed of rhizomes, stems, and leaves, but rhizomes are mainly used in the present invention.
The ginger may be raw or dried. Ginger can be used as it is during extraction, but it can also be used in the state of being crushed or ground down, or squeezed into juice.

  As a ginger extract, various solvent extracts extracted with ginger extracted at room temperature or under heating or using an extractor such as a Soxhlet extractor, extraction obtained by supercritical extraction such as supercritical carbon dioxide Product, its diluted solution, its concentrated solution or its dry powder.

  As the extraction solvent used for extraction, either a polar solvent or a nonpolar solvent can be used, and these can also be mixed and used. For example, water; alcohols such as methanol, ethanol, propanol and butanol; polyhydric alcohols such as propylene glycol and butylene glycol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; tetrahydrofuran and diethyl ether Linear and cyclic ethers such as polyethylene; polyethers such as polyethylene glycol; hydrocarbons such as hexane, cyclohexane and petroleum ether; aromatic hydrocarbons such as benzene and toluene; pyridines; fats and oils, waxes, other oils, etc. Of these, alcohols, water-alcohol mixtures, acetone, ethyl acetate, and hexane are preferable, and ethanol and acetone are particularly preferable.

Extraction conditions vary depending on the solvent to be used. For example, when extracting with ethanol or acetone, 1 to 100 parts by mass of solvent is used with respect to 1 part by mass of ginger, 0 ° C. to solvent boiling point, preferably 5 to 35 ° C. It is good to extract at the temperature of 0.5 hour-30 days, Preferably it is 1 hour-14 days.
Moreover, when performing supercritical extraction using carbon dioxide, the temperature and pressure when carbon dioxide is brought into a supercritical state can be appropriately adjusted. For example, 5 to 100 parts by mass of carbon dioxide is used per 1 part by mass of ginger, and the pressure is 7.1 to 50 MPa, preferably 7.1 to 30 MPa at a temperature of 31 to 100 ° C., preferably 31 to 50 ° C. Therefore, it is preferable to extract for 0.5 to 12 hours.

  The obtained ginger extract can be used as it is, but after the extract is diluted, concentrated or lyophilized, it can also be used in the form of powder or paste as necessary. In addition, inert impurities can be removed from the extract by a technique such as liquid-liquid distribution.

  The ginger extract thus obtained usually contains 4 to 35% by mass of gingerol (6-gingerol) based on the total amount of the extract, and gingerol (6-gingerol) is contained in the total amount of the extract. 1 to 10% by mass (see Reference Examples below).

In the present invention, the above-described ginger extract is subjected to a treatment of heating at 110 to 150 ° C. in the presence of lactic acid (hereinafter also referred to as “acid / heat treatment”).
By performing such treatment, conversion of 6-gingerol contained in the extract to 6-shogaol is promoted.

  As lactic acid used here, any of D-form, L-form, and DL-form may be used. Further, either natural lactic acid or synthetic lactic acid may be used. Considering utilization of the ginger extract of the present invention for food, it is preferable to use lactic acid used as a food additive.

  The amount of lactic acid to be used is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 30% by mass with respect to the ginger extract from the viewpoint of improving the production amount of 6-shogaol and suppressing decomposition product production. It is at most 20% by mass, more preferably at most 20% by mass. Moreover, Preferably it is 5-30 mass%, More preferably, it is 10-30 mass%, 5-20 mass%, More preferably, it is 10-20 mass%.

Although heating is performed at 110 to 150 ° C., the conversion rate from 6-gingerol to 6-shogaol is improved, and excessive reactions such as decomposition of 6-shogaol are suppressed. Therefore, it is preferably 140 ° C. or lower, more preferably 130 ° C. or lower.
The heating time can be appropriately set according to the reaction temperature, but is preferably 1 hour or longer, more preferably 5 hours or longer, preferably 10 hours or shorter, more preferably 9 hours or shorter. Moreover, it is 3-10 hours, 3-9 hours, 5-9 hours, 1-3 hours, etc.
From the viewpoint of improving the conversion rate, suppressing excessive reaction, and suppressing flavor deterioration, suitable heat treatment includes, for example, 3 to 9 hours at 110 to 130 ° C and 1 to 3 hours at 140 to 150 ° C.

The acid / heat treatment can be performed by appropriately adding water such as ion-exchanged water according to the state of the ginger extract.
In the acid / heat treatment of the present invention, the amount of water in the reaction system is preferably low from the viewpoint of 6-shogaol formation, and is 50% or less, more preferably 30% or less, more preferably 10% or less. More preferably, the content is 0 to 5%.
More specifically, when the heating temperature is 130 to 150 ° C., the moisture content is preferably 50% or less, and when the heating temperature is 110 to 130 ° C., the moisture content is preferably 10% or less.
From this point of view, it is preferable that the acid / heat treatment is performed in an open system rather than a closed system because moisture generated in the system is evaporated. It is also effective to positively remove moisture in the reaction system by nitrogen bubbling or the like.

  The ginger-extracted product thus obtained can be used as a crude product, but the added acid may be neutralized and removed, or the purity may be increased by appropriately combining known separation and purification methods. . Examples of the purification means include organic solvent precipitation, centrifugation, ultrafiltration membrane, high performance liquid chromatograph, column chromatograph and the like.

The ginger extract obtained in this way is promoted in conversion from gingerol to gingerol, converted without loss, and has a higher gingerol content. That is, the content ratio (weight ratio: B / A) of 6-shogaol (B) to 6-gingerol (A) in the processed ginger extract is 3 or more, preferably 8.5 or more, more specifically. Specifically, it is 3 to 100, preferably 8.5 to 50.
Moreover, it is preferable that content of 6-shogaol (B) in a ginger extraction processed material is 15 mass% or more, and it is more preferable that it is 16 mass% or more. Furthermore, from the viewpoint of reducing excess reaction, the total content (A + B) of 6-gingerol (A) and 6-shogaol (B) is preferably 16% by mass or more, and more preferably 17% by mass or more. Is more preferable.

  When the processed ginger extract of the present invention is used as a food, a pharmaceutical product, a quasi-drug, a cosmetic product, or the like, or may be used in combination with these, it may be used as an extraction processing solution or a fraction, but is suitable. It may be used as a diluted solution diluted with a solvent, or may be used as a concentrated extract or a dry powder, or prepared as a paste. Also, freeze-dry and dilute with a solvent usually used for extraction, such as water, ethanol, propylene glycol, butylene glycol, water / ethanol mixture, water / propylene glycol mixture, water / butylene glycol mixture, etc. It can also be used. It can also be used by encapsulating in vesicles such as liposomes or microcapsules.

  The processed ginger extract of the present invention can be used by adding to and blending with foods, pharmaceuticals, quasi drugs, cosmetics and the like. In this case, the processed ginger extract may be used alone, or oil, pigment, fragrance, preservative, chelating agent, pigment, antioxidant, vitamin, mineral, sweetener, seasoning, preservative, Used in various preparations such as foods, pharmaceuticals, cosmetics, quasi drugs, such as binders, extenders, disintegrants, surfactants, lubricants, dispersants, buffers, coating agents, carriers, and diluents. You may use it in combination with an additive, an excipient | filler, etc.

With respect to the above-described embodiment, the following aspects are disclosed in the present invention.
<1> A method for producing a processed ginger extract comprising a step of heating a ginger extract at 110 to 150 ° C. in the presence of lactic acid <2> 110 to 130 ° C. for 3 to 9 hours, or 140 to 150 ° C. The manufacturing method of said <1> heated for 1 to 3 hours.
<3> In <1> to <2>, the amount of acid used is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 30% by mass or less, based on ginger extract. Preferably it is 20 mass% or less. Moreover, Preferably it is 5-30 mass%, More preferably, it is 10-30 mass%, 5-20 mass%, More preferably, it is 10-20 mass%.
<4> The method according to <1> to <3> above, wherein the step of heating in the presence of lactic acid is performed in a state where the water content in the system is 50% or less.
<5> A ginger extraction processed product produced by the method of <1> to <4> above, wherein the ratio (B / A) of the content of 6-shogaol (B) to 6-gingerol (A) is The said ginger extraction processed material which is 3 or more.

<Material and test method>
(1) Ginger extract “Ginger Extract KOK-0002” (supercritical CO ₂ extract) manufactured by Fuji Flavor Inc. was used.

(2) Determination of gingerol and gingerol 50 mg of the extract was dissolved in methanol and made up to 10 mL. This was injected into a 10 microliter HPLC for analysis. For both 6-gingerol and 6-shogaol, quantitative values were calculated based on a calibration curve prepared using a 6-gingerol standard product (purchased from Wako Pure Chemical, purity 98.1%). The HPLC analysis conditions are as follows.

[HPLC analysis conditions]
Column: TSK-gel ODS 120T 4.6 × 250 mm 5 μm (Tosoh Corporation)
Flow rate: 0.5 mL / min
Temperature: 35 ° C
Detection: UV = 280 nm
Solvent: A = 0.1% formic acid aqueous solution, B = 0.1% formic acid acetonitrile solution Gradient program A / B = 70/30 → 10/90 (20 min) → 10/90 (10 min) → 70/30 (5 min)
Elution time of 6-gingerol: 19.0 minutes Elution time of 6-shogaol: 23.6 minutes

Reference Example 1 Quantification of 6-gingerol and 6-shogaol in ginger extract For ginger extract KOK-0002, 6-gingerol and 6-shogaol were measured according to the above quantitative method.
As a result, 6-gingerol was 16.3% and 6-shogaol was 4.5%.

Example 1
(1) DL-lactic acid (ACROS) 100 microliters was added to 1 g of ginger extract KOK-0002, and after stirring with a vortex mixer, it heated at 110 degreeC with the heat block, without plugging. After 1 hour, 3 hours, and 8.5 hours, vortex mixer stirring and centrifugation were performed to prepare an extraction product (Product 1 of the present invention).

Comparative Example 1
(1) Ginger extract KOK-0002 1 g of lactic acid was not added, and the same treatment as in Example 1 was performed to prepare an extraction processed product (Comparative product 1).

(2) Acetic acid (Kanto Chemical) 250 μL was added to 1 g of ginger extract KOK-0002 and treated in the same manner as in Example 1 to prepare an extraction-treated product (Comparative Product 2).

(3) To 1 g of ginger extract KOK-0002, 100 mg of DL-tartaric acid (Kanto Chemical) and 100 μL of ion-exchanged water were added and treated in the same manner as in Example 1 to prepare an extraction-treated product (Comparative Product 3).

(4) Ginger extract KOK-0002 1 g of lactic acid was not added, the heating temperature was 90 ° C., and an extraction-treated product (Comparative Product 4) was prepared in the same manner as in Example 1.

(5) Lactic acid was not added to 1 g of ginger extract KOK-0002, the heating temperature was 130 ° C., and the same treatment as in Example 1 was performed to prepare an extraction processed product (Comparative Product 5).

(6) Ginger extract KOK-0002 1 g of lactic acid was not added, the heating temperature was 150 ° C., and the same treatment as in Example 1 was performed to prepare an extraction treatment product (Comparative Product 6).

About this invention product 1 and comparative products 1-6, 50 mg was sampled, and 6-gingerol and 6-shogaol were quantified by HPLC. The results are shown in Table 1.
From Table 1, it was confirmed that the amount of 6-shogaol produced was improved when lactic acid was added.

Example 2
(1) To 1 g of ginger extract KOK-0002, 200 μL of DL-lactic acid (ACROS) was added and treated in the same manner as in Example 1 to prepare an extraction-treated product (Product 2 of the present invention).

(2) DL-lactic acid (ACROS) 100 μL and ion-exchanged water 100 μL were added to 1 g of ginger extract KOK-0002 and treated in the same manner as in Example 1 to prepare an extraction-treated product (Product 3 of the present invention).

(3) To 1 g of ginger extract KOK-0002, 200 μL of DL-lactic acid (ACROS) and 100 μL of ion-exchanged water were added and processed in the same manner as in Example 1 to prepare an extraction processed product (Product 4 of the present invention).

  About this invention products 2-4, 50 mg was sampled, and 6-gingerol and 6-shogaol were quantified by HPLC. The results are shown in Table 2 together with the results of the product 1 of the present invention.

Example 3
(1) DL-lactic acid (ACROS) 100 μL was added to 1 g of ginger extract KOK-0002, the heating temperature was set to 130 ° C., and the same treatment as in Example 1 was performed to prepare an extraction-treated product (Invention product 5). .

(2) DL-lactic acid (ACROS) 100 μL was added to 1 g of ginger extract KOK-0002, the heating temperature was 150 ° C., and the same treatment as in Example 1 was performed to prepare an extraction processed product (Invention product 6). .

(3) To 1 g of ginger extract KOK-0002, 100 μL of DL-lactic acid (ACROS) and 100 μL of ion-exchanged water are added, the heating temperature is set to 130 ° C., and the same treatment as in Example 1 is performed (the product of the present invention). 7) was prepared.

(4) Ginger extract KOK-0002 1 g of DL-lactic acid (ACROS) 100 μL and ion-exchanged water 100 μL are added and the heating temperature is 150 ° C. 8) was prepared.

Comparative Example 2
(1) 100 μL of DL-lactic acid (ACROS) was added to 1 g of ginger extract KOK-0002, the heating temperature was set to 90 ° C., and the same treatment as in Example 1 was performed to prepare an extraction processed product (Comparative Product 7).

(2) DL-lactic acid (ACROS) 100 μL and ion-exchanged water 100 μL are added to 1 g of ginger extract KOK-0002, and the heating temperature is set to 90 ° C. ) Was prepared.

About this invention products 5-8 and comparative products 7-8, 50 mg was sampled, and 6-gingerol and 6-shogaol were quantified by HPLC. The results are shown in Table 3 together with the results of the products 1 and 3 of the present invention.
From Table 3, it was thought that 110-150 degreeC was suitable for heating temperature from a viewpoint of reaction progress rate. Moreover, when heating at about 150 degreeC, it is thought that it is preferable that reaction time shall be 1-3 hours.

Example 4
(1) Ginger extract KOK-0002 1 g of DL-lactic acid (ACROS) 100 μL and ion-exchanged water 250 μL are added and the heating temperature is 130 ° C. 9) was prepared.
(2) DL-lactic acid (ACROS) 100 μL and ion-exchanged water 500 μL are added to 1 g of ginger extract KOK-0002, the heating temperature is set to 130 ° C., and the same treatment as in Example 1 is performed (extracted product) 10) was prepared.

About this invention products 9-10, 50 mg was sampled, and 6-gingerol and 6-shogaol were quantified by HPLC. The results are shown in Table 4 together with the results of the inventive products 1, 3, 5 and 7.
From Table 4, it was considered that a lower water content in the reaction system was preferable from the viewpoint of reaction progress rate.

Claims (5)

  The manufacturing method of a ginger extract processed product including the process of heating a ginger extract at 110-150 degreeC in presence of lactic acid.   The manufacturing method of Claim 1 heated at 110-130 degreeC for 3 to 9 hours, or 140-150 degreeC for 1 to 3 hours.   The manufacturing method of Claim 1 or 2 which uses 5-30 mass% of lactic acid with respect to a ginger extract.   The method according to any one of claims 1 to 3, wherein the step of heating in the presence of lactic acid is performed in a state where the water content in the system is 50% or less.   It is a ginger extraction processed product manufactured by the method of any one of Claims 1-4, Comprising: Ratio (B / A) of content of 6-shogaol (B) with respect to 6-gingerol (A) The said ginger extraction processed material which is 3 or more.