JP2002226445A - Method for extracting capsaicinoid-like substance from cayenne - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for industrially advantageously extracting high- purity capsaicinoid-like substances from cayenne in high yield. SOLUTION: This method for extracting capsaicinoid-like substances comprises extraction treatment of cayenne especially a nonacrid-fixed breed thereof using carbon dioxide in or near the critical state as the extraction solvent in the presence of an adsorbent such as a silica gel. Preferably, yield can be increased by previously admixing the cayenne with oils and fats and extracting the objective substances therefrom.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for extracting capsaicinoid-like substances from pepper, and more particularly, to extracting pepper, especially a non-pungent fixed variety of pepper from supercritical or near-critical carbon dioxide. The present invention relates to a method for extracting a capsaicinoid-like substance, which is characterized by performing extraction using an agent.

[0002]

2. Description of the Related Art Pepper (Capsicum annuum L.)
It is a plant widely used worldwide as a food, spice and pharmaceutical ingredient. Up to the present, 14 kinds of pungent components, such as capsaicin and dihydrocapsaicin, have been isolated and determined in structure from pepper fruits, and are generally referred to as capsaicinoids. Capsaicin has a variety of physiological activities, such as enhancing appetite, salivary and gastric acid secretion, gastrointestinal peristalsis, and enhancing energy metabolism (Tawao Kawata, Kazuo Iwai: Enhancement of body heat production by spice components and its expression) In addition to Kikuchi, Kazuo Iwai and Nobuji Nakatani, “Food Function of Spice Ingredients”, Koseikan, 1989, pp. 97-129), its potential as a new type of analgesic has been reported. However, capsaicin has an intense pungency that is one of the attractions of capsicum ingestion, but its use is limited due to its strong pungency and painful effect, and its use as a food additive or medicament is quite limited. I have.

On the other hand, as a pepper with low pungency, "CH-19 sweet", a non-fixed fixed variety of pepper, selected from a mutant strain of a spicy variety obtained in Thailand and selected and fixed at an experimental garden at Kyoto University, is used. It is reported that capsaicinoids are scarcely contained and that capsaicinoid-like substances are contained in large amounts (Journal of the Horticultural Society, 58,
3, 601-607, 1989). The capsaicinoid-like substances are capsiate and dihydrocapsiate, and it has been shown that these capsaicinoid-like substances have an activating effect on immunity and an activating effect on energy metabolism (J. Agricultural and Food Chemistr).
y, 46, 5, 1695-1697, 1998, and JP-A-11-246478).

Japanese Patent Application Laid-Open No. H11-246478 discloses a method for extracting a capsaicinoid-like substance, in which the non-pungent fixed variety "CH-19 sweet" of pepper is extracted with ethyl acetate and the resulting extract is extracted. A method is described in which oleoresin from which ethyl acetate has been distilled off is purified by chromatography on silica gel.

[0005]

In the above-mentioned method for extracting capsaicinoid-like substances with an organic solvent, the pigment component of capsicum and capsaicin contained in trace amounts are also extracted together, so that the capsaicinoid-like substances can be extracted with high purity. In order to further purify, a complicated separation / purification step such as chromatography on silica gel is required. However, the capsaicinoid-like substance is decomposed in the separation / purification process such as extraction with an organic solvent and / or chromatography.
There is a problem that the capsaicinoid-like substance cannot be extracted in high yield.

Accordingly, an object of the present invention is to extract a capsaicinoid-like substance, such as capsiate or dihydrocapsiate, which does not have a spicy taste from a pepper, particularly a non-pungent fixed variety of pepper, with high yield, high purity and industrial advantage. Is to provide a way to

[0007]

Means for Solving the Problems The present inventors have made intensive studies on a method for extracting a capsaicinoid-like substance from a pepper, particularly a non-pungent fixed variety of pepper with high yield, high purity, and industrial advantage. As a result, this time, the non-pungent fixed varieties of hot peppers, especially hot peppers, are subjected to extraction treatment using carbon dioxide in a supercritical state or in the vicinity thereof as an extractant, especially in the presence of an adsorbent such as silica gel. As a result, it has been found that the capsaicinoid-like substance can be extracted with high yield, high purity and industrially advantageous, and the present invention has been completed.

Thus, according to the present invention, peppers,
Capsaicinoids, in particular, extracting a non-pungent fixed variety of pepper by using carbon dioxide in or near supercritical state as an extractant, preferably in the presence of an adsorbent such as silica gel. A method for extracting such substances is provided.

Hereinafter, the present invention will be described in more detail.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION There are no particular restrictions on varieties, production areas, etc. of capsicum that can be used in the present invention as long as they contain capsaicinoid-like substances. Preferably, the content of pungent components such as capsaicin is low. Low non-pungent fixed varieties are preferred. As the non-pungent fixed variety of pepper, for example, a non-fixed fixed variety of pepper "C
H-19 sweet "can be used, and any of the capsicum itself (untreated product), a dried product thereof dried by an appropriate drying means such as freeze-drying, and a pulverized product thereof can be used. A dried and pulverized product can be preferably exemplified from the viewpoint of the extraction efficiency of the similar substance.

The above-mentioned extraction of capsicum, particularly the non-pungent fixed variety of capsicum, with carbon dioxide in a supercritical state or in a state close to the supercritical state (hereinafter abbreviated as supercritical carbon dioxide) is carried out using supercritical carbon dioxide. It can be carried out according to an extraction method known per se. Generally, about 70
C. or less and about 40 MPa or less, especially about 20 to about 6 MPa.
It is preferred to perform the extraction operation using carbon dioxide at a temperature in the range of 0 ° C. and a pressure in the range of about 7 MPa to about 30 MPa.

In the present invention, when the pepper is extracted with supercritical carbon dioxide, the extraction is preferably carried out in the presence of an adsorbent to adsorb and remove capsaicin, pigment components, wax components and the like present in trace amounts in the raw material. The purity of the desired capsaicinoid-like substance can be improved. Such adsorbent is not particularly limited, for example,
Porous substances having the ability to efficiently adsorb and remove the above-mentioned trace components such as silica gel, zeolite and porous resin can be mentioned, and silica gel is particularly preferred. Although the amount of the adsorbent is not particularly limited, it is usually about 1 to about 50% by weight, based on the weight of the pepper.
Preferably it can be in the range of about 2 to about 20% by weight.

[0013] In the present invention, the capsicinoid-like substance is added to and mixed with the pepper beforehand and extracted with supercritical carbon dioxide to improve the yield of the desired capsaicinoid-like substance and to decompose the capsaicinoid-like substance. It is effective to suppress. Examples of such fats and oils include vegetable oils such as soybean oil, rapeseed oil, coconut oil, rice oil, and corn oil; saturated fatty acids having 6 to 10 carbon atoms (for example, caprylic acid and capric acid) as main components. And medium-chain saturated fatty acid triglycerides composed of glycerin and the like, and the amount thereof is usually about 0.5 to about 0.5% based on the weight of pepper.
Preferred is about 50% by weight, especially in the range of about 1 to about 10% by weight.

Further, the extraction with supercritical carbon dioxide according to the present invention may optionally include the use of water,
Ethanol, methanol and the like can be used in combination.

To illustrate an embodiment of the present invention, first,
A non-pungent fixed variety of pepper is placed in an extraction tank, and medium-chain fatty acid triglyceride is added, if desired, and uniformly mixed. Furthermore, after charging an adsorbent such as silica gel if desired, supercritical carbon dioxide is supplied to the extraction tank to perform an extraction treatment. As described above, the extraction conditions are generally at a temperature of about 20 to about 60 ° C. and a pressure of about 7 MPa to about 30 MPa, preferably at a temperature of about 30 to about 40 ° C. and a pressure of about 10 MPa to about 20 MPa. Temperatures and pressures depending on the desired state of the carbon dioxide used can be employed. The extraction time can also be selected as appropriate,
Usually about 1 hour to about 50 hours, preferably about 3 hours to about 8
It can be within a time range. The supply amount of carbon dioxide is usually 0.5 to 20 g per 1 g of pepper.
/ H, preferably in the range of 3 to 10 g / h.

The extraction can be performed, for example, by continuously blowing carbon dioxide. After completion of the extraction, a carbon dioxide fluid containing a capsaicinoid-like substance is led to a separation tank, and a method commonly used in supercritical extraction, for example,
By adopting an appropriate separation means according to the extraction conditions, such as a method of lowering the pressure, a method of changing the temperature, an adsorption method in which an adsorbent for adsorbing the solute extracted in the separation tank is filled, and the like, The capsaicinoid-like substance as described above can be recovered. The separated carbon dioxide can be transported to a liquefaction tank and reused.

Since the capsaicinoid-like substance thus obtained does not substantially contain a pungent component such as capsaicin, a food additive or pharmaceutical having various physiologically active actions such as activation of energy metabolism and activation of immunity. Can be used as a component. For example, it can be used as a food additive or pharmaceutical ingredient for maintaining durability in continuous exercise, or as a non-narcotic analgesic.

[0018]

Next, the present invention will be described more specifically with reference to examples and comparative examples.

EXAMPLE 1 900 g of a freeze-dried pulverized product of the non-pungent fixed variety "CH-19 sweet" of pepper is charged into an extraction tank having a capacity of 5 liters, and supercritical carbon dioxide (extraction tank: pressure 10 MPa, temperature 40 ° C.). Extraction was performed for 5 hours while supplying a carbon dioxide supply amount of 5 kg / h). Next, the extraction gas is led to a separation tank,
Separation under the condition of temperature of 40 ° C. and pressure of 4 MPa in the separation tank,
9.4 g of extract was obtained (Product 1 of the present invention).

Example 2 An extract was prepared in the same manner as in Example 1 except that 90 g of silica gel (20% by weight based on the non-pungent fixed variety of pepper, "CH-19 sweet") was further charged. 5.4 g was obtained (Product 2 of the present invention).

Example 3 In Example 2, ODO (trade name of medium-chain saturated fatty acid triglyceride, manufactured by Nisshin Oil Co., Ltd.) 45
g (5% by weight based on the non-spicy fixed variety of pepper, "CH-19 sweet") was used.
The same treatment as in Example 2 was carried out except for adding and mixing "19 sweet" to obtain 30.1 g of extract (Product 3 of the present invention).

Comparative Example 1 1000 g of methanol was added to 100 g of a freeze-dried pulverized product of the same non-pungent fixed variety "CH-19 sweet" of pepper as used in Example 1 in a two-liter three-diameter flask, and heated to 40.degree. For 5 hours. After completion of the extraction, solid-liquid separation and filtration with filter paper were performed to obtain 850 g of an extract. Thereafter, methanol was recovered under reduced pressure to obtain 20.9 g of an extract (Comparative product 1).

Comparative Example 2 The procedure of Comparative Example 1 was repeated, except that the methanol was replaced with ethyl acetate, to obtain 14.4 g of an extract (Comparative Product 2).

Comparative Example 3 The procedure of Comparative Example 1 was repeated, except that hexane was used instead of methanol, to obtain 13.5 g of an extract (Comparative product 3). (Analysis of Extract) Capsaicinoid-like substances and capsaicin contained in the extracts of the extracts obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were analyzed under the following conditions. Is shown in Table 1 below. The capsaicinoid-like substance recovery rate in the table was determined by extracting the capsaicinoid-like substance in a freeze-dried product of the non-pungent fixed variety "CH-19 sweet" of pepper as a raw material by stirring and extracting three times with 6 times the amount of ethyl acetate. Using the extract as a sample and taking the value measured by the high performance liquid chromatography shown below as 100%,
The recovery rate was shown. Analysis conditions Column: ODS (4.6 × 150 mm) Solvent: 80% methanol Flow rate: 1 ml / min Detector: Fluorescence detector Ex = 280 mm, Em = 320
mm

[0025]

[Table 1]

As is evident from Table 1, the extract of the present invention showed a higher recovery of capsaicinoid-like substances than the comparative product. The product 2 of the present invention using silica gel
In the product 3 of the present invention, capsaicin contained in a trace amount in the raw material was completely removed.

[0027]

As described above, the capsaicinoid-like substance can be extracted from a red pepper with high yield, high purity and industrially advantageously by the extraction method of the present invention, which is extremely useful.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61P 3/02 A61P 3/02 29/00 29/00 37/04 37/04 C07C 233/20 C07C 233 / 20 // C07B 63/00 C07B 63/00 C (72) Inventor Katsuyoshi Matsukura 335 Karijuku, Hasegawa Kayori, Nakahara-ku, Kawasaki City, Kanagawa Prefecture Inside the Technical Research Institute (72) Inventor Shuichi Hashizume Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa Prefecture 2-1-1 Morinaga Confectionery Co., Ltd. (72) Inventor Masatoshi Kato 2-1-1 Shimosueyoshi, Tsurumi-ku, Yokohama, Kanagawa Prefecture Morinaga Confectionery Co., Ltd. (72) Inventor Yuko Setoguchi Tsurumi-ku, Yokohama, Kanagawa 2-1-1 Shimosueyoshi F-term in the laboratory of Morinaga Seika Co., Ltd. (reference) 4B018 MD15 ME02 MF01 4C088 AB48 AC04 BA37 CA10 CA13 CA28 NA14 ZA08 ZB09 ZC21 4H006 AA02 AD16 BB30 BD10 BD20 BJ50 BV34

Claims (5)

[Claims] 1. A method for extracting a capsaicinoid-like substance, comprising extracting pepper from supercritical or near-critical carbon dioxide as an extracting agent. 2. The extraction method according to claim 1, wherein the pepper is a non-pungent fixed variety. 3. The extraction method according to claim 1, wherein the extraction is performed in the presence of an adsorbent. 4. The extraction method according to claim 3, wherein the adsorbent is silica gel. 5. The extraction method according to claim 1, wherein the extraction is carried out after adding fats and oils to the pepper beforehand.