JP2002095415A - Method for producing theaflavins - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing theaflavins in a state in which only a part of catechins are oxidized and the cetechins can remain in an extract of green tea, which is a method for producing an extract of green tea containing both components of catechins and theaflavins in high contents since catechins contained in green tea are approximately wholly oxidized into theaflavins, or the like, in the fermentation process of oolong tea and black tea production. SOLUTION: An extracted solution of oxidases of various kinds of polyphenol- containing plants is mixed with an extracted solution of green tea and sufficiently stirred so that an oxidation reaction of (production of theaflavins) of catechins different from a fermentation process of tea is made possible. A theaflavin-containing extract of green tea having a flavor of various kinds of plants can be produced in a state of remaining flavor of green tea and catechins.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a theaflavin which oxidizes catechins to theaflavins by mixing various plant extracts with a green tea extract having a low theaflavin content and by the action of an oxidizing enzyme contained in the various plant extracts. It relates to a manufacturing method. Further, the present invention relates to a green tea extract containing both theaflavins and green tea catechins obtained by the present production method.

[0002]

2. Description of the Related Art Theaflavins are produced in oolong tea (semi-fermented tea) and especially in black tea (completely fermented tea) because they are produced by the action of oxidizing enzymes in tea leaves during the fermentation process of tea leaves. Green tea which is unfermented tea and its extract do not contain theaflavins.

[0003] In oolong tea, which is a semi-fermented tea, and black tea, which is a fermented tea, the content of catechins contained in green tea at a high content is extremely low. In recent years, green tea catechins have been found to have various physiological activities, and are attracting attention as new functional substances.

[0004] For example, antioxidant action (JP-A-4-2026)
2), growth inhibitory action of intestinal harmful bacteria (Japanese Patent Laid-Open No. 2-2959)
23), hypoglycemic action (JP-A-4-253918), plaque formation inhibitory action (JP-A-3-86814), anti-periodontal disease and halitosis prevention effect (JP-A-3-218320), sucrase activity inhibitory action (JP-A-5-218320) -17364), a bifidobacterial growth-promoting action (JP-A-5-339117), a hyaluronidase activity inhibitory action (JP-A-6-93931), and the application to various foods is currently being carried out. .

[0005] Theaflavins have also been found to have characteristic physiological activities compared to the physiological activities of catechins.

For example, sugar absorption suppression (Honda et al. Biosc
i. Biothech. Biochem. 57, 123, 1993. Hara et al. A
gric. Biol. Chem., 54, 1939, 1990), antibacterial activity against B. pertussis (Horiuchi et al., Infectious Diseases, 66, 559, 1992),
Inhibition of dental plaque formation (JP-A-6-263646, Hattori
Chem. Pharm. Bull., 38, 717, 1990), sucrose activity inhibitory action (JP-A-5-17352), and the like.

As described above, catechins and theaflavins each have a remarkable physiological activity.
Green tea contains only catechins, and fermented tea (oolong tea or black tea) contains theaflavins, but the content of catechins is low. Green tea leaves and fermented tea leaves (oolong tea leaves or black tea leaves) are mixed or extracted, or green tea extracts and fermented tea extracts are mixed, but both catechins and theaflavins are contained in green tea and fermented tea. There is a side that the flavor of each tea is offset and lost, and it is not preferred as a food material.

[0008]

SUMMARY OF THE INVENTION The present invention oxidizes only a part of catechins to produce theaflavins without impairing the flavor of green tea, and contains both catechins and theaflavins in high content. Produce green tea extract. By using extracts such as fruits and herbs as a supply material of oxidase that oxidizes catechins, their flavor is added, and a new green tea extract that is expected to have the functionality of both catechins and theaflavins It is intended for manufacturing.

[0009]

Means for Solving the Problems The present invention has been intensively studied in order to achieve the above object, and as a result, the fruits, immature fruits, leaves,
After adding water to the stem, roots or fruiting bodies, crushing the mixture, filtering, the obtained extract is mixed with water in which epicatechin and epigallocatechin are dissolved, and vigorously stirred at room temperature for 5 hours. It has been found that theaflavin is produced. Further, the present inventors have found that theaflavins are produced by mixing the above various plant extracts with the decocted green tea extract and stirring vigorously for 3 to 5 hours, thereby completing the present invention.

The present invention has been made based on the above findings, and is characterized in that theaflavins are produced by mixing various plant extracts with a green tea extract and stirring vigorously for 3-5 hours. The present invention relates to a method for producing theaflavins. Further, the present invention relates to a green tea extract containing theaflavins obtained in the process of the method.

[0011]

The plant extract containing polyphenol generally contains polyphenol oxidase. Plant oxidases oxidize polyphenols contained in each plant, but also oxidize polyphenols of other plants. Depending on the substrate specificity of the enzyme, although the oxidation reaction is weak or strong, enzymes that oxidize green tea catechins can be obtained from various plants such as fruits, vegetables and herbs. Different plants (due to different oxidases) result in different reaction product patterns than the oxidative reactions that take place during the tea fermentation process. The various plant extracts tested this time have the characteristic that the catechins remain and the theaflavins are produced by the action of oxidizing a part of the green tea catechins to produce theaflavins. Since the raw extracts of these plants are reacted at room temperature, theaflavins, which are oxidized derivatives of catechins, can be produced without impairing the flavor of green tea, unlike the production process of fermented tea.

[0012]

Preferred Embodiments Theaflavins obtained by the present invention are represented by the following formula 1, and are dyes having a unique benzotropolone ring.

Embedded image R1 and R2 are H, galloyl group and the like. It is produced by oxidative condensation between the B rings of the catechins shown in Chemical formula 2.

Embedded image R3 is H, galloyl group, etc., R4 is OH or H.

In the present invention, the tea (Camellia sinensis, C)
amellia sinensis var.assamica) is a raw or dried product of powder and tea waste produced by the leaves and the manufacturing process or heating,
Refers to a work that has undergone a kneading operation. Fruits and vegetables include various tissues such as loquat, pear, grape, strawberry, avocado, buckwheat, lotus root, and other mature and immature fruits of the plants shown in Table 1 and fruited fruits.

[Table 1] Plants that synthesize theaflavins and theaflavin production

The extract of various plants of the present invention is prepared by adding 1 to 100 times, preferably 2 to 5 times by weight of water to a plant and leaving it at room temperature for 1 to 3 days, preferably a blender ( Crushed using a mixer) and centrifuged or filtered with a filter paper, a filter, preferably gauze (1-5 fold) or the like.

Hereinafter, the present invention will be described in detail with reference to examples. However, the technical scope of the present invention is not limited by these examples.

EXAMPLE 1 20 different plants (100 g, fresh weight)
The mixture was mixed with 0 ml of water, crushed by a blender, and filtered with quadruple gauze to obtain a plant extract. 5 mg of epicatechin and 5 mg of epigallocatechin were dissolved in 0.25 ml of water while heating, cooled to room temperature, and mixed with 1.5 ml of the above plant extract. The mixture was vigorously stirred for 5 hours (mixing air essential for the progress of the reaction), and then filtered by adding 5 ml of acetone. After concentrating the filtrate, it was made up to 5.0 ml with aqueous methanol and analyzed by HPLC. HPLC conditions are column: Cosmos
il 5C18-AR, solvent: 10% → 30% (30min) → 75% (15min) CH
3CN. Table 1 shows the amount of theaflavin produced by each plant using the tissues (fruits, immature fruits, leaves, rhizomes, roots) of various plants including tea as the material and the amount of theaflavin produced when the tea leaves were used as 1. Indicated.

[0016]

Embodiment 2 An embodiment of loquat is shown below. Loquat pulp (1
(00 g, fresh weight) was mixed with 50 ml of water, crushed by a blender, and filtered with quadruple gauze to obtain a loquat extract. 30 ml of the extract is mixed with 100 ml of green tea extract
(10 g of dried green tea infused with 1000 ml of water) and stirred vigorously at room temperature for 3 hours (mixing air essential for the progress of the reaction). The resulting mixture was filtered through a membrane filter and analyzed by HPLC (FIG. 1). Theaflavins (three types of theaflavins and their galloyl esters)
Generation was confirmed. The production amount of theaflavins and the residual ratio of green tea catechin (eg, epigallocatechin 3-O-gallate) can be arbitrarily adjusted by adjusting the amount of the plant extract to be added, the reaction time, and the amount of air.

[0017]

EXAMPLE 3 FIG. 2 shows chromatograms of ripe and unripe loquat fruits, which were obtained in the same manner as in Example 2 above.
Fig. 3 shows the chromatograms of the moon) and the blank (mandarin orange juice only).
Shown in The chemical structural formula of GT-45 in FIG.

Embedded image

[0018]

Example 4 An example of isolating theanaphthoquinone and theaflavin from loquat is shown below. 200g of loquat pulp with water
The mixture was crushed with a blender together with 300 ml, and filtered with quadruple gauze. 300 ml of the filtrate was added to a solution of 1 g of epicatechin and 1 g of epigallocatechin in 50 ml of water, and the mixture was vigorously stirred at room temperature for 5 hours. After adding 1 liter of acetone to the reaction solution, suction filtration was performed with filter paper. The filtrate was concentrated with a rotary evaporator to remove acetone, and the remaining aqueous solution was extracted three times with ethyl acetate. The ethyl acetate extract was concentrated and then subjected to Sephadex LH-20 column chromatography, and eluted with ethanol to obtain 200 mg of theanaphthoquinone and 650 mg of theaflavin. This reaction mode is shown in FIG.
Shown in

The theaflavins-containing green tea extract produced according to the present invention has the antioxidant and antibacterial properties of green tea catechins.
Functionality of both components, such as deodorization and the like, and the inhibitory effect of theaflavins on dental caries formation are expected. In addition, this extract is a new green tea extract in which fruit flavor, herb flavor, vegetable flavor, etc. are added in addition to green tea flavor, depending on the type of plant used in the manufacturing process. Applications in the food field are expected.

[0020]

The present invention is characterized in that it provides a new material which contains both catechins of green tea and theaflavins of fermented tea (oolong tea and black tea) while retaining the green tea flavor. In addition, the use of extracts such as tea, fruits, vegetables, herbs, and the like for the production of theaflavins allows the flavors of these various plants to be added. The obtained material can be used in various forms, such as a dry powder, a gel, and a solid molded product, in addition to the extract (liquid).

The method for producing theaflavins of the present invention does not use a dangerous substance such as an organic solvent, is simple in operation, and has high practicality. Further, the obtained green tea extract is expected to be widely applied in the fields of food and medicine, and greatly contributes to promotion of human health.

[Brief description of the drawings]

FIG. 1 shows a high performance liquid chromatogram (HPLC) of loquat as a material in Example 2.

FIG. 2 shows a high performance liquid chromatogram (HPLC) when loquat is used as a material in Example 3.

FIG. 3 shows a high performance liquid chromatogram (HPLC) in the case of using orange as a material in Example 3.

FIG. 4. Formation reaction of theanaphthoquinone and theaflavin

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[Procedure amendment]

[Submission date] September 26, 2000 (2009.2)
6)

[Procedure amendment 1]

[Document name to be amended] Drawing

[Correction target item name] All figures

[Correction method] Change

[Correction contents]

FIG.

FIG. 2

FIG. 3

FIG. 4

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Tomio Kato 1-3-3 Takagase Nishi, Saga City, Saga Prefecture F14 term (reference) 4B027 FB17 FC06 FK07 FK08 FK15 FP74 4B064 AE44 CA21

Claims (5)

[Claims] 1. A method for mixing a green tea extract with a plant extract containing an oxidase to induce catechins in the green tea extract to theaflavins, which are oxidized derivatives thereof,
A method comprising producing a green tea extract containing theaflavins. 2. The method for producing theaflavins according to claim 1, wherein the plants are tea, fruits, vegetables, herbs, spices, and wood. 3. The catechins are catechin, epicatechin,
The method for producing theaflavins according to claim 1, which is epigallocatechin, epicatechin gallate, epigallocatechin gallate, and proanthocyanidins containing these as a constituent unit. 4. The method for producing theaflavins according to claim 1, wherein the theaflavins are theaflavins, theanaphthoquinone and their gallate derivatives. 5. A theaflavins-containing green tea extract produced by the method according to claim 1.