JPS6343959A - Method for stabilizing anthocyanin dye - Google Patents

Abstract

PURPOSE:To contemplate an improvement in the problem with respect to the discoloration and fading of anthocyanin dyes, by bonding a sugar such as cyclodextrin to the hydroxyl groups in the glycoside moiety of an anthocyanin dye. CONSTITUTION:An anthocyanin dye is obtd. by bonding cyclodextrin or other sugars to the hydroxyl groups in the glycoside moiety of an anthocyanin dye. Examples of the sugars are starch, glycogen, disaccharides, monosaccharides, etc. At least mealy an equimolar amount of the sugar is used for the dye. The bonding of the sugar can be effected by bonding cyclodextrin or other sugars to the hydroxyl groups in the glycoside moiety of an anthocyanine dye in the presence of enzyme cyclodextringlycosyltransferase as a catalyst. The catalyst is an enzyme secreted from an bacterium of the genus Bacillus (e.g., B. macerans).

Description

[Detailed Description of the Invention] (Industrial field to which it belongs) This invention relates to pigments. In particular, it is an anthocyanin pigment that can be used for food, medicine, cosmetics, and general industrial purposes.

Here, anthocyanin pigments refer to anthocyanin pigments that have a glycoside moiety bound and retained in their molecules. Examples of such pigments include red-purple pigments originating from red cabbage, red-purple pigments originating from grape skins, and pigments originating from purple corn, berries, and others.

(Prior Art) Anthocyanin pigments have poor light resistance and heat resistance. Sara K
This substance is a water-soluble substance, and the higher the I)H of the aqueous solution system, that is, the higher the number, the greater the degree of loss of stability and discoloration and fading. These are the general drawbacks of anthocyanin pigments.

Here, the challenge for those skilled in the art is to find a method to prevent anthocyanin pigments from discoloring or fading, and to impart properties that are resistant to light and further resistant to heat, regardless of the size of the pH.

This invention is one answer to solving this problem.

The present invention will be explained in detail below.

(The Bottom of the Invention) Auxiliary agents for stabilizing anthocyanin pigments are carbohydrates and specific enzymes.

Carbohydrates that can be used include starch (regardless of its origin), glycogen, dextrin (which may be linear or cyclic), 2 tons, or monosaccharides. These may be used alone or in combination of two or more. The amount used is approximately equimolar or more relative to the anthocyanin pigment.

Next, the stabilization process will be explained. Anthocyanin pigments and carbohydrates are blended in the amounts used above to form an aqueous system. The amount of water used may be about 5 times or more the total weight of carbohydrates and anthocyanin pigments.

In this, Bacillus macerans (Bomaceran)
s), 7< f )V Smegatherium (331meg
aterium), Bacillus circulanne (73, c
The enzyme cyclodextrin glycosyltransferase (
Cyclo-dextrin glycosyltra
nsferase). While starch-digesting enzymes such as α-amylase mainly catalyze the hydrolysis of carbohydrates, this enzyme is responsible for the reaction that produces cyclodextrin from starch, and the reaction that produces linear chains from cyclodextrin and receptors. It catalyzes three actions: a reaction that produces oligosaccharides, and a reaction that disproportions the amount of linear oligosaccharides. The amount of this material added is 1 mo1 of anthocyanin pigment. Nidaishi, 1×1
0 units ('l”i Iden-1 (udson method)
It is enough. Furthermore, the temperature of this system may be below the inactivation temperature of this enzyme, approximately 60° C. for 24 hours.

In this way, the glucose part of the carbohydrate is
It binds to specific hydroxyl groups of glycosides of anthocyanin pigments. Specific refers to the hydroxyl group at the 4-position of glucose.

Completion of the reaction may be confirmed by liquid chromatography (see Figure 1).

In this way, the reaction is stopped when the binding of carbohydrates to anthocyanins is completely completed, and the system is purified, that is, unbound carbohydrates are removed. For this purpose, this system may be purified using an adsorption resin, ultrafiltration, or other methods. The desired stabilized anthocyanin pigment can be obtained by taking only the purified clear liquid, concentrating it, or drying it.

Here, the invention has achieved its purpose.

(Actions and Effects) (The target product D has excellent light resistance, heat resistance, acetic acid resistance, and alkali resistance. For details, refer to the examples described below.

(2) It is not necessary to deactivate the enzyme contained in the yarn after the binding of dextrin to the starting anthocyanin pigment has been completed. This is because the enzyme, which has completed its binding role, has no other function than for use in metastatic cattle.

Example 1 10V% red cabbage dye (E = 200) 1F, α-cyloclodextrin 1) was added to a pH = 6.0 buffer solution (0,0
1M% acetic acid/sodium acetate) 101) 1, then CGT-ase (470U/, vt/) 2 m
1 was added and left at 35-40°C for 10 hours. The obtained dye solution was purified with adsorbed linoleum (Diaion HP-40 Mitsubishi Kasei), E10v96=60f Te? ! )i sita.

1 Enzyme treated pigment! (T) and conventional red cabbage pigment (S
) E10v96 = 60 degrees, adjusted according to the prescription for soft drinks in plastic containers (see below), irradiated for 8 hours with a fade meter (FA-2 model, Nutambed Carbon Fade Meter, Suga Test Instruments), and 95° C. Heated for 60 minutes and compared both (T) and (S).

Prescription Soft drink sugar in a plastic container Sugar 150 (P) Isomerized sugar
62.5 Citric acid 2.5 The total amount was adjusted to 1000 (x/) with clean water.

As can be seen from the results below, (T) had improved heat resistance and light resistance, and little change in color tone.

0 Heat resistance and light resistance numbers indicate the dye residual rate.

*Fade meter abbreviation Example 2 10V%-Purple corn pigment (E-100) was applied to c
rn When treated with enzymes in the same manner as in Example 1, colored chewing gum pene, and irradiated with sunlight for 3 days in summer, the light resistance improved,
There was also little change in color tone.

Prescription: Gumbeine complex acid vinyl resin 200 (MeBPBG
(Softener) 30 Polyisobutylene 30 Microcrystalline wax 20 Carbonating power/Ressium 20 Powder Sugar
450 glucose
Example 3 10V% Grape juice pigment (E1., -40) was treated with enzymes in the same manner as in Example I, colored into candy, and exposed under fluorescent light. ,
When left for one week, both light resistance and color change were better than conventional grape juice pigments.

Prescription candy Sand 65o (Me Water, candy, 500 1.300 0 Light resistance The number indicates the dye residual rate

[Brief explanation of drawings]

Figure 1, Figure 2... Diagram Patent applicant: Sanei Chemical Industry Co., Ltd. Drawing (1) 8 @ Figure 1 (A) Red cabbage dye retention time C minutes) Drawing (2) Figure 2 (B) Red cabbage pigment CGT ase treatment solution retained
c'1 (min) Reversed phase liquid reaction amatog 5 feet

Claims (2)

[Claims] (1) Anthocyanins are pigments made by binding and retaining cyclodextrin or other carbohydrates to the hydroxyl groups of the glycoside moieties of anthocyanin pigments. (2) A method for stabilizing pigment anthocyanins, which comprises bonding cyclodextrin or other carbohydrate to the hydroxyl group of the glycoside moiety of an anthocyanin pigment using the enzyme cyclodextrin glycosyltransferase as a catalyst.