JPS59137499A - Inclusion compound of rutin and cyclodextrin - Google Patents

Abstract

PURPOSE:The titled inclusion compound useful as a recruiting agent for food, or an atioxidant, having extremely improved solubility of rutin in water and stability to light, obtained by including rutin in cyclodextrin(-containing decomposition product of starch). CONSTITUTION:1mol rutin is blended with preferably 2-10mol cyclodextrin (preferably beta- or gamma-cyclodextrin) or cyclodextrin-containing decomposition product of starch, the blend is mixed with 1- twice as much as water by weight, kneaded, and dried, to give the desired inclusion compound.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an inclusion compound of rutin and cyclodextrin or a starch decomposition product containing cyclodextrin.

Rutin (L3'@4'#5.7- Pentahy
droxyflavone -3-[6-O-(6-d
eox)'-α-1-mannopyranosyl
)-8-D-glucopyranoside]
trihydrate) is a pale yellow, needle-shaped crystal that was discovered in Rutaceae (Rutaceae), and was later isolated from plants such as buckwheat (Polygonaceae), apricot cloves (Fabaceae), tobacco leaves, tomatoes, etc. It consists of a structural formula.

Rutin has the effect of strengthening capillaries and is said to be effective in preventing cerebral hemorrhage, radiation damage, and various hemorrhagic diseases. Buckwheat, which contains rutin, has been eaten regularly since ancient times as a food that prevents these diseases. It is well known. Furthermore, this product is also used as an antioxidant MIJ because it has an antioxidant effect on foods.

Generally, rutin is extracted from the plant body into hot water, alcohol, etc.
: 9 pieces, crystallized and commercially available as anhydrous rutin.

Rutin is an extremely useful compound as described in +]tJ, so it can be effectively used as a reinforcement for JlJ products.
However, there was a serious bottleneck in this approach.

In other words, rutin is water-soluble and can be engraved with light, etc.
Because it has the drawback of poor stability and gradually turning gray if left untreated, it has been difficult to use as a reinforcing agent for foods.

1+J, a food reinforcement agent that eliminates the defects kj'Jl has in rutin! It would be truly beneficial if it could be widely used as an anti-oxidizing agent, and the industry is also demanding improvements in this respect.

Fuzure Kansai has conducted various tests to solve the above problems.
・The present invention was completed based on the discovery that the water solubility of rutin is significantly improved and its stability against light etc. is also improved when the binding material, rutin, is encapsulated and sealed with cyclodextrin.

Hereinafter, the non-invention will be explained in detail.

The non-invention is rutin and cyclodextrin or cyclodextrin-containing 6' which significantly improves the water solubility of rutin by clathrating rutin with cyclodextrin.
Concerning clathrate compounds with powder decomposition products.

Here, cyclodextrin is a crown-shaped non-reducing dextrin in which 6 to 12 glucose molecules are cyclically bonded through α-1,4-glucoside bonds.
α-cyclodextrin, consisting of 6 molecules of glucose, 7
β-cyclodextrin consisting of 8 molecules, r-cyclodextrin consisting of 8 molecules, or a mixture thereof are said to be useful. These cyclodextrins have a crown-like shape and therefore have a cavity inside the molecule. The inside of this cyclodextrin cavity has a hydrophobic atmosphere, and the outside of the molecule is hydrophilic, so there is a hydrophobic inlet in the molecule cavity. , these functional groups fully incorporate the ability to form F\ compounds.

:4: 'ii, + cyclodextrin used here 1); 1, starch content containing all cyclodextrin 1' + '51r + f-r, known method, specifically 11' F No. 886583 Schiff, 71. ! l'WF
, S914137, QS Publication Ud53-31223, etc., and can be easily prepared using methods described in the following publications. In other words, the two-grain flour fraction containing cyclodextrin is, for example, a cyclodextrin-containing flour.
:j: :1y or using nu-α-amylase, which bacteria of the genus Bacillus resides].
Cyclodextrin-producing enzyme (Cyclodextring glycosyl) produced by bacteria such as Bacillus macerans, Bacillus zaki: and Llans.
transferase).

Further, cyclodextrin can be obtained by separating the starch decomposition product containing the above-mentioned cyclodextrin by a known method to obtain α-0β-2γ-cyclodextrin.

Furthermore, in the present invention, the starch decomposition product containing all of the above cyclodextrin is added with glucoamylase, β-amylase, pullulanase, or ultraviolet α-amylase, which does not decompose cyclodextrin (7J) or fractionated pixel. β-cyclodextrin is separated as a crystal from starch saccharified products containing and having this 7-cyclodextrin. The remaining crystal P solution can also be used.

In the present invention, it is possible to use either the starch decomposition product containing 7 clodextrin, as well as the β-2γ-cyclodextrin separated from this cyclodextrin-containing starch decomposition product, or α- As for cyclodextrin, since the effect of improving the water solubility of rutin is not observed, it is preferable to use I- to γ-cyclodextrin.

Rutin and 7 when rutin is clathrated with 7 clodextrino
The usage ratio of clodextrin is 1 mole of rutin, 1 to 20 moles of cyclodextrin, preferably 2 to 20 moles of cyclodextrin.
As a method for wrapping rutin with 7 clodextrino in a range of 10 moles, any of the following methods may be employed.

(1) Mixing method: Add about 1 to 2 times the amount of water to clodextrin and rutin (1 x 1 constant + 6), knead, dry, and prepare the clathrate compound.

(2) Heating about 5-10% of soluble cyclodextrin at once fG i
Add a predetermined amount of rutin to this, mix and stir the barley, cool, and leave as is or dry to obtain a clathrate compound.

(:3) Mixed pulverization method Add a predetermined amount of cyclodextrin and rutin in powder form, and pulverize with a high-speed pulverizer to obtain a clathrate compound.

Next, the following experiment was conducted to confirm the water solubility effect of rutin according to the present invention.

Example In order to compare solubility, each sample shown in Table 1 was added to water until it became supersaturated, and after shaking at room temperature for 40 hours,
This was centrifuged at 9,000 r, p, +n for 10 minutes, diluted appropriately, and quantified by absorbance measurement at 352 nm. The results are shown in Table 1.

In addition, in the table, the solubility in water (■/ml) is a value calculated in terms of rutin.

Note) Samples A to E were those prepared in Example 1.

Sample F uses Rutin 100rk as is.
, D, and E have improved solubility compared to the control F, especially γ-
When using 7 clodextrin, a questionable effect was observed. Moreover, no effect was observed in sample C using α-zoclodex).

As described above, the uninvented clathrate compound of rutin and noclodextrin has significantly improved the solubility of rutin, which is thermophilic to water. I can drink it again (6'i
7] 1] It does not cause cloudiness or precipitation even when used, so it can be effectively used as a nutritional supplement for all foods and drinks.

Below 1. + Shows examples of the invention.

Example Five types of clathrate compounds A to E were prepared by the following method.

Prisoner Rutin 1002 and β-Cyclodextrino 2067
9 (anhydrous equivalent 1860f) was added with 3513' of water, mixed at room temperature for 2 hours, and freeze-dried to obtain a rutin:β-cyclodextrin clathrate with a molar ratio of 1:10.

(B) Rutin 1002 and β-cyclo rkistrin 3
100 f (anhydrous exchange 34: 2790 f) to 526 f
゜- was added, mixed at room temperature for 2 hours, and dried with hot air to obtain a rutin:β-7 clodextrin clathrate with a molar ratio of 1:15.

(0 Rutin 1001 α-cyclodextrin 893y
(795 r on anhydrous basis) was added with 780 g of water, mixed at room temperature for 2 hours, and freeze-dried to obtain a rutin:α-7 clodextrin clathrate with a molar ratio of 1-:5.

0 Rutin l0IF and γ-7 clodextrin 119f
(Anhydrous conversion 106r) and 3'OO+++/! was added, mixed at room temperature for 10 hours, and freeze-dried to obtain rutin:γ-7.
A clathrate compound with a clodextrin molar ratio of 1:5 was obtained.

(E) Rutin 10 (1? (!: α-1β-1γ
-Tani cyclodextrin-containing starch-degrading starch syrup (cyclodextrin content solid lunch box, !1l 120%, α:β:γ
=1:5:4. Water 25 g) 6460 f and 1800 g of water were mixed together at room temperature for 20 hours, freeze-dried,
A rutin:α-1β-1γ-mixed cyclodextrin clathrate compound with a molar ratio of 1:5 was obtained.

patent applicant Nichifu Food Chemical Co., Ltd. Nakajima Chemical Industry Co., Ltd. agent Former Patent Attorney Ishibe (1 other person)

Claims (4)

[Claims] (1) A clathrate compound of rutin and a starch decomposition product containing 7 clodextrino or cyclodextrin. (2) The clathrate compound according to claim 1, wherein the 7-cyclodextrin is β- or γ-cyclodextrin. (3) The cyclodextrin-containing 11ha decomposition product is
The clathrate compound according to item 1 of the scope of the patent n blue water, which has a cyclodextrin content of 10% or more obtained by reacting a cyclodextrin-forming enzyme with a liquefied liquid of starch oxide or σ functional material. (4) The ratio of rutin and cyclodextrin used is 1 mole of rutin to 1 mole of cyclodextrin.
The clathrate compound according to claim 1, which is 0 mol.