JPH0840912A - Saccharide absorption inhibitor - Google Patents

Abstract

PURPOSE:To obtain an oleanolic acid 3-o-beta-D-glucopyranosidouronic acid as the subject inhibitor by purifying with a silica gel a crude beet saponin derived from the extraction residues of sugar beet having been mass-wasted from sugar manufacturing works. CONSTITUTION:A crude beet saponin is subjected to silica gel column chromatography and purified to obtain oleanolic acid 3-o-beta-D- glucopyranosidouronic acid of the formula in high yield. This compound, a beet saponin, has excellent glucose/sucrose absorption-inhibitory activity, thus being useful as a raw material for medicines or functional foods; therefore, also usable for obesity prevention or hyperglycemia suppression.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing oleanolic acid 3-O-β-D-glucopyranoside uronic acid (hereinafter abbreviated as OGA) by purifying crude peat saponin, and glucose and beet saponin as active ingredients. The present invention relates to a sucrose absorption inhibitor.

[0002]

BACKGROUND OF THE INVENTION Sugar beet is a plant of the family Rhinoceros family, commonly called beet, which is cultivated in large quantities to produce sugar from this rape root.
Contains% beet saponin.

Since there has been no report on the effective use of beet saponin, the present inventors have previously conducted research on this and beet from beet pulp extracted from beet pulp (beet pulp) and the like, which are abundantly discharged in sugar mills. Saponin was easily extracted in good yield, and the crude beet saponin was subjected to a pharmacological test. As a result, the efficacy against hyperlipidemia and ulcer was found (Japanese Patent Publication No. 5-7399).

[0004]

In order to utilize beet saponin more effectively, the sugar absorption inhibitory action of beet saponin is studied. Therefore, pure beet saponin (OG
Research on the manufacturing method of A) will also be conducted.

[0005]

Since there is no report on the industrial production method of OGA, as a result of various studies, the present inventors have found that crude beet saponin was purified by subjecting it to silica gel column chromatography to obtain a good yield. It has been found that OGA can be manufactured at.

[0006] Further, since the sugar absorption inhibitory action of beet saponin has not been reported at all, the sugar absorption inhibitory action of OGA and crude beet saponin was examined, and it was found that it has an excellent effect on glucose and sucrose. I found it. Therefore, beet saponin can also be used for preventing obesity or suppressing hyperglycemia.

Acarbose, which is widely used as a hyperglycemic inhibitor, is effective for sucrose and not glucose, but the compound of the present invention is characterized by being effective for both glucose and sucrose.

Beet saponin can be orally administered in the form of powder, granules or tablets by itself or in admixture with a suitable pharmacologically acceptable additive.

For example, excipients such as starch, D-sorbitol and crystalline cellulose, binders such as polyvinylpyrrolidone, methyl cellulose, hydroxypropyl cellulose, gum arabic and gelatin, disintegrating agents such as carboxymethyl cellulose calcium, talc and magnesium stearate. A lubricant, a flavoring agent such as polyethylene glycol, and the like can be used to prepare powders, granules, tablets, or the like.

The dose of OGA varies depending on the patient's symptoms, age, weight, etc.
Oral administration of 100 mg 3 times a day immediately before each meal.

The present invention will be further described below in the form of test examples and examples of the present invention. Test Example 1. Inhibition of blood glucose elevation in glucose-loaded rats Male test rats of Wistar strain (body weight 125-155 g) fasted for 20-24 hours were orally administered with the test substance, and 30 minutes after that, glucose (0.5 g / kg) was orally administered. . About 0.4 ml of blood was collected from the jugular vein with time under non-anesthetic restraint (only when collecting blood), and the blood glucose level was measured.

The results are shown in Table 1.

[Table 1]

According to Table 1, OGA is 25 mg and 50 m
g, 100 mg / kg administration group, and beet saponin (purity 22%) in the 200 mg / kg administration group, a significant inhibitory effect on blood glucose level increase was observed at 0.5 to 2.0 hours compared with the control group. However, it is not found in acarbose.

Test Example 2. Inhibition of blood sugar level increase in sucrose-loaded rats Male test rats of Wistar strain (body weight 130 to 165 g) fasted for 20 to 24 hours were orally administered with the test substance, and 30 minutes after that, sucrose (1 g / kg) was orally administered. . About 0.4 ml of blood was collected from the jugular vein with time under non-anesthesia restraint (only when collecting blood), and the blood glucose level was measured.

The results are shown in Table 2.

[Table 2]

According to Table 2, OGA is 100 mg / kg
In the administration group of 1, the significant increase in blood glucose level is observed at 0.5 to 2.0 hours as compared with the control group.

Example 1 To 10 kg of dried beet pulp, 60 l of 0.18% sodium hydroxide solution was added, and after heating at 40 ° C. for an hour, this extract was treated with a 20,000 fraction UF membrane, and 35% hydrochloric acid was added to the permeate. In addition, the mixture was made acidic and the precipitate was centrifuged and dried and pulverized to obtain 171 g of crude beet saponin (purity 22%). 100 g of the crude beet saponin was applied to silica gel column chromatography (silica gel G60-230 mesh 3 kg manufactured by Merck & Co., eluent chloroform-methanol-water mixed solvent) to obtain 20 g of OGA. This was recrystallized from methanol to obtain colorless needle crystals having a melting point of 264 to 267 ° C (decomposition).

[Α] _D ⁹ + 20.4 ° (C = 0.8
0, methanol)

1R (KBr, cm ^-1 ): 3400, ¹
720, 1100-1000

[0020] The a ¹³ C-NMR spectrum in Table 3 ¹
The 1 H-NMR spectrum is shown in Table 4.

[Table 3]

[0021]

[Table 4]

Example 2. Powders The following ingredients are used, and the 12th revised Japanese Pharmacopoeia General Regulations No. 1
A powder was prepared according to item 3. Take 1 packet once per adult 3 times daily before meals.

Example 3. Granules The following ingredients are included in the 12th revised Japanese Pharmacopoeia General Regulations No. 7
The granules were manufactured according to the section. Take 1 packet once per adult 3 times daily before meals.

Example 4. Tablets Take the following ingredients, and twelfth revised Japanese Pharmacopoeia General Regulations No. 1
Tablets were produced according to paragraph 5. Take 2 tablets once daily for adults 3 times daily before meals.

[0025]

INDUSTRIAL APPLICABILITY According to the present invention, beet saponin has an excellent glucose and sucrose absorption inhibitory action, and is therefore used as a raw material for pharmaceuticals or functional foods.

Claims (2)

[Claims] 1. The following formula (1), characterized in that crude beet saponin is purified on silica gel. A method for producing oleanolic acid 3-O-β-D-glucopyranoside uronic acid represented by 2. A glucose and sucrose absorption inhibitor containing beet saponin as an active ingredient.