KR790001671B1 - Method of extracting 2-hydroxy methyl-3,4,5-trihydroxy piperidins from mulberry - Google Patents

Abstract

Title compbs. (I), useful as typoglycemic agent and additives for pharmaceutics and food, were prepd. by extg. from mulberry root peel with H2O and organic solvent followed by removing acetic ethyl ester-soluble part, and then water-soluble part was sepd. in column chromatography of ion exchanger which compacted with active carbon-celite and silicagel to give I.

Description

How to extract 2-hydroxymethyl-3,4,5-trihydroxypiperidine from mulberry

)을 물 또는 극성 유기용제로 추출하고 이 추출 엑기스에서 다음 구조식(I)으로 표시된 약효물질을 분리하는 방법에 관한 것이다.The present invention is mulberry (

) Is extracted with water or a polar organic solvent and a method for separating the drug substance represented by the following structural formula (I) from this extraction extract.

This substance has a hypoglycemic and other effects and is extremely useful as a pharmaceutical and food additive.

Since ancient times, mulberry has called his root bark in the oriental medicine, and has been used in medicine as a diuretic and antitussive drug, but no other use has been developed.

The present inventors completed the present invention as a result of examining the extraction and purification method of mulberry water or polar organic solvent extraction extract has a hyperglycemic lowering action and other actions.

Features of the present invention include commercially available dry powder of mulberry plants, such as Morus alba L. soybean, M. bombycis Koidz mulberry, M. Lhou Koidz soybean mulberry, and preferably mulberry root bark. For example, the mixture is extracted with a general polar organic solvent such as water or ethanol, concentrated and treated with a smaller polarity such as ethyl acetate, ether or n-hexane, or treated with a non-polar organic solvent to remove the soluble part. It is to separate the active ingredient as a column chromatography. It is also effective to use activated carbon-celite as a filler for column chromatography. Crystals isolated in this way have a molecular weight of 165 in MASS data.

Elemental analysis

Found C 44.13% H 8.41% N 8.67

Calculated C ₆ H ₁₃ NO ₄ C 44.16% H 8.03% N 8.58

Melting point 204-205 ℃

Radiance [α] _D ²² + 45.1 ° (C 0.96 H ₂ O)

The physical properties of and the fact that it is represented by Structural Formula (I) as a result of chemical examination were clarified.

The pharmacological action of this substance (I) was examined. When this drug was orally administered 10 mg / kg to SD rats at the same time with 2 g of glucose per kg body weight, it significantly inhibited the blood sugar rise, therefore, medicine and food additives It is expected to be useful as.

Next, an Example is given and this invention is demonstrated.

Example 1

1 kg of dry commercial white skin is placed in a grinder, and the powder is extracted by cold sedimentation three times for 24 hours with 2 L of methanol. The extracts are combined, concentrated under reduced pressure, and 80 g of methanol extract is obtained. Methanol extract was dissolved in 10 times the amount of water, suspended and the ethyl acetate soluble part was removed, and the aqueous part was collected by column chromatography of 1 kg Amberlite CG-400 (type OH), which was collected by Dowex 50W × 4. (H type) 1 liter column chromatography was developed with water to remove incontaminants such as neutral substances. It is then sufficient to elute with 0.3 N ammonia water, and at that time, the pH of the eluate is shifted from neutral to alkaline, and then 1 liter is collected. When this 0.3 normal ammonia water elution part removed water under reduced pressure and obtained a brown solid, it crystallized with methanol and obtained 570 mg of colorless crystals. The yield is 0.057% with respect to the dry raw material.

Example 2

In Example 1, the methanol extract residue of the lettuce was extracted twice with cold water with 5 L of water for 24 hours.

The extract was concentrated to about 1 L under reduced pressure, and Dow X 1 × 2 1 L column chromatography. Water-extracted portions were further developed on 1 L Dow X 50 W × 4 column chromatography with water to remove impurities such as neutral substances. Then elute with 0.3 N ammonia water.

The 0.3 N ammonia water elution section removed water under reduced pressure to obtain a brown solid, which was dissolved in methanol, treated with a small amount of activated carbon, and crystallized to obtain 50 mg of colorless crystals. The yield was 0.085% with respect to the dry raw material, 1,420mg, 0.142% could be obtained from 1kg of 8 lettuce skin in combination with Example 1.

Example 3

The powder of 500 g of the dried root of M. Lhou Koidz (M. multicaulis Perr) mulberry (S. L.) is chilled twice with 3 L of water for 24 hours. The pouring solution is concentrated to about 1 L under reduced pressure, and developed on water chromatography of 1 kg of activated carbon and celite equivalent mixture with water to remove impurities such as inorganic salts. Subsequently, the mixture is developed with 2 L of ethanol, water, and an equivalent mixture, and the ethanol, water, and eluent are concentrated to dryness under reduced pressure to obtain a brown solid.

Further, this brown solid was extracted with hot methanol, and the methanol soluble part was concentrated after activated carbon treatment to obtain 820 mg of colorless crystals. The yield was 0.164% with respect to the dry raw material.

Example 4

According to Examples 1 and 2, the same drug substance was obtained in the yield of 0.052% in M. alba L acid mulberry bark, and 0.015% in M. bombycis Koidz mulberry leaves.

Claims (1)

Extracts obtained by extracting mulberry plants with water or organic solvent are treated with ion-exchange resins as necessary or treated with activated carbon-celite, silica gel, column chromatography, 2-hydroxymethyl-3. Method for extracting 4,5-trihydroxypiperidine.