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Method for preparing 4-hydroxy-isoleucine from cucurbit seeds

A technology of hydroxyisoleucine and hydroxyisoleucine lactone, which is applied in the field of separating 4-hydroxyisoleucine from fenugreek seeds, can solve the problem of unsuitable industrial production, low total yield, and separation steps cumbersome and other problems, to achieve the effect of simple and feasible separation and purification route

Inactive Publication Date: 2007-05-02
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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Problems solved by technology

These two separation methods are to directly separate 4-hydroxyisoleucine from fenugreek seeds. Because there are many kinds of amino acids in the seeds, direct separation is very troublesome, the price of separation materials is relatively high, the separation steps are cumbersome, and the total yield is relatively high. Low, not suitable for industrial production

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  • Method for preparing 4-hydroxy-isoleucine from cucurbit seeds
  • Method for preparing 4-hydroxy-isoleucine from cucurbit seeds

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Embodiment 1

[0011] Lactonization of 4-hydroxyisoleucine in fenugreek seeds: extract 900g fenugreek seeds with 70% ethanol solution to obtain 18.945g extract, add 1mol / L HCl 50mL, and react under stirring at 100°C . Silica gel TLC (CHCl 3 :CH 3 OH:H 2 (0=10:5:1, volume / volume / volume) detection reaction, find after 10 minutes, 4-hydroxyisoleucine caprolactonization in the fenugreek extract.

[0012] Separation of 4-hydroxyisoleucine lactone:

[0013] Method 1: After cooling the above reaction solution, evaporate it to dryness, and directly use ordinary silica gel column chromatography (30 g of silica gel, particle size is 80-100 mesh) to separate, CHCl 3 :CH 3 OH (10:1, v / v) elution, silica gel TLC (CHCl 3 :CH 3 OH:H 2 (0=10:5:1, volume / volume / volume) detection, the components containing 4-hydroxyisoleucine lactone were combined, acetone (20mL) was added thereto, and white needle-like crystals (total 1.561g) were precipitated. Recrystallized in absolute ethanol (150 mL) to obtain 1...

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Abstract

This invention relates to a preparation of separating 4-hydroxyisoleucine from cucurbit seeds, belonging to research field of phytochemistry. By Lactonizating 4-hydroxyisoleucine that is in cucurbit seeds, (2S,3R,4S)- 4-hydroxyisoleucine internal ester is directly separated by utilizing column chromatography or method of solid liquid extraction, this internal ester is hydrolyzed in the condition of alkalinity to produce (2S, 3R,4S)-4-hydroxyisoleucine. Using this invention separates 4-hydroxyisoleucine from cucurbit seeds, not only obtains (2S,3R,4S)- 4-hydroxyisoleucine that is high purity with high yield, but also the line of separating depuration is convenient and feasible, it possesses production value of industrialization.

Description

technical field [0001] The present invention relates to a new method for isolating 4-hydroxyisoleucine from fenugreek seeds. Background technique [0002] 4-Hydroxyisoleucine is a non-protein amino acid present in fenugreek plants. This amino acid mainly exists in fenugreek seeds, accounting for about 80% of the total content of free amino acids in the seeds. There are eight isomers of 4-hydroxyisoleucine. So far, two diastereoisomers of 4-hydroxyisoleucine have been obtained from fenugreek seeds, and the configuration of the main component is 2S , 3R, 4S, which accounts for about 90% of the total 4-hydroxyisoleucine content in seeds, and the configuration of the minor components is 2R, 3R, 4S, and their NMR spectra are different. Fenugreek (Trigonella foenum-graecum) is an annual herbaceous plant belonging to the genus Fenugreek in the family Fabaceae, widely distributed in Asia, Europe and Africa. Fenugreek seeds are traditional Chinese medicina...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/38
Inventor 刘玲丁永良李伯刚张国林
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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