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Acylated derivative of mogrolic acid and preparation method thereof

A kind of derivative, Luohan technology, applied in the field of acylation of Luohanguo acid and its preparation field, can solve the problems of short half-life, limited application, poor water solubility of Luohanguo acid, etc.

Active Publication Date: 2021-09-24
HUNAN HUACHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The water solubility of mogrosan fruit acid is extremely poor, which limits its dosage form, usage method and human body absorption; and if it is used directly as a drug, its half-life is short, which affects the curative effect and increases the dosage
Coupled with the scarcity of mogrosin in natural plants, the difficulty of separation and purification, and the application research is still in its infancy, its application in the fields of food, health care products, cosmetics, and pharmaceuticals has been limited.

Method used

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  • Acylated derivative of mogrolic acid and preparation method thereof
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  • Acylated derivative of mogrolic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Acylation reaction: Take 4.72g (0.01mol) of mogrosinic acid A, 2.47g (0.012mol) of DCC, and 1.5g of triethylamine dissolved in 35mL of ethyl acetate, stir for 30min under ice bath, then slowly add 15mL of the solution dropwise. There are 1.33g (0.013mol) of acetic anhydride and 0.12g of DMAP in ethyl acetate solution, the dropwise addition is completed within 1 hour, and the reaction is stirred at room temperature for 8 hours, and the reaction is complete by HPLC detection.

[0035] (2) Post-treatment: After the reaction is complete, the reaction solution is washed with water to neutrality, added with 2.5 g of anhydrous sodium sulfate for dehydration, concentrated under reduced pressure, and dried in vacuo to obtain a white solid. v / v) was the developing solvent, and finally obtained 4.49g of the product as white crystal 3-O-acetylmogrosvenous acid A, with a purity of 98.31% and a yield of 85.78% by HPLC.

[0036]

Embodiment 2

[0038] (1) Acylation reaction: Take 4.56g (0.01mol) of mogrosinic acid butyl, 2.47g (0.012mol) of DCC, 4.2g of pyridine dissolved in 50mL of ethyl acetate, stir for 30min under ice bath, then slowly add dropwise 15mL of 1.33 g (0.013mol) of acetic anhydride and 0.12g of DMAP in ethyl acetate were added dropwise within 1 hour, stirred and reacted at room temperature for 8 hours, and the reaction was complete by HPLC detection.

[0039] (2) Post-treatment: after the reaction is complete, the reaction solution is washed with water to neutrality, added with 3g of anhydrous magnesium sulfate for dehydration, concentrated under reduced pressure, and dried in vacuo to obtain a white solid. / v) was the developing solvent, and finally obtained 4.49g of the product as white crystal 20-O-acetyl mogrosinic acid A, with a purity of 97.54% and a yield of 85.78% by HPLC.

[0040]

Embodiment 3

[0042]Other conditions and operations were the same as in Example 1, except that 1.33 g (0.013 mol) of acetic anhydride was replaced by 1.69 g (0.013 mo) of propionic anhydride. Finally, 4.60 g of white crystal 3-O-propionyl mogrosinic acid A was obtained, with a purity of 98.17% and a yield of 85.45% by HPLC.

[0043]

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Abstract

The invention relates to an acylated derivative of mogrolic acid. The structure of the acylated derivative is shown as a formula (I) or a formula (II), wherein R is acyl. Hydroxyl groups in molecules of several kinds of mogrolic acid (mogrolic acid A and mogrolic acid D) containing hydroxyl groups are acylated, and on the premise that the pharmacological activity of the hydroxyl groups is not changed, the molecular structure is modified, so that the solubility is improved. Besides the solubility is improved, the molecular stability of the hydroxyl acylated mogrolic acid is improved, the residence time of the hydroxyl acylated mogrolic acid in a living body can be effectively prolonged, and the bioavailability is improved. The inventor also finds that the acylated derivative of mogrolic acid provided by the invention has excellent anti-inflammatory activity, especially a maleic acid acylated derivative of mogrolic acid.

Description

technical field [0001] The invention relates to a mogrosan fruit acid derivative and a preparation method thereof, in particular to an acylated mogrosan fruit acid derivative and a preparation method thereof. Background technique [0002] Luo Han Guo is a rare local specialty in Guilin, mainly produced in Yongfu County and Longsheng County, and it is also one of the first batch of "dual-use medicine and food" materials approved by the state. Mogroside is a unique natural high-power sweetener in Luo Han Guo. Its sweetness is 300 times that of sucrose, and its calories are zero. preventive effect. As a food, mogroside is safe and non-toxic. According to the national mandatory standard "GB2760 Food Additive Use Standard", mogroside can be used in various foods without limit. [0003] The planting, production and processing of Luo Han Guo fresh fruit and the terminal application of mogroside in my country have reached a considerable scale and are developing rapidly. However, ...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J9/00A61P29/00
CPCC07J71/0005C07J9/005A61P29/00
Inventor 李伟黄华学贺进军黄俊宋谷良江小龙
Owner HUNAN HUACHENG BIOTECH
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