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A kind of Mogrosin A derivative and its preparation method and application

A technology of AHA and derivatives, which is applied in the preservation, application, and food science of food ingredients as antimicrobials, and can solve problems such as unknown active ingredients.

Active Publication Date: 2022-06-21
HUNAN HUACHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] It has been reported in the prior art that the extract of Luo Han Guo has a certain antibacterial effect, but its active ingredients are still unknown

Method used

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  • A kind of Mogrosin A derivative and its preparation method and application
  • A kind of Mogrosin A derivative and its preparation method and application
  • A kind of Mogrosin A derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (S1) get 4.72g (0.01mol) of mogrosin acid methyl, 4g ethyl acetate and petroleum ether mixed solvent (v / v=1:1), 0.05g anhydrous DMF is put into reaction vessel, drip slowly under 50 ℃ of stirring conditions 3.57g of thionyl chloride (0.03mol) was added, and the dropwise addition was completed within 1h, and the reaction was kept at 50°C for 5h. During the reaction, the tail gas was absorbed by 10% NaOH aqueous solution, and the excess thionyl chloride and solvent were evaporated after the reaction;

[0037] (S2) slowly add the mixed solution of 1.61g sodium hydroxymethanesulfonate (0.012mol) and 5g anhydrous DMF to (S1) reaction vessel, complete dropwise addition within 1h, control system temperature to react at 40 ℃ for 12h, the reaction After the end, adjust the pH to 9-9.5 with saturated NaHCO3, stand for stratification, take the organic layer, add 3 g of anhydrous sodium sulfate, stand for 3 hours to remove the water in the solvent, filter, evaporate the solvent, use...

Embodiment 2

[0040] Other operations and conditions are the same as in Example 1, except that in step (S2) 1.61 g of sodium isethionate is replaced with 1.78 g of sodium isethionate (0.012 mol). Finally, 5.23 g of white crystals were obtained, the HPLC purity was 99.0%, and the yield was 86.0%. It is a compound in which n=2 in the structure of formula (I), which is compound 2.

[0041] 1 HNMR (CDCl 3 ): 0.76 (3H, s, C28), 0.93 (3H, d, C21), 1.18 (3H, d, C29), 1.22 (3H, s, C18), 1.38 (1H, m, C20), 1.45 (1H , d, C8), 1.56 (2H, m, C2), 1.61 (1H, t, C17), 1.85 (3H, s, C26), 2.13 (1H, d, C10), 2.52 (1H, d, C12- H a ), 2.62 (1H, d, C4), 2.70 (1H, d, C12-H b ), 3.24 (2H, t), 3.55 (1H, d, C19-H a ), 3.81 (1H, t, C3), 4.18 (2H, t), 4.65 (1H, d, C19-H b ), 6.87 (1H, t, C24). ESI: MS(M-Na): 551.3.

Embodiment 3

[0043] Other operations and conditions are the same as in Example 1, except that in step (S2) 1.61 g of sodium hydroxymethanesulfonate is replaced by 2.11 g of sodium 4-hydroxybutanesulfonate (0.012 mol). Finally, 5.49 g of white crystals were obtained, the HPLC purity was 99.1%, and the yield was 86.3%. It is the compound of formula (I) where n=4, which is compound 3.

[0044] 1 HNMR (CDCl 3 ): 0.76 (3H, s, C28), 0.93 (3H, d, C21), 1.18 (3H, d, C29), 1.22 (3H, s, C18), 1.38 (1H, m, C20), 1.45 (1H , d, C8), 1.61 (1H, t, C17), 1.85 (3H, s, C26), 2.13 (1H, d, C10), 2.52 (1H, d, C12-H a ), 2.62 (1H, d, C4), 2.70 (1H, d, C12-H b ), 3.26 (2H, t), 3.55 (1H, d, C19-H a ), 3.81 (1H, t, C3), 4.02 (2H, t), 4.65 (1H, d, C19-H b ), 6.87 (1H, t, C24). -O-CH on huangbutyl 2 -CH 2 -CH 2 -CH 2 -SO 3 The H on the two methylene groups in the middle of Na is mixed with the H on the other methylene groups in the mogro acid A, and cannot be distinguished. ESI: MS(M-Na): 579.3.

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Abstract

A kind of Mogrosin A derivative and its preparation method and application of the present invention, described Mogrosin A derivative structural formula is as shown in formula (I): wherein-(CH 2 ) n‑SO 3 M, n is an integer of 1-4, and M is K or Na. The present invention utilizes hydroxyalkyl sulfonate and mogrosinic acid methyl esterification reaction to obtain the compound of formula (I), not only the solubility of mogrosinic acid derivatives is significantly improved, but also has improved antibacterial activity, which can be compared at pH5-9 It can maintain good antibacterial activity in a wide range, and the safety test has passed the food additive standard, so it can be used as a preservative in food. The invention broadens the application field for the application of Luo Han Guo, and also provides a research and development idea of ​​a new natural preservative.

Description

technical field [0001] The invention relates to a mogrosic acid derivative, in particular to a mogrosolic acid derivative and a preparation method and application thereof. Background technique [0002] Food spoilage refers to the process in which food has undergone a series of changes in its original chemical, physical or sensory properties due to the influence of various internal and external factors, reducing or losing its original nutritional value or commodity value; or It refers to the various changes in food composition and sensory properties caused by the action of microorganisms under the influence of certain environmental factors. The process of food spoilage is essentially certain biochemical processes in which proteins, carbohydrates, and fats in food are metabolized and decomposed by microorganisms or their own tissue enzymes. For example, the after-cooking of fresh meat and fish, the respiration of grains and fruits, etc. can cause the decomposition of food com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A23L3/3544
CPCC07J71/0005A23L3/3544A23V2002/00A23V2200/10
Inventor 李伟黄华学贺进军黄俊宋谷良江小龙
Owner HUNAN HUACHENG BIOTECH