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Mogrol derivative monomer as well as preparation method and application thereof

A technology of mogrosideol and derivatives, applied in the directions of drug combination, pharmaceutical formula, steroid compound, etc., can solve the problems of lack of carboxyl compound synthesis method and anti-inflammatory effect, etc.

Inactive Publication Date: 2021-04-20
GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, looking at the structural transformation of the few mogrosanol, there is no research on the synthesis method and anti-inflammatory effect of carboxyl compounds.

Method used

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  • Mogrol derivative monomer as well as preparation method and application thereof
  • Mogrol derivative monomer as well as preparation method and application thereof
  • Mogrol derivative monomer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The preparation method of the mogroside alcohol derivative monomer of the present embodiment comprises the following steps:

[0064] Step 1: Preparation of intermediate product M-1

[0065] Take 1.5 g of mogrosinol, dissolve it in 15 mL of acetone, add 15 mL of pure water, raise the temperature to 40°C and stir for 5 minutes to obtain mogrosinol solution.

[0066] Take 15mL of acetone, 15mL of pure water and 0.3mL of acetic acid, and mix them uniformly to obtain the mixed solution A.

[0067] Take 1.5g of sodium periodate, dissolve it in the above-mentioned mixed solution A, and mix evenly to obtain the mixed solution B.

[0068] Slowly add the above-mentioned mixture B to the above-mentioned mogrosin alcohol solution, and react in the dark at 40°C for 16 hours after the dropwise addition, and then lower it to room temperature at 20°C, remove the acetone under reduced pressure, and extract twice with ethyl acetate. is 20mL, and the second dosage is 10mL. After the org...

Embodiment 2

[0085] The preparation method of the mogroside alcohol derivative monomer of the present embodiment comprises the following steps:

[0086] Step 1: Preparation of intermediate product M-1

[0087] Take 2.5g of mogrosinol, dissolve it in 30mL of acetone, add 30mL of pure water, raise the temperature to 60°C and stir for 10min to obtain mogrosinol solution;

[0088] Take 20mL of acetone, 20mL of pure water and 0.6mL of acetic acid, and mix them uniformly to obtain the mixed solution A.

[0089] Take 2.5g of sodium periodate, dissolve it in the above-mentioned mixed solution A, and mix evenly to obtain the mixed solution B.

[0090] Slowly add the above-mentioned mixture B to the above-mentioned monk fruit alcohol solution, and react at 60°C in the dark for 24 hours after the dropwise addition, and then lower it to room temperature of 25°C, remove the acetone under reduced pressure, and extract twice with dichloromethane, the first dosage is 25mL, and the second dosage is 10mL....

Embodiment 3

[0100] The preparation method of the mogroside alcohol derivative monomer of the present embodiment comprises the following steps:

[0101] Step 1: Preparation of intermediate product M-1

[0102] Take 3.0 g of mogrosinol, dissolve it in 50 mL of acetone, add 50 mL of pure water, raise the temperature to 60°C and stir for 15 minutes to obtain mogrosinol solution.

[0103] Take 30mL of acetone, 30mL of pure water and 1.0mL of acetic acid, and mix them uniformly to obtain the mixed solution A.

[0104] Take 3.0 g of sodium periodate, dissolve it in the above-mentioned mixed solution A, and mix it uniformly to obtain the mixed solution B.

[0105] Slowly add the above-mentioned mixture B to the above-mentioned monk fruit alcohol solution, and react at 60°C in the dark for 30 hours after the dropwise addition, and then lower it to room temperature of 30°C, remove the acetone under reduced pressure, and extract twice with chloroform, the amount used for the first time is 20mL, an...

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Abstract

The invention discloses a mogrol derivative monomer as well as a preparation method and application thereof, and belongs to the technical field of structural modification of plant active ingredients. The mogrol derivative monomer is a compound shown as a formula 2, and the invention also discloses a preparation method and application of the mogrol derivative monomer. According to the mogrol derivative monomer disclosed by the invention, the C-24 site of mogrol is selectively derived into a single carboxyl group on the premise of keeping chirality of each site on a tetracyclic parent nucleus of mogrol and not changing a functional group, and the high reaction activity of the carboxyl group is convenient for further derivatization.

Description

technical field [0001] The invention relates to a mogroside alcohol derivative monomer, a preparation method and application thereof, and belongs to the technical field of structural transformation of plant active ingredients. Background technique [0002] Luo Han Guo, scientific name Siraitia grosvenorii (Swingle.) C. Jeffrey, is the dried fruit of the perennial liana of Cucurbitaceae, which has the effects of moistening the lungs and laxative, relieving cough and reducing phlegm. Mogrol, the English name mogrol, is the parent nucleoside element of mogrosides ⅠA1, ⅠE1, ⅡE, Ⅲ, Ⅳ, ⅣVE, Ⅴ and simonoside I, etc., and belongs to the cucurbitane-type tetracyclic triterpenes. Hydroxyl, high oxidation, steric effects and other factors make it difficult to carry out chemical modification. [0003] Mogrosvenol is a product that enters the blood after metabolism in the body of Luo Han Guo. In the existing research, the C-24 and 25-position o-hydroxyl structure of mogrosanol can be o...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61P29/00A61K31/575
Inventor 宋静茹李典鹏
Owner GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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