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Method for preparing immune adjuvant soybean saponin lipotropy derivatives with enhanced activity

An immunoadjuvant and activity-enhancing technology, applied in the field of medicine and biology, can solve the problems of strong hemolysis, large toxic and side effects, poor stability, etc., and achieve the effects of high derivative purity, convenient operation and simple process.

Inactive Publication Date: 2014-09-10
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they are highly toxic and side effects, strong hemolytic and poor stability

Method used

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  • Method for preparing immune adjuvant soybean saponin lipotropy derivatives with enhanced activity
  • Method for preparing immune adjuvant soybean saponin lipotropy derivatives with enhanced activity
  • Method for preparing immune adjuvant soybean saponin lipotropy derivatives with enhanced activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The method for preparing the activity-enhanced immune adjuvant soybean saponin lipophilic derivative comprises the following steps:

[0041] (1) Mixed reaction: Accurately weigh 80 mg of soybean saponin Ab, dissolve it in 5 mL of pyridine, add 68.9 mg of dicyclohexylcarbodiimide (DCC), 38.5 mg of N-hydroxysuccinimide (NHS), and 82.6 mg of Dialkylamine, magnetically stirred at 800r / min, reacted at room temperature for 3 days;

[0042] (2) Add water to terminate the reaction: add 5 mL of ultrapure water to the reaction mixture, and magnetically stir at 800 r / min at room temperature overnight;

[0043] (3) Static layering: After overnight, add 10 mL of ethyl acetate, shake the shaker intermittently for 10 min, transfer to a separatory funnel to stand overnight, and obtain a water layer and an ethyl acetate layer.

[0044] Ethyl acetate layer is detected as the reactant with retention time of 95min by HPLC, ESI-MS and 1 H and13 The C spectrum was analyzed as soybean sapon...

Embodiment 2

[0067] The method for preparing the activity-enhanced immune adjuvant soybean saponin lipophilic derivative adopts the following steps:

[0068] (1) Utilize high-purity (purity greater than 99%) soybean saponin Ab, carbodiimide reagent and dodecylamine to prepare the target product, specifically adopt the following steps:

[0069] a. Mixed reaction: dissolve high-purity soybean saponin Ab in pyridine, add dicyclohexylcarbodiimide, N-hydroxysuccinimide and dodecylamine successively, wherein soybean saponin, dicyclohexylcarbodiimide, N - the mass ratio of hydroxysuccinimide and dodecylamine is 80:65:35:80, the magnetic stirring speed is 800r / min, and the reaction is carried out at room temperature for 3 days;

[0070] b. Add water to terminate the reaction: add ultrapure water to the reaction mixture, the volume ratio of ultrapure water to pyridine is 1:1, control the magnetic stirring speed to 800r / min, and leave overnight at room temperature;

[0071] c. Static layering: add ...

Embodiment 3

[0080] The method for preparing the activity-enhanced immune adjuvant soybean saponin lipophilic derivative adopts the following steps:

[0081] (1) Utilize high-purity (purity greater than 99%) soybean saponin Ab, carbodiimide reagent and dodecylamine to prepare the target product, specifically adopt the following steps:

[0082] a. Mixed reaction: dissolve high-purity soybean saponin Ab in pyridine, add dicyclohexylcarbodiimide, N-hydroxysuccinimide and dodecylamine successively, wherein soybean saponin, dicyclohexylcarbodiimide, N -The mass ratio of hydroxysuccinimide and dodecylamine is 80:70:40:85, the magnetic stirring speed is 800r / min, and the reaction is carried out at room temperature for 3 days;

[0083] b. Add water to terminate the reaction: add ultrapure water to the reaction mixture, the volume ratio of ultrapure water to pyridine is 1:1, control the magnetic stirring speed to 800r / min, and leave overnight at room temperature;

[0084] c. Static layering: add e...

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Abstract

The invention relates to a method for preparing immune adjuvant soybean saponin lipotropy derivatives with enhanced activity. The method comprises the following steps: preparing a target product from high-purity soyasaponin Ab, a carbon imine reagent and lauryl amine; detecting the target product by adopting analytical type high performance liquid chromatography (HPLC) and personal digital assistant (PDA) detectors and an evaporative light scattering detector (ELSD); identifying the molecular weight of the target product by using electrospray ionization-mass spectrometry (ESI-MS); carrying out purification and separation by adopting preparative liquid chromatography, so as to obtain lipotropy derivatives AbD of lauryl amine; and analyzing the structure of the target product by adopting nuclear magnetic resonance (NMR). Compared with the prior art, a high-purity modifier AbD is prepared by adopting the method, the molecular weight of the target product is 1603, the yield is 6.94%, the hemolysis ratio is low, the immune adjuvant soybean saponin lipotropy derivatives have potentiation on in vitro immunization of spleen lymphocytes in mice, and meanwhile, the level of four specific antibodies in OVA immune serum in mice is improved.

Description

technical field [0001] The invention belongs to medical biotechnology, and in particular relates to a method for preparing activity-enhanced immune adjuvant soybean saponin lipophilic derivatives. Background technique [0002] Soybean saponins belong to the pentacyclic triterpenoid oleanane type saponins, which are composed of two parts: daidzein (Soyasapogenol) and oligosaccharides. It mainly exists in soybean seeds, accounting for about 0.6%-6.2% of the latter, and is formed by dehydration condensation of hydroxyl groups of triterpenoid homologues and cyclic hemiacetal hydroxyl groups of sugar molecules. Soybean saponin aglycone is divided into: aglycone (Soyasapogenol) A, aglycone B and aglycon E; the monosaccharides on the sugar chain mainly include β-D-glucose, β-D-galactose, β-D-xylose, 6 kinds of α-L-rhamnose, α-L-arabinose, β-D-glucuronic acid, etc. In recent years, scholars at home and abroad have proved that soybean saponins have a variety of beneficial physiolog...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07H15/256C07H1/00A61P37/04
Inventor 赵大云任小云冯凡
Owner SHANGHAI JIAO TONG UNIV
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