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Novel blank liposomes taking ginsenoside derivatives as membrane materials, and preparation method and application thereof

A blank liposome, ginsenoside technology, applied in liposome delivery, skin care preparations, chemical instruments and methods, etc. higher sexual issues

Active Publication Date: 2019-06-04
XIAMEN GINPOSOME PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The technical problem to be solved by the present invention is to overcome the lipophilic ends such as Rg3 and Rh2 in the prior art and only have a double bond or saponins without double bonds as liposomes The liposome outward appearance that obtains during membrane material, encapsulation efficiency, particle size and stability are all poor, or part ginsenoside hemolytic property is high, can not be used as the defect of liposome membrane material, and a kind of ginsenoside derivative is provided Novel blank liposome as membrane material, its preparation method and application

Method used

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  • Novel blank liposomes taking ginsenoside derivatives as membrane materials, and preparation method and application thereof
  • Novel blank liposomes taking ginsenoside derivatives as membrane materials, and preparation method and application thereof
  • Novel blank liposomes taking ginsenoside derivatives as membrane materials, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0246] Preparation Example 1 Preparation of Isogeninsenoside Rg3(O)

[0247] Dissolve 10g of isoginsenoside Rg3 (type E) in 20mL of pyridine, add acetic anhydride dropwise under an ice-water bath, control the reaction temperature not to exceed 5°C, and react for 10 hours. TLC detects that the raw material point disappears, and then pour the reaction solution into ice water , extracted 3 times with 200 mL / times of ethyl acetate, combined the organic phases, washed 3 times with 200 mL / times of saturated NaCl, dried with an appropriate amount of anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain iso-Rg3 (type E) acetylated product.

[0248] Dissolve 5 g of the acetylated product of iso-Rg3 (type E) in 50 mL (THF: water 1:1), add 3 mL of 33% hydrogen peroxide, 2 mL of 2 M sodium hydroxide, and react overnight at room temperature. TLC detects that the raw material point disappears, Cool, wash 3 times with 100 mL / time of saturated sodium bicarbona...

preparation Embodiment 3

[0256] Preparation Example 3 Preparation of Ginsenoside Rp1

[0257] Take 1.5 g of ginsenoside Rg5, dissolve it in 150 mL of ethanol, add 300 mg of 5% palladium carbon, stir, and feed hydrogen gas at 40°C for 6 hours. After the reaction, the palladium carbon was removed by filtration, the filtrate was extracted three times with ethyl acetate, the organic phases were combined, and concentrated to dryness under reduced pressure to obtain crude ginsenoside Rp1. Separation by high-pressure chromatography, using C18 as a filler, gradient elution with methanol and water, detection by evaporative light scattering (ELSD), and concentration of the product section to dryness to obtain 0.36g+0.55g of ginsenoside Rp1 with an HPLC purity of more than 98%.

[0258] Ginsenoside Rp1,

[0259] 1 H NMR (δ, 500M): 5.38 (1H, d, J = 7.5Hz), 4.91 (1H, d, J = 7.5Hz), 4.55 (1H, m), 4.45-4.49 (2H, m), 4.23- 4.33(5H,m),4.12-4.14(2H,m),3.90-3.92(3H,m),3.27(1H,m),2.28-2.59(4H,m),2.17(2H,m),1.99- 2.02...

preparation Embodiment 4

[0262] Preparation Example 4 Preparation of Isoginsenoside Rg3H

[0263] Following the same method as Preparation Example 3, the acetylated product of isoginsenoside Rg3 was taken as the starting material, hydrogenated, post-treated, and separated by high-pressure chromatography to obtain the refined product of isoginsenoside Rg3H.

[0264] Isoginsenoside Rg3H,

[0265] 1 H NMR (δ, 500M): 5.37 (1H, d, J = 7.5Hz), 4.91 (1H, d, J = 7.5Hz), 4.55 (1H, m), 4.45-4.49 (2H, m), 4.23- 4.33(5H,m),4.12-4.14(2H,m),3.90-3.92(3H,m),3.27(1H,m),2.28-2.59(2H,m),2.17(1H,m),1.99- 2.02(3H,m),1.80-1.89(3H,m),1.78(3H,d,J=5.7),1.67-1.71(3H,m),1.64(3H,s),1.61(3H,s), 1.41(6H,s),1.35-1.50(10H,m),1.28(3H,s),1.20(1H,m),1.09(3H,m),1.02(1H,m),0.97(3H,s) ,0.96(3H,m),0.79(3H,s),0.74(1H,m).

[0266] 13 C NMR (δ, 125M): 106.3, 105.3, 89.2, 83.6, 82.3, 78.6, 78.4, 78.2, 78.0, 71.9, 71.2, 63.1, 63.0, 77.4, 56.6, 55.0, 51.9, 50.6, 49.4, 48.8, 40.2, 39.9, 39.4, 37.1, 35.4, 32.3, 31.6, 30.0, 29.8, 27.3, 26.9...

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Abstract

The invention discloses novel blank liposomes taking ginsenoside derivatives as membrane materials as well as a preparation method and application thereof. The ginsenoside derivatives used in the novel blank liposomes taking the ginsenoside derivatives as the membrane materials are high in activity and low in hemolytic activity, and can be used as liposome membrane materials for preparing blank liposomes; moreover, structures of some of the compounds are novel. In addition, the novel blank liposomes prepared by using the ginsenoside derivatives meet the requirements for hemolytic activity; andthus, the liposomes are higher in safety, better in film-forming properties and more excellent in stability. Therefore, the liposomes are of important application values.

Description

technical field [0001] The invention relates to a novel blank liposome with ginsenoside derivatives as membrane material, its preparation method and application. Background technique [0002] Ginsenosides have complex and diverse pharmacological activities. In order to highlight the pharmacological effects of individual monomeric saponins, the current research on ginsenosides is mainly focused on the development and utilization of monomeric saponins. Hemolysis is one of the characteristics of some saponins, which becomes the biggest obstacle to the use of monomeric saponins as injections. Total ginseng saponins have no obvious hemolytic effect, but the isolated and purified monomeric saponins have diametrically opposite hemolytic or anti-hemolytic effects, and there is an approximate curve relationship between the strength and concentration of the hemolytic and anti-hemolytic effects . There are few studies on the hemolytic and anti-hemolytic effects of ginsenosides. Accor...

Claims

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Application Information

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IPC IPC(8): A61K9/127A61K47/28A61K45/00A61P35/00A61K8/63A61Q19/00C07J17/00C07J31/00C07J41/00
CPCA61K8/63A61Q19/00A61K9/127A61K31/337C07J17/00A61P35/00A61K8/14C07J17/005C07J31/006C07J41/0055A61K31/704A61K31/7048A61K45/06A61K31/4745A61K31/575A61K31/58A61K2300/00
Inventor 王丹李翀王亚华孟强缪鹏飞詹华杏
Owner XIAMEN GINPOSOME PHARM CO LTD
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