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Preparation method of plant polyprenol with bacteriostatic and antioxidant activity and hydrogenated derivative thereof

An antioxidant activity, polyprenol technology, applied in the field of biomedicine, can solve the problems of no report on the purification and isolation of polyprenol, little research on antioxidant activity and bacteriostatic biological activity, etc.

Active Publication Date: 2012-11-14
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, the purification of polyprenol is mostly used for the separation of silica gel column chromatography at home and abroad. There is no report on the purification and separation of polyprenol by urea embedding method at home and abroad, especially for polyprenol as an intermediate hydrogenation product and its resistance. Oxidative and bacteriostatic biological activities are rarely studied

Method used

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  • Preparation method of plant polyprenol with bacteriostatic and antioxidant activity and hydrogenated derivative thereof
  • Preparation method of plant polyprenol with bacteriostatic and antioxidant activity and hydrogenated derivative thereof
  • Preparation method of plant polyprenol with bacteriostatic and antioxidant activity and hydrogenated derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation method of polyprenyl alcohol and its hydrogenated derivatives

[0040] A method for preparing plant polyprenol and its hydrogenated derivatives with antibacterial and antioxidative activities, comprising the following steps:

[0041] The first step, polyprenol lipid extraction: fresh plant leaves rich in polyprenol lipids, such as one of ginkgo leaves, pine needles, and mulberry leaves, preferably ginkgo leaves, are dried in the shade at room temperature and crushed to 100 For the powder below the mesh, add anhydrous acetone or any solvent in C1-C3 alcohol, preferably acetone; mix the leaves with the solvent at a mass ratio of 1:20, soak at room temperature for 10-72 hours, preferably 24-48 hours; or leaves After mixing with the solvent at a mass ratio of 1:20, extract by microwave or ultrasonic extraction at 10°C to 80°C for 10 to 60 minutes, preferably ultrasonic, at an extraction temperature of 10°C to 40°C, for 10 to 30 minutes, and repeat the ...

Embodiment 2

[0050] Embodiment 2 polyprenol hydrogenation reaction single factor test

[0051] 1. Selection of reaction time

[0052] The reaction temperature is fixed at 30°C, the solvent is dichloromethane:methanol=2:1 (V / V), and the catalyst is (S)-Ru(OAc) 2 (BINAP), the mass ratio of polyprenol and catalyst is 100:1, H pressure 10MPa, the reaction time is 3h, 6h, 9h, 12h, 18h, 24h, 36h, and the supernatant is taken for HPLC detection in the reaction process , and the reaction conversions were 6.8%, 16%, 22%, 32%, 41%, 56% and 58%, respectively. With the increase of the reaction time, the yield increases gradually and is basically stable after 24 hours, so the preferred reaction time is 24 hours.

[0053] 2. Selection of catalyst dosage

[0054] The reaction temperature is fixed at 20°C, and the catalyst is Ru(BINAP)(OAc) 2 , solvent dichloromethane:methanol=3:1(V / V), H 2 The pressure is 12MPa, the reaction time is 24h, the mass ratio of polyprenol to catalyst is 50:1, 100:1, 200:1...

Embodiment 3

[0057] The purification experiment of embodiment 3 polyprenol

[0058] 1. Take 1 kg of mulberry leaves, crush them into 40-mesh powder, add 20 kg of anhydrous acetone, soak at room temperature for 50 hours, filter, then add 15 kg of anhydrous acetone, ultrasonically extract at 40°C for 20 minutes, combine the extracts, and recover the organic solvent in a vacuum , the concentrate is polyprenol lipid ointment;

[0059] 2. Four different types of adsorption carriers were screened, including silica gel, activated carbon for monosodium glutamate decolorization, polyamide resin, and attapulgite. Pure urea and the mass ratio of urea and adsorption carrier were 10:1, 5:1, 5:2, : 3, 1: 1 etc. 5 kinds of different mass ratios are carried out single-factor screening to the purification of polyprenol lipid ointment, and the results are shown in Table 1-2.

[0060] Table 1 Purification results of different proportions of urea silica gel

[0061]

[0062] From Table 1, using silica ge...

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Abstract

The invention discloses a preparation method of plant polyprenol with bacteriostatic and antioxidant activity and a hydrogenated derivative thereof, which comprises the following steps of: taking gingko, pine needles and folium mori as raw materials, extracting a polyprenol lipid ointment through a non-polar solvent, including with a filler in urea alcohol solution, crystallizing, preparing a polyprenol type lipid urea inclusion compound and purifying polyprenol lipid through column chromatography; adding into 5-40 percent by weight of caustic soda solution for saponification reaction and preparing more than 95 percent by weight of polyprenol; adding a catalyst in methylene dichloride-methanol solution and ensuring that the mass ratio of the polyprenol to the catalyst is 80-200:1, the reaction pressure is 8-20 MPa, the reaction time is 18-48 hours, and the reaction temperature is 10-50 DEG C; and after reaction, filtering and concentrating under vacuum, wherein a concentrate is a polyprenol hydrogenated derivative. The polyprenol and the hydrogenated derivative thereof prepared by the method play roles in restraining staphylococcus aureus (Sa.), escherichia coli (Ec.), bacillus subtilis and salmonella and clearing superoxide free radicals and hydroxyl free radicals.

Description

technical field [0001] The invention relates to a method for preparing plant polyprenol and its hydrogenated derivatives with antibacterial and antioxidative activities, belonging to the field of biomedicine. technical background [0002] Polyprenol is widely found in gymnosperms and angiosperms, and it also exists in the organs of bacteria, fungi and mammals. Its structure is similar to that of dolichol with biological activity, so it is known as the best synthetic Intermediates, so the birch-type polyprenol extracted from plants is similar to the dolichol in the human body, so extracting and separating plant polyprenol and synthesizing dolicenol has become a new drug development concept. [0003] Polyprenol is based on C 5 Lipid compounds with isopentenyl as the structural unit can be divided structurally: betulin type ω-(trans) 2 -(cis) n -OH, fika alcohol type ω-(trans) 3 -(cis) n -OH and solanesol type omega-(trans) n -OH, Wang Chengzhang et al. isolated seven bet...

Claims

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Application Information

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IPC IPC(8): C07C33/02C07C29/74C07C29/17A61P31/04A61P39/06
CPCY02A50/30
Inventor 王成章陶冉周彦
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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