Theasapogenol derivative with antibacterial effect as well as preparation method and application thereof

A technology of tea saponin and derivatives, which is applied in the field of health and medicine, can solve the problems of unfavorable entry into bacteria and fungal cells, lack of direct sterilization, large molecular weight structure, etc., and achieve small structure, improved antibacterial activity, and simple preparation process Effect

Inactive Publication Date: 2012-07-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The sugar body part of tea saponin is a polysaccharide structure composed of galactose, arabinose, xylose, etc., with a large molecular weight structure, which is not conducive to its entry into bacterial and fungal cells, so its antibacterial concentration is high, and it cannot achieve the purpose of direct sterilization

Method used

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  • Theasapogenol derivative with antibacterial effect as well as preparation method and application thereof
  • Theasapogenol derivative with antibacterial effect as well as preparation method and application thereof
  • Theasapogenol derivative with antibacterial effect as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Theosapogenin (C 30 h 50 o 5 ) solid 100g, added to 300mL of pyridine, heated to 50°C to dissolve, added triphenylchloromethane (56.7g) in an equimolar amount to the tea saponin, kept warm (50°C) and stirred for 8 hours; added tea saponin Acetic anhydride (41.6g) with 2 times the molar amount was stirred at 50°C for 15h; 9.4mL of formic acid was added, the reaction temperature was 100°C, and refluxed for 1h; then 4-dioxolane-1,1-diethyloxybutyl was added 45g of alkane, reaction temperature 70°C, stirred for 9h; cooled to 20°C, added 56g of potassium carbonate, stirred for 1h, evaporated pyridine under reduced pressure, added 1000mL of water to wash, added methanol to crystallize water-insoluble matter, dried in vacuo, prepared 34 g of thea-sapogenin derivatives were obtained.

[0033] The structural analysis of the product shows that MS: m / z 662; the elemental composition is: C70.66%, H10.03%, O19.31%, and its molecular formula is C 39 h 66 o 8 , 1 H-NMR with 13...

Embodiment 2

[0035] Theosapogenin (C 30 h 50 o 5 ) solid 100g, added to 300mL of pyridine, dissolved at room temperature (25°C), added triphenylchloromethane (85g) according to 1.5 times the molar amount of teasapogenin, and kept stirring for 12 hours; Amount of acetic anhydride (83.2g), stirred at 70°C for 10h; added 14mL of formic acid, the reaction temperature was 105°C, and refluxed for 1h; then added 45g of 4-dioxolane-1,1-diethyloxybutane, the reaction temperature Stir and react at 75°C for 6h; after cooling to 30°C, add 112g of potassium carbonate, stir for 1h, evaporate pyridine under reduced pressure, add 1000mL of water to wash, add water-insoluble matter into methanol to crystallize, and dry in vacuo to obtain 49g of tea saponin meta derivatives.

[0036] The structural analysis data of the product are the same as in Example 1. The product proved to be 28-(4-dioxolane-1-ethyloxybutoxy)-teasapogenol.

Embodiment 3

[0038] Theosapogenin (C 30 h 50 o 5 ) solid 100g, added to 300mL of pyridine, heated to 40°C to dissolve, added triphenylchloromethane (68g) according to 1.2 times the molar amount of teasapogenin, and kept stirring for 16 hours; Acetic anhydride (62.4g) was stirred at 80°C for 8h; 11.3mL of formic acid was added, the reaction temperature was 110°C, and refluxed for 1h; Stir at 80°C for 3 hours; after cooling to 25°C, add 84g of potassium carbonate, stir for 1h, evaporate pyridine under reduced pressure, add 1000mL of water to wash, add methanol to crystallize water-insoluble matter, and vacuum dry to obtain 43g of tea saponin meta derivatives.

[0039] The structural analysis data of the product are the same as in Example 1. The product proved to be 28-(4-dioxolane-1-ethyloxybutoxy)-teasapogenol.

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Abstract

The invention discloses a theasapogenol derivative with an antibacterial effect as well as a preparation method and application thereof. The theasapogenol derivative with an antibacterial effect is 28-(4-dioxolane-1-ethoxybutoxy)-tea sapogenol and is prepared by the following steps of: making triphenylchloromethane react with theasapogenol for protecting a primary hydroxyl on theasapogenol C28; making acetic anhydride react with theasapogenol for protecting a secondary hydroxyl on the theasapogenol; adding a triphenylmethyl removing protective agent, removing triphenylmethyl and leading the primary hydroxyl on the theasapogenol C28 to protect; adding 4-dioxolame-1,1-diethyloxy butane for reacting and connecting with the theasapogenol; and finally, adding an acetyl removing protective agent, removing the acetyl on the theasapogenol and crystallizing to obtain the theasapogenol derivative shown as the formula I. The antibacterial activity of the theasapogenol derivative of the inventionis obviously improved, and the defect of low bacteriostatic capabiity of the traditional theasapogenol is overcome.

Description

technical field [0001] The invention relates to the fields of sanitation and medicine, in particular to a theosaponin derivative 28-(4-dioxolane-1-ethyloxybutoxy)-teasapogeninol with antibacterial effect and a preparation method thereof , and its application for the preparation of antibacterial drugs. Background technique [0002] Antibacterial drugs refer to drugs with bactericidal and bacteriostatic activities, and are currently the most widely used class of drugs in clinical practice. However, with the widespread use and even abuse of antimicrobial agents, bacterial drug resistance is increasing year by year. Drug-resistant bacterial infections not only seriously endanger human health, but also become a worldwide thorny problem. In the face of drug-resistant bacterial infections that are increasingly harmful to human health, it is crucial to accelerate the development of safe and effective new antibacterial drugs. Regrettably, since the 1980s, the number of new antibact...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/58A61P31/04
Inventor 叶勇罗月婷
Owner SOUTH CHINA UNIV OF TECH
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