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Preparation method and application of lipoic acid sterol/stanol ester

A technology of lipoic acid sterol and stanol ester, applied in the directions of steroids, antidote, organic chemistry, etc., to achieve the effects of good safety, short time consumption and low cost

Pending Publication Date: 2021-11-02
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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There is also no report on lipoic acid sterol / stanol ester in improving oxidative stress

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  • Preparation method and application of lipoic acid sterol/stanol ester

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[0020] A preparation method of lipoic acid sterol / stanol ester, comprising the following steps:

[0021] Step S1, weighing a certain amount of sterols / stanols, lipoic acid or lipoic acid derivatives, enzymes and dehydrating agents respectively in a reaction bottle, adding a certain amount of reaction solvent, sealing and reacting at a certain temperature for a certain period of time, the The enzyme is Candida 99-125 lipase or Atomyces sterol esterase;

[0022] Step S2, after the reaction, take out the reaction solution, filter to remove the enzyme and dehydrating agent, remove the reaction solvent by rotary evaporation to obtain the crude sterol / stanol lipoate, and obtain the pure sterol / stanol lipoate after separation.

[0023] Described sterol / stanol is in sitosterol, stigmasterol, ergosterol, brassicasterol, campesterol, fucosterol, sitostanol, stigmasterol, brassicostanol, campestanol A mixture of one or more than one in any proportion.

[0024] The lipoic acid or lipoic...

Embodiment 1

[0030] Embodiment 1: A kind of preparation method of lipoic acid sitosterol ester

[0031] Add 120mmol / L lipoic acid methyl ester, 60mmol / L sitosterol, 60g / L Ophiostomapicae sterol esterase (US Sigma), 80g / L molecular sieves in the reaction flask, add n-hexane, and place at 55°C Reaction 6h. After the reaction was completed, the lipase and molecular sieves in the reaction flask were removed, the supernatant was collected, and rotary evaporation was performed to obtain the crude lipoic acid sitosterol ester.

[0032]The structural characterization data of the product are as follows: Infrared spectrum: 2932cm -1 The absorption peak is -CH 3 Telescopic vibration absorption, 2868cm -1 The absorption peak is -CH 2 stretching vibration absorption, 1462cm -1 at -CH 3 of bending vibration absorption, 1380cm -1 for -CH 2 of bending vibration absorption, 1729cm -1 The strong absorption peak at is the stretching vibration absorption signal of carbonyl C=O, 1174cm -1 The moderat...

Embodiment 2

[0035] Embodiment 2: A kind of preparation method of lipoic acid phytostanol ester

[0036] Add successively 120mmol / L lipoic acid, 80mmol / L phytostanol (the phytostanol is 44.2% β-sitostanol+33.8% stigmasteranol+11.7% campestanol+9.3% rapeseed stanol), 40g / L Candida 99-125 lipase (Beijing Kaitai), 120g / L molecular sieves in a reaction flask, add cyclohexane, and place at 50°C for 12h. After the reaction is completed, the lipase and molecular sieves in the reaction flask are removed, the supernatant is collected, and rotary evaporated to obtain the crude lipoic acid phytostanol ester.

[0037] The structural characterization data of the product are as follows:

[0038] Infrared spectrum: 2935cm -1 The absorption peak is -CH 3 Telescopic vibration absorption, 1463cm -1 at -CH 3 of bending vibration absorption, 1729cm -1 The strong absorption peak at is the stretching vibration absorption signal of carbonyl C=O, 1175cm -1 The moderate intensity peak at is the stretching v...

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Abstract

The invention provides a preparation method and application of lipoic acid sterol / stanol ester, and the preparation method comprises the following steps: S1, respectively weighing sterol / stanol, lipoic acid or a lipoic acid derivative, an enzyme and a dehydrating agent in a reaction flask, adding a reaction solvent for reaction, the enzyme being candida 99-125 lipase or muscardine fungus sterol esterase; and S2, after the reaction is finished, taking out reaction liquid, filtering to remove the enzyme and the dehydrating agent, removing the reaction solvent to obtain a sterol / stanol lipoic acid ester crude product, and separating to obtain a sterol / stanol lipoic acid ester pure product. The lipase is used as a catalyst to catalyze the reaction of sterol / stanol and lipoic acid / lipoic acid derivatives to synthesize lipoic acid sterol / stanol ester, the product conversion rate is greater than or equal to 95%, and the yield is greater than 90%. The method has the advantages of high conversion rate, short time consumption, simple process operation, low energy consumption, mild reaction conditions, greenness, environmental protection and the like.

Description

technical field [0001] The invention belongs to the technical field of nutrition, health and health care, and in particular relates to a preparation method of lipoic acid sterol ester or lipoic acid stanol ester and an application as an antioxidant. Background technique [0002] Lipoic acid, also known as α-lipoic acid, is a B vitamin widely found in spinach, tomato and other plants. It was first isolated from pig liver by Reed in 1951. Alpha-lipoic acid has excellent antioxidant activity and is known as "universal antioxidant". Studies have shown that lipoic acid has a strong ability to scavenge free radicals, and when used in combination with antioxidants such as vitamin C, vitamin E, glutathione, and coenzyme Q10, it can help these antioxidants regenerate. In addition, lipoic acid can anti-aging, effectively inhibit tumor angiogenesis, enhance the body's immunity, increase tumor sensitivity to chemotherapy drugs, and reverse tumor drug resistance. However, lipoic acid h...

Claims

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Application Information

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IPC IPC(8): C12P33/20C12P33/00C07J33/00A61P39/06
CPCC12P33/20C12P33/00C07J33/002A61P39/06
Inventor 何文森孙玉莹王庆芝刘懿航杨浩楠李俊杰徐斌
Owner JIANGSU UNIV
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