CN103304617A - Phenols-phytosterol functional molecule and preparation method for same - Google Patents
Phenols-phytosterol functional molecule and preparation method for same Download PDFInfo
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- CN103304617A CN103304617A CN2013102199443A CN201310219944A CN103304617A CN 103304617 A CN103304617 A CN 103304617A CN 2013102199443 A CN2013102199443 A CN 2013102199443A CN 201310219944 A CN201310219944 A CN 201310219944A CN 103304617 A CN103304617 A CN 103304617A
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Abstract
The invention discloses a phenols-phytosterol functional molecule and a preparation method for the same. The functional molecule forms an ester group via the carboxyl group of phenols and the hydroxyl group of phytosterol, so as to connect phenols with phytosterol. The invention further discloses the preparation method for the phenols-phytosterol functional molecule. The preparation method comprises the following steps of: mixing phenols, phytosterol and a coupling reagent, performing reaction by stirring, and then performing aftertreatment to obtain phenols-phytosterol. The phenols-phytosterol disclosed by the invention is great in oxidation resistance, wide in application range, simple to use, and capable of being used for industrialized production.
Description
Technical field
The invention belongs to functional food and heath food field, be specifically related to a kind of phenols plant sterol functional molecular and preparation method thereof.
Background technology
Plant sterol is to be present in a class natural constituents in the plant.Experimentation on animalies and human clinical trial's data show in a large number, and plant sterol is a kind of important protective foods composition for reducing blood middle cholesterol content, alleviating cardiovascular disorder generation significance.But free plant sterol solvability in grease is relatively poor, has limited its actual use range.Form plant sterol ester behind plant sterol and the carboxylic esterification, can obviously improve its solubleness.The carbon chain lengths of lipid acid and the effect of saturation degree of lipid acid be to the fusing point of plant sterol ester and fat-soluble, can change the fusing point of sterol ester, the physicals such as fat-soluble by the species composition of selecting lipid acid, to be applicable to dissimilar product.Plant sterol ester has the better effect of fat-soluble and more efficient norcholesterol of specific ionization plant sterol, is a kind of cardiopathic functional food ingredient of desirable reduction serum cholesterol, prevention and treatment coronary atherosclerosis class.
Polyphenol is that a class extensively is present in the poly-hydroxy phenols material in the plant.They all have certain content in leaf, wood, skin, shell and the pulp of plant materials, all contain higher plant polyphenol in fruit, the cereal epidermis.Polyphenol has good antioxygenation, and this is the basis of its all physiologically actives.In a large amount of bodies and experiment in vitro and epidemiologic data show, edible a certain amount of plant polyphenol has prevention and restraining effect to disease.Polyphenol has arteriosclerosis, prevents and treats cardiovascular disorder and anti-inflammatory, anti-allergic effects and the antivirus actions such as coronary heart disease and apoplexy.Modern medicine study proves, a lot of diseases such as histoorgan be aging to be waited all relevantly with the free radical of surplus, and polyphenol has the effect of removing free radical, and the biomacromolecule that free radical brings out damaged plays a protective role.Along with polyphenol chemistry and pharmacological development, people recognize that gradually polyphenol is the natural product that a class has unique physiologically active and pharmacologically active.Along with the rise of current " pursuit nature " consumption idea, polyphenol has broad application prospects in high-tech areas such as pharmacy, biochemistry, daily use chemicals, food and fine chemistry industries.
Summary of the invention
The invention provides a kind of phenols plant sterol functional molecular and preparation method thereof, the antioxidant property of this phenols plant sterol functional molecular improves greatly.
A kind of phenols plant sterol functional molecular, structure is shown in formula I:
In the formula I, R
1Be C
7～C
8Alkyl;
R
2, R
3And R
4Be independently selected from-OH or H.
Among the present invention, form ester group by the carboxyl of phenols and the hydroxyl of plant sterol, phenols and plant sterol are joined together to form the phenols plant sterol, obtain novel polyphenol plant sterol functional molecular, realized the combination of plant sterol and polyphenol at molecular level, made this functional molecular have simultaneously the physiologically active of plant sterol and polyphenol.
As preferably, the R that states
1Be C
7～C
8Thiazolinyl or C
7～C
8Alkyl.。
As preferably, described R
2, R
3And R
4All be-OH.
The preparation method of described phenols plant sterol functional molecular comprises the steps:
Aldehydes matter and plant sterol are mixed, add coupling reagent, stir and react, reaction finishes to carry out aftertreatment and obtains described phenols plant sterol functional molecular;
The structure of described aldehydes matter is shown in formula II:
The structure of described plant sterol is shown in formula III:
In the formula III, R
1Be C
7～C
8Alkyl;
In the formula II, R
2, R
3And R
4Be independently selected from-OH or H.
The purity of the phenols plant sterol functional molecular that this preparation method obtains is high, has preferably antioxidant property.
As preferably, described aldehydes matter is gallic acid, the gallic acid low price, and the good product performance that makes, and be easy to be absorbed.
Described plant sterol can be buied from the market, can use the mixture of sterling or various plants sterol.As preferably, described plant sterol is at least a in stigmasterol, brassicasterol, ergosterol and the β-sitosterol.
As preferably, described coupling reagent is N, N '-dicyclohexylcarbodiimide.N, N '-dicyclohexylcarbodiimide cheaply is easy to get, and the linked reaction between phenols and the plant sterol is had preferably effect.
As preferably, the mol ratio of described phenols, plant sterol and coupling reagent is 1:0.5-50:0.5-50.This molar ratio range is conducive to the abundant conversion of raw material.
As preferably, described aftertreatment comprises:
(1) organic solvent is joined in the reaction system of reacting after finishing, extraction product is in organic phase;
(2) organic phase after will extracting is concentrated, obtains phenols plant sterol sterling through chromatographic separation.
As further preferred, described organic solvent comprises a kind of in ethyl acetate, ether, chloroform, methylene dichloride, sherwood oil, normal hexane, the t-butyl methyl ether, and these organic solvents are better to the solubility property of product, and is easy to volatilization and removes.
Reaction of the present invention is at room temperature carried out.
The present invention has following advantage and effect with respect to existing plant sterol ester:
(1) phenols plant sterol ester of the present invention has good anti-oxidant function.
(2) phenols plant sterol ester of the present invention has good antioxidant property in grease.
(3) phenols plant sterol ester low price of the present invention is applicable to suitability for industrialized production and uses.
Embodiment
The present invention is described in further detail below in conjunction with embodiment, but embodiments of the present invention are not limited to this.
Embodiment 1
Gallic acid (510.4mg), plant sterol (412.7mg) and N, N '-dicyclohexylcarbodiimide (617.0mg) be stirring reaction 2 hours at room temperature, and question response is used chloroform extraction after finishing, and obtains gallic acid plant sterol 21% behind chromatogram purification.
The used plant sterol of the present embodiment is buied from the market, comprise 30% stigmasterol (stigmasterol), 5% brassicasterol (brassicasterol), 20% ergosterol (campesterol) and 40% β-sitosterol (β-sitosterol), total purity 95%.
The structure determination data:
1Show gallic acid aromatic ring characteristic peak about H NMR7.25ppm, IR1702cm
-1About show the ester group charateristic avsorption band, mass spectrum shows the wherein molecular ion peak 552.78,564.80 of principal constituent.These digital proofs the exactness of synthetic structure.
Embodiment 2
Gallic acid (600.2mg), plant sterol (identical with embodiment 1) (412.7mg) and N, N '-dicyclohexylcarbodiimide (617.0mg) stirring reaction 2.5 hours is used after question response finishes
Ethyl acetate extraction obtains gallic acid plant sterol 26% behind chromatogram purification.
Embodiment 3
Gallic acid (480.0mg), plant sterol (identical with embodiment 1) (412.7) and N, N '-dicyclohexylcarbodiimide (550.0mg) stirring reaction 2.2 hours, question response is used dichloromethane extraction after finishing, and obtains gallic acid plant sterol 23% behind chromatogram purification.
Anti-oxidant activity test: use 743Rancimat Oxidation of Fat and Oils determinator, antioxidant property in the imperial fish soybean oil of gold and lard is measured, wherein contrast has not plant sterol, the VE(vitamin-E before transforming), the BHA(butylated hydroxy anisole), BHT(2, the 6-di-tert-butyl-4-methy phenol), addition is the 0.04%(massfraction).The test result of the increase rate of induction time is as shown in table 1, and calculation formula is: the increase rate of induction time (induction time of=(induction time of the induction time of experimental group-blank group)/blank group).
Table 1 anti-oxidant activity test result
aThe addition of plant sterol is the 1%(massfraction of golden imperial fish soybean oil).
Claims (10)
1. a phenols plant sterol functional molecular is characterized in that, structure is shown in formula I:
In the formula I, R
1Be C
7～C
8Alkyl;
R
2, R
3And R
4Be independently selected from-OH or H.
2. phenols plant sterol functional molecular according to claim 1 is characterized in that described R
1Be C
7～C
8Thiazolinyl or C
7～C
8Alkyl.
3. phenols plant sterol functional molecular according to claim 1 and 2 is characterized in that described R
2, R
3And R
4All be-OH.
4. the preparation method such as each described phenols plant sterol functional molecular of claim 1～3 is characterized in that, comprises the steps:
Aldehydes matter and plant sterol are mixed, add coupling reagent, stir and react, reaction finishes to carry out aftertreatment and obtains described phenols plant sterol functional molecular;
The structure of described aldehydes matter is shown in formula II:
The structure of described plant sterol is shown in formula III:
In the formula III, R
1Be C
7～C
8Alkyl;
In the formula II, R
2, R
3And R
4Be independently selected from-OH or H.
5. the preparation method of phenols plant sterol functional molecular according to claim 4 is characterized in that, described aldehydes matter is gallic acid.
6. according to claim 4 or the preparation method of 5 described phenols plant sterol functional moleculars, it is characterized in that, described plant sterol is at least a in stigmasterol, brassicasterol, ergosterol and the β-sitosterol.
7. the preparation method of phenols plant sterol functional molecular according to claim 4 is characterized in that, described coupling reagent is N, N '-dicyclohexylcarbodiimide.
8. the preparation method of phenols plant sterol functional molecular according to claim 4 is characterized in that, the mol ratio of described aldehydes matter, plant sterol and coupling reagent is 1:0.5-50:0.5-50.
9. the preparation method of phenols plant sterol functional molecular according to claim 4 is characterized in that, described aftertreatment comprises:
(1) organic solvent is joined in the reaction system of reacting after finishing, extraction product is in organic phase;
(2) organic phase after will extracting is concentrated, obtains phenols plant sterol sterling through chromatographic separation.
10. the preparation method of phenols plant sterol functional molecular according to claim 9 is characterized in that, described organic solvent comprises a kind of in ethyl acetate, ether, chloroform, methylene dichloride, sherwood oil, normal hexane, the t-butyl methyl ether.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672291A (en) * | 2015-01-30 | 2015-06-03 | 江南大学 | Preparation method of gallate phytosterol ester |
| CN107973835A (en) * | 2016-10-21 | 2018-05-01 | 浙江大学 | Natural mixed phytosterin catechin, preparation method and application |
| CN108976273A (en) * | 2018-08-20 | 2018-12-11 | 浙江大学 | A kind of nutgall acyl stigmasterol functional molecular and preparation method thereof |
| CN108976274A (en) * | 2018-08-20 | 2018-12-11 | 浙江大学 | A kind of nutgall acyl sitosterol functional molecular and preparation method thereof |
| CN113679039A (en) * | 2021-05-12 | 2021-11-23 | 浙江大学 | Gallic acid polyethylene glycol ester protein carrier synergist and preparation method and application thereof |
-
2013
- 2013-06-04 CN CN201310219944.3A patent/CN103304617B/en not_active Expired - Fee Related
Non-Patent Citations (4)
| Title |
|---|
| IKURO ABE,ET AL.: "Potent and Selective Inhibition of Squalene Epoxidase by Synthetic Galloyl Esters", 《BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS》 * |
| TONG WANG,ET AL.: "Antioxidant Activity of Phytosterols, Oryzanol,and Other Phytosterol Conjugates", 《JAOCS》 * |
| 谢晓艳等: "没食子酸体外抗氧化作用研究", 《重庆医科大学学报》 * |
| 赵文红等: "阿魏酸体外抗氧化作用研究", 《食品科学》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672291A (en) * | 2015-01-30 | 2015-06-03 | 江南大学 | Preparation method of gallate phytosterol ester |
| CN107973835A (en) * | 2016-10-21 | 2018-05-01 | 浙江大学 | Natural mixed phytosterin catechin, preparation method and application |
| CN107973835B (en) * | 2016-10-21 | 2020-05-22 | 浙江大学 | Natural mixed phytosterol catechin, preparation method and application |
| CN108976273A (en) * | 2018-08-20 | 2018-12-11 | 浙江大学 | A kind of nutgall acyl stigmasterol functional molecular and preparation method thereof |
| CN108976274A (en) * | 2018-08-20 | 2018-12-11 | 浙江大学 | A kind of nutgall acyl sitosterol functional molecular and preparation method thereof |
| CN113679039A (en) * | 2021-05-12 | 2021-11-23 | 浙江大学 | Gallic acid polyethylene glycol ester protein carrier synergist and preparation method and application thereof |
| CN113679039B (en) * | 2021-05-12 | 2023-05-09 | 浙江大学 | Polyethylene glycol gallate protein carrier synergist and preparation method and application thereof |
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|---|---|
| CN103304617B (en) | 2015-08-12 |
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