CN108813609A - A kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound - Google Patents
A kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound Download PDFInfo
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- CN108813609A CN108813609A CN201810513262.6A CN201810513262A CN108813609A CN 108813609 A CN108813609 A CN 108813609A CN 201810513262 A CN201810513262 A CN 201810513262A CN 108813609 A CN108813609 A CN 108813609A
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- beta
- sulfobutyl ether
- cyclodextrin
- seed extract
- grape seed
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- 229940097346 sulfobutylether-beta-cyclodextrin Drugs 0.000 title claims abstract description 87
- 235000002532 grape seed extract Nutrition 0.000 title claims abstract description 79
- 229940087603 grape seed extract Drugs 0.000 title claims abstract description 78
- 239000001717 vitis vinifera seed extract Substances 0.000 title claims abstract description 78
- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 230000010355 oscillation Effects 0.000 claims abstract description 35
- 238000013019 agitation Methods 0.000 claims abstract description 28
- 239000000843 powder Substances 0.000 claims abstract description 25
- 239000000243 solution Substances 0.000 claims abstract description 25
- 239000000706 filtrate Substances 0.000 claims abstract description 16
- 239000011259 mixed solution Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012153 distilled water Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000012982 microporous membrane Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims description 4
- 235000015110 jellies Nutrition 0.000 claims 1
- 239000008274 jelly Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 31
- 238000002835 absorbance Methods 0.000 description 19
- 238000012360 testing method Methods 0.000 description 12
- 229920000858 Cyclodextrin Polymers 0.000 description 11
- 239000001116 FEMA 4028 Substances 0.000 description 9
- 235000014787 Vitis vinifera Nutrition 0.000 description 9
- 229960004853 betadex Drugs 0.000 description 9
- 241000219095 Vitis Species 0.000 description 8
- 235000009754 Vitis X bourquina Nutrition 0.000 description 8
- 235000012333 Vitis X labruscana Nutrition 0.000 description 8
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 8
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 7
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000006069 physical mixture Substances 0.000 description 4
- 229920002414 procyanidin Polymers 0.000 description 4
- -1 sulfobutyl Chemical group 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 description 2
- 244000194101 Ginkgo biloba Species 0.000 description 2
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 244000131316 Panax pseudoginseng Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/30—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation
- A23L5/32—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation using phonon wave energy, e.g. sound or ultrasonic waves
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
The present invention provides a kind of preparation methods of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, include the following steps：S1. sulfobutyl ether-beta-cyclodextrin is placed in container, distilled water is added and is uniformly dissolved obtained sulfobutyl ether-beta-cyclodextrin solution；S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature, side edged sonic oscillation, it is placed on magnetic agitation in constant temperature blender with magnetic force after grape seed extract powder has been added, obtains mixed solution after cooled to room temperature；S3. the obtained mixed solution of step S2 is obtained into filtrate with filtering with microporous membrane, puts the filtrate into -20 DEG C of refrigerator and freezes for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound after taking-up.The photostability of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound produced by the present invention, thermal stability and bioavailability are preferable.
Description
Technical field
The present invention relates to a kind of inclusion compounds, include more particularly to a kind of grape seed extract sulfobutyl ether-beta-cyclodextrin
The preparation method of object.
Background technique
China is grape big producer, and up to the present vinegrowing area is up to 560,000 hm2, total output up to 8,430,000 tons,
The yield of Wine grape is wherein made at 1,000,000 tons or so.Grape pip accounts for about the 7~10% of grape weight, is often only grape in this way
The grape pip that wine production generates just reaches tens of thousands of tons.With the development of wine industry, grape pip functional components are ground
Study carefully and development and utilization have very important significance.
Main component in grape seed extract (grape seed extraction, GSE) is procyanidine
(proanthocyanidin, PC) is mainly formed by catechin and epicatechin for monomer polymerization.Procyanidine is very strong anti-
Oxidant and free radical scavenger can prevent many diseases, and epidemiology and biology confirm, good for health, can give protection against cancer, is anti-
Cardiovascular disorder, obesity, diabetes and nerve fiber are degenerated, and artery sclerosis caused by the oxidation because of low-density lipoprotein can be reduced
Risk.Procyanidine good water solubility, is easily absorbed by organisms, and bioavilability is up to 90% or more, but property is unstable, light-exposed
Easily decompose, the moisture absorption, be added separately to it is more difficult in food, to limit it in the application of field of food.(bibliography：Wu
Intelligent, Yuan Chunlong, Song Yangbo are praised, etc..It grape pip functional components and its answers, daily chemical industry, 2011,41 (3)：216-221,
228..Duan Guoping, Liu Xiaoli, Zhao Piwen, etc..The Pharmacological Advancement of grape pip procyanidin, global traditional Chinese medicine, 2014
(4)：313-316.Wu Chun, Zhang Yan, Xu Liping.The research of procyanidine microcapsules release dynamics, chemistry and bonding, 2007,
29(3)：172-175.)
Sulfobutyl ether-beta-cyclodextrin (sulfobutyl ether- β-cyclodextrin, SBE- β-CD) is a kind of ion
The beta-cyclodextrin derivative of type.Compared with beta-cyclodextrin, sulfobutyl ether-beta-cyclodextrin has that high water solubility, renal toxicity be low, haemolysis
Act on the advantages that small.Studies have shown that its solubility for being remarkably improved insoluble drug, stability and bioavilability, make
It is boundless for a kind of new type medicinal stuff application prospect.(bibliography：Gu Fugen, Gao Yongliang, Cui Fude.Sulfobutyl ether-β-
Cyclodextrin and its application in pharmacy, Chinese Journal of New Drugs, 2004,13 (1)：15-19.).
Application No. is the Chinese inventions of CN201210146002.2 to disclose " using grape seed extract as the hard capsule of raw material
And preparation method thereof ", which includes capsule shell and content, and it is main that the content, which is with grape seed extract,
Raw material is aided with gingko powder and is made, and raw material is according to weight percent：Grape seed extract 94%, gingko powder 6%；Its
In, content >=90% of Procyanidin in Grape Seed Extracts.Although the invention solves capsule curative effect low, and has certain secondary
The technical issues of effect, but still unresolved grape seed extract photostability, thermal stability and bioavailability is lower asks
Topic.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compounds
Preparation method, the photostability of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound made from this method, thermal stability and
Bioavailability is preferable.
In order to solve the above technical problems, the technical scheme is that：
A kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, distilled water is added and is uniformly dissolved obtained sulfobutyl ether-β-ring
Dextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
Side edged sonic oscillation is placed on magnetic agitation in constant temperature blender with magnetic force after grape seed extract powder has been added, naturally cold
But to obtaining mixed solution after room temperature；
S3. the obtained mixed solution of step S2 is obtained into filtrate with filtering with microporous membrane, puts the filtrate into -20 DEG C of refrigerator
Middle freezing is immediately placed in freeze drier drying for 24 hours for 24 hours, after taking-up, up to grape seed extract sulfobutyl ether-β-ring after taking-up
Cyclodextrin inclusion compound.
Further, in step S1 of the present invention, the mass fraction of sulfobutyl ether-beta-cyclodextrin solution is 20%.
Further, in step S2 of the present invention, the weight of grape seed extract powder is sulfobutyl ether-beta-cyclodextrin
The 0.01-0.1% of weight.
Further, in step S2 of the present invention, the ultrasonic power of sonic oscillation is 250W, and the frequency of sonic oscillation is
40Khz, the temperature of sonic oscillation are 50 DEG C.
Further, in step S2 of the present invention, the temperature of magnetic agitation is 30-50 DEG C, and the time of magnetic agitation is
90-150min, the speed of magnetic agitation are 200-600r/min.
Further, in step S3 of the present invention, the aperture of miillpore filter is 0.2 μm.
Compared with prior art, the invention has the advantages that：
Grape seed extract is incorporated in the internal cavities of sulfobutyl ether-beta-cyclodextrin by the present invention by solution stirring method
Inclusion compound is formd, sulfobutyl ether-beta-cyclodextrin can effectively improve the photostability of grape seed extract, thermal stability, biology
Utilization rate and solubility in water, expand application of the grape seed extract in field of food；In addition, in step S2
Sonic oscillation operates the inclusion rate for also helping the solubility and inclusion compound that further increase grape seed extract in water.
Detailed description of the invention
The drawings described herein are used to provide a further understanding of the present invention, constitutes part of this application, not
Inappropriate limitation of the present invention is constituted, in the accompanying drawings：
Fig. 1 is the field emission scanning electron microscope figure of four kinds of substances；
Wherein, a is grape seed extract, and b is sulfobutyl ether-beta-cyclodextrin, and c is grape seed extract and sulfobutyl ether-
Beta-cyclodextrin physical mixture, d are grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound prepared by the embodiment of the present invention 1；
Fig. 2 is the infrared spectrum analysis spectrogram of grape seed extract；
Fig. 3 is the infrared spectrum analysis spectrogram of sulfobutyl ether-beta-cyclodextrin；
Fig. 4 is the infrared spectrum analysis spectrogram of grape seed extract and sulfobutyl ether-beta-cyclodextrin physical mixture；
Fig. 5 is the infrared spectroscopy of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound prepared by the embodiment of the present invention 1
Analysis of spectra.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be described in detail, herein illustrative embodiments and their description of the invention
For explaining the present invention, but it is not as a limitation of the invention.
Embodiment 1
The preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, it is 20% that distilled water, which is added, and is uniformly dissolved obtained mass fraction
Sulfobutyl ether-beta-cyclodextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
The weight of grape seed extract powder is the 0.04% of sulfobutyl ether-beta-cyclodextrin weight, side edged sonic oscillation, sonic oscillation
Ultrasonic power be 250W, the frequency of sonic oscillation is 40Khz, and the temperature of sonic oscillation is 50 DEG C, to grape seed extract powder
End is placed on magnetic agitation in constant temperature blender with magnetic force after being added, and the temperature of magnetic agitation is 40 DEG C, and the time of magnetic agitation is
120min, the speed of magnetic agitation are 600r/min, obtain mixed solution after cooled to room temperature；
S3. the mixed solution that step S2 is obtained is obtained into filtrate with the filtering with microporous membrane that aperture is 0.2 μm, filtrate is put
Enter and freezed in -20 DEG C of refrigerator for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract after taking-up
Sulfobutyl ether-beta-cyclodextrin inclusion compound.
By grape seed extract, sulfobutyl ether-beta-cyclodextrin, grape seed extract and sulfobutyl ether-beta-cyclodextrin physics
Grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound prepared by mixture and embodiment 1 is used after gold-plated pretreatment
Field emission scanning electron microscope observes its morphological feature.As a result as shown in Figure 1：For without fixed on grape seed extract morphology
The spherical particle of shape, and sulfobutyl ether-beta-cyclodextrin is the amorphous spherical shape for having cavity, grape seed extract and sulfobutyl ether-
There are two types of the presence of particle in beta-cyclodextrin physical mixture, and include in grape seed extract sulfobutyl ether-beta-cyclodextrin
In object, there is form that is irregular, being totally different from grape seed extract and SBE- β-CD, the form of Subjective and Objective disappears,
There is a presence of some small amorphous irregular small aggregations, the generation of inclusion compound of this preliminary proof.
KBr tabletting is respectively prepared in above-mentioned four kinds of substances, then uses Fourier Transform Infrared Spectrometer, spectral region
4000~400cm-1, scanning times 23 times.Measurement result is as shown in Figure 2-5：Grape seed extract is in 3292cm in Fig. 1-1It deposits at place
In the stretching vibration peak of O-H key, feature skeletal vibration is concentrated mainly on 1000~1650cm-1With 700~850cm-1Region；
Sulfobutyl ether-beta-cyclodextrin is in 3430cm in Fig. 2-1There are the stretching vibration peaks of O-H at place, in 2935cm-1There are c h bonds at place
Stretching vibration peak, 1160,1143cm-1There are C-H, C-O key stretching vibrations at place；Grape seed extract and sulfobutyl ether-β-in Fig. 3
Cyclodextrin physical mixture is grape seed extract to be superimposed with sulfobutyl ether-beta-cyclodextrin, without significant changes；The Portugal Tu4Zhong
In grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, grape seed extract characteristic absorption peak disappears, and intensity obviously weakens,
1511,1441cm-1Characteristic peak disappear in inclusion compound map, and inclusion compound base table reveals the absorption peak of SBE- β-CD,
The two spectrogram is similar, this shows that grape seed extract enters in SBE- β-CD cavity, it was demonstrated that the generation of inclusion compound.
Embodiment 2
The preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, it is 20% that distilled water, which is added, and is uniformly dissolved obtained mass fraction
Sulfobutyl ether-beta-cyclodextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
The weight of grape seed extract powder is the 0.01% of sulfobutyl ether-beta-cyclodextrin weight, side edged sonic oscillation, sonic oscillation
Ultrasonic power be 250W, the frequency of sonic oscillation is 40Khz, and the temperature of sonic oscillation is 50 DEG C, to grape seed extract powder
End is placed on magnetic agitation in constant temperature blender with magnetic force after being added, and the temperature of magnetic agitation is 50 DEG C, and the time of magnetic agitation is
120min, the speed of magnetic agitation are 200r/min, obtain mixed solution after cooled to room temperature；
S3. the mixed solution that step S2 is obtained is obtained into filtrate with the filtering with microporous membrane that aperture is 0.2 μm, filtrate is put
Enter and freezed in -20 DEG C of refrigerator for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract after taking-up
Sulfobutyl ether-beta-cyclodextrin inclusion compound.
Embodiment 3
The preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, it is 20% that distilled water, which is added, and is uniformly dissolved obtained mass fraction
Sulfobutyl ether-beta-cyclodextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
The weight of grape seed extract powder is the 0.03% of sulfobutyl ether-beta-cyclodextrin weight, side edged sonic oscillation, sonic oscillation
Ultrasonic power be 250W, the frequency of sonic oscillation is 40Khz, and the temperature of sonic oscillation is 50 DEG C, to grape seed extract powder
End is placed on magnetic agitation in constant temperature blender with magnetic force after being added, and the temperature of magnetic agitation is 50 DEG C, and the time of magnetic agitation is
150min, the speed of magnetic agitation are 400r/min, obtain mixed solution after cooled to room temperature；
S3. the mixed solution that step S2 is obtained is obtained into filtrate with the filtering with microporous membrane that aperture is 0.2 μm, filtrate is put
Enter and freezed in -20 DEG C of refrigerator for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract after taking-up
Sulfobutyl ether-beta-cyclodextrin inclusion compound.
Embodiment 4
The preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, it is 20% that distilled water, which is added, and is uniformly dissolved obtained mass fraction
Sulfobutyl ether-beta-cyclodextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
The weight of grape seed extract powder is the 0.07% of sulfobutyl ether-beta-cyclodextrin weight, side edged sonic oscillation, sonic oscillation
Ultrasonic power be 250W, the frequency of sonic oscillation is 40Khz, and the temperature of sonic oscillation is 50 DEG C, to grape seed extract powder
End is placed on magnetic agitation in constant temperature blender with magnetic force after being added, and the temperature of magnetic agitation is 40 DEG C, and the time of magnetic agitation is
90min, the speed of magnetic agitation are 400r/min, obtain mixed solution after cooled to room temperature；
S3. the mixed solution that step S2 is obtained is obtained into filtrate with the filtering with microporous membrane that aperture is 0.2 μm, filtrate is put
Enter and freezed in -20 DEG C of refrigerator for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract after taking-up
Sulfobutyl ether-beta-cyclodextrin inclusion compound.
Embodiment 5
The preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, includes the following steps：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, it is 20% that distilled water, which is added, and is uniformly dissolved obtained mass fraction
Sulfobutyl ether-beta-cyclodextrin solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature,
The weight of grape seed extract powder is the 0.1% of sulfobutyl ether-beta-cyclodextrin weight, side edged sonic oscillation, sonic oscillation
Ultrasonic power be 250W, the frequency of sonic oscillation is 40Khz, and the temperature of sonic oscillation is 50 DEG C, to grape seed extract powder
End is placed on magnetic agitation in constant temperature blender with magnetic force after being added, and the temperature of magnetic agitation is 40 DEG C, and the time of magnetic agitation is
150min, the speed of magnetic agitation are 200r/min, obtain mixed solution after cooled to room temperature；
S3. the mixed solution that step S2 is obtained is obtained into filtrate with the filtering with microporous membrane that aperture is 0.2 μm, filtrate is put
Enter and freezed in -20 DEG C of refrigerator for 24 hours, freeze drier drying is immediately placed in after taking-up for 24 hours, up to grape seed extract after taking-up
Sulfobutyl ether-beta-cyclodextrin inclusion compound.
Comparative Examples 1
Sulfobutyl ether-beta-cyclodextrin replaces with beta-cyclodextrin unlike the first embodiment.
Comparative Examples 2
Unlike the first embodiment in step S1, the mass fraction of sulfobutyl ether-beta-cyclodextrin solution is 21%.
Comparative Examples 3
Unlike the first embodiment in step S1, the mass fraction of sulfobutyl ether-beta-cyclodextrin solution is 19%.
Comparative Examples 4
It does not include sonic oscillation operation unlike the first embodiment in step S1, in step S2.
Comparative example
Comparative example is the embodiment 1 of the Chinese patent application No. is CN201210146002.2.
Experimental example one：Inclusion rate test
Test method is：Weigh inclusion compound, be added in the methanol of 5 times of weight, stir evenly, under 4000r/min speed from
It the heart 20 minutes, takes supernatant to measure absorbance, inclusion compound procyanidins content is calculated with absorbance, then calculates inclusion
Rate, inclusion rate=inclusion compound procyanidins content/input amount × 100%, test result are as shown in table 1：
Table 1
As can be seen from Table 1, the inclusion rate of 1-5 of the embodiment of the present invention is higher, wherein the inclusion rate highest of embodiment 1.Ginseng
More different from embodiment 1 than the part operation of embodiment 1-4, wherein the inclusion rate of Comparative Examples 1,4 declines much, and explanation makes
Higher than the inclusion rate of beta-cyclodextrin with sulfobutyl ether-beta-cyclodextrin, sonic oscillation operation can effectively improve inclusion rate；Reference is implemented
The fall of the inclusion rate of example 2,3 is smaller than Comparative Examples 1,4, illustrates the mass fraction of sulfobutyl ether-beta-cyclodextrin solution
Inclusion rate can be reduced higher or lower than 20%.
Experimental example two：Light stability test
Test method is：Inclusion compound is weighed, is placed in oxygen-impermeable culture dish, is placed at room temperature in outdoor, natural light irradiation 6
Absorbance before testing that it, calculates absorbance rate of descent, absorbance rate of descent=(absorbance after absorbance-test before testing)/
× 100%.Test result is as shown in table 2：
Table 2
As can be seen from Table 2, it is many to be below comparative example for the absorbance rate of descent of 1-5 of the embodiment of the present invention, illustrates the present invention
The photostability of inclusion compound obtained is preferable, and wherein the photostability of embodiment 1 is best.The part operation of Comparative Examples 1-4
Different from embodiment 1, wherein the absorbance rate of descent of Comparative Examples 1 rises very much, illustrates compared with beta-cyclodextrin, sulphur fourth
Photostability of the base ether-beta-cyclodextrin than can more improve inclusion compound；The absorbance rate of descent and embodiment 1- of Comparative Examples 2-4
5 almost, illustrates that the mass fraction of sulfobutyl ether-beta-cyclodextrin solution and sonic oscillation operate the photostability to inclusion compound
Do not influence.
Experimental example three：Heat stability testing
Test method is：Inclusion compound is weighed, is placed in transparent culture dish, culture dish is placed in 80 DEG C of baking oven, 20
It is taken out after minute, calculates absorbance rate of descent, absorbance rate of descent=(absorbance after absorbance-test before testing)/test
Preceding absorbance × 100%.Test result is as shown in table 3：
| Absorbance rate of descent (%) | |
| Embodiment 1 | 10.31 |
| Embodiment 2 | 10.47 |
| Embodiment 3 | 10.39 |
| Embodiment 4 | 10.46 |
| Embodiment 5 | 10.35 |
| Comparative Examples 1 | 35.84 |
| Comparative Examples 2 | 10.48 |
| Comparative Examples 3 | 10.39 |
| Comparative Examples 4 | 10.44 |
| Comparative example | 56.93 |
Table 3
As can be seen from Table 3, it is many to be below comparative example for the absorbance rate of descent of 1-5 of the embodiment of the present invention, illustrates the present invention
The better heat stability of inclusion compound obtained, wherein the thermal stability of embodiment 1 is best.The part operation of Comparative Examples 1-4
Different from embodiment 1, wherein the absorbance rate of descent of Comparative Examples 1 rises very much, illustrates compared with beta-cyclodextrin, sulphur fourth
Thermal stability of the base ether-beta-cyclodextrin than can more improve inclusion compound；The absorbance rate of descent and embodiment 1- of Comparative Examples 2-4
5 almost, illustrates that the mass fraction of sulfobutyl ether-beta-cyclodextrin solution and sonic oscillation operate the thermal stability to inclusion compound
Do not influence.
Experimental example four：Solubility test
Test method is：Inclusion compound is weighed, is added in the water of 10 times of weight, stirring and dissolving, is centrifuged under 4000r/min speed
20 minutes, the absorbance at supernatant measurement 500nm wavelength is taken, the solubility of inclusion compound in water is calculated with absorbance, is surveyed
Test result is as shown in table 4：
| Solubility (μ g/mL) | |
| Embodiment 1 | 212.50 |
| Embodiment 2 | 212.41 |
| Embodiment 3 | 212.38 |
| Embodiment 4 | 212.45 |
| Embodiment 5 | 212.43 |
| Comparative Examples 1 | 162.66 |
| Comparative Examples 2 | 203.77 |
| Comparative Examples 3 | 204.09 |
| Comparative Examples 4 | 160.82 |
| Comparative example | 141.10 |
Table 4
As can be seen from Table 4, the solubility of 1-5 of the embodiment of the present invention is above that there are many comparative example, the wherein dissolution of embodiment 1
Spend highest.The part operation of Comparative Examples 1-4 is different from embodiment 1, and wherein the solubility of Comparative Examples 1,4 declines not
It is few, illustrate to use sulfobutyl ether-beta-cyclodextrin higher than the solubility of beta-cyclodextrin, sonic oscillation operation can effectively improve dissolution
Degree；The fall of the solubility of Comparative Examples 2,3 is smaller than Comparative Examples 1,4, illustrates sulfobutyl ether-beta-cyclodextrin solution
Mass fraction be higher or lower than and 20% can reduce solubility.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (6)
1. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound, it is characterised in that：Including following step
Suddenly：
S1. sulfobutyl ether-beta-cyclodextrin is placed in container, distilled water is added and is uniformly dissolved obtained sulfobutyl ether-beta-cyclodextrin
Solution；
S2. grape seed extract powder is added in sulfobutyl ether-beta-cyclodextrin solution made from step S1 at room temperature, Bian Jia
Side sonic oscillation is placed on magnetic agitation in constant temperature blender with magnetic force after grape seed extract powder has been added, naturally cools to
Mixed solution is obtained after room temperature；
S3. the obtained mixed solution of step S2 is obtained into filtrate with filtering with microporous membrane, put the filtrate into cold in -20 DEG C of refrigerator
Jelly is immediately placed in freeze drier drying for 24 hours for 24 hours, after taking-up, up to grape seed extract sulfobutyl ether-beta-cyclodextrin after taking-up
Inclusion compound.
2. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound according to claim 1,
It is characterized in that：In the step S1, the mass fraction of sulfobutyl ether-beta-cyclodextrin solution is 20%.
3. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound according to claim 2,
It is characterized in that：In the step S2, the weight of grape seed extract powder is the 0.01- of sulfobutyl ether-beta-cyclodextrin weight
0.1%.
4. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound according to claim 3,
It is characterized in that：In the step S2, the ultrasonic power of sonic oscillation is 250W, and the frequency of sonic oscillation is 40Khz, sonic oscillation
Temperature be 50 DEG C.
5. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound according to claim 4,
It is characterized in that：In the step S2, the temperature of magnetic agitation is 30-50 DEG C, and the time of magnetic agitation is 90-150min, magnetic force
The speed of stirring is 200-600r/min.
6. a kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound according to claim 5,
It is characterized in that：In the step S3, the aperture of miillpore filter is 0.2 μm.
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