CN104666293A - Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof - Google Patents
Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof Download PDFInfo
- Publication number
- CN104666293A CN104666293A CN201510060453.8A CN201510060453A CN104666293A CN 104666293 A CN104666293 A CN 104666293A CN 201510060453 A CN201510060453 A CN 201510060453A CN 104666293 A CN104666293 A CN 104666293A
- Authority
- CN
- China
- Prior art keywords
- cyclodextrin
- dihydromyricetin
- clathrate
- preparation
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses a dihydromyricetin cyclodextrin inclusion compound, which comprises cyclodextrin and dihydromyricetin, wherein the dihydromyricetin is embedded into a cyclodextrin cavity; and the inclusion compound employing the cyclodextrin as a host molecule and dihydromyricetin as a guest molecule is formed. The dihydromyricetin cyclodextrin inclusion compound has the beneficial effects that 1 the dihydromyricetin cyclodextrin inclusion compound is embedded by the cyclodextrin, and the solubility, the stability and the bioavailability of the dihydromyricetin are improved; 2 the preparation method of the dihydromyricetin cyclodextrin inclusion compound disclosed by the invention is simple in process and suitable for industrialized production; 3 a spray drying process is adopted, the process from spray drying to dust collection is finished within 20 seconds, the problem of product oxidation in the drying process is avoided, the method is simple in process, simple and convenient to operate; the production conditions are easy to control, and the inclusion rate of the dihydromyricetin is high; and 4 the dihydromyricetin used by the dihydromyricetin cyclodextrin inclusion compound is extracted from vitaceae ampelopsis, and the dihydromyricetin in the vitaceae ampelopsis is high in content, and is a natural substance and free of toxicity.
Description
Technical field
The invention belongs to biological medical product field, be specifically related to dihydromyricetin cyclodextrin clathrate and preparation method thereof, can be applicable to food, medicine, health products trade.
Background technology
Dihydromyricetin, it is the main chemical compositions of a kind of wild bejuco of Vitaceae Ampelopsis, this type of material has the multiple peculiar effects such as scavenging free radicals, antioxidation, antithrombotic, antitumor, antiinflammatory, also there is releasing alcoholism, prevent alcoholic liver, fatty liver, suppression hepatocyte worsens, reduce the effects such as the sickness rate of hepatocarcinoma, it is hepatoprotective, the non-defective unit of Dealcoholic sobering-up, is widely used in food, medicine, health product.At field of food, dihydromyricetin mainly adds in beverage, makes health beverage, adds in bakery product, plays antioxidation etc.; At field of medicaments, dihydromyricetin can play antibacterial, the effect such as antioxidation, adjustment blood glucose, blood fat, hepatoprotective, antitumor to have data to show, clinical application is had now to show, dihydromyricetin is widely used in treatment respiratory tract infection, crapulent Chinese patent medicine preparation, as tablet, capsule, electuary etc.; In field of health care products, dihydromyricetin is mainly developed into the health product such as instant tea, capsule, tablet Antialcoholic liver-protecting.Due to dihydromyricetin poorly water-soluble at normal temperatures, bioavailability is low, and has polyphenol hydroxyl structure, to pH value and the metal ion-sensitive such as ferrum, aluminum of light, solution, oxidizable rotten, makes it apply and is subject to larger restriction.
Cyclodextrin is the product that glucosyltransferase acts on starch, normally by 6,7 or 8 glucose molecules with α-1, the member cyclic oligosaccharides of 4-glycosidic bond link, be called α-, β or gamma-cyclodextrin, alpha-cyclodextrin is made up of 6 glucose molecules, molecular weight 972.86, dissolubility is 14.5g/100g at 25 DEG C, is applicable to some small-molecule substances of embedding; Beta-schardinger dextrin-is made up of 7 glucose molecules, molecular weight 1135, and dissolubility is 1.85g/100g at 25 DEG C, and operation strategies is wide; Gamma-cyclodextrin is made up of 8 glucose molecules, and molecular weight is 1297.12, and dissolubility is 23.2 g/100g at 25 DEG C, and water solublity is best in three, is applicable to embedding macromole or baroque material; Cyclodextrin derivative connects other group and is formed on the molecule of cyclodextrin, if HP-β-CD is a kind of hydroxyalkyl derivant of beta-schardinger dextrin-.It is not only the same with beta-schardinger dextrin-, excellent tetra-inclusion complex is had to chemical compound lot, can improve by the stability of envelope material, and water solublity is high, can improve by the rate of release of envelope medicine and bioavailability, at normal temperatures, water solublity is very high for HP-β-CD, generally all more than 50% (at room temperature, dissolubility is 750 mg/ml, and β-CD is 18 mg/ml).Cyclodextrin is a kind of molecule of relative flexibility, there is very unique space structure---molecule becomes cone column or coniform garland, there are many rotatable keys and hydroxyl, inside there is a cavity, cavity has unique enclose function, enclose conjugate be formed with permitting many kinds of substance, so cyclodextrin is as effects such as good stabilizing agent, emulsifying agent, correctives, eliminating smell agent, antioxidant, being widely used in the fields such as food, medicine, health product, cosmetics.
In order to better play the effect of dihydromyricetin, to solve, dihydromyricetin dissolved solution degree is poor, bioavailability is low, to the pH value of light, solution and the metal ion-sensitive such as ferrum, aluminum, the oxidizable shortcoming such as rotten.Adopt cyclodextrin to connect its bag, the water solublity of dihydromyricetin, stability and bioavailability can be improved, widen the utilization field of dihydromyricetin.Non-patent literature is had to disclose (beam morning mist etc., Hunan University of Traditional Chinese Medicine's journal, 2011, No1 dihydromyricetin from Ampelopsis grossedentata Benexate Hydrochloride Study on Preparation), although can be good at dihydromyricetin to embed with beta-schardinger dextrin-, but it is not high to there is dihydromyricetin Benexate Hydrochloride dissolubility in water, the shortcomings such as bioavailability is low.
Summary of the invention
The object of the invention is to: a kind of dihydromyricetin cyclodextrin clathrate and preparation method thereof is provided, dihydromyricetin is carried out bag and connects by the method, form cyclodextrin and dihydromyricetin clathrate, improve the water solublity of dihydromyricetin, to metal ion unstability and bioavailabilities such as light, oxygen, solution pH value, ferrum, aluminum.
For achieving the above object, the invention provides following technical scheme:
A clathrate for dihydromyricetin and cyclodextrin, is characterized in that, comprises cyclodextrin and is embedded in dihydromyricetin in cyclodextrin cavity, forms with cyclodextrin the clathrate be host molecule dihydromyricetin being guest molecule.
Described cyclodextrin is one or both and above combination in any thereof of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin and cyclodextrin derivative.
Described cyclodextrin derivative comprises: HP-β-CD, glucose ring dextrin, maltose cyclodextrin, dihydroxypropyl-beta-schardinger dextrin-, maltotriose cyclodextrin, methyl-B-cyclodextrin, carboxymethyl cyclodextrin, semi-annular jade pendant alkyl cyclodextrins.
As the preferred version of previous step, described cyclodextrin is gamma-cyclodextrin.
As the preferred version of previous step, described cyclodextrin derivative is HP-β-CD.
A preparation method for cyclodextrin and dihydromyricetin clathrate, is characterized in that comprising the steps:
(1), the dihydromyricetin of 100-500 part is dissolved in the solvent orange 2 A of 100-39600 part, makes dihydromyricetin cellulose solution;
(2), by the cyclodextrin of 200-600 part and/or cyclodextrin derivative directly add above-mentioned dihydromyricetin cellulose solution and/or the cyclodextrin of 200-600 part and/or cyclodextrin derivative are dissolved in the solvent B of 100-39600 part, making cyclodextrin and/or cyclodextrin derivative solution adds above-mentioned dihydromyricetin cellulose solution;
(3), with cutter sheared by mixed solution, and when having complex to be formed with microscopy, then bag has connect, and then uses spray tower spraying dry, obtains powder solid dihydromyricetin and cyclodextrin and/or cyclodextrin derivant clathrate.
As the preferred version of previous step, the system temperature in described step (1) and step (2) all remains between 60 DEG C-80 DEG C, and in step (2), the processing time is 30min-240min.
As the preferred version of previous step, in described step (3), shear rate is 3000-8000r/min, and spray tower inlet temperature is 180 DEG C-200 DEG C, leaving air temp is 70 DEG C-80 DEG C.
As the preferred version of previous step, solvent orange 2 A is one or both and above combination in any thereof of pure water, ethanol, methanol and acetone in described step (1).
As the preferred version of previous step, solvent B is one or both and above combination in any thereof of pure water, ethanol, methanol, propanol, isopropyl alcohol, ethylene glycol, propylene glycol, glycerol, acetone in described step (2).
Compared with prior art, the invention has the beneficial effects as follows:
1, use cyclodextrin bag to connect, improve the dissolubility of dihydromyricetin, stability and bioavailability.
2, dihydromyricetin cyclodextrin clathrate preparation method provided by the invention, technique is simple, is applicable to suitability for industrialized production.
3, the present invention adopts spray drying method, and completing in 20 seconds from being spray dried into collection powder, avoiding product problem of oxidation in dry run, technique is simple, easy and simple to handle, working condition is easy to control, the inclusion rate of dihydromyricetin is high.
4, dihydromyricetin used in the present invention extracts from Vitaceae ampelopsis, and in Vitaceae ampelopsis, dihydromyricetin cellulose content is high and be natural materials, avirulence.
Accompanying drawing explanation
Fig. 1 is dihydromyricetin solubility curve figure of the present invention.
Fig. 2 is the solubility curve figure of dihydromyricetin of the present invention and gamma-cyclodextrin clathrate.
Fig. 3 is the solubility curve figure of dihydromyricetin of the present invention and Benexate Hydrochloride.
Fig. 4 is the solubility curve figure of dihydromyricetin of the present invention and alpha-cyclodextrin clathrate.
Fig. 5 is dihydromyricetin of the present invention and HP-β-CD solubility curve figure.
Fig. 6 is the mean blood plasma concentration of dihydromyricetin of the present invention and clathrate and the curve chart of time.
Detailed description of the invention
Be described in more detail below in conjunction with the technical scheme of detailed description of the invention to this patent.
Embodiment 1:
A clathrate for dihydromyricetin and cyclodextrin, comprises cyclodextrin and is embedded in dihydromyricetin in cyclodextrin cavity, forms with cyclodextrin the clathrate be host molecule dihydromyricetin being guest molecule.
Described cyclodextrin is one or both and above combination in any thereof of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin and cyclodextrin derivative.
Described cyclodextrin derivative comprises: HP-β-CD, glucose ring dextrin, maltose cyclodextrin, dihydroxypropyl-beta-schardinger dextrin-, maltotriose cyclodextrin, methyl-B-cyclodextrin, carboxymethyl cyclodextrin, semi-annular jade pendant alkyl cyclodextrins.
As the preferred version of previous step, described cyclodextrin is gamma-cyclodextrin.
As the preferred version of previous step, described cyclodextrin derivative is HP-β-CD.
As the preferred version of previous step, described dihydromyricetin is the dihydromyricetin extracted from Vitaceae ampelopsis, and ampelopsis comprises Ampelopsis grossedentata, Cayratia japonica (Thunb.) Gagnep., Ampelopsis, ampelopsis cantoniensis, the beautiful Fructus Vitis viniferae of leaf, Vitis Amurensis plant, the one of Northeastern Caulis seu folium ampelopsis brevipedunculatae and Radix Ampelopsis or its several compositions.
Above-mentioned ampelopsis is commonly called as in China various places as " Ampelopsis grossedentata ", " wild Ampelopsis grossedentata ", " mountain Folium hydrangeae strigosae ", " MAOYANMEI ", " Ramulus et Folium Mussaendae Pubescentis ", " white tea cake ", " Herba Rabdosiae Lophanthoidis tea ", " manna tea ", " white hair monkey ".
Embodiment 2:
A preparation method for cyclodextrin and dihydromyricetin clathrate, is characterized in that comprising the steps:
(1), the dihydromyricetin of 100-500 part is dissolved in the solvent orange 2 A of 100-39600 part, makes dihydromyricetin cellulose solution;
(2), by the cyclodextrin of 200-600 part and/or cyclodextrin derivative directly add above-mentioned dihydromyricetin cellulose solution and/or the cyclodextrin of 200-600 part and/or cyclodextrin derivative are dissolved in the solvent B of 100-39600 part, making cyclodextrin and/or cyclodextrin derivative solution adds above-mentioned dihydromyricetin cellulose solution;
(3), with cutter sheared by mixed solution, and when having complex to be formed with microscopy, then bag has connect, and then uses spray tower spraying dry, obtains powder solid dihydromyricetin and cyclodextrin and/or cyclodextrin derivant clathrate
Embodiment 3:
(1), the dihydromyricetin that takes 100-500 part is dissolved in the pure water of 100-39600 part, and solution temperature remains on 60-80 DEG C, makes dihydromyricetin suspension;
(2), the cyclodextrin of 200-600 part or cyclodextrin derivative are slowly joined in above-mentioned dihydromyricetin suspension, carry out bag with 3000-8000r/min shearing at a high speed with cutter to connect, system temperature remains between 60-80 DEG C, processing time is 30-240min, makes dihydromyricetin inclusion complex in solution;
(3), by above-mentioned dihydromyricetin inclusion complex in solution spray tower at inlet temperature 180-200 DEG C, a leaving air temp 70-80 DEG C spraying dry obtains dihydromyricetin cyclodextrin clathrate powder.
Embodiment 4:
A, take 100-500 part dihydromyricetin and be dissolved in the ethanol of 300-600 part for subsequent use;
B, take 200-600 part cyclodextrin or cyclodextrin derivative is dissolved in the pure water of 100-39600 part, stir with 3000r/min with cutter, cyclodextrin or cyclodextrin derivative solution temperature remain on 20-80 DEG C;
C, when cyclodextrin or cyclodextrin derivative dissolve complete, the rotating speed of cutter is brought up to 5000r/min, above-mentioned dihydromyricetin alcoholic solution for subsequent use is slowly joined in cyclodextrin or cyclodextrin derivative aqueous solution in 20min, carry out shearing embedding, mixed solution temperature remains on 60-80 DEG C;
D, again the rotating speed of cutter is brought up to 8000r/min, carry out shearing 30-240min minute to system, system temperature remains on 60-80 DEG C;
E, with microscopy inspection embedding whether have complex formed and determined that bag connects degree by the state that inclusion compound exists, if having, slowly turn down the rotating speed of cutter until stop, inclusion complex in solution is reduced to room temperature, makes dihydromyricetin cyclodextrin clathrate solution; Use cutter to shear till having complex to be formed if, do not continue;
F, by above-mentioned dihydromyricetin cyclodextrin clathrate solution spray drying tower at inlet temperature 180-200 DEG C, leaving air temp 70-80 DEG C is spray-dired to dihydromyricetin cyclodextrin clathrate powder.
Embodiment 5:
For studying the solute effect of dihydromyricetin of the present invention and cyclodextrin clathrate, the dissolving situation of the present invention to dihydromyricetin and cyclodextrin clathrate has done following record:
As depicted in figs. 1 and 2, adopt thermostatic water-circulator bath pot in the water of 100ml, under different temperatures, measure the dissolubility of dihydromyricetin and dihydromyricetin gamma-cyclodextrin clathrate, obtain shown in following table:
Table 1 dihydromyricetin dissolubility
The dissolubility of table 2 dihydromyricetin gamma-cyclodextrin clathrate
As shown in Figure 3, adopt thermostatic water-circulator bath pot in the water of 100ml, under different temperatures, measure the dissolubility of dihydromyricetin and dihydromyricetin Benexate Hydrochloride, obtain shown in following table: the dissolubility of table 3 dihydromyricetin Benexate Hydrochloride
As shown in Figure 4, adopt thermostatic water-circulator bath pot in the water of 100ml, under different temperatures, measure the dissolubility of dihydromyricetin and dihydromyricetin alpha-cyclodextrin clathrate, obtain shown in following table: table 4 dihydromyricetin alpha-cyclodextrin clathrate dissolubility
As shown in Figure 5, adopt thermostatic water-circulator bath pot in the water of 100ml, under different temperatures, measure the dissolubility of dihydromyricetin and dihydromyricetin hydroxypropyl-beta-cyclodextrin inclusion, obtain shown in following table: table 5 dihydromyricetin HP-β-CD dissolubility
Dihydromyricetin as shown in table 6 compares with several clathrate dissolubility in water
The mode of gavage is adopted to allow mice on an empty stomach take in a certain amount of cyclodextrin clathrate suspension, the concentration of dihydromyricetin in blood plasma is measured respectively by high performance liquid chromatography, relatively take in the content of effective active composition in the mice plasma of dihydromyricetin and clathrate, calculate bioavailability in Mice Body.
Each time point dihydromyricetin concentration in each sample liquid of table 7
Therefrom can find in the dihydromyricetin γ-CD clathrate short time from table 7 and Fig. 6, 50-60min can reach and absorb peak in Mice Body, haemoconcentration is up to 0.311mg/l, dihydromyricetin can play maximum effect in the short time, and extract dihydromyricetin and dihydromyricetin beta-CD inclusion are when 150min, just can reach absorption maximum peak in Mice Body, haemoconcentration is up to 0.13465mg/l and 0.1539mg/l, this table illustrates that dihydromyricetin γ-CD clathrate bioavailability in Mice Body is the highest and just can play maximum effect at short notice.
Embodiment 6:
The dihydromyricetin taking 380g is dissolved in the pure water of 7600g, solution temperature remains on 80 DEG C, make dihydromyricetin suspension, the alpha-cyclodextrin of 1520g is slowly added in dihydromyricetin suspension, carry out bag under stirring with 5000r/min with cutter to connect, system temperature remains on 80 DEG C, it is 90min that bag connects the time, with spray tower with inlet temperature 180 DEG C, leaving air temp 75 DEG C carries out spraying dry, obtain finished product dihydromyricetin and alpha-cyclodextrin clathrate, it is 96.3% that the bag of dihydromyricetin connects rate.
Embodiment 7:
The dihydromyricetin taking 289g is dissolved in 95% ethanol of 2000g, make dihydromyricetin alcoholic solution, the alpha-cyclodextrin of 1010g is dissolved in 5200g aqueous solution, carry out shearing with cutter with 3000r/min to dissolve, system temperature remains on 70 DEG C, when alpha-cyclodextrin dissolves completely, the rotating speed of cutter is brought up to 5000r/min, above-mentioned dihydromyricetin alcoholic solution is slowly joined in alpha-cyclodextrin aqueous solution in 20min, carry out shearing embedding, mixed solution temperature remains on 60 DEG C, again the rotating speed of cutter is brought up to 8000r/min, shearing 120min is carried out to system, system temperature remains on 80 DEG C.Whether there is complex formed and determined that bag connects degree by the state that inclusion compound exists with microscopy inspection, if having, slowly turn down the rotating speed of cutter until stop, inclusion complex in solution is reduced to room temperature.By above-mentioned dihydromyricetin inclusion complex in solution spray drying tower inlet temperature 180 DEG C, leaving air temp 80 DEG C is spray-dired to dihydromyricetin alpha-cyclodextrin clathrate powder, and dihydromyricetin alpha-cyclodextrin inclusion rate is 94.2%.
Embodiment 8:
The dihydromyricetin taking 208g is dissolved in the pure water of 3750g, solution temperature remains on 80 DEG C, make dihydromyricetin suspension, the beta-schardinger dextrin-of 1042g is slowly added in dihydromyricetin suspension, carry out bag under stirring with 6000r/min with cutter to connect, system temperature remains on 75 DEG C, it is 90min that bag connects the time, with spray tower with inlet temperature 185 DEG C, leaving air temp 90 DEG C carries out spraying dry, obtain finished product dihydromyricetin and Benexate Hydrochloride, it is 98.25% that the bag of dihydromyricetin connects rate.
Embodiment 9:
The dihydromyricetin taking 300g is dissolved in 95% ethanol of 1500g, make dihydromyricetin alcoholic solution, the beta-schardinger dextrin-of 1200g is dissolved in 3500g aqueous solution, carry out shearing with cutter with 3000r/min to dissolve, system temperature remains on 60 DEG C, when beta-schardinger dextrin-dissolves completely, the rotating speed of cutter is brought up to 5000r/min, above-mentioned dihydromyricetin alcoholic solution is slowly joined in beta-schardinger dextrin-aqueous solution in 20min, carry out shearing embedding, mixed solution temperature remains on 70 DEG C, again the rotating speed of cutter is brought up to 8000r/min, shearing 80min is carried out to system, system temperature remains on 70 DEG C.Whether there is complex formed and determined that bag connects degree by the state that inclusion compound exists with microscopy inspection embedding, if having, slowly turn down the rotating speed of cutter until stop, inclusion complex in solution is reduced to room temperature.By above-mentioned dihydromyricetin inclusion complex in solution spray drying tower inlet temperature 180 DEG C, leaving air temp 80 DEG C is spray-dired to dihydromyricetin Benexate Hydrochloride powder, and dihydromyricetin beta-cyclodextrin inclusion compound rate is 96.2%.
Embodiment 10:
The dihydromyricetin taking 100g is dissolved in the pure water of 2400g, solution temperature remains on 80 DEG C, make dihydromyricetin suspension, the gamma-cyclodextrin of 500g is slowly added in dihydromyricetin suspension, carry out bag under stirring with 5000r/min with cutter to connect, system temperature remains on 80 DEG C, it is 60min that bag connects the time, with spray tower with inlet temperature 180 DEG C, leaving air temp 75 DEG C carries out spraying dry, obtain finished product dihydromyricetin and gamma-cyclodextrin clathrate, it is 97.6% that the bag of dihydromyricetin connects rate.
Embodiment 11:
The dihydromyricetin taking 300g is dissolved in 95% ethanol of 1800g, make dihydromyricetin alcoholic solution, the gamma-cyclodextrin of 1050g is dissolved in 2000g aqueous solution, carry out shearing with cutter with 3000r/min to dissolve, system temperature remains on 70 DEG C, when gamma-cyclodextrin dissolves completely, the rotating speed of cutter is brought up to 5000r/min, above-mentioned dihydromyricetin alcoholic solution is slowly joined in gamma-cyclodextrin aqueous solution in 20min, carry out shearing embedding, mixed solution temperature remains on 80 DEG C, again the rotating speed of cutter is brought up to 80000r/min, shearing 80min is carried out to system, system temperature remains on 80 DEG C.Whether there is complex formed and determined that bag connects degree by the state that inclusion compound exists with microscopy inspection, if having, slowly turn down the rotating speed of cutter until stop, inclusion complex in solution is reduced to room temperature.By above-mentioned dihydromyricetin inclusion complex in solution spray drying tower inlet temperature 180 DEG C, leaving air temp 70 DEG C is spray-dired to dihydromyricetin gamma-cyclodextrin clathrate powder, and dihydromyricetin gamma-cyclodextrin inclusion rate is 94.8%.
Embodiment 12:
The dihydromyricetin taking 500g is dissolved in the pure water of 7500g, solution temperature remains on 80 DEG C, make dihydromyricetin suspension, the HP-β-CD of 2000g is slowly added in dihydromyricetin suspension, carry out bag under stirring with 4500r/min with cutter to connect, system temperature remains on 80 DEG C, it is 120min that bag connects the time, with spray tower with inlet temperature 185 DEG C, leaving air temp 80 DEG C carries out spraying dry, obtain finished product dihydromyricetin and hydroxypropyl-beta-cyclodextrin inclusion, it is 96.7% that the bag of dihydromyricetin connects rate.
Embodiment 13:
The dihydromyricetin taking 400g is dissolved in 95% ethanol of 2000g, make dihydromyricetin alcoholic solution, the HP-β-CD of 1600g is dissolved in 2500g aqueous solution, carry out shearing with cutter with 3000r/min to dissolve, system temperature remains on 70 DEG C, when HP-β-CD is dissolved completely, the rotating speed of cutter is brought up to 5000r/min, above-mentioned dihydromyricetin alcoholic solution is slowly joined in gamma-cyclodextrin aqueous solution in 20min, carry out shearing embedding, mixed solution temperature remains on 80 DEG C, again the rotating speed of cutter is brought up to 8000r/min, shearing 90min is carried out to system, system temperature remains on 80 DEG C.Whether there is complex formed and determined that bag connects degree by the state that inclusion compound exists with microscopy inspection, if having, slowly turn down the rotating speed of cutter until stop, inclusion complex in solution is reduced to room temperature.By above-mentioned dihydromyricetin inclusion complex in solution spray drying tower inlet temperature 180 DEG C, leaving air temp 80 DEG C is spray-dired to dihydromyricetin hydroxypropyl-beta-cyclodextrin inclusion powder, and dihydromyricetin HP-β-CD inclusion rate is 98.4%.
Owing to adopting above-mentioned experimental program, the present invention possesses following advantage:
1, and the good water solubility all larger than the situation molecular weight of alpha-cyclodextrin, beta-schardinger dextrin-or its combination of the gamma-cyclodextrin described in the present invention, effective to the embedding of dihydromyricetin, and the bioavailability of dihydromyricetin is high, although HP-β-CD embedding dihydromyricetin water solublity is fine, but bioavailability is low, so gamma-cyclodextrin is first-selected embedded material; Use gamma-cyclodextrin bag to connect, improve the dissolubility of dihydromyricetin, stability and bioavailability.
2, dihydromyricetin and gamma-cyclodextrin are embedded in pure water, do not need to introduce other organic solvents, simplify production technology and ensure that the purity of product safety and product; Owing to not introducing other organic solvents, therefore technique does not need the correlation step of carrying out removal organic solvent again after completing, in current food and medicine strict control the overall situation of organic solvent residual under, production technology does not with an organic solvent have huge advantage undoubtedly.
3, the present invention adopts spray drying method, completing in 20 seconds, avoiding the difficult problem that product in dry run is oxidizable, making the inclusion rate of dihydromyricetin of the present invention higher from being spray dried into collection powder; Present invention process is simple, easy and simple to handle in sum, working condition is easy to control, production cost is low, meets the social desirability of low-carbon environment-friendly.
The above; be only the specific embodiment of the present invention; but protection scope of the present invention is not limited thereto; any those of ordinary skill in the art are in the technical scope disclosed by the present invention; the change can expected without creative work or replacement, all should be encompassed within protection scope of the present invention.Therefore, the protection domain that protection scope of the present invention should limit with claims is as the criterion.
To sum up, the present invention reaches above-mentioned effect.
Claims (10)
1. a clathrate for dihydromyricetin and cyclodextrin, is characterized in that, comprises cyclodextrin and is embedded in dihydromyricetin in cyclodextrin cavity, forms with cyclodextrin the clathrate be host molecule dihydromyricetin being guest molecule.
2. the clathrate of a kind of dihydromyricetin as claimed in claim 1 and cyclodextrin, is characterized in that: described cyclodextrin is one or both and above combination in any thereof of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin and cyclodextrin derivative.
3. the clathrate of a kind of dihydromyricetin as claimed in claim 2 and cyclodextrin, is characterized in that: described cyclodextrin derivative comprises: HP-β-CD, glucose ring dextrin, maltose cyclodextrin, dihydroxypropyl-beta-schardinger dextrin-, maltotriose cyclodextrin, methyl-B-cyclodextrin, carboxymethyl cyclodextrin, semi-annular jade pendant alkyl cyclodextrins.
4. the clathrate of a kind of dihydromyricetin as claimed in claim 1 or 2 and cyclodextrin, is characterized in that: described cyclodextrin is gamma-cyclodextrin.
5. the clathrate of a kind of dihydromyricetin as claimed in claim 2 or claim 3 and cyclodextrin, is characterized in that: described cyclodextrin derivative is HP-β-CD.
6. a preparation method for cyclodextrin and dihydromyricetin clathrate, is characterized in that comprising the steps:
(1), the dihydromyricetin of 100-500 part is dissolved in the solvent orange 2 A of 100-39600 part, makes dihydromyricetin cellulose solution;
(2), by the cyclodextrin of 200-600 part and/or cyclodextrin derivative directly add above-mentioned dihydromyricetin cellulose solution and/or the cyclodextrin of 200-600 part and/or cyclodextrin derivative are dissolved in the solvent B of 100-39600 part, making cyclodextrin and/or cyclodextrin derivative solution adds above-mentioned dihydromyricetin cellulose solution;
(3), with cutter sheared by mixed solution, and when having complex to be formed with microscopy, then bag has connect, and then uses spray tower spraying dry, obtains powder solid dihydromyricetin and cyclodextrin and/or cyclodextrin derivant clathrate.
7. the preparation method of a kind of cyclodextrin as claimed in claim 6 and dihydromyricetin clathrate, it is characterized in that: the system temperature in described step (1) and step (2) all remains between 60 DEG C-80 DEG C, in step (2), the processing time is 30min-240min.
8. the preparation method of a kind of cyclodextrin as claimed in claim 6 and dihydromyricetin clathrate, it is characterized in that: in described step (3), shear rate is 3000-8000r/min, and spray tower inlet temperature is 180 DEG C-200 DEG C, leaving air temp is 70 DEG C-80 DEG C.
9. the preparation method of a kind of cyclodextrin as claimed in claim 6 and dihydromyricetin clathrate, is characterized in that: solvent orange 2 A is one or both and above combination in any thereof of pure water, ethanol, methanol and acetone in described step (1).
10. the preparation method of a kind of cyclodextrin as claimed in claim 6 and dihydromyricetin clathrate, is characterized in that: solvent B is one or both and above combination in any thereof of pure water, ethanol, methanol, propanol, isopropyl alcohol, ethylene glycol, propylene glycol, glycerol, acetone in described step (2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510060453.8A CN104666293A (en) | 2015-02-05 | 2015-02-05 | Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510060453.8A CN104666293A (en) | 2015-02-05 | 2015-02-05 | Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104666293A true CN104666293A (en) | 2015-06-03 |
Family
ID=53302235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510060453.8A Pending CN104666293A (en) | 2015-02-05 | 2015-02-05 | Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104666293A (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105733902A (en) * | 2016-04-25 | 2016-07-06 | 浙江农林大学 | Preparation method of chimonanthus salicifolius and kudzuvine root yellow wine for dispelling effects of alcohol |
| CN106667794A (en) * | 2017-01-25 | 2017-05-17 | 西安科艺诗生物技术有限公司 | Inclusion compound for improving photostability of chromoprotein and application of inclusion compound |
| CN108653014A (en) * | 2018-06-28 | 2018-10-16 | 广东工业大学 | A kind of whitening patch-lightening cosmetic and preparation method thereof |
| CN109180629A (en) * | 2018-10-12 | 2019-01-11 | 浙江省林业科学研究院 | A kind of green extraction method improving dihydromyricetin yield |
| JP2019033684A (en) * | 2017-08-15 | 2019-03-07 | 株式会社ファンケル | Ampelopsin-stabilized food and drink composition |
| CN109527571A (en) * | 2018-12-10 | 2019-03-29 | 张家界茅岩莓有限公司 | A kind of dihydromyricetin resists liquor-saturated preparation and preparation method thereof |
| CN110787299A (en) * | 2019-11-06 | 2020-02-14 | 王京杭 | Composition and preparation method thereof |
| CN111096442A (en) * | 2020-01-16 | 2020-05-05 | 河南科技学院 | Preparation method of emulsion gel based on dihydromyricetin/amylose complex |
| CN111543636A (en) * | 2020-06-03 | 2020-08-18 | 王京杭 | Flavone high-fiber composition and preparation method thereof |
| CN112353793A (en) * | 2020-11-13 | 2021-02-12 | 福建卫生职业技术学院 | Ampelopsin oral preparation with high bioavailability |
| CN112715939A (en) * | 2020-12-30 | 2021-04-30 | 杭州娃哈哈科技有限公司 | Preparation method of dihydromyricetin compound solution capable of being stably stored for long time |
| WO2021126078A1 (en) * | 2019-12-16 | 2021-06-24 | Hoow Foods Pte. Ltd. | Formulation, composition or foodstuff additives for the modification of glycemic response methods of manufacturing and using the same |
| CN113155882A (en) * | 2021-03-15 | 2021-07-23 | 宁波大学 | Chiral identification method for enantiomer of dihydromyricetin |
| CN113817190A (en) * | 2021-10-13 | 2021-12-21 | 四川大学 | Degradable double-layer polysaccharide active membrane and preparation method thereof |
| CN114028584A (en) * | 2021-11-18 | 2022-02-11 | 辽宁万嘉医药科技有限公司 | Polyphenol multi-element cyclodextrin inclusion compound for reducing uric acid and preparation method thereof |
| US20220062223A1 (en) * | 2018-11-14 | 2022-03-03 | The Trustees Of Princeton University | Dihydromyricetin spray-dried dispension formulations and methods for forming them |
| CN116036034A (en) * | 2023-03-31 | 2023-05-02 | 北京佳福瑞生物科技有限公司 | Composite medicament for treating neuropsychiatric diseases and preparation method thereof |
-
2015
- 2015-02-05 CN CN201510060453.8A patent/CN104666293A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| JIGUO YANG,ET AL.: "Apoptosis induced by the inclusion complex of dihydromyricetin with hydroxypropyl-β-cyclodextrin in Human Hep G2 cells", 《JOURNAL OF MEDICINAL PLANTS RECEARCH》 * |
| 粱晓岚等: "藤茶中二氢杨梅素β-环糊精包合物制备工艺研究", 《湖南中医药大学学报》 * |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105733902A (en) * | 2016-04-25 | 2016-07-06 | 浙江农林大学 | Preparation method of chimonanthus salicifolius and kudzuvine root yellow wine for dispelling effects of alcohol |
| CN105733902B (en) * | 2016-04-25 | 2018-08-28 | 浙江农林大学 | A kind of preparation method for the type Liu Yazi pueraria lobata yellow rice wine that relieves the effect of alcohol |
| CN106667794A (en) * | 2017-01-25 | 2017-05-17 | 西安科艺诗生物技术有限公司 | Inclusion compound for improving photostability of chromoprotein and application of inclusion compound |
| JP2019033684A (en) * | 2017-08-15 | 2019-03-07 | 株式会社ファンケル | Ampelopsin-stabilized food and drink composition |
| CN108653014A (en) * | 2018-06-28 | 2018-10-16 | 广东工业大学 | A kind of whitening patch-lightening cosmetic and preparation method thereof |
| CN109180629A (en) * | 2018-10-12 | 2019-01-11 | 浙江省林业科学研究院 | A kind of green extraction method improving dihydromyricetin yield |
| US20220062223A1 (en) * | 2018-11-14 | 2022-03-03 | The Trustees Of Princeton University | Dihydromyricetin spray-dried dispension formulations and methods for forming them |
| CN109527571A (en) * | 2018-12-10 | 2019-03-29 | 张家界茅岩莓有限公司 | A kind of dihydromyricetin resists liquor-saturated preparation and preparation method thereof |
| CN110787299A (en) * | 2019-11-06 | 2020-02-14 | 王京杭 | Composition and preparation method thereof |
| CN115038340A (en) * | 2019-12-16 | 2022-09-09 | 昊福食品私人有限公司 | Preparation, composition or food additive for changing blood sugar reaction, and its preparation method and application |
| WO2021126078A1 (en) * | 2019-12-16 | 2021-06-24 | Hoow Foods Pte. Ltd. | Formulation, composition or foodstuff additives for the modification of glycemic response methods of manufacturing and using the same |
| CN111096442A (en) * | 2020-01-16 | 2020-05-05 | 河南科技学院 | Preparation method of emulsion gel based on dihydromyricetin/amylose complex |
| CN111096442B (en) * | 2020-01-16 | 2022-06-17 | 河南科技学院 | Preparation method of emulsion gel based on dihydromyricetin/amylose complex |
| CN111543636A (en) * | 2020-06-03 | 2020-08-18 | 王京杭 | Flavone high-fiber composition and preparation method thereof |
| CN112353793A (en) * | 2020-11-13 | 2021-02-12 | 福建卫生职业技术学院 | Ampelopsin oral preparation with high bioavailability |
| CN112715939A (en) * | 2020-12-30 | 2021-04-30 | 杭州娃哈哈科技有限公司 | Preparation method of dihydromyricetin compound solution capable of being stably stored for long time |
| CN112715939B (en) * | 2020-12-30 | 2023-03-10 | 杭州娃哈哈科技有限公司 | Preparation method of dihydromyricetin compound solution capable of being stably stored for long time |
| CN113155882A (en) * | 2021-03-15 | 2021-07-23 | 宁波大学 | Chiral identification method for enantiomer of dihydromyricetin |
| CN113817190A (en) * | 2021-10-13 | 2021-12-21 | 四川大学 | Degradable double-layer polysaccharide active membrane and preparation method thereof |
| CN113817190B (en) * | 2021-10-13 | 2022-05-20 | 四川大学 | Degradable double-layer polysaccharide active membrane and preparation method thereof |
| CN114028584A (en) * | 2021-11-18 | 2022-02-11 | 辽宁万嘉医药科技有限公司 | Polyphenol multi-element cyclodextrin inclusion compound for reducing uric acid and preparation method thereof |
| CN114028584B (en) * | 2021-11-18 | 2023-09-05 | 辽宁万嘉医药科技有限公司 | Uric acid-reducing polyphenol-containing multi-cyclodextrin inclusion compound and preparation method thereof |
| CN116036034A (en) * | 2023-03-31 | 2023-05-02 | 北京佳福瑞生物科技有限公司 | Composite medicament for treating neuropsychiatric diseases and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104666293A (en) | Dihydromyricetin cyclodextrin inclusion compound and preparation method thereof | |
| dos Santos et al. | Novel trends in cyclodextrins encapsulation. Applications in food science | |
| Feng et al. | Structural characterization and bioavailability of ternary nanoparticles consisting of amylose, α-linoleic acid and β-lactoglobulin complexed with naringin | |
| Semalty | Cyclodextrin and phospholipid complexation in solubility and dissolution enhancement: a critical and meta-analysis | |
| Nguyen et al. | Facile preparation of water soluble curcuminoids extracted from turmeric (Curcuma longa L.) powder by using steviol glucosides | |
| Celebioglu et al. | Encapsulation and stabilization of α-lipoic acid in cyclodextrin inclusion complex electrospun nanofibers: Antioxidant and fast-dissolving α-lipoic acid/cyclodextrin nanofibrous webs | |
| CN103476432A (en) | Process for producing aqueous solution containing fat-soluble substance | |
| JP6421280B1 (en) | Method for producing flavonoid inclusion compound | |
| JP5087086B2 (en) | Drug composition containing inclusion body of cyclodextrin / paclitaxel and method for producing the same | |
| Karim et al. | Suppression of palmitic acid-induced hepatic oxidative injury by neohesperidin-loaded pectin-chitosan decorated nanoliposomes | |
| Zu et al. | The high water solubility of inclusion complex of taxifolin-γ-CD prepared and characterized by the emulsion solvent evaporation and the freeze drying combination method | |
| Nicoletti et al. | An improved method for the preparation of β-lapachone: 2-hydroxypropyl-β-cyclodextrin inclusion complexes | |
| CN101485626B (en) | Aqueous solution containing coenzyme Q10 nano granule and preparation method thereof | |
| US20220023771A1 (en) | Extraction method and composition obtained therefrom | |
| CN102920762A (en) | High-absorptivity ginseng powder and preparation method thereof | |
| Braga et al. | Getting under the skin: Cyclodextrin inclusion for the controlled delivery of active substances to the dermis | |
| CN101574525A (en) | Hydroxypropyl-beta-cyclodextrin inclusion compound for lipophilic medicaments, and preparation method thereof | |
| TW201433576A (en) | Essential oil cyclodextrin composite | |
| CN112516331B (en) | Method for improving water solubility and bioavailability of hesperidin | |
| JP2006111534A (en) | Manufacturing method for curcumin aqueous solution | |
| US20050085444A1 (en) | Cosmetic or dermatological use of vitamin a or the esters thereof in combination with a partly methylated beta-cyclodextrin | |
| CN106421811A (en) | Sea-buckthorn oil and cyclodextrin clathrate | |
| FI114917B (en) | Lignaanikomplekseja | |
| Kashapov et al. | Solubility and biological activity enhancement of the highly lipophilic viridicatins via interaction with cyclodextrins | |
| CN114128914B (en) | Clathrate compound, preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150603 |