CN102796070A - Preparation method of oligomeric proanthocyanidins - Google Patents
Preparation method of oligomeric proanthocyanidins Download PDFInfo
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Abstract
The invention discloses a preparation method of oligomeric proanthocyanidins. The preparation method comprises the following steps of: adding tea polyphenols to a procyanidine plant raw material or an extract thereof; dissolving the procyanidine plant raw material or the extract into an acid aqueous solution according to percentage concentration by weight; carrying out reaction on a mixture for 0.5-5 h at 40-100 G C; adsorbing the solution after reaction by an adsorbing resin; washing the solution after reaction by a distilled water to remove impurities; eluting the solution after reaction by ethanol water; and concentrating and drying the solution after reaction so as to obtain the oligomeric proanthocyanidins. The preparation method of the oligomeric proanthocyanidins, disclosed by the invention, has the advantages of high oligomeric proanthocyanidin content, low average degree of polymerizatoin, high water solubility, high recovery rate, environment friendliness, high efficiency, simplicity and convenience in operation and low cost, can be applied to the fields, such as foods, healthcare foods, drugs, cosmetics, daily chemicals, animal feeds and the like, and is suitable for large-scale industrial production.
Description
Technical field
The invention belongs to chemical industry chemical prepn process field, be specifically related to a kind of preparation method of anioxidant phytochemicals, relate in particular to a kind of preparation method of oligomeric procyanidolics.
Background technology
Pycnogenols is the general name of one big type of Polyphenols polymkeric substance in the plant, passes through C by the flavane 3-of different numbers is pure like unit such as catechin, l-Epicatechols
4-C
8Or C
4-C
6Be polymerized etc. different bonding modes, extensively be present in the plants such as pine tree, grape, also be present in many beverages, vegetables, fruit and the grain, closely related with the mankind's daily life.Size according to the polymerization degree is called oligomeric procyanidolics with two～tetramer usually, pentamer and the above poly pycnogenols that is called.
Research shows, the polymerization degree is bigger to the biological activity influence such as anti-oxidant of pycnogenols, along with its antioxygenation of increase of the polymerization degree significantly reduces.Compare with the poly pycnogenols; Oligomeric procyanidolics anti-oxidant, remove radical, prevent and treat cardiovascular disorder, significant biological activity arranged aspect anticancer, anti-ageing the waiting for a long time; Wherein active best with procyanidin dimers; Can prevent the multiple disease that causes because of radical, and be celebrated with efficient, low toxicity, high bioavailability.In recent years, oligomeric procyanidolics as a kind of natural powerful inhibitor in Europe, nutrition, health care, the medicine and other fields of country such as U.S.A, day be used widely, and enjoy " skin VITAMINs " and good reputations such as " oral makeup ".
The poly pycnogenols is because molecular weight is bigger, water-soluble relatively poor, and utilization is difficult to be absorbed by the body; And because sterically hindered influence; The activity of phenolic hydroxyl group is affected, and therefore major part goes out of use at present, only has small portion to utilize as low value-added sub products such as natural pigments.Yet the pycnogenols in the plant mainly exists with polymeric form, is 9～10 like the mean polymerisation degree of Cortex Pini pycnogenols, and the poly pycnogenols accounts for about 50% in Semen Vitis viniferae extract and the LPC, and the poly pycnogenols in the pawpaw polyphenol accounts for 90%.In fact some pycnogenols products that at home and abroad sell well on the market at present remain the procyanidin extract that contains most of polymer, exist bioavailability low, influence deficiencies such as quality product and effect.Therefore, in order to improve the plant resources utilization rate and the added value of product of pycnogenols effectively, be necessary the poly pycnogenols is degraded to oligomeric procyanidolics.
Big quantity research report about pycnogenols is conceived to itself inherent biological activity more so far, as in healthcare products, medicine, food, makeup, having obtained many-sided application as inhibitor.But, the chemical degradation through the poly pycnogenols is obtained oligopolymer rarely has report with the research that strengthens its physiologically active.In recent years; The foreign scholar finds that some amino acid such as halfcystine, oligopeptides such as gsh (international application for a patent for invention PCT/JP2004/007448), Phloroglucinol ring or Resorcinol ring structure class material (international application for a patent for invention PCT/JP2006/303402) etc. are applied in the degraded of Semen Vitis viniferae, Cortex Pini, lichee poly pycnogenols, finds that degraded product has physiologically actives such as good anti-oxidant, antitumor, immunomodulatory and neuroprotective.Application number is that 200410016355.6 Chinese invention patent has been reported the ydrogen peroxide 50 that adopts 20-60% or Potcrate as the degraded oxygenant, and oxygenated vegetable tannin extract poly pycnogenols obtains the operational path of oligomer product under neutrallty condition; The patent No. is that the Chinese invention patent of ZL200710067047.X has been reported the method for preparing the Semen Vitis viniferae oligomeric procyanidolics under heating, acidity and the secluding air condition; Application number is that 200810034736.5 and 200910050368.8 Chinese invention patent has reported that respectively Chinese cassia tree and gold buckwheat raw anthocyanin superpolymer catalytic hydrogenolysis are the preparation method of oligopolymer.Application number is that 201110438076.9 Chinese invention patent has been reported the method that adopts sulphite or bisulfite salt brine solution heating condition to prepare the Semen Vitis viniferae oligomeric procyanidolics down.Above-mentioned these methods are owing to have: or in reaction system, use methyl alcohol; Or the reaction times is long; Or the use catalytic amount is excessive and unstable or need secluding air or high-tension apparatus to cause operation inconvenience; And the product that obtains need carry out defectives such as safety evaluation again, still is confined to the laboratory study operational phase so far, is difficult to carry out Industry Promotion and uses.Up to the present do not have as yet and adopt the tea-polyphenol in food source to carry out the report that the pycnogenols oligomer prepares.
Summary of the invention
To the above-mentioned deficiency that prior art exists, the object of the invention is intended to provide that a kind of technology is simple, the preparation method of safety and the high plant oligomeric procyanidolics of the recovery.
Above-mentioned purpose of the present invention is to realize through following technical scheme:
A kind of preparation method of oligomeric procyanidolics comprises the steps:
(a) with pycnogenols plant material or its extract; With and the tea-polyphenol of 5～100% raw material consumptions to be dissolved in weight percent concentration be in 1～20% the aqueous acid; Be mixed with the mixed solution that concentration is 10～200g/L, under 40～100 ℃ of conditions, reacted 0.5～5 hour.
(b) reacted solution is adsorbed with polymeric adsorbent in the step (a), through the distilled water wash impurity elimination, use concentration of volume percent to be 30～80% aqueous ethanolic solution wash-outs then after, elutriant promptly gets oligomeric procyanidolics behind concentrate drying.
Described plant pycnogenols raw material can be the commercially available prod, also can from Cortex Pini, pine needle, Semen Vitis viniferae skin, apple, pawpaw, lichee, hops, longan, sea-buckthorn, phyllanthus emblica, cassia bark, Chinese sorghum, buckwheat, persimmon, mangosteen, banana, bajiao banana, hawthorn, loquat, Chinese chestnut, cherry, pomegranate, sweet potato, cowberry, the seedpod of the lotus, Kiwifruit, red bayberry, fibert, silk tree, ginkgo, walnut, Queensland nut, garden burnet, cotton, herbage, jujube tree, cocoa tree, Anlnus nepalensis tree, water wax gourd tree, cypress, Bruguiera conjugata tree, Schima superba, birch, eucalyptus, willow, camphor tree, chestnut, robur, black wattle plant etc., prepare respectively according to the pycnogenols preparation method of routine.
Described tea-polyphenol can be the commercially available prod, also can from cultivation leaflet kind tealeaves or large leaf tealeaves or wild tea tree tealeaves, prepare according to the Preparing Tea-polyphenol method of routine.
Described aqueous acid; Wherein use at least a kind in hydrochloric acid, Hydrocerol A, acetic acid, xitix, oxysuccinic acid, tartrate, gallic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, the sulfurous acid, preferably at least a kind in hydrochloric acid, Hydrocerol A, acetic acid, the xitix.
Further; In the aftertreatment, described polymeric adsorbent is a kind of in vinylbenzene-Vinylstyrene class polymeric adsorbent, ion exchange resin, methacrylic polymeric adsorbent, hydrophilic ethylene base resin, polydextran gel, modification Expex gel, polyacrylamide gel or the reverse phase silica gel.
Further, in the aftertreatment, it is 40～70% aqueous ethanolic solution that described wash-out preferably uses concentration of volume percent.
Further, in the aftertreatment, said dry at least a kind of adopting in vacuum or freezing or the spraying drying mode.
The preparation method of described oligomeric procyanidolics; Preferred scheme is: the consumption of tea-polyphenol is 50～100% pycnogenols plant material or its extract consumption; The aqueous acid weight percent concentration is 1～5%; Mixed liquid concentration is mixed with 20～100g/L, under 70～90 ℃ of conditions, reacts 0.5～2 hour; It is 40～70% that the aqueous ethanolic solution wash-out uses concentration of volume percent.
Compared with prior art, beneficial effect of the present invention is following:
1, in DeR, with an organic solvent and at short notice do not realize effective degraded of plant poly pycnogenols, have environmental protection, efficient, easy and simple to handle, advantage that cost is low, suitablely carry out large-scale industrial production.
2, the tea-polyphenol that uses the food source is as poly pycnogenols degradation agents, and the gained oligomeric procyanidolics need not to carry out safety evaluation, can directly be applied.
3, the water-soluble height of gained oligomeric procyanidolics, the polymerization degree are low, have the anti-oxidant activity better than natural procyanidins, can be used as free-radical scavengers and are widely used in food, healthcare products, medicine, makeup, daily chemicals and the animal-feed etc.
Embodiment:
Below further specify essentiality content of the present invention through enumerating embodiments of the invention, but do not limit the present invention with this.
Embodiment 1:
Get commercially available Cortex Pini Massonianae extract 10g, it is in 1% the aqueous hydrochloric acid, to be mixed with the mixed solution that concentration is 20g/L that tea-polyphenol 10g is dissolved in the 1000ml weight percent concentration, 70 ℃ of reactions 1 hour down.After reaction finished, reaction soln was cooled to room temperature, adsorbs with Diaion HP-20 macroporous adsorption resin chromatography post; Earlier with the impurity elimination of 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 50% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the vacuum-drying of collecting, gets Cortex Pini oligomeric procyanidolics 19.0g; Yield is 95.0%, and mean polymerisation degree is 2.75.
Embodiment 2:
Get commercially available Cortex Pini Massonianae extract 10g, it is in 2% the aqueous hydrochloric acid, to be mixed with the mixed solution that concentration is 50g/L that tea-polyphenol 5g is dissolved in the 300ml weight percent concentration, 80 ℃ of reactions 1 hour down.After reaction finished, reaction soln was cooled to room temperature, adsorbs with Diaion HP-20 macroporous adsorption resin chromatography post; Earlier with the impurity elimination of 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 70% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the vacuum-drying of collecting, gets Cortex Pini oligomeric procyanidolics 13.5g; Yield is 90%, and mean polymerisation degree is 2.95.
Embodiment 3:
Get commercially available grape seed polyphenols 10g, the weight percent concentration that tea-polyphenol 10g is dissolved in 250ml is in 2% the aqueous hydrochloric acid, to be mixed with the mixed solution that concentration is 80g/L, 90 ℃ of reactions 0.5 hour.After reaction finished, reaction soln was cooled to room temperature, last sephadex lh-20 chromatography column; Earlier with the impurity elimination of 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 70% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the lyophilize of collecting, gets Semen Vitis viniferae oligomeric procyanidolics 18.5g; Yield is 92.5%, and mean polymerisation degree is 2.80.
Embodiment 4:
Get commercially available grape seed polyphenols 10g, the weight percent concentration that tea-polyphenol 5g is dissolved in 250ml is in 2% the aqueous citric acid solution, to be mixed with the mixed solution that concentration is 60g/L,, 70 ℃ of reactions 1 hour down.After reaction finished, reaction soln was cooled to room temperature, last AB-8 polymeric adsorbent chromatography column; Earlier with the impurity elimination of 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 80% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the lyophilize of collecting, gets Semen Vitis viniferae oligomeric procyanidolics 13.2g; Yield is 88%, and mean polymerisation degree is 2.70.
Embodiment 5:
Take from system pawpaw polyphenol extract 10g, the weight percent concentration that tea-polyphenol 10g is dissolved in 200ml is in 3% the aqueous hydrochloric acid, to be mixed with the mixed solution that polyphenol concentration is 100g/L, 70 ℃ of reactions 2 hours down.After reaction finished, reaction soln was cooled to room temperature, last Diaion HP-20 macroporous adsorption resin chromatography post; Earlier with the impurity elimination of 2 column volume distilled water washs; Use the aqueous ethanolic solution wash-out of the volumetric concentration 50% of 3 column volumes then,, get pawpaw oligomeric procyanidolics 18g elutriant concentrating under reduced pressure, the lyophilize of collecting; Yield is 87.5%, and mean polymerisation degree is 2.73.
Embodiment 6:
Take from system pawpaw polyphenol extract 10g, the weight percent concentration that tea-polyphenol 5g is dissolved in 250ml is in 5% the aqueous citric acid solution, to be mixed with the mixed solution that concentration is 65g/L, 70 ℃ of reactions 0.5 hour down.After reaction finished, reaction soln was cooled to room temperature, last Amberlite XAD polymeric adsorbent chromatography column; Earlier with 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 40% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the vacuum-drying of collecting, gets pawpaw oligomeric procyanidolics 13.6g; Yield is 90.7%, and mean polymerisation degree is 2.85.
Embodiment 7:
Get commercially available LPC 10g, the weight percent concentration that tea-polyphenol 10g is dissolved in 250ml is in 3% the aqueous hydrochloric acid, to be mixed with the mixed solution that concentration is 80g/L, 70 ℃ of reactions 0.5 hour down.After reaction finished, reaction soln was cooled to room temperature, last Diaion HP-20 macroporous adsorption resin chromatography post; Earlier with 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 50% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the lyophilize of collecting, gets apple oligomeric procyanidolics 17.6g; Yield is 88%, and mean polymerisation degree is 2.85.
Embodiment 8:
Get commercially available LPC 10g, the weight percent concentration that tea-polyphenol 5g is dissolved in 200ml is in 3% the aqueous citric acid solution, to be mixed with the mixed solution that concentration is 75g/L, 80 ℃ of reactions 1 hour down.After reaction finished, reaction soln was cooled to room temperature, last AB-8 polymeric adsorbent chromatography column; Earlier with 2 column volume distilled water washs; The volumetric concentration of using 3 column volumes then is 60% aqueous ethanolic solution wash-out, with elutriant concentrating under reduced pressure, the vacuum-drying of collecting, gets apple oligomeric procyanidolics 13.5g; Yield is 90%, and mean polymerisation degree is 2.75.
Claims (7)
1. the preparation method of an oligomeric procyanidolics comprises the steps:
(a) with pycnogenols plant material or its extract; And the tea-polyphenol of 5～100% pycnogenols plant material or its extract consumption to be dissolved in weight percent concentration be in 1～20% the aqueous acid; Be mixed with the mixed solution that concentration is 10～200g/L, under 40～100 ℃ of conditions, reacted 0.5～5 hour;
(b) step (a) reacted solution is adsorbed with polymeric adsorbent, and through the distilled water wash impurity elimination, using concentration of volume percent then is 30～80% aqueous ethanolic solution wash-out, the gained elutriant behind concentrate drying, oligomeric procyanidolics.
2. the preparation method of oligomeric procyanidolics according to claim 1; It is characterized in that described pycnogenols plant material is at least a kind in pine tree, grape, apple, pawpaw, lichee, hops, longan, sea-buckthorn, phyllanthus emblica, cassia bark, Chinese sorghum, buckwheat, persimmon, mangosteen, banana, bajiao banana, hawthorn, loquat, cherry, pomegranate, sweet potato, cowberry, the seedpod of the lotus, Kiwifruit, red bayberry, fibert, silk tree, ginkgo, walnut, Queensland nut, garden burnet, cotton, herbage, jujube tree, cocoa tree, Anlnus nepalensis tree, water wax gourd tree, cypress, Bruguiera conjugata tree, Schima superba, birch, eucalyptus, willow, camphor tree, chestnut, robur, the black wattle plant.
3. the preparation method of oligomeric procyanidolics according to claim 1, it is characterized in that: described tea-polyphenol is the commercially available prod, or by the preparation and getting from cultivation leaflet kind tealeaves or large leaf tealeaves or wild tea tree tealeaves of the Preparing Tea-polyphenol method of routine.
4. the preparation method of oligomeric procyanidolics according to claim 1, it is characterized in that: the acid of described aqueous acid is at least a kind in hydrochloric acid, Hydrocerol A, acetic acid, xitix, oxysuccinic acid, tartrate, gallic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, the sulfurous acid.
5. the preparation method of oligomeric procyanidolics according to claim 1 is characterized in that: described polymeric adsorbent is at least a in vinylbenzene-Vinylstyrene class polymeric adsorbent, ion exchange resin, methacrylic polymeric adsorbent, hydrophilic ethylene base resin, polydextran gel, modification Expex gel, polyacrylamide gel or the reverse phase silica gel.
6. the preparation method of oligomeric procyanidolics according to claim 1 is characterized in that: the said dry freezing or spray-dired mode of vacuum that adopts.
7. the preparation method of oligomeric procyanidolics according to claim 1; It is characterized in that: the consumption of said tea-polyphenol is 50～100% pycnogenols plant material or its extract consumption; The aqueous acid weight percent concentration is 1～5%; Mixed liquid concentration is mixed with 20～100g/L, under 70～90 ℃ of conditions, reacts 0.5～2 hour; It is 40～70% that said aqueous ethanolic solution wash-out uses concentration of volume percent.
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| CN104803960A (en) * | 2015-02-27 | 2015-07-29 | 云南民族大学 | Method for extracting and separating procyanidine of hawthorn fruit through low-temperature aqueous two phase cooling |
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