CN110372770A - The highly effective extraction method of natural hydroxyl or/and carboxyl compound - Google Patents

The highly effective extraction method of natural hydroxyl or/and carboxyl compound Download PDF

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CN110372770A
CN110372770A CN201810388778.2A CN201810388778A CN110372770A CN 110372770 A CN110372770 A CN 110372770A CN 201810388778 A CN201810388778 A CN 201810388778A CN 110372770 A CN110372770 A CN 110372770A
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aqueous solution
active aglycone
aglycone
fatty acid
active
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耿兆翔
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Abstract

The highly effective extraction method of natural hydroxyl or/and carboxyl compound, is related to technical field of bioengineering, step: triterpenoid saponin/flavonoid glycoside/resveratrol glucoside acidic aqueous solution beta-glucosidase enzyme hydrolysis, with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize above-mentioned hydrolysis aqueous solution, under the action of the sour rouge of oleic acid or/and palmitinic acid with saturated aqueous solution salting-out separation triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone of sodium chloride or potassium chloride Nacl/Kcl and the conjugate of the sour rouge of palmitinic acid, separate triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone.The separation and Extraction of active aglycone/resveratrol glucoside active aglycone for natural triterpenoid saponin active aglycone/flavonoid glycoside.

Description

The highly effective extraction method of natural hydroxyl or/and carboxyl compound
Technical field:
The present invention relates to the extracting method of a kind of natural hydroxyl of technical field of bioengineering or/and carboxyl compound, The highly effective extraction method of especially natural hydroxyl or/and carboxyl compound.
Background technique:
With the improvement of people ' s living standards and to the nontoxic of natural plant source, be safely and efficiently conducive to protect People's health, the pursuit for natural organic substance of preventing and curing diseases are protected, biotherapy has become artificial synthesized Western medicine and treats Method can not neglect the necessary auxiliary and substitution lacked.
Simultaneously as some traditional artificial synthetic pesticides, biological residual quantity is high, seriously endangers people's health, is not easy Degradation, has biggish toxicity to water environment and biology, therefore, the natural biological pesticide in natural plant source is just becoming green agriculture The pursuit of industry.
But these natural hydroxyls or/and carboxyl compound are simple and efficient, quickly, environmentally safe separation and Extraction skill Art is always global problem.Common method has heavy metallic salt precipitation and separation sour reduction method again, organic solvent extractionprocess, macropore Resin adsorption method and membrane separation process.Organic solvent extraction, macroporous resin adsorption and membrane separation plant investment are big, and production efficiency is low, High production cost, product active constituent content is low, or even only 30% or so, and pharmaceutical value is low, it is difficult to extensive industry metaplasia It produces.And sour reduction method will be inevitably generated the heavy metallic salt and strong acid or strong acid salt of highly-water-soluble to heavy metallic salt precipitating again Produce waste water, the destruction for thering is very big sum to be difficult to eliminate water environment.
The use of heavy metallic salt is very sensitive, concerning people's health and water environment significant problem.And it is difficult to It removes to the safety value to human and environment hereinafter, heavy metallic salt is very low to the safety value of human and environment, the prior art is difficult thoroughly Heavy metallic salt is removed from waste water, and processing cost is high.So the heavy metallic salt precipitation method extract natural hydroxyl or/and carboxyl Compound does not consider the Laboratory Production technology poisoned to human and environment only, is that the extensive treatment after pollution of one kind can not " empty talk " production technology of large-scale production.
Natural flavone glycoside and resveratrol glycoside compound, bioactivity are (i.e. active by aglycone therein Aglycon) it determines rather than is determined by glucosides itself, because the active group on the active aglycone (non-saccharide body) in glucosides is by glucosides Key destroys.Although its chemical property of glucosides is more stable in natural plants, bioactivity has been lost；Aglycone biology is living Property is strong but unstable；Property is stable and bioactivity can not get both.So the aglycone to dissociate in natural plants is seldom shown in, Mostly exist with its corresponding glycoside forms.Existing Industrialized processing technique is all to extract flavonoid glycoside (such as soybean isoflavone glycoside from soybean isoflavones, white Veratryl alcohol glycosides), rather than active aglycone therein (aglycone, e.g., real isoflavones and resveratrol).
And Chinese patent, October 25 2012 applying date, patent No. ZL201210436957.1 (or in which state's priority File application number 201110334789.0,2011.10.28CN) " the extraction side of natural hydroxyl or/and carboxyl compound Method ", due to all containing the palmitinic acid of the high degree of dispersion of a large amount of water-insoluble or/and the sour rouge of oleic acid in natural plants, and The mass content of the sour rouge of palmitinic acid or/and oleic acid is to extract the active glycosides of product triterpenoid saponin active aglycone/flavonoid glycoside 10-100 times or more of member/resveratrol glucoside active aglycone；So the cationic surfactant of the patented method with Sodium salt/sylvite subdivision of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Solution reaction has certain difficulty, because the sour rouge of the palmitinic acid of the high degree of dispersion of water-insoluble or/and oleic acid is anti-to this double decomposition There should be biggish barrier action.There is larger impact to reaction efficiency and product yield.It is necessary to break through and innovate again.
Summary of the invention:
The so-called natural hydroxyl of the present invention or/and carboxyl compound are primarily referred to as natural acidic triterpene saponin (containing carboxylic Base-COOH or hydroxyl-OH) compound, natural flavone glycoside (hydroxyl-OH, including flavonoids glycosides and isoflavone aglycone), white black false hellebore Alcohol glycoside compound (hydroxyl-OH), but do not include anthocyanidin active aglycone.
According to existing knowledge, the natural glucosides of the overwhelming majority is D-Glucose glycosides and nearly all natural glucosides is all β type sugar Glycosides；According to enzyme degradation substrate specificity, almost all of beta-glucosidase (abbreviation BGL, also known as β-D-Glucose glycosides hydrolysis Enzyme) it is poor to the specificity of the glycosyl part structure of substrate, C-O glycosidic bond, C-S key, C-N key, C-F key etc. can be cracked, also can Beta-glucosidase key and beta galactose glycosidic bond and xylose glycosidic bond, cellobiose glycosidic bond are hydrolyzed simultaneously；Beta-glucosidase just for β-type glycosidic bond in natural glucosides, and it is unrelated with the chemical structure of aglycone in natural glucosides, by natural glycoside hydrolysis At aglycone (e.g., isoflavones) and sugar (e.g., glucose)；Flavonoid Glycosides (hydroxyl-OH, including flavonoids glycosides and Isoflavone aglycone) all there is C6-C3-C6Basic skeleton structure, and it is most of be C-O glucosides key connection O- glycosides, so therein Glycosidic bond, can be by its hydrolytic cleavage to beta-glucosidase not essential difference；Glycosidic bond in polydatin is also same Sample can be by beta-glucosidase hydrolytic cleavage；The present invention is with beta-glucosidase enzyme hydrolysis flavonoid glycoside and polydatin, main needle To C-O glycosidic bond (passing through the O bridge in hydroxyl-OH), this is a kind of most weak glycosidic bond of bond energy, is easiest to by beta-glucosidase Hydrolytic cleavage.In natural flavone glycoside (hydroxyl-OH, including flavonoids glycosides and isoflavone aglycone) of the present invention and polydatin Glycosidic bond can be by beta-glucosidase hydrolytic cleavage.The biochemical reaction condition of beta-glucosidase also has been disclosed in the prior art And its mechanism of action of hydrolysing p-glucosidic bonds, beta-glucosidase and its biochemical reaction condition are natural β-hydrolysis of glycoside bond fractures Necessary and sufficient conditions.
According to existing knowledge, triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside activity Aglycon (not including anthocyanidin) is insoluble or is insoluble in water, is also insoluble in neutral aqueous solution, but be dissolved in dilute alkaline aqueous solution.
According to existing knowledge, triterpenoid saponin is by triterpenoid sapogenin and sugared (glucose, galactolipin, rhamnose, Arab Sugar, xylose) or uronic acid and other organic acids (containing carboxyl) composition, it has been found that up to more than 30 types.Triterpenoid saponin has carboxylic more Base, therefore it is called acid saponin(e again, triterpenoid saponin is dissolved in water more.
Inventive principle:
1, the relative density of sodium chloride is 2.165, and the relative density of potassium chloride is 1.98.Relative density unit: gram/cube Centimetre or milliliter, it is same as below.
2, the prior art, triterpenoid saponin/flavonoid glycoside/resveratrol glucoside aqueous solution is in beta-glucosidase enzyme effect Lower hydrolysis, 40 DEG C -50 DEG C of temperature, PH4.5-5 generate sugar and free triterpenoid saponin active aglycone/flavonoid glycoside activity Aglycon/resveratrol glucoside active aglycone molecule.
3, active aglycone/resveratrol glucoside active aglycone of triterpenoid saponin active aglycone/flavonoid glycoside of the present invention Refer to the aglycone in triterpenoid saponin/flavonoid glycoside/resveratrol glucoside, is free of glycosyl, i.e. active aglycone.
4, triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium The principle separated with triterpenoid saponin/flavonoid glycoside/resveratrol glucoside/glucose aqueous solution of saltouing of salt or sylvite:
In the enzymatic hydrolysis of triterpenoid saponin/flavonoid glycoside/resveratrol glucoside aqueous solution beta-glucosidase, Triterpenoid saponin/flavonoid glycoside/resveratrol glucoside can not be by complete hydrolysis at triterpenoid saponin active aglycone/flavonoid glycoside Active aglycone/resveratrol glucoside active aglycone, need the unhydrolysed triterpenoid saponin/flavonoid glycoside in part/white Chenopodiaceae Reed alcohol glucosides and hydrolysate glucose and triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside Active aglycone separation and by the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside First 1000 times with it are separated with the water improved quality.Triterpenoid saponin/flavonoid glycoside/resveratrol glucoside is due to containing highly-water-soluble Glycosyl, so it can be dissolved in water, this is just triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol The active aglycone of glucosides separates the condition of providing with triterpenoid saponin/flavonoid glycoside/resveratrol glucoside.
Due to generally containing the palmitinic acid of high degree of dispersion or/and the acid of oleic acid in a large amount of water-insoluble water in natural plants Rouge, so water is insoluble or the active glycosides with lipophilic hydrolysate triterpenoid saponin active aglycone/flavonoid glycoside of indissoluble Member/resveratrol glucoside active aglycone by the sour rouge of palmitinic acid or/and oleic acid adsorb and sweep along and suspended dispersed in water, because This triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone cannot precipitate and moisture From.It is hydrophilic on triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone molecule Hydroxy or carboxy number is few (between 1-5), and hydrophily is weak.
Sodium chloride/potassium chloride Nacl/Kcl can destroy triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white Chenopodiaceae Hydrogen bond between hydroxy or carboxy and hydrone or polar attraction on the active aglycone molecule of reed alcohol glucosides and reduce triterpene soap The dissolution of the water of glycosides active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone and its sodium salt or sylvite Degree；With the rising of sodium chloride/potassium chloride Nacl/Kcl water solubility, the triterpenoid saponin that hydrophily is weak in PH6.8-7 is active Aglycon/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite can gradually be separated from water and In water-insoluble segregation, and with water-soluble triterpenoid saponin/flavonoid glycoside/resveratrol glucoside/glucose or other Glycosidic bond combines the aqueous solution separation of sugar.
Triterpenoid saponin/flavonoid glycoside/resveratrol glucoside/glucose hydrophily is greater than sodium chloride or potassium chloride The hydrophily of the hydrophily of Nacl/Kcl, sodium chloride or potassium chloride Nacl/Kcl are much larger than triterpenoid saponin active aglycone/flavonoids Active aglycone/resveratrol glucoside active aglycone of glucosides or its sodium salt/sylvite hydrophily；Glucose is than sodium chloride or chlorine It is stronger that change potassium Nacl/Kcl is more soluble in water, its hydrophily；So glucose and triterpenoid saponin/flavonoid glycoside in water/white Veratryl alcohol glucosides can reduce the saturation solubility of sodium chloride or potassium chloride Nacl/Kcl.Due to triterpenoid saponin/flavonoid glycoside/ Resveratrol glucoside/glucose water solubility (hydrophily) is far longer than triterpenoid saponin active aglycone/flavonoid glycoside activity Aglycon/resveratrol glucoside active aglycone or its sodium salt/sylvite hydrophily, form great contrast；Triterpenoid saponin/flavones Class glucosides/resveratrol glucoside/glucose cannot assemble separation in sodium chloride or potassium chloride Nacl/Kcl aqueous solution, and such three Terpene saponin(e active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite exist In PH6.8-7 and 25 DEG C -50 DEG C of sodium chloride or potassium chloride saturated aqueous solution just with triterpenoid saponin/flavonoid glycoside/white black false hellebore The separation of alcohol glucosides/glucose aqueous solution.
Active aglycone containing triterpenoid saponin/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium The temperature of salt/sylvite triterpenoid saponin/flavonoid glycoside/resveratrol glucoside hydrolysis aqueous solution is kept at 25 DEG C -50 DEG C Aqueous solution is in neutrality；With the saturation solubility aqueous solution of sodium chloride or potassium chloride Nacl/Kcl to active aglycone containing triterpenoid saponin/ Active aglycone/resveratrol glucoside active aglycone of flavonoid glycoside or its sodium salt/sylvite triterpenoid saponin/flavonoids sugar Glycosides/resveratrol glucoside hydrolysis aqueous solution is saltoutd, and the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside can be made Member/resveratrol glucoside active aglycone or its sodium salt/sylvite are hydrolyzed from triterpenoid saponin/flavonoid glycoside/resveratrol glucoside Aqueous solution in segregation；With sodium chloride or potassium chloride Nacl/Kcl 25 DEG C -50 DEG C triterpenoid saponin/flavonoid glycoside/ Resveratrol glucoside hydrolysis aqueous solution in saturation solubility when, the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside Member/resveratrol glucoside active aglycone or its sodium salt/sylvite saltouts, from triterpenoid saponin/flavonoid glycoside/resveratrol glucoside The effect of segregation is best in the aqueous solution of hydrolysis, can make triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white The active aglycone of veratryl alcohol glucosides or its sodium salt/sylvite are kept completely separate with water and its water-soluble substances.0 DEG C -25 DEG C of low temperature can Accelerate triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite It saltouts the segregation from aqueous solution.Active aglycone/resveratrol glucoside the work of triterpenoid saponin active aglycone/flavonoid glycoside Property saturated aqueous solution insoluble in sodium chloride or potassium chloride Nacl/Kcl of aglycon or its sodium salt/sylvite.
Triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/ In the conjugate of sylvite and fatty acid or fatty acid ester, main component is fatty acid or fatty acid ester (oleic acid or/and palmitinic acid Sour rouge), so the relative density of its conjugate is not more than 1.1；And the phase of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution 1.1 are greater than to density, reaches 1.2 or more；So triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white black false hellebore The conjugate of the active aglycone of alcohol glucosides or its sodium salt/sylvite and fatty acid or fatty acid ester can be from sodium chloride or potassium chloride Suspend separation in Nacl/Kcl saturated aqueous solution.
7, the relative density of the fatty acid of natural plants oil-soluble or fatty acid ester (such as oleic acid, palmitinic acid) impurity is all small In 1 (water 1, gram/cc or milliliter).Oleic acid freezing point (DEG C): 13.2, palmitinic acid fusing point (DEG C): 63.1.It is natural to contain three Palmitinic acid and oleic acid are mainly contained in terpene saponin(e/flavonoid glycoside/resveratrol glucoside plant (or fruit), wherein palmitinic acid Content is maximum, palmitic acid content be triterpenoid saponin active aglycone after triterpenoid saponin/flavonoid glycoside/resveratrol glucoside hydrolysis/ 10 times or more of active aglycone/resveratrol glucoside active aglycone of flavonoid glycoside or its sodium salt/sylvite product quality.
The present invention utilizes the sour rouge of palmitinic acid or/and oleic acid from triterpenoid saponin/flavonoid glycoside/resveratrol glucoside/Portugal Suspend separation triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside activity in grape sugar aqueous solution Aglycon or its sodium salt/sylvite；Sodium chloride or potassium chloride Nacl/Kcl are used again, to increase the relative density of aqueous solution, then at 0 DEG C -5 8-24 hours are stood at DEG C, fatty acid or fatty acid ester is made intensively to suspend separation in solid oil smectic, triterpenoid saponin active aglycone/ Active aglycone/resveratrol glucoside active aglycone of flavonoid glycoside or its sodium salt/sylvite Precipitation, obtain triterpenoid saponin Active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite.By triterpenoid saponin Active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite and fatty acid or rouge The edible soft water of 10-20 times of its volume is added in the conjugate of fat acid rouge, with triterpenoid saponin/flavonoid glycoside/resveratrol glucoside The aqueous solution of hydrolysis collides fatty acid or fatty acid ester solid particle compared to water is greatly reduced (relative density is less than 1) It is combined into an integrated solid grease, intensively suspends separation at 0 DEG C -5 DEG C in solid oil smectic；Triterpenoid saponin activity glycosides Member/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone or its sodium salt/sylvite (relative density is greater than 1.8) Also combination is mutually collided due to insoluble in neutral saline solution, aggregate and precipitate is precipitated.
Palmitinic acid, also known as palmitic acid, scientific name hexadecanoic acid.It is widely present in nature, has in almost all of grease Content not equal palmitin acid constituents.Molecular formula: C16H32O2, structural formula: CH3(CH2)14COOH.The scale of pearly-lustre is had for white, Exist in the form of glyceride in many oil & fats.It is not soluble in water, it is slightly soluble in cold alcohol and petroleum ether, is dissolved in hot ethanol, second Ether and chloroform etc..Density (g/mL, 25/4 DEG C): 0.8527；Relative density (25 DEG C, 4 DEG C): 0.841480.
Oleic acid, oleic acid are present in all animal and plant fats together with other fatty acid in the form of glyceride.It is relatively close It spends (g/mL, 20/4 DEG C): 0.8935, relative density (g/mL, 25/4 DEG C): 0.845590, relative density (g/mL, 90/4 DEG C): 0.8429。
8, the hydrochloric acid Hcl aqueous solution of 10%-30% and triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white The sodium salt of the active aglycone of veratryl alcohol glucosides/sylvite stirs metathesis reaction, precipitating recycling triterpenoid saponin active aglycone/flavonoids The principle of active aglycone/resveratrol glucoside active aglycone of glucosides:
In the sodium salt of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Or the feed liquid mass ratio of sylvite and hydrochloric acid Hcl aqueous solution is constantly changed than 10-20 with 300-500 revs/min of shear agitation for 1 Become the sodium salt or sylvite of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone The shapes and sizes of particle particle make the active aglycone/resveratrol glucoside work of triterpenoid saponin active aglycone/flavonoid glycoside Property aglycon sodium salt or sylvite come into full contact with and react with hydrochloric acid Hcl aqueous solution, generate hydrogen H reduction triterpenoid saponin active aglycone/ Active aglycone/resveratrol glucoside the active aglycone and sodium chloride of flavonoid glycoside or potassium chloride Nacl/Kcl's is hydrochloric Hcl aqueous solution.Only due to triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone The water solubility of hydrochloric acid Hcl aqueous solution, hydrochloric acid and sodium chloride or potassium chloride is slightly soluble in much larger than triterpenoid saponin active aglycone/flavonoids The water solubility of active aglycone/resveratrol glucoside active aglycone of glucosides, hydrochloric acid and sodium chloride or potassium chloride also inhibit triterpene Saponin(e active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone is molten in hydrochloric acid Hcl aqueous solution Solution.Sodium chloride or potassium chloride cannot be with the active aglycone/resveratrol glucoside work of triterpenoid saponin active aglycone/flavonoid glycoside Property aglycon reaction, because of weak acid (triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside activity Hydroxyl-OH or carboxyl-COOH on aglycon molecule) strong acid hydrochloric acid cannot be generated；Reaction thoroughly can be carried out and be completed.Absolute mistake Triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone of amount can only be opposite because of it It is heavy that density (being greater than 1.8) is assembled much larger than the relative density (less than 1.2) of hydrochloric acid and sodium chloride or potassium chloride solution at this time Precipitation goes out.
Triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone slightly soluble or Be insoluble in hydrochloric acid Hcl aqueous solution, indissoluble or insoluble in neutral water, aqueous solution insoluble in neutral sodium chloride or potassium chloride or Its salt loading aqueous solution.
9, according to existing knowledge, L-cysteine is reducing agent, and the effect in glycoside hydrolysis is to prevent beta-glucosidase The activated centre of enzyme is oxidized and restores the activity of beta-glucosidase；But L-cysteine itself is oxidized into disulfide bond L-cysteine, l-cysteine are slightly soluble in water, are dissolved in dilute acid solution, and the isoelectric point (PI) of l-cysteine is 4.6, adjustable sugar Aqueous acid pH value after glycosides hydrolysis separates l-cysteine Precipitation to the isoelectric point (PI) of l-cysteine.The β-of glucosides Glucuroide enzymatic hydrolysis product has monosaccharide or the oligosaccharides such as aglycone (active aglycone) and glucose, but glucose has aldehyde Base has oxidisability and reproducibility, the activated centre of beta-glucosidase can be aoxidized, so glucose is beta-glucosidase The Exemplary inhibitors of enzymatic hydrolysis；Therefore reducing agent L-cysteine is added, to prevent the activated centre quilt of beta-glucosidase Oxidation and the activity for restoring beta-glucosidase.
Cystine also known as l-cysteine, 3,3 '-dithio dipropyl propylhomoserins etc., No. CAS is 56-89-3, and chemical formula is C6H12N2O4S2.It is to be found from vesical calculus in 1810 by Wollaston.1832, Berzelius was named as Cystine, it is a kind of sulfur-containing amino acid, there is a small amount of presence in protein, in the keratin mostly contained in hair, paw etc..? It can be obtained using synthetic method.For industries such as medicine, food, cosmetics etc..
L-cysteine, water-soluble: 0.112g/L (25 DEG C), white flaky crystals or crystalline powder；It is atomic to be dissolved in water； Insoluble in ethyl alcohol and other organic solvents, it is soluble in diluted acid；Isoelectric point pl4.6.
10, sodium chloride Nacl water solubility (gram/100 grams of water): 0 DEG C: 35.7g, 10 DEG C: 35.8g, 20 DEG C: 36.0g, 30 DEG C: 36.3g, 40 DEG C: 36.6g, 50 DEG C: 37.0g, 60 DEG C: 37.3g, 70 DEG C: 37.8g, 80 DEG C: 38.4g, 90 DEG C: 39.0g, 100 DEG C: 39.8g.
11, potassium chloride Kcl water solubility (gram/100 grams of water):
0℃ 10℃ 20℃ 30℃ 40℃ 60℃ 70℃ 80℃ 90℃ 100℃
28g 31.2g 34.2g 37.2g 40.1g 45.8g 48.8g 51.3g 53.9g 56.3g。
The technical solution adopted by the present invention to solve the technical problems is:
1, extracting method of the present invention the following steps are included:
One, the extraction of triterpene saponin:
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants triterpenoid saponin aqueous solution, it protects Protect the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains living containing triterpenoid saponin Property aglycon/triterpenoid saponin/glucose aqueous solution, containing the oil-soluble relative density dispersed in acidic aqueous solution less than 1 Fatty acid or fatty acid ester impurity, triterpenoid saponin active aglycone by the sour rouge of oleic acid or/and palmitinic acid adsorb and suspended dispersed In aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, contain to oleic acid or/and palmitinic acid The sour rouge that suitable oleic acid or/and palmitinic acid need to be added in low triterpenoid saponin aqueous solution is measured, so that can be complete in following (three) Triterpenoid saponin active aglycone in the full separation triterpenoid saponin aqueous solution that suspends；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the triterpenoid saponin hydrolysis aqueous solution of above-mentioned (one) Be conducive to make it to reduce and overcome dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution to PH6.8-7 Aggregation, which suspends, in the salt loading aqueous solution of sodium chloride or potassium chloride separates；With sodium bicarbonate or saleratus NaHCO3/KHCO3 Aqueous solution titrates or is divided into repeatedly or is at the uniform velocity added and neutralizes, and stirs rapidly, 200-500 revs/min of mixing speed；Make sodium bicarbonate Or saleratus is evenly distributed in acidic aqueous solution；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the living containing triterpenoid saponin of above-mentioned (two) Property aglycon/triterpenoid saponin/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, 25 DEG C- At 50 DEG C, using the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water as reference value, then This active aglycone containing triterpenoid saponin/triterpenoid saponin/glucose water is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Solution dissolution, stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；It further takes out containing triterpenoid saponin The aqueous solution of active aglycone/triterpenoid saponin/glucose/sodium chloride or potassium chloride；3-8 hours are stood, fatty acid or fatty acid are made Rouge impurity sweeps along, adsorbs, the mixing conjugate of the water-insoluble triterpenoid saponin active aglycone of physical bond is because its relative density is less than The relative density of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution and intensively suspend separation in solid water-insoluble；And with three The separation of the aqueous solution of terpene saponin(e and glucose and sodium chloride or potassium chloride；
(4), the triterpenoid saponin active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester, mistake are taken out Filter moisture therein；Its volume 10-20 is added in the conjugate of this triterpenoid saponin active aglycone and fatty acid or fatty acid ester again Edible soft water again, appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, The relative density of its aqueous solution is set to be greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid ester in solid Grease-like intensively suspends separation, and also most aggregate and precipitate is separated from water triterpenoid saponin active aglycone at this time；It obtains containing a small amount of water Solid triterpenoid saponin active aglycone product；Vacuum dehydration is dry again, obtains triterpenoid saponin active aglycone product；
The relative density of triterpenoid saponin active aglycone is greater than 1.8, much larger than the saturation of sodium chloride or potassium chloride Nacl/Kcl Aqueous solution relative density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Two, the extraction of flavonoids aglycon
It is (one) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants flavonoid glycoside aqueous solution, Protect the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains containing flavonoids sugar Glycosides active aglycone/flavonoid glycoside/glucose aqueous solution, contains the oil-soluble relative density dispersed in acidic aqueous solution Fatty acid or fatty acid ester impurity less than 1, flavonoid glycoside active aglycone are adsorbed and hanged by the sour rouge of oleic acid or/and palmitinic acid Floating dispersion is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/and palm fibre The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the low flavonoid glycoside aqueous solution of palmitic acid acid content, so that can be following (3) the flavonoid glycoside active aglycone in the separating flavone class glucosides aqueous solution that suspends completely in；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3The flavonoid glycoside hydrolysis for neutralizing above-mentioned (one) is water-soluble Liquid is conducive to make to PH6.8-7 to reduce and overcome dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution It assembles suspension separation in the salt loading aqueous solution of sodium chloride or potassium chloride；With sodium bicarbonate or saleratus NaHCO3/ KHCO3Aqueous solution titrates or is divided into repeatedly or is at the uniform velocity added and neutralizes, and stirs rapidly, 200-500 revs/min of mixing speed；Make carbon Sour hydrogen sodium or saleratus are evenly distributed in acidic aqueous solution；
(3) sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares above-mentioned (two) containing flavonoid glycoside activity Aglycon/flavonoid glycoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, 25 DEG C- At 50 DEG C, using the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water as reference value, then This active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Aqueous dissolution, stand 1-3 minute, make excessive sodium chloride or potassium chloride immediately Precipitation separation；It further takes out containing flavones Class glycosidase activity aglycon/flavonoid glycoside/glucose aqueous solution；3-8 hours are stood, fatty acid or fatty acid ester impurity are wrapped up in It holds under the arm, adsorb, the mixing conjugate of the water-insoluble flavonoid glycoside active aglycone of physical bond is because its relative density is less than sodium chloride Or potassium chloride Nacl/Kcl saturated aqueous solution relative density and intensively suspend separation in solid water-insoluble；And it is sugared with flavonoids The separation of the aqueous solution of glycosides and glucose and sodium chloride or potassium chloride；
(4), the flavonoid glycoside active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, Filter moisture therein；Its volume is added in the conjugate of this flavonoid glycoside active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution for 10-20 times of edible soft water Concentration makes the relative density of its aqueous solution be greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid ester is in Solid oil smectic intensively suspends separation, and also most aggregate and precipitate is separated from water flavonoid glycoside active aglycone at this time；It obtains containing few Measure the solid flavonoid glycoside active aglycone product of water；Vacuum dehydration is dry again, obtains flavonoid glycoside active aglycone product；
The relative density of flavonoid glycoside active aglycone is greater than 1.8, full much larger than sodium chloride or potassium chloride Nacl/Kcl With aqueous solution relative density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Three, the extraction of resveratrol aglycon
(1) by the beta-glucosidase enzyme hydrolysis of natural plants resveratrol glucoside aqueous solution, with L-cysteine antioxygen Change, protects the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains containing white Chenopodiaceae Reed alcohol glycosidase activity aglycon/resveratrol glucoside/glucose aqueous solution, it is oil-soluble containing what is dispersed in acidic aqueous solution Fatty acid of the relative density less than 1 or fatty acid ester impurity, resveratrol glucoside active aglycone is by oleic acid or/and the acid of palmitinic acid Rouge absorption and suspended dispersed in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oil The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in sour or/and low palmitic acid content resveratrol glucoside aqueous solution, so that Resveratrol glucoside active aglycone in the separation resveratrol glucoside aqueous solution that can suspend completely in following (three)；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the resveratrol glucoside hydrolysis water of above-mentioned (one) Solution is conducive to PH6.8-7 with reducing and overcoming dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution It is set to assemble suspension separation in the salt loading aqueous solution of sodium chloride or potassium chloride；With sodium bicarbonate or saleratus NaHCO3/ KHCO3Aqueous solution titrates or is divided into repeatedly or is at the uniform velocity added and neutralizes, and stirs rapidly, 200-500 revs/min of mixing speed；Make carbon Sour hydrogen sodium or saleratus are evenly distributed in acidic aqueous solution；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the sugared containing resveratrol of above-mentioned (two) Glycosides active aglycone/resveratrol glucoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, It is ginseng with the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water at 25 DEG C -50 DEG C Value is examined, then this active aglycone containing resveratrol glucoside/resveratrol is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Glucosides/glucose aqueous dissolution stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；Again Take out the aqueous solution of active aglycone containing resveratrol glucoside/resveratrol glucoside/glucose/sodium chloride or potassium chloride；Stand 3-8 Hour, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, the water-insoluble resveratrol glucoside active aglycone of physical bond it is mixed It closes conjugate and is in solid water because its relative density is less than the relative density of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution Insoluble matter intensively suspends separation；And it is separated with the aqueous solution of resveratrol glucoside and glucose and sodium chloride or potassium chloride；
(4), the resveratrol glucoside active aglycone of above-mentioned (three) is taken out in conjunction with the mixing of fatty acid or fatty acid ester Object filters moisture therein；It is added in the conjugate of this resveratrol glucoside active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated water for 10-20 times of volume of edible soft water Solution concentration makes the relative density of its aqueous solution be greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid Rouge intensively suspends separation in solid oil smectic, and also most aggregate and precipitate is separated from water resveratrol glucoside active aglycone at this time；? To the solid resveratrol glucoside active aglycone product containing a small amount of water；Vacuum dehydration is dry again, obtains resveratrol glucoside activity Aglycon product；
The relative density of resveratrol glucoside active aglycone is greater than 1.8, much larger than sodium chloride or potassium chloride Nacl/Kcl Saturated aqueous solution relative density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
The above sodium bicarbonate or saleratus NaHCO3/KHCO3It can also partially be replaced with sodium carbonate or potassium carbonate.
2. the three of active aglycone containing triterpenoid saponin/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Terpene saponin(e/flavonoid glycoside/resveratrol glucoside acidic aqueous solution is being carbonated hydrogen sodium or saleratus NaHCO3/KHCO3In And when, the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside of the specific kind in part Activity hydroxy (- OH) or pendant carboxylic group (- COOH) in member are possible to part and are carbonated hydrogen sodium or saleratus NaHCO3/KHCO3 It neutralizes, and triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone is made to generate its phase The sodium salt or sylvite answered, and with triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside activity Aglycon is swept along by the sour rouge of palmitinic acid, adsorbs, physical bond simultaneously, and suspends and be separated from water.
3. triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone is corresponding Sodium salt or sylvite be reduced into the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside The method of member:
At 5 DEG C -- at 30 DEG C, by triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white Chenopodiaceae of water-insoluble The sodium salt or sylvite of the active aglycone of reed alcohol glucosides are stirred with the hydrochloric acid Hcl aqueous solution of slightly excessive mass ratio 10%-30% with it Reaction is mixed, 300-500 revs/min of mixing speed, makes the active glycosides of triterpenoid saponin active aglycone/flavonoid glycoside of water-insoluble Member/resveratrol glucoside active aglycone sodium salt or sylvite are sufficiently reacted with hydrochloric acid Hcl aqueous solution, generate the triterpene of hydrogen H reduction The sediment and sodium chloride or chlorine of saponin(e active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Change the aqueous acid of potassium；Triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone The feed liquid mass ratio of sodium salt or sylvite and hydrochloric acid Hcl aqueous solution compares 10-20 for 1；Triterpenoid saponin activity glycosides is taken out in filtering or layering Member/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone sediment, then at 1 DEG C -25 DEG C with a small amount of edible Water washing hydrochloric acid therein, precipitation and separation triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside Active aglycone obtains consolidating for triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Body object；Vacuum dehydration is dry again, obtains triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside Active aglycone product；The active glycosides of active aglycone/resveratrol glucoside containing micro triterpenoid saponin active aglycone/flavonoid glycoside The aqueous hydrochloric acid solution of member recycles；Active aglycone/resveratrol glucoside the work of triterpenoid saponin active aglycone/flavonoid glycoside Property aglycon is only slightly soluble in hydrochloric acid Hcl aqueous solution, and sodium chloride or potassium chloride Nacl/Kcl can further decrease triterpenoid saponin activity glycosides Solubility of member/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone in hydrochloric acid Hcl aqueous solution.
Extracting method of the present invention is preferred are as follows:
It is made of the following steps:
One, the extraction of triterpene saponin:
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants triterpenoid saponin aqueous solution, it protects Protect the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 48 hours；Obtain active aglycone containing triterpenoid saponin/tri- Terpene saponin(e/glucose aqueous solution, containing fatty acid of the oil-soluble relative density less than 1 dispersed in acidic aqueous solution or Fatty acid ester impurity, triterpenoid saponin active aglycone by the sour rouge of oleic acid or/and palmitinic acid adsorb and suspended dispersed in aqueous solution； Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, the triterpene soap low to oleic acid or/and palmitic acid content The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in glycosides aqueous solution, so that the separation three that can suspend completely in following (three) Triterpenoid saponin active aglycone in terpene saponin(e aqueous solution；
(2), with sodium bicarbonate NaHCO3The triterpenoid saponin for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH7；
(3), sodium chloride Nacl is added in above-mentioned (two), prepares active aglycone containing the triterpenoid saponin/triterpene soap of above-mentioned (two) The salt loading aqueous solution of glycosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C, with its certain The saturation solubility amount of sodium chloride Nacl in water at a temperature of one is reference value, then this is added in the sodium chloride Nacl of the numerical value Active aglycone containing triterpenoid saponin/triterpenoid saponin/glucose aqueous dissolution stands 1-3 minutes, makes excessive sodium chloride immediately Precipitation separation；Further take out active aglycone containing triterpenoid saponin/triterpenoid saponin/glucose/sodium chloride aqueous solution；It is small to stand 8 When, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, the mixing of the water-insoluble triterpenoid saponin active aglycone of physical bond combines Object is in that solid water-insoluble intensively suspends separation because its relative density is less than the relative density of sodium chloride Nacl saturated aqueous solution； And it is separated with the aqueous solution of triterpenoid saponin and glucose and sodium chloride；
(4), the triterpenoid saponin active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester, mistake are taken out Filter moisture therein；10 times of its volume is added in the conjugate of this triterpenoid saponin active aglycone and fatty acid or fatty acid ester again Edible soft water, appropriate sodium chloride Nacl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes the opposite of its aqueous solution Density is greater than 1；24 hours are stood at 0 DEG C again, so that fatty acid or fatty acid ester is intensively suspended separation in solid oil smectic, at this time Also most aggregate and precipitate is separated from water triterpenoid saponin active aglycone；The solid triterpenoid saponin active aglycone containing a small amount of water is obtained to produce Product；Vacuum dehydration is dry again, obtains triterpenoid saponin active aglycone product；
The relative density of triterpenoid saponin active aglycone is greater than 1.8, and the saturated aqueous solution much larger than sodium chloride Nacl is relatively close Degree；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Two, the extraction of flavonoids aglycon
It is (one) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants flavonoid glycoside aqueous solution, Protect the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 48 hours；Obtain the glycosides of activity containing flavonoid glycoside Member/flavonoid glycoside/glucose aqueous solution, containing the oil-soluble relative density dispersed in acidic aqueous solution less than 1 Fatty acid or fatty acid ester impurity, flavonoid glycoside active aglycone are adsorbed and suspended dispersed by the sour rouge of oleic acid or/and palmitinic acid In aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, contain to oleic acid or/and palmitinic acid The sour rouge that suitable oleic acid or/and palmitinic acid need to be added in low flavonoid glycoside aqueous solution is measured, so that can be in following (three) Flavonoid glycoside active aglycone in complete suspension separating flavone class glucosides aqueous solution；
(2), with sodium bicarbonate NaHCO3The flavonoid glycoside for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH7；
(3), sodium chloride Nacl is added in above-mentioned (two), prepares active aglycone containing the flavonoid glycoside/flavones of above-mentioned (two) The salt loading aqueous solution of class glucosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C, with The saturation solubility amount of sodium chloride Nacl in water at its a certain temperature is reference value, then the sodium chloride Nacl of the numerical value is added Enter this active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose aqueous dissolution, stands 1-3 minutes, make excessive chlorine Changing sodium, Precipitation separates immediately；Further take out active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose aqueous solution；It is quiet It sets 8 hours, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, physical bond water-insoluble flavonoid glycoside active aglycone It is in that solid water-insoluble is intensive that conjugate, which is mixed, because its relative density is less than the relative density of sodium chloride Nacl saturated aqueous solution Suspend separation；And it is separated with the aqueous solution of flavonoid glycoside and glucose and sodium chloride；
(4), the flavonoid glycoside active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, Filter moisture therein；Its volume 10 is added in the conjugate of this flavonoid glycoside active aglycone and fatty acid or fatty acid ester again Edible soft water again, appropriate sodium chloride Nacl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes its aqueous solution Relative density is greater than 1；24 hours are stood at 0 DEG C again, fatty acid or fatty acid ester is made intensively to suspend separation in solid oil smectic, Also most aggregate and precipitate is separated from water flavonoid glycoside active aglycone at this time；Obtain the solid flavonoid glycoside activity containing a small amount of water Aglycon product；Vacuum dehydration is dry again, obtains flavonoid glycoside active aglycone product；
The relative density of flavonoid glycoside active aglycone is greater than 1.8, and the saturated aqueous solution much larger than sodium chloride Nacl is opposite Density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Three, the extraction of resveratrol aglycon
(1) by the beta-glucosidase enzyme hydrolysis of natural plants resveratrol glucoside aqueous solution, with L-cysteine antioxygen Change, protects the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 48 hours；It obtains living containing resveratrol glucoside Property aglycon/resveratrol glucoside/glucose aqueous solution is small containing the oil-soluble relative density dispersed in acidic aqueous solution In 1 fatty acid or fatty acid ester impurity, resveratrol glucoside active aglycone is adsorbed and hanged by the sour rouge of oleic acid or/and palmitinic acid Floating dispersion is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/and palm fibre The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the low resveratrol glucoside aqueous solution of palmitic acid acid content, so that can be under State the resveratrol glucoside active aglycone in the separation resveratrol glucoside aqueous solution that suspends completely in (three)；
(2), with sodium bicarbonate NaHCO3The resveratrol glucoside for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH7；
(3), by above-mentioned (two) be added sodium chloride Nacl, prepare above-mentioned (two) active aglycone containing resveratrol glucoside/it is white The salt loading aqueous solution of veratryl alcohol glucosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C When, using the saturation solubility amount of the sodium chloride Nacl at its a certain temperature in water as reference value, then by the sodium chloride of the numerical value This active aglycone containing resveratrol glucoside/resveratrol glucoside/glucose aqueous dissolution is added in Nacl, stands 1-3 minutes, Making excessive sodium chloride, Precipitation separates immediately；Further take out active aglycone containing resveratrol glucoside/resveratrol glucoside/grape Sugar/sodium chloride aqueous solution；Stand 8 hours, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, physical bond it is water-insoluble The mixing conjugate of resveratrol glucoside active aglycone is less than the relatively close of sodium chloride Nacl saturated aqueous solution because of its relative density Degree and intensively suspend separation in solid water-insoluble；And it is separated with the aqueous solution of resveratrol glucoside and glucose and sodium chloride；
(4), the resveratrol glucoside active aglycone of above-mentioned (three) is taken out in conjunction with the mixing of fatty acid or fatty acid ester Object filters moisture therein；It is added in the conjugate of this resveratrol glucoside active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride Nacl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes its water for 10 times of volume of edible soft water The relative density of solution is greater than 1；24 hours are stood at 0 DEG C again, hangs fatty acid or fatty acid ester intensively in solid oil smectic Floating separation, also most aggregate and precipitate is separated from water resveratrol glucoside active aglycone at this time；Obtain the white Chenopodiaceae of solid containing a small amount of water Reed alcohol glycosidase activity aglycon product；Vacuum dehydration is dry again, obtains resveratrol glucoside active aglycone product.
Beneficial effects of the present invention:
The present invention is compared with prior art:
1. the present invention is to the triterpenoid saponin/flavonoids sugar of (mass ratio is below one thousandth) micro in natural plant raw material The extraction of glycosides/resveratrol glucoside and its active aglycone is more complete, its 99% or more effective component can be extracted, be kept away The waste of resource is exempted from.
2. high production efficiency of the present invention does not need to slough a large amount of moisture, energy saving, production highly shortened Time, production cost are low.It is nontoxic that the present invention produces waste water, can safely discharge or recycling and reusing or as agricultural fertilizer (potassium chloride waste water).
3. protecting environment present invention greatly reduces the discharge amount of production organic waste residues.
It is of the invention swept along, adsorbed with oleic acid or/and palmitinic acid, physical bond triterpenoid saponin active aglycone/flavonoids sugar Active aglycone/resveratrol glucoside active aglycone of glycosides or its sodium salt/sylvite, then in sodium chloride or potassium chloride Nacl/Kcl The lower separation triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside that suspends of saturated aqueous solution effect Active aglycone or its sodium salt/sylvite, after in 0 DEG C -5 DEG C, appropriate sodium chloride or potassium chloride Nacl/Kcl or reach its saturated water again Solution (prepares) separation oleic acid or/and palmitinic acid impurity with the edible soft water for extracting 10-20 times of conjugate volume, these steps Combination is that core of the invention technology innovates essential features.
Specific embodiment:
With regard to embodiment, the invention will be further described below:
Embodiment 1:
One, the extraction of triterpene saponin:
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants triterpenoid saponin aqueous solution, it protects Protect the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains living containing triterpenoid saponin Property aglycon/triterpenoid saponin/glucose aqueous solution, containing the oil-soluble relative density dispersed in acidic aqueous solution less than 1 Fatty acid or fatty acid ester impurity, triterpenoid saponin active aglycone by the sour rouge of oleic acid or/and palmitinic acid adsorb and suspended dispersed In aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, contain to oleic acid or/and palmitinic acid The sour rouge that suitable oleic acid or/and palmitinic acid need to be added in low triterpenoid saponin aqueous solution is measured, so that can be complete in following (three) Triterpenoid saponin active aglycone in the full separation triterpenoid saponin aqueous solution that suspends；
(2), with saleratus KHCO3The triterpenoid saponin for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH6.8-7；
(3), potassium chloride Kcl is added in above-mentioned (two), prepares active aglycone containing the triterpenoid saponin/triterpene soap of above-mentioned (two) The salt loading aqueous solution of glycosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C, with its certain The saturation solubility amount of potassium chloride Kcl in water at a temperature of one is reference value, then this is added in the potassium chloride Kcl of the numerical value and is contained Triterpenoid saponin active aglycone/triterpenoid saponin/glucose aqueous dissolution stands 1-3 minutes, excessive potassium chloride is made to sink immediately Precipitation goes out to separate；Further take out active aglycone containing triterpenoid saponin/triterpenoid saponin/glucose/potassium chloride aqueous solution；It is small to stand 3-8 When, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, the mixing of the water-insoluble triterpenoid saponin active aglycone of physical bond combines Object is in that solid water-insoluble intensively suspends separation because its relative density is less than the relative density of potassium chloride Kcl saturated aqueous solution； And it is separated with the aqueous solution of triterpenoid saponin and glucose and potassium chloride；
(4), the triterpenoid saponin active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester, mistake are taken out Filter moisture therein；Its volume 10-20 is added in the conjugate of this triterpenoid saponin active aglycone and fatty acid or fatty acid ester again Edible soft water again, appropriate potassium chloride Kcl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes its aqueous solution Relative density is greater than 1；8 hours are stood at 0 DEG C -5 DEG C again, so that fatty acid or fatty acid ester is intensively suspended in solid oil smectic and divides From also most aggregate and precipitate is separated from water triterpenoid saponin active aglycone at this time；Obtain the solid triterpenoid saponin activity containing a small amount of water Aglycon product；Vacuum dehydration is dry again, obtains triterpenoid saponin active aglycone product；
The relative density of triterpenoid saponin active aglycone is greater than 1.8, and the saturated aqueous solution much larger than potassium chloride Kcl is relatively close Degree；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Two, the extraction of flavonoids aglycon
It is (one) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants flavonoid glycoside aqueous solution, Protect the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains containing flavonoids sugar Glycosides active aglycone/flavonoid glycoside/glucose aqueous solution, contains the oil-soluble relative density dispersed in acidic aqueous solution Fatty acid or fatty acid ester impurity less than 1, flavonoid glycoside active aglycone are adsorbed and hanged by the sour rouge of oleic acid or/and palmitinic acid Floating dispersion is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/and palm fibre The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the low flavonoid glycoside aqueous solution of palmitic acid acid content, so that can be following (3) the flavonoid glycoside active aglycone in the separating flavone class glucosides aqueous solution that suspends completely in；
(2), with saleratus KHCO3The flavonoid glycoside for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH6.8-7；
(3), potassium chloride Kcl is added in above-mentioned (two), prepares active aglycone containing the flavonoid glycoside/flavones of above-mentioned (two) The salt loading aqueous solution of class glucosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C, with The saturation solubility amount of potassium chloride Kcl in water at its a certain temperature is reference value, then the potassium chloride Kcl of the numerical value is added This active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose aqueous dissolution stands 1-3 minutes, makes excessive chlorination Precipitation separates potassium immediately；Further take out active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose aqueous solution；It stands 3-8 hours, fatty acid or rouge _ _ fat acid rouge impurity is set to sweep along, adsorb, the water-insoluble flavonoid glycoside active aglycone of physical bond Mixing conjugate because its relative density be less than potassium chloride Kcl saturated aqueous solution relative density due to be in that solid water-insoluble is intensive Suspend separation；And it is separated with the aqueous solution of flavonoid glycoside and glucose and potassium chloride；
(4), the flavonoid glycoside active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, Filter moisture therein；Its volume is added in the conjugate of this flavonoid glycoside active aglycone and fatty acid or fatty acid ester again Appropriate potassium chloride Kcl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, keeps its water-soluble for 10-20 times of edible soft water The relative density of liquid is greater than 1；8 hours are stood at 0 DEG C -5 DEG C again, hangs fatty acid or fatty acid ester intensively in solid oil smectic Floating separation, also most aggregate and precipitate is separated from water flavonoid glycoside active aglycone at this time；Obtain the solid flavonoids containing a small amount of water Glycosidase activity aglycon product；Vacuum dehydration is dry again, obtains flavonoid glycoside active aglycone product；
The relative density of flavonoid glycoside active aglycone is greater than 1.8, and the saturated aqueous solution much larger than potassium chloride Kcl is relatively close Degree；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Three, the extraction of resveratrol aglycon
(1) by the beta-glucosidase enzyme hydrolysis of natural plants resveratrol glucoside aqueous solution, with L-cysteine antioxygen Change, protects the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains containing white Chenopodiaceae Reed alcohol glycosidase activity aglycon/resveratrol glucoside/glucose aqueous solution, it is oil-soluble containing what is dispersed in acidic aqueous solution Fatty acid of the relative density less than 1 or fatty acid ester impurity, resveratrol glucoside active aglycone is by oleic acid or/and the acid of palmitinic acid Rouge absorption and suspended dispersed in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oil The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in sour or/and low palmitic acid content resveratrol glucoside aqueous solution, so that 0 full suspension the resveratrol glucoside active aglycone in resveratrol glucoside aqueous solution can be separated in following (three)；
(2), with saleratus KHCO3The resveratrol glucoside for neutralizing above-mentioned (one) hydrolyzes aqueous solution to PH6.8-7；
(3), by above-mentioned (two) be added potassium chloride Kcl, prepare above-mentioned (two) active aglycone containing resveratrol glucoside/it is white The salt loading aqueous solution of veratryl alcohol glucosides/glucose aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C When, using the saturation solubility amount of the potassium chloride Kcl at its a certain temperature in water as reference value, then by the potassium chloride of the numerical value This active aglycone containing resveratrol glucoside/resveratrol glucoside/glucose aqueous dissolution is added in Kcl, stands 1-3 minutes, Making excessive potassium chloride, Precipitation separates immediately；Further take out active aglycone containing resveratrol glucoside/resveratrol glucoside/grape Sugar/potassium chloride aqueous solution；Stand 3-8 hours, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, physical bond water it is insoluble Resveratrol glucoside active aglycone mixing conjugate because its relative density be less than potassium chloride Kcl saturated aqueous solution it is relatively close Degree and intensively suspend separation in solid water-insoluble；And it is separated with the aqueous solution of resveratrol glucoside and glucose and potassium chloride；
(4), the resveratrol glucoside active aglycone of above-mentioned (three) is taken out in conjunction with the mixing of fatty acid or fatty acid ester Object filters moisture therein；It is added in the conjugate of this resveratrol glucoside active aglycone and fatty acid or fatty acid ester again Appropriate potassium chloride Kcl is added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes it for 10-20 times of volume of edible soft water The relative density of aqueous solution is greater than 1；8 hours are stood at 0 DEG C -5 DEG C again, keeps fatty acid or fatty acid ester close in solid oil smectic Collection, which suspends, to be separated, and also most aggregate and precipitate is separated from water resveratrol glucoside active aglycone at this time；Obtain the solid containing a small amount of water Resveratrol glucoside active aglycone product；Vacuum dehydration is dry again, obtains resveratrol glucoside active aglycone product.
Embodiment 2:
One, the extraction of triterpene saponin:
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants triterpenoid saponin aqueous solution, it protects Protect the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 24 hours；It obtains containing radix bupleuri (ginseng/seven leaves) saponin(e Active aglycone/radix bupleuri (ginseng/seven leaves) saponin(e/glucose aqueous solution, it is oil-soluble containing what is dispersed in acidic aqueous solution Fatty acid of the relative density less than 1 or fatty acid ester impurity, radix bupleuri (ginseng/seven leaves) saponin(e active aglycone is by oleic acid or/and palm fibre The sour rouge of palmitic acid acid adsorb and suspended dispersed in aqueous solution；Fatty acid or fatty acid ester impurity refer to oleic acid or/and palmitinic acid Sour rouge；The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the saponin(e aqueous solution low to oleic acid or/and palmitic acid content, with Allow to radix bupleuri (ginseng/seven leaves) the saponin(e active aglycone separated in saponin(e aqueous solution that suspends completely in following (three)；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the saponin(e hydrolysis aqueous solution of above-mentioned (one) extremely PH6-8；With sodium bicarbonate or saleratus NaHCO3/KHCO3Aqueous solution titrates or is divided into repeatedly or is at the uniform velocity added and neutralizes, rapidly Stirring, 200-500 revs/min of mixing speed；Sodium bicarbonate or saleratus is set to be evenly distributed in acidic aqueous solution；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the glycosides of activity containing saponin(e of above-mentioned (two) Member/saponin(e/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C, with The saturation solubility amount of sodium chloride or potassium chloride Nacl/Kcl in water at its a certain temperature is reference value, then by the numerical value This active aglycone containing saponin(e/saponin(e/glucose aqueous dissolution is added in sodium chloride or potassium chloride Nacl/Kcl, stands 1-3 points Clock, making excessive sodium chloride or potassium chloride, Precipitation separates immediately；Further take out active aglycone containing saponin(e/saponin(e/glucose/chlorine Change the aqueous solution of sodium or potassium chloride；Stand 3 hours, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, physical bond water it is insoluble The mixing conjugate of saponin(e active aglycone be less than sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution because of its relative density Relative density and intensively suspend separation in solid water-insoluble；And the aqueous solution with saponin(e and glucose and sodium chloride or potassium chloride Separation；
(4), the saponin(e active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, it is filtered In moisture；The edible of 10-20 times of its volume is added in the conjugate of this saponin(e active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, keeps its water-soluble for soft water The relative density of liquid is greater than 1；8 hours are stood at 0 DEG C again, so that fatty acid or fatty acid ester is intensively suspended in solid oil smectic and divides From also most aggregate and precipitate is separated from water saponin(e active aglycone at this time；Obtain the solid saponin(e active aglycone product containing a small amount of water； Vacuum dehydration is dry again, obtains radix bupleuri (ginseng/seven leaves) saponin(e active aglycone product；
Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Two, the extraction of flavonoids aglycon
(1) by the beta-glucosidase enzyme hydrolysis of natural plants soybean isoflavone glucoside aqueous solution, with L-cysteine antioxygen Change, protects the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 24 hours；It obtains containing isoflavones activity Aglycon/soybean isoflavone glucoside/glucose aqueous solution is small containing the oil-soluble relative density dispersed in acidic aqueous solution In 1 fatty acid or fatty acid ester impurity, isoflavones active aglycone is adsorbed and suspended by the sour rouge of oleic acid or/and palmitinic acid Dispersion is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid；To oleic acid or/and palm The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the glucosides aqueous solution of the low isoflavones of acid content, so that can be Isoflavones active aglycone in the separation soybean isoflavone glucoside aqueous solution that suspends completely in following (three)；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the Hydrolyzation of Soybean Isoflavone Glycoside of above-mentioned (one) Aqueous solution is to PH6.8；With sodium bicarbonate or saleratus NaHCO3/KHCO3Aqueous solution titrates or is divided into repeatedly or at the uniform velocity in addition With, stirring rapidly, 200-500 revs/min of mixing speed；It is distributed sodium bicarbonate or saleratus in acidic aqueous solution It is even；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), for preparing above-mentioned (two) contains isoflavones Active aglycone/soybean isoflavone glucoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, It is ginseng with the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water at 25 DEG C -50 DEG C Value is examined, then this active aglycone containing isoflavones/isoflavones is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Glucosides/glucose aqueous dissolution stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；Again Take out active aglycone containing isoflavones/soybean isoflavone glucoside/glucose aqueous solution；3 hours are stood, fatty acid or rouge are made Fat acid rouge impurity sweeps along, adsorbs, the mixing conjugate of the water-insoluble isoflavones active aglycone of physical bond is because it is relatively close Degree is less than the relative density of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution and intensively suspends separation in solid water-insoluble； And it is separated with the aqueous solution of soybean isoflavone glucoside and glucose and sodium chloride or potassium chloride；
(4), the isoflavones active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, Filter moisture therein；Its volume is added in the conjugate of this isoflavones active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution for 10-20 times of edible soft water Concentration makes the relative density of its aqueous solution be greater than 1；24 hours are stood at 0 DEG C again, makes fatty acid or fatty acid ester in solid oil Smectic intensively suspends separation, and also most aggregate and precipitate is separated from water isoflavones active aglycone at this time；It obtains containing a small amount of water Dried soy isoflavones active aglycone product；Vacuum dehydration is dry again, obtains isoflavones active aglycone product；
The relative density of isoflavones active aglycone is greater than 1.8, full much larger than sodium chloride or potassium chloride Nacl/Kcl With aqueous solution relative density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Three, the extraction of resveratrol aglycon
(1) by the beta-glucosidase enzyme hydrolysis of natural plants resveratrol glucoside aqueous solution, with L-cysteine antioxygen Change, protects the activity of beta-glucosidase；50 DEG C of hydrolysis temperature, PH4.5, the time 24 hours；It obtains living containing resveratrol glucoside Property aglycon/resveratrol glucoside/glucose aqueous solution is small containing the oil-soluble relative density dispersed in acidic aqueous solution In 1 fatty acid or fatty acid ester impurity, resveratrol glucoside active aglycone is adsorbed and hanged by the sour rouge of oleic acid or/and palmitinic acid Floating dispersion is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/and palm fibre The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the low resveratrol glucoside aqueous solution of palmitic acid acid content, so that can be under State the resveratrol glucoside active aglycone in the separation resveratrol glucoside aqueous solution that suspends completely in (three)；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the resveratrol glucoside hydrolysis water of above-mentioned (one) Solution is to PH6.8；With sodium bicarbonate or saleratus NaHCO3/KHCO3Aqueous solution titrates or is divided into repeatedly or at the uniform velocity in addition With, stirring rapidly, 200-500 revs/min of mixing speed；It is distributed sodium bicarbonate or saleratus in acidic aqueous solution It is even；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the sugared containing resveratrol of above-mentioned (two) Glycosides active aglycone/resveratrol glucoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, It is ginseng with the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water at 25 DEG C -50 DEG C Value is examined, then this active aglycone containing resveratrol glucoside/resveratrol is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Glucosides/glucose aqueous dissolution stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；Again Take out the aqueous solution of active aglycone containing resveratrol glucoside/resveratrol glucoside/glucose/sodium chloride or potassium chloride；It is small to stand 8 When, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, the mixing of the water-insoluble resveratrol glucoside active aglycone of physical bond Conjugate because its relative density is less than the relative density of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution be in solid water not Molten object intensively suspends separation；And it is separated with the aqueous solution of resveratrol glucoside and glucose and sodium chloride or potassium chloride；
(4), the resveratrol glucoside active aglycone of above-mentioned (three) is taken out in conjunction with the mixing of fatty acid or fatty acid ester Object filters moisture therein；It is added in the conjugate of this resveratrol glucoside active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated water for 10-20 times of volume of edible soft water Solution concentration makes the relative density of its aqueous solution be greater than 1；24 hours are stood at 0 DEG C again, makes fatty acid or fatty acid ester in solid Body grease-like intensively suspends separation, and also most aggregate and precipitate is separated from water resveratrol glucoside active aglycone at this time；It obtains containing few Measure the solid resveratrol glucoside active aglycone product of water；Vacuum dehydration is dry again, obtains the production of resveratrol glucoside active aglycone Product；
The relative density of resveratrol glucoside active aglycone is greater than 1.8, much larger than sodium chloride or potassium chloride Nacl/Kcl Saturated aqueous solution relative density；Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester.
According to existing knowledge, the glycosyl in natural glucosides is not limited to glucose, specifically determines glycosyl according to existing knowledge Type, different aglycones and different glycosyls in glucosides do not influence beta-glucosidase to the enzymatic of glycosidic bond in glucosides Hydrolysis.Beta-glucosidase in glucosides different aglycones and different glycosyls do not have (nothing) selectivity.

Claims (3)

1. the highly effective extraction method of natural hydroxyl or/and carboxyl compound, it is characterised in that:
One, the extraction of triterpene saponin:
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants triterpenoid saponin aqueous solution, protect β- The activity of glucuroide；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；Obtain the glycosides of activity containing triterpenoid saponin Member/triterpenoid saponin/glucose aqueous solution contains rouge of the oil-soluble relative density less than 1 dispersed in acidic aqueous solution Fat acid or fatty acid ester impurity, triterpenoid saponin active aglycone are adsorbed by the sour rouge of oleic acid or/and palmitinic acid and are dispersed in suspension within water In solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, low to oleic acid or/and palmitic acid content Triterpenoid saponin aqueous solution the sour rouge of suitable oleic acid or/and palmitinic acid need to be added so that can be completely outstanding in following (three) Triterpenoid saponin active aglycone in floating separation triterpenoid saponin aqueous solution；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the triterpenoid saponin hydrolysis aqueous solution of above-mentioned (one) extremely PH6.8-7；To reduce and overcome dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution, be conducive to make its Aggregation, which suspends, in the salt loading aqueous solution of sodium chloride or potassium chloride separates；Sodium bicarbonate or saleratus NaHCO3/KHCO3It can also It is replaced with part with sodium carbonate or potassium carbonate；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the glycosides of activity containing triterpenoid saponin of above-mentioned (two) Member/triterpenoid saponin/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, at 25 DEG C -50 DEG C When, using the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water as reference value, then should This active aglycone containing triterpenoid saponin/triterpenoid saponin/glucose aqueous solution is added in the sodium chloride or potassium chloride Nacl/Kcl of numerical value Dissolution stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；It further takes out containing triterpenoid saponin activity The aqueous solution of aglycon/triterpenoid saponin/glucose/sodium chloride or potassium chloride；3-8 hours are stood, keeps fatty acid or fatty acid ester miscellaneous Matter sweeps along, adsorbs, the mixing conjugate of the water-insoluble triterpenoid saponin active aglycone of physical bond is because its relative density is less than chlorination The relative density of sodium or potassium chloride Nacl/Kcl saturated aqueous solution and intensively suspend separation in solid water-insoluble；And with triterpene soap The separation of the aqueous solution of glycosides and glucose and sodium chloride or potassium chloride；
(4), the triterpenoid saponin active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester are taken out, it is filtered In moisture；10-20 times of its volume is added in the conjugate of this triterpenoid saponin active aglycone and fatty acid or fatty acid ester again Edible soft water, appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, makes it The relative density of aqueous solution is greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid ester in solid grease Shape intensively suspends separation, and also most aggregate and precipitate is separated from water triterpenoid saponin active aglycone at this time；Obtain the solid containing a small amount of water Triterpenoid saponin active aglycone product；Vacuum dehydration is dry again, obtains triterpenoid saponin active aglycone product；
Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Two, the extraction of flavonoids aglycon
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants flavonoid glycoside aqueous solution, protection The activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains living containing flavonoid glycoside Property aglycon/flavonoid glycoside/glucose aqueous solution, is less than containing the oil-soluble relative density dispersed in acidic aqueous solution 1 fatty acid or fatty acid ester impurity, flavonoid glycoside active aglycone are adsorbed and suspended and divide by the sour rouge of oleic acid or/and palmitinic acid It dissipates in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/and palmitinic acid The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the low flavonoid glycoside aqueous solution of content, so that can be following (three) In the flavonoid glycoside active aglycone that is suspended in separating flavone class glucosides aqueous solution completely；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the flavonoid glycoside hydrolysis aqueous solution of above-mentioned (one) extremely PH6.8-7；To reduce and overcome dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution, be conducive to make its Aggregation, which suspends, in the salt loading aqueous solution of sodium chloride or potassium chloride separates；Sodium bicarbonate or saleratus NaHCO3/KHCO3It can also It is replaced with part with sodium carbonate or potassium carbonate；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the active containing flavonoid glycoside of above-mentioned (two) Aglycon/flavonoid glycoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, 25 DEG C- At 50 DEG C, using the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water as reference value, then This active aglycone containing flavonoid glycoside/flavonoid glycoside/glucose is added in the sodium chloride of the numerical value or potassium chloride Nacl/Kcl Aqueous dissolution, stand 1-3 minute, make excessive sodium chloride or potassium chloride immediately Precipitation separation；It further takes out containing flavones Class glycosidase activity aglycon/flavonoid glycoside/glucose aqueous solution；3-8 hours are stood, fatty acid or fatty acid ester impurity are wrapped up in It holds under the arm, adsorb, the mixing conjugate of the water-insoluble flavonoid glycoside active aglycone of physical bond is because its relative density is less than sodium chloride Or potassium chloride Nacl/Kcl saturated aqueous solution relative density and intensively suspend separation in solid water-insoluble；And it is sugared with flavonoids The separation of the aqueous solution of glycosides and glucose and sodium chloride or potassium chloride；
(4), the flavonoid glycoside active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester, filtering are taken out Moisture therein；Its volume 10-20 is added in the conjugate of this flavonoid glycoside active aglycone and fatty acid or fatty acid ester again Edible soft water again, appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution concentration, The relative density of its aqueous solution is set to be greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid ester in solid Grease-like intensively suspends separation, and also most aggregate and precipitate is separated from water flavonoid glycoside active aglycone at this time；It obtains containing a small amount of water Solid flavonoid glycoside active aglycone product；Vacuum dehydration is dry again, obtains flavonoid glycoside active aglycone product；
Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester；
Three, the extraction of resveratrol aglycon
(1) anti-oxidant with L-cysteine by the beta-glucosidase enzyme hydrolysis of natural plants resveratrol glucoside aqueous solution, it protects Protect the activity of beta-glucosidase；45 DEG C -50 DEG C, PH4.5-5 of hydrolysis temperature, time 24-48 hour；It obtains containing resveratrol sugar Glycosides active aglycone/resveratrol glucoside/glucose aqueous solution, it is oil-soluble relatively close containing what is dispersed in acidic aqueous solution The fatty acid or fatty acid ester impurity less than 1 are spent, resveratrol glucoside active aglycone is adsorbed by the sour rouge of oleic acid or/and palmitinic acid And suspended dispersed is in aqueous solution；Fatty acid or fatty acid ester impurity refer to the sour rouge of oleic acid or/and palmitinic acid, to oleic acid or/ The sour rouge of suitable oleic acid or/and palmitinic acid need to be added in the resveratrol glucoside aqueous solution low with palmitic acid content, so that can Resveratrol glucoside active aglycone in the separation resveratrol glucoside aqueous solution that suspends completely in following (three)；
(2), with sodium bicarbonate or saleratus NaHCO3/KHCO3Neutralize the resveratrol glucoside hydrolysis aqueous solution of above-mentioned (one) To PH6.8-7；To reduce and overcome dispersibility of the sour rouge of oleic acid or/and palmitinic acid in acidic aqueous solution, be conducive to make it Aggregation, which suspends, in the salt loading aqueous solution of sodium chloride or potassium chloride separates；Sodium bicarbonate or saleratus NaHCO3/KHCO3? It can partially be replaced with sodium carbonate or potassium carbonate；
(3), sodium chloride or potassium chloride Nacl/Kcl is added in above-mentioned (two), prepares the living containing resveratrol glucoside of above-mentioned (two) Property aglycon/resveratrol glucoside/glucose aqueous solution salt loading aqueous solution；Specific preparation method, to be energy saving, 25 At DEG C -50 DEG C, using the saturation solubility amount of the sodium chloride or potassium chloride Nacl/Kcl at its a certain temperature in water as reference value, Again by the sodium chloride of the numerical value or potassium chloride Nacl/Kcl be added this active aglycone containing resveratrol glucoside/resveratrol glucoside/ The aqueous dissolution of glucose stands 1-3 minutes, and making excessive sodium chloride or potassium chloride, Precipitation separates immediately；It further takes out The aqueous solution of active aglycone containing resveratrol glucoside/resveratrol glucoside/glucose/sodium chloride or potassium chloride；It is small to stand 3-8 When, so that fatty acid or fatty acid ester impurity are swept along, are adsorbed, the mixing of the water-insoluble resveratrol glucoside active aglycone of physical bond Conjugate because its relative density is less than the relative density of sodium chloride or potassium chloride Nacl/Kcl saturated aqueous solution be in solid water not Molten object intensively suspends separation；And it is separated with the aqueous solution of resveratrol glucoside and glucose and sodium chloride or potassium chloride；
(4), the resveratrol glucoside active aglycone of above-mentioned (three) and the mixing conjugate of fatty acid or fatty acid ester, mistake are taken out Filter moisture therein；Its volume is added in the conjugate of this resveratrol glucoside active aglycone and fatty acid or fatty acid ester again Appropriate sodium chloride or potassium chloride Nacl/Kcl are added at 0 DEG C -5 DEG C or reaches its saturated aqueous solution for 10-20 times of edible soft water Concentration makes the relative density of its aqueous solution be greater than 1；8-24 hours are stood at 0 DEG C -5 DEG C again, makes fatty acid or fatty acid ester is in Solid oil smectic intensively suspends separation, and also most aggregate and precipitate is separated from water resveratrol glucoside active aglycone at this time；Contained The solid resveratrol glucoside active aglycone product of a small amount of water；Vacuum dehydration is dry again, obtains resveratrol glucoside active aglycone Product；
Part recycles in above-mentioned (one) when necessary for fatty acid or fatty acid ester.
2. according to claim 1, the highly effective extraction method of natural hydroxyl or/and carboxyl compound, it is characterised in that: contain Triterpenoid saponin/flavonoids of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Glucosides/resveratrol glucoside acidic aqueous solution is being carbonated hydrogen sodium or saleratus NaHCO3/KHCO3When neutralization, part is specific Active hydroxyl on triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone of kind Base (- OH) or pendant carboxylic group (- COOH) are possible to part and are carbonated hydrogen sodium or saleratus NaHCO3/KHCO3It neutralizes, and makes three Terpene saponin(e active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone generate its corresponding sodium salt or Sylvite, and with triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone while quilt The sour rouge of palmitinic acid sweeps along, adsorbs, physical bond, and suspends and be separated from water.
3. according to claim 1, the highly effective extraction method of natural hydroxyl or/and carboxyl compound, it is characterised in that:
The corresponding sodium salt of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Or sylvite is reduced into the side of triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone Method:
At 5 DEG C -- at 30 DEG C, by triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol of water-insoluble The sodium salt or sylvite of the active aglycone of glucosides are stirred instead with the hydrochloric acid Hcl aqueous solution of slightly excessive mass ratio 10%-30% with it Answer, 300-500 revs/min of mixing speed, make triterpenoid saponin active aglycone/flavonoid glycoside active aglycone of water-insoluble/ The active aglycone sodium salt or sylvite of resveratrol glucoside are sufficiently reacted with hydrochloric acid Hcl aqueous solution；
Generate triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone of hydrogen H reduction Sediment and sodium chloride or potassium chloride aqueous acid；Triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white Chenopodiaceae The sodium salt or sylvite of the active aglycone of reed alcohol glucosides and the feed liquid mass ratio of hydrochloric acid Hcl aqueous solution compare 10-20 for 1；Filtering divides Layer taking-up triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone sediment, then With edible water washing hydrochloric acid therein on a small quantity, the work of precipitation and separation triterpenoid saponin active aglycone/flavonoid glycoside at 1 DEG C -25 DEG C Property aglycon/resveratrol glucoside active aglycone, obtains triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/white Chenopodiaceae The solids of the active aglycone of reed alcohol glucosides；Vacuum dehydration is dry again, obtains the work of triterpenoid saponin active aglycone/flavonoid glycoside Property aglycon/resveratrol glucoside active aglycone product；Active glycosides containing micro triterpenoid saponin active aglycone/flavonoid glycoside The aqueous hydrochloric acid solution of member/resveratrol glucoside active aglycone recycles；The work of triterpenoid saponin active aglycone/flavonoid glycoside Property aglycon/resveratrol glucoside active aglycone is only slightly soluble in hydrochloric acid Hcl aqueous solution, and sodium chloride or potassium chloride Nacl/Kcl can be into One step reduces triterpenoid saponin active aglycone/flavonoid glycoside active aglycone/resveratrol glucoside active aglycone in hydrochloric acid Hcl Solubility in aqueous solution.
CN201810388778.2A 2018-04-12 2018-04-12 The highly effective extraction method of natural hydroxyl or/and carboxyl compound Pending CN110372770A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102094052A (en) * 2010-12-12 2011-06-15 大连理工大学 Method for preparing natural medicines by coupling glycosidase catalysis and salting-out extraction
CN102492731A (en) * 2011-12-12 2012-06-13 重庆大学 Method for preparing resveratrol by utilizing immobilized enzyme to continuously hydrolyze polydatin
CN102503756A (en) * 2011-10-28 2012-06-20 耿兆翔 Method for extracting natural compound containing hydroxyl or/and carboxyl
CN102559642A (en) * 2012-01-19 2012-07-11 杭州师范大学 Beta-glucosidase, coding gene, carrier and application thereof
CN102747116A (en) * 2012-06-12 2012-10-24 山东东兴生物科技股份有限公司 Production technology for extracting soybean isoflavone aglycone through enzymatic hydrolysis method
CN104059951A (en) * 2013-03-18 2014-09-24 耿兆翔 Extraction method of natural anthocyanidin active aglycone

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102094052A (en) * 2010-12-12 2011-06-15 大连理工大学 Method for preparing natural medicines by coupling glycosidase catalysis and salting-out extraction
CN102503756A (en) * 2011-10-28 2012-06-20 耿兆翔 Method for extracting natural compound containing hydroxyl or/and carboxyl
CN102977179A (en) * 2011-10-28 2013-03-20 耿兆翔 Method for extracting hydroxy group or/and carboxyl group contained natural compounds
CN102492731A (en) * 2011-12-12 2012-06-13 重庆大学 Method for preparing resveratrol by utilizing immobilized enzyme to continuously hydrolyze polydatin
CN102559642A (en) * 2012-01-19 2012-07-11 杭州师范大学 Beta-glucosidase, coding gene, carrier and application thereof
CN102747116A (en) * 2012-06-12 2012-10-24 山东东兴生物科技股份有限公司 Production technology for extracting soybean isoflavone aglycone through enzymatic hydrolysis method
CN104059951A (en) * 2013-03-18 2014-09-24 耿兆翔 Extraction method of natural anthocyanidin active aglycone

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