CN1793136A - Process for producing kuh-seng total flavone and flavone salt - Google Patents
Process for producing kuh-seng total flavone and flavone salt Download PDFInfo
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- CN1793136A CN1793136A CN 200510048249 CN200510048249A CN1793136A CN 1793136 A CN1793136 A CN 1793136A CN 200510048249 CN200510048249 CN 200510048249 CN 200510048249 A CN200510048249 A CN 200510048249A CN 1793136 A CN1793136 A CN 1793136A
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Abstract
The invention relates to a method to produce kuhseng omniflavone and flavone salt that mixes kuh-seng and acid water as 1: 5-10 at 10-40 degree centigrade, fully distills biology alkali, filtering, mixing the residue with solvent according 1g: 4-12ml, distilling, filtering, the filtrate could be treated to gain kuhseng omniflavone and flavone. The invention has advantages of low cost raw material, simple technology, etc.
Description
Technical field
The present invention relates to a kind of method of producing kuh-seng total flavone and flavone salt.
Technical background
Flavonoid compound is the class natural product that nature extensively exists, its basic parent nucleus is 2-phenyl chromogen ketone, refer to that two phenyl ring (A, B ring) with phenolic hydroxyl group interconnect a series of compounds that form by 3 carbon atoms of central authorities, difference according to central 3 carbochains, can be divided into flavonoid, flavonols, flavanone, flavanone alcohols, anthocyan, chalcone, dihydrochalcone-like, osajin, isoflavanone class or the like, experimental results show that flavonoids to animal and human body have following effect 1. anti-oxidant, remove the free radical effect; 2. vitamins C there is synergism; 3. by protection cellular immunization, avoid carcinogenic infringement, suppress tumor cell proliferation and anti-radical action and the tool antitumous effect; 4. can with metal-chelating, the activity of protective enzyme and cytolemma; 5. can blood fat reducing and blood cholesterol; 6. isoflavones has the estrogenic effect of class; 7. hepatoprotective effect.Flavones such as propolis, ginkgo, sea-buckthorn are succeedd on market.
Kuh-seng is rich in alkaloids and flavonoid composition, present research mainly concentrates on the Radix Sophorae Flavescentis alkaloid aspect, and from existing 32 kinds of the isolating flavonoid compound of radix sophorae, majority is flavanone and flavanone alcohols, minority is flavonoid, flavonols, osajin, chalcone and polycyclic system flavonoid, comprises kuh-seng alcohol A, B, D, E, F, J or the like.There is the isopentene substituting group to exist on the kuh-seng flavone A ring, and most of flavones substituting group on the C8 position of A ring exists with the branch isopentene group side chain form of lavandulyl, the isopentene groupization of flavones has increased the lipotropy of chromocor compound, make its easier in vivo permeate through cell membranes arrival effect target, thereby isoamylene radical chromocor has stronger antimicrobial acivity, anti-inflammatory activity, antitumour activity and tyrosinase inhibitory activity (research and development of natural products, 2004,16 (2): 172).The kuh-seng flavone extract has obvious blood sugar reducing function to Alloxan diabetes model rat, and alkaloid does not have blood sugar reducing function (Strait Pharmaceutical Journal magazine, 1998,10 (1): 9), the report of relevant Radix Sophorae Flavescentis alkaloid extraction separation is a lot, high red peaceful grade (ACAD J GCP, 2003,19 (4): 334) by refining Oxymatyine of micro-filtration, macroporous resin, alcohol precipitation and kuh-seng total flavone, but the separating of be unrealized alkaloid and flavones; Patent (200410030937.X) provides a kind of extracting method of kuh-seng total flavone, but, the contents separated and the step that do not relate to Radix Sophorae Flavescentis alkaloid class and flavonoids effective constituent in this method, resulting product should be the mix product of Radix Sophorae Flavescentis alkaloid and kuh-seng flavonoid.The rarely seen report of extraction separation of relevant kuh-seng isoamylene radical chromocor class.
The flavone salt product has the biological activity with flavones, and chemical property is relatively stable, can with the alkaline drug compatibility, be easy to advantages such as preservation, relevant its product or production technique are not appeared in the newspapers as yet.
Summary of the invention
The purpose of this invention is to provide a kind of method of producing kuh-seng total flavone and flavone salt.
The present invention be since Radix Sophorae Flavescentis alkaloid in plant materials and various organic acids in conjunction with forming salt, with sour water alkaloid is extracted fully, and the flavonoid active substance is to be insoluble to sour water, is retained in the plant materials.The kuh-seng Flavonoid substances is soluble in alcohol, ester, ketone and buck equal solvent, can extract with alcohol, ester, ketone and buck equal solvent and obtain higher kuh-seng total flavone of content and flavone salt product.
Concrete operations step of the present invention is as follows:
(1), be that 10～120 purpose kuh-sengs are that raw material mixes with 1: 5～10 part by weight with sour water with granularity, at 10～40 ℃, extract Radix Sophorae Flavescentis alkaloid fully, filter, the filtrate preparation Radix Sophorae Flavescentis alkaloid that is used for purifying, filter residue is drained;
(2), (1) gained filter residue and solvent are pressed 1g: the mixed of 4～12ml, extract, to filter, filtrate obtains 80% kuh-seng total flavone or flavone salt product through handling.
Can be any acidic aqueous solution as sour water as described in (1), preferred hydrochloric acid, sulfuric acid, acetic acid or aqueous nitric acid, the pH value of sour water is good with 2～6.
Can be as acid extraction alkaloid as described in (1) by any methods that alkaloid can be extracted fully such as immersion, diacolation, supersound extraction.
As solvent as described in (2) is anyly can dissolve flavones solvent or solution, preferred lower alcohol, lower member ester, lower ketones, ethers and the mixing solutions of above-mentioned any solvent or the aqueous solution solution of alkali.The mixing solutions of particular methanol, ethanol, ethyl acetate, methyl acetate, acetone, ether and above-mentioned any solvent.Any concentration of aqueous solution of the preferred sodium hydroxide of the aqueous solution of alkali, potassium hydroxide, yellow soda ash, sodium bicarbonate etc.The preferred pH value of the aqueous solution of alkali is 9～14 solution, and preferred pH value is 9～11 solution.
Processing as filtrate process as described in (2) has two kinds of methods:
Method one: if extract the solvent that the kuh-seng flavones uses is the aqueous solution of alkali, then extracting solution can be added acid to pH value and be neutrality, and solid-liquid separation then, solid drying promptly gets the kuh-seng total flavone pressed powder;
The processing of described filtrate process also can be directly the filtrate drying to be obtained the salt of kuh-seng total flavone as the finished product.
Described acid can be any water-soluble organic acid or mineral acid, preferred hydrochloric acid, sulfuric acid, nitric acid or acetic acid etc.
Described solid-liquid separation can be any with the isolating technology of solid-liquid two-phase, preferably filters or centrifugation.
Described dry preferably spray drying, underpressure distillation, vacuum lyophilization, flash distillation or spontaneous evaporation are dried.
Method two: if extracting solution is any above-mentioned solution or solvent except that the aqueous solution of alkali, can be with solvent recuperation, drying obtains the kuh-seng total flavone pressed powder then.
Described dry spraying drying, vacuum lyophilization, flash distillation or spontaneous evaporation.
The kuh-seng total flavone that the present invention extracts preparation can be made into various forms of products, as the salt series products of powder, various kuh-seng flavonoids solution and kuh-seng total flavone.
Advantage of the present invention is as follows:
1, the substituting group that all has the branch isopentene group side chain form with lavandulyl to exist on the C8 position of the most of A of kuh-seng flavones ingredient ring, this is that the kuh-seng flavonoid is exclusive, is to be different from the key character that extracts flavonoid.
2, described lavandulyl branch isopentene group side chain increases the lipotropy of flavones, make its easier in vivo permeate through cell membranes arrival effect target, thereby kuh-seng total flavone have stronger antimicrobial acivity, anti-inflammatory activity, antitumour activity and tyrosinase inhibitory activity than other flavones.
3, realize first extracting Radix Sophorae Flavescentis alkaloid and kuh-seng flavones respectively, do not contained the kuh-seng total flavone class and its esters product of Radix Sophorae Flavescentis alkaloid first.
4, the kuh-seng residue behind the employing extraction matrine is raw material production kuh-seng total flavone and its esters product, and raw materials cost is low, and technology is simple, is fit to industrial production.
5, kuh-seng total flavone that obtains and its esters product content are higher, and the total flavones product is the yellow solid powder, and total flavones salt series products is the reddish-brown solid crystal.
Embodiment
Embodiment 1:
(1) 10～40 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 600ml of pH=3, and 10 ℃ of supersound extraction 30min leave standstill, and filters, and filter residue washs to lifeless matter alkali with above-mentioned hydrochloric acid soln; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) add the ultrasonic extract at room temperature of 500ml ethanol with filtering the filter cake that obtains in (1), 30min filters, and filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, the decompression rotary evaporation obtains the yellow powder product, contains total flavones 80% (UV) after testing.
Embodiment 2:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous acetic acid 500ml of pH=5, and 20 ℃ were soaked 6 hours, left standstill, and filtered, and filter residue washs to lifeless matter alkali with above-mentioned hydrochloric acid soln; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) add 400ml methyl alcohol and soaked 6 hours filtering the filter cake that obtains in (1), filter, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, spontaneous evaporation is dried, and obtains the yellow powder product, contains total flavones 82% (UV) after testing.
Embodiment 3:
(1) 80～120 purpose Lightyellow Sophora Root 100g is extracted into extracting solution lifeless matter alkali with 30 ℃ of diacolations of aqueous sulfuric acid of pH=4; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) added the 500ml ethyl acetate backflow 2 hours with filtering the filter cake that obtains in (1), filter, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, vacuum lyophilization obtains the yellow powder product, contains total flavones 89% (UV) after testing.
Embodiment 4:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous nitric acid 1000ml of pH=6, and 40 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) with filter in (1) filter cake that obtains add 500ml ethyl acetate and alcoholic acid mixed solution (1: 1, V/V) soaked 6 hours, filter, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, flash distillation obtains the yellow powder product, contains total flavones 88% (UV) after testing.
Embodiment 5:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=2, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) with filter in (1) filter cake that obtains add 500ml acetone and alcoholic acid mixed solution (1: 1, V/V) soaked 6 hours, filter, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, decompression steam and slip, and obtain the yellow powder product, contain total flavones 85% (UV) after testing.
Embodiment 6:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) with filter in (1) mixed solution that the filter cake that obtains adds 500ml acetone and ether (1: 1, V/V) refluxed 2 hours, filter, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, spontaneous evaporation is dried, and obtains the yellow powder product, contains total flavones 86% after testing.
Embodiment 7:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) with filter in (1) mixed solution that the filter cake that obtains adds 500ml methyl acetate and methyl alcohol (3: 1, V/V) supersound extraction is filtered, filter cake repeats to extract, is filtered to that extracting solution does not have yellow or color and luster is very shallow; United extraction liquid, vacuum lyophilization obtains the yellow powder product, contains total flavones 84% after testing.
Embodiment 8:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous acetic acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) add aqueous sodium hydroxide solution (pH=9) supersound extraction with filtering the filter cake that obtains in (1), filter, filter cake repeats to extract, be filtered to extracting liquid colourless or color and luster is very shallow; United extraction liquid, spraying drying obtains the reddish-brown powder-product.
Embodiment 9:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) the filter cake usefulness sodium bicarbonate aqueous solution (pH=10) percolate that filtration in (1) is obtained is colourless or color and luster is very shallow; United extraction liquid, spontaneous evaporation is dried, and obtains the reddish-brown powder-product.
Embodiment 10:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) the filter cake usefulness sodium bicarbonate aqueous solution (pH=10) percolate that filtration in (1) is obtained is colourless or color and luster is very shallow; United extraction liquid adds hydrochloric acid and is neutralized to neutrality, filters, and the filter cake spontaneous evaporation is dried, and obtains yellow toner end product, contains total flavones 81% after testing.
Embodiment 11:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) filter cake usefulness potassium hydroxide aqueous solution (pH=12) percolate that filtration in (1) is obtained is colourless or color and luster is very shallow; United extraction liquid adds acetic acid and is neutralized to neutrality, filters, and the filter cake vacuum lyophilization obtains yellow toner end product, contains total flavones 82% after testing.
Embodiment 12:
(1) 40～80 purpose Lightyellow Sophora Root 100g adds the aqueous hydrochloric acid 400ml of pH=3, and 30 ℃ of supersound extraction are to extracting solution lifeless matter alkali; Filter, filtrate can obtain various Radix Sophorae Flavescentis alkaloid products through handling.
(2) filter cake usefulness aqueous sodium carbonate (pH=10) percolate that filtration in (1) is obtained is colourless or color and luster is very shallow; United extraction liquid adds acetic acid and is neutralized to neutrality, filters, and the filter cake vacuum lyophilization obtains yellow toner end product, contains total flavones 80% after testing.
Claims (14)
1, a kind of method of producing kuh-seng total flavone and flavone salt, it is characterized in that comprising the steps: that (1) is that 10～120 purpose kuh-sengs are that raw material mixes with 1: 5～10 part by weight with sour water with granularity, at 10～40 ℃, extract Radix Sophorae Flavescentis alkaloid fully, filter, filtrate is used for purifying and prepares Radix Sophorae Flavescentis alkaloid, and filter residue is drained;
(2) (1) gained filter residue and solvent are pressed 1g: the mixed of 4～12ml, extract, to filter, filtrate obtains kuh-seng total flavone or flavone salt product through handling.
2, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 1 is characterized in that as sour water as described in (1) be acidic aqueous solution.
3, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 2 is characterized in that described acidic aqueous solution is hydrochloric acid, sulfuric acid, acetic acid or aqueous nitric acid, and the pH value of sour water is 2～6.
4, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 1, it is characterized in that as solvent as described in (2) be lower alcohol, lower member ester, lower ketones, ethers with and the aqueous solution of mixing solutions or alkali.
5, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 4 is characterized in that described solvent is methyl alcohol, ethanol, ethyl acetate, methyl acetate, acetone, ether or its mixing solutions.
6, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 4, the aqueous solution that it is characterized in that described alkali is the aqueous solution of sodium hydroxide, potassium hydroxide, yellow soda ash or sodium bicarbonate, the pH value is 9～14.
7, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 4 is characterized in that described pH value is 9～11.
8, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 1 is characterized in that being treated to as filtrate process as described in (2):
If extracting the solvent that the kuh-seng flavones uses is the aqueous solution of alkali, extracting solution is added acid to pH value be neutrality, solid-liquid separation then, solid drying promptly gets the kuh-seng total flavone pressed powder.
9, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 8 is characterized in that described acid is any water-soluble organic acid or mineral acid.
10, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 9 is characterized in that described acid is hydrochloric acid, sulfuric acid, nitric acid or acetic acid.
11, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 8 is characterized in that described solid-liquid separation is to filter or centrifugation.
12, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 8 is characterized in that described dry preferably spray drying, underpressure distillation, vacuum lyophilization, flash distillation or spontaneous evaporation dry.
13, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 1, it is characterized in that being treated to as filtrate process as described in (2): if extract the solvent that the kuh-seng flavones uses is the aqueous solution of alkali, directly the filtrate drying is obtained the salt of kuh-seng total flavone.
14, a kind of method of producing kuh-seng total flavone and flavone salt as claimed in claim 1, it is characterized in that described being treated to: if when extracting solution is lower alcohol, lower member ester, lower ketones or ethers as filtrate process as described in (2), with solvent recuperation, drying obtains the kuh-seng total flavone pressed powder then.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101084989B (en) * | 2007-07-11 | 2010-09-29 | 石任兵 | Method for preparing general flavone and total alkaloid of sophora flavescens simultaneously |
| CN102649802A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Preparation method of trifolirhizin |
| CN103070912A (en) * | 2012-11-19 | 2013-05-01 | 北京振东光明药物研究院有限公司 | Sophora flavescens totall flavone extract product, preparation method and quality detection method |
| CN110256431A (en) * | 2019-07-16 | 2019-09-20 | 山东花物堂生物科技有限公司 | The extraction of biology total alkali and separation purifying technique in a kind of kuh-seng |
| CN110840928A (en) * | 2019-11-29 | 2020-02-28 | 广东药科大学 | Application of total flavonoids of sophora flavescens in preparing medicine for treating ulcerative colitis |
| CN111514205A (en) * | 2020-05-21 | 2020-08-11 | 上海珈凯生物科技有限公司 | Combined extraction method and application of total flavonoids and total alkaloids in pericarpium citri reticulatae viride |
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| CN109820887B (en) * | 2019-04-16 | 2021-08-10 | 荆楚理工学院 | Composition with function of treating beriberi and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10031651A1 (en) * | 2000-06-29 | 2002-01-17 | Schwabe Willmar Gmbh & Co | Extracts from Sophora species, process for their preparation and use |
| CN1172933C (en) * | 2003-05-22 | 2004-10-27 | 王答祺 | Prepn of matrine, oxymatrine and sophoxidine from flavescent sophora root |
| CN1676520A (en) * | 2004-04-01 | 2005-10-05 | 和记黄埔医药企业有限公司 | Kuh-seng flavone extract and preparation and use thereof |
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2005
- 2005-12-27 CN CNB2005100482490A patent/CN100528856C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101084989B (en) * | 2007-07-11 | 2010-09-29 | 石任兵 | Method for preparing general flavone and total alkaloid of sophora flavescens simultaneously |
| CN102649802A (en) * | 2011-02-25 | 2012-08-29 | 苏州宝泽堂医药科技有限公司 | Preparation method of trifolirhizin |
| CN103070912A (en) * | 2012-11-19 | 2013-05-01 | 北京振东光明药物研究院有限公司 | Sophora flavescens totall flavone extract product, preparation method and quality detection method |
| CN110256431A (en) * | 2019-07-16 | 2019-09-20 | 山东花物堂生物科技有限公司 | The extraction of biology total alkali and separation purifying technique in a kind of kuh-seng |
| CN110840928A (en) * | 2019-11-29 | 2020-02-28 | 广东药科大学 | Application of total flavonoids of sophora flavescens in preparing medicine for treating ulcerative colitis |
| CN111514205A (en) * | 2020-05-21 | 2020-08-11 | 上海珈凯生物科技有限公司 | Combined extraction method and application of total flavonoids and total alkaloids in pericarpium citri reticulatae viride |
| CN111514205B (en) * | 2020-05-21 | 2022-03-25 | 上海珈凯生物科技有限公司 | Combined extraction method and application of total flavonoids and total alkaloids in pericarpium citri reticulatae viride |
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