CN101948496A - Method for extracting chenodeoxycholic acid from bile of fowl - Google Patents
Method for extracting chenodeoxycholic acid from bile of fowl Download PDFInfo
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Abstract
A method for extracting chenodeoxycholic acid from bile of fowl comprises the following steps of: acquiring rough bile acid or rough bile acid calcium salt from fresh or frozen bile of fowl through saponification reaction, heating the bile acid resin solution together with the aqueous solution of organic nitrogenous compound A, removing the majority of hydrophilic impurities from the rough bile acid by using the organic nitrogenous compound A, reacting the acquired bile acid resin solution with organic nitrogenous compound B, dissolving the sediment, filtering, decolorizing and refining, so as to acquire chenodeoxycholic acid with a purity about 95%. The method of the invention has simple operation, the generality of the production equipment is high, and the chemic matter is harmless, therefore the invention is fit for industrialization of chenodeoxycholic acid.
Description
Technical field
The present invention relates to cholic acid class extracting method, relate in particular to a kind of Chenodiol (3 α, 7 alpha-dihydroxy-s-5 β-ursodeoxycholic acid, abbreviation: method CDCA) of from poultry bile, extracting.
Background technology
Chenodiol has the effect that reduces bile inner cholesterol saturation ratio, thereby gall stone is had better therapeutic effect.Chenodiol also is that (3 α, 7 beta-dihydroxyies-5 β-ursodeoxycholic acid are called for short: important source material UDCA) the synthetic ursodesoxycholic acid of chemical method; Ursodesoxycholic acid is the main effective constituent in the bear gall bile, and multiple diseases such as liver, courage are had clear and definite curative effect.
Extracting Chenodiol from poultry bile, is the main path of present industrial production Chenodiol.It is complicated that the extracting method of having reported generally has process, and used chemical substance toxicity is bigger, produces characteristics such as environmental pollution, makes Chenodiol under the technical scale working condition, and efficient is comparatively low.
Summary of the invention
A kind of method of extracting Chenodiol from poultry bile is utilized cheap, that security is higher nitrogenous compound A, B, removes wetting ability contained in the thick bile acide and lipotropy impurity respectively; Compare with the extracting method of having reported, have Device-General, easy and simple to handle, characteristics such as cost is lower.
Technical scheme of the present invention is as follows:
(1) preparation of thick bile acide or thick bile acide calcium salt
Get fresh or frozen chicken bile or other poultry bile, 1～2/10 amount (W/V) of pressing the bile volume adds industrial sodium hydroxide, heated and boiled 12～24 hours, saponification, cooling.Handle by following method respectively, can get thick bile acide or thick bile salt.
1. the preparation of thick bile acide: saponification liquor is transferred pH2～3 with 1: 1 (V/V) hydrochloric acid, get thick bile acide; The place is air-dry in the cool place.
2. the preparation of thick bile acide calcium salt: 15～25% amounts (W/V) of saponification liquor being pressed the bile volume add industrial calcium chloride, react 2～3 hours, filter, and get thick bile acide calcium precipitation, drying.
(2) preliminary decolouring with remove impurity such as cholic acid
1. get in the vinyl acetic monomer that thick bile acide joins 5 to 15 times of amounts, add saturated nacl aqueous solution again with 0.5～1 times of amount of vinyl acetic monomer volume; Dissolving; Add the gac that is equivalent to thick bile acide weight 0.5～2%; 30～60 ℃, stirred 1～3 hour, place elimination breeze, branch vibration layer.The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 5～20%, concentration 10～50%.40～90 ℃, stirred 5～10 hours; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%.
2. get in the vinyl acetic monomer that thick bile acide joins 5 to 15 times of amounts, add saturated nacl aqueous solution again with 0.5～1 times of amount of vinyl acetic monomer volume; Dissolving; Add the diatomite that is equivalent to thick bile acide weight 2～3%; 30～60 ℃, stirred 1～3 hour, place, after supernatant liquid is told, leave standstill branch vibration layer.The ester layer adds the gac that is equivalent to thick bile acide weight 0.2～1%; 30～60 ℃, stirred 0.5～1 hour, place elimination breeze, branch vibration layer.The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 5～20%, concentration 10～50%.40～90 ℃, stirred 5～10 hours; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%.
3. get thick bile acide calcium salt to 5 to the water of 10 times of amounts; Transfer pH2～3 with 1: 1 (V/V) hydrochloric acid, add isopyknic vinyl acetic monomer, branch vibration layer; After the ester layer is washed till nearly neutrality with saturated nacl aqueous solution, add the gac that is equivalent to thick bile acide weight of calcium salt 0.5～2%; 30～60 ℃, stirred 1～3 hour, place the elimination breeze; The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 5～20%, concentration 10～50%.40～90 ℃, stirred 5～10 hours; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%.
(3) remove oil-soluble impurities
In the ester layer of aforementioned gained, add suitably excessive organic compounds containing nitrogen B of mole number; 20～60 ℃, to stir 2～6 hours, cooling is placed, and filters; Filter cake washs with the little acetic acid ethyl ester, and drying gets powdery solid.Analyze the oil-soluble impurities clearance about 85～95%.
(4) Chenodiol is free and refining
1. the solid with aforementioned gained joins 1～5: in the mixed system of 1 (V/V) vinyl acetic monomer-water; 30～70 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B, continue at 30～70 ℃, stirred 1～4 hour; Cooling, branch vibration layer; The ester layer adds 0.1～2% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer is separated out Chenodiol (CDCA) crystallization; This crystallization changed in No. 120 an amount of gasoline soaked 6～10 hours; Filter 45～55 ℃ of vacuum-dryings; Get purity about 95%, the CDCA crystallization of fusing point 135～145 ℃ (capillary tube techniques).
2. the solid with aforementioned gained joins 1～5: in the mixed system of 1 (V/V) vinyl acetic monomer-water; 30～70 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B, continue at 30～70 ℃, stirred 1～4 hour; Cooling, branch vibration layer; The ester layer adds 0.1～2% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer slowly adds No. 120 an amount of gasoline to about 60% of add-on, separates out Chenodiol (CDCA) crystallization; Growing the grain 6～10 hours; Filter 45～55 ℃ of vacuum-dryings; Get purity about 95%, the CDCA crystallization of fusing point 135～145 ℃ (capillary tube techniques).
Beneficial effect:
The present invention in the quality that does not influence Chenodiol, have easy and simple to handle, production unit versatility height, the characteristics of used chemical substance low toxicity are convenient to large-scale promotion and are used.
Embodiment
Below by specific embodiment present method is described further
Embodiment 1: get fresh or frozen chicken bile or other poultry bile, by 1/10 amount (W/V) adding industrial sodium hydroxide of its volume, heated and boiled 16 hours after the saponification fully, is cooled to room temperature, adds 1: 1 (V/V) hydrochloric acid and transfers pH2, separates out thick bile acide; The clear water washing is dried in the shade.
Thick bile acide is joined in the vinyl acetic monomer of 10 times of amounts, add and the isopyknic saturated nacl aqueous solution of vinyl acetic monomer; Dissolving is by the gac of thick bile acide weight 1%; 35 ℃, stirred 2 hours, place elimination breeze, branch vibration layer.The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 10%, concentration 20%.60 ℃, stirred 8 hours; Branch vibration layer is placed in cooling; Ester layer thin layer chromatography analysis, hydrophilic impurities cholic acid (CA) etc. can be removed major part.
Getting the suitable excessive organic compounds containing nitrogen B of mole number joins in the aforementioned ester layer; 40 ℃, to stir 4 hours, cooling separates; Filter cake washs with an amount of vinyl acetic monomer, and drying gets light powdery solid.
Aforementioned solid is joined in the mixed system of 2: 1 (V/V) vinyl acetic monomer-water; 40 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B (ratio of A and B is 1: 3), stirs 2 hours; Cooling, branch vibration layer; The ester layer adds 1% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer is separated out Chenodiol (CDCA) crystallization; This crystallization is changed over to soaked overnight in No. 120 gasoline of 10 times of amounts (W/V), growing the grain filters 50 ℃ of vacuum-dryings; Get the Chenodiol finished product, purity 95%, 145 ℃ of fusing points.
Embodiment 2: get fresh or frozen chicken bile or other poultry bile, by 1/10 amount (W/V) adding industrial sodium hydroxide of its volume, about 16 hours of heated and boiled after the saponification fully, is cooled to room temperature; 20% amount (W/V) of saponification liquor being pressed the bile volume adds industrial calcium chloride, reacts 3 hours, filters collecting precipitation, drying.
Get in the water of thick bile acide calcium salt to 8 times amount; Transfer pH2 with 1: 1 (V/V) hydrochloric acid, add isopyknic vinyl acetic monomer, branch vibration layer; After the ester layer is washed till nearly neutrality with saturated nacl aqueous solution, add the gac that is equivalent to thick bile salt weight 1%; 45 ℃, stirred 1.5 hours, place the elimination breeze; The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 20%, concentration 15%.65 ℃, stirred 6 hours; Branch vibration layer is placed in cooling; Ester layer thin layer chromatography analysis, hydrophilic impurities cholic acid (CA) removes 4/5.
Getting the suitable excessive organic compounds containing nitrogen B of mole number joins in the aforementioned ester layer; 30 ℃, stirred 5 hours, separate; Filter cake washs with an amount of vinyl acetic monomer, and drying gets light powdery solid.
The solid of aforementioned gained is joined in the mixed system of 3: 1 (V/V) vinyl acetic monomer-water; 50 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B (ratio of A and B is 1: 3), stirs 3 hours; Cooling, branch vibration layer; The ester layer adds 0.5% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer is separated out Chenodiol (CDCA) crystallization; This crystallization is changed over to soaked overnight in No. 120 gasoline of 8 times of amounts (W/V), growing the grain filters 50 ℃ of vacuum-dryings; Get Chenodiol (CDCA) finished product, purity 95%, 140 ℃ of fusing points.
Embodiment 3: get fresh or frozen chicken bile or other poultry bile, by 1/10 amount (W/V) adding industrial sodium hydroxide of its volume, about 16 hours of heated and boiled after the saponification fully, is cooled to room temperature, adds 1: 1 (V/V) hydrochloric acid and transfers pH2, separates out thick bile acide; The clear water washing is dried in the shade.
Get in the vinyl acetic monomer that thick bile acide joins 12 times of amounts, add saturated nacl aqueous solution with 0.5 times of amount of vinyl acetic monomer volume; Dissolving; Add the diatomite that is equivalent to thick bile acide weight 3%; 55 ℃, stirred 3 hours, place, after supernatant liquid is told, leave standstill branch vibration layer.The ester layer adds the gac that is equivalent to thick bile acide weight 0.5%; 50 ℃, stirred 1 hour, place elimination breeze, branch vibration layer.The aqueous solution that in the ester layer, adds the organic compounds containing nitrogen A of suitable ester layer volume 15%, concentration 30%.55 ℃, stirred 10 hours; Branch vibration layer is placed in cooling; Ester layer thin layer chromatography analysis, hydrophilic impurities cholic acid (CA) removes 80%.
Getting the suitable excessive organic compounds containing nitrogen B of mole number joins in the aforementioned ester layer; 40 ℃, to stir 4 hours, cooling separates; Filter cake washs with an amount of vinyl acetic monomer, and drying gets light powdery solid.
The solid of aforementioned gained is joined in the mixed system of 2: 1 (V/V) vinyl acetic monomer-water; 70 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B, stirs 2 hours; Cooling, branch vibration layer; The ester layer adds 0.5% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer slowly adds No. 120 an amount of gasoline to about 60% of add-on, separates out Chenodiol (CDCA) crystallization; Growing the grain 10 hours; Filter 50 ℃ of vacuum-dryings; Get purity 95%, the CDCA crystallization that fusing point is 145 ℃.
More than show and described ultimate principle of the present invention and principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; that describes in the foregoing description and the specification sheets just illustrates principle of the present invention; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the claimed scope of the invention.The claimed scope of the present invention is defined by appending claims and equivalent thereof.
Claims (1)
1. a method of extracting Chenodiol from poultry bile is characterized in that nitrogenous compound A, B remove wetting ability contained in the thick bile acide and lipotropy impurity respectively, obtain the finished product of Chenodiol, and its concrete grammar comprises:
(1) preparation of thick bile acide or thick bile acide calcium salt
Get fresh or frozen chicken bile or other poultry bile, 1～2/10 amount (W/V) of pressing the bile volume adds industrial sodium hydroxide, heated and boiled 12～24 hours, and saponification, cooling is handled by following method respectively, can get thick bile acide or thick bile salt,
1. the preparation of thick bile acide: saponification liquor is transferred pH2～3 with 1: 1 (V/V) hydrochloric acid, get thick bile acide; The place is air-dry in the cool place,
2. the preparation of thick bile acide calcium salt: 15～25% amounts (W/V) of saponification liquor being pressed the bile volume add industrial calcium chloride, react 2～3 hours, filter, and get thick bile acide calcium precipitation, drying;
(2) preliminary decolouring with remove impurity such as cholic acid
1. get in the vinyl acetic monomer that thick bile acide joins 5 to 15 times of amounts, add saturated nacl aqueous solution again with 0.5～1 times of amount of vinyl acetic monomer; Dissolving; Add the gac that is equivalent to thick bile acide weight 0.5～2%; 30～60 ℃, stirred 1～3 hour, place, the elimination breeze, branch vibration layer, the aqueous solution of the organic compounds containing nitrogen A of the suitable ester layer volume 5～20% of adding, concentration 10～50%, stirred 5～10 hours by 40～90 ℃ in the ester layer; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%;
2. get in the vinyl acetic monomer that thick bile acide joins 5 to 15 times of amounts, add saturated nacl aqueous solution again with 0.5～1 times of amount of vinyl acetic monomer volume; Dissolving; Add the diatomite that is equivalent to thick bile acide weight 2～3%; 30～60 ℃, stirred 1～3 hour, place, after supernatant liquid is told, leave standstill, branch vibration layer, the ester layer adds the gac that is equivalent to thick bile acide weight 0.2～1%; 30～60 ℃, stirred 0.5～1 hour, place, the elimination breeze, branch vibration layer, the aqueous solution of the organic compounds containing nitrogen A of the suitable ester layer volume 5～20% of adding, concentration 10～50%, stirred 5～10 hours by 40～90 ℃ in the ester layer; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%;
3. get thick bile acide calcium salt to 5 to the water of 10 times of amounts; Transfer pH2～3 with 1: 1 (V/V) hydrochloric acid, add isopyknic vinyl acetic monomer, branch vibration layer; After the ester layer is washed till nearly neutrality with saturated nacl aqueous solution, add the gac that is equivalent to thick bile acide weight of calcium salt 0.5～2%; 30～60 ℃, stirred 1～3 hour, place the elimination breeze; In the ester layer, add the aqueous solution of the organic compounds containing nitrogen A of suitable ester layer volume 5～20%, concentration 10～50%, 40～90 ℃, stirred 5～10 hours; Branch vibration layer is placed in cooling; To ester layer analysis cholic acid (3 α, 7 α, 12 α-trihydroxy--5 β-ursodeoxycholic acid, be called for short: CA) content, its clearance is about 75～85%;
(3) remove oil-soluble impurities
In the ester layer of aforementioned gained, add suitably excessive organic compounds containing nitrogen B of mole number; 20～60 ℃, to stir 2～6 hours, cooling is placed, and filters; Filter cake washs with the little acetic acid ethyl ester, and drying gets powdery solid, analyzes the oil-soluble impurities clearance about 85～95%;
(4) Chenodiol is free and refining
1. the solid with aforementioned gained joins 1～5: in the mixed system of 1 (V/V) vinyl acetic monomer-water; 30～70 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B, continue at 30～70 ℃, stirred 1～4 hour; Cooling, branch vibration layer; The ester layer adds 0.1～2% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer is separated out Chenodiol (CDCA) crystallization; This crystallization changed in No. 120 an amount of gasoline soaked 6～10 hours; Filter 45～55 ℃ of vacuum-dryings; Get purity about 95%, the CDCA crystallization of fusing point 135～145 ℃ (capillary tube techniques);
2. the solid with aforementioned gained joins 1～5: in the mixed system of 1 (V/V) vinyl acetic monomer-water; 30～70 ℃, stir, treat that solid dissolving back adds an amount of organic compounds containing nitrogen A and organic compounds containing nitrogen B, continue at 30～70 ℃, stirred 1～4 hour; Cooling, branch vibration layer; The ester layer adds 0.1～2% activated carbon decolorizing; The reclaim under reduced pressure vinyl acetic monomer slowly adds No. 120 an amount of gasoline to about 60% of add-on, separates out Chenodiol (CDCA) crystallization; Growing the grain 6～10 hours; Filter 45～55 ℃ of vacuum-dryings; Get purity about 95%, the CDCA crystallization of fusing point 135～145 ℃ (capillary tube techniques).
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Cited By (10)
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| CN102453071A (en) * | 2010-10-23 | 2012-05-16 | 毕思宾 | Method for preparing chenodeoxycholic acid and ursodesoxycholic acid by directly extracting and synthetizing from porcine bile paste or leftovers |
| CN102659891A (en) * | 2012-04-12 | 2012-09-12 | 淮北市恒通生物科技有限公司 | High-purity chenodeoxycholic acid preparation method based on vacuum crystallization technology |
| CN102690856A (en) * | 2012-05-30 | 2012-09-26 | 绵阳劲柏生物科技有限责任公司 | Process using microbial solution to prepare free bile acid |
| CN102703556A (en) * | 2012-05-30 | 2012-10-03 | 绵阳劲柏生物科技有限责任公司 | Method for separating chenodeoxycholic acid from duck bile by using macroporous resin |
| CN103360454A (en) * | 2013-05-06 | 2013-10-23 | 广西大学 | Method for separating and purifying chenodeoxycholic acid from goose bile |
| CN103893210A (en) * | 2012-12-25 | 2014-07-02 | 辽宁省药物研究院 | Chicken gallbladder extraction composition and extraction method thereof |
| CN105566428A (en) * | 2016-01-20 | 2016-05-11 | 常德云港生物科技有限公司 | Method for removing hyocholic acid from chenodeoxycholic acid |
| CN112322684A (en) * | 2020-11-09 | 2021-02-05 | 湖南夏盛酶技术有限公司 | Method for extracting bile acid by using high-efficiency enzyme of oxgall |
| CN113999886A (en) * | 2021-12-06 | 2022-02-01 | 江苏省农业科学院 | Method for extracting chicken bile acid by one-pot enzymolysis |
| CN115089513A (en) * | 2020-11-26 | 2022-09-23 | 徐美铃 | Camellia seed oil extract moisturizing and hydrating cream |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102453071A (en) * | 2010-10-23 | 2012-05-16 | 毕思宾 | Method for preparing chenodeoxycholic acid and ursodesoxycholic acid by directly extracting and synthetizing from porcine bile paste or leftovers |
| CN102453071B (en) * | 2010-10-23 | 2016-04-13 | 成都药晟生物科技有限公司 | The preparation method of extracting directly synthesis Chenodiol and ursodesoxycholic acid from Fel Sus domestica unguentum or tankage |
| CN102659891A (en) * | 2012-04-12 | 2012-09-12 | 淮北市恒通生物科技有限公司 | High-purity chenodeoxycholic acid preparation method based on vacuum crystallization technology |
| CN102690856A (en) * | 2012-05-30 | 2012-09-26 | 绵阳劲柏生物科技有限责任公司 | Process using microbial solution to prepare free bile acid |
| CN102703556A (en) * | 2012-05-30 | 2012-10-03 | 绵阳劲柏生物科技有限责任公司 | Method for separating chenodeoxycholic acid from duck bile by using macroporous resin |
| CN102703556B (en) * | 2012-05-30 | 2013-08-21 | 绵阳劲柏生物科技有限责任公司 | Method for separating chenodeoxycholic acid from duck bile by using macroporous resin |
| CN103893210A (en) * | 2012-12-25 | 2014-07-02 | 辽宁省药物研究院 | Chicken gallbladder extraction composition and extraction method thereof |
| CN103893210B (en) * | 2012-12-25 | 2017-04-19 | 辽宁省药物研究院 | Chicken gallbladder extraction composition and extraction method thereof |
| CN103360454B (en) * | 2013-05-06 | 2015-12-09 | 广西大学 | A kind of method of separating-purifying Chenodiol from goose bile |
| CN103360454A (en) * | 2013-05-06 | 2013-10-23 | 广西大学 | Method for separating and purifying chenodeoxycholic acid from goose bile |
| CN105566428A (en) * | 2016-01-20 | 2016-05-11 | 常德云港生物科技有限公司 | Method for removing hyocholic acid from chenodeoxycholic acid |
| CN112322684A (en) * | 2020-11-09 | 2021-02-05 | 湖南夏盛酶技术有限公司 | Method for extracting bile acid by using high-efficiency enzyme of oxgall |
| CN115089513A (en) * | 2020-11-26 | 2022-09-23 | 徐美铃 | Camellia seed oil extract moisturizing and hydrating cream |
| CN113999886A (en) * | 2021-12-06 | 2022-02-01 | 江苏省农业科学院 | Method for extracting chicken bile acid by one-pot enzymolysis |
| CN113999886B (en) * | 2021-12-06 | 2023-07-04 | 江苏省农业科学院 | Method for extracting chicken bile acid by one-pot enzymolysis |
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