CN109097414A - A kind of preparation method of theaflavin-3-gallate - Google Patents
A kind of preparation method of theaflavin-3-gallate Download PDFInfo
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- CN109097414A CN109097414A CN201810970330.1A CN201810970330A CN109097414A CN 109097414 A CN109097414 A CN 109097414A CN 201810970330 A CN201810970330 A CN 201810970330A CN 109097414 A CN109097414 A CN 109097414A
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- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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Abstract
The invention discloses a kind of preparation methods of theaflavin-3-gallate, belong to field of medicine and chemical technology.Preparation method includes: S1) extraction of lichee polyphenol oxidizing ferment；S2) the preparation of theaflavin-3-gallate crude product solution；S3) the purifying of theaflavin-3-gallate crude product.The present invention aoxidizes enzyme source by active polyphenol of fresh lichee skin, theaflavin-3-gallate is prepared by raw material of EGCG and EC, it is purified using macroporous adsorptive resin column technique, theaflavin-3-gallate is prepared in separation, the preparation method is simple, efficient, reproducible, stability is high.
Description
Technical field
The invention belongs to field of medicine and chemical technology, and in particular to a kind of preparation method of theaflavin-3-gallate.
Background technique
Theaflavin-3-gallate is a kind of principal monomer of theaflavins in black tea and the color of black tea infusion
And one of main indicator of flavor.Existing literature shows that theaflavin has a variety of pharmacology and healthcare function, such as reducing blood lipid, antioxygen
Change, anti-aging etc., certain functions aspects are even better than catechin；In recent years, the medicines and health protection function of theaflavin-3-gallate
It can gradually have been a great concern, but the purification difficulty of theaflavin is larger, especially theaflavin-3-gallate monomer
Ingredient to isolate and purify document report even more fewer and fewer.
Polyphenol oxidase (PPO) is also known as catechol-oxydase, it is widely present in plant (such as lichee) tissue, have compared with
The ability of strong catalysis catechin synthesis theaflavin.
Theaflavin-3-gallate crude product is catalyzed and synthesized about the PPO in application litchi rind at present and separate pure
There is not been reported for the method for the change acquisition higher theaflavin-3-gallate of purity.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of preparations of theaflavin-3-gallate
Method, which aoxidizes enzyme source by active polyphenol of fresh lichee skin, with Epigallo-catechin gallate (EGCG) (EGCG)
It is that raw material prepares theaflavin-3-gallate with epicatechin (EC), is carried out using macroporous adsorptive resin column technique
Purifying, separation, prepares high-purity theaflavin -3- gallate；The preparation method is for the first time using the PPO in litchi rind as urging
Agent catalyzes and synthesizes theaflavin-3-gallate, and isolate and purify and obtain the higher theaflavin -3- galla turcica of purity
Acid esters solves catalytic applications of the PPO in theaflavin-3-gallate synthesis in litchi rind, and this method is efficient, repeats
Property it is good, stability is high.
The technical problems to be solved by the invention are realized using following technical scheme.
A kind of preparation method of theaflavin-3-gallate, specifically includes the following steps:
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin, and buffer is added, filters after smashing to pieces, retains filter
Liquid；Buffer is added into filter residue, stirs, filtering retains filtrate；Merge filtrate twice, is then centrifuged for, takes supernatant up to litchi
Branch polyphenol oxidase enzyme solution；
S2) the preparation of theaflavin-3-gallate crude product solution: Epigallo-catechin gallate (EGCG) is weighed
(EGCG) with epicatechin (EC), it is abundant to be added buffer solution, and step S1 is then added) lichee polyphenol oxidation enzyme solution with
And hydrogenperoxide steam generator, it is stirred to react, filters, retain filtrate, as theaflavin-3-gallate crude product solution；
S3) the purifying of theaflavin-3-gallate crude product: the theaflavin -3- gallic acid that step 2) is obtained
Ester crude product solution is gradually added into the chromatographic column for being already equipped with macroporous absorbent resin as column chromatography sample solution, after end of the sample first
It is eluted with aqueous solution, is then eluted again with alcoholic solution, and collect alcoholic solution eluent, the alcoholic solution eluent of collection is subtracted
Pressure is concentrated into no alcohol taste, and freeze-drying obtains theaflavin-3-gallate.
Further, the buffer solution being added every time in step S1 is calculated as 0.1~5mL/ with fresh lichee cortex amount
G, the temperature when buffer is added control within the scope of 0~30 DEG C, and the mixing time is 2~30min, when the centrifugation
Between be 2~30min.
Further, the buffer solution being added every time in step S1 is calculated as 1~2mL/g with fresh lichee cortex amount,
The temperature when buffer is added controls within the scope of 4~10 DEG C.
Further, step S2) described in the weight ratio of Epigallo-catechin gallate (EGCG) and ethylene carbonate be
1:0.1-10；
The weight ratio of the Epigallo-catechin gallate (EGCG) and ethylene carbonate total additional amount and fresh lichee skin
For 1:10-100；
The volumetric usage of the buffer is calculated as 5~200mL/g with fresh lichee cortex amount；
The volume ratio of the hydrogenperoxide steam generator and buffer is 1:100-500；
The temperature that is stirred to react is 0~40 DEG C, and being stirred to react the time is 0.5~3h.
Further, step S2) described in the weight ratio of Epigallo-catechin gallate (EGCG) and ethylene carbonate be
1:0.25~2；The weight of the Epigallo-catechin gallate (EGCG) and ethylene carbonate total additional amount and fresh lichee skin
Than for 1:20-60；The volumetric usage of the buffer is calculated as 5~20mL/g with fresh lichee cortex amount.
Further, step S1) and S2) described in buffer be citric acid and sodium citrate mixed solution or phosphoric acid and
The mixed solution of sodium phosphate.
Further, step S3) loading flow velocity is 0.5~3 times of column volume per hour；
Elution flow rate is 1~4 times of column volume per hour；
Water elution volume is 0.5~2 times of column volume, and alcoholic solution elution volume is 2~12 times of column volumes.
Further, step S3) alcoholic solution be methanol or ethyl alcohol and water mixed solution, body shared by alcohol after mixing
Product ratio is 10~40% (v:v).
Further, step S3) described in macroreticular resin be HPD-100, HPD-200 or HPD-400.
Compared with prior art, the present invention has the following advantages and beneficial effects:
The present invention takes the lead in aoxidizing enzyme source by active polyphenol of fresh lichee skin, prepares tea Huang by raw material of EGCG and EC
Element -3- gallate, is purified using macroporous adsorptive resin column technique, and high-purity theaflavin-is prepared in separation
3- gallate, this preparation method is simple, efficient, reproducible, and stability is high, more suitable for industrialized production.
Specific embodiment
To make the objectives, technical solutions, and advantages of the present invention clearer, combined with specific embodiments below to this hair
Bright technical solution is described in further detail.
Embodiment 1: the preparation process of theaflavin-3-gallate
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin 500g and be put into juice extractor, is added and is cooled to 5 DEG C in advance
500mL citric acid-sodium citrate buffer solution, filter out filtrate after smashing to pieces, filter residue is added is cooled to 5 DEG C of 500mL citric acid-in advance
Sodium citrate buffer solution stirs 10min, filters out filtrate；Merge filtrate twice and be centrifuged 15min in centrifuge, take supernatant to obtain the final product
Lichee polyphenol aoxidizes enzyme solution.S2) the preparation of theaflavin-3-gallate crude product solution: weighing EGCG 5g and EC 5g, is added
Sufficiently, step S1 is added in the dissolution of 2500mL citric acid-sodium citrate buffer solution) in lichee polyphenol oxidation enzyme solution and 25mL peroxide
Change hydrogen solution, 30 DEG C are stirred to react 2h, and filtering gained filtrate is theaflavin-3-gallate crude product solution.S3) tea is yellow
The purifying of element -3- gallate crude product: gradually add theaflavin-3-gallate crude product solution as column chromatography sample solution
Enter to be already equipped in the macroporous adsorption resin chromatography column of model HPD-200, control loading flow velocity is 1BV/h, after end of the sample
First with 2.5BV/h flow velocity respectively with water elution 0.5BV, 6BV is then eluted with 2.5BV/h flow velocity using 20% ethanol solution, is received
Collect 20% ethanol solution elution resin column efflux；20% ethanol solution elution resin column efflux is concentrated under reduced pressure into no alcohol
Taste, freeze-drying obtain theaflavin-3-gallate 4.6g.
Embodiment 2: the preparation process of theaflavin-3-gallate
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin 500g and be put into juice extractor, is added and is cooled to 15 DEG C in advance
2500mL citrate-phosphate sodium buffer, filter out filtrate after smashing to pieces, filter residue is added is cooled to 15 DEG C of 2500mL lemon in advance
Acid-sodium phosphate buffer stirs 2min, filters out filtrate；Merge filtrate twice and be centrifuged 30min in centrifuge, take supernatant to obtain the final product
Lichee polyphenol aoxidizes enzyme solution.S2) the preparation of theaflavin-3-gallate crude product solution: EGCG 20g and EC 5g are weighed, is added
Enter the dissolution of 5000mL citric acid-sodium citrate buffer solution sufficiently, step S1 be added) in lichee polyphenol oxidation enzyme solution and 10mL mistake
Hydrogen peroxide solution, 40 DEG C are stirred to react 3h, and filtering gained filtrate is theaflavin-3-gallate crude product solution.S3) tea is yellow
The purifying of element -3- gallate crude product: gradually add theaflavin-3-gallate crude product solution as column chromatography sample solution
Enter to be already equipped in the macroporous adsorption resin chromatography column of model HPD-400, control loading flow velocity is 0.5BV/h, end of the sample
2BV is eluted with water first with 1BV/h flow velocity afterwards, 12BV is then eluted with 1BV/h flow velocity with 20% ethanol solution, collects 10% ethyl alcohol
Solution elutes resin column efflux；10% ethanol solution elution resin column efflux is concentrated under reduced pressure into no alcohol taste, is freeze-dried
Obtain theaflavin-3-gallate 10.2g.
Embodiment 3: the preparation process of theaflavin-3-gallate
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin 500g and be put into juice extractor, is added and is cooled to 5 DEG C in advance
50mL citric acid-sodium citrate buffer solution, filter out filtrate after smashing to pieces, filter residue is added is cooled to 5 DEG C of 50mL citric acid-lemon in advance
Lemon acid sodium buffer stirs 30min, filters out filtrate；Merge filtrate twice and be centrifuged 2min in centrifuge, takes supernatant up to litchi
Branch polyphenol oxidase enzyme solution.S2) the preparation of theaflavin-3-gallate crude product solution: weighing EGCG 10g and EC 5g, is added
Sufficiently, step S1 is added in the dissolution of 10000mL citric acid-sodium citrate buffer solution) in lichee polyphenol oxidation enzyme solution and 50mL mistake
Hydrogen peroxide solution, 5 DEG C are stirred to react 0.5h, and filtering gained filtrate is theaflavin-3-gallate crude product solution.S3) tea
The purifying of flavine -3- gallate crude product: gradually using theaflavin-3-gallate crude product solution as column chromatography sample solution
Addition is already equipped in the macroporous adsorption resin chromatography column of model HPD-100, and control loading flow velocity is 3BV/h, end of the sample
Afterwards first with 4BV/h flow velocity respectively with water elution 1BV, 2BV is then eluted with 4BV/h flow velocity using 20% ethanol solution, is collected
40% ethanol solution elutes resin column efflux；40% ethanol solution elution resin column efflux is concentrated under reduced pressure into no alcohol taste,
Freeze-drying obtains theaflavin-3-gallate 4.6g.
Embodiment 4: the preparation process of theaflavin-3-gallate
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin 500g and be put into juice extractor, is added and is cooled to 10 DEG C in advance
1000mL phosphoric acid and sodium phosphate buffer, filter out filtrate after smashing to pieces, filter residue be added be cooled in advance 10 DEG C 1000mL phosphoric acid and
Sodium phosphate buffer stirs 17min, filters out filtrate；Merge filtrate twice and be centrifuged 25min in centrifuge, takes supernatant up to litchi
Branch polyphenol oxidase enzyme solution.S2) the preparation of theaflavin-3-gallate crude product solution: weighing EGCG 5g and EC 5g, is added
Sufficiently, step S1 is added in 5000mL phosphoric acid and sodium phosphate buffer dissolution) in lichee polyphenol oxidation enzyme solution and 10mL peroxidating
Hydrogen solution, 30 DEG C are stirred to react 1.5h, and filtering gained filtrate is theaflavin-3-gallate crude product solution.S3) tea is yellow
The purifying of element -3- gallate crude product: gradually add theaflavin-3-gallate crude product solution as column chromatography sample solution
Enter to be already equipped in the macroporous adsorption resin chromatography column of model HPD-200, control loading flow velocity is 0.5BV/h, end of the sample
2BV is eluted with water first with 1BV/h flow velocity afterwards, 12BV is then eluted with 1BV/h flow velocity with 20% ethanol solution, collects 10% ethyl alcohol
Solution elutes resin column efflux；10% ethanol solution elution resin column efflux is concentrated under reduced pressure into no alcohol taste, is freeze-dried
Obtain theaflavin-3-gallate 9.2g.
The present invention is illustrated according to above-described embodiment it should be appreciated that above-described embodiment does not limit this hair in any form
It is bright, it is all to use equivalent substitution or equivalent transformation mode technical solution obtained, it is within the scope of the present invention.
Claims (9)
1. a kind of preparation method of theaflavin-3-gallate, which is characterized in that specifically includes the following steps:
S1) the extraction of lichee polyphenol oxidizing ferment: weighing fresh lichee skin, and buffer is added, filters after smashing to pieces, retains filtrate；To
Buffer is added in filter residue, stirs, filtering retains filtrate；Merge filtrate twice, is then centrifuged for, takes supernatant more up to lichee
Phenol oxidase liquid；
S2 Epigallo-catechin gallate (EGCG) and table catechu the) preparation of theaflavin-3-gallate crude product solution: are weighed
Element, it is abundant to be added buffer solution, and step S1 is then added) lichee polyphenol oxidation enzyme solution and hydrogenperoxide steam generator, are stirred
Reaction is mixed, is filtered, filtrate, as theaflavin-3-gallate crude product solution are retained；
S3) the purifying of theaflavin-3-gallate crude product: the theaflavin-3-gallate that step 2) is obtained is thick
Product solution is gradually added into the chromatographic column for being already equipped with macroporous absorbent resin as column chromatography sample solution, and water is first used after end of the sample
Solution elution, is then eluted with alcoholic solution, and collect alcoholic solution eluent again, and the alcoholic solution eluent decompression of collection is dense
It is reduced to no alcohol taste, freeze-drying obtains theaflavin-3-gallate.
2. a kind of preparation method of theaflavin-3-gallate according to claim 1, which is characterized in that step S1)
In the buffer solution that is added every time 0.1~5mL/g is calculated as with fresh lichee cortex amount, the temperature when buffer is added
Within the scope of 0~30 DEG C, the mixing time is 2~30min for control, and the centrifugation time is 2~30min.
3. a kind of preparation method of theaflavin-3-gallate according to claim 2, which is characterized in that step S1)
In the buffer solution that is added every time 1~2mL/g is calculated as with fresh lichee cortex amount, the temperature control when buffer is added
System is within the scope of 4~10 DEG C.
4. a kind of preparation method of theaflavin-3-gallate according to claim 1, which is characterized in that step S2)
Described in the weight ratio of Epigallo-catechin gallate (EGCG) and ethylene carbonate be 1:0.1-10；
The Epigallo-catechin gallate (EGCG) and the total additional amount of ethylene carbonate and the weight ratio of fresh lichee skin are 1:
10-100；
The volumetric usage of the buffer is calculated as 5~200mL/g with fresh lichee cortex amount；
The volume ratio of the hydrogenperoxide steam generator and buffer is 1:100-500；
The temperature that is stirred to react is 0~40 DEG C, and being stirred to react the time is 0.5~3h.
5. a kind of preparation method of theaflavin-3-gallate according to claim 4, which is characterized in that step S2)
The weight ratio of middle Epigallo-catechin gallate (EGCG) and ethylene carbonate is 1:0.25~2；
The Epigallo-catechin gallate (EGCG) and the total additional amount of ethylene carbonate and the weight ratio of fresh lichee skin are 1:
20-60；
The volumetric usage of the buffer is calculated as 5~20mL/g with fresh lichee cortex amount.
6. a kind of preparation method of theaflavin-3-gallate according to claim 1-5, feature exist
Buffer described in step S1) and S2) is citric acid-sodium citrate or phosphoric acid-sodium phosphate mixed solution.
7. a kind of preparation method of theaflavin-3-gallate according to claim 1, which is characterized in that step S3)
Loading flow velocity is 0.5~3 times of column volume per hour；
Elution flow rate is 1~4 times of column volume per hour；
Water elution volume is 0.5~2 times of column volume, and alcoholic solution elution volume is 2~12 times of column volumes.
8. a kind of preparation method of theaflavin-3-gallate according to claim 7, which is characterized in that step S3)
The alcoholic solution is the mixed solution of methanol or ethyl alcohol and water, and volume ratio shared by alcohol is 10~40% (v:v) after mixing.
9. a kind of preparation method of theaflavin-3-gallate according to claim 8, which is characterized in that step S3)
Described in macroreticular resin be HPD-100, HPD-200 or HPD-400.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110839890A (en) * | 2019-12-03 | 2020-02-28 | 湖南农业大学 | Dietary nutrition supplement for theaflavin muscle strengthening and preparation method thereof |
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| CN1737135A (en) * | 2005-07-28 | 2006-02-22 | 浙江大学 | Method for nanometer fixed enzyme directionally producing TF2A crude extract in vitro |
Non-Patent Citations (4)
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| SANG SM等: "《Theadibenzotropolone A, a new type pigment from enzymatic oxidation of (−)-epicatechin and (−)-epigallocatechin gallate and characterized from black tea using LC/MS/MS》", 《TETRAHEDRON LETTERS》 * |
| 单圣晔: "《茶渣中有效成分儿茶素的研究及应用》", 《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110839890A (en) * | 2019-12-03 | 2020-02-28 | 湖南农业大学 | Dietary nutrition supplement for theaflavin muscle strengthening and preparation method thereof |
| CN110839890B (en) * | 2019-12-03 | 2022-06-21 | 湖南农业大学 | Dietary nutrition supplement for theaflavin muscle strengthening and preparation method thereof |
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