CN108640956A - A method of preparing flavonoid glycoside from tea seed - Google Patents
A method of preparing flavonoid glycoside from tea seed Download PDFInfo
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- CN108640956A CN108640956A CN201810364358.0A CN201810364358A CN108640956A CN 108640956 A CN108640956 A CN 108640956A CN 201810364358 A CN201810364358 A CN 201810364358A CN 108640956 A CN108640956 A CN 108640956A
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- tea seed
- flavonoid glycoside
- fermentation
- seed
- alcohol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Abstract
The present invention discloses a kind of method preparing flavonoid glycoside from tea seed, comprises the steps of：By tea seed degreasing, tea seed is further processed using microbial fermentation technology, it will treated filters after tea seed extracts with alcohol solution, filtrate is concentrated into no alcohol, filtrate is extracted using polar solvent, the aqueous layer being collected into is extracted with ethyl acetate, and ethyl acetate layer is concentrated and is dried, flavones glucoside extract is obtained.Preparation method provided by the invention extracts microbial fermentation technology applied to active components of plants, effectively improves the recovery rate of flavonoid glycoside in tea seed, can be used for industrialized production.
Description
Technical field
The present invention relates to microbial fermentation and plant extracts technical fields, more particularly to one kind preparing Huang from tea seed
The method of ketoside.
Background technology
Tea oil tree is the distinctive woody oil tree species in China, belongs to Theaceae Camellia, is planted so far since between the Southern Song Dynasty year
Have more than 2300 years history, and be distributed that wide, yield is big, medicinal to record position more.It is known as " east olive oil ", " precious in oil
The good reputation of product ", " green oil depot ", " green national treasury ", and olive, oil palm, coconut and claims " four big woody oil tree species of the world ".
Tea seed mainly for the production of tea oil and Tea Saponin, and have numerous studies show its have certain bioactivity and
Pharmacological action.In recent years, a series of research has been carried out to tea seed both at home and abroad, discovery wherein also contains flavones ingredient, main
If being made of kaempferol, flavanones and its glucosides, content is generally 0.1%~0.2%.Flavonoid glycoside is important in tea seed
Active constituent has the function of good removing free radical, can by inhibit such as iNOS of the proinflammatory factor in some cells and
The expression of COX-2 and play excellent antiphlogistic effects, it is potential exploitation for treatment inflammation clinical medicine, as natural plant
Drug, can be to avoid the side effect of steroid and nonsteroidal anti-inflammatory.
Disclose that " high speed adverse current chromatogram prepares yellow in tea seed shell application No. is the patent document of CN201510345178.4
The method of ketone compounds ", this method are made 2 flavone compounds by raw material of tea seed shell, are used in the patent a variety of
Organic solvent.Application No. is the patent documents of CN201310297274.7 to disclose a kind of " preparation side of camellia flavonoid for reducing blood glucose
Method and its application ", the grouts after being extracted oil using tea seed are carried out the preparative separation of blood-sugar decreasing active, are disadvantageous in that
This method is isolated and purified using conventional resins, and time-consuming.Application No. is the patent documents of CN201010229218.6 to disclose
" preparation method of flavonoid glycoside in a kind of middle compression leg quick separating cake of camellia oleifera seeds ", obtains 95% or more flavonoid glycoside monomer, but
The processing step is cumbersome, and operation is not easy.
Invention content
The method that the object of the present invention is to provide a kind of to prepare flavonoid glycoside from tea seed using microbe fermentation method and has
Solvent abstraction technique makes the active constituent flavonoid glycoside in tea seed be fully extracted out.
To achieve the above object of the invention, the present invention adopts the following technical scheme that：
A method of preparing flavonoid glycoside from tea seed, including：
(1) fluid nutrient medium will be made after tea seed degreasing, then accesses black-koji mould and ferments；
(2) fermentation ends, by fermentation material sterilising filtration, filter residue and drying is extracted after crushing with alcohol-water solution；
(3) it is filtered after the completion of extraction, filtrate is concentrated into no alcohol and adds polar solvent extract, collects aqueous layer；
(4) aqueous layer is extracted with ethyl acetate, collects ethyl acetate layer, is concentrated, dry, obtains flavonoid glycoside extraction
Object.
In step (1), it is further that 40~80 DEG C of reflux carry out degreasing that petroleum ether, which can be used, in 30~80 DEG C in tea seed.Institute
The volume ratio for stating petroleum ether and tea seed is (2~3):1.
The liquid culture medium is made of blood meal, dipotassium hydrogen phosphate, magnesium sulfate and water.In parts by weight, group becomes：Oil tea
9~11 parts of the seed dregs of rice, 1~3 part of blood meal, 0.01~0.03 part of dipotassium hydrogen phosphate, 0.008~0.009 part of magnesium sulfate, water 15~18
Part；Further group becomes：10 parts of camellia seed meal, 2 parts of blood meal, 0.016 part of dipotassium hydrogen phosphate, 0.008 part of magnesium sulfate, 16 parts of water.
The fermentation includes：Seed liquor is made after black-koji mould is activated, then accesses in liquid culture medium and ferments.
The inoculum concentration when fermentation is 5-8%.
The temperature of fermentation, rotating speed, time can influence the yield and purity of product, and the temperature of the fermentation is 20~40 DEG C,
Shaking speed is 100~250rpm, and fermentation time is 3~8d；It is further preferred that the temperature of the fermentation is 30~35 DEG C,
Shaking speed is 150~200rpm, and fermentation time is 4~6d；It is furthermore preferred that the temperature of the fermentation is 30 DEG C, shaking speed
For 180rpm, fermentation time 4d.
In step (2), it is 50%~70% ethanol water that alcohol-water solution, which is mass fraction, alcohol-water solution and filter residue
Volume ratio is (8~12):1；The temperature of the extraction is 60~80 DEG C, and the number of extraction is 1~4 time, the time extracted every time
For 1~3h；Preferably, it is 50%~60% ethanol water, the body of alcohol-water solution and filter residue that alcohol-water solution, which is mass fraction,
Product is than being (8~10):1；The temperature of the extraction is 70~75 DEG C, and the number of extraction is 3~4 times.
In step (3), the polar solvent is any one in n-butanol, n-hexane, petroleum ether；The polar solvent
Volume ratio with filtrate is (0.5~1):1；Extraction times are 1~3 time；Preferably, the volume ratio of the polar solvent and filtrate
It is 0.5:1；Extraction times are 2 times.
In step (4), the volume ratio of ethyl acetate and aqueous layer is (1~2):1；Extraction times are 2~4 times, further
It is 3 times.
Compared with prior art, beneficial effects of the present invention are：
This technology utilization microbial fermentation fully improves the recovery rate of flavonoid glycoside in tea seed, and the later stage first uses low polarity
Solvent extraction, then be extracted with ethyl acetate so that impurity is less in obtained flavonoid glycoside, and purity higher makes its utility value fill
Divide and improve, condition is easily controllable, and production cost is low, and gained flavonoid glycoside content may be up to 95% or more in highest.
Specific implementation mode
With reference to specific embodiment, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the invention, after having read the present invention, various equivalences of the those skilled in the art to the present invention
The modification of form falls within the application range as defined in the appended claims.
In the present invention, blood meal is pig blood blood meal, is bought from Wan Wei feed addictives Co., Ltd of Anqiu City；
Aspergillus niger：Using the common Aspergillus niger strain of industrial fermentation, it is purchased from north and receives biology, number BNCC336168.
Fluid nutrient medium：Camellia seed meal (tea seed after degreasing) 10g, blood meal 2g；Dipotassium hydrogen phosphate 0.016g；Magnesium sulfate
0.008g mixings are placed in 50ml conical flasks, are added water 16ml, are stirred evenly, fluid nutrient medium is made.
Embodiment 1：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 40 DEG C with 2 times of volume petroleum ethers；
(2) tea seed that step (1) is handled well dry, pulverize, 10 times of 60% ethyl alcohol of volume (mass fraction) is added, in
70 DEG C are extracted 3 times, each 1h, filtering, and filtrate, which merges, is concentrated into no alcohol；
(3) filtrate for obtaining step (2) 0.5 times of volume petroleum ether extraction 1 time, collects aqueous layer；
(4) the aqueous layer equal volume amounts ethyl acetate obtained in step (3) is extracted 2 times, collects ethyl acetate layer, it is dense
Contracting, drying, obtains flavonoid glycoside 0.021g, yield 0.21%.
It is detected through efficient liquid phase, the content of flavonoid glycoside is 85% in sample.
Embodiment 2：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 80 DEG C with 2 times of volume petroleum ethers；
(2) blood meal, dipotassium hydrogen phosphate, magnesium sulfate, distilled water are added in the tea seed handled well to step (1), liquid is made
Body culture medium, sterilize 20min in 121 DEG C；
(3) activation medium (PDA culture medium) and seed culture medium (liquid PDA culture medium) are prepared, to black-koji mould into
Row activation and amplification (amplification condition：30 DEG C of 150rpm vibrate 72h), prepare seed strain liquid；
(4) fluid nutrient medium made of seed strain liquid and step (2) is utilized, is inoculated with and is fermented, inoculum concentration is
5%-8% (mass fraction), temperature are 20 DEG C, shaking speed 100rpm, fermentation time 3d；
(5) the good tunning of step (4) inoculation fermentation is inactivated in 121 DEG C of 30min, high speed centrifugation takes solid portion
It dry, pulverize, 8 times of 50% ethyl alcohol of volume (mass fraction) are added, extracted 2 times, each 1h in 60 DEG C, filtering, filtrate merges dense
It is reduced to no alcohol；
(6) filtrate for obtaining step (5) 0.5 times of volume petroleum ether extraction 2 times, collects aqueous layer；
(7) the aqueous layer equal volume amounts ethyl acetate for obtaining step (6) extracts 2 times, collects ethyl acetate layer, dense
Contracting, drying, obtains flavonoid glycoside 0.027g, yield 0.27%.
Flavonoid glycoside content assaying method is with embodiment 1, and the content of flavonoid glycoside is 87% in sample.
Embodiment 3：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 60 DEG C with 2 times of volume petroleum ethers；
(2) blood meal, dipotassium hydrogen phosphate, magnesium sulfate, distilled water are added in the tea seed handled well to step (1), liquid is made
Body culture medium, sterilize 20min in 121 DEG C；
(3) activation medium (PDA culture medium) and seed culture medium (liquid PDA culture medium) are prepared, to black-koji mould into
Row activation and amplification, prepare seed strain liquid；
(4) fluid nutrient medium made of seed strain liquid and step (2) is utilized, is inoculated with and is fermented, inoculum concentration is
5%-8%, temperature are 30 DEG C, shaking speed 150rpm, fermentation time 3d；
(5) the good tunning of step (4) inoculation fermentation is inactivated in 121 DEG C of 30min, high speed centrifugation takes solid portion
It dry, pulverize, 10 times of 50% ethyl alcohol of volume are added, extracted 3 times, each 1h in 70 DEG C, filtering, filtrate, which merges, is concentrated into no alcohol；
(6) filtrate for obtaining step (5) 0.5 times of volume petroleum ether extraction 2 times, collects aqueous layer；
(7) the aqueous layer equal volume amounts ethyl acetate for obtaining step (6) extracts 3 times, collects ethyl acetate layer, dense
Contracting, drying, obtains flavonoid glycoside 0.029g, yield 0.29%.
Flavonoid glycoside content assaying method is with embodiment 1, and the content of flavonoid glycoside is 90.31% in sample.
Embodiment 4：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 40 DEG C with 2 times of volume petroleum ethers；
(2) blood meal, dipotassium hydrogen phosphate, magnesium sulfate, distilled water are added in the tea seed handled well to step (1), liquid is made
Body culture medium, sterilize 20min in 121 DEG C；
(3) activation medium (PDA culture medium) and seed culture medium (liquid PDA culture medium) are prepared, to black-koji mould into
Row activation and amplification, prepare seed strain liquid；
(4) fluid nutrient medium made of seed strain liquid and step (2) is utilized, is inoculated with and is fermented, inoculum concentration is
5%-8%, temperature are 30 DEG C, shaking speed 180rpm, fermentation time 4d；
(5) the good tunning of step (4) inoculation fermentation is inactivated in 121 DEG C of 30min, high speed centrifugation takes solid portion
It dry, pulverize, 8 times of 60% ethyl alcohol of volume are added, extracted 3 times, each 1h in 70 DEG C, filtering, filtrate, which merges, is concentrated into no alcohol；
(6) filtrate for obtaining step (5) 0.5 times of volume petroleum ether extraction 2 times, collects aqueous layer；
(7) the aqueous layer equal volume amounts ethyl acetate for obtaining step (6) extracts 3 times, collects ethyl acetate layer, dense
Contracting, drying, obtains flavonoid glycoside 0.0378g, yield 0.378%.
Flavonoid glycoside content assaying method is with embodiment 1, and the content of flavonoid glycoside is 95.5% in sample.
Embodiment 5：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 40 DEG C with 2 times of volume petroleum ethers；
(2) blood meal, dipotassium hydrogen phosphate, magnesium sulfate, distilled water are added in the tea seed handled well to step (1), liquid is made
Body culture medium, sterilize 20min in 121 DEG C；
(3) activation medium (PDA culture medium) and seed culture medium (liquid PDA culture medium) are prepared, to black-koji mould into
Row activation and amplification, prepare seed strain liquid；
(4) fluid nutrient medium made of seed strain liquid and step (2) is utilized, is inoculated with and is fermented, inoculum concentration is
5%-8%, temperature are 30 DEG C, shaking speed 180rpm, fermentation time 3d；
(5) the good tunning of step (4) inoculation fermentation is inactivated in 121 DEG C of 30min, high speed centrifugation takes solid portion
It dry, pulverize, 10 times of 60% ethyl alcohol of volume are added, extracted 3 times, each 1h in 70 DEG C, filtering, filtrate, which merges, is concentrated into no alcohol；
(6) filtrate for obtaining step (5) 0.5 times of volume petroleum ether extraction 1 time, collects aqueous layer；
(7) the aqueous layer equivalent ethyl acetate for obtaining step (6) extracts 2 times, collects ethyl acetate layer, concentrates, and dries
It is dry, obtain flavonoid glycoside 0.0335g, yield 0.335%.
Flavonoid glycoside content assaying method is with embodiment 1, and the content of flavonoid glycoside is 91.3% in sample.
Embodiment 6：
(1) 10g tea seeds are taken, crushes, degreasing is heated to reflux in 50 DEG C with 2 times of volume petroleum ethers；
(2) blood meal, dipotassium hydrogen phosphate, magnesium sulfate, distilled water are added in the tea seed handled well to step (1), liquid is made
Body culture medium, sterilize 20min in 121 DEG C；
(3) activation medium (PDA culture medium) and seed culture medium (liquid PDA culture medium) are prepared, to black-koji mould into
Row activation and amplification, prepare seed strain liquid；
(4) fluid nutrient medium made of seed strain liquid and step (2) is utilized, is inoculated with and is fermented, inoculum concentration is
5%-8%, temperature are 30 DEG C, shaking speed 180rpm, fermentation time 3d；
(5) the good tunning of step (4) inoculation fermentation is inactivated in 121 DEG C of 30min, high speed centrifugation takes solid portion
It dry, pulverize, 10 times of 60% ethyl alcohol of volume are added, extracted 3 times, each 1h in 60 DEG C, filtering, filtrate, which merges, is concentrated into no alcohol；
(6) filtrate for obtaining step (5) 0.5 times of volume petroleum ether extraction 2 times, collects aqueous layer；
(7) the aqueous layer equivalent ethyl acetate for obtaining step (6) extracts 3 times, collects ethyl acetate layer, concentrates, and dries
It is dry, obtain flavonoid glycoside 0.0309g, yield 0.309%.
Flavonoid glycoside content assaying method is with embodiment 1, and the content of flavonoid glycoside is 93.7% in sample.
Claims (10)
1. a kind of method preparing flavonoid glycoside from tea seed, which is characterized in that including：
(1) fluid nutrient medium will be made after tea seed degreasing, then accesses black-koji mould and ferments；
(2) fermentation ends, by fermentation material sterilising filtration, filter residue and drying is extracted after crushing with alcohol-water solution；
(3) it is filtered after the completion of extraction, filtrate is concentrated into no alcohol and adds polar solvent extract, collects aqueous layer；
(4) aqueous layer is extracted with ethyl acetate, collects ethyl acetate layer, is concentrated, dry, obtains flavones glucoside extract.
2. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that tea seed uses oil
Ether carries out degreasing in 30~80 DEG C of reflux；The volume ratio of the petroleum ether and tea seed is (2~3):1.
3. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that the liquid culture medium
It is made of blood meal, dipotassium hydrogen phosphate, magnesium sulfate and water.
4. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that the fermentation includes：
Seed liquor is made after black-koji mould is activated, then accesses in liquid culture medium and ferments.
5. the method according to claim 1 or 4 for preparing flavonoid glycoside from tea seed, which is characterized in that when the fermentation
Inoculum concentration be 5-8%；The temperature of the fermentation be 20~40 DEG C, shaking speed be 100~250rpm, fermentation time be 3~
8d。
6. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that in step (2), alcohol-
It is 50%~70% ethanol water that aqueous solution, which is mass fraction, and the volume ratio of alcohol-water solution and fermentation material is (8~12):1.
7. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that described in step (2)
The temperature of extraction is 60~80 DEG C, and the number of extraction is 1~4 time, and the time extracted every time is 1~3h.
8. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that described in step (3)
Polar solvent is any one in n-butanol, n-hexane, petroleum ether.
9. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that described in step (3)
The volume ratio of polar solvent and filtrate is (0.5~1):1；Extraction times are 1~3 time.
10. the method according to claim 1 for preparing flavonoid glycoside from tea seed, which is characterized in that in step (4), second
The volume ratio of acetoacetic ester and aqueous layer is (1~2):1；Extraction times are 2~4 times.
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| CN109381475A (en) * | 2018-12-10 | 2019-02-26 | 武汉轻工大学 | Application of the Radix Puerariae flavone glycoside in the drug for the disease that preparation treatment immunoglobulin E mediates |
| CN114699463A (en) * | 2022-03-07 | 2022-07-05 | 江西神州通油茶科技有限公司 | Process for extracting flavone by using camellia oleifera byproduct |
| CN115501286A (en) * | 2022-10-10 | 2022-12-23 | 湖南文理学院 | Camellia seed shell extract and preparation method and application thereof |
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