CN107488202A - The extracting method in high yield of salicoside in a kind of white willow branches and leaves - Google Patents
The extracting method in high yield of salicoside in a kind of white willow branches and leaves Download PDFInfo
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- CN107488202A CN107488202A CN201710598127.1A CN201710598127A CN107488202A CN 107488202 A CN107488202 A CN 107488202A CN 201710598127 A CN201710598127 A CN 201710598127A CN 107488202 A CN107488202 A CN 107488202A
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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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
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- C07H1/08—Separation; Purification from natural products
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Abstract
The invention discloses a kind of extracting method in high yield of salicoside in white willow branches and leaves, and it includes crushing, pretreatment, extraction, concentration, adsorbing separation, the step such as decolouring, condensing crystallizing.Ultraviolet irradiation, air-flow crushing, liquid nitrogen frozen and microwave thawing dialogue withy leaf are respectively adopted before extraction and is handled by the present invention, the cell wall structure of white willow branches and leaves can significantly be destroyed, and the active ingredient of cell interior will not be destroyed, nutriment has obtained maximized reservation, is advantageous to the dissolution of salicoside in subsequent extracted technique.Handled successively using low-frequency ultrasonic waves, high-frequency ultrasonic and mid-frequency ultrasonic ripple in extraction process of the present invention, the further broken wall of white willow branches and leaves cell tissue or deformation can be promoted, make its extracts active ingredients more abundant, greatly improve the recovery rate of salicoside, then handled again using high-pressure pulse electric dialogue withy leaf filter residue, the dissolution of residual salicoside in white willow branches and leaves filter residue can further be promoted, greatly improve the yield of salicoside.
Description
Technical field
The invention belongs to field of biological extraction, and in particular to the extracting method in high yield of salicoside in a kind of white willow branches and leaves.
Background technology
Salicoside, English name are D (-)-Salicin, and alias is D- (-)-salicin, molecular formula C13H18O7, CAS
Number it is 138-52-3, molecular weight：286.28, fusing point：199-202℃.
Salicoside is white crystals；Bitter；Specific rotatory power【α】- 45.6 ° of village, often used in village names（0.6 gram/100 centimetres3Absolute ethyl alcohol）；Can
Water is dissolved in, is soluble in boiling water, is insoluble in ethanol (1:90), insoluble in ether or chloroform, but aqueous slkali, pyridine or glacial acetic acid can be dissolved in
In.Its aqueous solution is in neutral reaction, without free phenolic hydroxyl group in molecule, belongs to phenol glycosides compound.Through diluted acid or emulsin water
Solution, can generate glucose and saligenin.The molecular formula of saligenin is C7H8O2；For oblique square colorless needles；86~87 DEG C of fusing point;Heat
To 100 DEG C of distillations；Water-soluble, benzene, it is soluble in ethanol, ether, chloroform；Sulfuric acid is met to take on a red color.
Salicoside is widely present in the branch of Salicaceous Plants white willow, leaf, in root skin, content highest wherein in salicis,cortex.
Pharmacological action：1. treatment heating, flu and infection are used as " natural aspirin ", it is light that salicoside is used for treatment
Slight fever, catch a cold, infection（Influenza）, acute and chronic rheumatism is uncomfortable, headache and the pain caused by inflammation.A Si
Woods（Acetylsalicylic acid）, as the synthesis substitute of salicoside, have potentially to stomach and intestine dangerous side-effects.As its natural structure
Type, salicoside can be converted into salicylic acid harmlessly by gastrointestinal system in blood and liver.Conversion process needs a few hours,
Therefore result will not be arrived by human body sensory immediately, but general effect can last for hours.2. salicoside is mitigating arthritis
In terms of pain and pain in back and loin, the analgesic ability of salicoside generally come into force it is relatively slow but than common aspirin product lasts when
Between it is long.Once experiment finds that a kind of herbal combinations product containing 100ng salicosides after two months can be effective in continuous take
Improve the analgesic ability to arthritic.Another experiment discovery daily intakes 1360mg white willow branches and leaves extracts（Contain 240mg
Salicoside）There can be the effect of more preferable to treatment joint part pain and/or arthritis after fortnight.Use high dose white willow branches and leaves
Extract may also contribute to alleviate pain in back and loin.The experiment for once continuing for four weeks finds the white willow containing 240mg salicosides
Branches and leaves extract can effectively mitigate the deterioration of pain in back and loin.
At present, the preparation method of salicoside mainly has chemical industry synthesis to prepare and extracted from salicis,cortex or white willow branches and leaves.
Chemical industry synthesis method prepares salicoside, uses various organic intermediates, and raw material is not readily available, and also using some has
Solvent, price is high, so holistic cost is higher, has dissolvent residual to be all not easy in product in addition up to standard, and environmental pollution is tight
Weight.
At present, the main method for extracting salicoside from white willow branches and leaves has lime water, methanol, ethanol extraction method, still
The salicoside yield that these methods extract is low, and ash content is high, and purity is low, causes its product price low.
The content of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of carrying in high yield for salicoside in white willow branches and leaves
Method is taken, extracting method raw material of the present invention is easy to get, and is extracted from the white willow branches and leaves of abundance, and obtained product salicoside is received
Rate is high, purity is high, yield ＞ 1.5%, purity ＞ 98%.
To achieve the above object, the present invention adopts the following technical scheme that：
The extracting method in high yield of salicoside, comprises the following steps in a kind of white willow branches and leaves：
（1）Crush：By white willow branches and leaves ultraviolet 15~30min of radiation treatment, then air-flow crushing, crosses 400~500 mesh sieves, obtains
To white willow branches and leaves fine powder；
（2）Pretreatment：White willow branches and leaves fine powder is placed in liquid nitrogen 3~5min of snap frozen under ultralow temperature, it is micro- after rapid taking-up
Ripple thaws 2~4min, such freeze thaw circular treatment 2~3 times；
（3）Extraction, concentration：According to solid-liquid ratio 1:10~15 add white willow branches and leaves fine powder the ethanol solution that volume fraction is 80%
In, 15~20min of first low-frequency ultrasonic waves processing, then high-frequency ultrasonic 5~10min of processing, then mid-frequency ultrasonic ripple processing 10~
15min, 1.5~2.5h of extraction is then refluxed for, filters out extract solution, according to solid-liquid ratio 1:Filter residue addition volume fraction is by 8~12
In 95% ethanol solution, high-pressure pulse electric processing 15~30s, 1~2h of refluxing extraction, extract solution is filtered out, merging is extracted twice
Liquid, relative density is concentrated into as 1.1~1.3；
（4）Adsorbing separation：Step（3）Water of 3~6 times equivalent to concentrate quality is added in obtained concentrate, is sufficiently stirred
Uniformly, centrifuge, take supernatant to be added to blade diameter length ratio as 1 using 1~2BV/h flow velocity:On 7~9 large pore resin absorption column
Adsorbed, first with 2~4BV deionized water rinsing resin, then the second for being 50~80% with 3~5BV volume fraction after absorption
Alcoholic solution is eluted with 1~3BV/h flow velocity, collects eluent；
（5）Decolourize, condensing crystallizing：The activated carbon equivalent to eluent quality 3~6% is added into eluent, return stirring decolourizes
3~5h, cold filtration, it is 1.4~1.8 that filtrate, which is concentrated into relative density, is cooled to 2-4 DEG C, crystallizes 24~36h；
（6）Centrifugation, recrystallization：Crystal crude product is centrifuged, precipitation crude product is recrystallized 3~5 times with water；
（7）Centrifugation：The material recrystallized is centrifuged, precipitation water wash, obtain salicoside fine work wet product precipitation；
（8）Dry：24-48h is dried at a temperature of salicoside fine work wet product is deposited in into 60~70 DEG C, obtains salicoside finished product.
Step（1）Described in ultraviolet radiation treatment middle-ultraviolet lamp wavelength be 240~270nm, irradiation intensity is 100~
150μW/cm2。
Step（1）Described in the pressure of air-flow crushing be 1~1.5MPa.
Step（2）Described in ultralow temperature temperature be -40~-50 DEG C.
Step（2）Described in microwave thawing microwave frequency be 900~1000MHz, microwave power is 200~300W.
Step（3）Described in low-frequency ultrasonic waves processing in ultrasonic frequency be 20~40KHz, ultrasonic power density is
300~400W/L.
Step（3）Described in high-frequency ultrasonic processing ultrasonic frequency be 800~1000KHz, ultrasonic power density
For 100~200W/L.
Step（3）Described in mid-frequency ultrasonic ripple processing in ultrasonic frequency be 350~500KHz, ultrasonic power density is
250~350W/L.
Step（3）Described in high-pressure pulse electric processing electric-field intensity be 20~30kV/cm, umber of pulse is 8~10.
Step（4）Described in macroporous absorbent resin be HPD-826 type macroporous absorbent resins.
Beneficial effects of the present invention：
Ultraviolet irradiation, air-flow crushing, liquid nitrogen frozen and microwave thawing dialogue withy leaf is respectively adopted in the present invention before extraction
Handled, can significantly destroy the cell wall structure of white willow branches and leaves, and the active ingredient of cell interior will not be destroyed, nutrients
Matter has obtained maximized reservation, is advantageous to the dissolution of salicoside in subsequent extracted technique.Adopted successively in extraction process of the present invention
Handled with low-frequency ultrasonic waves, high-frequency ultrasonic and mid-frequency ultrasonic ripple, white willow branches and leaves cell tissue can be promoted further to break
Wall or deformation, make its extracts active ingredients more abundant, greatly improve the recovery rate of salicoside, then use high-pressure pulse electric again
Dialogue withy leaf filter residue is handled, and can further be promoted to remain the dissolution of salicoside in white willow branches and leaves filter residue, be greatly improved
The yield of salicoside；Finally by obtained extract successively through HPD-826 type macroporous absorbent resins adsorbing separation, decolouring, concentration
The techniques such as crystallization, recrystallization, the purity of salicoside can be significantly improved.
Extracting method raw material of the present invention is easy to get, and is extracted from the white willow branches and leaves of abundance, and obtained product salicoside
High income, purity are high, yield ＞ 1.5%, purity ＞ 98%.
Embodiment
Embodiment 1
The extracting method in high yield of salicoside, comprises the following steps in a kind of white willow branches and leaves：
（1）Crush：In ultraviolet wavelength it is 240nm by white willow branches and leaves, irradiation intensity is 100 μ W/cm2Under conditions of ultraviolet
Radiation treatment 30min, then the air-flow crushing under conditions of pressure is 1MPa, crosses 400 mesh sieves, obtains white willow branches and leaves fine powder；
（2）Pretreatment：White willow branches and leaves fine powder is placed in liquid nitrogen the snap frozen 5min in the case where temperature is -40 DEG C of ultralow temperature, it is fast
Speed in microwave frequency is 900MHz after taking out, and microwave power is 200W microwave thawings 4min, such freeze thaw circular treatment 2
It is secondary；
（3）Extraction, concentration：According to solid-liquid ratio 1:10 add white willow branches and leaves fine powder in the ethanol solution that volume fraction is 80%, first
It is 20KHz in ultrasonic frequency, low-frequency ultrasonic waves handle 20min under conditions of ultrasonic power density is 300W/L, then super
Frequency of sound wave is 800KHz, and high-frequency ultrasonic handles 10min under conditions of ultrasonic power density is 100W/L, then in ultrasonic wave
Frequency is 350KHz, and the condition mid-frequency ultrasonic ripple that ultrasonic power density is 250W/L handles 15min, is then refluxed for extracting
1.5h, extract solution is filtered out, according to solid-liquid ratio 1:8 add filter residue in the ethanol solution that volume fraction is 95%, are in electric-field intensity
20kV/cm, high-pressure pulse electric handles 30s, refluxing extraction 1h under conditions of umber of pulse is 8, filters out extract solution, and merging carries twice
Liquid is taken, is concentrated into relative density as 1.1；
（4）Adsorbing separation：Step（3）Water of 3 times equivalent to concentrate quality is added in obtained concentrate, is sufficiently stirred
It is even, centrifuge, take supernatant to be added to blade diameter length ratio as 1 using 1BV/h flow velocity:On 7 HPD-826 type large pore resin absorption columns
Adsorbed, first use 2BV deionized water rinsing resin after absorption, then with the ethanol solution that 3BV volume fraction is 50% with
1BV/h flow velocity is eluted, and collects eluent；
（5）Decolourize, condensing crystallizing：Into eluent add equivalent to eluent quality 3% activated carbon, return stirring decolouring 3h,
Cold filtration, it is 1.4 that filtrate, which is concentrated into relative density, is cooled to 2 DEG C, crystallizes 24h；
（6）Centrifugation, recrystallization：Crystal crude product is centrifuged, precipitation crude product is recrystallized 3 times with water；
（7）Centrifugation：The material recrystallized is centrifuged, precipitation water wash, obtain salicoside fine work wet product precipitation；
（8）Dry：48h is dried at a temperature of salicoside fine work wet product is deposited in into 60 DEG C, obtains salicoside finished product.
Above-described embodiment extracts obtained salicoside finished product, and its yield is 1.624%, purity 98.75%.
Embodiment 2
The extracting method in high yield of salicoside, comprises the following steps in a kind of white willow branches and leaves：
（1）Crush：In ultraviolet wavelength it is 255nm by white willow branches and leaves, irradiation intensity is 120 μ W/cm2Under conditions of ultraviolet
Radiation treatment 25min, then the air-flow crushing under conditions of pressure is 1.2MPa, crosses 450 mesh sieves, obtains white willow branches and leaves fine powder；
（2）Pretreatment：White willow branches and leaves fine powder is placed in liquid nitrogen the snap frozen 4min in the case where being -45 DEG C of ultralow temperature in temperature,
It is rapid take out after in microwave frequency be 950MHz, microwave power is microwave thawing 3min under conditions of 250W, such freeze thaw
Circular treatment 3 times；
（3）Extraction, concentration：According to solid-liquid ratio 1:12 add white willow branches and leaves fine powder in the ethanol solution that volume fraction is 80%, first
It is 30KHz in ultrasonic frequency, low-frequency ultrasonic waves handle 18min under conditions of ultrasonic power density is 350W/L, then super
Frequency of sound wave is 900KHz, and high-frequency ultrasonic handles 7min under conditions of ultrasonic power density is 150W/L, then in ultrasonic wave
Frequency is 450KHz, and mid-frequency ultrasonic ripple handles 12min under conditions of ultrasonic power density is 300W/L, is then refluxed for extracting
1.5h, extract solution is filtered out, according to solid-liquid ratio 1:10 add filter residue in the ethanol solution that volume fraction is 95%, in electric-field intensity
For 25kV/cm, high-pressure pulse electric handles 25s, refluxing extraction 1.5h under conditions of umber of pulse is 9, filters out extract solution, merges two
Secondary extract solution, relative density is concentrated into as 1.2；
（4）Adsorbing separation：Step（3）Water of 4.5 times equivalent to concentrate quality is added in obtained concentrate, is sufficiently stirred
It is even, centrifuge, take supernatant to be added to blade diameter length ratio as 1 using 1.5BV/h flow velocity:8 HPD-826 type large pore resin absorption columns
On adsorbed, first use 3BV deionized water rinsing resin after absorption, then with the ethanol solution that 4BV volume fraction is 65% with
2BV/h flow velocity is eluted, and collects eluent；
（5）Decolourize, condensing crystallizing：The activated carbon equivalent to eluent quality 4.5% is added into eluent, return stirring decolourizes
4h, cold filtration, it is 1.6 that filtrate, which is concentrated into relative density, is cooled to 3 DEG C, crystallizes 30h；
（6）Centrifugation, recrystallization：Crystal crude product is centrifuged, precipitation crude product is recrystallized 4 times with water；
（7）Centrifugation：The material recrystallized is centrifuged, precipitation water wash, obtain salicoside fine work wet product precipitation；
（8）Dry：36h is dried at a temperature of salicoside fine work wet product is deposited in into 65 DEG C, obtains salicoside finished product.
Above-described embodiment extracts obtained salicoside finished product, and its yield is 1.804%, purity 99.26%.
Embodiment 3
The extracting method in high yield of salicoside, comprises the following steps in a kind of white willow branches and leaves：
（1）Crush：In ultraviolet wavelength it is 270nm by white willow branches and leaves, irradiation intensity is 150 μ W/cm2Under conditions of ultraviolet spoke
According to processing 15min, then the air-flow crushing under conditions of pressure is 1.5MPa, crosses 500 mesh sieves, obtains white willow branches and leaves fine powder；
（2）Pretreatment：White willow branches and leaves fine powder is placed in liquid nitrogen the snap frozen 3min in the case where temperature is -50 DEG C of ultralow temperature, it is fast
Speed in microwave frequency be 1000MHz after taking out, and microwave power is microwave thawing 2min under conditions of 300W, such freeze thaw
Circular treatment 3 times；
（3）Extraction, concentration：According to solid-liquid ratio 1:15 add white willow branches and leaves fine powder in the ethanol solution that volume fraction is 80%, first
It is 40KHz in ultrasonic frequency, low-frequency ultrasonic waves handle 15min under conditions of ultrasonic power density is 400W/L, then super
Frequency of sound wave is 1000KHz, and high-frequency ultrasonic handles 5min under conditions of ultrasonic power density is 200W/L, then in ultrasonic wave
Frequency is 500KHz, and mid-frequency ultrasonic ripple handles 10min under conditions of ultrasonic power density is 350W/L, is then refluxed for extracting
2h, extract solution is filtered out, according to solid-liquid ratio 1:12 add filter residue in the ethanol solution that volume fraction is 95%, are in electric-field intensity
30kV/cm, high-pressure pulse electric handles 15s, refluxing extraction 2h under conditions of umber of pulse is 10, filters out extract solution, merges twice
Extract solution, relative density is concentrated into as 1.3；
（4）Adsorbing separation：Step（3）Water of 6 times equivalent to concentrate quality is added in obtained concentrate, is sufficiently stirred
It is even, centrifuge, take supernatant to be added to blade diameter length ratio as 1 using 2BV/h flow velocity:On 9 HPD-826 type large pore resin absorption columns
Adsorbed, first use 4BV deionized water rinsing resin after absorption, then with the ethanol solution that 5BV volume fraction is 80% with
3BV/h flow velocity is eluted, and collects eluent；
（5）Decolourize, condensing crystallizing：Into eluent add equivalent to eluent quality 6% activated carbon, return stirring decolouring 5h,
Cold filtration, it is 1.8 that filtrate, which is concentrated into relative density, is cooled to 4 DEG C, crystallizes 36h；
（6）Centrifugation, recrystallization：Crystal crude product is centrifuged, precipitation crude product is recrystallized 5 times with water；
（7）Centrifugation：The material recrystallized is centrifuged, precipitation water wash, obtain salicoside fine work wet product precipitation；
（8）Dry：24h is dried at a temperature of salicoside fine work wet product is deposited in into 70 DEG C, obtains salicoside finished product.
Above-described embodiment extracts obtained salicoside finished product, and its yield is 1.747%, purity 98.93%.
Claims (10)
1. the extracting method in high yield of salicoside in a kind of white willow branches and leaves, it is characterised in that comprise the following steps：
（1）Crush：By white willow branches and leaves ultraviolet 15~30min of radiation treatment, then air-flow crushing, crosses 400~500 mesh sieves, obtains
To white willow branches and leaves fine powder；
（2）Pretreatment：White willow branches and leaves fine powder is placed in liquid nitrogen 3~5min of snap frozen under ultralow temperature, it is micro- after rapid taking-up
Ripple thaws 2~4min, such freeze thaw circular treatment 2~3 times；
（3）Extraction, concentration：According to solid-liquid ratio 1:10~15 add white willow branches and leaves fine powder the ethanol solution that volume fraction is 80%
In, 15~20min of first low-frequency ultrasonic waves processing, then high-frequency ultrasonic 5~10min of processing, then mid-frequency ultrasonic ripple processing 10~
15min, 1.5~2.5h of extraction is then refluxed for, filters out extract solution, according to solid-liquid ratio 1:Filter residue addition volume fraction is by 8~12
In 95% ethanol solution, high-pressure pulse electric processing 15~30s, 1~2h of refluxing extraction, extract solution is filtered out, merging is extracted twice
Liquid, relative density is concentrated into as 1.1~1.3；
（4）Adsorbing separation：Step（2）Water of 3~6 times equivalent to concentrate quality is added in obtained concentrate, is sufficiently stirred
Uniformly, centrifuge, take supernatant to be added to blade diameter length ratio as 1 using 1~2BV/h flow velocity:On 7~9 large pore resin absorption column
Adsorbed, first with 2~4BV deionized water rinsing resin, then the second for being 50~80% with 3~5BV volume fraction after absorption
Alcoholic solution is eluted with 1~3BV/h flow velocity, collects eluent；
（5）Decolourize, condensing crystallizing：The activated carbon equivalent to eluent quality 3~6% is added into eluent, return stirring decolourizes
3~5h, cold filtration, it is 1.4~1.8 that filtrate, which is concentrated into relative density, is cooled to 2-4 DEG C, crystallizes 24~36h；
（6）Centrifugation, recrystallization：Crystal crude product is centrifuged, precipitation crude product is recrystallized 3~5 times with water；
（7）Centrifugation：The material recrystallized is centrifuged, precipitation water wash, obtain salicoside fine work wet product precipitation；
（8）Dry：24~48h is dried at a temperature of salicoside fine work wet product is deposited in into 60~70 DEG C, obtains salicoside finished product.
2. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（1）Described in ultraviolet radiation treatment middle-ultraviolet lamp wavelength be 240~270nm, irradiation intensity is 100~150 μ W/cm2。
3. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（1）Described in the pressure of air-flow crushing be 1~1.5MPa.
4. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（2）Described in ultralow temperature temperature be -40~-50 DEG C.
5. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（2）Described in microwave thawing microwave frequency be 900~1000MHz, microwave power is 200~300W.
6. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（3）Described in low-frequency ultrasonic waves processing in ultrasonic frequency be 20~40KHz, ultrasonic power density is 300~400W/L.
7. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（3）Described in high-frequency ultrasonic processing in ultrasonic frequency be 800~1000KHz, ultrasonic power density is 100~200W/
L。
8. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（3）Described in mid-frequency ultrasonic ripple processing in ultrasonic frequency be 350~500KHz, ultrasonic power density is 250~350W/L.
9. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
（3）Described in high-pressure pulse electric processing electric-field intensity be 20~30kV/cm, umber of pulse is 8~10.
10. the extracting method in high yield of salicoside in a kind of white willow branches and leaves according to claim 1, it is characterised in that step
Suddenly（4）Described in macroporous absorbent resin be HPD-826 type macroporous absorbent resins.
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| CN108084235A (en) * | 2018-01-25 | 2018-05-29 | 四川紫灵生物科技有限公司 | A kind of extract of willow bark and preparation method thereof |
| CN111647025A (en) * | 2020-06-18 | 2020-09-11 | 甘肃天顺植物科技有限公司 | Method for extracting, separating and refining salicin from willow |
| CN111647025B (en) * | 2020-06-18 | 2023-05-02 | 甘肃天顺植物科技有限公司 | Method for extracting, separating and refining salicin from willow |
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Application publication date: 20171219 |