CN1796394A - Extractive form active ingredient of bitter bamboo, prepartion method and application - Google Patents
Extractive form active ingredient of bitter bamboo, prepartion method and application Download PDFInfo
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- CN1796394A CN1796394A CN 200410093600 CN200410093600A CN1796394A CN 1796394 A CN1796394 A CN 1796394A CN 200410093600 CN200410093600 CN 200410093600 CN 200410093600 A CN200410093600 A CN 200410093600A CN 1796394 A CN1796394 A CN 1796394A
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Abstract
This invention provides an extract containing effective components in pleioblastus amarus, its preparation method and its application in cosmetics and drugs. The main effective component in the extract is Taxiphyllin [2R-beta-D-glycopyranosyl-2-(p-hydroxyphenylacetonitrile)], which performs excellent antioxidant activity and tyrosinase inhibitory activity and is applicable in skin whitening cosmetics or drugs against hyperpigmentation disorders.
Description
Technical field
The present invention relates to subjects such as Natural Medicine Chemistry and biological chemistry, what be specifically related to extract from the herbal medicine bitter bamboo has the inhibiting effective constituent of tyrosinase activity, and preparation method thereof and the application in makeup, medicine.
Background technology
Tyrosine oxidase is the main rate-limiting enzyme in the melanocyte biosynthetic pathway.Most of materials of skin depigmentation that can make all block the generation of skin melanocyte by suppressing this enzymic activity, belong to tyrosine oxidase inhibition type Solu-Eze (Depigmenting agent).In recent years, the tyrosinase inhibitor of separating natural has obtained people's common concern from microorganism and plant amedica.It not only is used for the clinical treatment that pigment increases dermatoses (chloasma, freckle etc.), and can be used for makeup the colour of skin is brightened.
In general, can suppress this enzymic activity with the similar single phenolic compound quinhydrones of the substrate of tyrosine oxidase, many single phenol or polyphenolic substances with similar structure of functional groups also can the restraint of tyrosinase activity.But the external preparation unstable chemcial property of quinhydrones and other phenolic compound, oxidation stain easily also has this class material to cause the report of the permanent hickie of skin in addition, has limited the development and application of this compounds.Vitamins C and arbutin are additives relatively more commonly used in the current skin-lightening cosmetic.But vitamins C equally also is very unstable, can't directly add in the product, adopts ascorbic derivative (as ascorbic phosphoric acid salt etc.) usually.And arbutin finds also that in research in recent years its restraint of tyrosinase activity is not very stable.Therefore, seek the focus that activity is high, safe tyrosinase inhibitor is still present research.
This has the existing many-sided development and use of plant of affluent resources at home and abroad bamboo.Aspect cosmetics production, except raw material as some makeup subsidiary productss, series products as the packing box of the handle of lash curler, eye-lash and blush brush etc. and some makeup, bamboo also is used as effective additive of natural cosmetics and functional cosmetics with the form of bamboo class extract, have preserve moisture, whiten, multiple function such as anti-ageing, anti-inflammatory, cleaning and hair care.For example, gondola Erbasol company extracts from bamboo shoots and obtains alpha hydroxy acid and have the cell of renewal, keep the effect of pH equilibrated, is applied to the production of moisture-keeping shower cream; The extract that Japan NOEVIA company obtains from a kind of bamboo that blooms can effectively suppress the generation of the T3 isomerase of tyrosine oxidase in the B16 melanophore, is applied to the novel whitening cosmetic development.The domestic Folium Bambosae flavone product of then being developed by the Sheng Shi biological products company limited of Anji, Zhejiang can be used as the natural biological antioxidant and is applied in the multiple industries such as medicine, health care and makeup.
Less relatively to the research of bitter bamboo (Pleioblastus amarus Keng (Keng) f. (Gramineae)) at present.Shoot ofBitter Bamboo has heat-clearing in the Chinese medicine record, dehumidifying makes eye bright, treatment order pain, aphtha, functions such as burn.
Summary of the invention
One object of the present invention is, a kind of Chinese herbal medicine extract is provided, and it can be used as tyrosinase inhibitor, and effective, have no side effect.
Another object of the present invention is, the said herbal medicine preparation method of extract is provided.
Of the present invention also have a purpose to be, the above-mentioned purposes of Chinese herbal medicine extract in makeup and pharmaceutical industries as tyrosinase inhibitor is provided.
Provided by the invention from bitter bamboo (Pleioblastus amarus Keng (Keng) f. (Gramineae)), particularly in the extract for preparing in the shoot ofBitter Bamboo, main effective constituent is Taxiphyllin, 2R-β-D-glucopyranosyl-2-p-hydroxybenzylcyanide, and molecular formula is C
14H
17NO
7(molecular weight is 311) can account for more than 98% of extract total amount, and structure is:
Extract of the present invention is separated purification can obtain white needle (chloroform-methanol), water-soluble, methyl alcohol.Point sample launches on prefabricated silica-gel plate, and with the iodine colour developing, spot colors becomes green gradually by yellow, becomes blueness again, and places in air, and color does not disappear; When developping agent is chloroform-methanol (2: 1); During ethyl acetate-methyl alcohol (1: 3) benzene-methyl alcohol (2: 1), R
fValue is respectively 0.56,0.17,0.42.Through electrospray ionization mass spectrometry (ESI-MS), high resolution electron impact mass spectra (HREI-MS),
13C NMR and
1Data such as H NMR show that the molecular formula of this compound is C
14H
17NO
7Ultimate analysis shows that this compound contains an itrile group.
1H-NMR (400MHZ, methyl-sulphoxide-d
6) show, this compound exist the benzene ring structure that a contraposition replaces (δ 7.32 and δ 6.82, J=8.6Hz, 4H) and hydroxyl (δ 9.84, and δ 5.23, and δ 5.05, δ 4.98 and δ 4.55,5H).
1H-NMR hydrogen spectrum data and the Cyanogenic glucoside taxiphyllin data consistent of having delivered.
13C-NMR carbon spectrum data are as shown in table 1.
Table 1 bitter bamboo extract
13C-NMR carbon spectrum data
| C | The bitter |
| CN | |
| 1 2 3 4 5 6 7 1’ 2’ 3’ 4’ 5’ 6’ | 118.5 123.0 128.9 115.2 157.8 115.2 128.9 65.9 99.7 72.9 76.3 69.8 77.1 61.1 |
The concrete preparation method of Chinese herbal medicine extract of the present invention is:
Method one:
1. shoot ofBitter Bamboo obtains medicinal extract with 50～90% times of volume of ethanol refluxing extraction 2 times;
Shoot ofBitter Bamboo medicinal extract be dissolved in water (about 5～10 times of volumes) centrifugal, filter;
3. filtrate is with propyl carbinol or chloroform, the extraction of ethyl acetate equal solvent;
4. the medicinal extract silicagel column is used the chloroform-methanol wash-out;
5. recrystallization.
Method two:
1. shoot ofBitter Bamboo obtains medicinal extract with 50～90% alcohol reflux of 10 times of volumes 2 times;
2. shoot ofBitter Bamboo medicinal extract be dissolved in water (about 5～10 times of volumes);
3. the aqueous solution adds 95% ethanol sedimentation, and placement is spent the night;
4. filtrate thickening filtration, and with chloroform, sherwood oil or etc. the propyl carbinol solvent extraction;
5. use absorption with macroporous adsorbent resin, with 30～60% ethanol elutions;
6. silica gel column chromatography is used the chloroform-methanol gradient elution;
7. with recrystallizations such as methyl alcohol or acetone, dehydrated alcohols.
Method three:
1. shoot ofBitter Bamboo obtains medicinal extract with 50～90% alcohol reflux of 10 times of volumes 2 times;
Shoot ofBitter Bamboo medicinal extract be dissolved in water (about 8～12 times of times of volumes) centrifugal, filter;
3. filtrate concentrates back macroporous resin wash-out, alcohol-water gradient elution a little;
4. elutriant separates with silica gel column chromatography, and solvent for use is chloroform-methanol (2: 1～5: 1);
5. recrystallization.
Extract of active ingredient in hairy bamboo of the present invention has good antioxidant activity, has tangible tyrosinase inhibitory activity simultaneously.
Extract of the present invention and vitamins C and arbutin are made tyrosinase activity suppress contrast under different concns, the results are shown in Figure 1, when reactant concn was higher, extract of active ingredient in hairy bamboo (YF4332) and vitamins C (Vc) activity level were approaching substantially, are higher than arbutin as can be seen; In low strength range, vitamins C and arbutin are active to descend rapidly, and extract of active ingredient in hairy bamboo (YF4332) descends slowly.Therefore, the sphere of action of extract of active ingredient in hairy bamboo (YF4332) is more wide in range than vitamins C and arbutin, helps the reduction of formulation cost.
From foregoing as can be known, extract of active ingredient in hairy bamboo of the present invention extremely is suitable for the makeup that the colour of skin brightens, or pigment increases the dermatoses medicine.
Description of drawings
The accompanying drawing that comprises among the application is a component part of specification sheets, and accompanying drawing and specification sheets and claims one are used from explanation flesh and blood of the present invention, are used for understanding better the present invention.In the accompanying drawing:
Fig. 1 is extract of active ingredient in hairy bamboo of the present invention (YF4332) and vitamins C and the tyrosinase activity inhibition contrast synoptic diagram of arbutin under different concns.
Fig. 2 be in melanophore arbutin and extract of active ingredient in hairy bamboo of the present invention (YF4332) tyrosinase inhibitory activity and concentration concern synoptic diagram.
Fig. 3 is that arbutin and extract of active ingredient in hairy bamboo of the present invention (YF4332) melanocyte generate the synoptic diagram that concerns that suppresses with concentration in melanophore.
Embodiment
The present invention is further elaborated below in conjunction with embodiment, but these embodiment do not constitute any restriction to the present invention.
Be prepared according to separation method one: the ethanol extract 882g of shoot ofBitter Bamboo, with 5～10 times of water gaging dissolution precipitations, filtrate filtered is with extractions such as the solvent of 2～5 times of amounts such as chloroform, ethyl acetate, propyl carbinols, extraction liquid is through silica gel column chromatography, with chloroform-methanol (10: 1～1: 1) wash-out, get 1812.7mg bitter bamboo extract behind the recrystallization.
Embodiment 2
Be prepared according to separation method two: the ethanol extract 700g of shoot ofBitter Bamboo, with 5～10 times of water dissolution, the 95% ethanol placement that adds 2～4 times is spent the night.Filter, use propyl carbinol or chloroform, the extraction of sherwood oil equal solvent behind the filtrate thickening filtration.Extraction liquid is through the dissolve with methanol after-filtration, and macroporous adsorbent resin is extremely colourless with 30～60% ethanol elution on the filtrate, gets fraction 26g.Behind dissolve with methanol, go up silica gel column chromatography, use the chloroform-methanol gradient elution, behind recrystallizations such as methyl alcohol or acetone, dehydrated alcohol, get white solid, i.e. extract of active ingredient in hairy bamboo 0.68g.
In the method, activeconstituents extract of active ingredient in hairy bamboo (YF4332) yield is 1 ‰; Its purity can reach 99.8%.
Embodiment 3
Be prepared according to separation method three: the ethanol extract 500g of shoot ofBitter Bamboo, the water dissolution, the precipitation that add 8～12 times of volumes, filtrate after the centrifuging is concentrated slightly, last macroporous adsorbent resin alcohol-water gradient elution gets fraction 14.8g (can at 231.8nm detect extract of active ingredient in hairy bamboo (YF4332) content with the high-efficient liquid phase chromatogram HPLC analysis this moment is 73.4%).Go up silica gel column chromatography then,, separate out needle-like crystal behind the recrystallization, i.e. extract of active ingredient in hairy bamboo (YF4332) 157.6mg with chloroform-methanol (2: 1～5: 1) wash-out.
Embodiment 4
Anti-oxidant activity is analyzed
Adopt DPPH free radical scavenging method to measure anti-oxidant activity.
Measuring method: 0.1ml contains the sample of different concns additive and the abundant mixing of DPPH ethanolic soln of 3.9ml, and room temperature is placed and measured 517 nanometer absorbances (OD517nm) after 30 minutes.
Table 1: anti-oxidant activity
| Reactant | IC 50(％) |
| Vitamins C Root of Kirilow Rhodiola oiliness extract Root of Kirilow Rhodiola aqueous extract Flos Chrysanthemi extract *Green tea extract *Green tea aqueous extract extract of active ingredient in hairy bamboo (YF4332) | 0.0003 0.0004 0.005 1.51 0.0007 0.05 0.1 |
Embodiment 5
External tyrosinase activity suppresses
Measuring principle: under the effect of tyrosine oxidase, levodopa (L-DOPA) is oxidized to tan dopachrome (DOPAchrome).
Measuring method: 0.5ml contains the sample of different concns additive and 10u/ml tyrosine oxidase solution and the abundant mixing of 1.5ml damping fluid of 0.5ml, puts 30 ℃ of water-baths and hatches 20 minutes.Then in each test tube, add the 0.2%L-DOPA of 1.0ml, 30 ℃ of water-bath accurate responses 5 minutes, at once with the absorption peak of spectrophotometer in 475nm place mensuration dopachrome,
Table 2: tyrosinase inhibitory activity
| Reactant | IC 50(μM) |
| Azelaic acid vitamin C sodium ascorbyl phosphate vitamin C ursin kojic acid extract of active ingredient in hairy bamboo (YF4332) | 19521 7540 159 327 35 32 |
Embodiment 6
Tyrosinase activity suppresses in the melanophore
Measuring method: the B16 melanophore is cultivated after 24 hours and is added extract of active ingredient in hairy bamboo (YF4332), cultivates the back through 48 hours and with physiological saline substratum is rinsed well.Add Triton X-100 (Triton X-100) and hatch 30min, pipette 0.2ml, in remaining cell, add Dopa, when hatching 30min for 37 ℃, measure OD475 with the quantitative cell protein of triketohydrindene hydrate at 37 ℃.
Tested the inhibition in melanophore of bitter bamboo extract to tyrosinase activity.The result as shown in Figure 2.Data show that extract of active ingredient in hairy bamboo (YF4332) has the effect of restraint of tyrosinase activity and melanocyte really in melanophore.
Embodiment 7
The melanophore melanocyte generates and suppresses
Measuring method: add extract of active ingredient in hairy bamboo (YF4332) in the melanophore after cultivating 24 hours, cultivated the back through 48 hours and substratum is rinsed well with phosphate buffered saline buffer (PBS).Add trypsin digestion cell.Remove supernatant after centrifugal, pipette 0.2ml equally with the quantitative cell protein of triketohydrindene hydrate, add NaOH and boil 20min in remaining cell, 400 nanometer absorbances (OD400) are measured in the cooling back.
Tested the bitter bamboo extract in melanophore to melanogenic inhibition.The result as shown in Figure 3.Data show that extract of active ingredient in hairy bamboo (YF4332) has the melanogenic effect of inhibition really in melanophore.
Claims (11)
1, a kind of extract of active ingredient in hairy bamboo is characterized in that, main effective constituent wherein is 2R-β-D-glucopyranosyl-2-p-hydroxybenzylcyanide, and molecular formula is C
14H
17NO
7, structural formula as shown in Equation 1.
2, effective component extracts as claimed in claim 1 extracts acquisition from shoot ofBitter Bamboo.
3, effective component extracts as claimed in claim 1 is characterized in that outward appearance is a white powder.
4, a kind of preparation method of extract of active ingredient in hairy bamboo is characterized in that comprising the following steps:
The bitter bamboo raw material more than 2 times or 2 times, is obtained medicinal extract with alcohol reflux, with the medicinal extract aqueous precipitation, centrifugal, filtration, filtrate is through extraction or concentrate the back wash-out, and the process silica gel column chromatography separates again, and recrystallization obtains extract of active ingredient in hairy bamboo.
5, preparation method as claimed in claim 4, the alcohol concn that wherein is used for refluxing extraction is 50～90%.
6, preparation method as claimed in claim 4, wherein the consumption of water is 5～10 times of volumes of medicinal extract during the medicinal extract aqueous precipitation.
7, preparation method as claimed in claim 4, the sorbent material that adopts in the time of wherein with the filtrate wash-out is a macroporous resin.
8, preparation method as claimed in claim 4, wherein silica gel column chromatography separation solvent for use is chloroform, methyl alcohol mixed liquor.
9, a kind of preparation method of extract of active ingredient in hairy bamboo is characterized in that comprising the following steps:
With the bitter bamboo raw material with 50～90% alcohol reflux more than 2 times or 2 times, obtain medicinal extract, the water dissolution that medicinal extract is added 5～10 times of volumes, add concentration 95% or 95% above ethanol sedimentation in the aqueous solution, leave standstill the back thickening filtration, with for example propyl carbinol, sherwood oil, the extraction of chloroform equal solvent, use absorption with macroporous adsorbent resin then, ethanol elution with 30～60%, carry out silica gel column chromatography with the chloroform methanol mixed solution as eluent again and separate, obtain extract of active ingredient in hairy bamboo behind the recrystallization.
10, the application of extract of active ingredient in hairy bamboo as claimed in claim 1 in makeup.
11, the application of extract of active ingredient in hairy bamboo as claimed in claim 1 in preparation pigment increase dermatoses medicine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100936003A CN100352825C (en) | 2004-12-24 | 2004-12-24 | Extractive form active ingredient of bitter bamboo, prepartion method and application |
| HK06108885A HK1088609A1 (en) | 2004-12-24 | 2006-08-10 | The use of an extraction of the effective components from bitter bamboo |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100936003A CN100352825C (en) | 2004-12-24 | 2004-12-24 | Extractive form active ingredient of bitter bamboo, prepartion method and application |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101127300A Division CN101112354B (en) | 2004-12-24 | 2004-12-24 | Method for preparing extract of active ingredient in hairy bamboo |
| CN2007101127315A Division CN101112355B (en) | 2004-12-24 | 2004-12-24 | Method for preparing extract of active ingredient in hairy bamboo |
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| Publication Number | Publication Date |
|---|---|
| CN1796394A true CN1796394A (en) | 2006-07-05 |
| CN100352825C CN100352825C (en) | 2007-12-05 |
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| Application Number | Title | Priority Date | Filing Date |
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|---|---|
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| HK (1) | HK1088609A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669788A (en) * | 2016-03-18 | 2016-06-15 | 昆明理工大学 | Method for extracting active compound from bamboo shoots and application thereof |
| CN112159439A (en) * | 2020-09-28 | 2021-01-01 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | Taxus cyanogen glucoside compound and preparation method and application thereof |
-
2004
- 2004-12-24 CN CNB2004100936003A patent/CN100352825C/en active Active
-
2006
- 2006-08-10 HK HK06108885A patent/HK1088609A1/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669788A (en) * | 2016-03-18 | 2016-06-15 | 昆明理工大学 | Method for extracting active compound from bamboo shoots and application thereof |
| CN105669788B (en) * | 2016-03-18 | 2018-11-27 | 昆明理工大学 | A kind of method and its application for extracting reactive compound from bamboo shoots |
| CN112159439A (en) * | 2020-09-28 | 2021-01-01 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | Taxus cyanogen glucoside compound and preparation method and application thereof |
| CN112159439B (en) * | 2020-09-28 | 2023-11-21 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | Taxocyanum glycoside compound and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN100352825C (en) | 2007-12-05 |
| HK1088609A1 (en) | 2006-11-10 |
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