CN1116264C - Method for separating reseveratrol from resveratrol glucoside and application thereof - Google Patents
Method for separating reseveratrol from resveratrol glucoside and application thereof Download PDFInfo
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- CN1116264C CN1116264C CN 00121100 CN00121100A CN1116264C CN 1116264 C CN1116264 C CN 1116264C CN 00121100 CN00121100 CN 00121100 CN 00121100 A CN00121100 A CN 00121100A CN 1116264 C CN1116264 C CN 1116264C
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- 238000000034 method Methods 0.000 title claims abstract description 19
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 235000021283 resveratrol Nutrition 0.000 title claims abstract description 8
- 229940016667 resveratrol Drugs 0.000 title claims abstract description 8
- 229930182478 glucoside Natural products 0.000 title claims description 4
- -1 resveratrol glucoside Chemical class 0.000 title abstract description 3
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims abstract description 43
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
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- 235000003202 Reynoutria sachalinensis Nutrition 0.000 claims abstract description 15
- 230000008025 crystallization Effects 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000004587 chromatography analysis Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- RUOKEYJFAJITAG-UHFFFAOYSA-N Resveratroloside Natural products OC1C(O)C(O)C(CO)OC1OC(C=C1)=CC=C1C=CC1=CC(O)=CC(O)=C1 RUOKEYJFAJITAG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 150000008131 glucosides Chemical class 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000287 crude extract Substances 0.000 claims description 2
- 238000012163 sequencing technique Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 235000013305 food Nutrition 0.000 abstract description 6
- 238000000746 purification Methods 0.000 abstract description 6
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- 238000010898 silica gel chromatography Methods 0.000 abstract description 3
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- 229940079593 drug Drugs 0.000 abstract 1
- 150000002338 glycosides Chemical class 0.000 abstract 1
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- 239000003480 eluent Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
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- HSTZMXCBWJGKHG-UHFFFAOYSA-N (E)-piceid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(C=CC=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- HSTZMXCBWJGKHG-CUYWLFDKSA-N trans-piceid Polymers O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-CUYWLFDKSA-N 0.000 description 2
- SIMYWHHAEQQGEH-TYYBGVCCSA-N 5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol Chemical compound C1=CC(O)=CC=C1C=CC1=CC(O)=CC(O)=C1.C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 SIMYWHHAEQQGEH-TYYBGVCCSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- HSTZMXCBWJGKHG-CENDIDJXSA-N Piceid Natural products OC[C@@H]1O[C@@H](Oc2cc(O)cc(C=Cc3ccc(O)cc3)c2)[C@H](O)[C@H](O)[C@H]1O HSTZMXCBWJGKHG-CENDIDJXSA-N 0.000 description 1
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- 235000009392 Vitis Nutrition 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 230000002526 effect on cardiovascular system Effects 0.000 description 1
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- 150000002085 enols Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
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- 208000026435 phlegm Diseases 0.000 description 1
- HSTZMXCBWJGKHG-OUUBHVDSSA-N piceide Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(C=CC=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-OUUBHVDSSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229960003764 polydatin Drugs 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a method of separating resveratrol and resveratrol glycoside from traditional Chinese medicinal herb giant knotweed rhizome and applications of resveratrol and resveralrol glycoside as medicine, health-care products or food, drinks and health-care additives. The method comprises: the giant knotweed rhizomes are extracted with organic solvent and through concentration, silica gel column chromatography, crystallization and recrystallization to obtain resveratrol and resveratrol glocoside with purity up to over 97% and high yields respectively up to over 70% and over 60%. The obtain products can be directly used as medicines and health products. The separation and purification method provided by the present invention has the advantages of convenient process, easy operation, safety, low cost and convenient large-scale production.
Description
The present invention relates to the separation method and the application thereof of trans-resveratrol and polidatin, particularly relate to from Chinese medicine polygoni cuspidati,radix stem and separate the application of the method for trans-resveratrol and polidatin and trans-resveratrol and polidatin as healthcare products or food, beverage, health-care additive.
Early existing people finds that the generation of cardiovascular disorder and the consumption of red wine are negative correlation.Find (E.H.Siemann and L.L.Creasy:Am.J.Enol.Vitic.43:49-50 after deliberation; 1992) be wherein contained trans-resveratrol (Resveratrol) and polidatin (Polydatin or Piceid) to the cardiovascular physiologically active substance that shields in the red wine.Discover in addition, this compounds also have the thrombosis of preventing, protection liver, anti-oxidant, remove free radical, anti-inflammatory, anti-some fungi and bacterium and effect (Yu Chuanlin etc., Pharmacology and Clinics of Chinese Materia Medica, 1994,10 (2): 33 such as anticancer; Dan Chunwen, Acta Pharmaceutica Sinica, 1988,23 (5): 394; Kubo morals etc., foreign medical science pharmacy fascicle, 1982:3; Meishiang J et al.Science 1997, Vol 275:218-220).But obtaining trans-resveratrol and glucoside thereof at present mainly is chemical synthesis process, exists problems such as complex process, cost height.
Giant knotweed (Polygonum Caspidatum Sieb et Zace) is China's tradition herbal medicine, contains more rich (content is different and different with the place of production) trans-resveratrol and polidatin.Giant knotweed is mainly used to treat arthralgia, jaundice due to damp-heat, amenorrhoea, cough ant phlegm, burn due to hot liquid or fire at present, falls wresting wound, carbuncle sore tumefacting virus etc.The composition of giant knotweed is very complicated, also contains multiple materials such as anthraquinone analog compound, flavonoid compound, naphthoquinones, polysaccharide, amino acid, trace element, lipid acid.Therefore, separation and purification trans-resveratrol and polidatin have bigger difficulty from giant knotweed.Extraction trans-resveratrol and polidatin are detected in the clear 60-9455 of Japanese Patent (1985) from giant knotweed, and the method extraction process of this patent disclosure is numerous and diverse, and have used dangerous bigger ether as solvent.Especially, only can obtain containing the end product of trans-resveratrol and polidatin mixture with this patented method, purity is lower.
The present invention is intended to extract trans-resveratrol and polidatin from giant knotweed, and a kind of technology is easy, quick, easy to operate, purity is high, cost hangs down also energy scale operation separation and method of purification are provided.Another object of the present invention is with the application as medicine, healthcare products or food, beverage, health-care additive of trans-resveratrol and polidatin.
Below be particular content of the present invention:
1, extracts
After dry giant knotweed rhizome pulverized, with can with the miscible organic solvent extraction of water 2 times, 5 times of extracting solvent load at every turn and be medicinal powder weight, united extraction liquid, underpressure distillation is concentrated into 1/20 of former extracting liquid volume.Add this enriched material volume 1-2 water doubly in the gained enriched material again, transfer pH to 7.5-8.0 with alkaline matter.Use the ethyl acetate extraction secondary of 5 times and 4 times volumes more respectively, merge extraction liquid twice, underpressure distillation is concentrated into the 1/15-1/20 of extraction liquid volume, and the enriched material of last gained is a crude extract, as the raw material that is further purified.
The miscible organic solvent of described and water means: methyl alcohol, ethanol, propyl alcohol, Virahol, acetone and these solvents make up arbitrarily.
2, separation and purification
Separate and purifying with crystallization process with column chromatography, trans-resveratrol and glucoside thereof separate with the sequencing difference of collecting the column chromatography elutriant, contain trans-resveratrol in the elution fraction of collecting earlier, contain polidatin in the elution fraction that collect the back.The chromatography column weighting material is a silica gel, and the chromatography elutriant is a chloroform: methyl alcohol=4～8: 1; Or ethyl acetate: ethanol=90～100: 0～10, preferred 95: 5.
Collect in the column chromatography for the first time and at room temperature leave standstill after the polidatin elution fraction concentrates, separate out crystallization, use methyl alcohol: chloroform=1: 8～10 recrystallizations can obtain purity up to the crystallization more than 97%.
Trans-resveratrol needs through the secondary silica gel column chromatography.At first collecting trans-resveratrol wash-out component for the first time in the column chromatography concentrates, the last sample raw material of silica gel column chromatography carries out chromatography once more as the second time, the chromatography elutriant is a chloroform: ethyl acetate=70～100: 20～30, the secondary elutriant is concentrated, leaves standstill under the room temperature, separate out resveratrol recrystallized, use acetone: chloroform=1: 8～10 recrystallizations also obtains purity up to the crystallization more than 97%.
More than solvent, eluent in each operation reclaim easily, and can use repeatedly, thereby reduce cost.
After mother liquor behind each time recrystallization all can be waited until and be merged with next giant knotweed powder extracting solution, separation and purification was used once more.
3, preparation
After acceptable assistant agent, mixed with excipients on polidatin or trans-resveratrol or both mixtures and food or the medicine, make various formulations with suitable technology, as pulvis, granule, tablet, capsule, solution, salve, creme etc., as medicine, healthcare products, makeup etc.Also can be used as foodstuff additive adds food, beverage, makes various forms of protective foodss, beverage, drinks.
Separation purification method technology provided by the invention is easy, processing ease, safety, and is with low cost, is convenient to scale operation, products therefrom purity height.
Following examples further describe in detail the present invention, make to help to understand content of the present invention.
Embodiment 1
1, extracts
After dry giant knotweed rhizome pulverized 40 mesh sieves, take by weighing 300g, add 1500ml acetone, stirring at room was soaked 24 hours, carried out suction filtration then, and filter residue soaks in the same way, extracts once with 1500ml acetone again, with twice filtrate merging.Learn through the high pressure liquid chromatography quantitative analysis: contain trans-resveratrol 0.75g in the above-mentioned gained filtrate, polidatin 5.16g.
Above-mentioned gained filtrate heating is evaporated to 180ml, adds 300ml distilled water, transfer pH to 8.0 with 2NNaOH again.Use 2.5L, 2.0L ethyl acetate extraction twice then, merge twice extraction liquid, be concentrated into 200ml.Learn through the high pressure liquid chromatography quantitative analysis: contain trans-resveratrol 0.70g in this filtrate, polidatin 4.81g.
2, chromatography
Take by weighing 460g column chromatography silica gel (100-200 order), with the suspend diameter of packing into of ethyl acetate is 60mm, in the glass chromatography column of long 500mm, behind this elutriant balance columns, 200ml ethyl acetate extraction concentrated solution in the step 1 is added on this post, use eluent ethyl acetate, eluent flow rate is 20-25ml/min, begin to collect elutriant when pigment has just begun to wash out, collect 300ml for every bottle, preceding 3 bottles contain trans-resveratrol and yellow pigment.The 6th bottle of beginning polidatin washed out, and the 16th bottle of polidatin wash-out almost completely.
The high density elutriant that merges the 7-12 bottle is concentrated into 500ml, and leave standstill more than the 24hr at the dark place of room temperature, has mass crystallization to separate out in the visual cell.Incline and mother liquor (this mother liquor and 13-16 bottle elutriant can be waited until and next batch ethyl ester extraction liquid merges the back reconcentration, upper prop separates, so cyclical operation), get crystallization 3.82g, use methyl alcohol: chloroform=1: 10 recrystallization, can get polidatin 3.25g, yield 63%, through high pressure liquid chromatographic analysis, purity is 98%.
Take by weighing 120g column chromatography silica gel (100-200 order), use chloroform: the suspend diameter of packing into of ethyl acetate=4: 1 is 30mm, in the glass chromatography column of long 500mm, pillar is after balance, the 1-3 bottle elutriant of collecting in the column chromatography first time is condensed into 25ml to be added on this pillar, use chloroform: ethyl acetate=4: 1 is carried out wash-out, eluent flow rate is controlled at 5ml/min, collection contains the elutriant of trans-resveratrol, then elutriant is concentrated into crystallization and separates out, and leave standstill at the dark place of room temperature, to be crystallized incline when complete mother liquor, acetone is used in crystallization again: chloroform=1: 10 recrystallization, purity is 97.5% trans-resveratrol 0.54g, yield 72%.
Embodiment 2
Take by weighing 460g column chromatography silica gel (100-200 order), use chloroform: methyl alcohol=5: the 1 suspension diameter of packing into is 60mm, in the glass chromatography column of long 500mm, be added on this post by the resulting ethyl acetate extraction concentrated solution of embodiment 1 method 50ml after the balance, use chloroform: methyl alcohol=5: 1 elutriant wash-outs, elution speed is 25ml/min.Collect the elutriant of trans-resveratrol and polidatin respectively, the collection liquid of polidatin is separated out through condensing crystal, and the crystallization of separating out is again through methyl alcohol: chloroform=1: 10 is the recrystallization secondary repeatedly, purity 98.6% polidatin 0.81g.
Embodiment 3
1, extracts
After dry giant knotweed rhizome pulverized 40 mesh sieves, take by weighing 1kg, add 5L95% ethanol, 60 ℃ are stirred and soaked 24 hours, carry out suction filtration then, and filter residue soaks in the same way, extracts once with 5L95% ethanol again, with twice filtrate merging.Learn through the high pressure liquid chromatography quantitative analysis: contain trans-resveratrol 2.63g in the above-mentioned gained filtrate, polidatin 16.80g.
Above-mentioned gained filtrate heating is evaporated to 600ml, adds 1000ml distilled water, transfer pH to 7.8 with 2NNaOH again.Use 8L, 6.5L ethyl acetate extraction twice then, merge twice extraction liquid, be evaporated to 785ml.Learn through the high pressure liquid chromatography quantitative analysis: contain trans-resveratrol 2.5g in this concentrated solution, polidatin 15.6g.
2, chromatography
The 785ml concentrated solution is divided into four times carries out column chromatography, chromatography and crystallization and recrystallization method are by embodiment 1 described carrying out.The recrystallization of trans-resveratrol and polidatin is after four coarse crystallization are merged, the disposable recrystallization that carries out.
The final polidatin 11.3g that from the 1kg giant knotweed, obtains recrystallization, yield 67%; Through high pressure liquid chromatographic analysis, purity is 98.3%; Obtain the trans-resveratrol 1.95g of recrystallization, yield 74%; Through high pressure liquid chromatographic analysis, purity is 98.1%.
Embodiment 4
With polidatin 3mg with make granule after the 1g glucose powder mixes, in the Aluminium Foil Package of packing into the pack.
Embodiment 5
With the polidatin 3mg and the dark-coloured capsule of packing into after 0.25g starch mixes.
Embodiment 6
With the trans-resveratrol 2mg and the dark-coloured capsule of packing into after the 0.25g dextrin mixes.
Embodiment 7
Polidatin is pressed 15mg/L to add in the red wine.
Embodiment 8
Trans-resveratrol 10mg/L is added in the Sucus Vitis viniferae, make nourishing drink.
Claims (4)
1, separate the method for trans-resveratrol and polidatin from Chinese medicine polygoni cuspidati,radix stem, its step is as follows:
A. with the giant knotweed powder with organic solvent extraction that can be miscible with water, the underpressure distillation concentrated extracting solution adds distilled water again, transfers pH to 7.5-8.0; Concentrate with ethyl acetate extraction and underpressure distillation again, obtain crude extract, as the raw material that is further purified;
B. separate and purifying with crystallization process with column chromatography, trans-resveratrol and glucoside thereof separate with the sequencing difference of collecting the column chromatography elutriant, contain trans-resveratrol in the elution fraction of collecting earlier, contain polidatin in the elution fraction that collect the back; The chromatography column weighting material is a silica gel, and the chromatography elutriant is a chloroform: methyl alcohol=4～8: 1 or ethyl acetate: ethanol=90～100: 0～10;
At room temperature leave standstill after the elutriant of the polidatin component that back in the first time chromatography is collected concentrates, separate out the polidatin crystallization, carry out recrystallization then;
The trans-resveratrol elution fraction of at first collecting in the column chromatography first time is concentrated, carry out the chromatography second time, the chromatography elutriant is a chloroform: ethyl acetate=70～100: 20～30, and the secondary elutriant is concentrated, leaves standstill under the room temperature, separate out resveratrol recrystallized, carry out recrystallization then.
2, the method for described separation trans-resveratrol of claim 1 and polidatin, what wherein said extraction giant knotweed was used means with the miscible organic solvent of water: methyl alcohol, ethanol, propyl alcohol, Virahol, acetone and these solvents make up arbitrarily.
3, the method for described separation trans-resveratrol of claim 1 and polidatin, wherein said first time, the component proportions of chromatography elutriant was a chloroform: methyl alcohol=5: 1, or ethyl acetate: ethanol=95: 5; Be used for separating the chromatography second time of trans-resveratrol, the component proportions of elutriant is a chloroform: ethyl acetate=4: 1.
4, the method for described separation trans-resveratrol of claim 1 and polidatin, wherein said crystallization method are that elutriant is concentrated, and leave standstill at dark place under the room temperature, separate out to crystallization; Trans-resveratrol recrystallization solvent for use is an acetone: chloroform=1: 8～10; Polidatin recrystallization solvent for use is a methyl alcohol: chloroform=1: 8～10.
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| CN 00121100 CN1116264C (en) | 2000-07-20 | 2000-07-20 | Method for separating reseveratrol from resveratrol glucoside and application thereof |
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| CN 00121100 CN1116264C (en) | 2000-07-20 | 2000-07-20 | Method for separating reseveratrol from resveratrol glucoside and application thereof |
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| CN1116264C true CN1116264C (en) | 2003-07-30 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519343B (en) * | 2009-01-21 | 2011-09-07 | 安徽农业大学 | Method for preparaing trans-resveratrol by hydrolyzing trans-polydatin |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0503657D0 (en) | 2005-02-22 | 2005-03-30 | Fluxome Sciences As | Metabolically engineered cells for the production of resveratrol or an oligomeric or glycosidically-bound derivative thereof |
| CN100432090C (en) | 2005-12-13 | 2008-11-12 | 深圳海王药业有限公司 | I crystal form 3, 4', 5-trihydroxy-3-beta-D-heteroside |
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| CN108821953A (en) * | 2018-05-30 | 2018-11-16 | 上海华堇生物技术有限责任公司 | A kind of polishing purification method of natural resveratrol |
| CN110041384A (en) * | 2019-04-29 | 2019-07-23 | 苏州海科医药技术有限公司 | A kind of preparation method of II phase metabolin trans-resveratrol glucuronic acid and its application in the identification of rat cylinder metabolism-ure |
| CN118436556B (en) * | 2024-05-07 | 2025-01-28 | 广州市白云区白云美湾上研国际化妆品研究院 | A resveratrol supramolecule and its preparation method and application in preparing cosmetics |
-
2000
- 2000-07-20 CN CN 00121100 patent/CN1116264C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519343B (en) * | 2009-01-21 | 2011-09-07 | 安徽农业大学 | Method for preparaing trans-resveratrol by hydrolyzing trans-polydatin |
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| CN1277954A (en) | 2000-12-27 |
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