CN107698650A - The extraction process of ursolic acid in a kind of old leaves of Kudingcha - Google Patents
The extraction process of ursolic acid in a kind of old leaves of Kudingcha Download PDFInfo
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- CN107698650A CN107698650A CN201711010407.2A CN201711010407A CN107698650A CN 107698650 A CN107698650 A CN 107698650A CN 201711010407 A CN201711010407 A CN 201711010407A CN 107698650 A CN107698650 A CN 107698650A
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- kudingcha
- ursolic acid
- old leaves
- extraction process
- extraction
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- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 title claims abstract description 29
- 229940096998 ursolic acid Drugs 0.000 title claims abstract description 29
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 241000629412 Ligustrum robustum Species 0.000 title claims abstract description 21
- 238000000605 extraction Methods 0.000 title claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 239000000284 extract Substances 0.000 claims description 13
- 241001122767 Theaceae Species 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002137 ultrasound extraction Methods 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000005238 degreasing Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 11
- 241001656831 Arctous alpina Species 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 6
- 201000007270 liver cancer Diseases 0.000 abstract description 5
- 208000014018 liver neoplasm Diseases 0.000 abstract description 5
- 239000013078 crystal Substances 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 150000002170 ethers Chemical class 0.000 abstract description 2
- 235000003325 Ilex Nutrition 0.000 abstract 2
- 241000209035 Ilex Species 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000078118 Ilex latifolia Species 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 235000008706 Ilex latifolia Nutrition 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 description 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 description 1
- 235000009685 Crataegus X maligna Nutrition 0.000 description 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 description 1
- 235000009486 Crataegus bullatus Nutrition 0.000 description 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 description 1
- 235000009682 Crataegus limnophila Nutrition 0.000 description 1
- 235000004423 Crataegus monogyna Nutrition 0.000 description 1
- 240000000171 Crataegus monogyna Species 0.000 description 1
- 235000002313 Crataegus paludosa Nutrition 0.000 description 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000576429 Forsythia suspensa Species 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The method that the present invention provides Ilex kudincha C. J. Tseng old leaf extraction ursolic acid, the black bearberry acid crystal of a large amount of high-purities is obtained using organic solvents such as ethanol and petroleum ethers, effectively increase ursolic acid recovery rate, reduce because old leaves of Kudingcha does not make full use of and caused by risk of environmental pollution.Human liver cancer cell HepG2 propagation can be significantly inhibited from the ursolic acid of Ilex kudincha C. J. Tseng old leaf extraction.
Description
Technical field
The invention belongs to medicinal plant extractive technique field, and in particular to ursolic acid in a kind of Cortex Ilicis Rotundae old leaves of Kudingcha
Extraction process.
Background technology
Because ursolic acid is complicated, artificial synthesized difficulty, be mostly extracted from natural plants it is isolated, such as female
Chastity, the capsule of weeping forsythia, hawthorn etc. are all the primary raw materials of ursolic acid.The extraction separation of ursolic acid mostly uses organic solvent method and silicagel column
Chromatography.Organic solvent method has the characteristics that process is cumbersome, content is low;Silica gel column chromatography brings certain be stranded in industrial operation
It is difficult.
Ilex Latifolia Thunb, it is Aquifoliaceae Ilex latifolia Thunb kind aiphyllium, is a kind of traditional pure natural health-care beverage in China
Good merchantable brand, there are the various effects such as clearing away heat and removing summer, the cough-relieving that wets one's whistle, suppression cancer anti-cancer, anti-aging, promoting blood circulation network.Contain bitter leaves in Ilex Latifolia Thunb
The Multiple components of saponin, amino acid, vitamin C, Polyphenols, flavonoids, caffeine etc. 200.Kudingcha starts about 25 after growth
In it, its young shoot tender leaf is still as the raw material for making tender tea, but its plucking time is very brief, quantity is few, cost of manufacture is high.Until
Spire is considerable rapidly after 25 days, and the food value of leaf is hardened, and turns into old leaf, old leaf plucking time is long, quantity is more, aboundresources, but can only use
It makes old leaf tea.Old leaf tea poor taste, does not endure repeated infusions compared with tender tea, and quality differs greatly.Therefore, old leaf is as bitter leaves
Tea accessory substance, often throws away as rubbish, causes the waste of resource.
Cortex Ilicis Rotundae old leaves of Kudingcha aboundresources, the wherein content of ursolic acid are more than 1%, are had now been found that as number
Natural plants of few ursolic acid content more than 1%, it is a kind of rare quality raw materials for being used to extract ursolic acid.
Have not yet to see the relevant report that ursolic acid is extracted from Cortex Ilicis Rotundae old leaves of Kudingcha.Therefore, study and establish from bitter leaves
The method of ursolic acid is extracted in tea old leaf to be helped to deeply develop using Ilex latifolia resource and reduce the production cost of ursolic acid.
The content of the invention
It is an object of the invention to provide a kind of extraction process with Cortex Ilicis Rotundae old leaves of Kudingcha, this method extraction process
Simply, cost can be preferably reduced, improves extraction efficiency.
The present invention uses following technical scheme:
The extraction process of ursolic acid, comprises the following steps in a kind of old leaves of Kudingcha:
(1)By old leaves of Kudingcha with boiling twice, each 1h, filter residue is washed with water to be filtered afterwards three times, and last filter residue is dried to constant weight
After crush, this step purpose be except desaccharification and soap-like matter;
(2)Tea powder and absolute ethyl alcohol are extracted, refluxing extraction or ultrasonic extraction can be used;
(3)Residue is removed by centrifugation in the ethanol solution just carried, and extract solution is concentrated under reduced pressure, and concentrate is transferred to pH=4 with sulfuric acid
Left and right, add water fully to precipitate, filter, dry sediment;
(4)Paste is further condensed into concentrate, petroleum ether is added into paste, three times, this step is intended to remove degreasing for washing
Class material;
(5)Paste is freeze-dried, obtains no water Kuding tea ursolic acid extract powder.
Preferably, the step(2)Middle old leaves of Kudingcha tea powder is 1 with absolute ethyl alcohol solid-to-liquid ratio:15;Reflux extracting time
For 12h, 85 DEG C of Extracting temperature or ultrasonic extraction time are 12h, 50 DEG C of Extracting temperature.
Preferably, the step(3)It is 10000Xg that RCF, which may be selected, in middle centrifugation, run duration for 15 min or
Person's RCF is 8000Xg, run duration 30min;Precipitation selection stands 20 hours.
Preferably, the step(4)The middle petroleum ether for adding 4 times of medicinal extract volume.
The advantageous effects of the present invention are the Cortex Ilicis Rotundae hardship for selecting aboundresources and being currently in the state of passing into disuse
Fourth tea old leaf is as raw material;Reagent environmental pollution used is small, during mainly use ethanol solution, oil can be used on a small quantity
Ethereal solution removes lipid material;Can be by the extracts active ingredients in old leaves of Kudingcha more by multi-reflow extraction or ultrasonic extraction
To be complete;The impurity in extract solution can be reduced by ultracentrifugal method so that purity is high, can improve product quality;Decompression
The ethanol of concentration is able to reclaim repeatable utilization, reduces the waste of alcohol solvent, reduces cost.
Brief description of the drawings
Fig. 1 is high performance liquid chromatography (HPLC) collection of illustrative plates of ursolic acid standard items.
Fig. 2 is high performance liquid chromatography (HPLC) collection of illustrative plates of obtained black bearberry acid crystal.
Fig. 3 is MTT test result of the obtained black bearberry acid crystal to human liver cancer cell HepG2.
Embodiment
With reference to specific embodiment, the present invention is further described.
Embodiment 1
The extraction process of ursolic acid, comprises the following steps in a kind of old leaves of Kudingcha:
(1)By old leaves of Kudingcha clean after with boiling twice, tealeaves is washed with water be dried to constant weight afterwards three times after crush;
(2)Using 100g tea powders and 4L absolute ethyl alcohols to be extracted, 100g:1L ultrasound 3h, after extract solution is poured out, add new
1L ethanol it is ultrasonic again, be repeated 3 times;
(3)It is 10000Xg that ethanol solution, which has just been carried, by RCF, run duration 15min, is centrifuged off residue, will
Extract solution is concentrated under reduced pressure, and by medicinal extract with after a small amount of ethanol dissolving, is transferred to pH=4 or so with the concentrated sulfuric acid, after adding water to stand 12h, subtracts
Pressure concentration;
(4)40ml petroleum ethers are added to medicinal extract in revolving bottle, three times, this step is intended to remove lipid material for washing;
(5)Paste is freeze-dried, obtains no g of water Kuding tea ursolic acid extract powder 7.49, wherein ursolic acid contains
Measure as 1.0062 g.
The ursolic acid that the method for the present invention is extracted is used as green acicular crystal, molecular formula:C30H48O3, molecular weight
456, identified by high performance liquid chromatography, compliance test result is carried out using human liver cancer cell HepG2.
(1)High performance liquid chromatography (HPLC):Take a small amount of ursolic acid standard items(Purchased from U.S. Sigma-Aldrich, numbering:
LOT:L03A6Y1)Dissolved respectively with methanol with the gained black bearberry acid product of embodiment 1, carry out HPLC analyses and compare.Determine bar
Part:INSTRUMENT MODEL:Shimadzu RESERVOIR TRAY LC-20A high performance liquid chromatographs, Shimadzu SPD-M20A type ultraviolet detections
Device, chromatographic column:sunfireTMC18(5.0 um, 4.6 mm X 150 mm), mobile phase:Methanol/water(90/10), flow velocity:0.1
ML/min, Detection wavelength:220 nm, temperature:Room temperature.The retention time of ursolic acid standard items is 5 min(Profiling results are shown in figure
1), obtained black bearberry acid product retention time is that (profiling results are shown in Fig. 2 to 4.6 min), both are basically identical.
(2)Human liver cancer cell HepG2 MTT experiments:HepG2 is the liver cancer cells from people.MTT experiment is a kind of detection
Cell survival and the method for growth.Its Cleaning Principle is that the succinate dehydrogenase in living cells mitochondria can make exogenous MTT also
Originally it was first a ceremonial jade-ladle, used in libation and was deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell, in 570nm
Its absorbance value is determined at wavelength, living cells quantity can be reflected indirectly.In the range of certain cell number, MTT crystallizes the amount to be formed
It is directly proportional to cell number.The method is widely used in large-scale screening anti-tumor medicine.Using Cortex Ilicis Rotundae old leaves of Kudingcha
Black bearberry acid product point 0,100,300,700,900 μ g/mL, five concentration groups of middle acquisition carry out processing 48 hours to HepG2,
700µg/mL(p<0.05)With 900 μ g/mL(p<0.01)Treatment group significantly inhibits HepG2 propagation(Profiling results are shown in Fig. 3).
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all skills in the present invention
On the basis of art scheme, those skilled in the art, which need not pay creative work, can make various modifications or deformation still at this
In the protection domain of invention.
Claims (4)
1. the extraction process of ursolic acid in a kind of Cortex Ilicis Rotundae old leaves of Kudingcha, it is characterised in that comprise the following steps:
(1)By old leaves of Kudingcha with boiling twice, each 1h, filter residue is washed with water to be filtered afterwards three times, and last filter residue is dried to constant weight
After crush, this step purpose be except desaccharification and soap-like matter;
(2)Tea powder and absolute ethyl alcohol are extracted, refluxing extraction or ultrasonic extraction can be used;
(3)Ethanol solution is just carried and residue is removed by centrifugation, extract solution has been concentrated under reduced pressure, it is left that concentrate with sulfuric acid is transferred to pH=4
The right side, add water fully to precipitate, filter, dry sediment;
(4)Paste is further condensed into concentrate, petroleum ether is added into paste, three times, this step is intended to remove degreasing for washing
Class material;
(5)Paste is freeze-dried, obtains no water Kuding tea ursolic acid extract powder.
2. the extraction process of ursolic acid in a kind of old leaves of Kudingcha according to claim 1, it is characterised in that the step
(2)Middle old leaves of Kudingcha tea powder is 1 with absolute ethyl alcohol solid-to-liquid ratio:15;The time 12h of refluxing extraction, 85 DEG C of Extracting temperature or
Ultrasonic extraction time 12h, 50 DEG C of Extracting temperature.
3. the extraction process of ursolic acid in a kind of old leaves of Kudingcha according to claim 1, it is characterised in that the step
(3)It is 10000Xg that RCF, which may be selected, in middle centrifugation, and run duration is 15 min or RCF is 8000Xg, fortune
Dynamic time 30min;Precipitation selection stands 20 hours.
4. the extraction process of ursolic acid in a kind of old leaves of Kudingcha according to claim 1, it is characterised in that the step
(4)The middle petroleum ether for adding 4 times of medicinal extract volume.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108576349A (en) * | 2018-05-03 | 2018-09-28 | 青岛科技大学 | A kind of natural plant extracts relieve the effect of alcohol sugar |
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CN1508149A (en) * | 2002-12-18 | 2004-06-30 | 中南大学 | Method for extracting total triterpenic acid, ursolic acid and oleanolic acid from Taiwan lectuce herb tea |
CN101016328A (en) * | 2007-02-09 | 2007-08-15 | 南京工业大学 | Method of separating and purifying ursolic acid and oleanolic acid |
CN101037467A (en) * | 2007-04-10 | 2007-09-19 | 福州大学 | Method for separating purifying ursolic acid from loquat leaf |
CN102558282A (en) * | 2012-01-16 | 2012-07-11 | 中国人民解放军第三军医大学 | Ursolic acid derivative and preparation method thereof |
CN102827001A (en) * | 2011-06-16 | 2012-12-19 | 东莞市岭奥生物科技有限公司 | Ilex kudingcha C.J.Tseng extract |
CN103694304A (en) * | 2013-12-28 | 2014-04-02 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for producing high-purity ursolic acid |
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2017
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CN1508149A (en) * | 2002-12-18 | 2004-06-30 | 中南大学 | Method for extracting total triterpenic acid, ursolic acid and oleanolic acid from Taiwan lectuce herb tea |
CN101016328A (en) * | 2007-02-09 | 2007-08-15 | 南京工业大学 | Method of separating and purifying ursolic acid and oleanolic acid |
CN101037467A (en) * | 2007-04-10 | 2007-09-19 | 福州大学 | Method for separating purifying ursolic acid from loquat leaf |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108576349A (en) * | 2018-05-03 | 2018-09-28 | 青岛科技大学 | A kind of natural plant extracts relieve the effect of alcohol sugar |
CN108576349B (en) * | 2018-05-03 | 2021-10-01 | 青岛科技大学 | Natural plant extract sugar for relieving alcoholism |
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