CN106242974A - A kind of Flos Moutan is extracted method and the application of ethyl vanillate - Google Patents
A kind of Flos Moutan is extracted method and the application of ethyl vanillate Download PDFInfo
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- CN106242974A CN106242974A CN201610621160.7A CN201610621160A CN106242974A CN 106242974 A CN106242974 A CN 106242974A CN 201610621160 A CN201610621160 A CN 201610621160A CN 106242974 A CN106242974 A CN 106242974A
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- China
- Prior art keywords
- flos moutan
- ethyl vanillate
- eluent
- ethanol
- colourless
- Prior art date
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- MWAYRGBWOVHDDZ-UHFFFAOYSA-N Ethyl vanillate Chemical compound CCOC(=O)C1=CC=C(O)C(OC)=C1 MWAYRGBWOVHDDZ-UHFFFAOYSA-N 0.000 title claims abstract description 114
- 241000628997 Flos Species 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 92
- 241000736199 Paeonia Species 0.000 claims abstract description 22
- 235000006484 Paeonia officinalis Nutrition 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 19
- 239000011347 resin Substances 0.000 claims abstract description 19
- 239000000284 extract Substances 0.000 claims abstract description 17
- 238000004440 column chromatography Methods 0.000 claims abstract description 14
- 239000004367 Lipase Substances 0.000 claims abstract description 12
- 102000004882 Lipase Human genes 0.000 claims abstract description 12
- 108090001060 Lipase Proteins 0.000 claims abstract description 12
- 235000019421 lipase Nutrition 0.000 claims abstract description 12
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 47
- 239000003480 eluent Substances 0.000 claims description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000012141 concentrate Substances 0.000 claims description 30
- 239000003208 petroleum Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000012153 distilled water Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- -1 ether Compound Chemical class 0.000 claims description 7
- 235000006085 Vigna mungo var mungo Nutrition 0.000 claims description 6
- 240000005616 Vigna mungo var. mungo Species 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000004537 pulping Methods 0.000 claims description 6
- 230000001629 suppression Effects 0.000 claims description 6
- 244000236658 Paeonia lactiflora Species 0.000 claims description 3
- 235000008598 Paeonia lactiflora Nutrition 0.000 claims description 3
- 241000233805 Phoenix Species 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001429 chelating resin Polymers 0.000 claims description 2
- 239000003350 kerosene Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 abstract description 15
- 229960001243 orlistat Drugs 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000000605 extraction Methods 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 49
- 102000019280 Pancreatic lipases Human genes 0.000 description 15
- 108050006759 Pancreatic lipases Proteins 0.000 description 15
- 229940116369 pancreatic lipase Drugs 0.000 description 15
- 240000005001 Paeonia suffruticosa Species 0.000 description 11
- 235000003889 Paeonia suffruticosa Nutrition 0.000 description 11
- 229940040461 lipase Drugs 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 235000019626 lipase activity Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- YNGNVZFHHJEZKD-UHFFFAOYSA-N (4-nitrophenyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=CC=C([N+]([O-])=O)C=C1 YNGNVZFHHJEZKD-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 229940086609 Lipase inhibitor Drugs 0.000 description 4
- 150000002759 monoacylglycerols Chemical class 0.000 description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- OKDJKYFRYBDUDG-UHFFFAOYSA-N 1-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethanol Chemical compound C(C)(C)(CC(C)(C)C)C1=CC=C(OCCOC(C)O)C=C1 OKDJKYFRYBDUDG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
- MQVRGDZCYDEQML-UHFFFAOYSA-N Astragalin Natural products C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 MQVRGDZCYDEQML-UHFFFAOYSA-N 0.000 description 1
- 206010013954 Dysphoria Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000002607 hemopoietic effect Effects 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JPUKWEQWGBDDQB-QSOFNFLRSA-N kaempferol 3-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O JPUKWEQWGBDDQB-QSOFNFLRSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000018791 negative regulation of catalytic activity Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Seasonings (AREA)
Abstract
The present invention provides a kind of method extracting ethyl vanillate in Flos Moutan, the method is with peony petal as raw material, by heating and refluxing extraction peony petal contains the active component of ethyl vanillate, after extraction, macroporous resin column chromatography, silica gel column chromatography and recrystallization process, obtain ethyl vanillate.Using the method extracting ethyl vanillate in the Flos Moutan of present invention offer can obtain the ethyl vanillate that purity is higher, its purity is up to more than 95%.During ethyl vanillate extracts, the medicine used is common medicine, and production cost is low；Meanwhile, the macroporous resin in the organic solvent such as ethanol and chromatographic column is the most reusable, free from environmental pollution, reduces production cost further, it is adaptable to promote on a large scale and application.By the ethyl vanillate obtained by the method that the present invention provides, there is the activity more higher than orlistat, it is possible to be applied to prepare appetrol or include suppressing the medicine of lipase active.
Description
Technical field
The present invention relates to technical field of plant extraction, particularly relate to a kind of Flos Moutan is extracted the method for ethyl vanillate and
Application.
Background technology
Obesity (obesity) refers to there is the most overweight or that fat deposit is blocked up disease to a certain extent, it is common that by
In body fat, particularly triglyceride accumulation too much causes.After deliberation, contained in the food of wedging fat is all by water
Solution becomes monoacylglycerol and free fatty, monoacylglycerol and free fatty to be absorbed by the body in intestinal, and in human body
Recombine fat, if the hyperliposis eaten, then can form substantial amounts of synthctic fat in vivo, thus cause the heap of fat
Long-pending, ultimately result in obesity.In human body intestinal canal, when fat digestion and absorption, necessary enzyme is lipase, and lipase mostlys come from
Pancreas, is also also from stomach simultaneously, therefore, in food fat digest and assimilate the most relevant with the activity of lipase, namely
Say, if fat relevant with the activity of lipase.
In current diet products, lipase inhibitor is common slimming medicine, and lipase inhibitor can be effective
The activity of suppression lipase, thus reduce the synthesis of fat, reach the effect that treatment is fat, thus, it is found that and use effective
Lipase inhibitor be the focus studying Bariatric now, and from natural product, find safe and effective lipase press down
Preparation, has important social benefit and huge economic benefit.
Paeonia suffruticosa (Paeonia suffruticosa Andrews) is a kind of rare flower originating in China, has higher
Ornamental value and medical value.In terms of medical value, Paeonia suffruticosa has and effect of blood, hemopoietic, removing heat from blood and heat-clearing and toxic substances removing etc.,
Can be used in treating the blood fire second of the three ten-day periods of the hot season, dysphoria with smothery sensation etc..Meanwhile, modern pharmacology research is it is also shown that contain astragalin, Cortex Moutan in Paeonia suffruticosa
Spend glycosides, form stricture of vagina India glycosides and the aminoacid of multiple needed by human, trace element and vitamin etc..The sight that Paeonia suffruticosa is had by it
Reward is worth can bring certain economic benefit when the florescence, but after the florescence, substantial amounts of Paeonia suffruticosa withers, decays, only Paeonia suffruticosa
Root brings certain economic benefit as Chinese crude drug.Certainly also there is the sideline production that Flos Moutan is made foodstuff, but due to deeply
The backwardness of process technology, the processed utilization of the most a small amount of Flos Moutan, therefore, for improving the utilization rate of Paeonia suffruticosa, more and more
People studies composition and the application of Paeonia suffruticosa, but, the method extracting ethyl vanillate from Paeonia suffruticosa has no report.
Summary of the invention
The present invention provides method and the application extracting ethyl vanillate in a kind of Flos Moutan, thus realizes carrying from Flos Moutan
Taking ethyl vanillate, the method production cost that the present invention provides is low, and extraction efficiency is high, and to environment without severe contamination, it is adaptable to
Promote on a large scale and application.
The present invention provides a kind of method extracting ethyl vanillate in Flos Moutan, described method to include:
Win peony petal, clean, drain；
Described peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping, obtains Flos Moutan
Serosity, wherein, the mass/volume of described peony petal and described ethanol is than for 1g:2-4ml；
Described Flos Moutan serosity is joined in the ethanol solution that concentration is 75% and is heated to reflux, obtain backflow, wherein,
Described Flos Moutan serosity is 1:4-6 with the volume ratio of described ethanol；
Described backflow is filtrated to get Flos Moutan extracting solution；
Described Flos Moutan extracting solution using Rotary Evaporators evaporation, obtains solid matter and ethanol, described ethanol reclaims
Stand-by；
In described solid matter, add distilled water, heating for dissolving at 50-70 DEG C, obtain mixture, wherein, described solid
Material is 1:2-5 with the volume ratio of described distilled water；
Adding normal hexane in described mixture to extract, collect aqueous phase extract, wherein, described mixture is with described
The volume ratio of normal hexane is 1:1-1.5；
Described aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；
Described concentrate distilled water is carried out macroporous resin column chromatography, until lower column liquid is eluted to colourless；
Described lower column liquid be eluted to colourless after, be 40%, 70%, 90% by concentration respectively and straight alcohol solution is successively to institute
State concentrate and again carry out macroporous resin column chromatography, until lower column liquid is eluted to colourless, collect all eluents in this step
A, standby；
Described eluent a merges, concentrates；
By petroleum ether and petroleum ether and the ethyl acetate that volume ratio is 15:1, the described eluent a after concentrating is carried out successively
Silica gel column chromatography, until lower column liquid is eluted to colourless；
Described lower column liquid be eluted to colourless after, by the petroleum ether that volume ratio is 10:1 and ethyl acetate to described eluent a
Again carry out silica gel column chromatography, until lower column liquid is eluted to colourless, collect the eluent b in this step, standby；
Described eluent b concentrates after merging, the product cooling after concentration, sucking filtration crystallization, and is tied by petroleum ether
Crystallization compound；
Described crystalline compounds vacuum dehydrating at lower temperature obtains ethyl vanillate.
Preferably, the condition being heated to reflux described in is: heating-up temperature is 50-70 DEG C, and reflow's cycle is 2-3 time, returns every time
The stream time is 2-4h.
Preferably, described macroporous resin is Amberlite XAD7HP resin.
Preferably, described eluent a merges, concentrates as being concentrated into without ethanol taste after described eluent a merging；Described eluting
Liquid b concentrates after merging after merging for described eluent b and is concentrated into without kerosene taste.
Preferably, described peony petal is peaceful red peony or the petal of phoenix white peony.
The application of a kind of ethyl vanillate, described ethyl vanillate is according to the method system extracting ethyl vanillate in Flos Moutan
Standby, described ethyl vanillate is for preparing appetrol or including suppressing the medicine of lipase active.
The technical scheme that embodiments of the invention provide can include following beneficial effect:
The invention provides a kind of method extracting ethyl vanillate in Flos Moutan, this extracting method includes: win Paeonia suffruticosa
Petal, cleans, drains；Described peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping,
To Flos Moutan serosity, wherein, the mass/volume of described peony petal and described ethanol is than for 1g:2-4ml；By described Flos Moutan
Serosity joins in the ethanol solution that concentration is 75% and is heated to reflux, and obtains backflow, and wherein, described Flos Moutan serosity is with described
The volume ratio of ethanol is 1:4-6；Described backflow is filtrated to get Flos Moutan extracting solution；Described Flos Moutan extracting solution is used rotation
Turning evaporimeter evaporation, obtain solid matter and ethanol, described ethanol reclaims stand-by；Distilled water is added in described solid matter,
Heating for dissolving at 50-70 DEG C, obtains mixture, and wherein, described solid matter is 1:2-5 with the volume ratio of described distilled water；To
Described mixture adds normal hexane extract, collect aqueous phase extract, wherein, described mixture and the body of described normal hexane
Long-pending ratio is 1:1-1.5；Described aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；Described concentrate distilled water is entered
Row macroporous resin column chromatography, until lower column liquid is eluted to colourless；Described lower column liquid be eluted to colourless after, by concentration be respectively
40%, 70%, 90% and straight alcohol solution successively described concentrate is carried out again macroporous resin column chromatography, until lower column liquid is washed
Take off to colourless, collect all eluent a in this step, standby；Described eluent a merges, concentrates；Successively with petroleum ether and body
Petroleum ether and ethyl acetate that long-pending ratio is 15:1 carry out silica gel column chromatography, until lower column liquid is washed to the described eluent a after concentrating
Take off to colourless；Described lower column liquid be eluted to colourless after, by the petroleum ether that volume ratio is 10:1 and ethyl acetate to described eluent a
Again carry out silica gel column chromatography, until lower column liquid is eluted to colourless, collect the eluent b in this step, standby；Described eluent
B concentrates after merging, the product cooling after concentration, sucking filtration crystallization, and obtains crystalline compounds by petroleum ether；Described crystallization
Compound vacuum dehydrating at lower temperature obtains ethyl vanillate.Use the method energy that ethyl vanillate is provided in the Flos Moutan of present invention offer
Access the ethyl vanillate that purity is higher, and its purity is up to more than 95%.During ethyl vanillate extracts, made
Medicine be common medicine, production cost is low；Meanwhile, the macroporous resin in the organic solvent such as ethanol and chromatographic column all can weigh
Multiple use, free from environmental pollution, reduce production cost further, it is adaptable to promote on a large scale and application.Thered is provided by the present invention
The ethyl vanillate that extracted of method there is the activity more higher than orlistat, it is possible to be applied to prepare appetrol or include pressing down
The medicine of lipase active processed.
It should be appreciated that it is only exemplary and explanatory, not that above general description and details hereinafter describe
The present invention can be limited.
Accompanying drawing explanation
Accompanying drawing herein is merged in description and constitutes the part of this specification, it is shown that meet the enforcement of the present invention
Example, and for explaining the principle of the present invention together with description.
In order to be illustrated more clearly that the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
In having technology to describe, the required accompanying drawing used is briefly described, it should be apparent that, for those of ordinary skill in the art
Speech, on the premise of not paying creative work, it is also possible to obtain other accompanying drawing according to these accompanying drawings.
The Flos Moutan that Fig. 1 provides for the embodiment of the present invention is extracted the method flow schematic diagram of ethyl vanillate.
Detailed description of the invention
Here will illustrate exemplary embodiment in detail, its example represents in the accompanying drawings.Explained below relates to
During accompanying drawing, unless otherwise indicated, the same numbers in different accompanying drawings represents same or analogous key element.Following exemplary embodiment
Described in embodiment do not represent all embodiments consistent with the present invention.On the contrary, they are only with the most appended
The example of the apparatus and method that some aspects that described in detail in claims, the present invention are consistent.
Refer to accompanying drawing 1, accompanying drawing 1 shows the method extracting ethyl vanillate in the Flos Moutan that the embodiment of the present invention provides
Schematic flow sheet, the description of specific examples below is all based on accompanying drawing 1.
Embodiment 1
S101: win later stage in full bloom fresh peony petal, clean, drain；
S102: the peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping under room temperature,
To Flos Moutan serosity, wherein, the mass/volume of peony petal and ethanol is than for 1g:2ml；
S103: being joined in the ethanol solution that concentration is 75% by Flos Moutan serosity and be heated to reflux, heating-up temperature is 50 DEG C,
Reflow's cycle is 2 times, and each return time is 2h, obtains backflow, and wherein, Flos Moutan serosity is 1:4 with the volume ratio of ethanol；
S104: backflow is filtrated to get Flos Moutan extracting solution；
S105: Flos Moutan extracting solution uses Rotary Evaporators evaporation be spin-dried for ethanol, obtains solid matter and ethanol, ethanol
Reclaim stand-by；
S106: in solid matter add distilled water, heating for dissolving at 50 DEG C, obtain mixture, wherein, solid matter with
The volume ratio of distilled water is 1:2；
S107: add normal hexane in mixture and extract, collect aqueous phase extract, wherein, mixture and normal hexane
Volume ratio be 1:1；
S108: aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；
S109: concentrate distilled water is carried out macroporous resin column chromatography, until lower column liquid is eluted to colourless；
S110: described lower column liquid be eluted to colourless after, be 40%, 70%, 90% by concentration respectively and straight alcohol solution depends on
Secondary described concentrate carrying out macroporous resin column chromatography again, until lower column liquid is eluted to colourless, that collects in this step is all
Eluent a, standby；
S111: described eluent a merging, concentration；
S112: successively by petroleum ether and petroleum ether that volume ratio is 15:1 and ethyl acetate to the described eluent after concentrating
A carries out silica gel column chromatography, until lower column liquid is eluted to colourless；
S113: described lower column liquid be eluted to colourless after, petroleum ether and ethyl acetate with volume ratio is 10:1 are washed described
De-liquid a carries out silica gel column chromatography again, until lower column liquid is eluted to colourless, collects the eluent b in this step, standby；
Concentrate after S114: described eluent b merging, the product cooling after concentration, sucking filtration crystallization, and obtain by petroleum ether
To crystalline compounds；
S115: described crystalline compounds vacuum dehydrating at lower temperature obtains ethyl vanillate.
Embodiment 2
S201: win later stage in full bloom fresh peaceful red peony petal, clean, drain；
S202: the peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping under room temperature,
To Flos Moutan serosity, wherein, the mass/volume of peony petal and ethanol is than for 1g:4ml；
S203: being joined in the ethanol solution that concentration is 75% by Flos Moutan serosity and be heated to reflux, heating-up temperature is 70 DEG C,
Reflow's cycle is 3 times, and each return time is 4h, obtains backflow, and wherein, Flos Moutan serosity is 1:6 with the volume ratio of ethanol；
S204: backflow is filtrated to get Flos Moutan extracting solution；
S205: Flos Moutan extracting solution uses Rotary Evaporators evaporation be spin-dried for ethanol, obtains solid matter and ethanol, ethanol
Reclaim stand-by；
S206: in solid matter add distilled water, heating for dissolving at 70 DEG C, obtain mixture, wherein, solid matter with
The volume ratio of described distilled water is 1:5；
S207: add normal hexane in mixture and extract, collect aqueous phase extract, wherein, mixture and normal hexane
Volume ratio be 1:1.5；
S208: aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；
S209: concentrate distilled water is carried out macroporous resin column chromatography, until lower column liquid is eluted to colourless；
S210: described lower column liquid be eluted to colourless after, be 40%, 70%, 90% by concentration respectively and straight alcohol solution depends on
Secondary described concentrate carrying out macroporous resin column chromatography again, until lower column liquid is eluted to colourless, that collects in this step is all
Eluent a, standby；
S211: described eluent a merging, concentration；
S212: successively by petroleum ether and petroleum ether that volume ratio is 15:1 and ethyl acetate to the described eluent after concentrating
A carries out silica gel column chromatography, until lower column liquid is eluted to colourless；
S213: described lower column liquid be eluted to colourless after, petroleum ether and ethyl acetate with volume ratio is 10:1 are washed described
De-liquid a carries out silica gel column chromatography again, until lower column liquid is eluted to colourless, collects the eluent b in this step, standby；
Concentrate after S214: described eluent b merging, the product cooling after concentration, sucking filtration crystallization, and obtain by petroleum ether
To crystalline compounds；
S215: described crystalline compounds vacuum dehydrating at lower temperature obtains ethyl vanillate.
Embodiment 3
S301: win later stage in full bloom fresh phoenix white peony petal, clean, drain；
S302: the peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping under room temperature,
To Flos Moutan serosity, wherein, the mass/volume of peony petal and ethanol is than for 1g:3ml；
S303: being joined in the ethanol solution that concentration is 75% by Flos Moutan serosity and be heated to reflux, heating-up temperature is 60 DEG C,
Reflow's cycle is 3 times, and each return time is 3h, obtains backflow, and wherein, Flos Moutan serosity is 1:5 with the volume ratio of ethanol；
S304: backflow is filtrated to get Flos Moutan extracting solution；
S305: Flos Moutan extracting solution uses Rotary Evaporators evaporation be spin-dried for ethanol, obtains solid matter and ethanol, ethanol
Reclaim stand-by；
S306: in solid matter add distilled water, heating for dissolving at 60 DEG C, obtain mixture, wherein, solid matter with
The volume ratio of distilled water is 1:4；
S307: add normal hexane in mixture and extract, collect aqueous phase extract, wherein, mixture and normal hexane
Volume ratio be 1:1；
S308: aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；
S309: concentrate distilled water is carried out macroporous resin column chromatography, until lower column liquid is eluted to colourless；
S310: described lower column liquid be eluted to colourless after, be 40%, 70%, 90% by concentration respectively and straight alcohol solution depends on
Secondary described concentrate carrying out macroporous resin column chromatography again, until lower column liquid is eluted to colourless, that collects in this step is all
Eluent a, standby；
S311: described eluent a merging, concentration；
S312: successively by petroleum ether and petroleum ether that volume ratio is 15:1 and ethyl acetate to the described eluent after concentrating
A carries out silica gel column chromatography, until lower column liquid is eluted to colourless；
S313: described lower column liquid be eluted to colourless after, petroleum ether and ethyl acetate with volume ratio is 10:1 are washed described
De-liquid a carries out silica gel column chromatography again, until lower column liquid is eluted to colourless, collects the eluent b in this step, standby；
Concentrate after S314: described eluent b merging, the product cooling after concentration, sucking filtration crystallization, and obtain by petroleum ether
To crystalline compounds；
S315: described crystalline compounds vacuum dehydrating at lower temperature obtains ethyl vanillate.
The embodiment of the present invention compound to being extracted by embodiment 2 carries out GC-MS (Gas Chromatography-
Mass Spectrometer, i.e. gas chromatography-mass spectrum) analyze, wherein, chromatographic column condition is: Rtx-5MS quartz capillary column
(0.25mm × 30m, 0.25 μm)；Injector temperature is 230 DEG C, temperature programming, heating schedule be 60 DEG C keep 3min, with 3 DEG C/
Min rises to 90 DEG C, rises to 250 DEG C with 10 DEG C/min, keeps 15min；Carrier gas: He；Flow velocity: 1mL/min；Pressure: 57.5kPa；
Sample size: 1 μ L；Split ratio: 50:1.Mass Spectrometry Conditions is EI ionization source；Detection electrostatic pressure 1.2kv；Ion source temperature 200 DEG C；Connect
Mouth temperature 250 DEG C；Solvent delay time: 2min；ACQ mode: Scan；Scanning speed: 1668/s；Mass scan range: m/z
50～500amu.By NIST (the National Institute of Standards and with ethyl vanillate
Technology, i.e. National Institute of Standards and Technology) standard diagram preliminary comparison analyze learn, the embodiment of the present invention carries
The compound that the method for confession is extracted is corresponding with the ethyl vanillate of NIST, further by the chromatograph of compound Yu standard sample
Scheme to compare with mass spectrum to confirm that the compound that the method that the embodiment of the present invention provides is extracted is ethyl vanillate.
By probing into the perfume (or spice) that the method extracting ethyl vanillate from Flos Moutan provided by the embodiment of the present invention is extracted
Ethyl oxalate can suppress the activity of tryrosinase, embodiments provides ethyl vanillate with orlistat to tyrosine
The evaluation methodology of inhibition of enzyme activity, concrete evaluation methodology is:
One, the preparation of experiment reagent
(1) concentration is the preparation of hydrochloric acid solution of 0.01mol/L
Measure the concentrated hydrochloric acid 2.1ml that concentration is 11.9mol/L to be placed in volumetric flask, in volumetric flask, add distilled water dilute
Release to 250ml, i.e. obtain the hydrochloric acid solution that concentration is 0.01mol/L.
(2) concentration be 0.01mol/L, pH=8.2 Tris-HCl (Tris (hydroxymethyl) aminomethane,
I.e. three (methylol) aminomethane) preparation of buffer solution
1. weigh 12.11g Tris (trishydroxymethylaminomethane) to be placed in beaker；
2. in beaker, add 800ml distilled water, shake up；
3. adding configured good concentration in 22.9ml (1) is the hydrochloric acid solution of 0.01mol/L, and regulates pH value of solution and be
8.2；
4. solution is settled to 1L, i.e. obtains the Tris-HCl buffer solution that concentration is 0.01mol/L, pH=8.2.
(3) preparation of pancreatic lipase
Weigh 15mg pancreatic lipase and join 4ml PBS (phosphate buffer saline, phosphate buffered saline(PBS))
Middle formation mixed solution, is centrifuged 5min under conditions of rotating speed is 9000r/min after the mixed solution formed vibration 5min, stays
Taking supernatant, supernatant is the pancreatic lipase solution of configuration.
(4) concentration is the preparation of sodium acetate solution of 5mol/L, pH=5
Weigh 68mg sodium acetate with electronic balance to be dissolved in 70ml water, after being 5.0 with the pH of acetic acid regulation sodium acetate solution
It is settled to 100ml, then obtains the sodium acetate solution that concentration is 5mol/L, pH=5.
(5) mass concentration is the preparation of p-nitrophenyl laurate solution of 0.1%
Taking concentration in 99ml above-mentioned (4) is the sodium acetate solution of 5mol/L, pH=5, by the TritonX-100 (2-of 1ml
(2-[4-(1,1,3,3-Tetramethylbutyl) phenoxy] ethoxy) ethanol, i.e. Triton X-100)
Join in sodium acetate solution, and in boiling water, heat 2min；After heating, take liquid 10ml, by the p-nitrophenyl of 10mg
Base laurate joins in liquid, obtains the p-nitrophenyl laurate solution that mass concentration is 0.1%.
(6) ethyl vanillate and the preparation of orlistat solution:
It is 1:1 configuration dimethyl sulfoxide and deionized water according to volume ratio, forms dimethyl sulfoxide aqueous solution, sub-to diformazan respectively
Sulfone aqueous solution adds ethyl vanillate and orlistat, is configured to concentration and is ethyl vanillate solution and the Ao Li of 0.5mg/ml
Take charge of his solution.
(7) preparation of blank
Blank is the dimethyl sulfoxide aqueous solution that above-mentioned (6) have configured.
Two, pancreatic lipase inhibition test
Respectively at EP (Ethylene propylene, the i.e. epoxy resin) Guan Zhongfen that three identical volumes are 1.5ml
Do not add the blank of 100 μ l, ethyl vanillate solution and orlistat solution, and add the most successively in above-mentioned solution respectively
Entering 150 μ l pancreatic lipase, 200 μ l concentration are Tris-HCl buffer solution and the 250 μ l mass concentrations of 0.01mol/L, pH=8.2
It is the p-nitrophenyl laurate solution of 0.1%, thus forms blank liquid, external pancreatic lipase activity detection liquid respectively
With the Activity determination liquid configured by orlistat.Blank liquid, external pancreatic lipase activity are detected liquid and by orlistat
The Activity determination liquid of configuration is all placed in the constant temperature oven of 37 DEG C reaction 2 hours, and reaction after terminating by microplate reader at wavelength is
Blank, external pancreatic lipase activity detection liquid and the Activity determination liquid configured by orlistat is measured respectively under 475nm light
Absorbance, parallel assay 3 times, calculate pancreatic lipase activity IC50 (half maximal inhibitory
Concentration, i.e. 503nhibiting concentration), computing formula is:
I=[1-(C-D)/(A-B)] × 100%, wherein, I is suppression ratio；A is not for having inhibitor (i.e. without ethyl vanillate
Or without orlistat) in the presence of absorbance；B be only p-nitrophenyl laurate solution time absorbance；C is pancreas
Lipase and p-nitrophenyl laurate solution absorbance in the presence of inhibitor (ethyl vanillate or orlistat)；
D is not have the absorbance in the presence of pancreatic lipase.
Being calculated by above-mentioned formula and learn, the ethyl vanillate solution of 0.5mg/mL is 27.9 to the IC50 value of pancreatic lipase
The orlistat of ± 1.3%, 0.5mg/mL is 38.2 ± 1.1% to the IC50 value of pancreatic lipase, it is possible to explanation, in concentration
Under conditions of 0.5mg/mL, ethyl vanillate is significantly greater than orlistat and lives pancreatic lipase the suppression of pancreatic lipase activity
The suppression of property.
Orlistat is a kind of long-acting specific gastrointestinal lipase inhibitor, it is possible to stoping triglyceride hydrolysis is can
The free fatty absorbed and monoacylglycerol so that it is do not absorbed, thus reduce energy intake, control body weight, and the present invention
The ethyl vanillate prepared by method extracting ethyl vanillate in the Flos Moutan that embodiment provides has more aobvious than orlistat
The feature of the suppression pancreatic lipase activity write, therefore, it is sweet that the ethyl vanillate prepared by the embodiment of the present invention has prevention equally
Oil three esters are hydrolyzed to the effect of absorbable free fatty and monoacylglycerol.Further, prepared by the embodiment of the present invention
Ethyl vanillate has effect of fat-reducing, it is possible to be applied to prepare appetrol or include suppressing the medicine of lipase active.
Those skilled in the art are considering description and are putting into practice here after disclosure of the invention, will readily occur to its of the present invention
Its embodiment.The application is intended to any modification, purposes or the adaptations of the present invention, these modification, purposes or
Person's adaptations is followed the general principle of the present invention and includes the undocumented common knowledge in the art of the present invention
Or conventional techniques means.Description and embodiments is considered only as exemplary, and true scope and spirit of the invention are by following
Claim is pointed out.
It should be appreciated that the invention is not limited in precision architecture described above and illustrated in the accompanying drawings, and
And various modifications and changes can carried out without departing from the scope.The scope of the present invention is only limited by appended claim.
Claims (6)
1. the method extracting ethyl vanillate in a Flos Moutan, it is characterised in that described method includes:
Win peony petal, clean, drain；
Described peony petal after draining joins in the ethanol solution that concentration is 75% and mashes pulping, obtains Flos Moutan slurry
Liquid, wherein, the mass/volume of described peony petal and described ethanol is than for 1g:2-4ml；
Described Flos Moutan serosity is joined in the ethanol solution that concentration is 75% and is heated to reflux, obtain backflow, wherein, described
Flos Moutan serosity is 1:4-6 with the volume ratio of described ethanol；
Described backflow is filtrated to get Flos Moutan extracting solution；
Described Flos Moutan extracting solution using Rotary Evaporators evaporation, obtains solid matter and ethanol, described ethanol reclaims stand-by；
In described solid matter, add distilled water, heating for dissolving at 50-70 DEG C, obtain mixture, wherein, described solid matter
It is 1:2-5 with the volume ratio of described distilled water；
Adding normal hexane in described mixture to extract, collect aqueous phase extract, wherein, described mixture is just own with described
The volume ratio of alkane is 1:1-1.5；
Described aqueous phase extract is carried out concentrating under reduced pressure, obtains concentrate；
Described concentrate distilled water is carried out macroporous resin column chromatography, until lower column liquid is eluted to colourless；
Described lower column liquid be eluted to colourless after, be 40%, 70%, 90% by concentration respectively and straight alcohol solution is successively to described dense
Contracting thing carries out macroporous resin column chromatography again, until lower column liquid is eluted to colourless, collects all eluent a in this step, standby
With；
Described eluent a merges, concentrates；
By petroleum ether and petroleum ether and the ethyl acetate that volume ratio is 15:1, the described eluent a after concentrating is carried out silica gel successively
Column chromatography, until lower column liquid is eluted to colourless；
Described lower column liquid be eluted to colourless after, by the petroleum ether that volume ratio is 10:1 and ethyl acetate to described eluent a again
Carry out silica gel column chromatography, until lower column liquid is eluted to colourless, collect the eluent b in this step, standby；
Described eluent b concentrates after merging, the product cooling after concentration, sucking filtration crystallization, and obtains crystallization by petroleum ether
Compound；
Described crystalline compounds vacuum dehydrating at lower temperature obtains ethyl vanillate.
The method extracting ethyl vanillate in Flos Moutan the most according to claim 1, it is characterised in that described in be heated to reflux
Condition be: heating-up temperature is 50-70 DEG C, and reflow's cycle is 2-3 time, and each return time is 2-4h.
The method extracting ethyl vanillate in Flos Moutan the most according to claim 1, it is characterised in that described macroporous resin
For Amberlite XAD7HP resin.
The method extracting ethyl vanillate in Flos Moutan the most according to claim 1, it is characterised in that described eluent a
Merge, concentrate as being concentrated into without ethanol taste after described eluent a merging；Described eluent b concentrates as described eluent b after merging
It is concentrated into after merging without kerosene taste.
The method extracting ethyl vanillate in Flos Moutan the most according to claim 1, it is characterised in that described peony petal
For peaceful red peony or the petal of phoenix white peony.
6. the application of an ethyl vanillate, it is characterised in that described ethyl vanillate is according to any one in claim 1-5
Prepared by the method extracting ethyl vanillate in described Flos Moutan, described ethyl vanillate is used for preparing appetrol or including suppression
The medicine of lipase active.
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| CN112791127A (en) * | 2021-02-18 | 2021-05-14 | 瑞莱茵(北京)生物科技有限责任公司 | Peony petal extract and preparation method and application thereof |
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| WO2012134214A2 (en) * | 2011-03-31 | 2012-10-04 | 연세대학교 산학협력단 | Composition containing extracts of the fruit of hovenia dulcis thunb as an active ingredient for preventing and treating bone diseases |
| CN104921997A (en) * | 2015-06-23 | 2015-09-23 | 山东省分析测试中心 | Ultrahigh-pressure pressure extraction method of peony flower and whitening antioxidant essence prepared thereby |
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| WO2012134214A2 (en) * | 2011-03-31 | 2012-10-04 | 연세대학교 산학협력단 | Composition containing extracts of the fruit of hovenia dulcis thunb as an active ingredient for preventing and treating bone diseases |
| CN104921997A (en) * | 2015-06-23 | 2015-09-23 | 山东省分析测试中心 | Ultrahigh-pressure pressure extraction method of peony flower and whitening antioxidant essence prepared thereby |
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| CN112791127A (en) * | 2021-02-18 | 2021-05-14 | 瑞莱茵(北京)生物科技有限责任公司 | Peony petal extract and preparation method and application thereof |
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