CN103110549B - Preparation method of olive leaf extract microemulsion containing hydroxytyrosol - Google Patents
Preparation method of olive leaf extract microemulsion containing hydroxytyrosol Download PDFInfo
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Abstract
The invention discloses a preparation method of an olive leaf extract microemulsion containing hydroxytyrosol and application of the olive leaf extract microemulsion. The preparation method comprises the following steps of: extracting an olive leaf extract rich in hydroxytyrosol from olive leaves; and carrying out appropriate microemulsion processing on the extract to improve the stability and enlarge the adaptability. The preparation method disclosed by the invention has the outstanding advantage of preparing the olive leaf extract microemulsion product rich in hydroxytyrosol and can be widely applied to the fields of medicines and food. For example, the olive leaf extract microemulsion can be applied to edible fat and oil and is used for preventing the fat and oil from rotting.
Description
Technical field
The invention belongs to biological medicine technology field, especially relate to a kind of preparation of Olive leaf P.E microemulsion and application thereof of being rich in hydroxytyrosol.
Background technology
How effectively preventing Oxidation of Fat and Oils, rotten, is a global difficult problem.Oils and fats is subject to the effect of the factors such as oxygen, water, light, heat, microorganism, understands oxidation gradually or hydrolysis and deterioration and rancidity.Its neutral fat can be decomposed into glycerol and fatty acid, or unsaturated chain in fatty acid disconnects and form peroxide, then is decomposed into successively the materials such as lower fatty acid, aldehydes, ketone, thereby produces foreign odor, abnormal flavour.Becoming sour of oils and fats is rotten, not only affects its local flavor, quality and nutritive value, also can cause the impaired of cell membrane, tissue, enzyme and gene, is detrimental to health.Have every year a lot of because having eaten the oils and fats becoming sour or the event that acute alimentary toxicosis occurs containing fatty foods by mistake in China.People eat rotten edible oil and fat, and disease very easily occurs, and accelerate aging, the more important thing is, the product that becomes sour having also has carcinogenesis.
In oils and fats, add antioxidant, for guaranteeing oils and fats and the quality containing fatty foods, extend shelf life and have very important significance.At present, the antioxidant being applied in oils and fats is mainly the antioxidant in some synthetic sources, as tert-butyl hydroquinone (TBHQ), dibenzylatiooluene (BHT), Butylated hydroxyanisole (BHA) etc.These physical properties are stable, with low cost, but have toxic and side effects, even have potential accumulation carcinogenesis.Along with socioeconomic development rapidly, what health of people was realized improves constantly, and the safety of synthetic antioxidant more and more causes people's query.Systems in Certain Developed Countries is limited the quantity already or is forbidden the synthetic antioxidant to human body toxic side effect, as Northern Europe has banned use of BHA, BHT.Research and develop the industry research focus that efficient, nontoxic natural origin antioxidant has become.
Existing research shows, multiple natural product active substances are added in oil substances has good anti-oxidation characteristics, as rosemary ethereal oil, mountain spill polyphenol etc.But most natural component material compositions itself are also subject to extraneous factor, as the impact of light, heat etc., affect its stable use.In addition, in water/oily medium, dissolubility is also undesirable, has restricted its extensive use.Therefore introduce the advanced technologies such as microemulsion (microcapsule) change active constituent is carried out to effective embedding, improve life activity, the compatibility of raising and other substrate, thus expand its range of application.
Summary of the invention
Technical problem to be solved by this invention is a kind of preparation method of Olive leaf P.E microemulsion of hydroxyl butyl alcohol, comprises following step:
Steps A: adopt heat cycles to extract.By Fructus oleae europaeae cured leaf and water, ethanol in mass ratio the ratio of 9 ︰ 1-1 ︰ 9 feed intake, temperature is controlled at 60-90 ℃, 2 hours extraction times;
Step B: adopt the method pretreatment of alcohol extracting-water precipitating.Extracting solution reclaims after solvent, water precipitating, filter pressing, merging filtrate;
Step C: adopt macroporous resin isolation and purification method purification, filtered solution is through macroporous resin adsorption, and macroporous resin adopts D101 type, Anhui Samsung resin Science and Technology Ltd. produces, average pore size 9-10 nm, is the ethanol/water mixed solvent desorption of 9 ︰ 1-1 ︰ 9 with mass ratio, collects stripping liquid;
Step D: acidolysis/be hydrolyzed above-mentioned stripping liquid, obtains the Olive leaf P.E of hydroxyl butyl alcohol.
Preferred microemulsion preparation method, comprises following step:
Hydroxytyrosol Olive leaf P.E is dissolved in water, and after the surfactant of interpolation minute quantity, homogenizing becomes suspension to obtain hydroxytyrosol emulsion, pressure 3000Psi, homogenizing time 5 minutes.Again by the PROCESS FOR TREATMENT of high shear microjet, machine models M-110S(U.S. Microfluidics International Corporation manufactures), pressure setting is 20000Psi, circulation time 5-8 minute, make nano-emulsion, and use filtering with microporous membrane degerming.Also can or be spray dried to microcapsule powder by nano-emulsion lyophilization.
Wherein, hydroxytyrosol (hydroxytyrosol, hereinafter to be referred as HT) chemistry Hydroxytyrosol by name, is a kind of natural polyphenol compounds that derives from Fructus oleae europaeae plant.Molecular formula is C
8h
10o
3, molecular weight 154.1632,15 ° of C of flash-point.The easy moisture absorption of powder.Researcher is verified both at home and abroad, and hydroxytyrosol is one antioxidation biology active substance safely and effectively.Antioxidation biology activity that olive oil series of products are good, anti-tumor activity, activity of fighting against senium etc. are mainly derived from take this compound as main serial polyphenol.
Structural formula is:
The main application of hydroxytyrosol at present has: can effectively strengthen skin elasticity and moist, effect of tool reduce wrinkle, defying age 1.; 2. contribute to the absorption of human body to mineral, keep bone density, reduce skeleton bulking; 3. the protective effect of pair human body vision, the pathological changes such as the multiple retinal degeneration that control causes because of smoking; 4. improve blood vessel elasticity, for prevention and the treatment of arteriosclerosis, hypertension etc.; 5. can promote the cancer such as pulmonary carcinoma, the breast carcinoma later stage to recover and raising chemotherapy effect; 6. also can be used as natural antibacterial, antiviral and antifungal product for agricultural and insect pest control purposes.
The source of current domestic hydroxytyrosol is mainly to extract and obtain in leaf of Fructus oleae europaeae, re-refines and forms.Fructus oleae europaeae (O1eaeuropaea L.) is the aiphyllium of Oleaceae Olea, one of world-renowned woody oil tree species.So far the cultivation history of existing more than 4000 year, is mainly distributed in 45 ° of north latitude between 37 °, south latitude, and central distribution is Mediterranean country, as Greece, Italy, Spain etc.All there is extensive introducing and planting in the whole world now.Nearly ten years, under the policy support of development of the West Regions, the plantation industry development of domestic Fructus oleae europaeae is very fast, and oneself has certain scale the construction of base of Gansu, Sichuan two provinces, and the supporting olive oil processing factory that sets up.Only, in the Di Shan river valley area, white Dragon River, upstream, Jia Lingjiang River centered by south of Gansu Province Wudu District, Gansu Province, cultivated area just reaches 180,000 hectares.Fructus oleae europaeae fruit is fully used.But every year, because the discarded leaf of Fructus oleae europaeae of pruning is more than thousands of tons of, do not obtain fine utilization.Therefore, the raw material of hydroxytyrosol obtains secure.
Preferably, described surfactant adopts at least one in lecithin, glyceryl monostearate, Solutol HS15, Tween 80, arabic gum, gelatin and modified starch.
Preferably, the aperture of described microporous filter membrane is 0.22 μ m.
The present invention also provides a kind of preparation method of the Olive leaf P.E microemulsion that is rich in hydroxytyrosol, comprise following step: HT Olive leaf P.E is dissolved in water, after the surfactant of interpolation minute quantity, homogenizing becomes suspension to obtain HT emulsion, again HT emulsion is passed through to microjet technique, make nano-emulsion, again nano-emulsion is spray dried to microcapsule powder, retains for subsequent use.
Preferably, homogenizing time is 5 minutes, and temperature is 25 ℃.
Preferably, the diameter of suspension is not less than 6 μ m.
Preferably, the diameter of nano-emulsion is 100-200nm.
Preferably, described emulsion is by microjet technique, and pressure is 20000-24000Psi.
The invention has the beneficial effects as follows: the Olive leaf P.E microemulsion of what the present invention was prepared be rich in hydroxytyrosol, all easily molten in aqueous and oily solution, applied range.Add in daily edible oil, antioxygenic property is strong, alternative existing synthetic class antioxidant.Make externally-applied liniment, can strengthen the permeability of skin.And through experiment, add in cigarette holder, can effectively reduce or offset completely vision, the lung organ etc. of the multiple harmful components such as tar in cigarettes, nicotine to human body injury.
The specific embodiment
Below preferably embodiment of the present invention is described in further detail:
embodiment 1:the deliquescent investigation in common medium of HT Fructus Canrii Albi extract
At room temperature, the dissolving situation of the HT Olive leaf P.E that investigation mass fraction is 40% in the oil products such as soybean salad oil, Oleum Arachidis hypogaeae semen, Adeps Sus domestica, the results are shown in Table 1:
Table 1 mass fraction is 40% the HT Olive leaf P.E dissolving situation in opposed polarity solvent
Illustrate: "-" represents insoluble, "+" represents solvable, and " ++ " represents easily molten.
Result shows: it is better that HT Olive leaf P.E raw material is applied in the dissolubility of commonly using in edible oil product, and the stability of appearance character can reach requirement.
embodiment 2:hT Olive leaf P.E is as the additive in grease production
The production of oils and fats general through feeding intake, aquation, come unstuck, the process such as removing impurities, dry, decolouring, filtration, deodorize, dewaxing, finally form product.
The HT Olive leaf P.E that is 20% by mass fraction before decoloration process, adds in oils and fats with 0.3 ‰ mass fraction.After the decoloration process of adsorption bleaching, wherein in decoloration process, the mass fraction proportioning of main adsorbent: Huo Bai Tu ︰ activated carbon is 12 ︰ 1, total addition is total oil mass 1%.110 ℃ of bleaching temperatures, 20 minutes time.Adopt kieselguhr drainage, oils and fats is limpid penetrating.The index such as outward appearance, abnormal smells from the patient all meets national standard, and storage life obviously extends.
The Olive leaf P.E (mass fraction is more than 20%) that HT is rich in preparation, adds in grease production technique with the amount of mass fraction 0.1 ‰, and after above-mentioned adsorption bleaching craft, the quality index such as the outward appearance of oils and fats can be up to state standards.Add the HT of antioxidant activity, can obviously extend the quality guarantee time limit of oils and fats, substituted original chemosynthesis class antioxidant.
Table 2 has added the oils and fats physical aspect of different antioxidant contents and has observed (moon)
embodiment 3:the preparation of HT microemulsion
Be to join in the pure water of 1L in 20 grams of the HT Olive leaf P.Es of 40% content mass fraction, add the surfactant arabic gum of 0.5 gram, stir.Then under the condition of pressure 3000Psi, homogenizing 5 minutes.Pass through again the PROCESS FOR TREATMENT of high shear microjet, machine models M-110S, pressure setting is 20000Psi, preparing diameter is the nano sized particles HT microemulsion that is less than 200nm.
?
embodiment 4:hT Olive leaf P.E microemulsion powder directly adds in finished product oils and fats
The HT microemulsion of above-mentioned example 3 is spray-dried, 185 ℃ of air outlet temperature, and flow velocity 80ml/h, obtains superfine dry powder, and the mass fraction with 0.05 ‰ is than directly adding in edible oil.Fluid is limpid thorough, occurs without muddiness and float.The storage life of product oil obviously extends.
embodiment 5:hT Olive leaf P.E microemulsion powder directly adds in daily use chemicals substrate
The HT Olive leaf P.E that is 40% by the mass fraction of 10g is dissolved in the water of 1 L, adds the Tween 80 of 0.25g.Mixture homogenizing 5 minutes at 25 ℃, homogenizing becomes suspension, and (diameter is greater than 6 μ m).HT emulsion is by microjet technique, and pressure is 24000Psi.Circulation time 5 minutes, makes nano-emulsion (diameter 100-200nm).Nano-emulsion lyophilization is become to microcapsule powder, retain for subsequent use.Or be deployed into required ratio with hypoallergenic butterfat and add in substrate used.
embodiment 6:the mensuration of HT Olive leaf P.E microemulsion powder antioxygenic property in common oils and fats
Adopt Schaal Oven Method: get 50g oil sample, put into 100ml beaker, uncovered, add HT powder microcapsule and the reference substance Herba Rosmarini Officinalis oil product antioxidant of the embodiment 4 of variable concentrations in ratio as shown in table 3, mix homogeneously, puts into 60 ℃ of constant temperature oven strengthenings by oil sample and preserves.Stir once every 24h, and exchange their positions in baking oven.Pressing GB/T 5009.37-2003 " analytical method of edible vegetable oil sanitary standard " measures oil peroxidation value (peroxide value, POV).Evaluate the antioxidant activity of HT microcapsule by protection factor (protection factor, PF).By edible oil sanitary standard regulation, when in oils and fats, POV value reaches 11.8mmol/kg, the required time is induction time, i.e. active oxygen method (active oxygen method, AOM) value.The AOM value that the AOM ÷ of calculating protection factor PF(PF=interpolation HT does not add HT).
The antioxidation of table 3 Different adding amount HT to Adeps Sus domestica
embodiment 7:hT microemulsion mouse skin is put test outward on the skin
The HT microemulsion that example 5 has been added to butterfat is test specimen, carries out the test of laboratory animal cutaneous permeability.Adopt 6 of the large ear rabbits of healthy Japan.Be divided at random 3 groups, be respectively blank group, HT extract group (having added same butterfat allotment), HT extract microemulsion group.By the test exposed identical region of rabbit back, equal area (4 × 4cm).Being coated with respectively and putting said medicine 1g(mass concentration on the skin is 40%HT Fructus Canrii Albi extract), twice of every day.For three days on end.Half an hour after administration for the second time, ear vein is got blood 2ml, according to a conventional method separation of serum.Adopt the method for HPLC to measure the content of HT in serum.Result is as shown in table 4:
The comparison of table 4 HT Olive leaf P.E group and HT Olive leaf P.E group microemulsion group cutaneous permeability
embodiment 8:add the application of cigarette holder to
Acrylic aldehyde is harmful components main in smoke from cigarette.Acrylic aldehyde directly cause the mitochondrial oxidative damage of retinal pigment epithelium and function weak, and reduce the ability of cytothesis damage, be the principal element that smog of smoking harms one's eyes.Acrylic aldehyde can also cause the multiple tissues of health as the gene mutation of pulmonary/tracheal cell, and finally causes the generation of cancer.
HT is a kind of natural nutrient of generally acknowledged resist mitochondria damage.The HT Olive leaf P.E nanometer microemulsion of example 3 is made into aqueous solution by 10% mass concentration.Be impregnated into cigarette filter.Cigarette holder after wet dipping microcapsule is placed in to ultra cold storage freezer, then it is dry to be placed in vacuum freeze drier.The densification of microcapsule wall film and the good HT microcapsule of release performance that form.
When cigarette combustion, HT microcapsule is heated, and synchronously discharges HT smog, absorbs from the exposure such as oral cavity, eye of human body, can effectively reduce or offset vision, the lung organ etc. of the multiple harmful components such as tar in cigarettes, nicotine to human body injury.
We study by vitro tests, and having investigated HT is the function of (eyes) injury protection for people ARPE-19 cultured cell for acrylic aldehyde.
1) preparation of sample:
Acrylic aldehyde and mass fraction are that 20% HT Olive leaf P.E is dissolved in respectively in PBS, and HT is made into storing solution, are kept in 4 ℃ of refrigerators, and acrylic aldehyde is prepared before each experiment is used.
2) cell culture and grouping:
Mankind ARPE-19 cell line, divides by 0.05 × 10
6, 0.1 × 10
6, 0.5 × 10
6cell density plant in 100mm
2in culture dish, in 96 holes and 6 porocyte culture fluid (DMEM-F12, purchased from Sigma company).Put 37 ℃, 5%CO
2in incubator.In cultivation process, within every 3-4 days, change culture fluid once, under inverted microscope, observe, select upgrowth situation well and stick culture bottle or the cell of 80% left and right, culture plate bottom, apply following processing factor.Experimental group: the acrylic aldehyde of variable concentrations (0,5,10,25,50,100 μ mol/L) is added respectively in ARPE-19 cell culture fluid and cultivated 24 hours.Intervention group: by the HT Olive leaf P.E of variable concentrations (in HT sterling, 0,10,20,50,100,200 μ mol/L) join in advance in ARPE-19 cell culture fluid and cultivate 48 hours, then change into containing the culture fluid of acrylic aldehyde (50 μ mol/L) and cultivate 24 hours.More than test each concentration group and all establish 3 Duplicate Samples, each test repeats 3 times.
3) assay method:
1. cell survival rate is measured: the 96 every holes of well culture plate add 20 μ l(5mg/ml) MTT(tetrazolium) solution, cultivate after 3 hours, discard culture fluid, add the DMSO of 100 μ l, place 10min at 37 ℃, mix and under 555nm, measure OD value.
2. cell line granulosa potential measurement: the 96 every holes of well culture plate add 100 μ UC-1(MolecularProbes companies to provide, concentration is 2 μ g/ml) continuation cultivation 30min, then rinse secondary with the cell culture fluid of dilution, every hole adds 100 μ l cell culture fluids again, under 485 nm exciting lights and 535nm, 590nm utilizing emitted light, measure red, green fluorescence intensity respectively with porous fluorescence calculating instrument, represent mitochondrial membrane potential in anoxic with red/green fluorescence ratio.
4) result and discussion:
The impact of the acrylic aldehyde of table 5 variable concentrations on people ARPE-19 cultured cell survival rate
The impact of the acrylic aldehyde of table 6 variable concentrations on people ARPE-19 cultured cell mitochondrial membrane potential
Presentation of results: the acrylic aldehyde of variable concentrations is respectively with ARPE-19 cytosis after 24 hours, show by said determination result: with matched group comparison, 50 μ M and 100 μ M acrylic aldehyde have produced cytotoxicity, make cell survival rate drop to respectively 54.3%, 22.2%.Make mitochondrial membrane potential ratio drop to respectively 3.80,2.76.
The HT of table 7 variable concentrations reduces the protective effect of people ARPE-19 cultured cell survival rate for acrylic aldehyde
Note: with the 5th comparison of table 5, p<0.05, * * p<0.01;
The HT of table 8 variable concentrations reduces the protective effect of people ARPE-19 cultured cell mitochondrial membrane potential for acrylic aldehyde
Note: with the 5th comparison of table 6, * * p<0.01;
Presentation of results: containing the culture fluid of variable concentrations HT Olive leaf P.E in advance with ARPE-19 cytosis after 48 hours, then with common the cultivation 24 hours of culture fluid containing 50 μ M acrylic aldehyde.Our experimental study shows: cell survival rate and mitochondrial membrane potential that the HT of 0-50 μ M reduces for ARPE-19 cell do not have a significant effect.But the survival rate of the cell ARPE-19 cell that the HT of 100-200 μ M reduces for 50 μ M acrylic aldehyde and mitochondrial membrane potential decline and are significantly improved effect (p<0.05-0.01), and prompting has protective effect.
Discussion of results: it is generally acknowledged, acrylic aldehyde causes the death of people ARPE-19 cell mainly by cell mitochondrial is damaged and carried out.The confirmation of this development test result, HT Olive leaf P.E can have good protective effect to this type of damage, and the antioxygenic property that dominant mechanism may be good with it is relevant.Prompting HT Olive leaf P.E is for toxic component main in people's smog of smoking---and vision impairment, cytometaplasia that acrylic aldehyde causes have protective effect.
Above content is in conjunction with concrete preferred implementation further description made for the present invention, can not assert that specific embodiment of the invention is confined to these explanations.For general technical staff of the technical field of the invention, without departing from the inventive concept of the premise, can also make some simple deduction or replace, all should be considered as belonging to protection scope of the present invention.
Claims (1)
1. a preparation method for the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol, is characterized in that, comprises following step:
Steps A: extract after Fructus oleae europaeae cured leaf and polar solvent are fed intake;
Step B: adopt the method pretreatment of alcohol extracting-water precipitating, extracting solution reclaims after solvent, water precipitating, filter pressing, merging filtrate;
Step C: adopt macroporous resin isolation and purification method purification, filtered solution, through macroporous resin adsorption, by ethanol, the water mixed solvent desorption of 9:1-1:9 ratio in mass ratio, is collected stripping liquid;
Step D: the stripping liquid in acidolysis/hydrolysing step C, obtains the Olive leaf P.E of hydroxyl butyl alcohol;
Step e: hydroxytyrosol Olive leaf P.E is dissolved in water, and after interpolation surfactant, homogenizing becomes suspension to obtain hydroxytyrosol emulsion;
Step F: again hydroxytyrosol emulsion is passed through to microjet technique, make nano-emulsion;
Step G: adopt filtering with microporous membrane degerming;
Described surfactant adopts at least one in lecithin, glyceryl monostearate, Solutol HS15 and Tween 80;
Described emulsion is by microjet technique, and pressure is 20000-24000Psi.
2. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, homogenizing time is 5 minutes, and temperature is 25 ℃.
3. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, the diameter of suspension is not less than 6 μ m.
4. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, the diameter of nano-emulsion is 100-200nm.
5. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, the aperture of described microporous filter membrane is 0.22 μ m.
6. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, the temperature in described steps A is 60-90 ℃.
7. the preparation method of the Olive leaf P.E nano-emulsion of hydroxyl butyl alcohol as claimed in claim 1, is characterized in that, the mass ratio of described Fructus oleae europaeae cured leaf and polar solvent is 9:1-1:9.
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| CN110022698A (en) * | 2016-11-30 | 2019-07-16 | 日本烟草产业株式会社 | Smoking article piece containing fragrance and smoking article comprising the piece containing fragrance |
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| KR20160050826A (en) * | 2014-10-31 | 2016-05-11 | 씨제이제일제당 (주) | Emulsified oil comprising antioxidants, cooking oil comprising the emulsified oil and manufacturing methods of thereof |
| CN105997703B (en) * | 2016-07-05 | 2019-11-12 | 上海相宜本草化妆品股份有限公司 | Olive leaf P.E and cosmetics comprising the extract |
| CN108157942B (en) * | 2017-11-17 | 2021-07-30 | 中国林业科学研究院林产化学工业研究所 | Method for embedding hydroxytyrosol by spraying gelatinized ginkgo starch |
| CN108403494B (en) * | 2018-03-30 | 2021-05-28 | 四川四季莱源贸易有限公司 | Fat-soluble olive leaf essence anti-aging skin care product and preparation method thereof |
| CN108888595A (en) * | 2018-09-12 | 2018-11-27 | 山东省药学科学院 | A kind of nano-emulsion preparation containing hydroxytyrosol and its freeze-dried preparation method |
| CN114931519A (en) * | 2022-06-29 | 2022-08-23 | 上海贤鼎生物科技有限公司 | Synthesis method of hydroxytyrosol and derivatives thereof and application of hydroxytyrosol and derivatives thereof in cosmetics |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276424A (en) * | 2011-06-15 | 2011-12-14 | 陕西禾博天然产物有限公司 | Method for preparing hydroxytyrosol by boiling and hydrolyzing |
| CN102731592A (en) * | 2012-06-25 | 2012-10-17 | 向华 | Method for extracting cleupin and amentoflavone from olive leaf |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102276424A (en) * | 2011-06-15 | 2011-12-14 | 陕西禾博天然产物有限公司 | Method for preparing hydroxytyrosol by boiling and hydrolyzing |
| CN102731592A (en) * | 2012-06-25 | 2012-10-17 | 向华 | Method for extracting cleupin and amentoflavone from olive leaf |
Cited By (1)
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|---|---|---|---|---|
| CN110022698A (en) * | 2016-11-30 | 2019-07-16 | 日本烟草产业株式会社 | Smoking article piece containing fragrance and smoking article comprising the piece containing fragrance |
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