CN106860498B - Method for simultaneously extracting polyphenol and flavone - Google Patents
Method for simultaneously extracting polyphenol and flavone Download PDFInfo
- Publication number
- CN106860498B CN106860498B CN201710041502.2A CN201710041502A CN106860498B CN 106860498 B CN106860498 B CN 106860498B CN 201710041502 A CN201710041502 A CN 201710041502A CN 106860498 B CN106860498 B CN 106860498B
- Authority
- CN
- China
- Prior art keywords
- flavone
- polyphenol
- simultaneously extracting
- filtrate
- flavonoids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 21
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 21
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title claims abstract description 16
- 229930003944 flavone Natural products 0.000 title claims abstract description 16
- 150000002212 flavone derivatives Chemical class 0.000 title claims abstract description 16
- 235000011949 flavones Nutrition 0.000 title claims abstract description 16
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 240000007817 Olea europaea Species 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 5
- 229930003935 flavonoid Natural products 0.000 claims description 5
- 150000002215 flavonoids Chemical class 0.000 claims description 5
- 235000017173 flavonoids Nutrition 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000009777 vacuum freeze-drying Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000007873 sieving Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 6
- 238000012545 processing Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- 238000002835 absorbance Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 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 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 1
- 241000207836 Olea <angiosperm> Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229940010514 ammonium ferrous sulfate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/32—Burseraceae (Frankincense family)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
Abstract
The invention belongs to the field of deep processing of agricultural products, and particularly relates to a method for simultaneously extracting polyphenol and flavone, which comprises the following steps: after the olive stones are shelled, the red skins and the nuts are separated, the separated red skins are dried, crushed and sieved, and are added into a mixed solution of ethanol and water, the mixed solution is heated, extracted and filtered, filtrate is collected, concentrated and dried to obtain flavone and polyphenol, and the extraction method has the advantages of high yield and purity, simple operation, convenience, rapidness, low cost and contribution to industrial production.
Description
Technical Field
The invention belongs to the field of deep processing of agricultural products, and particularly relates to a method for simultaneously extracting polyphenol and flavone.
Background
The polyphenol and flavonoid substances have strong physiological activities of resisting tumors, oxidation, bacteria and cancers, removing free radicals, preventing cardiovascular and cerebrovascular diseases and the like, and are natural antioxidants worthy of development.
The olive has more than 2000 years of planting history in China, and is mainly distributed in the provinces of Longnan, Fujian, Guangdong, Guangxi, Hainan and the like at present. A great deal of research shows that the olive contains a plurality of substances beneficial to human bodies, and the olive has great value to human health from the pulp to the kernel. The utilization of olives is mainly used for squeezing olive oil at present, but the deep development and utilization of the olive pit and the olive kernel are almost blank, such as the olive kernel red skin in the olive pit. Therefore, an economical and feasible processing technology of the olive red skin is developed and utilized in the olive industry chain, the added value of the product is improved, and the method has important economic and social significance for increasing the economic income of farmers.
Disclosure of Invention
The invention provides a method for simultaneously extracting polyphenol and flavone, which comprises the following steps:
(1) after the olive stones are shelled, the red skin is separated from the kernels, the separated red skin is dried, crushed and sieved,
wherein, after being crushed, the mixture is sieved by a 60-mesh sieve;
(2) adding the sieved red skins obtained in the step (1) into a mixed solution of ethanol and water, heating, extracting, filtering, collecting filtrate,
wherein, in the mixed solution of ethanol and water, the volume ratio of ethanol to water is 3: 1,
adding cortex Oroxyli into the mixed solution, extracting at 50 deg.C in a constant temperature water bath oscillator under stirring for 30 min;
(3) concentrating and drying the filtrate obtained in the step (2) to obtain flavone and polyphenol,
wherein the filtrate is desolventized and concentrated for 30min on a rotary evaporator, and the concentrated solution is subjected to vacuum freeze drying.
The invention has the beneficial effects that: the yield of polyphenol and flavone of the olive kernel red skin is high, and the purity is high; the extraction method has simple operation, convenience and rapidness, low cost and contribution to industrial production.
Drawings
FIG. 1 shows the specific results of the clearance test in example 1 of the present invention.
FIG. 2 is an absorption spectrum of olive kernel red skin extract in example 1 of the present invention.
Detailed Description
Example 1
(1) After the olive stones are shelled, separating the red skin from the kernels, naturally drying the separated red skin at room temperature (25 ℃), crushing, and sieving by a 60-mesh sieve;
(2) taking 50g of sieved red skin obtained in the step (1), placing the red skin in a beaker, and adding ethanol and water in a volume ratio of 3: 1, placing the beaker in a 50 ℃ constant temperature water bath oscillator, stirring and extracting the red skin for 30min, centrifugally filtering, collecting filtrate,
the detection means is as follows:
diluting the collected filtrate to a constant volume of 1000mL, putting 1mL of sample liquid into a clean 10mL volumetric flask, adding 4mL of ethanol aqueous solution with the mass fraction of 30%, then adding 4mL of aluminum chloride aqueous solution with the mass fraction of 1%, finally using 30% ethanol aqueous solution to a constant volume of 10mL, tightly covering, and shaking up by reversing. At the wavelength of 415nm, a blank reagent is used as a control, the absorbance is measured, and the following can be obtained through calculation: the yield of flavone is 1.5% (mass percentage of the obtained flavone relative to the raw material red skin);
or diluting the collected filtrate to 1000mL, taking 1mL sample solution, adding 5mL distilled water and 1mL forskolin phenol reagent (national drug group chemical reagent Co., Ltd.) into a clean 10mL volumetric flask, finally diluting with 7.5% sodium carbonate solution to 10mL, covering tightly, and shaking up by reversing. At the wavelength 765nm, a blank reagent is used as a control, the absorbance is measured, and the following can be obtained through calculation: the yield of polyphenol is 3% (mass percentage of the obtained polyphenol relative to the raw material red skin);
(3) and (3) desolventizing and concentrating the filtrate collected in the step (2) on a rotary evaporator for 30min, and then carrying out vacuum freeze drying on the concentrated solution to obtain polyphenol and flavone, wherein the total content of the polyphenol and the flavone in the dried product reaches 40% (the mass ratio of the flavone to the polyphenol to the dried product).
Taking 7 cuvettes (numbered 1, 2, 3, 4, 5, 6 and 7) with 10mL, respectively adding 0.3mL of 7.5mmol/L ammonium ferrous sulfate solution, 0.3mL of 7.5mmol/L phenanthroline solution and 1mL of Tris-HCl buffer solution with pH of 7.4, respectively adding 0.2mL of 7.5mmol/L H into the cuvettes No. 2, 3, 4, 5, 6 and 72O2Adding 0.3mL of dispersion prepared from the dried mixture obtained in the step (3) into colorimetric tubes No. 3, 4, 5, 6 and 7 respectively to obtain a solution with the concentration of 1.0 mu g/mL, 5.0 mu g/mL, 10.0 mu g/mL, 20.0 mu g/mL and 40.0 mu g/mL in sequence, adding redistilled water to the volume of 10mL, reacting in a water bath at 37 ℃ for 1h, and reacting in a water bath at 52 DEG CThe absorbance was measured at a wavelength of 0nm, and the hydroxyl radical (. OH) clearance was calculated according to the following formula:
clearance ═ 100% [ (OD sample-OD loss)/(OD blank-OD loss) ]
(wherein "OD sample" is the absorbance detected by cuvettes 3, 4, 5, 6, 7 to which the extract was added; and "OD blank" is the absorbance detected by cuvettes to which no H was added2O2Absorbance detected by a colorimetric cylinder 1 of an aqueous solution; "OD loss" is the addition of H2O2Absorbance detected by cuvette 2 for aqueous solutions. )
The specific clearance calculation result is shown in the attached figure 1, wherein the abscissa represents the specific concentration of 0.3ml of the dispersion prepared from the dried substance obtained in the step (3) added to the relevant colorimetric tube; the ordinate represents the percentage of clearance. Therefore, the olive kernel red skin extract has good antioxidant activity.
Determination of the spectral properties of the product:
weighing 0.01g of the dried olive kernel red skin extract obtained in the step (3), preparing 0.10g/L solution by using 70% by volume of ethanol water solution, and scanning the solution within the range of 200-800 nm on an ultraviolet visible spectrophotometer by using the same solvent (70% by volume of ethanol water solution) as reference to obtain an absorption spectrogram of the olive kernel red skin extract.
As can be seen from the attached figure 2, two obvious absorption peaks are present near the wavelength of 300nm and 360nm in the ultraviolet region, which are typical absorption peaks of polyphenol and flavone.
Claims (5)
1. A method for simultaneously extracting polyphenol and flavone is characterized in that: the method comprises the following steps of,
(1) after the olive stones are shelled, separating the red skin from the kernels, drying, crushing and sieving the separated red skin;
(2) adding the sieved red skins obtained in the step (1) into a mixed solution of ethanol and water, heating, extracting, filtering and collecting filtrate;
wherein the volume ratio of ethanol to water is 3: 1;
the extraction is that the crushed red skin is added into the mixed solution and then extracted in a constant temperature water bath oscillator at 50 ℃;
(3) and (3) concentrating and drying the filtrate obtained in the step (2) to obtain flavone and polyphenol.
2. The method for simultaneously extracting polyphenols and flavonoids as claimed in claim 1, wherein: in the step (1), the mixture is crushed and then sieved by a 60-mesh sieve.
3. The method for simultaneously extracting polyphenols and flavonoids as claimed in claim 1, wherein: in the step (2), the extraction is carried out under a stirring state, and the extraction time is 30 min.
4. The method for simultaneously extracting polyphenols and flavonoids as claimed in claim 1, wherein: and (3) carrying out desolventizing concentration on the filtrate on a rotary evaporator for 30 min.
5. The method for simultaneously extracting polyphenols and flavonoids as claimed in claim 1, wherein: and (3) concentrating the filtrate, and then carrying out vacuum freeze drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710041502.2A CN106860498B (en) | 2017-01-20 | 2017-01-20 | Method for simultaneously extracting polyphenol and flavone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710041502.2A CN106860498B (en) | 2017-01-20 | 2017-01-20 | Method for simultaneously extracting polyphenol and flavone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106860498A CN106860498A (en) | 2017-06-20 |
| CN106860498B true CN106860498B (en) | 2020-04-28 |
Family
ID=59158469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710041502.2A Active CN106860498B (en) | 2017-01-20 | 2017-01-20 | Method for simultaneously extracting polyphenol and flavone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106860498B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108752393B (en) * | 2018-05-22 | 2021-04-16 | 湖北中烟工业有限责任公司 | A kind of extraction method of natural polyphenols and flavonoids for cigarettes |
-
2017
- 2017-01-20 CN CN201710041502.2A patent/CN106860498B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| 杏仁种皮中多酚类物质的提取研究;郭文娟;《食品工程》;20110930(第3期);第43-46页 * |
| 核桃仁种皮中的多酚类物质高压液相色谱分析;万政敏等;《食品工业科技》;20071231;第28卷(第7期);第212-213和224页 * |
| 红松子种皮提取物活性成分及抗氧化作用研究;苏晓雨等;《林产化学与工业》;20100831;第30卷(第4期);第99-102页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106860498A (en) | 2017-06-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lou et al. | Nondestructive evaluation of the changes of total flavonoid, total phenols, ABTS and DPPH radical scavenging activities, and sugars during mulberry (Morus alba L.) fruits development by chlorophyll fluorescence and RGB intensity values | |
| Jokić et al. | Modelling of the process of solid-liquid extraction of total polyphenols from soybeans | |
| Chen et al. | Ultrasound-assisted extraction of polysaccharides from litchi (Litchi chinensis Sonn.) seed by response surface methodology and their structural characteristics | |
| Kanmaz | Subcritical water extraction of phenolic compounds from flaxseed meal sticks using accelerated solvent extractor (ASE) | |
| Silva et al. | Ultrasound‐assisted extraction of red beet pigments (Beta vulgaris L.): Influence of operational parameters and kinetic modeling | |
| Miskinis et al. | Bioactive compounds from acerola pomace: A review | |
| Neo et al. | Determination of oil palm fruit phenolic compounds and their antioxidant activities using spectrophotometric methods | |
| Gao et al. | Optimization of anthocyanidins conversion using chokeberry pomace rich in polymeric proanthocyanidins and cellular antioxidant activity analysis | |
| Parada et al. | Sequential extraction of Hericium erinaceus using green solvents | |
| Quyen et al. | Antioxidant activity, total phenolics and flavonoids contents of Pandanus amaryllifolius (Roxb.) | |
| Chua et al. | Water soluble phenolics, flavonoids and anthocyanins extracted from jaboticaba berries using maceration with ultrasonic pretreatment | |
| Secco et al. | Valorization of blueberry by-products (Vaccinium spp.): Antioxidants by pressurized liquid extraction (ple) and kinetics models | |
| CN106860498B (en) | Method for simultaneously extracting polyphenol and flavone | |
| Pourali et al. | Extraction of phenolic compounds and quantification of the total phenol of grape pomace | |
| Jokić et al. | Influence of extraction type on the total phenolics, total flavonoids and total colour change of different varieties of fig extracts | |
| CN109744540A (en) | The extracting method of melanoidin in a kind of black garlic | |
| CN109043117A (en) | A kind of acidity Queensland nut glycoprotein and its production method | |
| CN109211805B (en) | Verification analysis method for traceability of mussel carotenoid extract | |
| Gautam et al. | Preliminary studies on the bioactive phytochemicals in extract of Cape Gooseberry (Physalis peruviana L.) fruits and their products | |
| CN113512020B (en) | Method for extracting catechin and epicatechin from pericarp of plant of Camellia | |
| Tai et al. | Ethanol-modified supercritical CO 2 extraction of cashew (Anacardium occidentale) nut testa. | |
| Aflaki | Optimization of carotenoid extraction in peel and flesh of cantaloupe (Cucumis melo L.) with ethanol solvent | |
| CN110204924B (en) | Method for preparing black fungus melanin by irradiation-enzymolysis auxiliary non-thermal high-pressure method | |
| EP3400812A1 (en) | Obtainment process of carotenoids concentrate rich in lycopene from red fruits and/or red fruit pulp | |
| JP5864042B2 (en) | Process for producing a food material comprising an extract containing β-cryptoxanthin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |