CN110041190A - The method of phenolic acid compound is extracted in a kind of Oil-tea-cake - Google Patents
The method of phenolic acid compound is extracted in a kind of Oil-tea-cake Download PDFInfo
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- CN110041190A CN110041190A CN201910278398.8A CN201910278398A CN110041190A CN 110041190 A CN110041190 A CN 110041190A CN 201910278398 A CN201910278398 A CN 201910278398A CN 110041190 A CN110041190 A CN 110041190A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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Abstract
The invention discloses a kind of methods that phenolic acid compound is extracted in Oil-tea-cake, comprising the following steps: the Oil-tea-cake after extracting degreasing, 70%EtOH refluxing extraction after crushing, combined extract are concentrated under reduced pressure, obtain Oil-tea-cake medicinal extract；Medicinal extract adds water to be suspended, and is placed in separatory funnel, is first extracted with ethyl acetate, then with extracting n-butyl alcohol, after recycling design, respectively obtains acetic acid ethyl ester extract, ethyl acetate extract medicinal extract and n-butyl alcohol extract；Ethyl acetate extract medicinal extract is taken, 5 flow points E1, E2, E3, E4, E5 are obtained using EtOAc-CH3OH system gradient elution by silica gel column chromatography；E1 is through the methods of silica gel column chromatography repeatedly, Sephadex LH-20 gel column chromatography, HPLC isolated phenolic acid compound 2 and compound 3；E3 respectively obtains phenolic acid compound 1 through silica gel column chromatography repeatedly.Compound of phenolic acid structure that extracting method provided by the invention obtains, efficacy stability, content and high income.
Description
Technical field
The present invention relates to extracted form natural plant technical field, in particular to phenolic acid compound is extracted in a kind of Oil-tea-cake
Method.
Background technique
Oil tea (Camellia oleifera It Abel.) is Theaceae (Theaceae) oil tea category (Camellia Linn)
Evergreen dungarunga is mainly distributed on China, Japan, south east asia, throughout 18, China provinces and regions, wherein Hunan, Jiangxi, wide
The provinces such as west, Zhejiang are major production areas.Because its seed can squeeze tea oil, therefore oil tea of gaining the name.Tea oil is the big xylophyta oil in the world four
One, the content of unsaturated fatty acid is much higher than soya-bean oil, rape oil and peanut oil in tea oil, and content is up to 90% or more, vitamin E
Content is also higher by one times than olive oil, and long-term consumption can reduce serum cholesterol, plays the role of preventing and treating cardiovascular disease.
Due to the plurality of health care functions of tea oil, the cultivated area of oil tea is risen year by year, but resulting residue (oil after Seed of Camellia oleifera oil expression
Tea cake) main agricultural by-products are used as, it such as cannot get appropriate processing, the waste of the pollution and resource of environment will be caused.For
Realize the recycling of agricultural by-products, realize it is environmental-friendly, Many researchers to the chemical component of Oil-tea-cake and pharmacological activity into
It has gone research, it is found that the chemical component of Oil-tea-cake includes saponin(e, flavones, alkaloid, phenolic acid and tannin etc., wherein phenolic acid class and Huang
Ketone compounds largely exist extensively in the platymiscium, are the main components of Oil-tea-cake, it is anti-that pharmaceutical research shows that it has
The pharmacological activity such as cancer, antibacterial, anti-inflammatory, anti-oxidant, anti-mutation and neuroprotection.
It is a variety of research shows that phenolic acid compound anti-oxidant, antibacterial anti-inflammatory, in terms of there is very strong pharmacology to make
With, be natural antibacterial agent, find have antibacterial activity phenolic acid compound be of great significance.
Summary of the invention
Present invention solves the technical problem that how being studied from utilization of resources angle, cheap oil tea is utilized
Cake, extracts the method capable of being industrialized of separation phenolic acid compound, and compound of phenolic acid structure, the drug effect which obtains are steady
It is fixed, content and high income.
In order to solve the technical problem, technical solution provided by the invention is as follows:
The method of phenolic acid compound is extracted in a kind of Oil-tea-cake, comprising the following steps:
(1) Oil-tea-cake after extracting degreasing, 70% EtOH refluxing extraction after crushing, combined extract are concentrated under reduced pressure, obtain Oil-tea-cake
Medicinal extract；
(2) medicinal extract adds water to be suspended, and is placed in separatory funnel, is first extracted with ethyl acetate, then with extracting n-butyl alcohol, recycling design
Afterwards, acetic acid ethyl ester extract, ethyl acetate extract medicinal extract and n-butyl alcohol extract are respectively obtained；
(3) ethyl acetate extract medicinal extract is taken, by silica gel column chromatography, using EtOAc-CH3OH system gradient elution, obtains 5
A flow point E1, E2, E3, E4, E5；E1 is through the methods of silica gel column chromatography repeatedly, Sephadex LH-20 gel column chromatography, HPLC point
From obtaining phenolic acid compound 2 and compound 3,
Phenolic acid compound 2,
Phenolic acid compound 3；
E3 respectively obtains phenolic acid compound 1 through silica gel column chromatography repeatedly,
Phenolic acid compound 1.
Preferably, Oil-tea-cake and 70% EtOH mass volume ratio are 1:10g/ml, 70% EtOH reflux in the step (1)
Extraction time is 3 times, and each extraction time is 3 hours.
Preferably, ethyl acetate, the volume of n-butanol are identical as aqueous suspension in the step (2).
Preferably, EtOAc-CH in the step (3)3OH system gradient elution concentration is than being respectively 30:1,20:1,10:
1、5:1、1:1。
Preferably, the isolated phenolic acid compound of the step (3) is suitable for preparation and inhibits melanin production drug
And product.
Compared with the existing technology, the invention has the benefit that
The present invention after being extracted oil for the first time using Seed of Camellia oleifera obtained residue successively mentioned using n-hexane degreasing, 70% ethyl alcohol as raw material
It takes, ethyl acetate extraction, the several steps of extracting n-butyl alcohol, then passes sequentially through silica gel column chromatography, macroporous adsorbent resin column chromatography, silicagel column
Chromatography, reversed-phase column chromatography, gel column chromatography and high performance liquid chromatography separation, easy, quick extract isolate flavonoid
Object, no hazardous solvent, extraction effect is good, is suitble to industrialized production.Gained compound, which has, simultaneously inhibits melanin production activity,
The application that can be used for instructing Oil-tea-cake realizes the recycling of agricultural by product and the protection of environment.
Detailed description of the invention
Attached drawing 1: phenolic acid compound 1 in the embodiment of the present invention1H-NMR spectrogram (300MHz, DMSO-d 6)；
Attached drawing 2: phenolic acid compound 1 in the embodiment of the present invention13C-NMR spectrogram (150MHz, DMSO-d 6)；
Attached drawing 3: phenolic acid compound 2 in the embodiment of the present invention1H-NMR spectrum (300MHz, DMSO-d 6)；
Attached drawing 4: phenolic acid compound 2 in the embodiment of the present invention13C-NMR spectrogram (75MHz, DMSO-d 6)；
Attached drawing 5: phenolic acid compound 3 in the embodiment of the present invention1H-NMR spectrum (300MHz, DMSO-d 6)；
Attached drawing 6: phenolic acid compound 3 in the embodiment of the present invention13C-NMR spectrogram (75MHz, DMSO-d 6)。
Specific embodiment
Embodiment listed below facilitates those skilled in the art and more fully understands technical solution of the present invention, but not to appoint
Where formula limitation is of the invention.
1 phenolic acid compound of embodiment isolates and purifies
(1) 25.0 Kg of Oil-tea-cake after extracting degreasing, 70% EtOH refluxing extraction 3 times after crushing, wherein Oil-tea-cake and 70%
EtOH mass volume ratio is 1:10g/m, is extracted 3 hours every time, combined extract, is concentrated under reduced pressure, and the leaching of 6.6Kg Oil-tea-cake is obtained
Cream；
(2) medicinal extract adds water to be suspended, and is placed in separatory funnel, is extracted 3 times with the isometric ethyl acetate of aqueous suspension, then with
Aqueous suspension isometric extracting n-butyl alcohol 3 times after recycling design, respectively obtain the leaching of acetic acid ethyl ester extract ethyl acetate extract
Cream 35.0g, 858.0 g of n-butyl alcohol extract；
(3) ethyl acetate extract medicinal extract (35.0g), by silica gel column chromatography, using EtOAc-CH3OH system (30:1,
20:1,10:1,5:1,1:1) gradient elution, obtain 5 flow points [E1 (3.1 g), E2 (13.1 g), E3 (6.8 g),
E4 (5.5 g) ,E5 (5.0 g)].E1 (3.1 g) is through silica gel column chromatography repeatedly, Sephadex LH-20 gel column color
Spectrum, isolated 2 compounds of the methods of HPLC, respectively compound 2 (4.0 mg), 3 (2.2 mg).E3 (6.8 g) warp
The isolated compound 1 (10.2 mg) of silica gel column chromatogram method repeatedly.
Test example 1
(1) Structural Identification of phenolic acid compound 1
The structure of the compound 1 of the separated purifying of the embodiment of the present invention 1 is identified:
Embodiment 1 separates the compound of phenolic acid 1 acquired, and English name is protocatechuate acid.
Chemical formula are as follows: C7H6O4。
The correlation analysis of phenolic acid compound 1 is as follows:
Phenolic acid compound 1 is white needles, has blackening under ultraviolet 254 nm irradiation；Ferric chloride reaction is the positive, is indicated
Phenolic hydroxyl group exists；The green reaction of bromine potassium phenol is the positive, indicates that there are carboxyls；Displaing amaranth after the heating of the vanillic aldehyde concentrated sulfuric acid, prompting should
Compound may be phenol compound.ESI-MSm/z153.0 [M-H]-, thus it is speculated that its molecular weight is 154.
According to1H-NMR (300 MHz, CD3OD-d 4) modal data shows,δ H 7.46 (1H, dd, J = 1.8 Hz,
7.2 Hz, H-6), 7.43 (1H, dd, J = 1.8 Hz, H-2), 6.82 (1H, d, J =8.7 Hz, H-5) it mentions
Show that there are one 1,3,4 substituted phenyl ring in compound structure.13C-NMR (75 MHz, CD3OD-d 4) in spectrum,δ C
170.2 be the carboxyl carbon signal on phenyl ring,δ C 123.1 (C-1), 117.7 (C-2), 146.0 (C-3), 151.6 (C-
4), 115.8 (C-5), 123.9 (C-6) are carbon signal on phenyl ring.
Above data with document report (bibliography: grind by the oil tea root chemical component such as [4] Tong little Jing, Chen Chong, Li Xia
Study carefully [J] Chinese herbal medicine, 2011,42 (10): comparing 1936-1938) is almost the same, therefore determines that the compound is
Protocatechuate acid, and determine that the chemical structural formula of the compound is determined as phenolic acid compound 1:
Phenolic acid compound 1
(2) Structural Identification of phenolic acid compound 2
The structure for purifying obtained phenolic acid compound 2 separated to the embodiment of the present invention 1 is identified:
Embodiment 1 separates the compound of phenolic acid 2 acquired, and English name is 3-hydroxybenzoic acid.
Chemical formula are as follows: C7H6O3。
The correlation analysis of phenolic acid compound 2 is as follows:
Phenolic acid compound 2 is white needles, has blackening under ultraviolet 254 nm irradiation；Ferric chloride reaction is the positive；Bromine potassium phenol
Green reaction is the positive, indicates that there are carboxyls；Displaing amaranth after the heating of the vanillic aldehyde concentrated sulfuric acid, prompting the compound is phenol chemical combination
Object.ESI-MSm/z 137.0 [M-H]-, thus it is speculated that its molecular weight is 138.
?1H-NMR (300 MHz, CD3OD-d 4) in spectrum,δ H7.72 (1H, dd, J = 1.5 Hz, 7.8 Hz,
H-4), 7.32 (1H, dt, J = 1.5 Hz, 7.5 Hz, H-6), 6.78 (1H, d, J = 1.5 Hz, H-2),
6.73 (1H, m, H-5), prompt compound structure in there are 1,3 substituted phenyl ring.13C-NMR (75 MHz,
CD3OD-d 4) in spectrum,δ C173.4 be the carboxyl carbon signal on phenyl ring.δ C 113.9 (C-1), 120.0 (C-2), 163.3
(C-3), 118.1 (C-4), 131.5 (C-5), 136.6 (C-6) are carbon signal on phenyl ring.Above data and document report
(bibliography: the Artemisia anomala such as [5] Wen Jing, Shi Haiming, Zan jade-like stone chemical constitution study [J] Chinese herbal medicine, 2010,41
(6): data 870-873) are almost the same, therefore identify that the compound is 3-hydroxybenzoic acid, and determine the chemical combination
The chemical structural formula of object is determined as phenolic acid compound 2:
Phenolic acid compound 2
(3) Structural Identification of phenolic acid compound 3
The structure for purifying obtained compound 3 separated to the embodiment of the present invention 1 is identified:
The compound of phenolic acid 3 that the separation of embodiment 1 obtains, English name are 4-hydroxybenzoic acid.
Chemical formula are as follows: C7H6O3。
The correlation analysis of phenolic acid compound 3 is as follows:
Phenolic acid compound 3 is white needles, has blackening under ultraviolet 254 nm irradiation；Ferric chloride reaction is the positive, is indicated
Phenolic hydroxyl group exists；The green reaction of bromine potassium phenol is the positive, indicates that there are carboxyls；Displaing amaranth after the heating of the vanillic aldehyde concentrated sulfuric acid, prompting should
Compound is phenol compound.ESI-MSm/z 139.0[M+H]+, thus it is speculated that its molecular weight is 138.
1H-NMR (300 MHz, CD3OD-d 4) spectrum,δ H7.90 (2H, d, J = 8.4 Hz, H-2, 6), 6.83
(2H, d, J =8.4 Hz, H-3,5) prompt compound structure in there are a substituted phenyl ring in Isosorbide-5-Nitrae position.13C-NMR
(75 MHz, CD3OD-d 4) in spectrum,δ C173.4 be the carboxyl carbon signal on phenyl ring,δ C 122.7 (C-1), 133.3 (C-
2), 116.0 (C-3), 63.3 (C-4), 116.0 (C-5), 133.3 (C-6) are carbon signal on phenyl ring.
Above data and document report (bibliography: the oil tea root chemical component such as [2] Tong little Jing, Chen Chong, Li Xia
Research [J] Chinese herbal medicine, 2011,42 (10): data 1936-1938) are almost the same, therefore identify that the compound is 4-
Hydroxybenzoic acid, and determine that the chemical structural formula of the compound is determined as phenolic acid compound 3:
Phenolic acid compound 3
The inhibition melanin production determination of activity of 2 phenolic acid compound 1-3 of test example
This test example explores the inhibition melanin production activity of compound 1-3, and specific method and result are as follows:
1. the preparation of material
Mouse melanoma cells B16F10 is provided by Chinese Academy of Sciences's Shanghai biochemistry and Institute of Cell Biology.
The preparation of arbutin solution: arbutin 6.8mg is first dissolved in 1000μLDMSO prepares to obtain concentration to be 25.0mM's
Arbutin solution, then take 100.0μL concentration is the arbutin solution of 25.0mM, is added 2400.0μL DMEM obtains concentration
1000.0μThe arbutin solution of M.100.0 are taken againμL concentration is 1000.0μThe arbutin solution of M is added 900.0μL DMEM
Obtaining concentration is 100.0μThe arbutin solution of M.40.0 are taken againμL concentration is 1000.0μThe arbutin solution of M is added
1560.0μIt is 25.0 that L DMEM, which obtains concentration,μThe arbutin solution of M.
The preparation of monomeric compound sample: 3 isolated monomeric compounds are first dissolved in DMSO and prepare to obtain concentration
For each compound solution of 100.0mM, then take 10.0μL concentration is each compound solution of 100.0mM, is added 990.0μL
It is 1000.0 that DMEM, which obtains concentration,μEach compound solution of M, then take 100.0μL concentration is 1000.0μEach compound of M is molten
Liquid is added 900.0μIt is 100.0 that L DMEM, which obtains concentration,μEach compound solution of M.40.0 are taken againμL concentration is 1000.0μ
Each compound solution of M is added 1560.0μIt is 25.0 that L DMEM, which obtains concentration,μEach compound solution of M.
B16F10 cell is in the DMEM culture solution containing 10% fetal calf serum, in 37 oC, 5%CO2Keep saturated humidity item
It is cultivated under part, passage in 2-3 days is primary.2-3 min is digested with 0.5% pancreatin when passage, digestive juice is discarded, new culture solution is added
Piping and druming uniformly, is moved into new culture bottle by required cell concentration, adds complete culture solution to appropriate.
Method
The test of 2.1MTT method cytotoxic activity
The B16F10 cell of logarithmic growth phase, after collected by trypsinisation cell, with 5 × 103 The density in a/hole is inoculated into 96
In orifice plate, every hole is added 100μL contains the DMEM culture medium of 10% fetal calf serum, and incubation after cell adherent 80%, uses liquid-transfering gun for 24 hours
It inhales and abandons supernatant, cleaned 2 times with PBS, sample solution and arbutin solution are with 25μM, 100μM concentration is added in each hole, often
Hole is added 100μL sample solution, three parallel holes of every group of setting, parallel laboratory test is three times.It separately sets 3 holes and is added 100μL DMEM culture
Base is as a control group.Continue to be incubated for 48 h, takes out 96 orifice plates, be added 10 under the conditions of being protected from lightμThe MTT solution of L5 mg/mL continues
It is protected from light and is incubated for 3h, measure the absorbance value in each hole under 570nm wavelength using microplate reader, record as a result, counting according to the following equation
Calculate the survival rate of cell:
Cell survival rate (%)=(test group light absorption value/control group absorbance value) × 100%
2.2 inhibit melanin production active testing
The B16F10 cell of logarithmic growth phase, after collected by trypsinisation cell, every hole is added 500 in 24 porocyte culture platesμL
Cell suspension (every hole 5 × 103A cell).24 porocyte culture plates are placed in 37oC, 5%CO2It is cultivated in incubator for 24 hours to cell
It after adherent 80%, is inhaled with liquid-transfering gun and abandons supernatant, discard culture medium, PBS is cleaned 2 times.The corresponding drug containing training of 500 μ L is added in every hole
Base is supported as test group, three parallel holes of every group of setting, parallel laboratory test is three times；500 μ LDMEM culture mediums are added as sun in every hole
Property control group, three parallel holes of every group of setting, parallel laboratory test is three times.Pastille culture medium, positive controls are added 1μL100nM's
α-MSH.It is placed in 37oC, 5%CO2After cultivating 48h in incubator.Every hole is cleaned 2 times with PBS, removes supernatant, and pancreatin is added, disappears
Change cell.2MNaOH dissolution is added after collecting cell, 80oC heats 1h.Absorbance value is measured under the nm of λ=405, according to following
Mode counts each group melanin content, experimental result such as table 1.
Melanin content=(test group absorbance value/control group absorbance value) × 100%
Inhibiting effect of the 1 compound 1-3 of table to melanin and its toxicity to mouse melanoma cells B16F10
The results show that 3 phenolic acid compounds isolated from Oil-tea-cake have preferable suppression to the generation of melanin
System activity, and it is weaker to the toxicity of mouse melanoma cells B16F10, show 3 that the present invention is extracted from Oil-tea-cake
Phenolic acid compound is able to suppress the generation of melanin, it is possible to develop into and inhibit melanin production drug and product, realize
The recycling of agricultural by product and friendly environment society.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should all cover in protection scope of the present invention.
Claims (5)
1. extracting the method for phenolic acid compound in a kind of Oil-tea-cake, which comprises the following steps:
(1) Oil-tea-cake after extracting degreasing, 70% EtOH refluxing extraction after crushing, combined extract are concentrated under reduced pressure, obtain Oil-tea-cake
Medicinal extract；
(2) medicinal extract adds water to be suspended, and is placed in separatory funnel, is first extracted with ethyl acetate, then with extracting n-butyl alcohol, recycling design
Afterwards, acetic acid ethyl ester extract, ethyl acetate extract medicinal extract and n-butyl alcohol extract are respectively obtained；
(3) ethyl acetate extract medicinal extract is taken, by silica gel column chromatography, using EtOAc-CH3OH system gradient elution, obtains 5
Flow point E1, E2, E3, E4, E5；E1 is separated through the methods of silica gel column chromatography repeatedly, Sephadex LH-20 gel column chromatography, HPLC
Phenolic acid compound 2 and compound 3 are obtained,
Phenolic acid compound 2,
Phenolic acid compound 3；
E3 respectively obtains phenolic acid compound 1 through silica gel column chromatography repeatedly,
Phenolic acid compound 1.
2. extracting the method for phenolic acid compound in Oil-tea-cake according to claim 1, which is characterized in that the step
(1) Oil-tea-cake and 70% EtOH mass volume ratio are 1:10g/ml in, and 70% EtOH refluxing extraction number is 3 times, are extracted every time
Time is 3 hours.
3. extracting the method for phenolic acid compound in Oil-tea-cake according to claim 1, which is characterized in that the step
(2) ethyl acetate, the volume of n-butanol are identical as aqueous suspension in.
4. extracting the method for phenolic acid compound in Oil-tea-cake according to claim 1, which is characterized in that the step
(3) EtOAc-CH in3OH system gradient elution concentration is than being respectively 30:1,20:1,10:1,5:1,1:1.
5. extracting the method for phenolic acid compound in Oil-tea-cake according to claim 1, which is characterized in that the step
(3) isolated phenolic acid compound is suitable for preparation and inhibits melanin production drug and product.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008069079A (en) * | 2006-09-12 | 2008-03-27 | Croda Japan Kk | Cosmetic composition |
| CN102028042A (en) * | 2010-10-28 | 2011-04-27 | 福建省尤溪县沈郎食用油有限公司 | Method and equipment for preparing tea seed oil from tea seeds and extracting tea polyphenol from byproduct tea seed cake |
| CN102973469A (en) * | 2012-12-25 | 2013-03-20 | 江南大学 | Mild hand sanitizer containing camellia oil cake extract |
| CN106563037A (en) * | 2016-11-11 | 2017-04-19 | 中国林业科学研究院亚热带林业研究所 | Extraction method for extracting different forms of polyphenol in camellia seeds |
| CN108671079A (en) * | 2018-06-29 | 2018-10-19 | 刘磊 | Tea polyphenols method is extracted in a kind of Tea Production waste material |
-
2019
- 2019-04-09 CN CN201910278398.8A patent/CN110041190A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008069079A (en) * | 2006-09-12 | 2008-03-27 | Croda Japan Kk | Cosmetic composition |
| CN102028042A (en) * | 2010-10-28 | 2011-04-27 | 福建省尤溪县沈郎食用油有限公司 | Method and equipment for preparing tea seed oil from tea seeds and extracting tea polyphenol from byproduct tea seed cake |
| CN102973469A (en) * | 2012-12-25 | 2013-03-20 | 江南大学 | Mild hand sanitizer containing camellia oil cake extract |
| CN106563037A (en) * | 2016-11-11 | 2017-04-19 | 中国林业科学研究院亚热带林业研究所 | Extraction method for extracting different forms of polyphenol in camellia seeds |
| CN108671079A (en) * | 2018-06-29 | 2018-10-19 | 刘磊 | Tea polyphenols method is extracted in a kind of Tea Production waste material |
Non-Patent Citations (1)
| Title |
|---|
| ZHU WANFANG ，ET AL: "Chemical Constituents of the Seed Cake of Camellia oleifera and their Antioxidant and Antimelanogenic Activities", 《CHEMISTRY & BIODIVERSITY》 * |
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Application publication date: 20190723 |