CN106924242A - The purposes of the composition comprising theaflavih digallate - Google Patents
The purposes of the composition comprising theaflavih digallate Download PDFInfo
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- CN106924242A CN106924242A CN201710236426.0A CN201710236426A CN106924242A CN 106924242 A CN106924242 A CN 106924242A CN 201710236426 A CN201710236426 A CN 201710236426A CN 106924242 A CN106924242 A CN 106924242A
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- digallate
- theaflavih
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
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- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Theaflavih digallate is included the present invention relates to one kind（TF3）Composition preparing the purposes of the treatment disease mediated medicine of tyrosinase, wherein theaflavih digallate（TF3）It is the main active component of the composition.The invention further relates to purposes of the above-mentioned composition in whitening class skin care item or cosmetics are prepared.Experiment proves that the composition has excellent melanin generation inhibition, whitening effect, and has excellent security.
Description
Technical field
Theaflavih digallate is included the present invention relates to one kind（TF3）Composition prepare treatment tyrosinase be situated between
Lead the purposes of the medicine of disease.Another aspect of the present invention is related to one kind comprising theaflavih digallate（TF3）Composition
Purposes in whitening class skin care item or cosmetics are prepared.In the present compositions, theaflavih digallate（TF3）
It is main active component or sole active component.
Background technology
Theaflavins compound（Theaflavins）Be a class be soluble in ethyl acetate, with benzo Zhuo phenolic ketone
（Benzotropolone）The general name of the compound of structure, is aoxidized by catechins and is formed, be determine black tea color, smell and taste and
The important component of quality.The theaflavin component of clear and definite structure has 22 kinds, wherein theaflavin（Theaflavin, TF1）, tea it is yellow
Element -3- gallates（Theaflavins-3-gallate, TF2A）, TF2B（theaflavins-
3 '-gallate, TF2B）, theaflavih digallate（Theaflavins-3,3 '-digallate, TF3）With table tea Huang Gallate
Spirit -3- gallates（Epitheaflagallin-3-gallate, TF4）It is main component.Theaflavins compound is red
The main component of tea, is described as " soft gold " in tealeaves, safe.Theaflavins compound is also lived with extensive physiology
Property and pharmacological action, such as anti-disease of cardiovascular system, anti-inflammatory, immunological regulation, antitumor, antiviral, anti-diabetic.
Tyrosinase (Tyrosinase) is the key enzyme of organism B16 cell, and its abnormal overexpression can cause people
The pigmentation disease of body.Tyrosinase has various features catalysis activity, and it both can be as tyrosine hydroxylase, many
Bar oxidizing ferment, can as 5,6- dihydroxy indole oxidizing ferment, and be again the key enzyme of melanocyte biosynthesis, rate-limiting enzyme.
Tyrosinase primarily serves two-step catalysis effect in melanin forming process：The first step is that tyrosinase plays monophenolase work
Property, make tyrosine that hydroxylating generation DOPA to occur（L-DOPA）；Second step is that tyrosinase plays o-diphenolase activity, is made many
Bar is oxidized to DOPA quinone (o-dopaquinone), the further oxidation polymerization generation melanin of DOPA quinone.Therefore, tyrosinase suppression
Preparation can treat pigmentation disorder such as freckle, chloasma, senile plaque expelling etc. common at present, be widely used in cosmetics and doctor
Medicine industry, its brightening agent is mostly tyrosinase inhibitor in such as popular in the market skin-lightening cosmetic.Additionally, in food
In industry, tyrosinase can cause fruits and vegetables that brown stain occurs, and develop dynamical tyrosinase inhibitor in food industry
Field is also significant.It can be seen that, tyrosinase inhibitor efficiently, safe has broad application prospects.
Although existing cosmetic composition has certain improvement, many groups in lightening or whitening the skin
Compound whitening effect is also to be reinforced.Therefore, a kind of lightening compositions with enhanced whitening effect are still expected in this area.
The content of the invention
The present invention is based on inventors be surprised to learn that theaflavih digallate（TF3）Compared in theaflavin component
Other monomers have the activity of much higher suppression tyrosinase and make.Theaflavih digallate（TF3）It is this aobvious
It is dramatically different that the tyrosinase inhibitory activity of work suppresses result of study with the prior art to the tyrosinase of theaflavin component.Should
The activity for suppressing tyrosinase is found to be so as to play disease treatment, whitening function there is provided preferably selection.
One aspect of the present invention is provided and includes theaflavih digallate（TF3）Composition prepare treatment tyrosinase
The purposes of disease mediated medicine, wherein theaflavih digallate（TF3）It is the main active component of the composition.
In some implementation methods, the disease is the increased disease of melanin, idiopathic black spot, photosensitization or the excessive pigment of cicatricial
It is calm.In some embodiments, the theaflavih digallate（TF3）It is the sole active component of the composition.
Another aspect of the present invention provides a kind of comprising theaflavih digallate（TF3）Composition prepare whitening class
Purposes in skin care item or cosmetics, wherein theaflavih digallate（TF3）It is the main active component of the composition.
In some embodiments, the whitening class skin care item or cosmetics be emulsion, washing lotion, cream, foam, gel, soap bar, rod,
Facial mask, cotton piece or patch.In some embodiments, the theaflavih digallate（TF3）It is the composition
Sole active component.
Composition of the invention can include other skin-whitening agents.Preferably, the skin-whitening agents are selected from vitamin B3
Compound or derivatives thereof, such as niacin, nicotinic acid, niacinamide or other well known skin-whitening agents, such as ursolic acid, aloe
Extract, ammonium lactate, azelaic acid, kojic acid, citrate, ellagic acid, glycolic, green-tea extract, quinhydrones, lemon extract,
Linoleic acid, magnesium ascorbyl phosphate, vitamin for example vitamin B6, vitamin B12, vitamin C, vitamin A, dicarboxylic acids,
Resorcinol derivatives, hydroxycarboxylic acid such as lactic acid and their salt, such as sodium lactate, and its mixture.
Composition of the invention can be optionally comprising one or more routine and be available commercially suitable for this kind of
The acceptable composition of cosmetics in preparation.These compositions can include as emulsifying agent, surfactant, emollient, essential oil,
The materials such as humidizer, stabilizer, viscosity modifier, gelling agent, wetting agent, colouring agent.The technical staff in cosmetic formulations field
It should be appreciated that individual other compound will be based in part on the method for preparing to apply being selected, and usually can be used for matching somebody with somebody
The cosmetic composition for making dermal compositions of the invention is international cosmetic ingredient dictionary and handbook (International
Cosmetic Ingredient Dictionary and Handbook) in listed composition, but be not limited to this.
Brief description of the drawings
Fig. 1 is influence of the theaflavin component to B16 cell proliferation rates.
Fig. 2 is influence of the kinds of theaflavin monomer compound to B16 cell proliferation rates.
Specific embodiment
In the present invention, " theaflavin component " refer to containing theaflavin, TF-3-G, theaflavin -3 ' -
The compound of gallate, theaflavih digallate and table tea Huang gallin -3- gallates, may in the compound
Also include other materials." kinds of theaflavin monomer compound " refer to theaflavin, TF-3-G, theaflavin -3 '-do not have
The monomeric compound of infanticide acid esters, theaflavih digallate and table tea Huang gallin -3- gallates.
Theaflavin（TF1）, TF-3-G（TF2A）, TF2B（TF2B）, tea it is yellow
Plain digallic acid ester（TF3）With table tea Huang gallin -3- gallates（TF4）Can be by appropriate side known to art technology
Method is obtained, and a kind of exemplary preparation method is referring to Chinese patent ZL200610083828.3.
In the present invention, the increased disease of melanin includes, but are not limited to black spot or in the black of gestation generation
Pinta (" mask of pregnancy ") or due to black spot caused by oestrone/progestin contraceptive；Due to benign melanocytic activity
Other local pigments that strong and propagation causes are excessively calm, such as senile pigmented spots (" senile plaque expelling ")；Disease correlation pigment mistake
Degree is calm；Accidental hyperpigmentation, such as due to photosensitization, genetic constitution, chemical ingestion or other contact, ages
With hyperpigmentation caused by scar after damage.
Influence and IC of the theaflavins compound of embodiment 1 to diphenol enzyme activity50
1. material and instrument
Levodopa（L-DOPASIGMA companies）, Mushroom Tyrosinase（SIGMA companies）, EGCG
Ester（EGCG, purity >=99%, Shanghai Jiang Lai bio tech ltd）, theaflavin component（Theaflavin total content is 85.78%,
Wherein TF1 is that 21.15%, TF2B is that 18.90%, TF3 is that 19.02%, TF4 is 14.29% for 12.42%, TF2A）, theaflavins are each
Monomer TF1, TF2A, TF2B, TF3 and TF4（Self-control, purity >=95%, HPLC methods）, it is pure that other reagents are commercially available analysis.
96 orifice plates（Corning Incorporated）, the multi-function microplate reader work stations of Flex Station 3（The U.S.
Moleculardevices companies, equipped with Soft Max Pro V5.2 data handling systems）, AG285 type analysis balances（0.1
Mg/0.01 mg, Mettler Toledo, Switzerland）,
2. experimental technique
2.1 o-diphenolase activities are tested
Phosphate buffer is accurately drawn according to table 1（PBS, pH 6.8）, sample（PBS dissolves, wherein containing DMSO< 0.5%）With
Tyrosinase（PBS, 45 U/mL）A, B, C, D group reaction solution are prepared, is mixed, 30 DEG C of 10 min of incubation add substrate L-DOPA
（1.5 mM）Mix, 30 DEG C of 5 min of reaction determine OD values at 475 nm, and A groups and C groups set two multiple holes, take average.
The reaction solution of table 1 is constituted and volume
2.2 inhibition of enzyme activity rates are calculated
The OD of above-mentioned test result475Average value is calculated according to formula below, obtains the inhibiting rate to tyrosinase activity.
Inhibiting rate %=[(A-B)-(C-D)]*100%/(A-B), in formula,A~DRespectively each group OD475Average value.
3. experimental result
The concentration of immobilized substrate and enzyme, determines inhibiting rate of the various concentrations sample to o-diphenolase activity, with sample concentration and suppression
Rate does effect curve, obtains IC of the theaflavins compound to diphenol enzyme inhibition activity50, the results are shown in Table 2.As shown in Table 2, monomer
The IC of compound50Value（μmol/L）It is ascending to be arranged as：TF3 <TF1 <TF2A <TF4<TF2B < EGCG <Ursin；
The IC of TF350Had a clear superiority compared with positive control EGCG and ursin.
Inhibitory activity IC of the theaflavins compound of table 2 to Mushroom Tyrosinase diphenolase50
Influence of the theaflavins compound of embodiment 2 to B16 mouse black-in tumor cell proliferation rates
1. material and instrument
B16 mouse black-in tumor cells（The internal lab present of pharmaceutical college of Zhongshan University）；Modified form RPMI-1640 culture mediums；It is double
Anti- (penicillin, streptomysin)（Hyclone companies）；Hyclone（Hangzhou Tian Hang bio tech ltd）；Trypsase
（Containing 0.02%EDTA, without phenol red, Ji Nuo biological medicine technologies Co., Ltd）；3- (4,5- dimethylthiazoles -2) -2,5- two
Phenyl tetrazole bromide（MTT, Guangzhou Wei Jia Science and Technology Ltd.s）；PBS powder（PH 7.0-7.8, doctor's moral bioengineering has
Limit company）；Levodopa（L-DOPA, Sigma company）；Epigallo-catechin gallate (EGCG)（EGCG, purity >=99%, on
Hai Jianglai bio tech ltd）；Theaflavin component（Theaflavin total content is 85.78%）；Each monomeric compound of theaflavin
（Purity >=95%）；Dimethyl sulfoxide (DMSO), TritonX-100（MP Biomedicals companies）；It is pure that other reagents are analysis.
The double two-sided clean work station of SW-CJ-2F types（Purifying Equipment Co., Ltd., Suzhou）, CO2gas incubator (U.S.
State Thermo), inverted microscope (Chongqing photoelectricity), Flex Station3 multi-function microplate readers (Moleculardevices), carefully
Born of the same parents' tally (Guangzhou Wei Jia Science and Technology Ltd.s).
2. experimental technique
The culture and passage of 2.1 cells
Aseptically, B16 cells are inoculated in culture medium containing RPMI-1640（Containing 10% hyclone, 1% is dual anti-）Culture
In ware, in 37 DEG C of CO2gas incubators（5% CO2Saturated humidity）Middle culture.Every 3 d, 0.25% trypsase（Containing 0.02%
EDTA）Had digestive transfer culture is once.
Influence of the 2.2 theaflavins compounds to B16 cell proliferation rates
Cell growth to nearly Fusion Strain is treated, through 0.25% Trypsin Induced, is collected and cell counting count board is put into inverted microscope
Under cell suspending liquid is counted, adjustment cell concentration be 4 × 105Individual/mL, is inoculated in 96 well culture plates, per the μ L of hole 100
（Cell number 4 × 104Individual/hole）, in 37 DEG C of CO2gas incubators（5% CO2Saturated humidity）Middle overnight incubation, it is adherent after, abandon
Clear liquid, the μ L of Contained Serum nutrient solution 200 of respective concentration are added per hole, and each concentration sets 6 holes, and control group adds nutrient solution, training
After supporting 72 h, the μ L of 5 g/L MTT 20 are added per hole, continue to put CO2The h of incubator culture 4, then sucks nutrient solution, is added per hole
150 μ L DMSO, shake well culture plate determines every hole absorbance OD with ELIASA490, the inhibiting rate (%) of cell proliferation=
[(blank control group OD490﹣ drug-treated groups OD490)/blank control group OD490] ×100%。
3. result and analysis
Influence of the 3.1 theaflavin components to B16 cell proliferation rates
Theaflavin component is determined using mtt assay（Theaflavin total content is 85.78%）Influence to B16 cells propagation, can by Fig. 1
See, with the increase of sample concentration, cell proliferation inhibition strength increases, and there is obvious dose-effect relationship.It is different by drawing
The inhibitory action curve that concentration samples are bred to B16 cells, tries to achieve the IC that theaflavin component suppresses B16 cells propagation50It is 51.72
μg/mL。
Influence of each monomeric compound of 3.2 theaflavin to B16 cell proliferation rates
The inhibitory action that different compounds are bred under 50 μm of ol/L and 100 μm of concentration of ol/L to B16 cells is investigated, as a result
See Fig. 2.With the increase of concentration, inhibiting rate is also accordingly increased, and the suppression of cell proliferation has dose-effect relationship, in 100 μ
Under the high concentration of mol/L, the inhibitory activity that each monomeric compound of theaflavin is bred to B16 cells（Inhibiting rate 25.2% ~ 60.2%）
Than positive control EGCG（67.8%）It is small.In the case that concentration is 50 μm of ol/L, each kinds of theaflavin monomer compound has to B16 cells
There is different degrees of inhibitory action, inhibiting rate is descending to be ordered as：TF3>TF2A>TF2B>EGCG>TF4>TF1；Compound
Inhibiting rate of the inhibiting rate of TF2A, TF2B and TF3 than positive control EGCG（23.6%）Height, its inhibiting rate is respectively 36.65%,
29.90% and 44.53%；The inhibitory action of TF and TF4 is more slightly lower than positive control EGCG, and its inhibiting rate is respectively 21.68% He
13.51%。
Influence of each monomeric compound of the theaflavin of embodiment 3 to B16 intracellular tyrosine enzyme activities
1. laboratory apparatus and material
Referring to the laboratory apparatus of embodiment 2 and material.
2. experimental technique
2.1 B16 cell culture passages methods
Referring to the method part of embodiment 2.
Influence of 2.2 theaflavin compounds to B16 intracellular tyrosine enzyme activities
Treat cell growth to nearly Fusion Strain through 0.25% Trypsin Induced, collect and adjust cell concentration for 4 × 105Individual/
ML, is inoculated in 96 well culture plates, per the μ L of hole 100, puts 37 DEG C, 5% CO2Cultivated in saturated humidity environment, overnight, treat adherent
Afterwards, supernatant is abandoned, the μ L of Contained Serum nutrient solution 200 of respective concentration is added per hole, each concentration sets 6 holes, and control group adds training
Nutrient solution, after 72 h of culture, abandons supernatant, is washed with PBS 1 time, adds the PBS that volume fraction is 1% TritonX-100 to delay per hole
The μ L of fliud flushing 90, are subsequently adding the L-DOPA of 20 μ L（The mg/mL of concentration 0.05）, fully mix, room temperature is put after 24 hours 490
Nm mensuration absorbances.To inhibiting rate (%)=(the control group OD of enzyme activity490﹣ drug-treated groups OD490)/control group OD490×100%
（It is corrected with L-DOPA）.By drawing inhibitory action curve of the various concentrations sample to B16 intracellular tyrosine enzymatic activitys,
Try to achieve IC of each sample to B16 intracellular tyrosine enzyme inhibitions50。
3. experimental result
The suppression of theaflavin component and each monomeric compound to B16 intracellular tyrosine enzymatic activitys is tested using L-DOPA oxidizing process
Make and use, the results are shown in Table 3.
Inhibitory activity IC of the theaflavins compound of table 3 to B16 intracellular tyrosine enzymes50
As shown in table 3, each kinds of theaflavin monomer compound has different degrees of inhibitory action to intracellular tyrosine enzymatic activity, suppression
Rate processed is descending to be ordered as：TF3> TF2A≥ TF2B>TF1 >=TF4, TF3 are most strong to the inhibitory action of desmoenzyme vigor,
IC50It is 27.94 μm of ol/L（24.27 μg/mL）.IC of 5 kinds of monomeric compounds to intracellular enzyme activity inhibiting rate50It is significantly low
In the IC of cell proliferation inhibiting rate50, illustrate that each compound has the effect for suppressing B16 intracellular tyrosine enzymatic activitys, pass through
The effect for suppressing intracellular tyrosine enzymatic activity reaches the purpose for suppressing melanogenesis.
Claims (6)
1. it is a kind of to include theaflavih digallate（TF3）Composition preparing the treatment disease mediated medicine of tyrosinase
Purposes, wherein theaflavih digallate（TF3）It is the main active component of the composition.
2. purposes according to claim 1, wherein the disease is idiopathic black spot, photosensitization or the excessive color of cicatricial
It is plain calm.
3. purposes according to claim 1, wherein theaflavih digallate（TF3）It is unique work of the composition
Property component.
4. it is a kind of to include theaflavih digallate（TF3）Use of the composition in whitening class skin care item or cosmetics are prepared
On the way, wherein theaflavih digallate（TF3）It is the main active component of the composition.
5. purposes according to claim 4, wherein the whitening class skin care item or cosmetics are emulsion, cream, washing lotion, bubble
Foam, gel, soap bar, rod, facial mask, cotton piece or patch.
6. the purposes according to claim 4 or 5, wherein theaflavih digallate（TF3）Be the composition only
One active component.
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| CN201710236426.0A CN106924242A (en) | 2017-04-12 | 2017-04-12 | The purposes of the composition comprising theaflavih digallate |
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| CN201710236426.0A CN106924242A (en) | 2017-04-12 | 2017-04-12 | The purposes of the composition comprising theaflavih digallate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110959851A (en) * | 2019-11-18 | 2020-04-07 | 青海晨菲制药有限公司 | Application of agaricus bisporus gallic acid in functional food |
| CN112545909A (en) * | 2020-12-14 | 2021-03-26 | 湖南农业大学 | Theaflavin composition and application thereof |
| CN112915077A (en) * | 2021-02-18 | 2021-06-08 | 南昌大学附属口腔医院(江西省口腔医院) | Oral acid etching agent and preparation method and application thereof |
| CN114983845A (en) * | 2022-04-22 | 2022-09-02 | 昆明理工大学 | Application of gallic acid polymer compound in preparation of whitening product |
-
2017
- 2017-04-12 CN CN201710236426.0A patent/CN106924242A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| YURIKO YAMAOKA等: "Effects of Theaflavins on Melanin Biosynthesis in Mouse B16 Melanoma Cells", 《BIOSCI. BIOTECHNOL. BIOCHEM.》 * |
| 周盈利等: "茶黄素类化合物对酪氨酸酶的抑制作用", 《食品科技》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110959851A (en) * | 2019-11-18 | 2020-04-07 | 青海晨菲制药有限公司 | Application of agaricus bisporus gallic acid in functional food |
| CN112545909A (en) * | 2020-12-14 | 2021-03-26 | 湖南农业大学 | Theaflavin composition and application thereof |
| CN112545909B (en) * | 2020-12-14 | 2022-06-21 | 湖南农业大学 | Theaflavin composition and application thereof |
| CN112915077A (en) * | 2021-02-18 | 2021-06-08 | 南昌大学附属口腔医院(江西省口腔医院) | Oral acid etching agent and preparation method and application thereof |
| CN114983845A (en) * | 2022-04-22 | 2022-09-02 | 昆明理工大学 | Application of gallic acid polymer compound in preparation of whitening product |
| CN114983845B (en) * | 2022-04-22 | 2023-06-23 | 昆明理工大学 | Application of gallic acid polymer compound in preparation of whitening products |
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Application publication date: 20170707 |