CN101200417A - Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof - Google Patents
Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof Download PDFInfo
- Publication number
- CN101200417A CN101200417A CNA2007100316409A CN200710031640A CN101200417A CN 101200417 A CN101200417 A CN 101200417A CN A2007100316409 A CNA2007100316409 A CN A2007100316409A CN 200710031640 A CN200710031640 A CN 200710031640A CN 101200417 A CN101200417 A CN 101200417A
- Authority
- CN
- China
- Prior art keywords
- formula
- och3
- ncoom
- ncooh
- curcumin
- 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.)
- Pending
Links
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses curcumin deviate and the application in the preparation of skin-whitening and anti-freckle cosmetics and drugs; the experiment proves that curcumin deviate formula I has eminent inhibiting function on tyrosinase, and can be applied to skin-whitening and anti-freckle cosmetics and drugs; the chemical structure of the curcumin deviate is shown in formula I, the base group represented by R1, R2 is H in formula I, OCH3, OH; when R3 is OH in the formula I, the base group represented by R4 is OCH3, OOCCH3, O(CH2)nCOOH, O(CH2)nCOOM, wherein, n=1-5, M is Li, Na, K, Mg; or when R4 is OH in formula I, the base group represented by R3 is OCH3, OOCCH3, O(CH2)nCOOH, O(CH2)nCOOM, therein, n=1-5, M is Li, Na, K, Mg; or when the base group represented by R3, R4, the base group represented by R4, at the same time, is OCH3, OOCCH3, O(CH2)nCOOH, O(CH2)nCOOM, wherein, n=1-5, M is Li, Na, K, Mg.
Description
Technical field
The present invention relates to a kind of curcumin derivate and the application in preparation whitening cosmetics and medicine thereof.
Technical background
Diabetes are common chronic lifelong diseases of a kind of serious harm human health.The long-term hyperglycemia of diabetes causes taking place many complication to many tissues of body and organ generation harm, and these complication have become the main reason that diabetic subject's health and lives is threatened at present.The exploitation for the treatment of diabetes complicated disease drug is the focus that scientist studies always.Show that according to the Study on Pathogenesis to diabetic complication aldose reductase and non-glycosylation are the key factors in the diabetic complication genesis mechanism, the inhibitor of aldose reductase and non-glycosylation can be prevented and treated or the diabetes-alleviating complication effectively.But at present the effect of the aldose reductase inhibitor of exploitation and non-glycosylation inhibitor is undesirable, so seek efficiently, low toxicity, the little inhibitor of side effect be the task of top priority.
Discover that the red sage root and extract thereof have the activity of certain inhibition diabetic complication key enzyme aldose reductase, but tanshinone derivative yet there are no report as the research and the application of aldose reductase inhibitor.
Summary of the invention
The purpose of this invention is to provide as shown in the formula restraining effect and the application in preparation whitening cosmetics and medicine of the curcumin derivate shown in the I tyrosine oxidase.
A kind of curcumin derivate of the present invention is suc as formula shown in the I:
Formula I
R among the formula I
1, R
2The group of representative is: H, OCH
3, OH etc.;
R among the formula I
3During for OH, R
4The group of representative is: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM (n=1～5, M is Li, Na, K, Mg);
Or R among the formula I
4During for OH, R
3The group of representative is: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM (n=1～5, M is Li, Na, K, Mg);
Or R among the formula I
3, R
4The group of representative is simultaneously: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM (n=1～5, M is Li, Na, K, Mg).
The curcumin derivate of above-mentioned formula I is as the inhibitor of tyrosine oxidase.
Be used to whiten or the makeup or the medicine of removing beverage, wherein contain the curcumin derivate shown in the above-mentioned formula I, and pharmaceutically acceptable auxiliary.
Described makeup and medicine are to make tablet, pill, capsule, suspension agent or emulsion.
The invention has the beneficial effects as follows body outer suppressioning experiment, show that tanshinone derivative has the activity of remarkable inhibition aldose reductase by tyrosine oxidase.Curcumin derivate has restraining effect to tyrosine oxidase, preparation whiten or the makeup or the medicine of removing beverage have the bright skin effect of more obviously whitening.
Embodiment
The present invention will be further described by the following examples, the invention is not restricted to this.
Embodiment 1:Cur 01
200mg curcumine (1.62mmol) is dissolved in the 40ml acetone, adds 4mL ethyl chloroacetate and 40mg NaI, add Anhydrous potassium carbonate 314mg, reflux 24h.Filter, concentrated solution is used purification by silica gel column chromatography, and elutriant is a hexanaphthene: ethyl acetate: ethanol (4: 5: 1), obtain 229mg Compound C ur1, and productive rate is 78%.
Embodiment 2:Cur 03
200mg curcumine (1.62mmol) is dissolved in the 40ml acetone, adds 1mL ethyl chloroacetate and 10mg NaI, add Anhydrous potassium carbonate 80mg, reflux 24h.Filter, concentrated solution is used purification by silica gel column chromatography, and elutriant is a hexanaphthene: ethyl acetate: ethanol (4: 5: 1), obtain 178mg Compound C ur1, and productive rate is about 70%.
Embodiment 3:Cur 11
200mg is dissolved in the 20mL acetone (4: 1) by the Cur 01 of embodiment 1 preparation, adds 22mg KOH, constantly stir, detect Cur1 until TLC and react completely.With rare HCl acidification reaction liquid, acetone is removed in distillation, and uses ethyl acetate extraction.Collect ethyl acetate layer, use anhydrous sodium sulfate drying, distillation removes and desolvates, and with ethanol/water (2: 1) recrystallization, gets 177mg Cur11, and productive rate is 99%.
Embodiment 4:Cur 13
100mg is dissolved in the 10mL acetone (4: 1) by the Cur 03 of embodiment 2 preparations, adds 8mg KOH, constantly stir, detect Cur 03 until TLC and react completely.With rare HCl acidification reaction liquid, acetone is removed in distillation, and uses ethyl acetate extraction.Collect ethyl acetate layer, use anhydrous sodium sulfate drying, distillation removes and desolvates, and with ethanol/water (5: 1) recrystallization, gets 78mg Cur 13, and productive rate is 93%.
Embodiment 5: the inhibition screening of tyrosine oxidase
The condition determination of activity of enzyme reaction: with 110mmol/LL-2DOPA is substrate, L-2DOPA with 110mL 5mmol/L is dissolved in phosphate buffer soln (pH=6.8) earlier, place cuvette, add 3.6L phosphate buffer soln (pH=6.8), constant temperature 10in in 25 ℃ of waters bath with thermostatic control, go into 0.2L and contain the curcumin derivate DMSO solution and the 0.12mL 0.15g/L tyrosine oxidase aqueous solution of different concns, carry out enzymic catalytic reaction and measure A475. in this survey live body system, the whole mass concentration of enzyme is the definition of 6mg/L according to activity of enzyme reaction, under certain inhibitor concentration, activity of enzyme reaction is expressed as U
i, activity of enzyme reaction is not expressed as U when having inhibitor
0, relative activity (U
R) then calculate by following formula.
In the formula: A
1Be meant the absorbancy of the survey live body system of containing substrate, tyrosine oxidase, curcumin derivate; A
2Be meant and contain substrate, tyrosine oxidase, but do not contain the absorbancy of the survey live body system of curcumin derivate; A
0Be meant and contain substrate, but the absorbancy .IC50 that does not contain the survey live body system of tyrosine oxidase and Vanillin represents that enzymic activity is suppressed the concentration of 50% o'clock inhibitor.
Table 1 curcumin derivate is to the active IC of the inhibition of tyrosine oxidase
50
| Compound number | Cur 01 | Cur 03 | Cur 11 | Cur 13 |
| Enzymic activity U R(300 mM/L) | 13％ | 35％ | 83％ | 91％ |
| Tyrosine oxidase IC 50 (mM/L) | - | - | 56 | 39 |
The result shows that curcumin derivate has certain activity to the inhibition of tyrosine oxidase, and Compound C ur 11 and Cur13 are the most remarkable to the inhibition of tyrosine oxidase.
Embodiment 6:Cur 11 is used for the skin-lightening cosmetic experiment
Cur 11 made contain 5% ointment, select 50 volunteers on probation at random, require sooner or later once to smear face, used continuously 28 days.Add up by range estimation and questionnaire mode, the result shows: what the bright skin effect of obviously whitening was arranged is 38, accounts for 76%; What produce effect reaction is 11, accounts for 22%; What do not have any effect is 1, accounts for 4%.The light reaction that subtracts is in various degree all arranged after wherein having the trier of chloasma to use.
Claims (4)
1. a curcumin derivate is suc as formula shown in the I:
Formula I
R among the formula I
1, R
2The group of representative is: H, OCH
3, OH;
R among the formula I
3During for OH, R
4The group of representative is: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM
N=1～5 wherein, M is Li, Na, K, Mg;
Or R among the formula I
4During for OH, R
3The group of representative is: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM
N=1～5 wherein, M is Li, Na, K, Mg;
Or R among the formula I
3, R
4The group of representative is simultaneously: OCH3, OOCCH
3, O (CH
2) nCOOH, O (CH
2) nCOOM
N=1～5 wherein, M is Li, Na, K, Mg.
2. the described curcumin derivate of claim 1 is as the inhibitor of tyrosine oxidase.
3. one kind is used to whiten or the makeup or the medicine of removing beverage, wherein contains the curcumin derivate shown in the above-mentioned formula I, and pharmaceutically acceptable auxiliary.
4. application according to claim 3 is characterized in that described makeup or medicine are to make tablet, pill, capsule, suspension agent or emulsion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100316409A CN101200417A (en) | 2007-11-23 | 2007-11-23 | Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100316409A CN101200417A (en) | 2007-11-23 | 2007-11-23 | Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101200417A true CN101200417A (en) | 2008-06-18 |
Family
ID=39515815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100316409A Pending CN101200417A (en) | 2007-11-23 | 2007-11-23 | Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101200417A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101428129B (en) * | 2007-11-06 | 2011-10-05 | 天津天士力制药股份有限公司 | Effective component of turmeric rhizome, preparation method and uses thereof |
| CN106310117A (en) * | 2015-07-10 | 2017-01-11 | 康霈生技股份有限公司 | Phytoextraction composition used for inhibiting tyrosinase and reducing or preventing melanogenesis and pharmaceuticals and application thereof |
| CN107260610A (en) * | 2017-07-04 | 2017-10-20 | 拉芳家化股份有限公司 | A kind of skin whitener containing curcumin analogue |
| CN112094186A (en) * | 2019-05-30 | 2020-12-18 | 首都医科大学 | curcumin-4-OCH2CO2H-strontium, its synthesis, activity and application |
-
2007
- 2007-11-23 CN CNA2007100316409A patent/CN101200417A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101428129B (en) * | 2007-11-06 | 2011-10-05 | 天津天士力制药股份有限公司 | Effective component of turmeric rhizome, preparation method and uses thereof |
| CN106310117A (en) * | 2015-07-10 | 2017-01-11 | 康霈生技股份有限公司 | Phytoextraction composition used for inhibiting tyrosinase and reducing or preventing melanogenesis and pharmaceuticals and application thereof |
| CN107260610A (en) * | 2017-07-04 | 2017-10-20 | 拉芳家化股份有限公司 | A kind of skin whitener containing curcumin analogue |
| CN112094186A (en) * | 2019-05-30 | 2020-12-18 | 首都医科大学 | curcumin-4-OCH2CO2H-strontium, its synthesis, activity and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0820767B2 (en) | Use of melatonin derivatives for skin depigmentation and compositions comprising the same | |
| TWI480057B (en) | Use of caffeamide derivative | |
| HUP0203965A2 (en) | Indazole compounds and pharmaceutical compositions containing them | |
| Takahama et al. | Inhibition of xanthine oxidase activity by an oxathiolanone derivative of quercetin | |
| Moliné et al. | UVB photoprotective role of mycosporines in yeast: photostability and antioxidant activity of mycosporine-glutaminol-glucoside | |
| TWI736577B (en) | Salts of 5-aminolevulinic acid and derivatives | |
| CN101200417A (en) | Curcumin derivatives as well as uses in preparing whitening cosmetics and drugs thereof | |
| KR101529306B1 (en) | Combinations of vasoactive substances with estrogens and their use in the treatment of female sexual dysfunctions | |
| JP7233556B2 (en) | Use of Salidroside Derivatives in Skin Whitening Topical Preparations | |
| CN1318366A (en) | Cosmetics composition | |
| JP4975069B2 (en) | Tyrosinase inhibitor | |
| US5977184A (en) | Quercetin chalcone and methods related thereto | |
| CN104910119B (en) | One class cumarin substitution flavone derivative and its preparation method and application | |
| Li et al. | Discovery of matrix metalloproteinase inhibitors as anti-skin photoaging agents | |
| JP5049480B2 (en) | Whitening and antioxidants and active oxygen scavengers | |
| CN101708210B (en) | Application of pagodatree flower general flavone extract in preparing medicament for inhabiting cutaneous pigmentation | |
| JP2009155235A (en) | Melanogenesis inhibitor and skin-lightening external preparation comprising flavonoid analog or its physiologically permissible salt | |
| CN103179948A (en) | 2,2'-furoin derivatives and use thereof to lighten skin | |
| CN101012270A (en) | Tanshinone derivative and its application in preparing aldose reduction enzyme inhibitor pharmaceutical | |
| JP2007269705A (en) | c-kit GENE EXPRESSION INHIBITOR | |
| JP2019112354A (en) | Antiinflammatory agent and antiinflammatory composition | |
| Karakaya et al. | Kojic acid derivatives as potential anticancer agents: Synthesis and cytotoxic evaluation on A375 human malignant melanoma cells | |
| CN102070425A (en) | Diphenyl ketene and derivatives thereof serving as tyrosinase inhibitors and application thereof | |
| CA2435942A1 (en) | Use of an isothiocyanate, a thiocyanate or a mixture thereof as depigmenting agent | |
| JP2016003191A (en) | Melanogenesis inhibitor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080618 |