CN116947944A

CN116947944A - Potato anthocyanin derivative norsetanin and application thereof

Info

Publication number: CN116947944A
Application number: CN202310941150.1A
Authority: CN
Inventors: 王洪伦; 欧阳健; 铁芳芳
Original assignee: Northwest Institute of Plateau Biology of CAS
Current assignee: Northwest Institute of Plateau Biology of CAS
Priority date: 2023-07-28
Filing date: 2023-07-28
Publication date: 2023-10-27

Abstract

The invention discloses a potato anthocyanin derivative norsetanin and application thereof, relates to the technical field of compound separation, and adopts chromatographic technology to systematically separate and purify anthocyanin components in black diamond potatoes to obtain potato anthocyanin derivatives for the first time: norsetanin, the isolated potato anthocyanin derivative of the invention has an inhibitory effect on the activity of tyrosinase.

Description

Potato anthocyanin derivative norsetanin and application thereof

Technical Field

The invention relates to the technical field of compound separation, in particular to a potato anthocyanin derivative norsetanin and application thereof.

Background

Anthocyanin is a compound formed by combining anthocyanin and sugar through glycosidic bonds, and widely exists in cell fluids of flowers, fruits, stems, leaves and root organs of plants, so that the anthocyanin presents different colors from red, purple red to blue and the like. Anthocyanins are flavonoids, a family of compounds that appear red in a class of substances based on a flavone core. The actions and effects mainly include antioxidation, anti-inflammatory, cardiovascular health improvement, etc., and specific effects vary depending on individual differences.

Can help neutralize free radicals in vivo, reduce damage to cells caused by oxidative stress, and prevent chronic diseases such as heart disease, cancer and neurodegenerative diseases. Can also relieve inflammatory reaction, promote inflammation resolution, and relieve inflammation related diseases such as arthritis and inflammatory bowel disease. Anthocyanin can also help to reduce blood pressure, improve blood circulation, and reduce risk of cardiovascular disease. They can enhance vascular elasticity, reduce platelet aggregation, and prevent arteriosclerosis and thrombosis. In addition, anthocyanin has certain benefit on brain health, and researches show that the anthocyanin can improve memory and strengthen learning ability and has certain protection effect on preventing and delaying cognitive function decline, such as senile dementia.

Anthocyanin has unique functionality, and thus has been used for scavenging free radicals in vivo, proliferating lutein, resisting tumor, resisting cancer, resisting inflammation, inhibiting lipid peroxidation and platelet aggregation, preventing diabetes, reducing weight, protecting vision, etc. As a natural pigment, the natural pigment is safe, nontoxic and has a plurality of health care functions for human bodies, and has been applied to industries such as foods, health care products, cosmetics, medicines and the like.

"Black diamond" potato (Solanum tuberosum L.) is a good food crop and is of increasing interest because of its high anthocyanin content, the natural active ingredient. At present, little research is done on the production and composition of anthocyanin derivatives in black diamond.

Disclosure of Invention

The invention aims to provide a potato anthocyanin derivative norsetanin and application thereof, wherein chromatographic technology is adopted to systematically separate and purify anthocyanin component derivatives in black diamond potatoes, thus obtaining anthocyanin new derivative norsetanin, and simultaneously finding that the anthocyanin new derivative norsetanin has an inhibition effect on tyrosinase activity, thus inhibiting melanin, and further being applied to cosmetics for whitening and removing freckles.

Based on the above research, the present invention provides a compound of formula I norsetanin or its individual optical isomers, individual crystalline forms, pharmaceutically acceptable salts, hydrates or solvates thereof:

meanwhile, the experiment proves that the 4-O- (p-coumaryl) rhamnose separated and purified at the same position (F2-3) as the compound of the formula I also has similar activity, and the inventor deduces that the purified position F2-3 contains the compound of the formula I and the 4-O- (p-coumaryl) rhamnose, and the F2-3 also certainly maintains the biological activity of the two compounds.

Based on the above, the invention also provides a black diamond potato extract, and the preparation method comprises the following steps:

(1) 70-80% ethanol extract of black diamond potato, loading on nonpolar or weak polar macroporous adsorption resin, eluting with water and 95% ethanol in sequence, and taking the 95% ethanol eluting part as crude extract;

(2) The crude extract was eluted through a DAC-HB50 chromatographic column with mobile phase: the water phase is 0.1-1.0% trifluoroacetic acid water, and the organic phase is acetonitrile; elution gradient: 0-40 min, 15-35% acetonitrile, and flow rate of 50ml/min; f1, F2, F3 and F4 are obtained by segmentation, and F2 with the retention time of 27.0-29.0 min is obtained;

(3) F2 was separated using a C18 preparative column of 5um,100A,20 x 250mm size, mobile phase: the water phase is 0.1-1.0% trifluoroacetic acid water, and the organic phase is acetonitrile; the elution gradient conditions are 0-50-55-60min, 15-27.5-95% and the flow rate is 8ml/min, F2-1-F2-8 are sequentially obtained, F2-3 with the retention time of 28.5-31.0 min is obtained, and the black diamond potato extract is obtained.

Wherein the nonpolar macroporous resin is selected from HPD-100, HPD-300, D-101, X-5, and H103; the macroporous resin with weak polarity is selected from AB-8, DA-201 and HPD-400.

Further, the concentration of trifluoroacetic acid water was 0.6%.

The invention also provides application of the potato anthocyanin derivative norsetanin or the extract, namely application in preparation of a product for inhibiting tyrosinase activity.

Tyrosinase is an important biological enzyme with double catalytic functions existing in human body, and is involved in regulating melanin synthesis process in human body, has a key effect on human body melanin formation, and can produce pigmentary diseases when melanin metabolic process or epidermal melanin pigmentation is disordered, and is divided into pigment removal and hyperpigmentation.

Tyrosinase, also called polyphenol oxidase, catechol oxidase, chen Ganlao enzyme, etc., is a kind of copper-containing oxidoreductase containing multiple subunits with complex structures, and is widely existing in microorganisms, animals, plants and humans. Tyrosinase is an oxidase and is the rate-limiting enzyme that regulates melanin production.

Human melanin is synthesized in melanocytes and forms melanin, requiring two most basic substances:

the first is tyrosine, which is a substrate for the reaction; the second is tyrosinase, which is a catalyst for reaction and can convert tyrosine into melanin, and a large number of medical researches and clinical experiments prove that tyrosinase is a key enzyme for melanin synthesis, and tyrosine cannot be converted into melanin without the participation of tyrosinase.

The tyrosinase activity is increased, a large amount of tyrosinase is catalyzed to convert into melanin, a large amount of melanin appears in a short time, the metabolism of a human body is not timely, pigmentation is caused, skin problems such as nevus taitianus, freckle, chloasma, senile plaque, black nevus and the like appear, and the skin problems have close relation with the aging of people. Inhibiting tyrosinase activity, and can effectively reduce melanin generation and reduce formation of macula.

Further, the use is in the preparation of a melanin inhibiting product.

Further, the application is the application in preparing whitening and freckle removing products.

Further, the product is a pharmaceutical, cosmetic norsetanin.

A whitening product contains at least the above-mentioned potato anthocyanin derivative norsetanin or extract as active ingredient.

Further, the product is selected from the group consisting of a mask, a cream, an emulsion, a toner, and a facial cleanser.

The term "pharmaceutically acceptable" as used herein is meant to include any material which does not interfere with the effectiveness of the biological activity of the active ingredient and which is not toxic to the host to which it is administered.

The pharmaceutically acceptable auxiliary materials are the general names of all additional materials except the main drugs in the medicine, and the auxiliary materials have the following properties: (1) no toxic or side effect to human body; (2) The chemical property is stable, and is not easily influenced by temperature, pH, preservation time and the like; (3) No incompatibility with the main medicine, and no influence on the curative effect and quality inspection of the main medicine; (4) does not interact with the packaging material. Adjuvants in the present invention include, but are not limited to, fillers (diluents), lubricants (glidants or anti-adherents), dispersants, wetting agents, binders, conditioning agents, solubilizing agents, antioxidants, bacteriostats, emulsifiers, disintegrants, and the like. The binder comprises syrup, acacia, gelatin, sorbitol, tragacanth, cellulose and its derivatives (such as microcrystalline cellulose, sodium carboxymethylcellulose, ethylcellulose or hydroxypropyl methylcellulose), gelatin slurry, syrup, starch slurry or polyvinylpyrrolidone; the filler comprises lactose, sugar powder, dextrin, starch and its derivatives, cellulose and its derivatives, inorganic calcium salt (such as calcium sulfate, calcium phosphate, calcium hydrogen phosphate, precipitated calcium carbonate, etc.), sorbitol or glycine, etc.; the lubricant comprises aerosil, magnesium stearate, talcum powder, aluminum hydroxide, boric acid, hydrogenated vegetable oil, polyethylene glycol and the like; disintegrants include starch and its derivatives (e.g., sodium carboxymethyl starch, sodium starch glycolate, pregelatinized starch, modified starch, hydroxypropyl starch, corn starch, etc.), polyvinylpyrrolidone, microcrystalline cellulose, etc.; the wetting agent comprises sodium dodecyl sulfate, water or alcohol, etc.; the antioxidant comprises sodium sulfite, sodium bisulphite, sodium metabisulfite, dibutyl benzoic acid and the like; the bacteriostat comprises 0.5% phenol, 0.3% cresol, 0.5% chlorobutanol and the like; the regulator comprises hydrochloric acid, citric acid, potassium hydroxide (sodium), sodium citrate, buffer (including sodium dihydrogen phosphate and disodium hydrogen phosphate), etc.; the emulsifier comprises polysorbate-80, sorbitan without acid, pluronic F-68, lecithin, soybean lecithin, etc.; the solubilizer comprises Tween-80, bile, glycerol, etc. The term "pharmaceutically acceptable salt" refers to salts of the compounds of the invention with acids or bases that are suitable for use as medicaments. The acid base is a broad Lewis acid base. Suitable salts forming acids include, but are not limited to: inorganic acids such as hydrochloric acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, nitric acid, and phosphoric acid, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, lactic acid, malic acid, tartaric acid, citric acid, picric acid, methanesulfonic acid, benzenesulfonic acid, and the like; acidic amino acids such as aspartic acid and glutamic acid.

The mode of administration of the compounds or pharmaceutical compositions of the present invention is not particularly limited, and representative modes of administration include (but are not limited to): oral, parenteral (intravenous, intramuscular or subcutaneous), and topical administration.

Solid dosage forms for oral administration include capsules, tablets, pills, powders and granules. In these solid dosage forms, the active compound is admixed with at least one conventional inert excipient (or carrier), such as sodium citrate or dicalcium phosphate, or with the following ingredients: (a) Fillers or compatibilizers, for example, starch, lactose, sucrose, glucose, mannitol and silicic acid; (b) Binders, for example, hydroxymethyl cellulose, alginate, gelatin, polyvinylpyrrolidone, sucrose and acacia; (c) humectants, e.g., glycerin; (d) Disintegrants, for example, agar-agar, calcium carbonate, potato or tapioca starch, alginic acid, certain complex silicates, and sodium carbonate; (e) a slow solvent, such as paraffin; (f) an absorption accelerator, e.g., a quaternary amine compound; (g) Wetting agents, such as cetyl alcohol and glycerol monostearate; (h) an adsorbent, for example, kaolin; and (i) a lubricant, for example, talc, calcium stearate, magnesium stearate, solid polyethylene glycol, sodium lauryl sulfate, or mixtures thereof. In capsules, tablets and pills, the dosage forms may also comprise buffering agents.

Solid dosage forms such as tablets, dragees, capsules, pills and granules can be prepared with coatings and shells, such as enteric coatings and other materials well known in the art. They may contain opacifying agents and the release of the active compound or compounds in such compositions may be released in a delayed manner in a certain part of the digestive tract. Examples of embedding components that can be used are polymeric substances and waxes. The active compound may also be in the form of microcapsules with one or more of the above excipients, if desired.

Liquid dosage forms for oral administration include pharmaceutically acceptable emulsions, solutions, suspensions, syrups or tinctures. In addition to the active compound, the liquid dosage forms may contain inert diluents commonly used in the art such as, for example, water or other solvents, solubilizing agents and emulsifiers such as ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, propylene glycol, 1, 3-butylene glycol, dimethylformamide and oils, in particular, cottonseed, groundnut, corn germ, olive, castor and sesame oils or mixtures of these substances and the like.

In addition to these inert diluents, the compositions can also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, and perfuming agents.

Suspensions, in addition to the active compounds, may contain suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum methoxide and agar-agar or mixtures of these substances, and the like.

Compositions for parenteral injection may comprise physiologically acceptable sterile aqueous or anhydrous solutions, dispersions, suspensions or emulsions, and sterile powders for reconstitution into sterile injectable solutions or dispersions. Suitable aqueous and nonaqueous carriers, diluents, solvents or excipients include water, ethanol, polyols and suitable mixtures thereof.

Dosage forms of the compounds of the present invention for topical administration include ointments, powders, patches, sprays and inhalants. The active ingredient is mixed under sterile conditions with a physiologically acceptable carrier and any preservatives, buffers, or propellants which may be required if necessary.

The compounds of the invention can likewise be used in injectable formulations. Wherein the injection is selected from liquid injection (water injection), sterile powder for injection (powder injection) or tablet for injection (refers to a stamped tablet or a machine pressed tablet prepared by a sterile operation method for medicines), and is dissolved by water for injection when in use for subcutaneous or intramuscular injection.

Wherein the powder for injection contains at least an excipient in addition to the above-mentioned compounds. The excipients described in the present invention, which are components intentionally added to a drug, should not have pharmacological properties in the amounts used, however, the excipients may aid in processing, dissolution or dissolution of the drug, delivery by targeted route of administration, or stability.

The beneficial effects of the invention are as follows:

according to the invention, the potato anthocyanin derivative norsetanin is separated from the black diamond potato for the first time, the structure of the potato anthocyanin derivative norsetanin is determined by utilizing nuclear magnetic resonance, and the effect of the potato anthocyanin derivative norsetanin on inhibiting the activity of tyrosinase is found.

Kojic acid, also known as kojic acid, chemical naming: 5-hydroxy-2- (hydroxymethyl) -4H-pyran-4-one is a tyrosinase inhibitor. Kojic acid is a melanin specific inhibitor, which can complex with copper ions in cells after entering skin cells, change the three-dimensional structure of tyrosinase, prevent the activation of tyrosinase, and thus inhibit the formation of melanin. The novel anthocyanin derivative norsetanin has a higher inhibition effect on tyrosinase activity and is far higher than that of kojic acid.

Drawings

FIG. 1 is a liquid chromatogram of a crude potato extract;

FIG. 2 is a liquid chromatogram of F2;

FIG. 3 is a liquid chromatogram of F2-3;

FIG. 4 is a graph showing the average slope of inhibition of tyrosinase activity by the potato anthocyanin derivative norgestrel;

fig. 5 is a graph showing the comparative effect of the whitening mask of example 2 and comparative example 1.

Detailed Description

The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described herein are only some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.

Example 1

Separation of Potato anthocyanin derivatives method, preparative HPC (Hanbang, chinse:Sup>A) was performed at 535nm and 280nm on se:Sup>A DAC-HB50 separation module in combination with UV detector, and separation was performed using C18-ODS-A (300 mm. Times.50 mm, 5 μm, YMC, japan) and XA quse:Sup>A C18 semi-preparative column (4.6X250 mm, 5 μm, acchrom, chinse:Sup>A).

The method specifically comprises the following steps:

the crude extract of the black diamond potato is segmented by a DAC-HB50 chromatographic column to obtain F1, F2, F3 and F4, the sample concentration is 40mg/ml, the sample injection volume is 20ml, and the mobile phase is 0.6% trifluoroacetic acid water: acetonitrile, elution gradient conditions: 0 to 40min,15 to 35 percent acetonitrile, and the flow rate is 50ml/min, as shown in figure 1, fr.1:25.0 to 26.5min, fr.2:27.0 to 29.0min, fr.3:29.3 to 32.0min, and Fr.4:32.5 to 34.5min.

F2 was finely separated using a Xaqua C18 preparation column (5 um,100A, 20X 250 mm), sample concentration 20mg/ml, sample volume 10ml, mobile phase 0.6% trifluoroacetic acid: acetonitrile, elution gradient conditions of 0-50-55-60min,15% -27.5% -95% -95%, and flow rate of 8ml/min, as shown in figure 2, F2-1-F2-8 are respectively obtained, wherein the retention time of F2-3 is 28.5-31.0 min.

Further purification was performed on F2-3 using a Xaqua C18 column (5 um,100A, 20X 250 mm) with a sample volume of 10ml and a mobile phase of 0.6% trifluoroacetic acid: acetonitrile, elution gradient conditions of 0-40-100min,16% -16% -16%, and flow rate of 8ml/min, as shown in figure 3, retention time of 39.0-45.0 min to obtain compound A, and retention time of 53.5-56.5 min to obtain compound B.

Wherein the crude extract of the black diamond potato is the part of 75% ethanol extract passing through macroporous resin, and specifically comprises the following contents: fresh potato tuber slices (100 kg) were extracted with 75% ethanol and concentrated under reduced pressure to give an extract (1.58 kg) which was eluted sequentially with water, etOH-water (95:5) using D101 macroporous adsorbent resin, and the EtOH-water (95:5) fractions were collected to give a crude potato extract (100.50 g).

EtOH, ethanol.

Compound a was designated norsetanin and has the following structural formula:

the [ M+Na ] test result of the compound A was 833.2117 by mass spectrometry.

Nuclear magnetic resonance data for the potato anthocyanin derivative norsetanin are shown in table 1.

TABLE 1 Nuclear magnetic resonance data for Potato anthocyanin derivatives norsetanin

And confirming the compound A by nuclear magnetic resonance data and searching and comparing:

(2S,3R,4S,5R,6R)-4,5-dihydroxy-2-methyl-6-(((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((7-hydroxy-2-oxo-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydr o-2H-pyran-2-yl)oxy)-2H-chromen-3-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)tetrahy dro-2H-pyran-3-yl(E)-3-(4-hydroxyphenyl)acrylate

example 2

A preparation process of whitening facial mask added with potato anthocyanin derivative norretanin comprises the following steps:

the whitening mask liquid comprises the following raw materials in parts by weight: 12 parts of sodium carboxymethylcellulose, 20 parts of glycerol, 2 parts of norsetanin, 0.3 part of EDTA disodium, 50 parts of deionized water, 1 part of polyoxyethylene castor oil, 3 parts of sodium alginate, 12 parts of centella asiatica extract, 8 parts of purslane extract, 0.4 part of methylparaben and 0.1 part of methylisothiazolinone;

the mask liquid preparation process specifically comprises the following steps:

s1, adding sodium carboxymethyl cellulose into 1/2 deionized water to dissolve to form a colloid solution, then adding glycerol, norsetanin and EDTA disodium into the colloid solution, and stirring until the components are fully dissolved to obtain a phase A component;

s2, adding polyoxyethylene castor oil and sodium alginate into the rest 1/2 deionized water, uniformly stirring to obtain a mixed solution, and sequentially adding centella asiatica extract and purslane extract into the mixed solution, and stirring until the mixed solution is transparent and stable to obtain a phase B component;

s3, uniformly stirring and mixing methyl benzoate and methylisothiazolinone by a mixer to obtain a C-phase component;

and S4, slowly adding the B phase component into the A phase component, heating to 50 ℃ while stirring, preserving heat for 20min, cooling to 30 ℃, adding the C phase component, and continuously stirring until the mixture is stable and transparent, thus obtaining the whitening mask liquid.

The herba Centellae extract and herba Portulacae extract are purchased.

The potato anthocyanin derivative norretannin in the mask disclosed by the invention infiltrates into surface spots, inhibits dark pigment transfer, reduces pigment synthesis, strengthens a barrier, brightens skin color, penetrates into skin, infiltrates into a substrate, blocks melanin transfer, and reduces melanin formation from the source.

Example 3

Inhibition of tyrosinase activity by anthocyanin novel derivative norsetanin:

1) Kit reaction solution preparation

Tyrosinase substrate: dissolving tyrosinase substrate freeze-dried powder with 220 mu L of water;

tyrosinase: dissolving tyrosinase freeze-dried powder in 220 mu L tyrosinase assay buffer solution, subpackaging, and preserving at-20deg.C to avoid repeated freeze-thawing cycle;

tyrosinase enhancer: the protection from light is paid attention to when the product is used, and the product is required to be placed at room temperature when the product is used;

inhibitor control (kojic acid): (1) stock solution: 75 μl of water was added to prepare a 10mM stock solution of kojic acid, and the mixture was homogenized. (2) working solution: to 7.5. Mu.L of the prepared 10mM kojic acid stock solution was added 92.5. Mu.L of water to prepare a 0.75mM kojic acid working solution.

2) Sample measurement

Test samples, inhibitor controls (kojic acid) and blank preparations were prepared.

Adding a sample: mu.L of the Sample to be tested (Sample, S), kojic acid control (IC) or tyrosinase assay buffer (EC) were added to the 96-well plates, respectively. The 96-well plate, namely the 96-well cell culture plate and dish series products are manufactured by using imported optically transparent pure polystyrene. The method is characterized in that the method is prepared by adopting a special process, so that cells reach an optimal adsorption state, and all products are sterilized by gamma rays.

Adding tyrosinase solution: 50 mu L of tyrosinase enzyme solution is taken from each hole, 2 mu L of tyrosinase enzyme is used as tyrosinase enzyme assay buffer solution, and the mixture is uniformly mixed and then incubated for 10 minutes at 25 ℃.

Tyrosinase substrate addition: 30 mu L of tyrosinase substrate solution, 23 mu L of tyrosinase assay buffer, 2 mu L of tyrosinase substrate and 5 mu L of tyrosinase enhancer are taken from each hole and uniformly mixed.

Measurement: absorbance at 510nm was measured at 30 and 55 minutes in kinetic mode, yielding corresponding absorbance values (Abs 1, abs 2).

3) And (3) calculating results: the slope of all samples, including enzyme activity control (EC, buffer group), was calculated and relative inhibition was calculated by dividing net value Δabs of (Abs 2-Abs 1) by time Δt (T2-T1), and the sample slope plot is shown in fig. 1.

Tyrosinase inhibitory activity of anthocyanin new derivative norsetanin was calculated from relative inhibition% = [ slope (EC) -slope (S) ]/slope (EC) ×100) as shown in table 3:

TABLE 3 tyrosinase inhibitory activity

As shown in Table 1, the novel anthocyanin derivative norsetanin has a higher inhibition effect on tyrosinase activity and is far higher than that of kojic acid.

Comparative example 1

A preparation process of whitening facial mask added with nicotinamide comprises the following steps:

the whitening mask liquid comprises the following raw materials in parts by weight: 12 parts of sodium carboxymethyl cellulose, 20 parts of glycerin, 2 parts of nicotinamide, 0.3 part of EDTA disodium, 50 parts of deionized water, 1 part of polyoxyethylene castor oil, 3 parts of sodium alginate, 12 parts of centella asiatica extract, 8 parts of purslane extract, 0.4 part of methylparaben and 0.1 part of methylisothiazolinone;

the mask liquid preparation process specifically comprises the following steps:

s1, adding sodium carboxymethyl cellulose into 1/2 deionized water to dissolve to form a colloid solution, then adding glycerol, nicotinamide and EDTA disodium into the colloid solution, and stirring until the components are fully dissolved to obtain a phase A component;

Two groups of testers, 50 persons each, were selected, and each of the face masks prepared in example 3 and comparative example 1 was applied after cleansing, kept clean after 20 minutes, and tested continuously for 30 days 1 time a day, and the statistical whitening effect was plotted as shown in fig. 5.

As shown in fig. 5, the effect of the nicotinamide is to reduce the generation of melanocyte to achieve the effect of whitening and lightening spots, and the effect of the nicotinamide is obvious in comparative example 1; the mask added with the potato anthocyanin derivative norsetanin is found to be similar to the whitening effect of a nicotinamide mask in 7 days, 21 days and 28 days of test results.

Claims

1. A compound of formula I norsetanin or its individual optical isomers, crystalline forms, pharmaceutically acceptable salts, hydrates or solvates thereof:

2. the preparation method of the black diamond potato extract is characterized by comprising the following steps:

3. The extract of claim 2, wherein the nonpolar macroporous resin is selected from the group consisting of HPD-100, HPD-300, d-101, x-5, H103; the macroporous resin with weak polarity is selected from AB-8, DA-201 and HPD-400.

4. The extract of claim 2, wherein the concentration of trifluoroacetic acid in water is 0.6%.

5. Use of a compound of formula i as defined in claim 1 or of individual optical isomers, individual crystalline forms, pharmaceutically acceptable salts, hydrates or solvates thereof, or of an extract as defined in any of claims 2 to 4, for the preparation of a product for inhibiting tyrosinase activity.

6. The use according to claim 5, wherein the product is a melanin inhibiting product.

7. The use according to claim 5, wherein the product is a product with whitening and freckle removing functions.

8. Use according to any one of claims 5 to 7, wherein the product is a pharmaceutical product, a cosmetic product.

9. Whitening product, characterized in that its active ingredient comprises at least norsetanin according to claim 1 or an extract according to any one of claims 2 to 4.

10. The whitening product according to claim 9, wherein the product is selected from the group consisting of a mask, a cream, an emulsion, a toner, a facial cleanser.