A composition of a compound containing a fluorene or fluorenone backbone

Abstract

The present application relates to a kind of compositions of compound containing fluorene or fluorenone skeleton, specifically, the present application discloses a kind of composition, it includes as shown in formula II compound or its pharmaceutically acceptable salt: the compound provided by the present application can be as tyrosinase inhibitor, with excellent whitening, anti-oxidation, ultraviolet absorption effect, and compared with traditional resorcinol structure has better water solubility, lower cytotoxicity, provides the train of thought for the future whitening efficacy compound design screening.

Description

Technical Field

[0001] This invention relates to a composition of a compound containing a fluorene or fluorene ketone skeleton. Background Technology

[0002] Skin color is primarily determined by the number of melanocytes in the epidermis and the rate of melanin synthesis. Melanin formation involves a series of complex physiological and biochemical processes. Currently developed skin-whitening and spot-removing products mainly achieve their whitening effect by inhibiting tyrosinase, thereby suppressing melanin production. Commonly used skin-whitening substances include hydroquinone, hexadecene-1,16-dicarboxylic acid, kojic acid and its derivatives, niacinamide, arbutin, ascorbic acid and its derivatives, flavonoids, ellagic acid and its derivatives, tranexamic acid and various resorcinol derivatives, 4-n-butylresorcinol, 4-n-hexylresorcinol, and 4-(1-phenylethyl)benzene-1,3-diol. However, prolonged use of hydroquinone can lead to irreversible changes in the skin's pigment system, causing cytotoxicity to melanocytes and posing a risk of permanent skin depigmentation. China has banned the addition of hydroquinone to skincare products and it can only be used with a prescription. Kojic acid has the defects of sensitization and cell mutation; nicotinamide and its analogues have the defects of teratogenicity and intolerance in some people; arbutin has the defects of high concentration dependence. While existing resorcinol derivatives can well embed into the double copper active pocket of tyrosinase to exert enzyme inhibition, the main representative small molecules include 377 (phenylethyl resorcinol), peptidamine, and glycyrrhizin, etc., they still have certain problems such as insufficient inhibitory activity against human tyrosinase, unstable physicochemical properties, skin irritation, and incompatibility with sensitive skin, which cannot meet the needs of patients with pigmentation.

[0003] Tyrosinase, a key target in multiple fields, participates not only in skin melanin production but also in neuromelanin production. This enzyme catalyzes the oxidation of dopa to dopaquinone, mediating neuromelanin synthesis. Overexpression of tyrosinase induces oxidative stress and neuronal death, directly linked to the progression of neurodegenerative diseases such as Parkinson's and Huntington's. In agriculture and food, inhibiting browning in fruits and vegetables (blocking phenolic oxidation and polymerization) significantly extends shelf life, while also enabling the development of green biological pesticides targeting the melanosis pathway in insect epidermis. In the cosmetics field, inhibiting melanin production achieves whitening, spot-fading, and anti-photoaging effects. This "one target, multiple treatments" characteristic stems from the broad spectrum (monophenols / diphenols / catechins) and cross-species conservation of tyrosinase substrates. Current research focuses on the design of dual-function molecules (such as integrating antioxidant and inhibitory activities) and the development of nanodelivery systems to synergistically advance its industrial applications in disease intervention, agricultural product preservation, environmentally friendly pesticides, and functional skincare products. Summary of the Invention

[0004] The technical problem to be solved by this invention is to overcome the defects of existing resorcinol, which can cause skin irritation and potential health risks. This invention provides a small molecule skeleton structure with a fluorene or fluorenone skeleton. The compound provided by this invention can be used as a tyrosinase inhibitor, with excellent whitening, antioxidant and ultraviolet absorption effects. Compared with the traditional resorcinol structure, it has better water solubility and lower cytotoxicity, providing ideas for the design and screening of future whitening compounds.

[0005] The present invention solves the above-mentioned technical problems through the following technical solution: The present invention also provides a composition comprising a compound as shown in Formula II or a pharmaceutically acceptable salt thereof: said composition is a cosmetic composition, a skin care composition or a pharmaceutical composition; ; Among them, R 3 and R 4 Independently hydroxyl or C 1-3 alkyl; A is either CR1R2 or CO; R 1 and R 2 Independently H or C 1-10 alkyl; x is 0, 1, 2, 3, 4 or 5; y can be 0, 1, 2, 3, 4 or 5.

[0006] In some implementation schemes, there are 0, 1, or 2 Rs. 3 It is a hydroxyl group; for example, it has 0 or 1 R. 3 It is a hydroxyl group.

[0007] In some implementation schemes, there are 0, 1, or 2 Rs. 4 It is a hydroxyl group; for example, it has 0 or 1 R. 4 It is a hydroxyl group.

[0008] In some implementation schemes, R 3 and R 4 It contains one or two hydroxyl groups.

[0009] In some implementation schemes, R 3 and R 4 Independently hydroxyl or methyl; for example, hydroxyl.

[0010] In some implementations, x is 0 or 1.

[0011] In some implementations, y is 0 or 1.

[0012] In some implementation schemes, R 1 and R 2 Independently H or C1-10 Straight-chain alkyl or C 1-10 Single-branched alkyl group.

[0013] In some implementation schemes, R 1 and R 2 Independently H or C 1-3 alkyl.

[0014] In some implementation schemes, R 1 and R 2 It can be H or methyl on its own.

[0015] In some implementation schemes, R 1 and R 2 H stands for H independently.

[0016] In some embodiments, the compound shown in Formula II is , , , , , , , or .

[0017] In some embodiments, the compound of formula II or a pharmaceutically acceptable salt thereof in the cosmetic composition or skin care composition has one or more of the following effects: (1) whitening effect; (2) antioxidant effect; (3) ultraviolet absorption effect.

[0018] In some embodiments, the compound of formula II or a pharmaceutically acceptable salt thereof in the composition acts to prevent melanin deposition or pigmentation in the skin.

[0019] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole whitening active ingredient in the cosmetic or skincare composition.

[0020] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole antioxidant active ingredient in the cosmetic or skincare composition.

[0021] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole UV-absorbing active ingredient in the cosmetic or skincare composition.

[0022] In some embodiments, the weight of the compound of Formula II or a pharmaceutically acceptable salt thereof accounts for 0.000005%-20% of the total weight of the composition.

[0023] In some embodiments, the pharmaceutical composition further includes pharmaceutically acceptable excipients.

[0024] In some embodiments, the cosmetic composition further includes cosmetically acceptable excipients; In some embodiments, the skincare composition further includes skincare-acceptable excipients.

[0025] The pharmaceutically acceptable excipients are conventional excipients for this type of composition in the art.

[0026] The cosmetically acceptable excipients are conventional excipients for this type of composition in the art.

[0027] The skincare-grade, scientifically acceptable excipients are conventional excipients for this type of composition in the art.

[0028] In some embodiments, the pharmaceutical composition is selected from one or more of creams, gels, patches, sprays, ointments, plasters, emulsions, liniments, pastes, or mud dressings.

[0029] In some embodiments, the cosmetic composition is selected from one or more of toners, foundations, pressed powders, concealers, BB creams, eyeshadows, lipsticks, lip balms, mascaras, eyebrow pencils, eyelid removers, or makeup removers.

[0030] In some embodiments, the skin care composition is selected from one or more of the following: toner, lotion, massage cream, nourishing cream, moisturizing cream, hand cream, serum, face mask, soap, facial cleanser, cleansing milk, cleansing cream, body lotion, shampoo, or shower gel.

[0031] The present invention also provides the use of the compound shown in Formula II in the preparation of a composition; said composition is a cosmetic composition, a skin care composition, or a pharmaceutical composition; ; The compounds shown in Formula II are defined as described in any embodiment of this application.

[0032] In some embodiments, the cosmetic composition or skin care composition has one or more of the following effects: (1) whitening effect; (2) antioxidant effect; (3) ultraviolet absorption effect.

[0033] In some implementations, the cosmetic, skin care product, or drug serves to prevent melanin deposition or pigmentation in the skin.

[0034] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole whitening active ingredient in the cosmetic or skincare composition.

[0035] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole antioxidant active ingredient in the cosmetic or skincare composition.

[0036] In some embodiments, the compound of Formula II or its pharmaceutically acceptable salt is the sole UV-absorbing active ingredient in the cosmetic or skincare composition.

[0037] In some embodiments, the weight of the compound of formula II or its pharmaceutically acceptable salt in the cosmetic or skincare composition accounts for 0.000005%-20% of the total weight of the drug, cosmetic or skincare product.

[0038] In some embodiments, the pharmaceutical composition is selected from one or more of creams, gels, patches, sprays, ointments, plasters, emulsions, liniments, pastes, or mud dressings.

[0039] In some embodiments, the cosmetic composition is selected from one or more of toners, foundations, pressed powders, concealers, BB creams, eyeshadows, lipsticks, lip balms, mascaras, eyebrow pencils, eyelid removers, or makeup removers.

[0040] In some embodiments, the skin care composition is selected from one or more of the following: toner, lotion, massage cream, nourishing cream, moisturizing cream, hand cream, serum, face mask, soap, facial cleanser, cleansing milk, cleansing cream, body lotion, shampoo, or shower gel.

[0041] The compositions of the present invention can be prepared, depending on the specific dosage form, using appropriate excipients, and by any suitable method known in the art.

[0042] In this invention, the term "skincare product" refers to a product applied to the surface of human skin by smearing, spraying or other similar methods, with the main purpose of exerting physiological care effects such as moisturizing, repairing, anti-wrinkle, whitening, soothing and sun protection, and which maintains or improves the health of the skin by acting on the stratum corneum or deep tissues of the skin.

[0043] In this invention, the term "cosmetics" refers to products applied to any part of the human body surface (including skin, hair, nails, lips, etc.) by smearing, spraying or other similar methods, with the primary purpose of cleaning, adding fragrance, changing appearance, correcting blemishes, covering or coloring, and characterized by immediate visual effects or sensory experiences.

[0044] The positive and progressive effects of this invention are that the compounds provided by this invention have one or more of the following effects: 1) It has excellent whitening or melanin deposition prevention effects. It has a good inhibitory effect on mouse melanocyte B16F10 and mushroom tyrosinase.

[0045] 2) It has excellent oxygen free radical scavenging function. When applied in cosmetics, it can effectively block the skin stress response caused by oxygen free radicals and prevent photoaging.

[0046] 3) It has excellent UV absorption function, and its UV absorption effect is significantly better than that of 377.

[0047] 4) It has better water solubility compared to the traditional resorcinol structure.

[0048] 5) It has high stability.

[0049] 6) It has lower cytotoxicity than traditional resorcinol structures (such as 377 and Peptide Amide).

[0050] 7) The structure is simple, readily available, and the cost is controllable. Attached Figure Description

[0051] Figure 1 The images show the UV-Vis absorption spectra of the compounds of this invention and Comparative Example 377. Detailed Implementation

[0052] The present invention will be further illustrated by way of embodiments below, but the present invention is not limited to the scope of the embodiments described herein.

[0053] The present invention can be implemented through the following embodiments, but the present invention is not limited thereto.

[0054] Unless otherwise specified, all percentages mentioned in the embodiments of this invention are weight percentages.

[0055] The instruments and equipment used in the embodiments of the present invention are all conventional instruments and equipment in the field and can be replaced by instruments and equipment that conform to the corresponding standards.

[0056] Unless otherwise specified, all active pharmaceutical ingredients and reagents used in the embodiments of this invention are commercially available analytical grade reagents. Small molecule structures with fluorene or fluorenone skeletons were obtained from Shanghai Bide Pharmaceutical Technology Co., Ltd. or Shanghai Adamas Reagent Co., Ltd.

[0057] Mushroom tyrosinase, obtained from Sigma-Aldrich Corporation, USA.

[0058] L-DOPA is obtained from Sigma-Aldrich Corporation in the United States.

[0059] DPPH was acquired from Sigma-Aldrich Corporation in the United States.

[0060] A mouse B16F10 cell melanin inhibition model was obtained from the Cell Bank of the Chinese Academy of Sciences. Example 1: Mushroom Tyrosinase Inhibition Experiment Solution preparation 80 mM Phosphate Buffer (PB): 1) Dissolve 9.60 g NaH2PO4 in 1 L of deionized water; 2) Dissolve 11.36 g Na2HPO4 in 1 L of deionized water; 3) Add 2) to 1) until the pH is 6.8; 1 M hydrochloric acid: Add 1 mL of concentrated hydrochloric acid to 11 mL of deionized water; 6.0 mM L-DOPA solution: Dissolve 7.1 mg L-DOPA in 100 μL of 1 M hydrochloric acid, and add 80 mM PB to a final volume of 6 mL; 250 U / mL Tyrosinase: 25 KU tyrosinase solid dissolved in 1 mL 80 mM PB, dispensed in 40 μL tubes, and replenished to 4 mL with PB before use; Experimental steps Dissolve the sample powder in PB to prepare a 100 μg / ml solution, then dilute with PB to obtain solutions with concentrations of 50 μg / ml, 25 μg / ml, 12.5 μg / ml, 6.25 μg / ml, 3.125 μg / ml, and 1.5625 μg / ml (the concentration gradient may be different for different samples; prepare the concentration as needed).

[0061] Positive control: Peptidylamine powder was also dissolved in PB to prepare a 100 μg / ml solution, which was then diluted with PB to obtain solutions with concentrations of 50 μg / ml, 25 μg / ml, 12.5 μg / ml, 6.25 μg / ml, 3.125 μg / ml, and 1.5625 μg / ml.

[0062] In a 96-well plate, sample group As was treated with 50 μL PB, 20 μL sample, and 50 μL of prepared tyrosinase solution. Blank group Asb was treated with 50 μL PB, 20 μL sample, and 50 μL tyrosinase solution. Blank group Acb was treated with 70 μL PB and 50 μL tyrosinase solution. Control group Ac was treated with 70 μL PB and 50 μL tyrosinase solution and incubated at room temperature in the dark for 10 min. Then, sample group As and control group Ac were treated with 50 μL L-DOPA solution, and blank groups Asb and Acb were treated with 50 μL PB and incubated at room temperature in the dark for 15 min. The absorbance at 475 nm was measured using a microplate reader.

[0063] The formula for calculating the tyrosinase inhibition rate is as follows: Tyrosinase inhibition rate % = [ 1 - ( As - Asb ) / (Ac-Acb) ] × 100%.

[0064] Where As represents the sample group, Asb represents the blank group, Ac represents the control group, and Acb represents the blank group.

[0065] The results are shown in Table 1: Table 1: Mushroom Tyrosinase Inhibition Experiment

[0066] Test results show that this series of small molecule compounds with fluorene or fluorenone skeletons have excellent whitening effects, and can achieve whitening and prevent melanin deposition by inhibiting tyrosinase.

[0067] Example 2: DPPH Oxygen Free Radical Scavenging Experiment

[0068] DPPH working solution preparation

[0069] Dissolve an appropriate amount of DPPH solid in anhydrous ethanol until the absorbance at 517 nm is 1.6 ± 0.01 (take 200 μL and detect in a 96-well plate).

[0070] Experimental steps

[0071] Positive control: Peptidylamine powder was dissolved in anhydrous ethanol to prepare a solution with a concentration of 50 μg / ml. The solution was then diluted with anhydrous ethanol to obtain solutions with concentrations of 25 μg / ml, 12.5 μg / ml, 6.25 μg / ml, 3.125 μg / ml, 1.5625 μg / ml, and 0.78125 μg / ml.

[0072] Similarly, the sample powder was dissolved in anhydrous ethanol to prepare a solution with a concentration of 50 μg / ml. The solution was then diluted with anhydrous ethanol to obtain solutions with concentrations of 25 μg / ml, 12.5 μg / ml, 6.25 μg / ml, 3.125 μg / ml, 1.5625 μg / ml, and 0.78125 μg / ml (the concentration gradient may be different for different samples, and the concentration should be prepared as needed).

[0073] In a 96-well plate, sample group As was added with 100 μL of sample solution and 100 μL of DPPH. Blank group Asb was added with 100 μL of sample solution and 100 μL of anhydrous ethanol. Control group Ac was added with 100 μL of anhydrous ethanol and 100 μL of DPPH solution, and blank group Acb was added with 200 μL of anhydrous ethanol. The plates were reacted at room temperature for 30 min, and the absorbance at 517 nm was measured using a microplate reader.

[0074] The formula for calculating the DPPH inhibition rate (%) is as follows: DPPH inhibition rate % = [ 1 - ( As - Asb ) / (Ac - Acb) ] × 100% Wherein, As represents the sample group, Asb represents the blank group, Ac represents the control group, and Acb represents the blank group.

[0075] The test results are shown in Table 2: Table 2: DPPH Oxygen Free Radical Scavenging Experiment

[0076] Test results show that this series of small molecule compounds with fluorene or fluorenone skeletons have excellent DPPH oxygen free radical scavenging effect. By scavenging oxygen free radicals, they achieve a good antioxidant effect, effectively prevent skin irritation caused by oxygen free radicals, and play a role in skin protection.

[0077] Example 3: B16F10 mouse melanocyte cytotoxicity experiment

[0078] Mouse melanocyte B16F10 cell line was used for testing. Cells were seeded in 96-well plates with 1640++ culture medium at a density of 1×10⁻⁶ cells / well. 4Cells / well, 100 μL per well, incubated overnight at 37 ℃ (5% CO2 concentration). After 24 h, the original culture medium was aspirated and washed 1-2 times with PBS buffer. Samples were prepared using phenol red-free DMEM medium, including 377 and Peptidyl ether at concentrations of 10 μg / ml, 5 μg / ml, 2.5 μg / ml, 1.25 μg / ml, 0.625 μg / ml, and 0.3125 μg / ml as positive controls, the culture medium as a blank control, and sample solutions at concentrations of 50 μg / ml, 25 μg / ml, 12.5 μg / ml, 6.25 μg / ml, 3.125 μg / ml, and 1.5625 μg / ml (the concentration gradient may vary for different samples; prepare concentrations as needed). 100 μL was added to each well of a 96-well plate, for a total of 100 μL / well. Incubate at 37 ℃ for 24 h (5% CO2 concentration), then aspirate the original culture medium and sample solution, and wash 1-2 times with PBS buffer. Add 100 μL of DMEM-prepared cck8 solution, for a total of 100 μL / well, and incubate at 37 ℃ in the dark for 1 h (5% CO2 concentration). Measure the absorbance at 450 nm using a microplate reader.

[0079] The test results are shown in Table 3: Table 3: Cytotoxicity assay of B16F10 mouse melanocytes

[0080] Test results show that this series of small molecule compounds with fluorene or fluorenone skeletons have lower cytotoxicity than 377 and Peptamin Mido, which may reduce skin irritation. They are less toxic and milder active ingredients than 377 and Peptamin Mido.

[0081] Example 4: B16F10 mouse melanocyte inhibition experiment

[0082] Mouse melanocyte B16F10 cell line was used for testing. Cells were seeded in 96-well plates with 1640++ culture medium at a density of 1×10⁻⁶ cells / well. 4100 μL per well, cells / well, incubated overnight at 37 °C (5% CO2 concentration). After 24 hours, the original culture medium was aspirated, and the sample was washed 1-2 times with PBS buffer. A solution of α-MSH (Shanghai Mairui Biochemical Technology Co., Ltd.) prepared with phenol red-free DMEM medium was added to a final concentration of 1 μM, 100 μL per well. Samples were then prepared using phenol red-free DMEM medium, including positive controls of peptide-aminomethylpyridinium chloride at concentrations of 1000 ng / ml, 500 ng / ml, 250 ng / ml, 125 ng / ml, and 62.5 ng / ml, and a blank control of the culture medium. Sample solutions at concentrations of 1000 ng / ml, 500 ng / ml, 250 ng / ml, 125 ng / ml, and 62.5 ng / ml (the concentration gradient may vary for different samples; prepare the concentration as needed) were added to 96-well plates, 100 μL per well, for a total of 200 μL / well. The culture was carried out in a constant temperature incubator at 37 ℃ for 72 h (5% CO2 concentration). 100 μL of the supernatant was taken per well and transferred to a new 96-well plate. The absorbance was measured at 405 nm using a microplate reader.

[0083] The results are shown in Table 4: Table 4: Melanocyte Inhibition Experiment in B16F10 Mice

[0084] Test results show that this series of small molecule compounds has excellent whitening effects, and can achieve whitening and prevent melanin deposition by inhibiting melanocytes from producing melanin.

[0085] Example 5: Solubility test of the compound

[0086] The aforementioned series of small molecule compounds with fluorene or fluorenone skeletons exhibit good solubility in alcohols. Therefore, the test solutions were water and ethanol-water solutions of different volume ratios. Test method: 1 mg of the compound was weighed into an EP tube, 10 μL of ethanol was added, and the solution was sonicated for 3 min. The resulting solution was recorded as having 100% ethanol content. Subsequently, 10 μL, 30 μL, 50 μL, 100 μL, and 800 μL of deionized water were added sequentially to the EP tube. After each addition, the solution was sonicated for 3 min, and the resulting solution was recorded as having 50%, 20%, 10%, 5%, and 1% ethanol content. The results are shown in Table 5. Table 5: Solubility test results of compounds

[0087] The results showed that the solubility of this series of small molecule compounds was improved compared to 377, which can effectively improve the water solubility of whitening small molecules.

[0088] Example 6: Stability test of the compound

[0089] The stability of a series of small molecule compounds with fluorene or fluorenone skeletons in ethanol-water solutions was tested. 10 mg of the corresponding sample (purity greater than 97%) was weighed into EP tubes, 200 μL of dipropylene glycol was added, and the mixture was sonicated until completely dissolved. Then, 800 μL of deionized water was added to prepare an ethanol-water solution with a sample concentration of 1%. The EP tubes were sealed and placed in an oven at 48±2℃ for 4 weeks. The change in sample purity was examined by HPLC. The test results are shown in Table 6. Table 6: Stability test results of the compounds

[0090] The results show that the compound obtained in this application remains stable at high temperatures for a long time, exhibiting excellent thermal stability.

[0091] Example 7: Ultraviolet absorption efficacy test of the compound

[0092] The compound was dissolved in DMSO and then diluted with ethanol to prepare a 2 ppm solution. The absorption spectrum in the 250-400 nm range was analyzed using a UV-Vis spectrometer. The results are as follows: Figure 1 As shown.

[0093] The results showed that the test samples exhibited good ultraviolet absorption in both the UVA and UVB regions, and at the same concentration of 2 ppm, the absorbance of the series of compounds of this invention was much greater than 377, especially compound ZY01DF18. This indicates that the series of small molecule compounds with fluorene or fluorenone skeletons proposed in this invention can reduce photoaging damage to the skin by absorbing ultraviolet light.

[0094] While specific embodiments of the present invention have been described above, those skilled in the art should understand that these are merely illustrative examples, and the scope of protection of the present invention is defined by the appended claims. Those skilled in the art can make various changes or modifications to these embodiments without departing from the principles and essence of the present invention, but all such changes and modifications fall within the scope of protection of the present invention.

Claims

1. The use of a compound of formula II in the preparation of a cosmetic composition; characterized in that, A is CR 1 R 2 or CO;R 1 and R 2 For H; R 3 and R 4 For hydroxyl group; R 3 and R 4 The composition contains one or two hydroxyl groups; x is 0 or 1; y is 0 or 1; the cosmetic composition has one or more of the following effects: (1) whitening effect; (2) ultraviolet absorption effect.

2. The application as described in claim 1, characterized in that, The cosmetic composition helps prevent melanin deposition in the skin.

3. The application as described in claim 1, characterized in that, It meets one or more of the following conditions: (1) In the cosmetic composition, the compound as shown in Formula II or its pharmaceutically acceptable salt is the sole whitening active ingredient; (2) In the cosmetic composition, the compound of formula II or its pharmaceutically acceptable salt is the only ultraviolet-absorbing active ingredient; (3) In the cosmetic composition, the weight of the compound as shown in Formula II or its pharmaceutically acceptable salt accounts for 0.000005%-20% of the total weight of the cosmetic composition; (4) The cosmetic composition is selected from one or more of the following: lotion, foundation, powder, concealer, BB cream, lipstick, eyebrow pencil, eyelid makeup remover, and makeup remover; (5) The cosmetic composition also includes cosmetically acceptable excipients.

4. The application as described in claim 1, characterized in that, The cosmetic composition is selected from one or more of eyeshadow, lipstick and mascara.

5. The use of a compound of formula II in the preparation of a skin care composition; characterized in that, A is CR 1 R 2 or CO;R 1 and R 2 For H; R 3 and R 4 For hydroxyl group; R 3 and R 4 There is one or two hydroxyl groups in the composition; x is 0 or 1; y is 0 or 1; the skin care composition has one or more of the following effects: (1) whitening effect; (2) ultraviolet absorption effect.

6. The application as described in claim 5, characterized in that, The skincare composition helps prevent melanin deposition in the skin.

7. The application as described in claim 6, characterized in that, It meets one or more of the following conditions: (1) In the skin care composition, the compound as shown in Formula II or its pharmaceutically acceptable salt is the only whitening active ingredient; (2) In the skin care composition, the compound as shown in Formula II or its pharmaceutically acceptable salt is the only ultraviolet-absorbing active ingredient; (3) In the skin care composition, the weight of the compound as shown in Formula II or its pharmaceutically acceptable salt accounts for 0.000005%-20% of the total weight of the skin care composition; (4) The skin care product composition is selected from one or more of the following: toner, lotion, massage cream, nourishing cream, moisturizing cream, serum, facial mask, soap, facial cleanser, cleansing cream, shampoo and shower gel; (5) The skin care composition also includes skin care science acceptable excipients.

8. The application as described in claim 6, characterized in that, The skin care composition is selected from one or more of hand creams, facial cleansers, and body lotions.

9. The use of a compound of formula II in the preparation of a pharmaceutical composition; characterized in that, A is CR 1 R 2 or CO;R 1 and R 2 For H; R 3 and R 4 For hydroxyl group; R 3 and R 4 The composition contains one or two hydroxyl groups; x is 0 or 1; y is 0 or 1; the pharmaceutical composition has one or more of the following effects: (1) whitening effect; (2) ultraviolet absorption effect.

10. The application as described in claim 9, characterized in that, The pharmaceutical composition has the effect of preventing melanin deposition in the skin.

11. The application as described in claim 9, characterized in that, It meets one or more of the following conditions: (1) In the pharmaceutical composition, the weight of the compound as shown in Formula II or a pharmaceutically acceptable salt thereof accounts for 0.000005%-20% of the total weight of the pharmaceutical composition; (2) The pharmaceutical composition is selected from one or more of creams, gels, patches, sprays, ointments, plasters, emulsions, liniments, pastes or mud dressings; (3) The pharmaceutical composition further includes pharmaceutically acceptable excipients.

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