A class of wangbaisiyang glycosides and application thereof

Abstract

The application discloses a kind of Wang Baihe glycosides compound and application thereof, wherein Wang Baihe glycosides compound is any one of compound I, compound II, compound III, which is a new chemical component found in lily.The application carries out structural identification to the compound separated by the above method by chromatography, modern spectroscopy and the like means.The application also carries out cell proliferation experiment using mouse embryonic fibroblast NIH-3T3, and finds that the compound has the function of promoting skin cell proliferation, and can be used in skin protection and repair field.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of medicine, in particular to a kind of regaloside compound and application thereof. BACKGROUND

[0002] Lily is an important ornamental plant, and regaloside is a unique important active ingredient in lily, which is a general term for phenylpropanoyl glycerol glucoside substances (Zhou et al., 2021). Currently, researchers have detected 13 types of regaloside from lily plants. Studies have shown that regaloside has antioxidant, antibacterial, anti-inflammatory, and delaying type II diabetes, protecting myocardial cells, and other functions (Luo et al., 2012; Murray et al., 2019; Kim et al., 2020). However, whether there are different types of regaloside compounds in lily and the potential functions of these compounds are unknown. SUMMARY

[0003] In view of the above deficiencies in the prior art, the purpose of the present application is to provide a type of regaloside compound and its application in the preparation of skin repair and protection drugs and cosmetics.

[0004] To achieve the above-mentioned purposes, the technical scheme adopted by the present application is as follows:

[0005] In a first aspect, a type of regaloside compound is provided, which is any one of compound I, compound II, and compound III. The structural formula is as follows:

[0006]

[0007] Compound I

[0008]

[0009] Compound II

[0010]

[0011] Compound III

[0012] In a second aspect, a preparation method of the regaloside compound is provided, which includes the following steps:

[0013] 1) The lily plant is crushed, extracted, and concentrated under reduced pressure to obtain a concentrated solution;

[0014] 2) The concentrated solution is extracted with an equal volume of ethyl acetate multiple times to obtain an ethyl acetate phase and an aqueous phase, respectively;

[0015] 3) The ethyl acetate phase and the water phase are concentrated respectively, then mixed with 60-80 mesh silica gel, and dried by blowing air;

[0016] 4) The 200-300 mesh silica gel is used as the filler, petroleum ether-ethyl acetate is used as the mobile phase, petroleum ether: ethyl acetate = 50:1-0:1, and the sample is eluted and segmented;

[0017] 5) After the segmented eluent is developed by point plate development with petroleum ether-ethyl acetate as the developing agent, 10% sulfuric acid ethanol is used for coloration, a plurality of crude extracts are obtained, and after HPLC analysis, the peak graph near the retention time of the standard substance of Wangbili glycoside A and Wangbili glycoside B is compared, and the segments 6-10 are taken as the crude preparation;

[0018] 6) The crude preparation is further prepared by C 18 18 column, methanol: 0.1% phosphoric acid water = 40:60 as the mobile phase elution, and detected at 310 nm, and the crude fraction is further divided into 10 segments Fr1-Fr10, and then further prepared by acetonitrile: 0.1% phosphoric acid water = 10:90-20:80, and the acetonitrile: 0.1% phosphoric acid water = 35:65 is used for column segment;

[0019] 7) The acetonitrile-0.1% phosphoric acid water or tetrahydrofuran-0.1% phosphoric acid water is repeatedly prepared and purified, and different monomers are obtained after evaporation under reduced pressure.

[0020] Further, the method of step 1) is specifically: the lily plant is crushed and then put into a low-pressure chromatography column, 70% methanol is used for percolation extraction for 4 times, each time for 24 h, the combined filtrate is filtered to obtain the extract, and the filtrate is concentrated under reduced pressure at 60 DEG C until there is no alcohol, and a concentrated solution is obtained.

[0021] Further, in step 7), Fr3 is prepared by HPLC, acetonitrile: 0.1% phosphoric acid water = 15:85, Fr3-1 is obtained, and then tetrahydrofuran: 0.1% phosphoric acid water (ρ=0.985) is used for preparation, and compound I (94.36%) is obtained at 7.0'; Fr7 is prepared by HPLC, acetonitrile: 0.1% phosphoric acid water = 18:82, and compound II (97.91%) is obtained at 7.9'; Fr9 is prepared by HPLC, methanol: 0.1% phosphoric acid water = 20:80, and compound III (98.07%) is obtained at 10.5'.

[0022] In a third aspect, the application provides a kind of Wangbili glycoside compound or its pharmaceutically acceptable salt, solvate, tautomer, stereoisomer, prodrug molecule, metabolite in the application of skin repair and protection drug and cosmetic.

[0023] The beneficial effects of the application are:

[0024] The application discloses a new type of lilyturfoside compound, which is a new chemical component found in lily. The application identifies the structure of the compound separated by the above method through chromatography, modern spectroscopy and the like. The application also finds that the compound has the function of promoting skin cell proliferation by using mouse embryo fibroblast NIH-3T3 to carry out cell proliferation experiment, and can be used in the field of skin protection and repair. BRIEF DESCRIPTION OF DRAWINGS

[0025] Figure 1 is a structural formula (a) and main HMBC (b) of compound I;

[0026] Figure 2 is a structural formula (a) and main HMBC (b) of compound II;

[0027] Figure 3 is a structural formula (a) and main HMBC (b) of compound III;

[0028] Figure 4 is a chromatogram of compound I;

[0029] Figure 5 is a chromatogram of compound II;

[0030] Figure 6 is a chromatogram of compound III;

[0031] Figure 7 is an ESI-MS spectrum of compound I;

[0032] Figure 8 is an ESI-MS spectrum of compound II;

[0033] Figure 9 is an ESI-MS spectrum of compound III;

[0034] Figure 10 is a H-NMR spectrum of compound I; 1

[0035] Figure 11 is a H-NMR spectrum of compound II; 1

[0036] Figure 12 is a H-NMR spectrum of compound III; 1

[0037] Figure 13 is a C-NMR spectrum of compound I; 13

[0038] Figure 14 is a C-NMR spectrum of compound II; 13

[0039] ​​​​​Figure 15 HSQC spectrum of compound I; 13 C-NMR spectrum;

[0040] Figure 16 HSQC spectrum of compound I;

[0041] Figure 17 HSQC spectrum of compound II;

[0042] Figure 18 HSQC spectrum of compound III;

[0043] Figure 19 HMBC spectrum of compound I;

[0044] Figure 20 HMBC spectrum of compound II;

[0045] Figure 21 HMBC spectrum of compound III;

[0046] Figure 22 Effect of compound I on the proliferation of mouse embryonic fibroblast NIH-3T3 cells;

[0047] Figure 23 Effect of compound II on the proliferation of mouse embryonic fibroblast NIH-3T3 cells;

[0048] Figure 24 Effect of compound III on the proliferation of mouse embryonic fibroblast NIH-3T3 cells. DETAILED DESCRIPTION

[0049] Example 1: Preparation of compounds

[0050] The following will be described in detail with the raw material of dried lily bulb scales of Lilium lancifolium Thunb.

[0051] It is particularly pointed out that the present embodiment is described only by taking the lily bulb scales of Lilium lancifolium Thunb. as an example. Since the lily bulb scales and other parts (such as flowers, leaves, stems, roots, bulbils, etc.) of plants of the genus Lilium contain liliunin components, it is obvious for those skilled in the art to make similar substitutions and modifications to other plants of the genus Lilium and other tissues according to the present application, which are considered to be included in the present application. It is obvious that the methods and applications described herein can be modified or appropriately changed and combined without departing from the content, spirit and scope of the present application, to realize and apply the present application technology. Obviously, the described embodiments are only a part of the embodiments of the present application, but not all the embodiments.

[0052] 1) The dry pieces of C. morii 49 kg were crushed and put into a low-pressure chromatographic column, and extracted by percolation with 70% methanol for 4 times, 24 h each time. The extract was obtained by suction filtration. The filtrate was concentrated at 60°C under reduced pressure until no alcohol was left, and a concentrated solution was obtained;

[0053] 2) The concentrated solution was extracted with an equal volume of ethyl acetate for 4 times, and ethyl acetate phase and water phase were obtained respectively;

[0054] 3) The ethyl acetate phase and water phase were concentrated at 50°C respectively, and then the samples were mixed with 60-80 mesh silica gel and dried by blowing air at 45°C;

[0055] 4) The silica gel with a mesh size of 200-300 was used as the filler, and petroleum ether-ethyl acetate was used as the mobile phase (petroleum ether: ethyl acetate = 50:1 ~ 0:1) for sample loading, elution and segmentation;

[0056] 5) After the segmented eluate was developed by spotting with petroleum ether-ethyl acetate as the developing agent, 10% sulfuric acid ethanol was used for coloration, 10 segments of crude extract were obtained, and after HPLC analysis, the peaks near the retention time of the standard samples of Wangbili glycoside A and Wangbili glycoside B were compared, and segments 6-10 were taken as the crude preparation;

[0057] 6) The crude extract was further prepared by C 18 18 column, methanol: 0.1% phosphoric acid water = 40:60 as the mobile phase for elution, and detection at 310 nm, and the crude fraction was further divided into 10 segments Fr1-Fr10, and then further prepared by acetonitrile: 0.1% phosphoric acid water = 10:90 ~ 20:80, and the acetonitrile: 0.1% phosphoric acid water = 35:65 was used for column flushing;

[0058] 7) The acetonitrile-0.1% phosphoric acid water or tetrahydrofuran-0.1% phosphoric acid water was used for repeated preparation and purification, and different monomers were obtained after evaporation under reduced pressure.

[0059] In step 7), Fr3 was prepared by HPLC, acetonitrile: 0.1% phosphoric acid water = 15:85, Fr3-1 was obtained, and then Fr3-1 was prepared by tetrahydrofuran: 0.1% phosphoric acid water (ρ=0.985), and compound I ((2 S )-1- O-E - p -coumaroyl-3-[ O - β -D-glucopyranosyl-(1→6)- O - β -D-glucopyranosyl]glycerol) (94.36%); Fr7 was prepared by HPLC, acetonitrile: 0.1% phosphoric acid water = 18:82, and compound II ((2 S )-1- O-E - p-coumaroyl-2- O -acetyl-3-[ O - β -D-glucopyranosyl-(1→6)- O - β -D-glucopyranosyl]glycerol)(97.91%); Fr9 was prepared by HPLC, methanol:0.1% phosphoric acid water=20:80, at 10.5', compound III ((2 S )-1- O-Z - p -coumaroyl-2- O -acetyl-3- O - β -D-glucopyranosylglycerol) (98.07%).

[0060] Example 2: Compound Identification

[0061] Compound I: Off-white powder; PDA: 310 nm; ESI-MS m / z = 561.1 [MH] - Based on the plant origin, NMR data, and mass spectrometry data, this compound can be preliminarily identified as a coumarin compound. The proton spectrum shows a low-field signal of six protons (δ). H 7.65 (1H, d, J=16.0), 7.47 (1H, d, J=8.5), 6.80 (2H, d, J=8.0), 6.37 (1H, d, J=16.0), the two telomere hydrogen proton signals δ H 4.37 (1H, d, J=8.0), 4.31 (1H, d, J=8.0). The NMR data of the compound are basically consistent with those reported in the literature for lily glycoside A, indicating that it has the same structural unit as lily glycoside A. HSQC was used to assign all C and H atoms to it, and HMBC revealed δ... H 4.31 (H-1″) and δ C 72.7 (C-3) correlation, and δ H 3.91 (H-3) and δ C The correlation of 104.8 (C-1″) indicates that glucose is bonded to the 3-carbon position; simultaneously, δ H 4.37(H-1′″) and δ C The 69.9 (C-6″) correlation indicates that another glucose unit is attached to the 6-position of the first glucose. In addition, δ... H 4.24 (H-1) and δ C169.1 (C-9') correlation, indicating that the coumaroyl group is connected to the carbon at position 1. The α, β coupling constant of the coumaroyl group is 16.0 Hz, indicating that the structural unit of the compound is trans-coumaroyl group. Figure 1 In summary, the compound is a new compound, and is identified as (2 S )-1- O-E - p -coumaroyl-3-[ O - β -D-glucopyranosyl-(1→6)- O - β -D-glucopyranosyl]glycerol.

[0062] Table 1. The PDA and ESI-MS data of compound I 1 H-NMR (500 MHz) and 13 C-NMR (125 MHz) data assignment

[0063] Carbon position δH δC Carbon position δH δC 1 4.24 (m) 66.5 1″ 4.31 (d, J = 8.0 Hz) 104.8 2 4.07 (m) 69.9 2″ 3.36 (m) 75.0 3 3.91 (m)3.78 (m) 72.7 3″ 3.27 (m) 77.9 1′ - 127.0 4″ 3.31 (m) 71.5 2′ 7.47 (d, J = 8.5 Hz) 131.2 5″ 3.49 (m) 77.0 3′ 6.80 (d, J = 8.0 Hz) 116.8 6″ 4.18 (dd, J = 11.5, 2.5 Hz), 3.75 (m) 69.9 4′ - 161.2 1″ 4.37 (d, J = 8.0 Hz) 104.9 5′ 6.80 (d, J = 8.0 Hz) 116.8 2″ 3.22 (m) 75.1 6′ 7.47 (d, J = 8.5 Hz) 131.2 3″ 3.27 (m) 77.9 7′ 7.65 (d, J = 16.0 Hz) 146.8 4″ 3.31 (m) 71.5 8′ 6.37 (d, J = 16.0 Hz) 115.0 5″ 3.36 (m) 77.7 9′ - 169.1 6″ 3.87 (dd, J = 12.0, 2.0 Hz)3.67 (dd, J = 11.5, 5.0 Hz) 62.7

[0064] Compound II: white powder; PDA: 312 nm; ESI-MS m / z = 603.2 [M-H] - In combination with the plant source, NMR data and mass spectrometry data, it can be initially judged that the compound is a coumarin compound. From the hydrogen spectrum, the low field shows six hydrogen proton signals δ H 7.62 (1H, d, J=16.0), 7.47 (1H, d, J=8.5), 6.81 (2H, d, J=8.0), 6.33 (1H, d, J=16.0), the high field part shows a methyl signal δ H 2.07 (3H, s), two sugar end group hydrogen proton signals δ H 4.38 (1H, d, J=7.5), 4.30 (1H, d, J=7.5). The NMR data of the compound is basically consistent with the data of Wangbilyoside A reported in the literature, indicating that it has the same structural unit as Wangbilyoside A. Through HSQC, the carbon and hydrogen of the compound are fully assigned, and it is found from HMBC that δ H 4.30 (H-1") is correlated with δ C 68.9 (C-3) is correlated, and at the same time, δ H 3.82 (H-3) is correlated with δ C 104.6 (C-1") is correlated, indicating that the glucose is connected to the carbon at position 3; at the same time, δ H 4.16 (H-6") is correlated with δ C104.9 (C-1'") related, indicating that another glucose unit is linked to the 6 position of the first glucose. In addition, δ H 4.49 (H-1) is related to δ C 168.8 (C-9') related, indicating that the p-coumaroyl group is linked to the 1 carbon, δ H 5.31 (H-2) is related to 172.3 (C-O-COCH3), indicating that the acetyl group is linked to the 2 carbon. The α, β coupling constant of the p-coumaroyl group is 16.0 Hz, indicating that the structure unit of the compound is trans-p-coumaroyl group (C-9' is related to δ Figure 2 , Table 2). Based on the above, the compound is a new compound, and is identified as, (2 S )-1- O-E - p -coumaroyl-2- O -acetyl-3-[ O - β -D-glucopyranosyl-(1→6)- O - β -D-glucopyranosyl]glycerol.

[0065] Table 2. Compound II 1 H-NMR (500 MHz) and 13 C-NMR (125 MHz) data attribution

[0066] Carbon position δH δC Carbon position δH δC 1 4.49 (dd, J = 12.0, 3.5 Hz)4.34(q, J = 6.0 Hz) 63.9 1″ 4.30 (d, J = 7.5 Hz) 104.6 2 5.31 (m) 72.1 2″ 3.21 (m) 74.9 3 3.82 (q, J = 6.0 Hz)4.03 (q, J=5.5 Hz) 68.9 3″ 3.34 (m) 77.9 1′ - 127.0 4″ 3.34 (m) 71.4 2′ 7.47 (d, J = 8.5 Hz) 131.2 5″ 3.46 (m) 77.1 3′ 6.81 (d, J = 8.0 Hz) 116.8 6″ 4.16 (d, J = 9.5 Hz), 3.76 (q, J= 6.0 Hz) 69.9 4′ - 161.8 1″ 4.38 (d, J = 7.5 Hz) 104.9 5′ 6.81 (d, J = 8.0 Hz) 116.8 2″ 3.28 (m) 75.0 6′ 7.47 (d, J = 8.5 Hz) 131.2 3″ 3.34 (m) 77.9 7′ 7.62 (d, J = 16.0 Hz) 147.0 4″ 3.34 (m) 71.5 8′ 6.33 (d, J = 16.0 Hz) 114.6 5″ 3.34 (m) 77.8 9′ - 168.8 6″ 3.86 (dd, J = 11.0, 2.0 Hz), 3.66(dd, J = 12.0, 5.0 Hz) 62.7 Ac - 172.3 2.07 (s) 20.9

[0067] Compound III: According to the NMR and mass spectrum data, it can be preliminarily judged that the compound is a simple coumarin compound. From the hydrogen spectrum, the low field shows six hydrogen proton signals δ H 7.60 (2H, d, J=9.0), 6.90 (1H, d, J=12.5), 6.76 (2H, d, J=9.0), 5.77 (1H, d, J=12.5), and the high field shows a methyl signal δ H 2.03 (3H, s). The nuclear magnetic data of the compound is basically the same as the data reported in the literature for Wangbili glycoside A, indicating that it has the same structure unit as Wangbili glycoside A. Through HSQC, the carbon and hydrogen are fully attributed, and from HMBC, it is found that δ H 4.26 (H-1") is related to δ C 68.7 (C-3) is related, and at the same time, δ H 3.98 (H-3) is related to δ C 104.6 (C-1") is related, indicating that the glucose is linked to the 3 carbon; in addition, δ H 4.28 (H-1) is related to δC 167.8 (C-9') related to the coumaroyl group attached to the carbon at position 1, δ H 5.20 (H-2) related to 172.2 (C-O- C CH3) indicating the acetyl group is attached to the carbon at position 2. The hydrogen spectrum found the coupling constant J 7′8′ = 12.5 Hz for the coumaroyl group at positions 7' and 8', while J 7′8′ = 16.0 Hz for the coumaroyl group at positions 7' and 8' of Wang Baiyi Glycoside A. The coupling constant for the general cis double bond is 8-12 Hz, while the coupling constant for the trans double bond is 12-18 Hz; meanwhile, the α, β coupling constant for the cis coumaroyl group is 12.5-13.0 Hz, and the α, β coupling constant for the trans coumaroyl group is 15.6-16.0 Hz, indicating that the structural unit of the compound is the cis coumaroyl group Figure 3 , Table 3). Based on the above, the compound is a new compound, and is identified as (2 S )-1- O-Z - p -coumaroyl-2- O -acetyl-3- O - β -D-glucopyranosylglycerol.

[0068] Table 3. H-NMR (500 MHz) and 1 C-NMR (125 MHz) of Compound III 13 C-NMR (125 MHz)

[0069] Carbon position δH δC Carbon position δH δC 1 4.46 (dd, J = 12.5, 3.5 Hz)4.28 (q,J = 6.0 Hz) 63.6 1″ 4.26 (d, J = 7.5 Hz) 104.6 2 5.20 (m) 72.0 2″ 3.17 (t, J = 8.0 Hz) 74.9 3 3.98 (q, J = 6.0 Hz), 3.72 (q, J =5.5 Hz) 68.7 3″ 3.32 (m) 78.0 1′ - 127.6 4″ 3.27 (m) 71.5 2′ 7.60 (d, J = 9.0 Hz) 133.5 5″ 3.32 (m) 77.9 3′ 6.76 (d, J = 9.0 Hz) 115.8 6″ 3.86 (dd, J = 12.0, 2.0 Hz), 3.67(dd, J = 12.0, 5.0 Hz) 62.7 4′ - 160.0 Ac - 172.2 5′ 6.76 (d, J = 9.0 Hz) 115.8 2.03 (s) 20.9 6′ 7.60 (d, J = 9.0 Hz) 133.5 7′ 6.90 (d, J = 12.5 Hz) 145.5 8′ 5.77 (d, J = 12.5 Hz) 116.1 9′ - 167.8

[0070] Example 3: Promotion of Wang Baiyi Glycoside on the Growth of Fibroblasts

[0071] Cell strain: The cells used in this test are mouse embryonic fibroblasts NIH-3T3.

[0072] Drugs: The test drugs used in this study are three new Wang Baiyi Glycosides prepared in the previous stage.

[0073] Reagents: Fetal bovine serum (Sijiqing), DMEM high-sugar medium fetal bovine serum (FBS) (containing 10% fetal bovine serum), penicillin (Solebao), streptomycin (Solebao), thiazole blue (MTT) (Sigma Aldrich), dimethyl sulfoxide (DMSO), 0.25% trypsin (Solebao), etc.

[0074] Instruments: CO2 incubator, low-speed centrifuge, enzyme marker, optical microscope, etc.

[0075] Solution preparation:

[0076] Each king lily glycoside was prepared into a 1 mg / mL stock solution with PBS, sterilized by 0.22 μm filtration and stored at -20℃ for standby. When used, each king lily glycoside stock solution was diluted with cell culture solution into working solutions of 0, 2, 5, 10, 20, 40, 80, 100 μg / mL.

[0077] Cell passage:

[0078] Each cell was added to DMEM medium containing 10% fetal bovine serum, 1% penicillin and streptomycin, and cultured at 37℃, 5% CO2. After 80% ~ 90% of the cells adhered, the culture medium was discarded and washed once with 1 × PBS. Trypsin was added for enzyme digestion, and after enzyme digestion was complete, the culture medium was added to stop the reaction. After repeatedly blowing with a dropper to make a uniform cell suspension, the cells were divided into 2-3 bottles and placed in a culture incubator for passage.

[0079] Cell activity detection:

[0080] Cell toxicity determination was performed using the MTT method, with specific steps as described in Chen et al (2022) with slight modifications.

[0081] a. After enzyme digestion, the mouse embryonic fibroblast NIH-3T3 cells after passage were prepared into a cell suspension with cell culture solution;

[0082] b. Inoculated in a 96-well plate at a concentration of about 5 × 10 3 cells per well and cultured at 37℃, 5% CO2;

[0083] c. After 24 h of culture, the culture medium was discarded and different concentrations of king lily glycoside cell culture solution were added (3 replicate wells per treatment), and the culture was continued for 48 h;

[0084] d. After taking pictures with a microscope, the culture medium was discarded, washed 3 times with sterile PBS, and 100 μL of MTT solution (5 mg / mL) was added to each well. After slow shaking, the culture was continued for 2 h;

[0085] e. The culture medium was discarded, 150 μL of DMSO was added to each well, and after low-speed shaking at room temperature for 10 min, the absorbance of the reaction solution was detected at 490 nm using a microplate reader (with the blank well as the zero reference).

[0086] The application takes mouse embryonic fibroblasts (NIH-3T3) as the test cell, and uses MTT method to detect the influence of three kinds of lilytusifolin on the cell activity of NIH-3T3 in the cell passage process in the concentration range of 5-100 μg / mL. The results show that the compound I has a promoting effect on the growth of NIH-3T3 at a relatively low concentration (within 40 μg / mL); the compound II and the compound III have a promoting effect on the growth of NIH-3T3 within 100 μg / mL, indicating that the newly found lilytusifolin components have no or less toxicity to normal cell toxicity, have an important role in skin protection and wound repair, and can be used for the development of skin protection and repair cosmetic and medical products.

[0087] The application discloses a new type of lilytusifolin compound, which is a new chemical component found in lily. The application identifies the structure of the compound separated by the above method through chromatography and modern spectroscopy. The application also uses mouse embryonic fibroblasts NIH-3T3 to perform cell proliferation experiments and finds that the compound has a function of promoting skin cell proliferation, and can be used in the field of skin protection and repair.

[0088] It is apparent to those skilled in the art that the application is not limited to the details of the foregoing exemplary embodiments, and that the application can be implemented in other concrete forms without departing from the spirit or essential characteristics of the application. Therefore, the embodiments should be considered as exemplary and non-limiting, and the scope of the application is defined by the appended claims rather than the above description, and all changes falling within the meaning and range of the equivalent elements of the claims are intended to be included in the application.

[0089] In addition, it should be understood that although the present specification is described in terms of embodiments, not every embodiment contains only one independent technical solution, and the description of the specification is only for the sake of clarity. Those skilled in the art should consider the specification as a whole, and the technical solutions in each embodiment can be properly combined to form other embodiments that those skilled in the art can understand.

Claims

1. A class of shizukainosides, characterized in that, Any one of the following compounds: Compound I, Compound II, Compound III; the structural formula is as follows: ； Compound I ； Compound II ； Compound III.

2. Use of the Wangbaiilyoside compound or pharmaceutically acceptable salt thereof according to claim 1 in the preparation of skin repair and protection drugs and cosmetics.

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