A triterpenoid acid compound, an extraction method and application thereof, a pharmaceutical composition, and a whitening and freckle-removing daily chemical product

Abstract

The present application relates to the technical field of medicine, in particular to a kind of triterpenoid acid compound and its extraction method and application, pharmaceutical composition, whitening and freckle daily chemical product. Through in vitro whitening activity research, it is found that the triterpenoid acid compound (compound 1~39) provided in the present application can well inhibit the generation of cell melanin under the stimulation of alpha-MSH, inhibit the activity of tyrosinase in cell under the stimulation of alpha-MSH, has excellent whitening activity, and has good application prospect in the preparation of whitening and freckle medicine and whitening and freckle daily chemical product. Moreover, the triterpenoid acid compound provided in the present application is a natural compound in poria cocos, and has high safety.

Description

Technical Field

[0001] This invention relates to the field of pharmaceutical technology, specifically to a triterpene acid compound, its extraction method and application, pharmaceutical compositions, and skin whitening and spot-fading daily chemical products. Background Technology

[0002] Melanin is synthesized by melanocytes in the body, and its quantity and type determine skin color. Accumulation or disordered distribution of melanin in the skin can cause hyperpigmentation disorders, mainly including melasma, age spots, freckles, and post-inflammatory hyperpigmentation. Currently, most skin-whitening raw materials work by reducing melanin production to alleviate pigmentation and thus exert their whitening effect. Inhibiting tyrosinase activity is one of the main strategies for reducing melanin production. However, skin-whitening raw materials that inhibit tyrosinase activity, such as kojic acid and hydroquinone, can cause side effects such as skin sensitivity and cancer with long-term use. Therefore, utilizing plant extracts and their active ingredients to inhibit tyrosinase activity and reduce melanin production is increasingly promising.

[0003] Poria cocos ( Poria cum Pini Radix (a type of pine root) is the white part naturally found in the center of the sclerotium of Poria cocos, where a pine root diameter does not exceed 1.5 cm. The Ming Dynasty medical text *Ben Cao Jing Shu* states, "Pini Radix grows by embracing the heartwood, thus distinguishing it from Poria cocos." It has a sweet and bland taste, and is neutral in nature; it enters the heart and spleen meridians; it has calming, soothing, and diuretic effects. Modern pharmacology shows that Poria cocos has good skin-whitening and skin-care effects. However, the components in Poria cocos extract are complex, with multiple components exhibiting synergistic or antagonistic effects on tyrosinase inhibition, and the content of these active ingredients is relatively low. Therefore, the inhibitory activity of plant extracts on tyrosinase is generally less than that of monomeric components. Currently, research on the skin-whitening activity of Poria cocos is relatively limited, making it significant to obtain monomeric compounds with excellent skin-whitening activity from Poria cocos. Summary of the Invention

[0004] Therefore, the purpose of this invention is to provide a triterpene acid compound, its extraction method and application, a pharmaceutical composition, and a skin-whitening and spot-fading daily chemical product. The triterpene acid compound provided by this invention is a natural compound from the traditional Chinese medicine Poria cocos, and has excellent skin-whitening activity.

[0005] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a triterpene acid compound, comprising any one of compounds 1 to 7: ; Compound 1: R1 is -OH, R2 is -H, R3 is -OH; Compound 2: R1 is -H, R2 is R3 is -H; Compound 4: R4 is ; Compound 5: R4 is ; Compound 6: R4 is .

[0006] This invention also provides a method for extracting the triterpenoid compounds described in the above technical solution, comprising the following steps: Poria cocos powder was extracted with methanol-water to obtain a crude methanol extract. The crude methanol extract was subjected to silica gel column chromatography to obtain components A6, A8, and A9, respectively. The volume fraction of methanol in the methanol-water mixture was 95-100%. The silica gel column chromatography was performed using dichloromethane-methanol as the eluent for a first gradient elution, with a volume ratio of dichloromethane to methanol of 100:0 to 0:100 during the first gradient elution. (a) Extraction method of any one of compound 1, compound 2 and compound 4 The component A9 was subjected to ODS RP-18 column chromatography to obtain components A9-29, A9-32, and A9-33, respectively; the ODS RP-18 column chromatography was performed by second-gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the second-gradient elution was 20:80 to 100:0. The extraction method of compound 1 includes the following steps: separating component A9-33 using Sephadex LH-20 to obtain component A9-33-8, and purifying component A9-33-8 using preparative HPLC to obtain compound 1; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is third gradient elution, and the volume ratio of mobile phase A to mobile phase B during the third gradient elution process is 65:35~80:20; The extraction method of compound 2 includes the following steps: separating component A9-29 using Sephadex LH-20 to obtain component A9-29-9, and purifying component A9-29-9 using preparative HPLC to obtain compound 2; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fourth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fourth gradient elution process is 70:30~85:15; The extraction method of compound 4 includes the following steps: separating component A9-32 using Sephadex LH-20 to obtain component A9-32-5, and purifying component A9-32-5 using preparative HPLC to obtain compound 4; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fifth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fifth gradient elution is 55:45~70:30; (b) Extraction method of any one of compounds 3, 6 and 7 The component A8 was subjected to ODS RP-18 column chromatography to obtain components A8-26, A8-28 and A8-29, respectively; the ODS RP-18 column chromatography was performed by a sixth gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the sixth gradient elution was 20:80~100:0. The extraction method of compound 3 includes the following steps: separating component A8-29 using Sephadex LH-20 to obtain component A8-29-4, and purifying component A8-29-4 using preparative HPLC to obtain compound 3; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is seventh gradient elution, and the volume ratio of mobile phase A to mobile phase B during the seventh gradient elution is 55:45~70:30; The extraction method of compound 6 includes the following steps: separating component A8-28 using Sephadex LH-20 to obtain component A8-28-6; purifying component A8-28-6 using semi-preparative HPLC to obtain compound 6; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the semi-preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is eighth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the eighth gradient elution is 50:50~70:30; The extraction method of compound 7 includes the following steps: separating component A8-26 using Sephadex LH-20 to obtain component A8-26-3, and purifying component A8-26-3 using preparative HPLC to obtain compound 7; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is the ninth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the ninth gradient elution is 40:60~55:45; (c) The extraction method for compound 5 includes the following steps: The component A6 was subjected to ODS RP-18 column chromatography to obtain component A6-14; the ODS RP-18 column chromatography was performed by elution with methanol-water as the eluent in a tenth gradient, and the volume ratio of methanol to water in the tenth gradient elution process was 20:80~100:0. The component A6-14 was allowed to stand in methanol to precipitate a solid. The obtained solid was washed with an aqueous methanol solution to obtain solid A6-14a. The solid A6-14a was purified by preparative HPLC to obtain compound 5. The conditions for the preparative HPLC purification included: mobile phase A was acetonitrile, mobile phase B was 0.01~0.5 v / v% formic acid aqueous solution, and the eleventh gradient elution method was used. The volume ratio of mobile phase A to mobile phase B during the eleventh gradient elution was 60:40~75:25.

[0007] Preferably, the volume ratio of dichloromethane to methanol during the first gradient elution process is 100:0, 50:1, 25:1, 15:1, 10:1, 6:1, 3:1, 1:1 and 0:100, respectively.

[0008] Preferably, the volume ratio of methanol to water during the second gradient elution process is 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, respectively. The elution program for the third gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 65:35 to 80:20; The elution program for the fourth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 70:30 to 85:15; The elution program for the fifth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:30.

[0009] Preferably, the volume ratio of methanol to water in the sixth gradient elution process is 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0 respectively; The elution program for the seventh gradient is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:30; The elution program for the eighth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A and mobile phase B changes linearly from 50:50 to 70:30; The elution program for the ninth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 40:60 to 55:45.

[0010] Preferably, the volume ratio of methanol to water in the tenth gradient elution process is 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0 respectively; The eleventh gradient elution program is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 60:40 to 75:25.

[0011] The present invention also provides the application of triterpene acid compounds in the preparation of whitening and spot-fading drugs or in whitening and spot-fading daily chemical products, wherein the triterpene acid compounds include at least one of compounds 1 to 39, wherein compounds 1 to 7 are the triterpene acid compounds described in the above technical solution; Among them, compound 8: R5 is β-OA, and R6 is -OH; Compound 9: R5 is α-OOCCH3, R6 is -OH; Compound 10: R5 is β-OA', R6 is -OH; Compound 11: R5 is β-OH, R6 is -H; Compound 12: R5 is β-OOCCH3, R6 is -OH; Compound 13: R5 is β-OH, R6 is -OH; Compound 14: R5 is α-OH, R6 is -OH; Where A in β-OA is ;A' in β-OA' is ; Compound 16: R7 is β-OH, R8 is -H, and R9 is -OH; Compound 17: R7 is α-OH, R8 is -H, and R9 is -OH; Compound 18: R7 is β-OH, R8 is -OH, and R9 is -OH; Compound 19: R7 is β-OH, R8 is -H, and R9 is -H; Compound 20: R 10 For β-OH, R 11 -H; Compound 21: R 10 For β-OOCCH3, R 11 It is -OH; Compound 22: R 10 For β-OH, R 11 It is -OH; Compound 23: R 12 For -OH, R 13 -H; Compound 24: R 12 For -OOCCH3, R 13 -OH Compound 25: R 12 For -OH, R 13 It is -OH; Compound 26: R 14 For -CH3, R 15 -H, R 16 It is -OH; Compound 27: R 14 -H, R 15 -H, R 16 It is -OH; Compound 28: R 14 -H, R 15 For -OH, R 16 It is -OH; Compound 29: R 14 For -CH3, R 15 -H, R 16 -H; Compound 30: R 17 -H, R 18 -H, R 19 -H; Compound 31: R 17 -H, R 18 -H, R 19 It is -OH; Compound 32: R 17 For -OH, R 18 -H, R 19 -H; Compound 33: R 17 -H, R 18 For -CH2OH, R19 It is -OH; Compound 34: R 20 -H, R 21 -H, R 22 For -OH, R 23 -H; Compound 35: R 20 -H, R 21 For -CH2OH, R 22 For -OH, R 23 It is β-OH; Compound 36: R 20 For -OH, R 21 -H, R 22 -H, R 23 -H; Compound 37: R 24 -H, R 25 It is -OH; Compound 38: R 24 For -OH, R 25 -H; Compound 39: R 24 -H, R 25 It is -H.

[0012] The present invention also provides a pharmaceutical composition comprising an active ingredient and pharmaceutically acceptable excipients, wherein the active ingredient comprises a triterpene acid compound, and the triterpene acid compound comprises at least one of compounds 1 to 39 used in the applications described above.

[0013] The present invention also provides a skin whitening and spot-fading daily chemical product, characterized in that it includes a skin whitening active ingredient and excipients acceptable in the daily chemical industry, wherein the skin whitening active ingredient includes triterpene acid compounds, and the triterpene acid compounds include at least one of compounds 1 to 39 in the application described in the above technical solution.

[0014] Preferably, the excipients acceptable in the daily chemical industry include at least one of solvents, humectants, thickeners, pH adjusters, oils, emulsifiers, skin conditioning agents, antioxidants, and chelating agents.

[0015] In vitro whitening activity studies revealed that the triterpenoid compounds (compounds 1-7) provided by this invention can effectively inhibit the production of melanin in cells stimulated by α-MSH and exhibit high inhibition of intracellular tyrosinase activity under α-MSH stimulation, demonstrating excellent whitening activity. They show great promise for the preparation of whitening and spot-fading drugs and daily whitening and spot-fading products. Furthermore, the triterpenoid compounds provided by this invention are natural compounds found in Poria cocos, exhibiting high safety.

[0016] In vitro whitening activity studies revealed that the triterpenoid compounds (compounds 8-39) provided in this invention can effectively inhibit melanin production in cells stimulated by α-MSH and exhibit high inhibition of intracellular tyrosinase activity under α-MSH stimulation, demonstrating excellent whitening activity. They show great promise for the preparation of whitening and spot-fading drugs and daily whitening and spot-fading products. Furthermore, the triterpenoid compounds provided in this invention are natural compounds from Poria cocos, exhibiting high safety.

[0017] This invention uses Poria cocos as raw material and obtains triterpenoid compounds through methanol-water extraction, silica gel column chromatography, reversed-phase column chromatography, gel chromatography, and preparative high-performance liquid chromatography purification of Poria cocos powder. The extraction method provided by this invention is simple in steps, easy to operate, has low production cost, is environmentally friendly, and is suitable for industrial production. Detailed Implementation

[0018] This invention provides a triterpene acid compound, comprising any one of compounds 1 to 7: ; Compound 1: R1 is -OH, R2 is -H, R3 is -OH; Compound 2: R1 is -H, R2 is R3 is -H; Compound 4: R4 is ; Compound 5: R4 is ; Compound 6: R4 is .

[0019] This invention also provides a method for extracting the triterpenoid compounds described in the above technical solution, comprising the following steps: Poria cocos powder was extracted with methanol-water to obtain a crude methanol extract. The crude methanol extract was subjected to silica gel column chromatography to obtain components A6, A8, and A9, respectively. The volume fraction of methanol in the methanol-water mixture was 95-100%. The silica gel column chromatography was performed using dichloromethane-methanol as the eluent for a first gradient elution, with a volume ratio of dichloromethane to methanol of 100:0 to 0:100 during the first gradient elution. (a) Extraction method of any one of compound 1, compound 2 and compound 4 The component A9 was subjected to ODS RP-18 column chromatography to obtain components A9-29, A9-32, and A9-33, respectively; the ODS RP-18 column chromatography was performed by second-gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the second-gradient elution was 20:80 to 100:0. The extraction method of compound 1 includes the following steps: separating component A9-33 using Sephadex LH-20 to obtain component A9-33-8, and purifying component A9-33-8 using preparative HPLC to obtain compound 1; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is third gradient elution, and the volume ratio of mobile phase A to mobile phase B during the third gradient elution process is 65:35~80:20; The extraction method of compound 2 includes the following steps: separating component A9-29 using Sephadex LH-20 to obtain component A9-29-9, and purifying component A9-29-9 using preparative HPLC to obtain compound 2; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fourth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fourth gradient elution process is 70:30~85:15; The extraction method of compound 4 includes the following steps: separating component A9-32 using Sephadex LH-20 to obtain component A9-32-5, and purifying component A9-32-5 using preparative HPLC to obtain compound 4; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fifth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fifth gradient elution is 55:45~70:30; (b) Extraction method of any one of compounds 3, 6 and 7 The component A8 was subjected to ODS RP-18 column chromatography to obtain components A8-26, A8-28 and A8-29, respectively; the ODS RP-18 column chromatography was performed by a sixth gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the sixth gradient elution was 20:80 to 100:0. The extraction method of compound 3 includes the following steps: separating component A8-29 using Sephadex LH-20 to obtain component A8-29-4, and purifying component A8-29-4 using preparative HPLC to obtain compound 3; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is seventh gradient elution, and the volume ratio of mobile phase A to mobile phase B during the seventh gradient elution is 55:45~70:30; The extraction method of compound 6 includes the following steps: separating component A8-28 using Sephadex LH-20 to obtain component A8-28-6; purifying component A8-28-6 using semi-preparative HPLC to obtain compound 6; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the semi-preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is eighth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the eighth gradient elution is 50:50~70:30; The extraction method of compound 7 includes the following steps: separating component A8-26 using Sephadex LH-20 to obtain component A8-26-3, and purifying component A8-26-3 using preparative HPLC to obtain compound 7; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is the ninth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the ninth gradient elution is 40:60~55:45; (c) The extraction method for compound 5 includes the following steps: The component A6 was subjected to ODS RP-18 column chromatography to obtain component A6-14; the ODS RP-18 column chromatography was performed by elution with methanol-water as the eluent in a tenth gradient, and the volume ratio of methanol to water in the tenth gradient elution process was 20:80~100:0. The component A6-14 was allowed to stand in methanol to precipitate a solid. The obtained solid was washed with an aqueous methanol solution to obtain solid A6-14a. The solid A6-14a was purified by preparative HPLC to obtain compound 5. The conditions for the preparative HPLC purification included: mobile phase A was acetonitrile, mobile phase B was 0.01~0.5 v / v% formic acid aqueous solution, and the eleventh gradient elution method was used. The volume ratio of mobile phase A to mobile phase B during the eleventh gradient elution was 60:40~75:25.

[0020] Unless otherwise specified, the materials and equipment used in this invention are all commercially available products in the field.

[0021] This invention involves methanol-water extraction of Poria cocos powder to obtain a crude methanol extract. The Poria cocos powder is extracted with methanol to obtain a crude methanol extract. In this invention, the Poria cocos powder can be obtained by pulverizing dried Poria cocos; the particle size of the Poria cocos powder can be ≥20 mesh. In this invention, the volume fraction of methanol in the methanol-water mixture is 95~100%, specifically 95%, 96%, 97%, 98%, 99%, or 100%. In this invention, the solid-liquid ratio of the Poria cocos powder to the methanol-water mixture can be 1kg:2~5L, or 1kg:3~4L, specifically 1kg:2L, 1kg:2.5L, 1kg:3L, 1kg:3.5L, 1kg:4L, 1kg:4.5L, or 1kg:5L. In this invention, the extraction temperature can be room temperature, and the number of extractions can be 3 to 7 times, specifically 3, 4, 5, 6, or 7 times; the extraction time for a single extraction can be 24 to 48 hours, specifically 24 hours, 26 hours, 28 hours, 30 hours, 32 hours, 34 hours, 36 hours, 38 hours, 40 hours, 42 hours, 44 hours, 46 hours, or 48 hours. In this invention, the extracts are combined after extraction and concentrated to obtain a crude methanol extract. In this invention, the concentration can include vacuum concentration, and the concentration temperature can be 50 to 55°C, specifically 50°C, 51°C, 52°C, 53°C, 54°C, or 55°C.

[0022] After obtaining the crude methanol extract, the present invention performs silica gel column chromatography on the crude methanol extract to obtain components A6, A8, and A9, respectively. In the present invention, the silica gel column chromatography is performed using dichloromethane-methanol as the eluent for a first gradient elution. During the first gradient elution, the volume ratio of dichloromethane to methanol is 100:0 to 0:100, specifically 100:0, 50:1, 25:1, 15:1, 10:1, 6:1, 3:1, 1:1, and 0:100. In the present invention, the silica gel used for the silica gel column chromatography can have a particle size of 200-300 mesh. In the present invention, during the silica gel column chromatography, thin-layer chromatography monitoring is used to combine identical components, resulting in a total of 10 components, denoted as components A1 to A10 (i.e., components A1, A2, A3, A4, A5, A6, A7, A8, A9, and A10).

[0023] The extraction methods for any one of compounds 1, 2, and 4 are described below.

[0024] In this invention, component A9 is subjected to ODS RP-18 column chromatography to obtain components A9-29, A9-32, and A9-33. In this invention, the ODS RP-18 column chromatography uses methanol-water as the eluent for a second gradient elution. The volume ratio of methanol to water during the second gradient elution is 20:80 to 100:0, specifically 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, and 100:0. In this invention, the ODS RP-18 column chromatography yields a total of 33 components, denoted as components A9-1 to A9-33.

[0025] In this invention, the extraction method of compound 1 includes the following steps: separating component A9-33 using Sephadex LH-20 to obtain component A9-33-8, and purifying component A9-33-8 using preparative HPLC to obtain compound 1. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; the Sephadex LH-20 separation yields a total of 8 components, denoted as components A9-33-1 to A9-33-8. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can be specifically 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is third gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the third gradient elution process is 65:35~80:20, specifically 0~40 min, and the volume ratio of mobile phase A to mobile phase B changes linearly from 65:35 to 80:20; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0026] In this invention, the extraction method of compound 2 includes the following steps: separating component A9-29 using Sephadex LH-20 to obtain component A9-29-9; and purifying component A9-29-9 using preparative HPLC to obtain compound 2. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; a total of nine components are obtained from the Sephadex LH-20 separation, denoted as components A9-29-1 to A9-29-9. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can specifically be 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is fourth gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the fourth gradient elution process is 70:30~85:15, specifically 0~40 min, and the volume ratio of mobile phase A to mobile phase B changes linearly from 70:30 to 85:15; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0027] In this invention, the extraction method of compound 4 includes the following steps: separating component A9-32 using Sephadex LH-20 to obtain component A9-32-5, and purifying component A9-32-5 using preparative HPLC to obtain compound 4. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; the Sephadex LH-20 separation yields five components, denoted as components A9-32-1 to A9-32-5. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can specifically be 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is fifth gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the fifth gradient elution process is 55:45~70:30, specifically 0~40 min, and the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:30; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0028] The extraction methods for any one of compounds 3, 6, and 7 are described below.

[0029] In this invention, component A8 is subjected to ODS RP-18 column chromatography to obtain components A8-26, A8-28, and A8-29. In this invention, the ODS RP-18 column chromatography uses methanol-water as the eluent for a sixth gradient elution. The volume ratio of methanol to water during the sixth gradient elution is 20:80 to 100:1, specifically 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, and 100:0. A total of 29 components are obtained from the ODS RP-18 column chromatography, denoted as components A8-1 to A8-29.

[0030] In this invention, the extraction method of compound 3 includes the following steps: separating component A8-29 using Sephadex LH-20 to obtain component A8-29-4, and purifying component A8-29-4 using preparative HPLC to obtain compound 3. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; the Sephadex LH-20 separation yields four components, denoted as components A8-29-1 to A8-29-4. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can be specifically 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is seventh gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the seventh gradient elution process is 55:45~70:30, specifically 0~40 min, and the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:30; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0031] In this invention, the extraction method of compound 6 includes the following steps: separating component A8-28 using Sephadex LH-20 to obtain component A8-28-6; and purifying component A8-28-6 using semi-preparative HPLC to obtain compound 6. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; the Sephadex LH-20 separation yields six components, denoted as components A8-28-1 to A8-28-6. In this invention, the conditions for the semi-preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can be specifically 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is eighth gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the eighth gradient elution process is 50:50~70:30, specifically 0~40 min, and the volume ratio of mobile phase A to mobile phase B changes linearly from 50:50 to 70:30; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0032] In this invention, the extraction method of compound 7 includes the following steps: separating component A8-26 using Sephadex LH-20 to obtain component A8-26-3, and purifying component A8-26-3 using preparative HPLC to obtain compound 7. In this invention, methanol is used as the eluent for the Sephadex LH-20 separation; the Sephadex LH-20 separation yields six components, denoted as components A8-26-1 to A8-26-6. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can specifically be 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is ninth gradient elution, wherein the volume ratio of mobile phase A to mobile phase B during the ninth gradient elution process is 40:60~55:45, specifically 0~40 min, wherein the volume ratio of mobile phase A to mobile phase B changes linearly from 40:60 to 55:45; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0033] In this invention, the extraction method of compound 5 includes the following steps: performing ODS RP-18 column chromatography on component A6 to obtain component A6-14; allowing component A6-14 to stand in methanol to precipitate a solid, washing the obtained solid with methanol-water solution to obtain solid A6-14a, and purifying solid A6-14a by preparative HPLC to obtain compound 5. In this invention, the ODS RP-18 column chromatography is a tenth-gradient elution using methanol-water as the eluent, wherein the volume ratio of methanol to water in the tenth-gradient elution process is 20:80~100:0, specifically 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, and 100:0; the ODS RP-18 column chromatography yields 21 components, denoted as components A6-1 to A6-21. In this invention, the volume fraction of methanol in the methanol aqueous solution for washing can be 40-60%, or 45-55%, and specifically 50%. In this invention, the preparative HPLC purification conditions include: mobile phase A is acetonitrile, mobile phase B is a 0.01~0.5 v / v% formic acid aqueous solution, wherein the volume fraction of formic acid in the 0.01~0.5 v / v% formic acid aqueous solution can specifically be 0.01%, 0.02%, 0.05%, 0.08%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%; the elution method is eleventh gradient elution, wherein the volume ratio of acetonitrile to 0.01 v / v% formic acid aqueous solution during the eleventh gradient elution process is 60:40~75:25, specifically 0~40 min, wherein the volume ratio of mobile phase A to mobile phase B changes linearly from 60:40 to 75:25; the flow rate of the mobile phase system can be 8~10 mL / min, specifically 8 mL / min, 8.5 mL / min, 9 mL / min, 9.5 mL / min or 10 mL / min.

[0034] The present invention also provides the application of triterpene acid compounds in the preparation of whitening and spot-fading drugs or in whitening and spot-fading daily chemical products, wherein the triterpene acid compounds include at least one of compounds 1 to 39, wherein compounds 1 to 7 are the triterpene acid compounds described in the above technical solution; Among them, compound 8: R5 is β-OA, and R6 is -OH; Compound 9: R5 is α-OOCCH3, R6 is -OH; Compound 10: R5 is β-OA', R6 is -OH; Compound 11: R5 is β-OH, R6 is -H; Compound 12: R5 is β-OOCCH3, R6 is -OH; Compound 13: R5 is β-OH, R6 is -OH; Compound 14: R5 is α-OH, R6 is -OH; Where A in β-OA is ;A' in β-OA' is ; Compound 16: R7 is β-OH, R8 is -H, and R9 is -OH; Compound 17: R7 is α-OH, R8 is -H, and R9 is -OH; Compound 18: R7 is β-OH, R8 is -OH, and R9 is -OH; Compound 19: R7 is β-OH, R8 is -H, and R9 is -H; Compound 20: R 10 For β-OH, R 11 -H; Compound 21: R 10 For β-OOCCH3, R 11 It is -OH; Compound 22: R 10 For β-OH, R 11 It is -OH; Compound 23: R 12 For -OH, R 13 -H; Compound 24: R 12 For -OOCCH3, R 13 -OH Compound 25: R 12 For -OH, R 13 It is -OH; Compound 26: R 14 For -CH3, R 15 -H, R 16 It is -OH; Compound 27: R 14 -H, R 15 -H, R 16 It is -OH; Compound 28: R 14 -H, R 15 For -OH, R 16 It is -OH; Compound 29: R 14 For -CH3, R 15 -H, R 16 -H; Compound 30: R 17 -H, R 18 -H, R 19 -H; Compound 31: R 17 -H, R 18 -H, R 19 It is -OH; Compound 32: R 17 For -OH, R 18 -H, R 19 -H; Compound 33: R 17 -H, R 18 For -CH2OH, R 19 It is -OH; Compound 34: R 20 -H, R 21 -H, R 22 For -OH, R 23 -H; Compound 35: R 20 -H, R 21 For -CH2OH, R 22 For -OH, R 23 It is β-OH; Compound 36: R 20 For -OH, R 21 -H, R 22 -H, R 23 -H; Compound 37: R 24 -H, R 25 It is -OH; Compound 38: R 24 For -OH, R 25 -H; Compound 39: R 24 -H, R 25 It is -H.

[0035] In this invention, the skin whitening and spot-fading drug may include a drug for treating hyperpigmentation disorders of the skin, which may include one or more of melasma, age spots, freckles and post-inflammatory hyperpigmentation.

[0036] In vitro whitening activity studies revealed that the triterpenoid compounds (compounds 1-39) provided by this invention can effectively inhibit the production of melanin in cells stimulated by α-MSH and exhibit high inhibition of intracellular tyrosinase activity under α-MSH stimulation, demonstrating excellent whitening activity. They show great promise for the preparation of whitening and spot-fading drugs and daily whitening and spot-fading products. Furthermore, the triterpenoid compounds provided by this invention are natural compounds found in Poria cocos, exhibiting high safety.

[0037] This invention also provides a pharmaceutical composition, characterized in that it comprises an active ingredient and pharmaceutically acceptable excipients, wherein the active ingredient comprises a triterpene acid compound, and the triterpene acid compound comprises at least one of compounds 1 to 39 used in the applications described above. This invention does not specifically limit the pharmaceutically acceptable excipients or the dosage form of the pharmaceutical composition; any pharmaceutically acceptable excipients and dosage form well known to those skilled in the art can be used.

[0038] The present invention also provides a skin whitening and spot-fading daily chemical product, comprising a skin whitening active ingredient and excipients acceptable in the daily chemical industry, wherein the skin whitening active ingredient comprises a triterpene acid compound, and the triterpene acid compound comprises at least one of compounds 1 to 39 in the application described in the above technical solution.

[0039] In this invention, the excipients acceptable in the daily chemical industry may include at least one selected from solvents, humectants, thickeners, pH adjusters, oils, emulsifiers, skin conditioning agents, antioxidants, and chelating agents. This invention does not impose any particular limitations on the types and amounts of the solvents, humectants, thickeners, pH adjusters, oils, emulsifiers, skin conditioning agents, antioxidants, and chelating agents; any excipients known to those skilled in the art and suitable for use in whitening and spot-fading daily chemical products may be used.

[0040] To further illustrate the present invention, the following detailed descriptions, in conjunction with embodiments, illustrate the triterpenoid compounds, their extraction methods and applications, pharmaceutical compositions, and skin-whitening and spot-fading daily chemical products provided by the present invention. However, these descriptions should not be construed as limiting the scope of protection of the present invention.

[0041] Example 1 (1) 20 kg of dried Poria cocos (produced in Jinzhai County, Lu'an City, Anhui Province, China) was pulverized to 20 mesh and extracted 6 times with anhydrous methanol at room temperature. The extracts were combined and concentrated under reduced pressure at 50-55℃ to remove methanol, yielding 800 g of crude methanol extract. The ratio of dried Poria cocos to anhydrous methanol was 1 kg: 3 L, and the extraction time was 24 h per extraction.

[0042] (2) 743g of crude methanol extract was subjected to silica gel column chromatography (200-300 mesh silica gel) with dichloromethane-methanol as the eluent for gradient elution (100:0, 50:1, 25:1, 15:1, 10:1, 6:1, 3:1, 1:1 and 0:100, v / v). The components were monitored by thin-layer chromatography and the same components were combined to obtain a total of 10 components, which were named as component A1 (33g), component A2 (92g), component A3 (103g), component A4 (99g), component A5 (63g), component A6 (46g, dichloromethane:methanol volume ratio = 20:1), component A7 (18g), component A8 (6.3g, dichloromethane:methanol volume ratio = 30:1), component A9 (5g, dichloromethane:methanol volume ratio = 50:1) and component A10 (189g).

[0043] (3) Isolation and purification of component A9 Fraction A9 (5g) was subjected to ODS RP-18 column chromatography with gradient elution using methanol-water as the eluent (20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, v / v) to obtain 33 fractions, denoted as fractions A9-1 to A9-33.

[0044] Component A9-33 was separated using Sephadex LH-20 (methanol) to obtain 8 components (denoted as A9-33-1 to A9-33-8).

[0045] Fraction A9-33-2 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 65:35 → 80:20, mobile phase flow rate 8 mL / min) to obtain compound 16 (7.6 mg, t R =11.8min) and compound 8 (31.3mg, t R =12.8min).

[0046] Fraction A9-33-8 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 65:35 → 80:20, mobile phase flow rate 8 mL / min) to obtain compound 23 (12.6 mg, t). R =7.3min), compound 26 (7.7mg, t R =8.8min), Compound 1 (8.2mg, t R =8.7min) and compound 9 (6.1mg, tR=9.7min).

[0047] Component A9-32 was separated using Sephadex LH-20 (methanol) to obtain 5 components (denoted as A9-32-1 to A9-32-5).

[0048] Fraction A9-32-3 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 55:45 → 70:30, mobile phase flow rate 8 mL / min) to obtain compound 27 (5.8 mg, t R =10.2min).

[0049] Fraction A9-32-5 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 55:45 → 70:30, mobile phase flow rate 8 mL / min) to obtain compound 4 (3.67 mg, t R =8.9min) and compound 35 (9.4mg, t R =6.6min).

[0050] Component A9-31 was separated using Sephadex LH-20 (methanol) to obtain 6 components (denoted as A9-31-1 to A9-31-6).

[0051] Fraction A9-31-6 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 50:50 → 65:35, mobile phase flow rate 8 mL / min) to obtain compound 25 (3.6 mg, t R =7.1min) and compound 39 (4.0mg, t R =7.5min).

[0052] Component A9-30 was separated using Sephadex LH-20 (methanol) to obtain 6 components (denoted as A9-30-1 to A9-30-6).

[0053] Fraction A9-30-5 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 50:50 → 65:35, mobile phase flow rate 8 mL / min) to obtain compound 24 (33.5 mg, t R =7.0min) and compound 28 (102.0mg, t R =7.6min).

[0054] Fraction A9-30-3 was purified to obtain compound 31 (19.2 mg, t). R =6.6min).

[0055] Component A9-29 was separated using Sephadex LH-20 (methanol) to obtain 9 components (denoted as A9-29-1 to A9-29-9).

[0056] Fraction A9-29-9 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 70:30 → 85:15, v / v, mobile phase flow rate 8 mL / min) to obtain compound 2 (13.2 mg, t R =10.1min) and compound 10 (5.9mg, t R =14.9min).

[0057] (4) Separation and purification of component A8 Fraction A8 (6.3 g) was subjected to ODS RP-18 column chromatography with gradient elution using methanol-water as the eluent (methanol to water volume ratios of 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, respectively), yielding 29 fractions (denoted as A8-1 to A8-29).

[0058] Component A8-29 was separated using Sephadex LH-20 (methanol) to obtain four components (denoted as A8-29-1 to A8-29-4).

[0059] Fraction A8-29-4 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 55:45 → 70:30, v / v mobile phase flow rate 8 mL / min) to obtain compound 3 (4.3 mg, t R =13.2min).

[0060] Component A8-28 was separated using Sephadex LH-20 (methanol) to obtain 6 components (denoted as A8-28-1 to A8-28-6).

[0061] Fraction A8-28-6 was purified by semi-preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 50:50 → 70:30, v / v mobile phase flow rate 8 mL / min) to obtain compound 6 (7.0 mg, tR = 17.9 min) and compound 34 (8.5 mg, tR = 17.9 min). R =20.2min).

[0062] Component A8-26 was separated using Sephadex LH-20 (methanol) to obtain 6 components (A8-26-1 to A8-26-6).

[0063] Fraction A8-26-3 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 40:60 → 55:45, v / v, mobile phase flow rate 8 mL / min) to obtain compound 7 (7.12 mg, tR = 6.4 min) and compound 29 (7.39 mg, tR = 6.4 min). R =9.8min) and compound 33 (14.1mg, t R =8.7min).

[0064] Fraction A8-26-5 was purified to obtain compound 32 (5.8 mg, t). R =8.8min) and compound 37 (9.5mg, t R =11.2min).

[0065] (5) Isolation and purification of component A6 Fraction A6 (46g) was subjected to ODS RP-18 column chromatography with gradient elution using methanol-water as the eluent (volume ratios of methanol and water were 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, respectively), yielding 21 fractions (denoted as A6-1 to A6-21).

[0066] After standing, fraction A6-14 was given as a solid (A6-14a), which was washed with methanol-water (50:50). A6-14a was purified by preparative HPLC (0-40 min, acetonitrile and 0.01% formic acid / water volume ratio 60:40→75:25, mobile phase flow rate 8 mL / min) to obtain compound 5 (15.0 mg, t). R =9.5min) and compound 14 (11.0mg, t R =7.9min).

[0067] Component A6-18 was allowed to stand to obtain solid A6-18a and washing solution A6-18b, respectively.

[0068] Fraction A6-18a was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 70:30 → 100:0, mobile phase flow rate 8 mL / min) to obtain compound 11 (10.0 mg, t R =28.0min), compound 15 (9.0mg, t R =26.1min), compound 17 (8.0mg, t R =27.1min) and compound 20 (5.0mg, t R =29.8min).

[0069] Fraction A6-18b was purified to obtain compound 13 (5.0 mg, t). R =21.7min), compound 22 (10.0mg, t R =22.8min) and compound 38 (4.6mg, t R =24.2min).

[0070] Component A6-19 was allowed to stand to obtain solid A6-19a and washing solution A6-19b. Washing solution A6-19b was separated by Sephadex LH-20 (methanol) to obtain 4 components (denoted as A6-19b-1 to A6-19b-4).

[0071] Fraction A6-19b-3 was purified by preparative HPLC (0–40 min, acetonitrile and 0.01 v / v% formic acid aqueous solution volume ratio 60:40 → 90:10, mobile phase flow rate 8 mL / min) to obtain compound 12 (4.0 mg, t R =27.1min), compound 18 (5.3mg, t R =23.3 min) and compound 21 (16.7 mg, tR=24.7 min).

[0072] Fraction A6-19b-3 was purified to give compound 30 (2.5 mg, t). R =23.7min), compound 19 (3.6mg, t R =10min) and compound 36 (2.3mg, t R =18.5min).

[0073] The NMR data of compounds 1–39 were measured in C6D5N, and the results are shown in Tables 1–12.

[0074] Table 1. Compounds 1-6 13 C-NMR nuclear magnetic resonance data

[0075] Note: In Table 1, a represents the test results at 150MHz, and b represents the test results at 125MHz.

[0076] Table 2 Compounds 1-3 1 H-NMR nuclear magnetic resonance data

[0077] Note: In Tables 2-3, a represents the test results at 600MHz, and b represents the test results at 500MHz.

[0078] Compounds 4-6 in Table 31 H-NMR nuclear magnetic resonance data

[0079] Compound 7 in Table 4 1 H-NMR (500MHz) and 13 C-NMR (125MHz) nuclear magnetic resonance data Compound 8: White amorphous powder. Easily soluble in pyridine. Molecular formula C 37 H 56 O8. ESI-MS m / z 627 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.57 (br s, 1H, H-7), 5.37 (d, J = 6.3 Hz, 1H, H-11), 4.95 (br s, 1H, H-31a), 4.93 (br s, 1H, H-3), 4.82 (br s, 1H, H-31b), 4.49 (t, J = 6.9 Hz, 1H, H-16), 2.92 (tt, J = 11.1, 2.8 Hz, 1H, H-20), 2.82 (ddd, J = 11.4, 6.0, 2.2 Hz, 1H, H-17), 1.70 (s, 3H, H-6'), 1.41 (s, 3H, H-30), 1.04(s, 3H, H-18), 1.00 (s, 3H, H-19), 0.97 (ddd, J = 6.8, 4.2, 2.4 Hz, 6H, H-26,H-27), 0.95 (s, 3H, H-29), 0.89 (s, 3H, H-28). 13 C-NMR (150 MHz, C5D5N) is shown in Table 5. Compound 8 was identified as 3- epi -(3'-hydroxy-3'-methylglutaryloxyl)-dehydrotumulosic acid.

[0080] Compound 9: White amorphous powder. Easily soluble in pyridine. Molecular formula C 33 H 50 O5. ESI-MS m / z 525 [MH] - The molecular mass of the compound is 526. 1 H-NMR (600 MHz, C5D5N) δ H 5.58 (d, J = 4.7 Hz, 1H, H-7), 5.37 (d, J = 6.3 Hz, 1H, H-11), 4.98 (br s, 1H, H-3), 4.96 (br s, 1H, H-31a), 4.85 (br s, 1H, H-31b), 4.51 (dd, J = 8.4, 5.9 Hz, 1H, H-16), 2.84 (dd, J = 11.3,5.9 Hz, 1H, H-17), 1.92 (s, 3H, H-2'), 1.37 (s, 3H, H-19), 1.05 (s, 3H, H-18), 1.02 (s, 3H, H-30), 1.00 (brs, 3H, H-27), 0.99 (m, 6H, H-26, H-29) 0.92 (s, 3H, H-28). 13 C-NMR (150 MHz, C5D5N) is shown in Table 5. Compound 9 was identified as 3- epi -dehydropachymicacid.

[0081] Compounds 8-9 in Table 5 13 C-NMR (150MHz) data

[0082] Compound 10: White amorphous powder. Easily soluble in pyridine. Molecular formula C 35 H 52 O7. ESI-MS m / z 583 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.59 (br s, 1H, H-7), 5.39 (d, J = 6.3 Hz, 1H, H-11), 4.99 (br s, 1H, H-31a), 4.88 (br s, 1H, H-3), 4.85 (br s, 1H, H-31b), 4.53 (t,J = 7.1 Hz, 1H, H-16), 3.62 (d, J = 1.7 Hz, 2H, H-2'), 3.61 (s, 3H, H-4'), 1.43 (s, 3H, H-30), 1.06 (s, 3H, H-18), 1.01 (s, 3H, H-19), 1.00 (br s,3H, H-27), 1.01 (br s, 3H, H-26), 0.92 (s, 3H, H-29), 0.90 (s, 3H, H-28). 13 C-NMR (150 MHz, C5D5N) is shown in Table 6. Compound 10 was identified as 3- epi -(3'- O -methyl malonyloxy)-dehydrotumulosic acid.

[0083] Compound 11: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 48 O3. ESI-MS m / z 467 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.63 (d, J = 6.2 Hz, 1H, H-7), 5.38 (d, J = 6.8 Hz,1H, H-11), 4.94 (br s, 1H, H-31a), 4.90 (br s, 1H, H-31b), 3.45 (t, J = 7.8 Hz, 1H, H-3), 2.66 (td, J = 11.1, 3.2 Hz, 1H, H-20), 1.29 (m, 1H, H-5), 1.22 (s,3H, H-29), 1.14 (s, 3H, H-30), 1.07 (br s, 6H, H-19, H-28), 1.04 (s, 3H, H-18), 1.03 (br s, 3H, H-27), 1.02 (br s, 3H, H-26); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 6. Compound 11 was identified as dehydroeburicoic acid.

[0084] Compound 12: White amorphous powder. Easily soluble in pyridine. Molecular formula C 33 H 50 O5. ESI-MS m / z 525 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.58 (t, J = 4.6 Hz, 1H, H-7), 5.32 (d, J = 6.2 Hz,1H, H-11), 4.98 (br s, 1H, H-31a), 4.85 (br s, 1H, H-31b), 4.71 (dd, J = 11.7,4.2 Hz, 1H, H-3), 4.54 (dd, J = 8.4, 5.6 Hz, 1H, H-16), 2.89 (m, 1H, H-17), 2.06 (s, 3H, H-2'), 1.50 (s, 3H, H-30), 1.05 (s, 3H, H-18), 1.01 (d, J = 1.8Hz, 3H, H-26), 0.99 (q, J = 3.9, 3.3 Hz, 9H, H-19, H-28, H-29), 0.90 (s, 3H, H-28).; 13 C-NMR (150 MHz, C5D5N) results are shown in Table 6. Compound 12 was identified as dehydropachymic acid.

[0085] Compound 13: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 48 O4. ESI-MS m / z 483 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.64 (d, J = 7.3 Hz, 1H, H-7), 5.40 (d, J = 7.3 Hz, 1H, H-11), 4.99 (d, J = 9.0 Hz, 1H, H-31a), 4.85 (d, J= 8.9 Hz, 1H, H-31b), 4.55(m, 1H, H-16), 3.46 (d, J = 7.5 Hz, 1H, H-3), 2.71 (m, 1H, H-17), 1.52 (s,3H, H-30), 1.22 (s, 3H, H-18), 1.14 (s, 3H, H-19), 1.09 (s, 3H, H-29), 1.08 (s, 3H, H-28), 1.01 (d, J = 6.0 Hz, 3H, H-27), 0.99 (d, J = 6.0 Hz, 3H, H-26); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 6. Compound 13 was identified as dehydrotumulosic acid.

[0086] Table 6. Compounds 10-13 13 C-NMR (150MHz) data Compound 14: 3-epio-dehydrothomolic acid, white amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 48 O4. 1 H-NMR (600 MHz, C5D5N) δ H : 5.63 (s, 1H, H-7), 5.44 (d, J = 6 Hz, 1H, H-11), 4.98 (s, 1H, H-31), 4.54 (d, J = 6 Hz, 1H, H-16), 3.63 (brs, 1H, H-3), 2.93 (m, 1H, H-20), 2.36 (m, 1H, H-25), 1.44 (s, 3H, H-30), 1.17 (s, 3H, H-28), 1.13 (s, 3H, H-19), 0.96 (m, J = 6.5 Hz, 3H, H-26, H-27), 1.06 (s, 3H, H-18), 0.95 (s, 3H, H-29); 13 C-NMR (150 MHz, C5D5N) δ C See Table 7 for identification of compound 3-table-dehydrotomonic acid.

[0087] Compound 15: White amorphous powder. Easily soluble in pyridine. White amorphous powder. Molecular formula C31 H 46 O4. ESI-MS m / z 481 [MH] - . 1 H-NMR (500 MHz, C5D5N) δ H 5.59 (d, J = 6.7 Hz, 1H, H-7), 5.36(d, J = 6.3 Hz, 1H, H-11), 4.99 (br s, 1H, H-31a), 4.85 (br s, 1H, H-31b), 4.54(dd, J = 8.3, 5.8 Hz, 1H, H-16), 2.96 (td, J = 10.9, 3.2 Hz, 1H, H-20), 2.88 (dd, J = 11.2, 5.9 Hz, 1H, H-17), 1.46 (s, 3H, H-30), 1.13 (s, 6H, H-28, H-18), 1.06 (s, 3H, H-29), 1.06 (s, 3H, H-19), 1.00 (d, J = 3.7 Hz, 3H, H-26), 0.99(d, J = 3.8 Hz, 3H, H-27); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 7. Compound 15 was identified as polyporenic acid C.

[0088] Compound 16:3 β， -16 α -Dihydroxylanost-7,9(11),24-trien-21-acid, white amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O4. 1 H-NMR (600 MHz, C5D5N) δ H 5.64 (d, J = 5.6 Hz, 1H, H-7), 5.38 (d, J = 5.8 Hz, 1H, H-11), 5.33 (d, J = 6.7 Hz, 1H, H-24), 4.53 (m, 1H, H-16), 3.45 (m, 1H, H-3), 2.84 (d,J = 11.0 Hz, 1H, H-20), 2.53 (s, 1H, H-17), 1.62 (4s, 3H, H-26), 1.60 (s, 3H, H-27), 1.50 (s, 3H, H-30), 1.22 (s, 3H, H-28), 1.13 (s, 3H, H-18), 1.04 (s, 3H, H-19), 1.03 (s, 3H, H-29); 13 C-NMR (150 MHz, C5D5N) δ C See Table 7, the identified compound is 3 β -16 α -dihydroxylanosta-7,9(11),24-Trien-21-oicacid.

[0089] Compound 17:16 α 1-Hydroxydehydropyrrolidone, white amorphous powder. Easily soluble in pyridine. Molecular formula: C 30 H 46 O4. 1 H-NMR (600 MHz, C5D5N) δ H : 5.63 (s, 1H, H-7), 5.45 (d, J = 6.2 Hz, 1H, H-24), 5.33 (d, J = 8.3 Hz, 1H, H-11), 4.54 (m, 1H, H-27a), 3.65 (d, J = 16.9Hz, 1H), 2.85 (m, 1H, H-17), 2.74 (d, J = 17.5 Hz, 1H), 1.75 (d, J = 12.8 Hz, 1H, H-26), 1.64 (s, 3H, H-27), 1.63 (s, 3H, H-26), 1.42 (s, 3H, H-30), 1.25 (s, 3H, H-28), 1.12–1.10 (s, 3H, H-19), 1.09 (s, 3H, H-18), 0.95 (s, 3H, H-29); 13 C-NMR (150 MHz, C5D5N) δ C See Table 7, the identified compound is 16. α -Hydroxydehydrosuppuric acid.

[0090] Compound 18: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H46 O5. ESI-MS m / z 485 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.62 (br s, 1H, H-11), 5.59 (br s, 1H, H-7), 5.35 (m, 1H, H-24), 4.91 (s, 1H, H-12), 4.64 (m, 1H, H-16), 3.46 (m, 1H, H-3), 1.61 (br s, 1H, H-26), 1.59 (br s, 3H, H-27), 1.54 (s, 3H, H-30), 1.20(s, 3H, H-28), 1.11 (s, 3H, H-29), 1.10(s, 3H, H-18), 1.08 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) is shown in Table 7. Compound 18 was identified as 3. β ,12 β ,16 α ,-trihydroxy-lanosta-7,9(11),24(25)-triene-21-oic acid.

[0091] Table 7 Compounds 14-18 13 C-NMR (150MHz) data Compound 19: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O5. ESI-MS m / z 485 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.62 (d, J = 6.3 Hz, 1H, H-7), 5.37 (d, J = 6.2 Hz,1H, H-11), 5.34 (m, 1H, H-24), 3.46 (t, J = 7.8 Hz, 1H, H-3), 2.67 (td, J= 11.1,3.2 Hz, 1H, H-20), 2.55 (m, 1H, H-17), 1.67 (s, 3H, H-26), 1.63 (s, 3H, H-27), 1.23 (s, 3H, H-30), 1.14 (s, 3H, H-18), 1.07 (br s, 6H, H-19, H-29),1.01 (s, 3H, H-28).. 13 C-NMR (150 MHz, C5D5N) results are shown in Table 8. Compound 19 was identified as dehydrotrametenolic acid.

[0092] Compound 20: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 48 O3. ESI-MS m / z 455 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.34 (m, 1H, H-24), 3.45 (t, J = 7.1 Hz, 1H, H-3), 2.67 (td, J = 11.2, 3.3 Hz, 1H, H-20), 2.46 (m, 1H, H-17), 1.68 (br s, 3H, H-27), 1.63 (br s, 3H, H-26), 1.26 (s, 3H, H-30), 1.09 (s, 3H, H-18), 1.09 (s,3H, H-19), 1.03 (s, 3H, H-29) 1.02 (s, 3H, H-28); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 8. Compound 20 was identified as trametenolic acid.

[0093] Compound 21: White amorphous powder. Easily soluble in pyridine. Molecular formula C 32 H 50 O5. ESI-MS m / z 513 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.35 (m, 1H, H-24), 4.69 (dt, J= 11.8, 4.1 Hz,1H, H-3), 4.53 (m, 1H, H-16), 2.95 (t, J = 10.9 Hz, 1H, H-20), 2.81 (dt, J =10.4, 4.6 Hz, 1H, H-17), 2.07 (s, 3H, H-2'), 1.62 (br s, 3H, H-27), 1.60 (brs, 3H, H-26), 1.49 (s, 3H, H-30), 1.13 (s, 3H, H-18), 0.96 (s, 3H, H-19), 0.93 (s, 3H, H-29), 0.92 (s, 3H, H-28); 13 C-NMR (150 MHz, C5D5N) is shown in Table 8. Compound 21 was identified as 3. β - O -acetyl-16 α -hydroxy-lanosta-8,24-dien-21-oic acid.

[0094] Compound 22: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 48 O4. ESI-MS m / z : 471 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.32 (m, 1H, H-24), 4.52 (dd, J = 8.3, 5.9 Hz, 1H,H-16), 3.43 (dd, J = 9.1, 6.8 Hz, 1H, H-3), 2.94 (td, J = 10.8, 3.2 Hz, 1H, H-20), 2.79 (dd, J = 11.2, 5.9 Hz, 1H, H-17), 1.60 (br s, 3H, H-27), 1.58 (br s,3H, H-26), 1.47 (s, 3H, H-30), 1.23 (s, 3H, H-18), 1.14 (s, 3H, H-19), 1.06(s, 3H, H-29), 1.01 (s, 3H, H-28); 13C-NMR (150 MHz, C5D5N) is shown in Table 8. Compound 22 was identified as 16. α -hydroxytrametenolic acid.

[0095] Compound 23: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 50 O3. ESI-MS m / z 469 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 4.95 (br s, 1H, H-31a), 4.90 (br s, 1H, H-31b), 3.45 (t, J = 7.8 Hz, 1H, H-3), 2.48 (d, J = 7.3 Hz, 1H, H-17), 2.34 (dd, J = 11.1,5.3 Hz, 1H, H-25), 1.26 (s, 3H, H-29), 1.10 (s, 3H, H-18), 1.09 (s, 3H, H-19), 1.05 (br s, 3H, H-26), 1.04 (br s, 6H, H-28, 30), 1.03 (br s, 3H, H-27); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 8. Compound 23 was identified as eburicoic acid.

[0096] Compounds 19-23 in Table 8 13 C-NMR (150MHz) data Compound 24: White amorphous powder. Easily soluble in pyridine. Molecular formula C 33 H 52 O5. ESI-MS m / z 527 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 4.98 (br s, 1H, H-31a), 4.85 (br s, 1H, H-31b), 4.67 (dd, J= 11.9, 4.3 Hz, 1H, H-3), 4.53 (dd, J = 8.4, 5.7 Hz, 1H, H-16), 2.94(td, J = 11.0, 3.3 Hz, 1H, H-20), 2.82 (dt, J = 11.3, 4.7 Hz, 1H, H-17), 2.28 (m,1H, H-25), 2.06 (s, 3H, H-2'), 1.49 (s, 1H, H-30), 1.13 (s, 3H, H-18), 1.00(d, J = 4.3 Hz, 3H, H-26), 0.99 (d, J = 4.4 Hz, 3H, H-27), 0.96 (s, 3H, H-19), 0.93 (s, 3H, H-29), 0.92 (s, 3H, H-28); 13 C-NMR (150 MHz, C5D5N) results are shown in Table 9. Compound 24 was identified as pachymic acid.

[0097] Compound 25: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 50 O4. ESI-MS m / z 485 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 4.99 (br s, 1H, H-31a), 4.85 (br s, 1H, H-31b), 4.54 (dd, J = 8.3, 5.9 Hz, 1H, H-16), 3.45 (dd, J = 9.1, 6.9 Hz, 1H, H-3), 2.95(td, J = 10.9, 3.2 Hz, 1H, H-20), 2.83 (dd, J= 11.2, 5.9 Hz, 1H, H-17), 2.28 (m,1H, H-25), 1.49 (s, 3H, H-30), 1.24 (s, 3H, H-18), 1.16 (s, 3H, H-19), 1.08(s, 3H, H-29), 1.03 (s, 3H, H-28), 1.00 (d, J = 4.5 Hz, 3H, H-27), 0.98 (d, J =4.6 Hz, 3H, H-26). 13 C-NMR (150 MHz, C5D5N) results are shown in Table 9. Compound 25 was identified as tumulosic acid.

[0098] Compound 26: White amorphous powder. Easily soluble in pyridine. Molecular formula C 32 H 48 O6. ESI-MS m / z 527 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.49 (br s, 1H, H-31a), 5.29 (br s, 1H, H-11), 5.27 (d, J = 3.9 Hz, 1H, H-31b), 5.17 (br s, 1H, H-7), 4.81 (d, J = 2.5 Hz, 1H, H-28a), 4.76 (m, 1H, H-28b), 4.54 (t, J = 7.2 Hz, 1H, H-16), 3.62 (s, 3H, H-1'), 3.01 (s, 1H, H-20), 2.89 (dd, J = 11.2, 5.9 Hz, 1H, H-17), 2.27 (d, J = 7.5Hz, 1H, H-5), 1.71 (s, 3H, H-29), 1.55 (s, 3H, H-26), 1.55 (s, 3H, H-27), 1.43 (s, 3H, H-30), 1.07 (s, 3H, H-18), 0.96 (s, 3H, H-19). 13C-NMR (150 MHz, C5D5N) results are shown in Table 9. Compound 26 was identified as poricoic acid DM.

[0099] Compound 27: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 46 O6. ESI-MS m / z 513 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.48 (br s, 1H, H-31a), 5.33 (d, J = 5.1 Hz, 1H,H-11), 5.29 (d, J = 3.9 Hz, 1H, H-7), 5.16 (br s, 1H, H-31b), 4.83 (d, J = 2.9Hz, 1H, H-28a), 4.76 (d, J = 2.7 Hz, 1H, H-28b), 4.53 (dd, J = 8.4, 6.1 Hz, 1H,H-16), 3.01 (m, 1H, H-20), 2.89 (ddd, J = 10.8, 6.0, 2.7 Hz, 1H, H-17), 2.34(d, J = 7.3 Hz, 1H, H-5), 1.73 (s, 3H, H-29), 1.55 (s, 3H, H-27), 1.54 (s, 3H,H-26), 1.49 (s, 3H, H-30), 1.09 (s, 3H, H-18), 1.03 (s, 3H, H-19). 13 C-NMR (150MHz, C5D5N) δ C See Table 9. Compound 27 was identified as poricoic acid D.

[0100] Compound 28: White amorphous powder. Easily soluble in pyridine. Molecular formula C 31 H 46 O7. ESI-MS m / z 529 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.60 (br s, 1H, H-31a), 5.33 (d, J = 4.6 Hz, 1H,H-31b), 5.32 (br s, 1H, H-11), 5.28 (d, J = 3.8 Hz, 1H, H-7), 4.83 (br s, 1H,H-28a), 4.77 (br s, 1H, H-28b), 4.53 (t, J = 7.4 Hz, 1H, H-16), 1.74 (s, 3H, H-29), 1.66 (s, 3H, H-27), 1.49 (s, 3H, H-30), 1.08 (s, 3H, H-18), 1.03 (s, 3H,H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 9. Compound 28 was identified as poricoic acid L.

[0101] Compounds 24-28 in Table 9 13 C-NMR (150MHz) data Compound 29: White amorphous powder. Easily soluble in pyridine. Molecular formula C 32 H 48 O5. ESI-MS m / z 511 [MH] - . 1 H-NMR (500 MHz, C5D5N) δ H : 5.29 (m, 1H, H-11), 5.27 (d, J = 3.4 Hz, 1H, H-7), 4.98 (br s, 1H, H-31a), 4.85 (d, J = 1.4 Hz, 1H, H-31b), 4.81 (d, J = 2.6 Hz, 1H,H-28a), 4.76 (dd, J = 2.7, 1.5 Hz, 1H, H-28b), 4.52 (dd, J = 8.3, 6.0 Hz, 1H, H-16), 3.62 (s, 3H, H-32), 2.95 (td, J= 10.9, 3.2 Hz, 1H, H-20), 2.86 (dd, J =11.2, 6.0 Hz, 1H, H-17), 1.72 (s, 3H, H-29), 1.43 (s, 3H, H-30), 1.09 (s, 3H,H-18), 1.00 (d, J = 3.6 Hz, 3H, H-26), 0.98 (d, J = 3.7 Hz, 3H, H-27), 0.96 (s, 3H, H-19); 13 C-NMR (150 MHz, C5D5N) δ C See Table 10. Compound 29 was identified as poricoic acid AM.

[0102] Compound 30: Yellow powder. Easily soluble in pyridine. Molecular formula C 30 H 44 O5. ESI-MS m / z 483 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.32 (d, J = 6.2 Hz, 1H, H-11), 5.27 (d, J = 4.0 Hz, 1H, H-7), 4.81 (d, J = 2.6 Hz, 1H, H-28a), 4.74 (br s, 1H, H-28b), 4.50 (t, J = 7.2 Hz, 1H, H-16), 2.91 (d, J = 11.9 Hz, 1H, H-20), 2.83 (dd, J = 11.2, 5.9 Hz, 1H, H-17), 2.33 (t, J = 8.2 Hz, 1H, H-5), 1.71 (s, 3H, H-29), 1.59 (br s, 3H, H-26),1.57 (br s, 3H, H-27), 1.47 (s, 3H, H-30), 1.07 (s, 3H, H-18), 1.01 (s, 3H,H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 10. Compound 30 was identified as poricoic acid B.

[0103] Compound 31: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 44 O5. ESI-MS m / z 499 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.45 (d, J = 7.3 Hz, 1H, H-24), 5.30 (d, J = 7.7 Hz, 1H, H-11), 5.26 (d, J = 8.8 Hz, 1H, H-7), 4.81 (br s, 1H, H-28a), 4.75 (br s,1H, H-28b), 4.51 (d, J = 11.9 Hz, 1H, H-27a), 4.47 (m, 3H, H-16), 4.42 (d, J =11.6 Hz, 1H, H-27b), 1.95 (s, 3H, H-26), 1.71 (s, 3H, H-29), 1.46 (s, 3H, H-30). 1.06 (s, 3H, H-18), 1.03 (s, 3H, H-19), 13 C-NMR (150 MHz, C5D5N) δ C See Table 10. Compound 31 was identified as poricoic acid E.

[0104] Compound 32: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 44 O6. ESI-MS m / z 499 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.34 (br s, H, H-11), 5.28 (br s, 1H, H-7), 4.83 (br s, 1H, H-28a), 4.77 (br s, 1H, H-28b), 4.51 (t,J = 7.4 Hz, 1H, H-16), 4.26(d, J = 3.4 Hz, 2H, H-29), 2.96 (m, 1H, H-20), 2.85 (m, 1H, H-17), 2.34 (d, J =7.0 Hz, 1H, H-5), 1.81 (br s, 3H, H-27), 1.74 (d, J = 3.5 Hz, 3H, H-26), 1.49(s, 3H, H-30), 1.07 (s, 3H, H-18), 1.03 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 10. Compound 32 was identified as poricoic acid ZC.

[0105] Compound 33: White amorphous powder. Easily soluble in pyridine. Molecular formula C 35 H 52 O7. ESI-MS m / z 583 [MH] - . 1 H-NMR (400 MHz, C5D5N) δ H :5.32 (br s, 1H, H-11), 5.25 (br s, 1H, H-7), 4.83(d, J = 2.6 Hz, 1H, H-28a), 4.77 (br s, 1H, H-28b), 4.63 (d, J = 11.9 Hz, 1H, H-31a), 4.57 (d, J = 12.2 Hz, 1H, H-31b), 4.54 (m, 1H, H-16), 4.51 (br s, 2H, H-26), 2.99 (m, 1H, H-20), 2.88 (m, 1H, H-17), 2.10 (s, 3H, H-27), 1.73 (s, 3H, H-29), 1.50 (s, 3H, H-30), 1.08 (s, 3H, H-18), 1.04 (s, 3H, H-19). 13 C-NMR (150MHz, C5D5N) results are shown in Table 10. Compound 33 was identified as poricoic acid J.

[0106] Table 10 Compounds 29-33 13 C-NMR (150MHz) data Compound 34: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O6. ESI-MS m / z 501 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.34 (br s, 1H, H-11), 5.29 (m, 1H, H-7), 4.82 (br s, 1H, H-28a), 4.76 (br s, 1H, H-28b), 4.50 (t, J = 9.5 Hz, 1H, H-16), 1.75(s, 3H, H-29), 1.49 (s, 3H, H-30), 1.36 (s, 6H, H-26, 27), 1.09 (s, 3H, H-18), 1.03 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) results are shown in Table 11. Compound 34 was identified as poricoicacid ZG.

[0107] Compound 35: White amorphous powder. Easily soluble in pyridine. Molecular formula C 32 H 50 O7. ESI-MS m / z 545 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H 5.30 (br s, 1H, H-7), 5.24 (br s, 1H, H-11), 4.80(d, J = 2.6 Hz, 1H, H-28a), 4.73 (br s, 1H, H-28b), 4.47 (t, J = 7.1 Hz, 1H, H-16), 4.29 (d, J= 4.4 Hz, 2H), 2.91 (m, 1H, H-20), 2.88 (m, 1H, H-17)1.70 (s,3H, H-29), 1.61 (s, 3H, H-27), 1.57 (s, 3H, H-26), 1.46 (s, 3H, H-30), 1.02(s, 3H, H-18), 1.00 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 11. Compound 35 was identified as poricoic acid N.

[0108] Compound 36: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O7. ESI-MS m / z 517 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.33 (brs, 1H, H-11), 5.27 (br s, 1H, H-7), 4.83(br s, 1H, H-28a), 4.77 (br s, 1H, H-28b), 4.53 (m, 1H, H-16), 3.84 (m, 1H,H-24), 1.73 (s, 3H, H-29), 1.49 (s, 6H, H-27, 30), 1.45 (s, 3H, H-26), 1.07 (s, 3H, H-18), 1.03 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 11. Compound 36 was identified as poricoic acid M.

[0109] Table 11 Compounds 34-36 13 C-NMR (150MHz) data Compound 37: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O6. ESI-MS m / z 501 [MH] - . 1H-NMR (600 MHz, C5D5N) δ H : 5.49 (t, J = 6.9 Hz, 1H, H-24), 5.00 (br s, 1H, H-28a), 4.90 (br s, 1H, H-28b), 4.53 (d, J = 12.2 Hz, 1H, H-27a), 4.48 (d, J = 7.3Hz, 1H, H-16), 4.44 (d, J = 12.2 Hz, 1H, H-27b), 2.93 (t, J = 11.2 Hz, 1H, H-20),2.79 (dd, J = 11.2, 5.8 Hz, 1H, H-17), 2.32 (d, J = 12.9 Hz, 1H, H-5), 1.97 (s,3H, H-26), 1.80 (s, 3H, H-29), 1.50 (s, 3H, H-30), 1.14 (s, 3H, H-18), 0.96(s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N) δ C See Table 12. Compound 37 was identified as 16. α ,27-dihydroxy-3,4-secolanosta-4(28),8(9),24-triene-3,21-dioic acid.

[0110] Compound 38: White amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O6. ESI-MS m / z 501 [MH] - . 1 H-NMR (600 MHz, C5D5N) δ H : 5.75 (br s, 1H, H-28a), 5.35 (d, J= 8.6 Hz, 1H,H-24), 5.15 (br s, 1H, H-28b), 4.48 (m, 1H, H-16), 1.62 (s, 3H, H-27), 1.60(s, 3H, H-26), 1.48 (s, 3H, H-30), 1.17 (s, 3H, H-18), 1.05 (s, 3H, H-19). 13 C-NMR (150 MHz, C5D5N); 13 C-NMR (150 MHz, C5D5N) δ C See Table 12. Compound 38 was identified as poricoicacid ZM.

[0111] Compound 39: poricoic acid G, white amorphous powder. Easily soluble in pyridine. Molecular formula C 30 H 46 O5. 1 H-NMR (600 MHz, C5D5N) δ H : 5.35 (brs, 1H, H-24), 5.00 (s, 1H, H-28b), 4.90 (s, 1H, H-28a), 4.52 (brs, 1H, H-16), 2.93 (m, 1H, H-20), 2.82 (m, 1H, H-17), 2.70 (m, 1H, H-2b), 2.48 (m, 1H, H-23b), 2.46 (m, 1H, H-23a), 1.80 (brs, 3H, H-29), 1.62 (d, J = 3.8 Hz, 3H, H-26), 1.60 (d, J = 4.1 Hz, 3H, H-27), 1.50 (d, J = 4.1 Hz, 3H, H-30), 1.16 (d, J = 4.1 Hz, 3H, H-18), 0.96 (d, J = 4.1 Hz, 3H, H-19); 13 C-NMR (150 MHz, C5D5N) δ C See Table 12 for identification of compound poricoic acid G.

[0112] Table 12 Compounds 37-39 13 C-NMR (150MHz) data Test Example 1 Whitening performance test Experimental materials and instruments: Arbutin (batch number: K621084) and α-MSH (batch number: K372809) were purchased from Kekulé (Guangzhou) Biomedical Co., Ltd.; NaOH (batch number: 1310732, Damao Chemical Reagent Co., Ltd.), fluorescence inverted microscope (model: D-35578 Wetzlar, Leica, Germany), multifunctional microplate reader (model: Spectra Max i3X, Bio-Tek, USA), low-temperature centrifuge (model: LX-165T2R, Haier, China); clean bench (model: SW-CJ-2FD, Suzhou Purification Equipment Co., Ltd.); carbon dioxide cell incubator (model: Zcqr-1150, Shanghai Zhicheng Analytical Instrument Manufacturing Co., Ltd.).

[0113] Cell culture: Cells were cultured in 1640 medium containing 10% fetal bovine serum and 100 U / mL penicillin-streptomycin solution, and placed in a 37°C, 5% CO2 cell culture incubator. When the cells reached 90% confluence, they were digested with trypsin containing 0.25% EDTA and passaged.

[0114] Cell seeding: B16F10 cells were seeded in 6-well plates with 2 mL of DMEM medium containing 10% fetal bovine serum and 100 U / mL penicillin-streptomycin solution and cultured for 24 h per well.

[0115] 1. Relative melanin content in B16F10 cell supernatant and intracellular fluid under α-MSH stimulation Drugs: Compounds 1-39, positive drug arbutin.

[0116] Experimental groups: blank group, α-MSH (concentration of 100 nmol / L) group, and drug treatment group (α-MSH + drug) group. In the drug treatment group, the concentration of α-MSH was 100 nmol / L and the concentration of drug was 50 µmol / L. Each treatment had 3 replicates.

[0117] Melanin content in supernatant: After culturing at 37℃ for 72h, the cell supernatant was aspirated and transferred into a 96-well plate, 100μL per well. The absorbance was measured at a wavelength of 405nm. The blank group was used as a control. The relative melanin content in the cells of each group was compared. The formula for calculating the melanin content is shown in Equation 1. The experimental results are shown in Table 13.

[0118] Intracellular melanin content: The NaOH lysis method was used. After culturing at 37℃ for 72 h, the cells were washed twice with PBS solution, digested with trypsin, centrifuged at 900 r / min for 4 min, and collected in centrifuge tubes. 400 μL of 1 mol / L NaOH solution containing 10 v / v% dimethyl sulfoxide was added to each sample to lyse the cells. The cells were incubated at 80℃ in the dark for 2 h, and then transferred to 96-well plates, 100 μL per well. The absorbance was measured at 405 nm. The blank group was used as a control. The relative melanin content in the cells of each group was compared. The formula for calculating the melanin content is shown in Equation 1. The experimental results are shown in Table 14.

[0119] Formula 1.

[0120] In Formula 1, the drug treatment groups include the α-MSH group, the α-MSH+arbutin group, and the α-MSH+compound group.

[0121] Data processing: Each sample was measured in triplicate, and the result was the average of the three parallel measurements. GraphPad Prism 9 statistical software was used for data analysis, and the values ​​were expressed as mean ± standard deviation. (mean ± standard deviation) indicates the mean. One-way ANOVA was used for comparisons among multiple groups. P < 0.05 was considered statistically significant.

[0122] Table 13 shows the relative melanin content in the supernatant of B16F10 cells stimulated by compounds 1-39.

[0123] Note: Compared to the model group .

[0124] As shown in Table 13, compared with the model group and the blank group, at a molar concentration of 50 µmol / L, the melanin content in the supernatant of compounds 2, 14, 17, 5, 23, and 35 were 66.26%, 71.70%, 81.04%, 74.31%, 73.26%, and 84.01%, respectively. This indicates that compounds 2, 14, 17, 5, 23, and 35 significantly inhibited melanin secretion in B16F10 cells stimulated by α-MSH and had a whitening effect.

[0125] Table 14 shows the relative melanin content in B16F10 cells stimulated by compounds 1-39.

[0126] Note: Compared to the model group .

[0127] As shown in Table 14, compared with the model group and the blank group, at a molar concentration of 50 µmol / L, the intracellular melanin contents of compounds 2, 14, 17, 5, 23, and 35 were 52.11%, 42.47%, 36.68%, 65.34%, 37.13%, and 66.56%, respectively. This indicates that compounds 2, 14, 17, 5, 23, and 35 have a significant inhibitory effect on melanin production in B16F10 cells stimulated by α-MSH and have whitening activity.

[0128] 2. Effects of compound concentration on melanin content in B16F10 cells stimulated by α-MSH Drugs: Compounds 14, 17, 23 and 35, and the positive control drug arbutin.

[0129] Experimental groups: blank group, α-MSH (100 nmol / L) group, and drug-treated group (α-MSH + drug). In the drug-treated group, the α-MSH concentration was 100 nmol / L, and the drug concentrations were 6.25 µmol / L, 12.5 µmol / L, 25 µmol / L, and 50 µmol / L, respectively. Each treatment had three replicates.

[0130] The results are shown in Tables 15-18.

[0131] Table 15 Effects of compound 14 on the relative melanin content in B16F10 cells stimulated by α-MSH.

[0132] Note: Compared to the model group .

[0133] Table 16 shows the effect of compound 17 on the relative melanin content in B16F10 cells stimulated by α-MSH.

[0134] Note: Compared to the model group .

[0135] Table 17 Effects of compound 23 on the relative melanin content in B16F10 cells stimulated by α-MSH

[0136] Note: Compared to the model group .

[0137] Table 18 Effects of compound 35 on the relative melanin content in B16F10 cells stimulated by α-MSH

[0138] Note: Compared to the model group .

[0139] As shown in Tables 15-18, compound 23 exhibited a concentration-dependent inhibitory effect on melanin production in B16F10 cells stimulated by α-MSH within the concentration range of 6.25 µmol / L to 50 µmol / L. Compounds 14 and 17 showed the strongest inhibitory effect at 50 µmol / L. Compound 35 achieved its maximum inhibitory effect on melanin production in B16F10 cells stimulated by α-MSH at a concentration of 6.25 µmol / L.

[0140] 3. Intracellular tyrosinase activity test Drugs: Compounds 2, 5, 14, 17, 23 and 35, and the positive drug arbutin.

[0141] Experimental groups: blank group, α-MSH (100 nmol / L) group, and drug-treated group (α-MSH + drug) group. In the drug-treated group, the α-MSH concentration was 100 nmol / L, and the drug concentrations were 6.25 µmol / L, 12.5 µmol / L, 25 µmol / L, and 50 µmol / L, respectively.

[0142] Enzyme crude extract extraction: After culturing at 37℃ for 72h, the cells were washed twice with PBS solution, digested with trypsin, centrifuged at 900r / min for 4min and collected in a centrifuge tube. 200μL of extraction solution was added, and the cells were sonicated on ice at 200W for 3s with 10s intervals, repeated 30 times. The cells were then centrifuged at 4℃ and 1200g for 20min, and the supernatant was placed on ice for analysis.

[0143] Protein concentration determination: Prepare BCA working solution (A:B=50:1) according to the sample volume and place on ice. Dilute 10 μL of BCA standard with PBS to 100 μL, making the final concentration 0.5 mg / mL. Add 0 μL, 2 μL, 4 μL, 6 μL, 8 μL, 12 μL, 16 μL, and 20 μL of the standard to the protein standard wells of a 96-well plate, and add PBS to bring the total to 20 μL. Dilute the crude extract appropriately and add 20 μL to the sample wells. Add 200 μL of BCA working solution to each well and incubate at 37°C for 30 min. Measure the OD value at 562 nm using a microplate reader, and calculate the protein concentration based on the standard curve.

[0144] Tyrosinase activity assay: The protein content in the solution was determined using the BCA kit. The protein concentrations of each group were adjusted to the same level. 20 μL of the extract was taken and 180 μL of reagent 1 was added. The mixture was thoroughly mixed and timing was started. The OD value at 475 nm was measured at 10 s and recorded as A1. After incubation at 37℃ for 180 s, the OD value at 475 nm was measured at 190 s and recorded as A2. ΔA = A2 - A1. The formula for calculating the relative activity of intracellular tyrosinase is shown in Equation 2.

[0145] Equation 2.

[0146] Data processing: Each sample was measured in triplicate, and the result was the average of the three parallel measurements. GraphPad Prism 9 statistical software was used for data analysis, and the values ​​were expressed as mean ± standard deviation. (mean ± standard deviation) indicates the mean. One-way ANOVA was used for comparisons among multiple groups. P < 0.05 was considered statistically significant. Results are shown in Tables 19-24.

[0147] Table 19 Effects of Compound 2 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH

[0148] Note: Compared with the blank group, ## P<0.001; compared with the model group, .

[0149] Table 20 Effects of compound 5 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH.

[0150] Note: Compared with the blank group, ### P < 0.0001; compared with the model group, .

[0151] Table 21 Effects of compound 14 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH.

[0152] Note: Compared to the model group .

[0153] Table 22 Effects of compound 17 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH

[0154] Note: Compared to the model group .

[0155] Table 23 Effects of compound 23 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH

[0156] Note: Compared to the model group .

[0157] Table 24 Effects of compound 35 on the relative activity of intracellular tyrosinase in B16F10 cells stimulated by α-MSH.

[0158] Note: Compared to the model group .

[0159] As shown in Tables 19-24, the intracellular tyrosinase activity in the blank control group was 100%, while that in the α-MSH group was 126.80%. Compounds 2, 5, 14, 17, 23, and 35, at concentrations ranging from 6.25 to 50 µmol / L, all inhibited the intracellular tyrosinase activity in B16F10 cells stimulated by α-MSH, with the best inhibitory effect observed at 50 µmol / L. The relative intracellular tyrosinase activity ranged from 74.12% to 99.14%, indicating that the triterpene acid compounds provided in this invention can inhibit the intracellular tyrosinase activity in B16F10 cells stimulated by α-MSH and have excellent whitening effects.

[0160] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A triterpenic acid compound, characterized in that, Includes any one of compounds 2-3: ； Compound 2: R1 is -H, R2 is R3 is -H.

2. A method for extracting triterpenoid compounds, characterized in that, Includes the following steps: Poria cocos powder was extracted with methanol-water to obtain a crude methanol extract. The crude methanol extract was subjected to silica gel column chromatography to obtain components A6, A8, and A9, respectively. The volume fraction of methanol in the methanol-water mixture was 95-100%. The silica gel column chromatography was performed using dichloromethane-methanol as the eluent for a first gradient elution, with a volume ratio of dichloromethane to methanol of 100:0 to 0:100 during the first gradient elution. (a) Extraction methods for compounds 1, 2 and 4 The component A9 was subjected to ODS RP-18 column chromatography to obtain components A9-29, A9-32, and A9-33, respectively; the ODS RP-18 column chromatography was performed by second-gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the second-gradient elution was 20:80 to 100:

0. The extraction method of compound 1 includes the following steps: separating component A9-33 using Sephadex LH-20 to obtain component A9-33-8, and purifying component A9-33-8 using preparative HPLC to obtain compound 1; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is third gradient elution, and the volume ratio of mobile phase A to mobile phase B during the third gradient elution process is 65:35~80:20; The extraction method of compound 2 includes the following steps: separating component A9-29 using Sephadex LH-20 to obtain component A9-29-9, and purifying component A9-29-9 using preparative HPLC to obtain compound 2; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fourth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fourth gradient elution process is 70:30~85:15; The extraction method of compound 4 includes the following steps: separating component A9-32 using Sephadex LH-20 to obtain component A9-32-5, and purifying component A9-32-5 using preparative HPLC to obtain compound 4; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is fifth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the fifth gradient elution is 55:45~70:30; (b) Extraction methods for compounds 3, 6 and 7 The component A8 was subjected to ODS RP-18 column chromatography to obtain components A8-26, A8-28 and A8-29, respectively; the ODS RP-18 column chromatography was performed by a sixth gradient elution with methanol-water as the eluent, and the volume ratio of methanol to water during the sixth gradient elution was 20:80~100:

0. The extraction method of compound 3 includes the following steps: separating component A8-29 using Sephadex LH-20 to obtain component A8-29-4, and purifying component A8-29-4 using preparative HPLC to obtain compound 3; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is seventh gradient elution, and the volume ratio of mobile phase A to mobile phase B during the seventh gradient elution is 55:45~70:30; The extraction method of compound 6 includes the following steps: separating component A8-28 using Sephadex LH-20 to obtain component A8-28-6; purifying component A8-28-6 using semi-preparative HPLC to obtain compound 6; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the semi-preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is eighth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the eighth gradient elution is 50:50~70:30; The extraction method of compound 7 includes the following steps: separating component A8-26 using Sephadex LH-20 to obtain component A8-26-3, and purifying component A8-26-3 using preparative HPLC to obtain compound 7; the eluent used in the Sephadex LH-20 separation is methanol; the conditions for the preparative HPLC purification include: mobile phase A is acetonitrile, mobile phase B is 0.01~0.5 v / v% formic acid aqueous solution, the elution method is the ninth gradient elution, and the volume ratio of mobile phase A to mobile phase B during the ninth gradient elution is 40:60~55:45; (c) The extraction method for compound 5 includes the following steps: The component A6 was subjected to ODS RP-18 column chromatography to obtain component A6-14; the ODS RP-18 column chromatography was performed by elution with methanol-water as the eluent in a tenth gradient, and the volume ratio of methanol to water in the tenth gradient elution process was 20:80~100:

0. The component A6-14 was allowed to stand in methanol to precipitate a solid. The obtained solid was washed with an aqueous methanol solution to obtain solid A6-14a. The solid A6-14a was then purified by preparative HPLC to obtain compound 5. The conditions for the preparative HPLC purification included: mobile phase A was acetonitrile, mobile phase B was 0.01~0.5 v / v% formic acid aqueous solution, and the eleventh gradient elution method was used. The volume ratio of mobile phase A to mobile phase B during the eleventh gradient elution was 60:40~75:

25. ； Compound 1: R1 is -OH, R2 is -H, R3 is -OH; Compound 2: R1 is -H, R2 is R3 is -H; Compound 4: R4 is ; Compound 5: R4 is ; Compound 6: R4 is .

3. The extraction method according to claim 2, characterized in that, During the first gradient elution process, the volume ratios of dichloromethane and methanol were 100:0, 50:1, 25:1, 15:1, 10:1, 6:1, 3:1, 1:1 and 0:100, respectively.

4. The extraction method according to claim 2, characterized in that, The volume ratios of methanol and water during the second gradient elution process were 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, and 100:0, respectively. The elution program for the third gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 65:35 to 80:20; The elution program for the fourth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 70:30 to 85:15; The elution program for the fifth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:

30.

5. The extraction method according to claim 2, characterized in that, The volume ratios of methanol and water in the sixth gradient elution process are 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, respectively. The elution program for the seventh gradient is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 55:45 to 70:30; The elution program for the eighth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A and mobile phase B changes linearly from 50:50 to 70:30; The elution program for the ninth gradient elution is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 40:60 to 55:

45.

6. The extraction method according to claim 2, characterized in that, The volume ratios of methanol and water in the tenth gradient elution process are 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0, respectively. The eleventh gradient elution program is as follows: 0~40 min, the volume ratio of mobile phase A to mobile phase B changes linearly from 60:40 to 75:

25.

7. The use of triterpene acid compounds in the preparation of skin-whitening and spot-fading drugs or in skin-whitening and spot-fading daily chemical products, wherein the triterpene acid compounds include at least one of compounds 2-3, 8, 10, and 15, wherein, Compounds 2-3 are the triterpenoid compounds as described in claim 1; Among them, compound 8: R5 is β-OA, and R6 is -OH; Compound 10: R5 is β-OA', R6 is -OH; Where A in β-OA is ;A' in β-OA' is .

8. A pharmaceutical composition, characterized in that, It includes an active ingredient and pharmaceutically acceptable excipients, said active ingredient including triterpenoids, said triterpenoids including at least one of compounds 2-3 in the application of claim 7.

9. A whitening and spot-fading daily chemical product, characterized in that, It includes whitening active ingredients and excipients acceptable in the daily chemical industry, wherein the whitening active ingredients include triterpenoid compounds, and the triterpenoid compounds include at least one of compounds 2-3, 8, 10 and 15 in the application described in claim 7.

10. The whitening and spot-fading daily chemical product according to claim 9, characterized in that, The excipients acceptable in the daily chemical industry include at least one of solvents, humectants, thickeners, pH adjusters, oils, emulsifiers, skin conditioning agents, antioxidants, and chelating agents.

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