3, 7-cembradien-2, 11, 12-triol-6-O-beta-D-glucoside as well as preparation method and application of 3, 7-cembradien-2, 11, 12-triol-6-O-beta-D-glucoside

Abstract

The invention relates to 3, 7-cembradiene-2, 11, 12-triol-6-O-beta-D-glucoside as well as a preparation method and application of the 3, 7-cembradiene-2, 11, 12-triol-6-O-beta-D-glucoside, and the structural formula of the 3, 7-cembradiene-2, 11, 12-triol-6-O-beta-D-glucoside is as shown in a formula I in the specification. The cembrane type diterpenoid glycoside with a novel structure is creatively separated and purified from tobacco raw materials, and the compound can effectively protect glutamic acid induced neuron-like PC12 cell injury and has the potential of being developed into drugs for preventing and / or treating neurodegenerative diseases. The preparation process of the 3, 7-cembradiene-2, 11, 12-triol-6-O-beta-D-glucoside, provided by the invention, is simple in operation steps, easy to control, suitable for large-scale production, and green and environment-friendly, and the filler and the solvent used for extraction and separation can be recycled.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of extraction and separation of active ingredients of secondary metabolism of herbal plants, and relates to 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside and a preparation method and application thereof. BACKGROUND

[0002] Cedrane diterpene is a macrocyclic diterpene formed by connecting four isoprene units at the head and tail, and a three-symmetrical methyl and an isopropyl are distributed on the fourteen-membered ring parent skeleton. The substance is the most abundant and structurally richest diterpene component in nature, is mostly found in soft corals, and is also reported in tobacco and frankincense, and has pharmacological activities such as cytotoxicity, antibacterial activity and liver protection.

[0003] The structure of cedrane diterpene often contains a hydroxyl group, which is easy to combine with sugar to form a glycoside from the structure. However, so far, the eight reported cedrane diterpene glycosides are only distributed in soft corals, Central Asian Sabina and sand grass, and the component has not been found in tobacco raw materials.

[0004] Tobacco is not only rich in resources, has high biological yield and low production cost, therefore, further tapping the cedrane diterpene resources of tobacco, finding new cedrane diterpene compounds and studying the pharmacological activities of the compounds not only promote the development and utilization of natural medicines, but also expand the role of tobacco in the field of human health and improve the comprehensive utilization value of tobacco. SUMMARY

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside and a preparation method and application thereof.

[0006] In order to achieve the purpose of the present application, the following technical solutions are adopted:

[0007] In the first aspect, the present application provides 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside, and the structural formula of the 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside is shown as formula I:

[0008] .

[0009] The present application creatively separates and purifies a novel structure of cedrane diterpene glycoside from tobacco raw materials, the compound can effectively protect glutamic acid-induced PC12 cell damage, and has the potential to develop into a drug for preventing and / or treating neurodegenerative diseases.

[0010] In a second aspect, the present application provides a preparation method of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside according to the first aspect, the preparation method comprising the following steps:

[0011] (1) subjecting a tobacco raw material to alcohol extraction or water extraction to obtain an extraction liquid, concentrating the extraction liquid to obtain an extract, dissolving the extract with water, and then successively extracting with a non-polar solvent and a polar solvent to obtain an extraction liquid;

[0012] (2) concentrating the extraction liquid to obtain an extract, dissolving the extract with water, and then purifying by elution with a macroporous adsorption resin to obtain a crude extract;

[0013] (3) purifying the crude extract by preparative liquid chromatography to obtain the 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside.

[0014] The preparation method of the above specific steps can effectively prepare the above cedrane-type diterpene glycoside compound. The preparation process of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside involved in the present application has simple and easy-to-control operation steps, is suitable for large-scale production, and the fillers and solvents used for extraction and separation can be recycled and used, which is green and environmentally friendly.

[0015] Preferably, the tobacco raw material comprises any one or a combination of at least two of tobacco leaves, tobacco sheets, tobacco shreds, or tobacco powder.

[0016] Preferably, the solvent used in the alcohol extraction comprises anhydrous methanol, anhydrous ethanol, a methanol aqueous solution, or an ethanol aqueous solution.

[0017] Preferably, the alcohol extraction or water extraction method comprises any one or a combination of at least two of soaking extraction, heating reflux extraction, or ultrasonic extraction.

[0018] Preferably, in the alcohol extraction or water extraction, the solid-liquid ratio of the tobacco raw material to the extraction solvent is 1:(100-1000) g / L, such as 100 g / L, 200 g / L, 300 g / L, 400 g / L, 500 g / L, 600 g / L, 700 g / L, 800 g / L, 900 g / L, 1000 g / L, and the like. Other specific point values in this numerical range can also be selected, which will not be repeated here.

[0019] Preferably, the non-polar solvent comprises petroleum ether and / or n-hexane.

[0020] Preferably, the polar solvent comprises any one or a combination of at least two of ethyl acetate, n-butanol, or sec-butanol.

[0021] Preferably, the macroporous adsorption resin is selected from any one or a combination of at least two of HP-20, SP-700, D-101, XAD-2 or XAD-15 resin.

[0022] Preferably, the step of eluting and purifying the macroporous adsorption resin is eluted with water until colorless, then eluted with 10-20% (e.g. 10%, 12%, 13%, 14%, 15%, 17%, 18%, 20%, etc.) alcohol solution until colorless, and the 10-20% alcohol eluate is collected. Other specific point values in the range not listed can be selected, which will not be repeated here.

[0023] Preferably, the chromatographic column of the preparative liquid chromatography is a C18 preparative column.

[0024] Preferably, the C18 preparative column is an XBridge BEH C18 preparative column.

[0025] Preferably, the C18 preparative column has a specification of 250x10 mm, 5 μm.

[0026] Preferably, the mobile phase of the preparative liquid chromatography is an acetonitrile aqueous solution.

[0027] Preferably, the volume fraction of acetonitrile in the acetonitrile aqueous solution is 15-30%, such as 15%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, etc. Other specific point values in the range not listed can be selected, which will not be repeated here.

[0028] Preferably, the flow rate of the mobile phase of the preparative liquid chromatography is 3-5 mL / min, such as 3 mL / min, 3.5 mL / min, 4 mL / min, 4.5 mL / min, 5 mL / min, etc. Other specific point values in the range not listed can be selected, which will not be repeated here.

[0029] The above specific process conditions in the preparation process of the present application can make the yield of the product 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside higher and more green and environmentally friendly.

[0030] In a second aspect, the present application provides a stereoisomer, tautomer, conformational isomer of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside or a pharmaceutically acceptable salt thereof according to the first aspect.

[0031] In a third aspect, the present application provides use of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside or a stereoisomer, a tautomer, a conformer thereof or a pharmaceutically acceptable salt of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside according to the first aspect or the second aspect in the preparation of a drug for preventing and / or treating neurodegenerative diseases.

[0032] Preferably, the dosage form of the drug comprises tablets, capsules, pills, granules, oral liquids or suspensions.

[0033] Preferably, the drug further comprises a pharmaceutically acceptable carrier or excipient.

[0034] Preferably, the neurodegenerative diseases include Parkinson's disease, Alzheimer's disease or stroke.

[0035] In a fourth aspect, the present application provides use of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside or a stereoisomer, a tautomer, a conformer thereof or a pharmaceutically acceptable salt of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside according to the first aspect or the second aspect in the preparation of a preparation for repairing nerve cell damage.

[0036] Compared with the prior art, the present application has the following beneficial effects:

[0037] The present application creatively separates and purifies a novel structure of cedrane diterpene glycoside from tobacco raw materials. The compound can effectively protect glutamate-induced pseudo neuronal PC12 cell damage, and has the potential to develop into a drug for preventing and / or treating neurodegenerative diseases. The preparation process of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside involved in the present application has simple and easy-to-control operation steps, is suitable for large-scale production, and the fillers and solvents used for extraction and separation can be recycled, which is green and environmentally friendly. BRIEF DESCRIPTION OF DRAWINGS

[0038] Figure 1 is 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside 1 H-NMR chart;

[0039] Figure 2 is 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside 13 C-NMR chart;

[0040] Figure 3HR-ESI-MS image of 3,7-ceberdiene-2,11,12-triol-6-O-β-D-glucoside. Detailed Implementation

[0041] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0042] Example 1

[0043] This embodiment provides a method for preparing 3,7-ceberdiene-2,11,12-triol-6-O-β-D-glucoside, which comprises the following steps:

[0044] (1) Yunnan tobacco leaves (100 g) were refluxed with 1 L of 70% ethanol aqueous solution for 3 times, each time for 2 hours. The ethanol extracts were combined and concentrated under reduced pressure to obtain 49 g of crude extract. The crude extract was dispersed in 0.5 L of water, and after filtering out insoluble matter, it was extracted with petroleum ether 3 times and n-butanol 3 times, each time with 1 L, to obtain 3 L of n-butanol extract solution.

[0045] (2) The extract (32 g) obtained after concentration of n-butanol extract (3 L) under reduced pressure was dissolved in water and purified by separation and purification by HP-20 macroporous adsorption resin column. It was eluted with pure water until colorless, and then eluted with 15% ethanol / water (V / V, 2 L) until colorless. The solvent was recovered from the 15% ethanol / water eluent under reduced pressure to obtain the primary component of cephalosporin-type diterpene glycoside (3.6 g).

[0046] (3) The primary fraction of cephalodiene-2,11,12-triol-6-O-β-D-glucoside was purified by preparative HPLC to obtain pure 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside. The preparative HPLC conditions were: 25% acetonitrile-water, isocratic elution, flow rate 5 mL / min, detection wavelength 210 nm, injection volume 300 μL, and the column was an XBridge BEH C18 (250×10 mm, 5 μm, 130 Å). The t of pure 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside was... R = 30.20 min. The product is a white amorphous powder.

[0047] The structure of the product was analyzed and identified using NMR and MS spectroscopic techniques. 1 The H-NMR (CD3OD) characterization results are as follows: Figure 1 As shown, 13 The C-NMR (CD3OD) characterization results are as follows: Figure 2 As shown, the HR-ESI-MS characterization results are as follows: Figure 3The product prepared was proved to be 3,7-seco-2, 11, 12-trihydroxy-6-0-β-D- glucoside of cedrene as shown in formula I.

[0048] The physicochemical properties and spectral information thereof are as follows:

[0049] HR-ESI-MS m / z 413.2172 [M + H] + (calcd for C 21 H 33 O8 + , 502.3142).

[0050] 1 H-NMR (600 MHz, CD3OD) δ H1.26 (1H, m, H-1), 4.47 (1H, dd, J = 4.8,9.6 Hz, H-2), 5.46 (1H, d, J = 10.8 Hz, H-3), 2.60 (1H, dd, J = 6.0, 12.0 Hz,H-5a), 2.07 (1H, m, H-5b), 4.75 (1H, td, J = 4.8, 10.8 Hz, H-6), 5.07 (1H,dd, J = 1.2, 10.2 Hz, H-7), 2.11 (1H, m, H-9a), 2.03 (1H, m, H-9b), 1.52 (1H,m, H-10a), 1.34 (1H, m, H-10b), 3.79 (1H, m, H-11), 2.42 (1H, m, H-13a), 1.23(1H, m, H-13b), 1.63 (1H, m, H-14a), 1.42 (1H, m, H-14b), 1.19 (1H, m, H-15),0.73 (3H, d, J = 6.0 Hz, H-16), 0.89 (3H, d, J = 6.0 Hz, H-17), 1.67 (6H, s,H-18, 19), 0.98 (3H, s, H-20), 4.37 (1H, d, J = 7.8 Hz, H-1′), 3.16 (1H, m,H-2′), 3.33 (1H, m, H-3′), 3.28 (1H, m, H-4′), 3.21 (1H, m, H-5′), 3.80 (1H,dd, J = 12.0, 1.8 Hz, H-6′a), 3.64 (1H, dd, J = 12.0, 5.4 Hz, H-6′b);

[0051] 13 C-NMR (150 MHz, CD3OD) δ C48.1 (C-1), 72.2 (C-2), 128.5 (C-3), 138.4 (C-4), 47.2 (C-5), 76.9 (C-6), 127.3 (C-7), 139.8 (C-8), 37.6 (C-9), 31.5 (C-10), 72.2 (C-11), 77.4 (C-12), 34.9 (C-13), 19.7 (C-14), 30.2 (C-15), 21.1 (C-16), 20.6 (C-17), 16.4 (C-18), 17.4 (C-19), 24.8 (C-20), 102.9 (C-1'), 75.3 (C-2'), 78.2 (C-3'), 71.6 (C-4'), 77.9 (C-5'), 62.8 (C-6').

[0052] Example 2

[0053] This example provides a method for preparing 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside, which is operated as the following steps:

[0054] (1) Zimbabwe tobacco sheet (1 kg) is extracted with 1 L of pure water at 60°C for 3 times, each for 2 hours. After the water extract is combined and concentrated under reduced pressure, a crude extract of 0.76 kg is obtained. The crude extract is dispersed with 0.8 L of water, and the insoluble matter is filtered out. Then, n-hexane is used to extract 3 times, and ethyl acetate is used to extract 3 times, each for 1 L, to obtain 3 L of ethyl acetate extract solution.

[0055] (2) The ethyl acetate extract solution (3 L) is concentrated under reduced pressure, and the obtained extract (0.29 kg) is dissolved in water. Then, the solution is separated and purified by an XAD-2 macroporous adsorption resin column. Pure water is used for elution until it is colorless. Then, 15% ethanol / water (V / V, 4 L) is used for elution until it is colorless. After the eluate of 15% ethanol / water is concentrated under reduced pressure, a primary component of cedrane-type diterpene glycoside (10.4 g) is obtained.

[0056] (3) The primary component of cedrane-type diterpene glycoside is purified by preparative HPLC to obtain 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside pure product. The preparative HPLC conditions are as follows: 15% acetonitrile / water, isocratic elution, a flow rate of 3 mL / min, detection at a wavelength of 210 nm, a sample injection amount of 500 μL, and a chromatographic column of XBridge BEH C18 (250×10 mm, 5 μm, 130 angstrom). The tR of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside pure product is 9.5 min. R= 70.86 min. The product was a white amorphous powder.

[0057] The structure of the product was identified by NMR and MS spectroscopy. According to the characterization results, it was proved that the product prepared was 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside as shown in formula I.

[0058] Example 3

[0059] The present example provides a preparation method of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside, which is operated as follows:

[0060] (1) The flue-cured tobacco leaves (500 g) from Yunnan Province were soaked and extracted with 1 L of 50% methanol aqueous solution at 50°C for 3 times, 10 hours each time. The methanol extract was combined and concentrated under reduced pressure to obtain a crude extract 0.36 kg. The crude extract was dispersed with 0.8 L of water, and the insoluble matter was filtered out. Then, n-hexane was used to extract 3 times, and sec-butanol was used to extract 3 times, 1 L each time, to obtain a sec-butanol extract solution 3 L.

[0061] (2) The sec-butanol extract solution (3 L) was concentrated under reduced pressure to obtain an extract (0.24 kg). The extract was dissolved with water and separated and purified by an SP-700 macroporous adsorption resin column. Pure water was used for elution until it was colorless. Then, 15% ethanol / water (V / V, 4 L) was used for elution until it was colorless. The 15% ethanol / water eluate was concentrated under reduced pressure to obtain a cedrane diterpene glycoside primary component (9.6 g).

[0062] (3) The cedrane diterpene glycoside primary component was purified by preparative HPLC to obtain 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside pure product. The preparative HPLC conditions were as follows: 30% acetonitrile / water, isocratic elution, a flow rate of 4 mL / min, 210 nm wavelength detection, an injection volume of 800 μL, and an XBridge BEH C18 (250×10 mm, 5 μm, 130 angstrom) column. The tR of 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside pure product was 50.72 min. R = 70.86 min. The product was a white amorphous powder.

[0063] The structure of the product was identified by NMR and MS spectroscopy. According to the characterization results, it was proved that the product prepared was 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside as shown in formula I.

[0064] Test Example

[0065] 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside protects PC12 cells from L-glutamic acid-induced damage:

[0066] The recovered PC12 cells were inoculated in DMEM medium containing 10% fetal bovine serum and 1% double antibody for culture. When the cell confluence reached 80%, the cells were passaged, and the cell density was adjusted to 10 5 / mL in a 96-well plate, 100 μL per well, and cultured in a 37°C, 5% CO2 saturated humidity incubator.

[0067] The grouping conditions were blank group, model group, positive drug (nimodipine) group and sample (3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside) group. After the cells adhered, the positive drug group and the 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside group were added with nimodipine (10 μM) or 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside (10 μM) for pre-incubation, 4 hours later, the blank group was replaced with new culture medium, the other groups were replaced with 5 mM glutamic acid damage agent, at the same time, the positive drug group and the sample group were added with the corresponding drugs (10 μM) again, the model group was supplemented with the corresponding volume of culture medium, and the glutamic acid damage was performed for 4 hours. Then, 10 μL of MTT (5 mg / ml) was added to each well for further reaction for 4 hours until the crystals were fully formed. Then, 150 μL of DMSO was added to each well to dissolve the crystals, and the absorbance value of each group was detected at 570 nm. The cell survival rate of each well and the relative survival rate compared with the model group were calculated. Each experiment was repeated 3 times, and the results are shown in Table 1.

[0068] Table 1

[0069]

[0070] As shown by the data in Table 1, compared with the blank group, the survival rate of PC12 cells in the model group was significantly reduced under the condition of glutamic acid induction. However, 10 μM 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside had a good improvement effect on glutamic acid-induced PC12 cell damage, and the cell survival rate was increased by 50.86% compared with the model group, which was higher than that of the positive drug nimodipine. It is proved that the compound 3,7-cedrene-2,11,12-triol-6-O-β-D-glucoside represented by formula (1) has more advantages than the marketed drug for treating ischemic cerebrovascular diseases.

[0071] The applicant declares that the technical scheme of the present application is illustrated by the above-mentioned embodiments, but the present application is not limited to the above-mentioned embodiments, that is, the present application does not mean that it must rely on the above-mentioned embodiments to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present application.

[0072] The preferred embodiments of the present application are described in detail above, but the present application is not limited to the specific details in the above-mentioned embodiments, and within the technical concept scope of the present application, various simple modifications can be made to the technical scheme of the present application, and these simple modifications all belong to the protection scope of the present application.

[0073] In addition, it should be noted that each specific technical feature described in the above-mentioned specific embodiments can be combined by any suitable method without contradiction, and in order to avoid unnecessary repetition, the present application will not further describe various possible combination methods.

Claims

1. A 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside, characterized in that, The structural formula of the 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside is shown in Formula I: 。 2. The method for preparing 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside according to claim 1, characterized in that, The preparation method includes the following steps: (1) Extract the tobacco raw material by alcohol extraction or water extraction to obtain an extract, concentrate the extract to obtain a paste, dissolve the paste in water and extract it in sequence with a non-polar solvent and a polar solvent to obtain an extract; (2) The extract was concentrated to obtain an extract paste, which was then dissolved in water and purified by elution with macroporous adsorption resin to obtain a crude extract. (3) The crude extract was purified by preparative liquid chromatography to obtain the 3,7-ceberdiene-2,11,12-triol-6-O-β-D-glucoside.

3. The preparation method according to claim 2, characterized in that, The tobacco raw materials include any one or a combination of at least two of the following: tobacco leaves, tobacco sheets, shredded tobacco, or tobacco dust. Preferably, the solvent used for the alcohol extraction includes anhydrous methanol, anhydrous ethanol, an aqueous methanol solution, or an aqueous ethanol solution; Preferably, the alcohol extraction or water extraction method includes any one or a combination of at least two of the following: soaking extraction, heating reflux extraction, or ultrasonic extraction; Preferably, in the alcohol extraction or water extraction, the ratio of tobacco raw material to extraction solvent is 1:(100-1000) g / L.

4. The preparation method according to claim 2 or 3, characterized in that, The nonpolar solvent includes petroleum ether and / or n-hexane; Preferably, the polar solvent includes any one or a combination of at least two of ethyl acetate, n-butanol, or sec-butanol.

5. The preparation method according to any one of claims 2-4, characterized in that, The macroporous adsorption resin is selected from any one or a combination of at least two of HP-20, SP-700, D-101, XAD-2 or XAD-15 resins. Preferably, the elution and purification steps of the macroporous adsorption resin are as follows: first, elute with water until colorless, then elute with 10-20% alcohol solution until colorless, and collect the 10-20% alcohol eluent.

6. The preparation method according to any one of claims 2-5, characterized in that, The column used in the preparative liquid chromatography is a C18 preparative column; Preferably, the mobile phase of the preparative liquid chromatography is an aqueous acetonitrile solution; Preferably, the volume fraction of acetonitrile in the acetonitrile aqueous solution is 15-30%; Preferably, the flow rate of the mobile phase in the preparative liquid chromatography is 3-5 mL / min.

7. Stereoisomers, tautomers, conformational isomers, or pharmaceutically acceptable salts thereof of 3,7-ceberdiene-2,11,12-triol-6-O-β-D-glucoside according to claim 1.

8. The use of stereoisomers, tautomers, conformational isomers or pharmaceutically acceptable salts thereof of 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside according to claim 1 or 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside according to claim 7 in the preparation of medicaments for the prevention and / or treatment of neurodegenerative diseases.

9. The application according to claim 8, characterized in that, The dosage forms of the drug include tablets, capsules, pills, granules, oral liquids, or suspensions; Preferably, the drug further contains a pharmaceutically acceptable carrier or excipient; Preferably, the neurodegenerative disease includes Parkinson's disease, Alzheimer's disease, or stroke.

10. The use of the stereoisomers, tautomers, conformational isomers, or pharmaceutically acceptable salts thereof of 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside according to claim 1 or 3,7-cephalodiene-2,11,12-triol-6-O-β-D-glucoside according to claim 7 in the preparation of formulations for repairing nerve cell damage.

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