CN113087607A - Novel diaryl nonane I free radical inhibitor in saxifraga stolonifera as well as separation preparation process and application thereof - Google Patents
Novel diaryl nonane I free radical inhibitor in saxifraga stolonifera as well as separation preparation process and application thereof Download PDFInfo
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- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 244000288377 Saxifraga stolonifera Species 0.000 title claims abstract description 36
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 117
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- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
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- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
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- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
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- 125000001474 phenylpropanoid group Chemical group 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
- C07C49/248—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings having unsaturation outside the aromatic rings
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Abstract
The invention discloses a novel diaryl nonane I free radical inhibitor in saxifraga stolonifera in mountainous regions, and a separation preparation process and application thereof. The specific preparation process comprises the following steps: the method comprises five steps of extraction, on-line free radical inhibitor component screening, microporous resin column medium pressure chromatography rough separation, on-line free radical inhibitor screening and reverse phase preparation column preparation. The new diaryl nonane Saximonsina free radical inhibitor prepared by the method can be applied to preparation of free radical inhibition medicines or health-care foods, and concretely can be used as an effective component to prepare various medicinal preparations or health-care foods according to any pharmaceutically or food scientifically acceptable carriers. The extraction solvent, the microporous resin column, the reverse phase chromatographic column separation solvent and the reverse phase chromatographic separation material in the preparation process can be recycled; the raw material source is wide, the large-scale operation can be realized through the technological steps of cold soaking extraction of methanol at room temperature and the like, and the purity of the product can be ensured to be more than 95% through high-pressure reversed-phase preparative chromatographic separation.
Description
Technical Field
The invention relates to the technical field of separation of a novel diaryl nonane free radical inhibitor in saxifraga stolonifera, and particularly relates to a novel diaryl nonane I free radical inhibitor in saxifraga stolonifera as well as a separation preparation process and application thereof.
Background
Mountain Saxifraga montana, an perennial herb of the genus Saxifraga (Saxifragaceae) of the family Saxifragaceae, the name of Tibetan medicine: the "Hanren Jimu" is mainly distributed in Shaanxi, Qinghai, West Sichuan, northwest Yunnan, east and south of Tibet in China. The main effects are as follows: clear heat and remove toxicity, pacify liver and subdue yang. It is indicated for headache due to liver-gallbladder damp-heat, spleen-stomach damp-heat, carbuncle, swelling and sore-toxin. Modern pharmacological studies have demonstrated that phenols are the major active ingredient of plants of the genus saxifrage. The phenolic compounds have good free radical scavenging activity reported in the literature. In order to further accelerate the quality evaluation, production and sale and development steps of related new drugs of the mountain saxifrage, it is necessary to excavate potential active ingredients from the saxifrage.
At present, only one research on chemical compositions (conversion of chemical compositions from Saxifraga montana, Jun-Xi Liu, Duo-Long Di, Yan-Ping Shi,2008,55,863-870) in the Saxifraga stolonifera in the mountainous region is reported, and the research utilizes the traditional phytochemical means to separate and identify 18 compounds including phenylpropanoids, benzoates, flavonoids, terpenes and the like from the Saxifraga stolonifera in the mountainous region. No literature report is available on the separation and preparation process and the application of the free inhibitor in the saxifrage in mountainous regions. Therefore, a method for separating and preparing a novel diaryl nonane free radical inhibitor from saxifraga stolonifera in a large scale with a simple process is needed to be established.
Disclosure of Invention
Based on the technical problems, the invention aims to provide a novel diaryl nonane I free radical inhibitor in saxifraga stolonifera and a separation preparation process and application thereof.
The invention provides a new diaryl nonane I free radical inhibitor in protected saxifraga stolonifera, wherein the diaryl nonane I free radical inhibitor is brown oil and is named as diaryl nonaneSaximonisin A-like free radical inhibitor with molecular formula of C22H26O6The chemical structural formula is as follows:
the invention discloses a separation and preparation process of a novel diaryl nonane I free radical inhibitor in protected saxifraga stolonifera in mountainous regions, which comprises the following steps:
Further, in step 1, step 3 and step 5, the drying under reduced pressure is carried out under the following conditions: the vacuum degree is 50-250 mbar, and the temperature is 40-60 ℃.
Further, in the step 2, the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the proportion of 0-60 min and 5-50% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the reaction ring length was 15 m.
Further, in the step 4, the mobile phase a adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the ratio of 0-60 min to 14% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the reaction ring length was 15 m.
Further, the pure water resistant C18 reverse phase chromatographic column in the steps 2, 4 and 5 is any one of a pure water resistant Reprosil C18 reverse phase chromatographic column, a pure water resistant Megres C18 reverse phase chromatographic column and a pure water resistant Kromasil100-5-C18(w) reverse phase chromatographic column.
The invention also protects the application of the novel diaryl nonane I free radical inhibitor in the SaximonsinA alpine, wherein the diaryl nonane Saximonsina free radical inhibitor can be applied to the preparation of free radical inhibition drugs or health-care foods, and specifically can be used as an effective component to prepare various medicinal preparations according to any pharmaceutically acceptable carrier, or can be used as an effective component to prepare various health-care foods according to any food scientifically acceptable carrier.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention has low cost and high product purity
The solvent used for extraction, the solvent used for separation of the microporous resin column and the reversed phase chromatographic column can be recycled; materials used for reverse phase chromatographic separation can be recycled, the recycled solvent and the recycled separation materials ensure lower average separation cost, and the high-pressure reverse phase preparative chromatographic separation can ensure that the purity of the product is more than 95%.
(2) The preparation method can meet the requirement of large-scale production
The raw material requirement is not high, the cost is low, the wild or commercially available mountain saxifrage can be used, and the batch preparation is easy; the methanol is extracted by cold immersion at room temperature, and the operation is easy; the separation adopts a microporous resin column for rough separation, and the microporous resin separation material can be arranged in a medium-pressure column chromatography system, so that the large-scale separation is easy to realize; the reversed-phase preparative liquid chromatography used in the separation and purification is a rapid isocratic method and is also very suitable for mass production.
Drawings
FIG. 1 is an on-line HPLC-DPPH screening chromatogram of a total mountain saxifrage sample;
FIG. 2 is a medium pressure chromatographic separation diagram of a sample-mixed microporous resin of a mountain saxifrage extract according to the present invention;
FIG. 3 is an online HPLC-DPPH screening chromatogram of a target component of Saxifraga stolonifera in mountainous regions;
FIG. 4 is a reversed-phase preparative liquid chromatography separation chart of a mountain saxifrage target component Fr 4;
FIG. 5 is a chromatogram for verifying the purity and activity of the new diarylnonane I radical inhibitor Fr4-1(Saximonsina) in Saxifraga stolonifera of the present invention;
FIG. 6 is a high resolution mass spectrum of a novel diaryl nonane I radical inhibitor in Saxifraga stolonifera of the present invention;
FIG. 7 shows a new diaryl nonane I radical inhibitor in Saxifraga stolonifera of the present invention1H NMR nuclear magnetic map;
FIG. 8 shows a new diaryl nonane I radical inhibitor in Saxifraga stolonifera of the present invention13C NMR nuclear magnetic map;
FIG. 9 is a DEPT nuclear magnetic map of the new diaryl nonane I radical inhibitor in saxifraga hillside according to the present invention;
FIG. 10 is a two-dimensional nuclear magnetic diagram of the new diaryl nonane I radical inhibitor HSQC in Saxifraga stolonifera of the present invention;
FIG. 11 is a two-dimensional nuclear magnetic map of HMBC, a novel diaryl nonane I radical inhibitor in Saxifraga stolonifera of the present invention;
FIG. 12 is a two-dimensional nuclear magnetic diagram of the novel diaryl nonane I radical inhibitor H-HCOSY in Saxifraga glauca of the present invention;
FIG. 13 is a NOESY two-dimensional nuclear magnetic map of the novel diaryl nonane I radical inhibitor in Saxifraga stolonifera of the present invention;
FIG. 14 is an IR spectrum of a novel diarylnonane-type I radical inhibitor from Saxifraga stolonifera according to the present invention;
FIG. 15 is a UV spectrum of a novel diarylnonane-type I radical inhibitor from Saxifraga stolonifera according to the present invention;
FIG. 16 is a graph showing the optical rotation of the novel diarylnonane-type I radical inhibitor in Saxifraga stolonifera of the present invention;
FIG. 17 is a structural diagram of the novel diarylnonane-type I radical inhibitor of Saxifraga stolonifera according to the present invention.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The separation and preparation process of the novel diaryl nonane I free radical inhibitor in the saxifraga stolonifera concretely comprises the following steps:
The diaryl nonane SaximusinA free radical inhibitor can be applied to preparation of free radical inhibition drugs or health-care foods, and specifically can be used as an effective component to prepare various medicinal preparations according to any pharmaceutically acceptable carrier, or can be used as an effective component to prepare various health-care foods according to any food scientifically acceptable carrier.
Example 2
The separation and preparation process of the novel diaryl nonane I free radical inhibitor in the saxifraga stolonifera concretely comprises the following steps:
step 4, on-line free radical inhibitor screening: adding methanol with the volume concentration of 70% into the mountain saxifrage target component for dissolving, preparing a sample with the concentration of 50.0mg/mL, filtering through a 0.45-micrometer microporous filter membrane to obtain a solution containing the target component, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the mountain saxifrage target component by utilizing an online HPLC-DPPH chromatography combined system, wherein the online HPLC-DPPH chromatography combined system is characterized in that a first high performance liquid chromatograph adopts a pure water resistant Megres C18(250 multiplied by 4.6mm, 5 micrometers) reversed phase chromatographic column, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517 nm; the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the proportion of 0-60 min and 14% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the length of the reaction ring is 15 m;
The diaryl nonane SaximusinA free radical inhibitor can be applied to preparation of free radical inhibition drugs or health-care foods, and specifically can be used as an effective component to prepare various medicinal preparations according to any pharmaceutically acceptable carrier, or can be used as an effective component to prepare various health-care foods according to any food scientifically acceptable carrier.
Example 3
The separation and preparation process of the novel diaryl nonane I free radical inhibitor in the saxifraga stolonifera concretely comprises the following steps:
step 2, screening the components of the on-line free radical inhibitor: adding 80% methanol by volume concentration into 1g of mountain saxifrage sample to dissolve, preparing a sample with the concentration of 80.0mg/mL, filtering with a 0.45 mu m microporous membrane to obtain mountain saxifrage methanol sample solution, namely filtrate B, taking 1mL of filtrate B, and screening a free radical inhibitor component in a mountain saxifrage crude sample by using an online HPLC-DPPH chromatography combined system, wherein the online HPLC-DPPH chromatography combined system is characterized in that a first high performance liquid chromatograph adopts a pure water resistant Kromasil100-5-C18(w) (250 x 4.6mm, 5 mu m) reversed phase chromatographic column, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517 nm; the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the conditions of 0-60 min and 5-50% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the length of the reaction ring is 15 m;
step 4, on-line free radical inhibitor screening: adding 80% methanol by volume concentration into the target component of the mountain saxifrage for dissolving, preparing a sample with the concentration of 80.0mg/mL, filtering with a 0.45-micrometer microporous filter membrane to obtain a solution containing the target component of the mountain saxifrage, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the target component of the mountain saxifrage by utilizing an online HPLC-DPPH chromatography combined system, wherein the online HPLC-DPPH chromatography combined system is characterized in that a first high performance liquid chromatograph adopts a pure water resistant Kromasil100-5-C18(w) (250 multiplied by 4.6mm, 5 micrometers) reverse phase chromatographic column, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517 nm; the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the proportion of 0-60 min and 14% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the length of the reaction ring is 15 m;
The diaryl nonane SaximusinA free radical inhibitor can be applied to preparation of free radical inhibition drugs or health-care foods, and specifically can be used as an effective component to prepare various medicinal preparations according to any pharmaceutically acceptable carrier, or can be used as an effective component to prepare various health-care foods according to any food scientifically acceptable carrier.
Example 4
The activity of a novel diaryl nonane I free radical inhibitor in saxifraga stolonifera is verified:
respectively adding chromatographic methanol into a new diaryl nonane SaximonsinA free radical inhibitor in the mountain saxifrage obtained by separation for dissolution, preparing a sample solution with the concentration of 0.3mg/mL, filtering the sample solution by a 0.45-micrometer microporous filter membrane to obtain a new diaryl nonane SaximonsinA free radical inhibitor sample solution in the mountain saxifrage, taking 1mL of the sample, and verifying the activity of the new diaryl nonane Saximonsin A free radical inhibitor in the mountain saxifrage by utilizing an online HPLC-DPPH (high performance liquid chromatography-DPPH (denaturing pH) chromatography combined system; in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant Reprosil C18 reversed phase chromatographic column (250 multiplied by 4.6mm, 5 mu m), a mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, a mobile phase B is an acetonitrile solution, the flow rate of the mobile phase is 1.0mL/min according to 0-60 min and 5-50% B, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, the concentration of the DPPH solution is 25 mu g/mL, and the flow rate of a mobile phase is 0.5 mL/min; the reaction ring length is 15m, the detection wavelength is 517nm, and the activity verification chromatogram map (detailed in figure 5) is shown. A new diaryl nonane Saximonsin A free radical inhibitor has mass spectrum, nuclear magnetic diagram, infrared spectrum, ultraviolet spectrum and optical rotation test diagram (shown in figures 6-16), and a new diaryl nonane SaximonsinA compound structure diagram (shown in figure 17).
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A new diaryl nonane I free radical inhibitor in SaximonsinA mountainous region is characterized in that the diaryl nonane I free radical inhibitor is brown oil, is named as diaryl nonane Saximinosa free radical inhibitor, and has a molecular formula of C22H26O6The chemical structural formula is as follows:
2. the process for separating and preparing the novel diaryl nonane I radical inhibitor in the saxifraga hillside according to claim 1, which comprises the following steps:
step 1, extraction: drying the whole mountain saxifrage in the shade, coarsely crushing, and mixing the materials according to a material-liquid ratio of 1 g: extracting with 5-100 mL of methanol at room temperature for 2-4 times, each time for 2-4 hours, filtering, combining the filtrates to obtain a filtrate A, and drying the filtrate A under reduced pressure to obtain a saxifrage extract, wherein the polyamide content is as follows: mixing the saxifrage extract with the amount of 3:1, and drying under reduced pressure to obtain a sample of saxifrage extract;
step 2, screening the components of the on-line free radical inhibitor: adding 70-90% methanol by volume concentration into 1g of mountain saxifrage sample to dissolve, preparing a sample with the concentration of 50.0-100.0 mg/mL, filtering with a 0.45-micrometer microporous filter membrane to obtain a mountain saxifrage methanol sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor component in a mountain saxifrage crude sample by using an online HPLC-DPPH chromatography combined system, wherein the online HPLC-DPPH chromatography combined system is characterized in that a first high performance liquid chromatograph adopts a pure water resistant C18(250 multiplied by 4.6mm, 5 micrometers) reversed phase chromatographic column, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517 nm;
step 3, carrying out medium-pressure chromatography rough separation on the microporous resin column: the method comprises the following steps of mixing a sample with a mountain saxifrage extract, carrying out medium-pressure chromatographic separation on the sample by using microporous resin, detecting the sample by using an ultraviolet detector with the detection wavelength of 210nm, collecting the 4 th main chromatographic peak fraction in a preparative chromatogram, and drying the fraction under reduced pressure to obtain a target component Fr4, wherein the medium-pressure chromatographic separation working parameters of a microporous resin column are as follows: the length of a chromatographic column is 460mm, the diameter of the chromatographic column is 49mm, the stationary phase of a microporous resin column is CHP20P, the mobile phase A is water, the mobile phase B is methanol, the chromatographic conditions are 0-90 min and 0-100% of B, the sample injection amount is 35.4g, and the flow rate is 50 mL/min;
step 4, on-line free radical inhibitor screening: adding 70-90% methanol into the target component of the mountain saxifrage for dissolving, preparing a sample with the concentration of 50.0-100.0 mg/mL, filtering with a 0.45-micrometer microporous filter membrane to obtain a solution containing the target component of the mountain saxifrage, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the target component of the mountain saxifrage by using an online HPLC-DPPH chromatography combined system, wherein in the online HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant C18(250 multiplied by 4.6mm, 5 micrometers) reversed phase chromatographic column, and the detection wavelength is 210 nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517 nm;
step 5, preparing a reversed-phase preparation column: separating the filtrate C by a reversed-phase preparative column, detecting by an ultraviolet detector with the detection wavelength of 210nm, collecting corresponding chromatographic peak fraction Fr4-1 in a preparative chromatogram, and drying the chromatographic peak fraction Fr4-1 under reduced pressure to obtain a new diarylnonane radical inhibitor Fr4-1 with the purity of more than 95 percent, which is named as Saximonsina; wherein the working parameters for the preparation of the reversed-phase preparation column are as follows: the preparation method comprises the steps of preparing a column with the length of 250mm and the diameter of 20mm, using a reverse phase chromatographic column with a stationary phase of 5 mu m of pure water-resistant C18, using a mobile phase A as an aqueous solution, using a mobile phase B as an acetonitrile solution, eluting according to the concentration of 14% B in 0-60 min, wherein the sample injection volume is 4mL, and the flow rate is 19 mL/min.
3. The process for separating and preparing the novel diarylnonane I radical inhibitor from Saxifraga stolonifera as claimed in claim 2, wherein the drying under reduced pressure in step 1, step 3 and step 5 is carried out under the following conditions: the vacuum degree is 50-250 mbar, and the temperature is 40-60 ℃.
4. The process for separating and preparing the novel diaryl nonane I free radical inhibitor in the saxifraga hillside as claimed in claim 2, wherein in the step 2, the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to 0-60 min and 5-50% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the reaction ring length was 15 m.
5. The process for separating and preparing the novel diaryl nonane I free radical inhibitor in the saxifraga hillside as claimed in claim 2, wherein in the step 4, the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the proportion of 0-60 min and 14% B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 25 mug/mL and the flow rate of the mobile phase is 0.5 mL/min; the reaction ring length was 15 m.
6. The process for separating and preparing a novel diarylnonane I radical inhibitor from Saxifraga stolonifera as claimed in claim 2, wherein the pure water resistant C18 reverse phase chromatographic column in step 2, step 4 and step 5 is any one of pure water resistant Reprosil C18 reverse phase chromatographic column, pure water resistant Megres C18 reverse phase chromatographic column and pure water resistant Kromasil100-5-C18(w) reverse phase chromatographic column.
7. The novel diaryl nonane I free radical inhibitor in the Saximonsin A as claimed in claim 1, which is characterized in that the diaryl nonane Saximonsin A free radical inhibitor can be applied to preparation of free radical inhibition drugs or health foods, and specifically can be used as an active ingredient to prepare various pharmaceutical preparations according to any pharmaceutically acceptable carrier, or can be used as an active ingredient to prepare various health foods according to any food scientifically acceptable carrier.
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| CN111171042A (en) * | 2020-01-15 | 2020-05-19 | 中国科学院西北高原生物研究所 | Separation preparation process and application of natural free radical scavenger in saxifrage |
| CN111187159A (en) * | 2020-01-15 | 2020-05-22 | 中国科学院西北高原生物研究所 | Separation process and application of natural free radical scavenger in saxifraga tangutica |
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| CN111171042A (en) * | 2020-01-15 | 2020-05-19 | 中国科学院西北高原生物研究所 | Separation preparation process and application of natural free radical scavenger in saxifrage |
| CN111187159A (en) * | 2020-01-15 | 2020-05-22 | 中国科学院西北高原生物研究所 | Separation process and application of natural free radical scavenger in saxifraga tangutica |
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| CN114149398A (en) * | 2021-12-13 | 2022-03-08 | 江西中医药大学 | Diphenylnonane compound, composition thereof, preparation method and application thereof |
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