CN113087606B - New diaryl nonane IV and III free radical inhibitor in saxifraga tangutica and separation preparation process and application thereof - Google Patents
New diaryl nonane IV and III free radical inhibitor in saxifraga tangutica and separation preparation process and application thereof Download PDFInfo
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 96
- 150000003254 radicals Chemical class 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims abstract description 52
- -1 diaryl nonane Chemical compound 0.000 title claims abstract description 47
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title claims abstract description 47
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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
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Abstract
The invention discloses a new diaryl nonane IV and III free radical inhibitor in saxifraga tangutica, a separation preparation process and application thereof. The specific preparation process comprises the following steps: the method comprises six steps of extraction, coarse separation of a microporous resin column, on-line screening of free radical inhibitor components, high-pressure reverse phase chromatographic column separation, on-line screening of free radical inhibitors and high-pressure reverse phase column preparation. The prepared diaryl nonane Saxitanina and SaxitansideB can be applied to preparation of free radical inhibition drugs or health-care foods, and can be specifically used as active ingredients to be prepared into various pharmaceutical preparations or health-care foods according to any carriers acceptable in pharmacy or food science. The extraction solvent, the microporous resin column and the solvent and the separation material used for the separation of the high-pressure reversed-phase chromatographic column 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, rough separation of a microporous resin column and the like, and the purity of the product can be ensured to be more than 95% through high-pressure preparative chromatographic separation.
Description
Technical Field
The invention relates to the technical field of separation of new diaryl nonane free radical inhibitors in saxifraga tangutica, in particular to new diaryl nonane IV and III free radical inhibitors in saxifraga tangutica and a separation preparation process and application thereof.
Background
Saxifraga tangutica engl, alias Gan Qinghu, is an annual evergreen herb of Saxifraga (Saxifragaceae) genus Saxifraga (Saxifraga), tibetan name: "Song Ji Di" is called "Luda" in Chinese medicine, and is mainly distributed under conifer bush with elevation of 2900-4900 m in Qinghai, gansu, tibet, sichuan and Dan and Keshimill areas. Thanggute saxifrage is a common Tibetan medicine, and can be used as a whole herb, and the records of Chinese medicine dictionary Hai: it is slightly bitter, pungent and cold in nature. The main effects are as follows: clearing liver-fire, promoting bile flow, invigorating spleen and stomach. The main treatment is as follows: hepatitis, cholecystitis, influenza. Modern pharmacological studies have demonstrated that phenols are the major active ingredient. The phenolic compounds have good free radical scavenging activity reported in the literature. However, currently, only 8 antioxidant phenolic compounds published in this topic are isolated and identified from saxifrage tangutica (Jun Dang, yandau Tao, yun Shao, et al. Antioxidant extracts and phenols isolated from Tibet Plateau media plant Saxifraga tandutifolia Industrial Crops and Products,2015, 78. In order to further accelerate the quality evaluation, production and sale and research and development steps of related new drugs of the saxifrage tangutica, more active ingredients with novel structures need to be excavated from the saxifrage tangutica.
The research related to the subject group has applied for the national invention patent (application number: 202010041021.3) describing the separation and preparation process and application of six galloyl natural radical scavengers with known structures in saxifrage tangutica, and no literature or patent report about new diarylnonane radical inhibitors is known at present. Therefore, a method for separating and preparing the diarylnonane free radical inhibitor from the saxifrage tangutica with simple process and large scale is needed to be established.
Disclosure of Invention
Based on the technical problems, the invention aims to provide novel diarylnonane IV and III free radical inhibitors in saxifraga tangutica, and a separation preparation process and application thereof.
The invention protects new diaryl nonane IV and III free radical inhibitors in saxifraga tangutica, wherein the diaryl nonane IV and III free radical inhibitors are brown yellow oil, are named as diaryl nonane Saxitansin A free radical inhibitor and Saxitansin B free radical inhibitor respectively, and have molecular formulas C 21 H 26 O 6 And C 27 H 36 O 10 The chemical structural formulas are respectively as follows:
the invention provides a separation and preparation process of a new diaryl nonane IV and III free radical inhibitor in saxifraga tangutica, which specifically comprises the following steps:
and 3, screening the components of the online free radical inhibitor: adding 70-100% methanol into the Thalictrum aquilegifolium target component Fr5 for dissolving, preparing a sample with the concentration of 70.0-120.0 mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a Thalictrum aquilegifolium target component Fr5 sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5 by using an online HPLC-DPPH chromatography combined system; wherein, in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a 7-X10 (250X 4.6mm,7 mu m) reversed phase chromatographic column resistant to pure water, and the detection wavelength is 254nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517nm;
Further, in step 1, step 2, step 4 and step 6, the conditions of reduced pressure drying are as follows: the vacuum degree is 50-250 mbar, and the temperature is 40-60 ℃.
Further, in the step 3, the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, the content is reduced according to the proportion of 0-60min and 10-45 percent B, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the reaction ring length was 15m.
Further, in the step 5, the mobile phase A adopted by the first high performance liquid chromatograph is an aqueous solution, the mobile phase B is an acetonitrile solution, the content of the solution B is 0 to 40min, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the reaction ring length was 15m.
Further, the pure water resistant C18 reverse phase chromatographic column in the steps 5 and 6 is a pure water resistant Reprosil C18 reverse phase chromatographic column or a pure water resistant Megres C18 reverse phase chromatographic column.
The invention also protects the application of the new diaryl nonane IV and III free radical inhibitors in the saxitansine, wherein the diaryl nonane Saxitansin A and Saxitansin B free radical inhibitors can be applied to the preparation of free radical inhibition drugs or health-care foods, and concretely, the diaryl nonane Saxitansin A and Saxitanside B free radical inhibitors can be used as active ingredients to prepare various medicinal preparations according to any pharmaceutically acceptable carrier, or can be used as the active ingredients 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 high-pressure reversed-phase chromatographic column can be recycled; materials used for separation can be recycled, the recycled solvent and the recycled separation materials ensure lower average separation cost, and the high-pressure preparative chromatography separation can ensure that the purity of the product is more than 95 percent.
(2) The preparation method can meet the requirement of large-scale production
The raw material requirement is low, the cost is low, the wild or commercial saxifraga tangutica 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 material can be arranged in a medium-pressure column chromatography system by adopting the coarse separation of a microporous resin column, and the large scale is easy to realize; the high-pressure reversed-phase preparative liquid chromatography used in the separation and purification is also very suitable for mass production.
Drawings
FIG. 1 is a chromatographic chart of the microporous resin separation of saxifrage tangutica methanol extract according to the present invention;
FIG. 2 is an on-line HPLC-DPPH screening chromatogram of a target component Fr5 of saxifraga tangutica of the present invention;
FIG. 3 is a diagram of a high pressure reversed phase chromatographic column for a target component Fr5 of Saxifraga tangutica according to the present invention;
FIG. 4 is an on-line HPLC-DPPH screening chromatogram of a target component Fr5-3 of Thangostereum glaucoides of the invention;
FIG. 5 is a reverse phase chromatographic analysis and preparative chromatogram of a target component Fr5-3 of Saxifraga tangutica according to the present invention;
FIG. 6 is a chromatogram for verifying the purity and activity of the new diarylnonane Saxitansin A (Fr 5-2) free radical inhibitor of saxitan grass in accordance with the present invention;
FIG. 7 is a chromatogram for verifying the purity and activity of the new diarylnonane Saxitanside B (Fr 5-3-1) free radical inhibitor of saxitansine of the present invention;
FIG. 8 is a mass spectrum of a novel diarylnonane Saxitansin A radical inhibitor of Saxitansin according to the present invention;
FIG. 9 shows the new diaryl nonane Saxitansin A free radical inhibition of Saxitansin according to the present inventionOf the agents 1 H NMR nuclear magnetic map;
FIG. 10 shows the preparation of the novel diarylnonane Saxitansin A free radical inhibitor of Saxitansin A of the present invention 13 C NMR nuclear magnetic map;
FIG. 11 is a DEPT nuclear magnetic map of the novel diarylnonane Saxitansin A free radical inhibitor of Saxitansin A of the present invention;
FIG. 12 is a two-dimensional nuclear magnetic diagram of HSQC of the new diarylnonane Saxitansin A free radical inhibitor in saxifraga tangutica of the present invention;
FIG. 13 is a two-dimensional nuclear magnetic map of HMBC of the novel diarylnonane Saxitansin A radical inhibitor of Saxitansin A in saxifraga tangutica according to the present invention;
FIG. 14 is a two-dimensional nuclear magnetic diagram of H-HCOSY of the novel diarylnonane Saxitan sin A radical inhibitor of saxitan in saxifrage tangutica of the present invention;
FIG. 15 is a two-dimensional nuclear magnetic diagram of NOESY of the novel diarylnonane Saxitansin A radical inhibitor of Saxitansin A in saxifrage tangutica of the present invention;
FIG. 16 is an infrared spectrum of a novel diaryl nonane Saxitansin A radical inhibitor from Saxitansin A of the present invention;
FIG. 17 is a UV spectrum of a novel diarylnonane Saxitan sin A radical inhibitor from saxifraga tangutica according to the present invention;
FIG. 18 is a graph showing the optical rotation of a novel diaryl nonane-type Saxitansin A radical inhibitor in saxifraga tangutica according to the present invention;
FIG. 19 is a CD test chart of a new diaryl nonane Saxitansin A free radical inhibitor in saxifraga tangutica according to the present invention;
FIG. 20 is a mass spectrum of a novel diaryl nonane Saxitanside B radical inhibitor of Saxitanside according to the present invention;
FIG. 21 shows the preparation of the novel diarylnonane Saxitanside B free radical inhibitors of Saxitanside B of the present invention 1 H NMR nuclear magnetic map;
FIG. 22 shows the preparation of a novel diarylnonane Saxitanside B radical inhibitor of Saxitanside of the invention 13 C NMR nuclear magnetic map;
FIG. 23 is a DEPT nuclear magnetic map of the novel diarylnonane Saxitanside B radical inhibitor of Saxitanside of the invention;
FIG. 24 is a two-dimensional nuclear magnetic diagram of HSQC of the novel diarylnonane Saxitanside B radical inhibitor of saxitansine in saxifrage tangutica of the present invention;
FIG. 25 is an HMBC two-dimensional nuclear magnetic map of a new diaryl nonane Saxitanside B radical inhibitor in saxifraga tangutica according to the present invention;
FIG. 26 is a two-dimensional nuclear magnetic diagram of the H-HCOSY of the novel diarylnonane Saxitanside B radical inhibitor of saxitansine in saxifrage tangutica of the present invention;
FIG. 27 is a two-dimensional nuclear magnetic map of the NOESY of the novel diaryl nonane Saxitanside B radical inhibitor of Saxitanside B in saxifrage tangutica according to the present invention;
FIG. 28 is an infrared spectrum of a novel diarylnonane Saxitanside B radical inhibitor from saxitansine of the present invention;
FIG. 29 is a UV spectrum of a novel diaryl nonane Saxitanside B radical inhibitor of Saxitanside, according to the present invention, from Saxitanside A;
FIG. 30 is a graph showing the optical rotation of a novel diarylnonane-type Saxitanside B radical inhibitor in saxifrage tangutica of the present invention;
FIG. 31 is a CD test chart of the novel diarylnonane Saxitanside B radical inhibitor of Saxitanside B in saxifrage tangutica of the present invention;
FIG. 32 is a structural diagram of the novel diarylnonane Saxitansin A and Saxitansin B radical inhibitors of Saxitansin 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 new diaryl nonane IV and III free radical inhibitor in the saxifraga tangutica concretely comprises the following steps:
and 3, screening the components of the online free radical inhibitor: adding 70% methanol in volume concentration into the Thalictrum aquilegifolium target component Fr5 for dissolving, preparing a sample with concentration of 70.0mg/mL, filtering with a 0.45 μm microporous membrane to obtain a Thalictrum aquilegifolium target component Fr5 sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5 by using an online HPLC-DPPH chromatography combined system (details are shown in figure 2); wherein, in the on-line HPLC-DPPH chromatography combination system, a first high performance liquid chromatograph adopts a 7-X10 (250 multiplied by 4.6mm,7 mu m) reversed phase chromatographic column resistant to pure water, and the detection wavelength is 254nm; a second high performance liquid chromatograph enters a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the first high performance liquid chromatograph adopts the mobile phase A as aqueous solution and the mobile phase B as acetonitrile solution, and the flow rate of the mobile phase is 1.0mL/min according to the proportion of 0-60min, 10-45 percent B; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the length of the reaction ring is 15m;
step 4, high-pressure reversed-phase chromatographic column separation: sample solution B of a Thalictrum tanguticum target component Fr5 in terms of the amount of polyamide: mixing the component sample of the thalictrum alutatum Fr5 =2:1, and drying under reduced pressure to obtain the sample mixture of the thalictrum alutatum extract, separating the sample by a preparative column filled with reverse phase 7-X10 filler, detecting by an ultraviolet detector with the detection wavelength of 254nm, collecting a second main chromatographic peak fraction Fr5-2 and a third main chromatographic peak fraction Fr5-3 (shown in detail in figure 3) in a preparative chromatogram, and drying under reduced pressure to obtain a new diaryl nonane radical inhibitor Saxitansin A with the purity of more than 95%; drying the chromatographic peak fraction Fr5-3 under reduced pressure to obtain a component containing a new diaryl nonane radical inhibitor Saxitanide B; wherein the reduced pressure drying condition is as follows: vacuum degree of 50mbar, temperature of 40 deg.C, respectively obtaining 637.4mg of herba Saxifragae Fr5-2 sample and 120.3mg of Fr5-3 target component sample; wherein, the working parameters for preparing the high-pressure reversed-phase preparation column are as follows: preparing a column with the length of 250mm and the diameter of 20mm, wherein the stationary phase of the reversed phase chromatographic column is 7 mu m 7-X10 filler, the mobile phase A is aqueous solution, the mobile phase B is acetonitrile solution, the target component Fr5 is subjected to gradient elution according to the ratio of 0-60min to 10-45 percent B, the sample introduction amount is 1.0g, and the flow rate is 19mL/min;
step 5, on-line free radical inhibitor screening: adding 70% methanol in volume concentration into the Thalictrum aquilegifolium target component Fr5-3 for dissolving, preparing a sample with concentration of 50.0mg/mL, filtering with 0.45 μm microporous membrane to obtain a solution of the Thalictrum aquilegifolium target component Fr5-3, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5-3 by using an on-line HPLC-DPPH chromatography combined system (details are shown in figure 4); in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant RepurSil C18 (250 multiplied by 4.6mm,5 mu m) reversed phase chromatographic column, and the detection wavelength is 254nm; a second high performance liquid chromatograph enters a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the mobile phase A adopted by the first high performance liquid chromatograph is aqueous solution, the mobile phase B is acetonitrile solution, the content is 0-40min, 27 percent B, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the length of the reaction ring is 15m;
The novel diaryl nonane IV and III free radical inhibitor in the saxitansine can be applied to the preparation of free radical inhibition medicines 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 new diaryl nonane IV and III free radical inhibitor in the saxifraga tangutica concretely comprises the following steps:
step 3, on-line free radical inhibitor component screening: adding methanol with the volume concentration of 100% into the Thalictrum aquilegifolium target component Fr5 for dissolving, preparing a sample with the concentration of 120.0mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a Thalictrum aquilegifolium target component Fr5 sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5 by using an online HPLC-DPPH chromatography combined system; wherein, in the on-line HPLC-DPPH chromatography combination system, a first high performance liquid chromatograph adopts a 7-X10 (250 multiplied by 4.6mm,7 mu m) reversed phase chromatographic column resistant to pure water, and the detection wavelength is 254nm; a second high performance liquid chromatograph enters a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the mobile phase A adopted by the first high performance liquid chromatograph is aqueous solution, the mobile phase B is acetonitrile solution, the content is 10-45 percent according to the weight percentage of 0-60min, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the length of the reaction ring is 15m;
step 4, high-pressure reversed-phase chromatographic column separation: sample solution B of a Thalictrum tanguticum target component Fr5 in terms of the amount of polyamide: mixing 5 components of thalictrum davidii Fr with 2:1, drying under reduced pressure to obtain a sample mixture of thalictrum davidii extract, separating the sample by a preparative column filled with reverse phase 7-X10 filler, detecting by an ultraviolet detector with a detection wavelength of 254nm, collecting a second main chromatographic peak fraction Fr5-2 and a third main chromatographic peak fraction Fr5-3 in a preparative chromatogram, and drying under reduced pressure to obtain a novel diaryl nonane radical inhibitor Saxitansin A with a purity of more than 95%; drying the chromatographic peak fraction Fr5-3 under reduced pressure to obtain a component containing a novel diaryl nonane radical inhibitor Saxitanide B; wherein the reduced pressure drying condition is as follows: 1158.6mg of saxifrage tangutica Fr5-2 sample and 231.4mg of Fr5-3 target component sample are respectively obtained at the vacuum degree of 250mbar and the temperature of 60 ℃; wherein, the working parameters of the preparation of the high-pressure reversed-phase preparation column are as follows: preparing a column with the length of 250mm and the diameter of 20mm, wherein the stationary phase of the reversed phase chromatographic column is 7 mu m 7-X10 filler, the mobile phase A is aqueous solution, the mobile phase B is acetonitrile solution, the target component Fr5 is subjected to gradient elution according to the ratio of 0-60min to 10-45 percent B, the sample introduction amount is 1.0g, and the flow rate is 19mL/min;
step 5, on-line free radical inhibitor screening: adding methanol with the volume concentration of 100% into the Thalictrum aquilegifolium target component Fr5-3 for dissolving, preparing a sample with the concentration of 100.0mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a solution of the Thalictrum aquilegifolium target component Fr5-3, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5-3 by utilizing an online HPLC-DPPH chromatography combined system; wherein, in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant Megres C18 (250 multiplied by 4.6mm,5 mu m) reversed phase chromatographic column, and the detection wavelength is 254nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the first HPLC using mobile phase A as aqueous solution and mobile phase B as acetonitrile solution, according to 0-40min, 27% B, mobile phase flow rate of 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the length of the reaction ring is 15m;
The novel diaryl nonane IV and III free radical inhibitor in the saxitansine can be applied to the preparation of free radical inhibition medicines 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 new diaryl nonane IV and III free radical inhibitor in the saxifraga tangutica concretely comprises the following steps:
step 3, on-line free radical inhibitor component screening: adding 80% methanol in volume concentration into the Thalictrum aquilegifolium target component Fr5 for dissolving, preparing a sample with concentration of 90.0mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a Thalictrum aquilegifolium target component Fr5 sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5 by using an online HPLC-DPPH chromatography combined system; wherein, in the on-line HPLC-DPPH chromatography combination system, a first high performance liquid chromatograph adopts a 7-X10 (250 multiplied by 4.6mm,7 mu m) reversed phase chromatographic column resistant to pure water, and the detection wavelength is 254nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the mobile phase A adopted by the first high performance liquid chromatograph is aqueous solution, the mobile phase B is acetonitrile solution, the content is 10-45 percent according to the weight percentage of 0-60min, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase of 0.5mL/min; the length of the reaction ring is 15m;
and 4, separating by using a high-pressure reverse phase chromatographic column: sample solution B of a target component Fr5 of the thalictrum glaucoides according to the weight of polyamide: mixing the component sample of the thalictrum alutatum Fr5 =2:1, drying under reduced pressure to obtain the sample mixture of the thalictrum alutatum extract, separating the sample by a preparation column filled with reverse phase 7-X10 filler, detecting by an ultraviolet detector with the detection wavelength of 254nm, collecting a second main chromatographic peak fraction Fr5-2 and a third main chromatographic peak fraction Fr5-3 in a preparation chromatogram, and drying under reduced pressure to obtain a new diarylnonane radical inhibitor Saxitansin A with the purity of more than 95%; drying the chromatographic peak fraction Fr5-3 under reduced pressure to obtain a component containing a new diaryl nonane radical inhibitor Saxitanide B; wherein the reduced pressure drying condition is as follows: vacuum degree of 150mbar, temperature of 50 deg.C to obtain 1308.2mg of herba Saxifragae Fr5-2 sample, and 265.1mg of Fr5-3 target component sample, respectively; wherein, the working parameters for preparing the high-pressure reversed-phase preparation column are as follows: preparing a column with the length of 250mm and the diameter of 20mm, wherein the stationary phase of the reversed phase chromatographic column is 7 mu m 7-X10 filler, the mobile phase A is aqueous solution, the mobile phase B is acetonitrile solution, the target component Fr5 is subjected to gradient elution according to the ratio of 0-60min to 10-45 percent B, the sample introduction amount is 1.0g, and the flow rate is 19mL/min;
step 5, on-line free radical inhibitor screening: adding 80% methanol in volume concentration into the target component Fr5-3 of the thalictrum aquilegifolium for dissolving, preparing a sample with the concentration of 90.0mg/mL, filtering by a 0.45 mu m microporous filter membrane to obtain a solution of the target component Fr5-3 of the thalictrum aquilegifolium, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the target component Fr5-3 of the thalictrum aquilegifolium by utilizing an on-line HPLC-DPPH chromatography combined system; in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant RepurSil C18 (250 multiplied by 4.6mm,5 mu m) reversed phase chromatographic column, and the detection wavelength is 254nm; a second high performance liquid chromatograph enters a DPPH solution dissolved in methanol, and the detection wavelength is 517nm; the mobile phase A adopted by the first high performance liquid chromatograph is aqueous solution, the mobile phase B is acetonitrile solution, the content is 0-40min, 27 percent B, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the length of the reaction ring is 15m;
The novel diaryl nonane IV and III free radical inhibitor in the saxitansine can be applied to the preparation of free radical inhibition medicines 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 the novel diaryl nonane IV and III free radical inhibitor in the saxifraga tangutica is verified:
respectively adding chromatographic methanol into new diaryl nonane type Saxitansin A and Saxitanside B free radical inhibitors in the separated saxitans to dissolve, respectively preparing sample solutions with the concentrations of 0.2mg/mL and 0.1mg/mL, filtering through a 0.45-micrometer microporous filter membrane to obtain new diaryl nonane type Saxitansin A and Saxitanside B sample solutions in the saxistor, taking 1mL of sample, and verifying the activity of the new diaryl nonane type Saxitansin A and Saxitanside B samples in the saxistor by utilizing an online HPLC-DPPH chromatography combined system; in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a pure water resistant reversed phase chromatographic column of 7-X10 (250 multiplied by 4.6mm,7 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 ratio of the mobile phase A to the mobile phase B is 0-60min, the flow rate of the mobile phase is 1.0mL/min, and the detection wavelength is 254nm; a second high performance liquid chromatograph is filled with DPPH solution dissolved in methanol, the concentration of the DPPH solution is 50 mu g/mL, and the flow rate of a mobile phase is 0.5mL/min; the length of the reaction ring is 15m, the detection wavelength is 517nm, and the activity verification chromatogram map (see the attached figures 6 and 7 for details). Mass spectrum, nuclear magnetic diagram, infrared spectrum diagram, ultraviolet spectrum diagram, optical rotation test diagram, CD test diagram and structural diagram of new diaryl nonane Saxitansin A and Saxitanside B free radical inhibitor (see the detailed attached figures 8-32).
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 (5)
1. The separation and preparation process of the new diaryl nonane IV and III free radical inhibitor in the saxifraga tangutica is characterized by comprising the following steps:
step 1, extraction: drying the whole herb of saxifraga tangutica in the shade, coarsely crushing the dried herb, and mixing the crushed herb according to the ratio of 1g of material to liquid: extracting with 5-100 mL of methanol at room temperature for 2-4 times, each time for 2-4 h, filtering, and combining the filtrates to obtain a filtrate A, wherein the filtrate A is prepared from the following raw materials in percentage by weight: mixing the herba Incarvilleae sinensis with 1:5, and drying under reduced pressure to obtain mixed sample of herba Incarvilleae sinensis extract;
step 2, roughly separating the microporous resin columns: mixing a sample with the thalictrum aizoon extract, carrying out medium-pressure chromatographic separation on the sample by using microporous resin, detecting by using an ultraviolet detector with the detection wavelength of 254nm, collecting the fifth main chromatographic peak fraction in a preparative chromatogram, and drying the fraction under reduced pressure to obtain a target component Fr5, wherein the crude separation working parameters of a microporous resin column are as follows: 460mm long and 49mm diameter of chromatographic column, CHP20P as fixed phase of microporous resin column, water as mobile phase A, ethanol as B, chromatographic conditions of 0-120min, 0-100% B, 120-150min, 100% B, sample amount of 40g, flow rate of 30mL/min;
step 3, on-line free radical inhibitor component screening: adding 70-100% methanol into the Thalictrum aquilegifolium target component Fr5 for dissolving, preparing a sample with the concentration of 70.0-120.0 mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a Thalictrum aquilegifolium target component Fr5 sample solution, namely a filtrate B, taking 1mL of the filtrate B, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5 by using an online HPLC-DPPH chromatography combined system; in the on-line HPLC-DPPH chromatography combined system, a first high performance liquid chromatograph adopts a 7-X10, 250X 4.6mm and 7 mu m reversed phase chromatographic column resistant to pure water, and the detection wavelength is 254nm; a second high performance liquid chromatograph is filled with a DPPH solution dissolved in methanol, and the detection wavelength is 517nm;
step 4, high-pressure reversed-phase chromatographic column separation: sample solution B of a Thalictrum tanguticum target component Fr5 in terms of the amount of polyamide: mixing the component sample of the thalictrum alutatum Fr5 =2:1, drying under reduced pressure to obtain the sample mixture of the thalictrum alutatum extract, separating the sample by a preparation column filled with 7-X10 reversed phase filler, detecting by an ultraviolet detector with the detection wavelength of 254nm, collecting a second main chromatographic peak fraction Fr5-2 and a third main chromatographic peak fraction Fr5-3 in a preparation chromatogram, and drying under reduced pressure to obtain a new diaryl nonane free radical inhibitor SaxitansinA with the purity of more than 95%; drying the chromatographic peak fraction Fr5-3 under reduced pressure to obtain a component containing a new diaryl nonane radical inhibitor Saxitanide B; wherein, the working parameters for preparing the high-pressure reversed-phase preparation column are as follows: preparing a column having a length of 250mm and a diameter of 20mm, a stationary phase of 7 μm 7-X10 filler for a reversed phase chromatography column, an aqueous solution for mobile phase A, an acetonitrile solution for mobile phase B, a target component Fr5, which is eluted in a gradient of 0-60min, 10-45% by volume B, a sample amount of 1.0g, a flow rate of 19mL/min;
step 5, on-line free radical inhibitor screening: adding 70-100% methanol into the Thalictrum aquilegifolium target component Fr5-3 for dissolving, preparing a sample with the concentration of 50.0-100.0 mg/mL, filtering by a 0.45-micrometer microporous filter membrane to obtain a solution of the Thalictrum aquilegifolium target component Fr5-3, namely a filtrate C, taking 1mL of the filtrate C, and screening a free radical inhibitor in the Thalictrum aquilegifolium target component Fr5-3 by using an online HPLC-DPPH chromatography combined system; wherein, in the on-line HPLC-DPPH chromatography combined system, the first high performance liquid chromatograph adopts a pure water resistant C18, 250 multiplied by 4.6mm,5 μm reversed phase chromatographic column, and the detection wavelength is 254nm; a second high performance liquid chromatograph enters a DPPH solution dissolved in methanol, and the detection wavelength is 517nm;
step 6, preparing a high-pressure reversed-phase column: separating the filtrate C by a reversed phase C18 preparative column, detecting by an ultraviolet detector with the detection wavelength of 254nm, collecting corresponding chromatographic peak fraction Fr5-3-1 in a preparative chromatogram, and drying the chromatographic peak fraction Fr5-3-1 under reduced pressure to obtain a novel diaryl nonane radical inhibitor Saxitanide B with the purity of more than 95%; wherein, the working parameters for preparing the high-pressure reversed-phase C18 preparation column are as follows: preparing pure water-resistant C18 filler with the column length of 250mm and the diameter of 20mm, the stationary phase of a reversed phase chromatographic column of 5 microns, wherein the mobile phase A is aqueous solution, the mobile phase B is acetonitrile solution, the target component Fr5-3 is eluted according to the isocratic ratio of 0-40min, the concentration of 27 percent B is equal to 1.0mL, and the flow rate is 19mL/min;
wherein, the diaryl nonane Saxitansin A free radical inhibitor and the Saxitanside B free radical inhibitor are respectively named as diaryl nonane IV and III free radical inhibitor, are in brown yellow oil, and have molecular formulas of C 21 H 26 O 6 And C 27 H 36 O 10 The chemical structural formulas are respectively as follows:
2. the process for the isolation and preparation of the novel diarylnonanes IV and III radical inhibitors of saxifraga tangutica as claimed in claim 1, wherein drying under reduced pressure in step 1, step 2, step 4 and step 6 is carried out under the following conditions: the vacuum degree is 50-250 mbar, and the temperature is 40-60 ℃.
3. The process for separating and preparing the novel diarylnonanes IV and III radical inhibitors in saxifraga tangutica as claimed in claim 1, wherein in step 3, the first HPLC uses an aqueous solution as mobile phase A and an acetonitrile solution as mobile phase B, and the ratio of the mobile phase A to the mobile phase B is 0-60min, 10-45% by weight, and the flow rate of the mobile phase is 1.0mL/min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the reaction ring length was 15m.
4. The process for separating and preparing the novel diarylnonanes IV and III radical inhibitors of saxifraga tangutica as claimed in claim 1, wherein in step 5, the first HPLC using mobile phase A of aqueous solution and mobile phase B of acetonitrile solution, the flow rate of mobile phase is 1.0mL/min per 0-40min; the DPPH solution used by the second high performance liquid chromatograph has the concentration of 50 mug/mL and the flow rate of the mobile phase is 0.5mL/min; the reaction ring length was 15m.
5. The process for the isolation and preparation of the novel diarylnonanes IV and III radical inhibitors from saxifraga tangutica as claimed in claim 1, wherein said pure water resistant C18 reverse phase chromatography column in steps 5 and 6 is a pure water resistant Reprosil C18 reverse phase chromatography column or a pure water resistant Megres C18 reverse phase chromatography column.
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| CN109152938A (en) * | 2016-05-03 | 2019-01-04 | 塔德尔玛公司 | For skin makeup or the Herba Saxifragae extract of therapeutical uses |
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