CN103265521A - Preparation method of demethylated beilidifolin - Google Patents
Preparation method of demethylated beilidifolin Download PDFInfo
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- CN103265521A CN103265521A CN 201310199325 CN201310199325A CN103265521A CN 103265521 A CN103265521 A CN 103265521A CN 201310199325 CN201310199325 CN 201310199325 CN 201310199325 A CN201310199325 A CN 201310199325A CN 103265521 A CN103265521 A CN 103265521A
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Abstract
The invention discloses a preparation method of demethylated beilidifolin. The method comprises the following steps of: (1) taking coarse powder of Swertia david i Franch, adding a 50-70% ethanol liquid and heating to 60-80 DEG C, dynamically extracting for 2-4 hours, filtering, decompressing the filtrate till no ethanol exists to obtain concentrated liquor; (2) enabling the concentrated liquor to flow through a macroporous adsorbent resin column, eluting by water and ethanol liquor, and concentrating the alcohol eluent to obtain concentrated liquor; and (3) further adding the concentrated liquor to the macroporous resin for adsorption, eluting by 10 times of 50% ethanol liquor, collecting 6 times of eluent in volume, decompressing the eluent to recover the reagent, placing and crystallizing, backflow-dissolving and crystallizing coarse crystals by absolute ethyl alcohol and drying to obtain the demethylated beilidifolin. According to the method for preparing demethylated beilidifolin, the purity of the product obtained is high, and the method is beneficial for industrial amplification.
Description
Technical field
The invention belongs to the Natural Medicine Chemistry field, particularly a kind of preparation method of Norbellidifodin.
Background technology
Norbellidifodin, CAS 2980-32-7, molecular formula C
13H
18O
6, molecular weight 260.2, molecular structural formula is as follows:
Norbellidifodin is a kind of (mouthful mountain) ketone material, has the protection vascular endothelial cell, effects such as protection ischemic myocardium and hypoglycemic.
By literature search, existing preparation Norbellidifodin method adopts silica gel column chromatography more.Be to adopt supercritical CO as document " research of Herba Swertiae bimaculatae (mouthful mountain) ketone " disclosed method
2Extraction, and then adopt silica gel column chromatography.This method complicated operation yields poorly, and is fit to be not suitable for suitability for industrialized production.
Summary of the invention
The objective of the invention is to solve the deficiencies in the prior art and defective, a kind of simple to operate, Norbellidifodin preparation method that yield is high is provided.
For achieving the above object, the technical solution used in the present invention is as follows:
A kind of preparation method of Norbellidifodin is characterized in that it may further comprise the steps:
(1) get the Herba Swertiae bimaculatae meal, add the 50-70% ethanolic soln and be heated to 60 ℃-80 ℃, dynamic extraction 2-4 hour, leach, filtrate decompression is to there not being the pure concentrated solution that gets;
(2) above-mentioned concentrated solution is crossed macroporous adsorptive resins, water and ethanolic soln wash-out, alcohol eluen obtains concentrated solution after concentrating;
(3) get concentrated solution and add in the macroporous resin again and adsorb, with the ethanolic soln wash-out of 10 times of amounts 50%, collect back 6 times of volume elutriants, elutriant reclaim under reduced pressure reagent is placed crystallization, and coarse crystallization refluxes dissolving crystallized again with dehydrated alcohol, be drying to obtain.
Nonpolar or low-pole macroporous adsorbent resins such as the optional HZ816 of macroporous resin, AB-8, D101, HPD500 described in step (2), (3).
The described macroporous adsorbent resin wash-out of step (2) is 50-70% with volumes of aqueous ethanol per-cent, and the wash-out consumption is 5-10 times of column volume.
Adopt this method to prepare Norbellidifodin, production technique is easy, easily realizes suitability for industrialized production.
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to the following example.
Embodiment:
Embodiment 1:
Get 5kg Herba Swertiae bimaculatae meal, the mass ratio of pressing 1:5 adds 60% ethanolic soln, dynamic extraction is 3 hours after being heated to 60 ℃, extract 3 times, filter decompression filtrate recycling ethanol, concentrated solution adds in the HZ816 macroporous adsorptive resins and adsorbs, wash with water to elutant colourlessly earlier, washing lotion discards, and 50% ethanolic soln with 10 times of column volumes carries out wash-out again, collect elutriant, concentrating under reduced pressure, concentrated solution add again in the HZ816 macroporous resin column and adsorb, with the ethanolic soln wash-out of 10 times of amounts 50%, collect back 6 times of volume elutriants, elutriant reclaim under reduced pressure reagent is placed crystallization, and coarse crystallization refluxes dissolving crystallized 2 times with dehydrated alcohol again, the dry pale yellow powder Norbellidifodin 23g that gets, detect through HPLC, content 97.5% is through UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Embodiment 2:
Get 5kg Herba Swertiae bimaculatae meal, the mass ratio of pressing 1:6 adds 70% ethanolic soln, dynamic extraction is 2 hours after being heated to 70 ℃, extract 2 times, filter decompression filtrate recycling ethanol, concentrated solution adds in the AB-8 macroporous adsorptive resins and adsorbs, wash with water to elutant colourlessly earlier, washing lotion discards, and 70% ethanolic soln with 8 times of column volumes carries out wash-out again, collect elutriant, concentrating under reduced pressure, concentrated solution add again in the AB-8 macroporous resin column and adsorb, with the ethanolic soln wash-out of 10 times of amounts 50%, collect back 6 times of volume elutriants, elutriant reclaim under reduced pressure reagent is placed crystallization, and coarse crystallization refluxes dissolving crystallized 3 times with dehydrated alcohol again, the dry pale yellow powder Norbellidifodin 22g that gets, detect through HPLC, content 98.1% is through UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Embodiment 3:
Get 5kg Herba Swertiae bimaculatae meal, the mass ratio of pressing 1:8 adds 65% ethanolic soln, dynamic extraction is 3 hours after being heated to 70 ℃, extract 2 times, filter decompression filtrate recycling ethanol, concentrated solution adds in the HPD500 macroporous adsorptive resins and adsorbs, wash with water to elutant colourlessly earlier, washing lotion discards, and 50% ethanolic soln with 10 times of column volumes carries out wash-out again, collect elutriant, concentrating under reduced pressure, concentrated solution add again in the HZ816 macroporous resin column and adsorb, with the ethanolic soln wash-out of 10 times of amounts 50%, collect back 6 times of volume elutriants, elutriant reclaim under reduced pressure reagent is placed crystallization, and coarse crystallization refluxes dissolving crystallized 3 times with dehydrated alcohol again, the dry pale yellow powder Norbellidifodin 25g that gets, detect through HPLC, content 97.9% is through UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Claims (3)
1. the preparation method of a Norbellidifodin is characterized in that it may further comprise the steps:
(1) get the Herba Swertiae bimaculatae meal, add the 50-70% ethanolic soln and be heated to 60 ℃-80 ℃, dynamic extraction 2-4 hour, leach, filtrate decompression is to there not being the pure concentrated solution that gets;
(2) above-mentioned concentrated solution is crossed macroporous adsorptive resins, water and ethanolic soln wash-out, alcohol eluen obtains concentrated solution after concentrating;
(3) get concentrated solution and add in the macroporous resin again and adsorb, with the ethanolic soln wash-out of 10 times of amounts 50%, collect back 6 times of volume elutriants, elutriant reclaim under reduced pressure reagent is placed crystallization, and coarse crystallization refluxes dissolving crystallized again with dehydrated alcohol, be drying to obtain.
2. the preparation method of Norbellidifodin according to claim 1 is characterized in that nonpolar or low-pole macroporous adsorbent resins such as the optional HZ816 of macroporous resin, AB-8, D101, HPD500 described in step (2), (3).
3. the preparation method of Norbellidifodin according to claim 1 is characterized in that the described macroporous adsorbent resin wash-out of step (2) is 50-70% with volumes of aqueous ethanol per-cent, and the wash-out consumption is 5-10 times of column volume.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 201310199325 CN103265521A (en) | 2013-05-27 | 2013-05-27 | Preparation method of demethylated beilidifolin |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104497005A (en) * | 2014-12-30 | 2015-04-08 | 云南中医学院 | Swertiamarin thermal conversion product, as well as preparation method, preparation and application thereof |
| CN104497004A (en) * | 2014-12-30 | 2015-04-08 | 云南中医学院 | Method for preparing swertia lactone I-K |
| CN107880010A (en) * | 2017-11-20 | 2018-04-06 | 成都瑞芬思生物科技有限公司 | A kind of preparation method of demethyl young bird leaf gentisin and young leaf gentisin |
| CN111184763A (en) * | 2020-01-18 | 2020-05-22 | 黑龙江中医药大学 | Swertia yunnanensis extract and application thereof |
-
2013
- 2013-05-27 CN CN 201310199325 patent/CN103265521A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104497005A (en) * | 2014-12-30 | 2015-04-08 | 云南中医学院 | Swertiamarin thermal conversion product, as well as preparation method, preparation and application thereof |
| CN104497004A (en) * | 2014-12-30 | 2015-04-08 | 云南中医学院 | Method for preparing swertia lactone I-K |
| CN107880010A (en) * | 2017-11-20 | 2018-04-06 | 成都瑞芬思生物科技有限公司 | A kind of preparation method of demethyl young bird leaf gentisin and young leaf gentisin |
| CN111184763A (en) * | 2020-01-18 | 2020-05-22 | 黑龙江中医药大学 | Swertia yunnanensis extract and application thereof |
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Application publication date: 20130828 |