CN109053636B - Method for preparing epoxy carrot olefine aldehyde A and B - Google Patents
Method for preparing epoxy carrot olefine aldehyde A and B Download PDFInfo
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- CN109053636B CN109053636B CN201811164899.5A CN201811164899A CN109053636B CN 109053636 B CN109053636 B CN 109053636B CN 201811164899 A CN201811164899 A CN 201811164899A CN 109053636 B CN109053636 B CN 109053636B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
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- Treatment Of Liquids With Adsorbents In General (AREA)
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Abstract
The invention discloses a method for preparing epoxy carrot enal A and B, which comprises the following steps: step S1, extracting: pulverizing dried rose flower, extracting, filtering, and concentrating the filtrate until no alcohol smell; s2, enriching by macroporous resin to obtain enriched freeze-dried powder rich in epoxy carrot olefine aldehyde A and B; and step S3, separating and purifying the HSCCC by using n-hexane/ethyl acetate/95% ethanol/water with the volume ratio of 9. The method provided by the invention can be used for efficiently separating and purifying the epoxy carrot enal A and B.
Description
Technical Field
The invention belongs to the field of chemistry, and relates to a method for preparing epoxy carrot enal A and epoxy carrot enal B.
Background
The epoxy carrot olefine aldehyde A and B are two compounds separated from a rose with a self-weight petal, and the structural formula is as follows:
epoxydauneral a and B are a pair of isomers differing only in the configuration of the carbon atom to which the epoxy is attached.
Researches show that the epoxy carrot enal A and B have various excellent pharmacological activities and have values of developing various medicaments. However, at present, no method for efficiently separating and purifying the epoxydaucostal A and the epoxydaucostal B exists.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a method for preparing epoxy carrot enal A and B.
The above purpose of the invention is realized by the following technical scheme:
a method for preparing epoxy carrot enal A and B comprises the following steps:
step S1, extracting: pulverizing dried rose flower, extracting, filtering, and concentrating the filtrate until there is no alcohol smell;
step S2, macroporous resin enrichment: loading the concentrated extract without alcohol smell on a DA-201 type macroporous adsorption resin column, wherein the diameter-height ratio of the resin is 1/10, the sample-mixing resin accounts for 1/10 of the total amount of the resin, loading the resin on the column by a wet method, and mixing the resin for loading; eluting with 8BV of 30% ethanol at a flow rate of 8BV/h, eluting with 14BV of 75% ethanol at a flow rate of 8BV/h, collecting 13-14BV of eluate, concentrating until no ethanol smell exists, and freeze-drying to obtain concentrated lyophilized powder;
step S3, HSCCC separation and purification:
s3.1 two-phase solvent system preparation
The two-phase solvent system selects n-hexane/ethyl acetate/95% ethanol/water with the volume ratio of 9.
S3.2 sample solution preparation
And (3) ultrasonically dissolving the enriched freeze-dried powder by using 10mL of upper phase mixed solvent and 10mL of lower phase mixed solvent to prepare a solution with the concentration of 10mg/mL, namely the sample solution.
S3.3HSCCC separation
Pumping the upper phase of the prepared solvent system into an HSCCC spiral pipe to be used as a stationary phase, starting a high-speed counter-current chromatograph when the upper phase is completely filled in the whole column, setting the rotating speed of 900r/min, the volume flow of 1.3mL/min and the detection wavelength of 228nm, pumping the lower phase of the solvent system into the spiral pipe, and indicating that the two-phase solvent in the spiral pipe reaches fluid dynamic balance when the mobile phase begins to continuously flow out from the tail end of the detector; the sample injection valve injects 20mL of sample solution, and the chromatogram recording is started and the mobile phase separation is continuously pumped in.
And S3.4, respectively collecting elution fractions corresponding to the epoxy carrot enal A, B according to the chromatogram, concentrating and drying to respectively obtain epoxy carrot enal A and epoxy carrot enal B.
Preferably, step S1 is extracted with 95% ethanol under hot reflux.
Preferably, the solid-to-liquid ratio extracted in step S1 is 1.
Preferably, step S1 is extracted 3 times, each for 1.5h.
Has the advantages that:
the method provided by the invention can be used for efficiently separating and purifying the epoxy carrot enal A and B.
Drawings
FIG. 1 is a HSCCC separation chromatogram;
FIG. 2 is a HPLC chromatogram for detecting the purity of epoxy carrot enal A;
FIG. 3 is a HPLC chromatogram for detecting the purity of the epoxy carrot enal B.
Detailed Description
The following examples are given to illustrate the essence of the present invention, but not to limit the scope of the present invention.
1. Experimental materials
The rose with double petals is a flower of the rose with double petals, and is dried in the shade after being picked fresh for later use.
DA-201 macroporous resin was purchased from Tianjin Haoyao resin technology, inc.
High-speed countercurrent chromatography TEB300B is available from Shanghai Hotan Biotechnology GmbH.
2. Experimental methods and results
The method comprises the following steps:
step S1, extracting: pulverizing dried rose, extracting with 95% ethanol water solution at a solid-to-liquid ratio of 1;
step S2, macroporous resin enrichment: loading the concentrated extract without alcohol smell on a DA-201 type macroporous adsorption resin column, wherein the diameter-height ratio of the resin is 1/10, the sample-mixing resin accounts for 1/10 of the total amount of the resin, loading the resin in the column by a wet method, and mixing the resin for loading; eluting with 8BV of 30% ethanol at a flow rate of 8BV/h, eluting with 14BV of 75% ethanol at a flow rate of 8BV/h, collecting 13-14BV of eluate, concentrating until no ethanol smell exists, and freeze-drying to obtain concentrated lyophilized powder;
step S3, HSCCC separation and purification:
s3.1 two-phase solvent system preparation
The two-phase solvent system selects n-hexane/ethyl acetate/95% ethanol/water with the volume ratio of 9.
S3.2 sample solution preparation
And (3) ultrasonically dissolving the enriched freeze-dried powder by using 10mL of upper phase mixed solvent and 10mL of lower phase mixed solvent to prepare a solution with the concentration of 10mg/mL, namely the sample solution.
S3.3HSCCC separation
Pumping the upper phase of the prepared solvent system into an HSCCC spiral pipe to be used as a stationary phase, starting a high-speed counter-current chromatograph when the upper phase is completely filled in the whole column, setting the rotating speed of 900r/min, the volume flow of 1.3mL/min and the detection wavelength of 228nm, pumping the lower phase of the solvent system into the spiral pipe, and indicating that the two-phase solvent in the spiral pipe reaches fluid dynamic balance when the mobile phase begins to continuously flow out from the tail end of the detector; the sample injection valve injects 20mL of sample solution, and the chromatogram recording is started and the mobile phase separation is continuously pumped in.
S3.4 according to the chromatogram (figure 1), respectively collecting elution fractions corresponding to the epoxy carrot olefine aldehyde A, B, concentrating and drying to respectively obtain epoxy carrot olefine aldehyde A and epoxy carrot olefine aldehyde B with the purities of 98.5% and 98.9%.
The comparison of the epoxycarrot enal A, B prepared by HSCCC separation and the standard substance has the same HPLC chromatographic retention behavior, and the HPLC chromatograms are shown in FIGS. 2 and 3.
The above examples are only for illustrating the essence of the present invention, but not for limiting the scope of the present invention.
Claims (3)
1. A method for preparing epoxycarrot enal A and epoxycarrot enal B is characterized by comprising the following steps:
step S1, extracting: pulverizing dried rose, extracting with 95% ethanol under reflux, filtering, and concentrating the filtrate until there is no alcohol smell;
step S2, macroporous resin enrichment: loading the concentrated extract without alcohol smell on a DA-201 type macroporous adsorption resin column, wherein the diameter-height ratio of the resin is 1/10, the sample-mixing resin accounts for 1/10 of the total amount of the resin, loading the resin on the column by a wet method, and mixing the resin for loading; eluting with 8BV of 30% ethanol at a flow rate of 8BV/h, eluting with 14BV of 75% ethanol at a flow rate of 8BV/h, collecting 13-14BV of eluate, concentrating until no ethanol smell exists, and freeze-drying to obtain concentrated lyophilized powder;
step S3, HSCCC separation and purification:
s3.1 two-phase solvent system preparation
Selecting n-hexane/ethyl acetate/95% ethanol/water with the volume ratio of 9;
s3.2 preparation of sample solution
Ultrasonically dissolving the enriched freeze-dried powder with 10mL of upper phase mixed solvent and 10mL of lower phase mixed solvent to prepare a solution with the concentration of 10mg/mL, namely a sample solution;
s3.3HSCCC separation
Pumping the upper phase of the prepared solvent system into an HSCCC spiral pipe to be used as a stationary phase, starting a high-speed counter-current chromatograph when the upper phase is completely filled in the whole column, setting the rotating speed of 900r/min, the volume flow of 1.3mL/min and the detection wavelength of 228nm, pumping the lower phase of the solvent system into the spiral pipe, and indicating that the two-phase solvent in the spiral pipe reaches fluid dynamic balance when the mobile phase begins to continuously flow out from the tail end of the detector; injecting 20mL of sample solution into the sample injection valve, starting to record a chromatogram and continuously pumping into a flowing phase for separation;
and S3.4, respectively collecting elution fractions corresponding to the epoxy carrot enal A and the epoxy carrot enal B according to the chromatogram, and concentrating and drying to respectively obtain the epoxy carrot enal A and the epoxy carrot enal B.
2. The method of claim 1, wherein: the solid-liquid ratio extracted in the step S1 is 1.
3. The method of claim 1, wherein: step S1, extracting for 3 times, and each time for 1.5h.
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| CN110963920B (en) * | 2019-12-17 | 2022-05-20 | 车国娟 | Preparation method of magnolia liliflora alcohol B |
| CN110963919B (en) * | 2019-12-17 | 2022-11-01 | 滕州鑫和生物科技有限公司 | Preparation method of magnolia liliflora alcohol A |
Citations (3)
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| CN104277085A (en) * | 2013-07-11 | 2015-01-14 | 江南大学 | Method for simultaneously separating four sedum purpureum flavones by employing online two-dimensional serial chromatography technology |
| CN104630289A (en) * | 2015-01-12 | 2015-05-20 | 安徽华业香料股份有限公司 | Synthesis method of (S)-(-)-alpha-damascenone |
| CN108373457A (en) * | 2018-04-23 | 2018-08-07 | 中国科学院烟台海岸带研究所 | A kind of epoxy sesquiterpenoids and its preparation and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1230160C (en) * | 2003-05-25 | 2005-12-07 | 杭州浙大力夫生物科技有限公司 | Application of bamboo leaf total flavone in medicine for treating and preventing prostata disease and health-care-food |
| EP2364083A4 (en) * | 2008-12-10 | 2012-10-31 | Metaproteomics Llc | A method for the purification of substituted cyclopent-2-en-1-one congeners and substituted 1,3-cyclopentadione congeners from a complex mixture using countercurrent separation |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104277085A (en) * | 2013-07-11 | 2015-01-14 | 江南大学 | Method for simultaneously separating four sedum purpureum flavones by employing online two-dimensional serial chromatography technology |
| CN104630289A (en) * | 2015-01-12 | 2015-05-20 | 安徽华业香料股份有限公司 | Synthesis method of (S)-(-)-alpha-damascenone |
| CN108373457A (en) * | 2018-04-23 | 2018-08-07 | 中国科学院烟台海岸带研究所 | A kind of epoxy sesquiterpenoids and its preparation and application |
Non-Patent Citations (2)
| Title |
|---|
| CAROTANOIDS AND AN ACORANOID FROM ROSA RUGOSA LEAVES;YASUYUKI HASHIDOKO等;《Phytochemistry》;19911231;第30卷(第11期);第3729页左栏第1行-第3738页右栏第10行，Fig.1 * |
| 高速逆流色谱制备玫瑰红景天中的三种酚性化合物;马朝阳等;《天然产物研究与开发》;20121231;第24卷;第1787-1790页 * |
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