CN103788037A - Method for purifying carabrone - Google Patents
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- CN103788037A CN103788037A CN201210434466.3A CN201210434466A CN103788037A CN 103788037 A CN103788037 A CN 103788037A CN 201210434466 A CN201210434466 A CN 201210434466A CN 103788037 A CN103788037 A CN 103788037A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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Abstract
The invention discloses a method for purifying carabrone. The method comprises the following steps: (1) soaking or ultrasonically extracting carpesium abrotanoides in a water solution of inorganic strong base at 0-100 DEG C; then, filtering, adjusting the pH value of filter liquor to be 1-7 by the inorganic strong base to generate deposits; (2) removing the deposits generated in the step (1), and then extracting supernatant liquid by an organic solvent to obtain extracting liquid; and (3) performing silica column chromatography on the extracting liquid obtained from the step (2) to obtain the carabrone. The method is easy to operate; the obtained carabrone is relatively high in purity.
Description
Technical field
The present invention is specifically related to a kind of method of purification of Carabrone.
Background technology
FRUCTUS CARPESII is the dry mature fruit of feverfew root of Common carpesium, has the effect of killing insect and eliminating accumulation, is usually used in treating roundworm, pinworm, teniasis, abdominal pain due to worm stagnation and infantile malnutrition etc.This field is fewer for the research of FRUCTUS CARPESII chemical composition, current research shows, FRUCTUS CARPESII contains Telekin (Liu Cuizhou, Xu Jing, Gui Liping etc. the chemical constitution study [J] of FRUCTUS CARPESII. drug evaluation research, 2010,33 (6): 220-221), Carabrone, carpesia-lactone alcohol and various lipid acid.Research shows, Carabrone belongs to sesquiterpenoids, has sterilization and bacteriostasis effect, in order to realize its good fungistatic effect, and need to be by its separation and purification from FRUCTUS CARPESII.Owing to containing a lot of similar carpesia-lactone compounds in FRUCTUS CARPESII, polarity difference is very little each other, make the separation of monomeric compound more difficult, if application number is 201010113236, name is called the Chinese invention patent of " a kind of Carpesium abrotanoides total terpene lactones extract ", and a kind of extract Carpesium abrotanoides total terpene lactones compound from root of Common carpesium method is provided.What this invention obtained is Carpesium abrotanoides total terpene lactones mixture, and Carabrone, carpesia-lactone alcohol purity are wherein not high, can not meet the demand of real scientific research, production.
Summary of the invention
Technical problem to be solved by this invention is in the method in order to overcome existing purification Carabrone, the defect that Carabrone purity is not high, and a kind of Carabrone method of purification is provided.Method of purification of the present invention is simple to operate, and the Carabrone purity obtaining is higher.
The method of purification that the invention provides a kind of Carabrone, it comprises the following step:
Step 1): in the aqueous solution of inorganic strong alkali, under 0～100 ℃ of condition, FRUCTUS CARPESII is being soaked or supersound extraction; Then filter, filtrate regulates pH to 1 ~ 7 with inorganic acid, produces precipitation;
Step 2): the precipitation that step 1) is produced extracts supernatant liquor after removing with organic solvent, obtain extraction liquid;
Step 3): by step 2) extraction liquid that obtains carries out silica gel column chromatography, gets final product to obtain Carabrone.
In step 1), described soak or the temperature of supersound extraction is preferably 30 ~ 70 ℃.The time of described immersion is preferably 1h ~ 24h.The time of described supersound extraction is preferably 5 ~ 60 minutes, and better is 10 ~ 15 minutes.The number of times of described supersound extraction is preferably 1 ~ 3 time.The pressure of supersound extraction is preferably 0.1 ~ 10.0MPa.In step 1), adopt supersound process, can shorten extraction time, improve extraction efficiency.
In step 1), described pH is preferably 1 ~ 3.The mass ratio of described FRUCTUS CARPESII and the aqueous solution of inorganic strong alkali is preferably 1:1 ~ 1:30, and that better is 1:10 ~ 1:15.Described inorganic strong alkali is preferably NaOH and/or KOH.In the aqueous solution of described inorganic strong alkali, the mass concentration of inorganic strong alkali is preferably 0.1% ~ 20%, preferably 0.1% ~ 10%, further preferably 0.5% ~ 1%.Described inorganic acid is preferably one or more in hydrochloric acid, sulfuric acid and nitric acid, and better is hydrochloric acid, and hydrochloric acid preferably exists (the preferably aqueous hydrochloric acid of hydrochloric acid mass concentration as 0.1% ~ 1%) take the form of aqueous hydrochloric acid.While regulating pH with inorganic acid, the temperature of the solution regulating is preferably room temperature, 0 ~ 40 ℃.In the present invention, step 1) adopts alkali-acid treatment impurity, makes impurity-removing method simple, economical.
Step 2) in, the method for removing precipitation can be centrifugal, or by leaving standstill and filtering.Described organic solvent during supernatant liquor is extracted with organic solvent can be conventional extraction use, with the immiscible organic solvent of water, one or more in ethyl acetate, methylene dichloride, carbon trichloride and tetracol phenixin.
In step 3), the method of described silica gel column chromatography and condition all can be ordinary method and the condition of this type of separation method of this area, those skilled in the art (can be using existing Carabrone as standard substance in the present invention according to the polarity of target product, by the isolated material of control test), in conjunction with methods such as TLC detections, can select the condition that target product Carabrone of the present invention is purified.The present invention is following method and condition particularly preferably: eluent used is preferably ether-acetone, or methylene chloride-methanol; Wherein, elution requirement is Gradient elution, and in described ether-acetone, the volume ratio of ether and acetone is preferably the preferred 4:1 ~ 6:1 of 10:0 ~ 0:10().In described methylene chloride-methanol, the volume ratio of methylene dichloride and methyl alcohol is preferably the preferred 95:5 of 100:0 ~ 0:100().Silica gel in silica gel column chromatography used can be macroporous silica gel, silochrom, Type B silica gel or Kiselgel A.Preferably, in elution process, elutriant is put to thin-layer silicon offset plate (TLC), developping agent can be ether-acetone (2:1 ~ 4:1), and developer can be 5% sulphuric acid soln, can be in 105 ℃ of heating 5min colour developing, collecting appears starting in first round dot, merge the elutriant of first round dot, concentrate, fling to organic solvent, get final product to obtain Carabrone.
In the present invention, preferably, after step 3), can also comprise the following step 4):
Step 4): the Carabrone that step 3) is made is dissolved in the mixing solutions of low polar solvent and high polar solvent, being concentrated into clear crystal separates out, can obtain more highly purified Carabrone, wherein low polar solvent is ether, hexane, hexanaphthene, methylene dichloride or pentane, and high polar solvent is acetone, ethyl acetate, chloroform, methyl alcohol or ethanol.
In step 4), preferably, the mixing solutions of low polar solvent and high polar solvent is ether-acetone mixing solutions, hexanaphthene-acetone mixing solutions, or hexanaphthene-ethyl acetate mixture.In described ether-acetone mixing solutions, the volume ratio of ether and acetone be preferably 4:1 ~ 10:1(better for 8:1).In described hexanaphthene-acetone mixing solutions, the volume ratio of hexanaphthene and acetone be preferably 4:1 ~ 10:1(better for 8:1).In described hexanaphthene-ethyl acetate mixture, the volume ratio of hexanaphthene and ethyl acetate be preferably 4:1 ~ 10:1(better for 8:1).
Without prejudice to the field on the basis of common sense, above-mentioned each optimum condition, can arbitrary combination, obtains the present invention.
Agents useful for same of the present invention and raw material be commercially available obtaining all.
Positive progressive effect of the present invention is: method of purification of the present invention is simple to operate, and the Carabrone purity obtaining is higher.
Accompanying drawing explanation
Fig. 1 is the schematic flow sheet of the preferred embodiments of the method for purification of Carabrone of the present invention.
Fig. 2 is the final product Carabrone that makes of embodiment 1
1hNMR spectrogram.
Embodiment
Mode below by embodiment further illustrates the present invention, but does not therefore limit the present invention among described scope of embodiments.The experimental technique of unreceipted actual conditions in the following example, according to ordinary method and condition, or selects according to catalogue.
Embodiment 1
The preparation technology of Carabrone, take FRUCTUS CARPESII as raw material, 0.5%NaOH solution is extraction agent, extracts the technique that separates Carabrone, concrete steps are as follows:
(1) get 1kg FRUCTUS CARPESII, use 5L 0.5%(w/w) NaOH solution, 30 ℃ of supersound process 30min, separate FRUCTUS CARPESII with 200 object filter clothes, use again 4L 0.5%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 object filter clothes; Use again 3L 0.5%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 order filter clothes; Merge the extracting solution extracting for three times.
(2) in extracting solution, adding 1%(w/w) hydrochloric acid soln neutralizes under room temperature (25 ℃) condition, adjusts pH to 3 left and right, produces precipitation, leave standstill.
(3) sinking to the bottom with supernatant liquor of generation separated, precipitate heavy multiple (1), (2) step; Supernatant liquor adds 1L ethyl acetate to extract, and extracts three times, merges the extraction liquid of three times, concentrated.
(4) by silicagel column on the ethyl acetate extract after concentrated, carry out Gradient elution with ether-acetone mixed solution, wherein, ether-acetone volume ratio is 4:1.In elution process, adopt stepwise elution, with silica gel thin-layer plate with ether-acetone developping agent expansion, carry out qualitative test, will contain same compound and put to such an extent that elutriant merges.Wherein, will only put to such an extent that elutriant concentrates, reclaims eluent containing first, and obtain Carabrone 3.75g, purity be more than 90%.
(5) Carabrone of acquisition is dissolved in to ether-acetone (V/V, volume ratio 8:1), is concentrated into and occurs white opacity, have colourless crystallization, dry, obtain more than 99.5% Carabrone of 3.65g purity.
The nuclear magnetic spectrogram of product Carabrone is as Fig. 1, and concrete data are as follows:
1HNMR（CDCl
3）δH：6.23(1H，d，J=2.8Hz，H-13)，5.56(1H，d，J=2.4Hz，H-13')，4.79（1H，ddd，J=6，g，11，11.4Hz，H-8)，3.15(1H，ddddd，J=7，9，13Hz，H-7)，2.16(3H，s，H-15)，1.08(3H，s，H-1.4)，0.45(1H，m，H-5)，0.37(1H，m，H-1)。
Embodiment 2
(1) get 5kg FRUCTUS CARPESII, use 20L 1%(w/w) NaOH solution, 30 ℃ of supersound process 30min, separate FRUCTUS CARPESII with 200 object filter clothes, use again 15L 1%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 object filter clothes; Use again 10L 1%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 order filter clothes; Merge the extracting solution extracting for three times.
(2) in extracting solution, adding 3%(w/w) hydrochloric acid soln neutralizes under room temperature (25 ℃) condition, adjusts pH to 2 left and right, produces precipitation, leave standstill.
(3) sinking to the bottom with supernatant liquor of generation separated, precipitate heavy answering (1), (2) step; Supernatant liquor adds 2.5L ethyl acetate to extract, and extracts three times, merges the extraction liquid of three times, concentrated.
(4) by silicagel column on the ethyl acetate extract after concentrated, carry out Gradient elution with methylene chloride-methanol mixed solution, wherein, methylene chloride-methanol volume ratio is 95:5.In elution process, adopt stepwise elution, with silica gel thin-layer plate launch take ether-acetone as developping agent, qualitative test, by the elutriant merging that contains same compound.By concentrated the elutriant that only contains first compound, recovery eluent, obtain Carabrone 16.35g, purity is more than 90%.
(5) Carabrone of acquisition is dissolved in to hexanaphthene-acetone (V/V, volume ratio 8:1), is concentrated into and occurs white opacity, leave standstill, have crystallization, dry, obtain 15.95g purity and reach more than 99.5% Carabrone.
The nuclear magnetic data of product Carabrone is as follows:
1HNMR（CDCl
3）δH：6.23(1H，d，J=2.8Hz，H-13)，5.56(1H，d，J=2.4Hz，H-13')，4.79（1H，ddd，J=6，g，11，11.4Hz，H-8)，3.15(1H，ddddd，J=7，9，13Hz，H-7)，2.16(3H，s，H-15)，1.08(3H，s，H-1.4)，0.45(1H，m，H-5)，0.37(1H，m，H-1)。
Embodiment 3
(1) get 10kg FRUCTUS CARPESII, use 25L 2%(w/w) NaOH solution, 30 ℃ of supersound process 30min, separate FRUCTUS CARPESII with 200 object filter clothes, use again 20L 2%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 object filter clothes; Use again 15L 2%(w/w) NaOH solution is at 30 ℃ of supersound process 30min, FRUCTUS CARPESII separated with 200 order filter clothes; Merge the extracting solution extracting for three times.
(2) in Fructus Carpesii extract filtrate, adding 6%(w/w northwards) hydrochloric acid soln neutralizes under room temperature (25 ℃) condition, adjusts pH to 1 left and right, produces precipitation, leave standstill.
(3) sinking to the bottom with supernatant liquor of generation separated, precipitation repeats (1) (2) step; Supernatant liquor adds 4L ethyl acetate to extract, and extracts three times, merges the extraction liquid of three times, concentrated.
(4) by silicagel column on the ethyl acetate extract after concentrated, carry out Gradient elution with ether-acetone mixed solution, wherein, ether-acetone volume ratio is 4:1.In elution process, adopt stepwise elution, with silica gel thin-layer plate launch take ether-acetone as developping agent, qualitative test, by the elutriant merging that contains same compound.Wherein, by concentrated the elutriant that only contains first compound, recovery eluent, obtain Carabrone 29.6g, purity is more than 90%.
(5) Carabrone of acquisition is dissolved in to hexanaphthene and ethyl acetate (V/V, volume ratio 4:1), is concentrated into and occurs white opacity, leave standstill, have crystallization, dry gained crystallization, obtains 28.56g purity and reaches more than 99.5% Carabrone.
The nuclear magnetic data of product Carabrone is as follows:
1HNMR（CDCl
3）δH：6.23(1H，d，J=2.8Hz，H-13)，5.56(1H，d，J=2.4Hz，H-13')，4.79（1H，ddd，J=6，g，11，11.4Hz，H-8)，3.15(1H，ddddd，J=7，9，13Hz，H-7)，2.16(3H，s，H-15)，1.08(3H，s，H-1.4)，0.45(1H，m，H-5)，0.37(1H，m，H-1)。
Claims (10)
1. a method of purification for Carabrone, is characterized in that comprising the following step:
Step 1): in the aqueous solution of inorganic strong alkali, under 0 ~ 100 ℃ of condition, FRUCTUS CARPESII is being soaked or supersound extraction; Then filter, filtrate regulates pH to 1 ~ 7 with inorganic acid, produces precipitation;
Step 2): the precipitation that step 1) is produced extracts supernatant liquor after removing with organic solvent, obtain extraction liquid;
Step 3): by step 2) extraction liquid that obtains carries out silica gel column chromatography, gets final product to obtain Carabrone.
2. method of purification as claimed in claim 1, is characterized in that: in step 1), and described soak or the temperature of supersound extraction is 30 ~ 70 ℃; The time of described immersion is 1h ~ 24h; The time of described supersound extraction is 5 ~ 60 minutes; The number of times of described supersound extraction is 1 ~ 3 time.
3. method of purification as claimed in claim 1, is characterized in that: in step 1), described pH is 1 ~ 3.
4. method of purification as claimed in claim 1, is characterized in that: in step 1), the mass ratio of described FRUCTUS CARPESII and the aqueous solution of inorganic strong alkali is 1:1 ~ 1:30; Described inorganic strong alkali is NaOH and/or KOH; In the aqueous solution of described inorganic strong alkali, the mass concentration of inorganic strong alkali is 0.1% ~ 20%; Described inorganic acid is one or more in hydrochloric acid, sulfuric acid and nitric acid.
5. method of purification as claimed in claim 4, is characterized in that: in step 1), in the aqueous solution of described inorganic strong alkali, the mass concentration of inorganic strong alkali is 0.1% ~ 10%.
6. method of purification as claimed in claim 1, is characterized in that: in step 1), while regulating pH with inorganic acid, the temperature of the solution regulating is 0 ~ 40 ℃.
7. method of purification as claimed in claim 1, is characterized in that: step 2) in, described organic solvent during supernatant liquor is extracted with organic solvent is one or more in ethyl acetate, methylene dichloride, carbon trichloride and tetracol phenixin.
8. method of purification as claimed in claim 1, is characterized in that: in step 3), in described silica gel column chromatography, eluent used is ether-acetone, or methylene chloride-methanol; Wherein, elution requirement is Gradient elution, and in described ether-acetone, the volume ratio of ether and acetone is 10:0 ~ 0:10; In described methylene chloride-methanol, the volume ratio of methylene dichloride and methyl alcohol is 100:0 ~ 0:100.
9. method of purification as claimed in claim 1, is characterized in that: after step 3), also comprise the following step 4):
Step 4): the Carabrone that step 3) is made is dissolved in the mixing solutions of low polar solvent and high polar solvent, is concentrated into clear crystal and separates out; Wherein low polar solvent is ether, hexane, hexanaphthene, methylene dichloride or pentane, and high polar solvent is acetone, ethyl acetate, chloroform, methyl alcohol or ethanol.
10. method of purification as claimed in claim 9, it is characterized in that: in step 4), the mixing solutions of low polar solvent and high polar solvent is ether-acetone mixing solutions, hexanaphthene-acetone mixing solutions, or hexanaphthene-ethyl acetate mixture, in described ether-acetone mixing solutions, the volume ratio of ether and acetone is 4:1 ~ 10:1; In described hexanaphthene-acetone mixing solutions, the volume ratio of hexanaphthene and acetone is 4:1 ~ 10:1; In described hexanaphthene-ethyl acetate mixture, the volume ratio of hexanaphthene and ethyl acetate is 4:1 ~ 10:1.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105900994A (en) * | 2016-05-21 | 2016-08-31 | 泉州绿邦贸易有限公司 | Sterilization composition containing carabrone and prothioconazole |
| CN105994342A (en) * | 2016-05-21 | 2016-10-12 | 泉州绿邦贸易有限公司 | Sterilization composition containing botanical bactericide |
| CN106138079A (en) * | 2016-07-29 | 2016-11-23 | 甘肃新天马制药股份有限公司 | A kind of liniment treating animal body surface parasitic disease and preparation method thereof |
| CN111574353A (en) * | 2020-05-22 | 2020-08-25 | 丽水市中心医院 | Phenolic compound |
| CN112263600A (en) * | 2020-10-27 | 2021-01-26 | 湖南省中医药研究院 | Carpesium abrotanoides extract, preparation method and application thereof in anti-liver cancer active drugs passing through JAK2/STAT3 channel |
| CN112402412A (en) * | 2020-11-18 | 2021-02-26 | 中国医学科学院药用植物研究所 | Application of inner ester compound of jingdao in preparing medicine for treating inflammation-caused diseases |
| CN113288893A (en) * | 2021-07-02 | 2021-08-24 | 中国科学院兰州化学物理研究所 | Application of sesquiterpene lactone compounds in preparation of medicines for treating renal anemia |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105900994A (en) * | 2016-05-21 | 2016-08-31 | 泉州绿邦贸易有限公司 | Sterilization composition containing carabrone and prothioconazole |
| CN105994342A (en) * | 2016-05-21 | 2016-10-12 | 泉州绿邦贸易有限公司 | Sterilization composition containing botanical bactericide |
| CN106138079A (en) * | 2016-07-29 | 2016-11-23 | 甘肃新天马制药股份有限公司 | A kind of liniment treating animal body surface parasitic disease and preparation method thereof |
| CN106138079B (en) * | 2016-07-29 | 2018-08-24 | 甘肃新天马制药股份有限公司 | A kind of liniment and preparation method thereof for treating animal body surface parasitic disease |
| CN111574353A (en) * | 2020-05-22 | 2020-08-25 | 丽水市中心医院 | Phenolic compound |
| CN111574353B (en) * | 2020-05-22 | 2022-10-25 | 丽水市中心医院 | Phenolic compound |
| CN112263600A (en) * | 2020-10-27 | 2021-01-26 | 湖南省中医药研究院 | Carpesium abrotanoides extract, preparation method and application thereof in anti-liver cancer active drugs passing through JAK2/STAT3 channel |
| CN112263600B (en) * | 2020-10-27 | 2022-07-05 | 湖南省中医药研究院 | Carpesium abrotanoides extract, preparation method and application thereof in anti-liver cancer active drugs passing through JAK2/STAT3 channel |
| CN112402412A (en) * | 2020-11-18 | 2021-02-26 | 中国医学科学院药用植物研究所 | Application of inner ester compound of jingdao in preparing medicine for treating inflammation-caused diseases |
| CN112402412B (en) * | 2020-11-18 | 2022-03-18 | 中国医学科学院药用植物研究所 | Application of inner ester compound of jingdao in preparing medicine for treating inflammation-caused diseases |
| CN113288893A (en) * | 2021-07-02 | 2021-08-24 | 中国科学院兰州化学物理研究所 | Application of sesquiterpene lactone compounds in preparation of medicines for treating renal anemia |
| CN113288893B (en) * | 2021-07-02 | 2023-05-05 | 中国科学院兰州化学物理研究所 | Application of sesquiterpene lactone compound in preparation of medicine for treating renal anemia |
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| CN103788037B (en) | 2015-06-03 |
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