CN1850847A - Method for preparing periplogenin - Google Patents
Method for preparing periplogenin Download PDFInfo
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- CN1850847A CN1850847A CN 200610013621 CN200610013621A CN1850847A CN 1850847 A CN1850847 A CN 1850847A CN 200610013621 CN200610013621 CN 200610013621 CN 200610013621 A CN200610013621 A CN 200610013621A CN 1850847 A CN1850847 A CN 1850847A
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- periplogenin
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- column chromatography
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Abstract
The invention discloses a manufacture method for periplocin that includes the following steps: taking acid hydrolysis to the raw material containing periplocin and collecting to gain intermediate A; taking column chromatography to the intermediate A and concentrating and drying to gain intermediate B; taking recrystallization and high efficient liquid phase gaining periplocin that has purity of 90%-100%. The invention has high yield, and has simple technology, low cost and could realize industrializing producing.
Description
Technical field
The present invention relates to technical field of traditional Chinese medicines, the preparation method of a kind of periplogenin of saying so more specifically.
Background technology
Chinese medicine Root-bark of Chinese Silkvine (having another name called periploca sepium, periploca spium skin) is the dry root skin of asclepiadaceae plant periploca spium (Periploca sepium), the traditional Chinese medical science thinks that it has the effect of wind-damp dispelling, strengthening the bones and muscles, is mainly used in arthralgia due to wind-cold-dampness pathogen BI syndrome, soreness of the waist and knees, shortness of breath and palpitation, edema of lower limbs etc.
Contain cardiac glycoside composition periplocoside (periplocin, C in the Root-bark of Chinese Silkvine
36H
56O
13), periplocoside also is present in the stem (xylem that comprises stem skin and stem) of periploca spium plant, and this composition also is present in the black keel (having another name called the Yunnan periploca spium, Periploca forrestii) of congener of periploca spium.
Periplocoside can change periplogenin (C under certain condition
30H
46O
8).
Periplogenin has cardiac stimulant and pharmacological action such as antitumor.According to Chinese Medical Journal [J] .1956, literary composition report such as 7:651 Li Zhang literary composition " cardiotonic of periploca spium skin (periploca sepium) ", periplogenin also has cardiotonic, and onset is rapid, and the property accumulated is little.According to herbal medicine [J] .2006, report in the red grade of 37 (4): 519 old books " the antitumor activity component research (I) of the Root-bark of Chinese Silkvine " literary composition: periplogenin has very strong restraining effect to the MCF-7 tumor cell proliferation.
About the preparation of periplogenin do not have at present sophisticated can industrialized production method.Hideji Itokawa etc. are at " Studies on Chemical Constituents of Antitumor Fraction from Periploca Sepium " (Chem.Pharm.Bull, 1987,35 (11): the method for the separation periplogenin of announcing 4524) is: with behind methanol extraction Root-bark of Chinese Silkvine → n-hexane extraction → water layer is with the silica gel column chromatography → C of chloroform extraction → repeatedly
18Reversed phase column chromatography → periplocoside → acid alcohol hydrolysis → silica gel column chromatography → periplogenin.This technology be obtain earlier the periplocoside monomer again hydrolysis obtain periplogenin, flow process is longer, silica gel column chromatography not only expends organic solvent repeatedly, and bigger to the dead adsorptive capacity of periplocoside; Have two glycan molecules in addition in the molecule of periplocoside, certain polarity is arranged, (Sun Wenji: natural medicinal ingredients extraction separation and preparation .1994 almost insoluble in chloroform, Beijing: Chinese Medicine science and technology press: 269), therefore this technology can only extract the periplocoside of the trace in the medicinal material, and it is higher to adopt this method to obtain the periplogenin cost.
Hu Yingjie is in " chemical ingredients of Yunnan periploca spium " (Yunnan plant research [J], 1989,11 (4): the separation method of periplogenin of report is to be raw material with Yunnan periploca spium medicinal material 465), through 95% extraction using alcohol → petroleum ether degreasing → acetone backflow → silica gel column chromatography → chloroform-methanol mixed solvent wash-out → periplogenin monomer, yield is 0.06%.The separation method that Chen Shuhong etc. adopt in " the antitumor activity component research (I) of Root-bark of Chinese Silkvine " is: behind 80% extraction using alcohol → petroleum ether extraction → water layer extracted with diethyl ether → water layer ethyl acetate extraction → silica gel column chromatography → chloroform-methanol mixed solvent wash-out → periplogenin monomer, yield is 3.6 * 10
-4%.More than two kinds of separation methods be directly to adopt organic solvent to extract the periplogenin that trace exists in the raw material basically, and raw material is hydrolyzed periplocoside is not become periplogenin, so yield is very low, causes the herb resource waste, technical process is longer, can't realize mass industrialized production.
Summary of the invention
The objective of the invention is to overcome the defective that prior art exists, the preparation method that a kind of periplogenin monomer productive rate height, processing method are simple, low-cost, can realize the periplogenin of large-scale industrial production is provided.
The preparation method of periplogenin of the present invention comprises the steps:
(1) raw material that contains periplocoside is carried out acid hydrolysis and collection, obtain intermediate A;
(2) intermediate A is carried out column chromatography, adopt eluent to carry out gradient elution or isocratic elution, merge the cut that contains periplogenin, obtain intermediate B behind the concentrate drying;
(3) intermediate B recrystallization or high performance liquid phase being prepared purity is 90%～100% periplogenin; The solvent of described recrystallization is C
1-3Lower aliphatic alcohols a kind of, particular methanol or ethanol.
The raw material that contains periplocoside of the present invention can be that the stem (xylem that comprises stem skin and stem) of Cortex Periplocae Radicis extract, Root-bark of Chinese Silkvine medicinal material, Yunnan periploca spium medicinal material (being the black keel of congener of periploca spium, Periploca forrestii), periploca spium or other contain the Chinese medicinal materials of periplocoside.
The used acid of acid hydrolysis of the present invention is mineral acid or organic acid for example hydrochloric acid, sulfuric acid, acetic acid, formic acid or the like; Hydrolysis temperature is 10～100 ℃, and hydrolysis time is 0.1～48 hour, and the pH value of hydrolysis is controlled at 1～6.
Acid hydrolysis of the present invention and collection can be finished or finish in two steps in a step.
One step of acid hydrolysis and collection finishes and is: adopt the mixing solutions of organic solvent and sour water that the raw material that contains periplocoside is carried out acid hydrolysis, separate organic layer, obtain intermediate A behind the concentrate drying; Two steps of acid hydrolysis and collection finish and are: (1) is adopted aqueous acid earlier or is contained the C of 5-95%
1-3The aqueous acid of lower aliphatic alcohols carries out acid hydrolysis, concentrates; If with containing C
L-3The aqueous acid of lower aliphatic alcohols carries out acid hydrolysis, should wave clean Fatty Alcohol(C12-C14 and C12-C18) when concentrated.(2) carry out 1 time or repeatedly extraction with the concentrated solution of organic solvent, obtain intermediate A after the extraction liquid reconcentration drying step (1).Wherein said organic solvent is a kind of of ethyl acetate, chloroform, toluene, ether, methylene dichloride; C commonly used
1-3Lower aliphatic alcohols comprises: methyl alcohol, ethanol, propyl alcohol, Virahol or the like, particular methanol, ethanol.
Column chromatography of the present invention comprises forward column chromatography, reversed phase column chromatography, and wherein forward column chromatography filler is 80 orders～400 purpose silica gel or aluminium sesquioxides; Oppositely the used filler of column chromatography is the C of 5 μ m or 10 μ m granularities
18Or C
8
The general position of the volume ratio of the used eluent of column chromatography is 10: 0～10 ethyl acetate, chloroform, methylene dichloride, benzene, toluene, ether, sherwood oil, normal hexane, tetrahydrofuran (THF), acetonitrile, acetone, methyl alcohol, ethanol, water two kinds.Preferred volume ratio is 10: 0～10 ethyl acetate, chloroform, ether, sherwood oil, acetone, methyl alcohol, ethanol, water two kinds.Sherwood oil-ethyl acetate mixture for example; Methyl alcohol-water mixed solution; Sherwood oil-chloroform mixing solutions; Sherwood oil-alcohol mixed solution or the like.
The present invention can adopt gradient elution, also can adopt isocratic elution, collects the cut that contains periplogenin, and concentrate drying obtains intermediate B.Intermediate B is carried out recrystallization, and to obtain purity be 90%～100% periplogenin; Described recrystallization solvent for use is a kind of of lower aliphatic alcohols such as methyl alcohol, ethanol.
Intermediate B of the present invention adopts the method for high performance liquid phase preparation as follows: C
18Or C
8The reversed-phase preparative chromatography post; Chromatographic condition: moving phase is methyl alcohol-water; Detect wavelength 218nm～220nm, the supervision elution curve is collected with guide product, obtains periplogenin and collects liquid; Collect the liquid concentrate drying, obtain the pure product of periplogenin.
With the periplogenin of the inventive method preparation through UV, IR, MS,
13C, NMR structure are identified and are confirmed as periplogenin.Spectroscopic data and Hideji Itokawa etc. are at document " Studies on Chemical Constituents of Antitumor Fractionfrom Periploca Sepium " (Chem.Pharm.Bull, 1987,35 (11): the spectroscopic identification data consistent of the periplogenin of announcing 4524).
(1) the λ max of the UV spectrum of UV spectrum sample is 218nm.The UV spectrogram is seen accompanying drawing 1.
(2) the infrared spectra sample mainly is absorbed as 3408,1777,1740,1628cm
-1The IR spectrogram of sample is seen accompanying drawing 2.
(3) molecular ion peak of mass spectrum sample is m/z 390 (M
+), base peak is m/z 373 (M
+-OH).Its mass spectrogram is seen accompanying drawing 3.
(4) nuclear magnetic resonance sample
1The H-NMR spectrogram is seen accompanying drawing 4,
13The C-NMR spectrogram is seen accompanying drawing 5.The ownership of each spectral line sees Table 1 and table 2 respectively in the nmr spectrum of sample.
Table 1
1H-NMR spectrum data and ownership
| The proton sequence number | Data in literature | Periplogenin | Proton number | Peak shape |
| 3 17 18 19 21 21 22 | 4.15 2.76 0.86 0.92 4.80 4.98 5.86 | 4.166 2.776 0.871 0.934 4.799 4.976 5.870 | 1 1 3 3 1 1 1 | br s q s s dd dd s |
Table 2
13C-NMR spectrum data and ownership
| The carbon sequence number | Data in literature | Periplogenin | The carbon sequence number | Data in literature | Periplogenin |
| 1 2 3 4 5 6 | 24.85 27.85 67.91 36.86 74.67 35.15 | 24.81 26.81 67.97 35.18 74.64 36.85 | 13 14 15 16 17 18 | 49.50 85.32 32.94 26.82 50.61 15.70 | 49.47 85.41 32.98 27.89 50.67 15.70 |
| 7 8 9 10 11 12 | 23.69 40.74 38.98 40.66 21.49 39.99 | 23.71 40.66 38.98 40.78 21.49 39.99 | 19 20 21 22 23 | 16.69 174.31 73.53 117.38 174.63 | 16.69 174.56 73.47 117.68 174.54 |
The present invention prepares the method for periplogenin, is with the key distinction of prior art: (1) the present invention adopts organic solvent to carry out extracting and enriching and column chromatography after earlier the periplocoside in the raw material being hydrolyzed to periplogenin again, so yield obviously improves.For example the yield that the Root-bark of Chinese Silkvine medicinal material adopts organic solvent to extract in the prior art only is 3.6 * 10
-4%, and technical process is long, is difficult to realize suitability for industrialized production, and the monomeric yield of gained periplogenin can be up to 0.21～1.7% after adopting technical scheme of the present invention.
(2) technology of the present invention is simple, has adopted isolating again method after the acid hydrolysis, has simplified technology, has reduced consumption of organic solvent, thereby cost is reduced greatly, can realize suitability for industrialized production; Prepared periplogenin purity after recrystallization or HPLC preparation can reach 90%～100%.
Description of drawings
Fig. 1 is the UV figure of prepared periplogenin.
Fig. 2 is the IR figure of prepared periplogenin.
Fig. 3 is the MS figure of prepared periplogenin.
Fig. 4 is prepared periplogenin
1H-NMR figure.
Fig. 5 is prepared periplogenin
13C-NMR figure.
Embodiment
The present invention is described further below in conjunction with specific embodiment.Wherein prepared periplogenin crystalline UV, IR, MS,
1H-NMR,
13C-NMR figure sees Figure of description for details.
Periplocoside is soluble in methyl alcohol and ethanol, is slightly soluble in water, so no matter be all to contain periplocoside in the extract with water, alcohol or the preparation of pure water blended solvent.Adopt the Cortex Periplocae Radicis extract of patented technology (number of patent application: 200410019975.5: Root-bark of Chinese Silkvine cardiotonic effective extract, Preparation method and use) preparation, because used macroporous resin purification, so in the extract enrichment periplocoside, make the content of periplocoside higher.Below all can be used as the raw material of preparation periplogenin.Because periplocoside content is lower in the Root-bark of Chinese Silkvine medicinal material, and higher in the Cortex Periplocae Radicis extract, so the productive rate of periplogenin is higher when being raw material with the extract.
The preparation method of periplogenin, its processing step is:
(1) getting Cortex Periplocae Radicis extract 100 gram, is that 3 aqueous hydrochloric acid and isopyknic chloroform mixing solutions carry out acid hydrolysis with pH, and the time is 1 hour, and temperature is 80 ℃.
(2) hydrolysis finishes and tells chloroform layer, and concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is a silica gel, adopts gradient elution, and eluent is ethyl acetate-methanol mixed solution of 10: 0～10; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying;
(4) intermediate B is carried out recrystallization with ethanol, obtain periplogenin crystallization 1.7 grams, yield is 1.7%.
The preparation method of periplogenin, its processing step is:
(1) getting Cortex Periplocae Radicis extract 100 gram, is that 1 aqueous hydrochloric acid carries out acid hydrolysis with pH, and the time is 0.1 hour, and temperature is 100 ℃.
(2) extract 3 times with the acid hydrolysis liquid of ethyl acetate to (1), the extraction liquid concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is an aluminium sesquioxide, adopts gradient elution, and eluent is ethyl acetate-alcohol mixed solution of 10: 0～10; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying;
(4) intermediate B is carried out recrystallization with ethanol, obtain periplogenin crystallization 1.5 grams, yield is 1.5%.
Embodiment 3
The preparation method of periplogenin, its processing step is:
(1) getting 1 kilogram of Root-bark of Chinese Silkvine medicinal material, is that 6 aqueous sulfuric acid carries out acid hydrolysis with pH, and the time is 48 hours, and temperature is 10 ℃.
(2) extract with the acid hydrolysis liquid of ether to (1), the extraction liquid concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is C
18, adopting isocratic elution, eluent is methyl alcohol-water mixed solution of 10: 5; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying;
(4) intermediate B is carried out the high performance liquid phase preparation: chromatographic column: Hypersil (5 μ m, 20 * 250mm), moving phase is methyl alcohol-water (70: 30), and flow velocity: 2.5mL/min obtains pure product 2.1 grams of periplogenin, and yield is 0.21%.
Embodiment 4
The preparation method of periplogenin, its processing step is:
(1) getting 1 kilogram of Yunnan periploca spium medicinal material, is that 2 aqueous sulfuric acid and isopyknic ethyl acetate mixture carry out acid hydrolysis with pH, and the time is 6 hours, and temperature is 40 ℃.
(2) tell ethyl acetate layer, concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is C
8, adopting isocratic elution, eluent is ethanol-water mixed solution of 10: 6; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying;
(4) intermediate B is carried out the high performance liquid phase preparation: chromatographic column: Irregular C1
8(10 μ m, 20 * 200mm), moving phase is methyl alcohol-water (65: 35), and flow velocity: 3.0mL/min obtains pure product 3.2 grams of periplogenin, and yield is 0.32%.
The preparation method of periplogenin, its processing step is:
(1) getting Cortex Periplocae Radicis extract 100 gram, is that 2 aqueous acetic acid carries out acid hydrolysis with pH, and the time is 4 hours, and temperature is 50 ℃.
(2) extract with the acid hydrolysis liquid of chloroform to (1), the extraction liquid concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is a silica gel, adopts gradient elution, and eluent is sherwood oil-chloroform mixing solutions of 10: 0～10: 10; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying.
(4) intermediate B is carried out recrystallization with methyl alcohol, obtain periplogenin crystallization 1.35 grams, yield is 1.35%.
Embodiment 6
The preparation method of periplogenin, its processing step is:
(1) getting 1 kilogram on periploca spium stem, is that 4 aqueous formic acid carries out acid hydrolysis with pH, and 2 hours time, temperature is 70 ℃.
(2) extract with the acid hydrolysis liquid of ether to (1), the extraction liquid concentrate drying obtains intermediate A.
(3) intermediate A is carried out column chromatography, column packing is a silica gel, adopts isocratic elution, and eluent is sherwood oil-ethyl acetate mixture of 10: 5; Collection contains the cut of periplogenin, obtains intermediate B behind the concentrate drying.
(4) intermediate B is carried out recrystallization with methyl alcohol, obtain periplogenin crystallization 3.0 grams, yield is 0.3%.
Claims (7)
1, a kind of preparation method of periplogenin is characterized in that comprising the steps:
(1) raw material that contains periplocoside is carried out acid hydrolysis and collection, obtain intermediate A;
(2) intermediate A is carried out column chromatography, adopt eluent to carry out gradient elution or isocratic elution, merge the cut that contains periplogenin, obtain intermediate B behind the concentrate drying;
(3) intermediate B recrystallization or high performance liquid phase being prepared purity is 90%～100% periplogenin; The solvent of described recrystallization is C
1-3Lower aliphatic alcohols a kind of.
2, the preparation method of periplogenin according to claim 1, stem that the wherein said raw material that contains periplocoside can be Cortex Periplocae Radicis extract, Root-bark of Chinese Silkvine medicinal material, periploca spium and Yunnan periploca spium medicinal material or other contain the Chinese medicinal materials of periplocoside.
3, the preparation method of periplogenin according to claim 1, wherein said acid hydrolysis and collect and can finish in a step, or finish in two steps.
4, as the preparation method of periplogenin as described in the claim 3, wherein one of acid hydrolysis and collection step finished and is:
Adopt the mixing solutions of organic solvent and sour water that the raw material that contains periplocoside is carried out acid hydrolysis, separate organic layer, obtain intermediate A behind the concentrate drying;
Two steps finished and are: (1) is adopted aqueous acid earlier or is contained the C of 5-95%
1-3The aqueous acid of lower aliphatic alcohols carries out acid hydrolysis, concentrates; (2) carry out 1 time or repeatedly extraction with the concentrated solution of organic solvent, obtain intermediate A after the extraction liquid reconcentration drying step (1);
Wherein said organic solvent is a kind of of ethyl acetate, chloroform, toluene, ether, methylene dichloride; Hydrolysis temperature is 10～100 ℃, and hydrolysis time is 0.1～48 hour, and the pH value of hydrolysis is controlled at 1～6.
5, the preparation method of periplogenin according to claim 1, wherein said column chromatography comprises forward column chromatography, reversed phase column chromatography; The volume ratio of used eluent is 10: 0～10 ethyl acetate, chloroform, methylene dichloride, benzene, toluene, ether, sherwood oil, normal hexane, tetrahydrofuran (THF), acetonitrile, acetone, methyl alcohol, ethanol, water two kinds.
6, as the preparation method of periplogenin as described in the claim 5, wherein the volume ratio of used eluent is 10: 0～10 ethyl acetate, chloroform, ether, sherwood oil, acetone, methyl alcohol, ethanol, water two kinds.
7, as the preparation method of periplogenin as described in the claim 5, wherein forward column chromatography filler is silica gel or aluminium sesquioxide; Oppositely the used filler of column chromatography is C
18Or C
8
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|---|---|---|---|
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|---|---|---|---|
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| CN102352401A (en) * | 2011-07-26 | 2012-02-15 | 苏州宝泽堂医药科技有限公司 | Method for preparing periplogenin through enzymatic hydrolysis |
| CN105343110A (en) * | 2015-11-19 | 2016-02-24 | 东北师范大学 | Applications of periplogenin, and periplogenin derivative in preventing and treating skin proliferation diseases |
| CN106868087A (en) * | 2017-03-28 | 2017-06-20 | 浙江树人学院 | A kind of Biotransfer process for preparing of periplogenin |
| CN107073134A (en) * | 2016-12-06 | 2017-08-18 | 江苏大学 | A kind of conjugate and its preparation method and purposes of active skull cap components cardenolides steroids and Octreotide |
| CN107735108A (en) * | 2016-12-06 | 2018-02-23 | 江苏大学 | A kind of PEGylation vitamin E periplocymarin conjugate nanoparticle and its preparation method and purposes |
| CN109100442A (en) * | 2018-09-26 | 2018-12-28 | 贵州医科大学 | The detection method of internal directly action component in Heiguteng exract medicinal material |
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2006
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102352401A (en) * | 2011-07-26 | 2012-02-15 | 苏州宝泽堂医药科技有限公司 | Method for preparing periplogenin through enzymatic hydrolysis |
| CN105343110A (en) * | 2015-11-19 | 2016-02-24 | 东北师范大学 | Applications of periplogenin, and periplogenin derivative in preventing and treating skin proliferation diseases |
| CN105343110B (en) * | 2015-11-19 | 2018-11-16 | 东北师范大学 | A kind of periplogenin and its derivative are used to prevent and treat the application of skin hyperplasia disease |
| CN107073134A (en) * | 2016-12-06 | 2017-08-18 | 江苏大学 | A kind of conjugate and its preparation method and purposes of active skull cap components cardenolides steroids and Octreotide |
| CN107735108A (en) * | 2016-12-06 | 2018-02-23 | 江苏大学 | A kind of PEGylation vitamin E periplocymarin conjugate nanoparticle and its preparation method and purposes |
| WO2018102974A1 (en) * | 2016-12-06 | 2018-06-14 | 江苏大学 | Conjugate for natural active ingredient cardiotonic steroid and octreotide, and preparation method therefor and uses thereof |
| WO2018102973A1 (en) * | 2016-12-06 | 2018-06-14 | 江苏大学 | Pegylated vitamin e periplocymarin conjugate nanoparticles and preparation method therefor |
| CN106868087A (en) * | 2017-03-28 | 2017-06-20 | 浙江树人学院 | A kind of Biotransfer process for preparing of periplogenin |
| CN109100442A (en) * | 2018-09-26 | 2018-12-28 | 贵州医科大学 | The detection method of internal directly action component in Heiguteng exract medicinal material |
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