CN107383141A - The method that the ketone of 24 ethyl cholestane of (20R) 22E, 4,22 diene 3 is extracted in Job's tears cauline leaf - Google Patents
The method that the ketone of 24 ethyl cholestane of (20R) 22E, 4,22 diene 3 is extracted in Job's tears cauline leaf Download PDFInfo
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- CN107383141A CN107383141A CN201710763248.7A CN201710763248A CN107383141A CN 107383141 A CN107383141 A CN 107383141A CN 201710763248 A CN201710763248 A CN 201710763248A CN 107383141 A CN107383141 A CN 107383141A
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- ketone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Abstract
The present invention discloses a kind of method that the ketone of 24 4,22 diene of ethyl cholestane of (20R) 22E 3 is extracted in Job's tears cauline leaf, comprises the following steps：Dry Job's tears cauline leaf is crushed, adds ethanol heating and refluxing extraction, extract solution is concentrated to give extractum A；After extractum A adds moisture to dissipate, with petroleum ether extraction, petroleum ether partial concentration obtains medicinal extract B；Medicinal extract B first passes through silica gel column chromatography, using petroleum ether ethyl acetate gradient, collects containing the composition isolated and purified, then chromatographs, and is eluted using absolute dichloromethane, and what is obtained isolates and purifies containing the composition isolated and purified through preparative high performance liquid chromatography, collects tR=31 min component, concentrate, crystallization, produce.The present invention extracts the ethyl cholestane 4 of (20R) 22E 24 from discarded Job's tears cauline leaf, the ketone of 22 diene 3, reduce environmental pollution, improve the utilization rate of Job's tears cauline leaf, extend the industrial chain of Job's tears, the income of Job's tears industry is added, there are preferable economic benefit and ecological benefits.
Description
Technical field
The invention belongs to chemical field, and in particular to extracted in a kind of Job's tears cauline leaf (20R) -22E-24- ethyls cholestane -
The method of 4,22- diene -3- ketone.
Background technology
Job's tears (Coix lachryma-jobi L.) is grass family (Gramineae) Coix, slightly sweet flavor, cold nature,
The effect of with invigorating the spleen, tonifying lung, heat-clearing, dampness removing, it is known as the good reputation of " king of tonic ".Job's tears whole body is precious, and Job's tears stem can
Prevent and treat measles, eczema etc.；Contained alkaloid in jobstears leaf, there are clearing heat and promoting diuresis, invigorating the spleen desinsection, warm stomach QI invigorating, disk promoting blood circulation etc. of relaxing
Effect.The medicinal parts such as the root of Job's tears, cauline leaf, benevolence have a large amount of uses in 15 nationalitys such as Zhuang, the Mongols, Tibetan.
In recent years, domestic and foreign scholars are studied the chemical composition and pharmacological activity of Job's tears, contained main pharmacological in coix seed
Active component is aliphatic acid, fat, sterols, triterpenes, polysaccharide compound and protein, amino acid and vitamin etc., right
There is excitation in isolated heart, intestinal tube, uterus, have antitumor, immunological regulation, antiviral, decompression, hypoglycemic, anti-inflammatory and antalgic
And suppress many pharmacological activity such as trypsase.
Research to Job's tears at present essentially consists in coix seed as health care of food material plant and develops and study, Job's tears cauline leaf
Study less.Job's tears cauline leaf is not fully utilized, and is dropped mostly as discarded object, causes the very big wave of resource
Take.Effective, valuable composition how is extracted from Job's tears cauline leaf, improves the utilization rate of Job's tears, is one and is badly in need of asking for solution
Topic.
The content of the invention
In order to solve the above problems, the present invention provide extracted in a kind of Job's tears cauline leaf (20R) -22E-24- ethyls cholestane -
The method of 4,22- diene -3- ketone.
The present invention is achieved through the following technical solutions：
A kind of method that (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf, including with
Lower step：
(1) alcohol extracting：Dry Job's tears cauline leaf is crushed, adds 90% ethanol, 60-70 DEG C is heated to, refluxing extraction, extracts
Liquid is concentrated under reduced pressure to obtain extractum A；
(2) extract：Moisture is added to dissipate the extractum A of step (1), with petroleum ether extraction, petroleum ether portion is concentrated to give
Medicinal extract B；
(3) primary column chromatography：By the medicinal extract B of step (2) 200-300 mesh silica gel column chromatographies, petroleum ether-ethyl acetate is used
Gradient elution, eluent is made into TLC detections, collects washing containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
De- point；
(4) secondary column chromatography：By step (3) washing containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
De- point use 200-300 mesh silica gel column chromatographies, and eluant, eluent is absolute dichloromethane, and eluent is made into TLC detections, collect contain (20R)-
The elution of 22E-24- ethyl cholestane -4,22- diene -3- ketone point；
(5) the efficient liquid chromatography of preparative isolates and purifies：Step (4) is contained into (20R) -22E-24- ethyls cholestane -4,
The elution lease making preparative high performance liquid chromatography of 22- diene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase
For pure methanol, Detection wavelength 210nm, detector ELSD, t is collectedR=31min component；
(6) crystallize：By tR=31min component concentration, with methanol-water crystallization, obtains (20R) -22E-24- ethyl cholesterics
Alkane -4,22- diene -3- ketone.
As the further explanation of the present invention, the number of step (1) described heating and refluxing extraction is 3-5 times, each 1.5-
2.5h, 90% ethanol consumption are 8-12 times of Job's tears cauline leaf weight.
As the further explanation of the present invention, the number of step (2) described extraction is 3-5 times, and the dosage of petroleum ether is leaching
8-12 times of cream A weight.
As the further explanation of the present invention, the volume ratio of step (3) described petroleum ether-ethyl acetate is 15: 1~5: 1.
As the further explanation of the present invention, the flow velocity of step (5) described mobile phase is 140mLmin-1。
As the further explanation of the present invention, the volume ratio of step (6) described methanol-water is 100: 1.
Compared with prior art, beneficial effects of the present invention are：
1st, the present invention extracts (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone from discarded Job's tears cauline leaf,
Reduce environmental pollution, improve the utilization rate of Job's tears cauline leaf, extend the industrial chain of Job's tears, add the receipts of Job's tears industry
Enter, there are preferable economic benefit and ecological benefits.
2nd, extractum A of the present invention passes through petroleum ether extraction, can remove non polar impurities, the ingredients of a mixture is obtained letter
Change, difficulty is reduced for follow-up mask work, and silicagel column and chromatogram can be protected not to be contaminated, extend the use of chromatographic column
Life-span.
3rd, by the present invention in that being separated with the silica gel column chromatography of different mobile phases, most of impurity can be removed, is follow-up
Purifying reduces difficulty.
4th, the present invention uses preparative liquid chromatography, and by research, obtains in tR=31min isolated (20R)-
22E-24- ethyl cholestane -4,22- diene -3- ketone, this method preparation amount is big, and efficiency high, process cycle is short, acquisition
(20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone purity is high.
5th, method of the invention is simple to operate, efficiency high, obtained (20R) -22E-24- ethyls cholestane -4,22- bis-
Alkene -3- ketone high purity more than 98%.
Brief description of the drawings
Fig. 1 is the proton nmr spectra of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 2 is the carbon-13 nmr spectra of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 3 is the heteronuclear list quantum relation figure of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 4 is the Two-dimensional spectrum of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 5 is the ultraviolet spectrogram of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 6 is the positive ion source mass spectrum of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone；
Fig. 7 is the anion source mass spectrum of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in more detail, but is not limited to protection scope of the present invention.
Embodiment 1
A kind of method that (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf, including with
Lower step：
(1) alcohol extracting：Dry Job's tears cauline leaf is crushed, 90% ethanol of 8 times of weight is added, is heated to 60 DEG C, backflow carries
Take 3 times, each 2.5h, merge extract solution, be concentrated under reduced pressure to obtain extractum A；
(2) extract：Add moisture to dissipate the extractum A of step (1), with the petroleum ether extraction 3 times of 8 times of weight, merge petroleum ether
Part is extracted, is concentrated to give medicinal extract B；
(3) primary column chromatography：It is 15: 1~5 with volume ratio by the medicinal extract B of step (2) 200-300 mesh silica gel column chromatographies
: 1 petroleum ether-ethyl acetate gradient elution, eluent is made into TLC detections, collection contains (20R) -22E-24- ethyl cholesterics
The elution of alkane -4,22- diene -3- ketone point；
(4) secondary column chromatography：Step (3) is contained into (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
Elution point use 200-300 mesh silica gel column chromatographies, eluant, eluent is absolute dichloromethane, eluent is made into TLC detections, collection contains
The elution of (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone point；
(5) the efficient liquid chromatography of preparative isolates and purifies：Step (4) is contained into (20R) -22E-24- ethyls cholestane -4,
The elution lease making preparative high performance liquid chromatography of 22- diene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase
For pure methanol, flow velocity 140mLmin-1, Detection wavelength 210nm, detector ELSD, collect tR=31min component；
(6) crystallize：By tR=31min component concentration, with volume ratio be 100: 1 methanol-water crystallization, obtain (20R)-
22E-24- ethyl cholestane -4,22- diene -3- ketone.
Embodiment 2
A kind of method that (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf, including with
Lower step：
(1) alcohol extracting：Dry Job's tears cauline leaf is crushed, 90% ethanol of 12 times of weight is added, is heated to 70 DEG C, backflow carries
Take 5 times, each 1.5h, merge extract solution, be concentrated under reduced pressure to obtain extractum A；
(2) extract：Add moisture to dissipate the extractum A of step (1), with the petroleum ether extraction 5 times of 12 times of weight, merge petroleum ether
Part is extracted, is concentrated to give medicinal extract B；
(3) primary column chromatography：It is 15: 1~5 with volume ratio by the medicinal extract B of step (2) 200-300 mesh silica gel column chromatographies
: 1 petroleum ether-ethyl acetate gradient elution, eluent is made into TLC detections, collection contains (20R) -22E-24- ethyl cholesterics
The elution of alkane -4,22- diene -3- ketone point；
(4) secondary column chromatography：By step (3) washing containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
De- point use 200-300 mesh silica gel column chromatographies, and eluant, eluent is absolute dichloromethane, and eluent is made into TLC detections, collect contain (20R)-
The elution of 22E-24- ethyl cholestane -4,22- diene -3- ketone point；
(5) the efficient liquid chromatography of preparative isolates and purifies：Step (4) is contained into (20R) -22E-24- ethyls cholestane -4,
The elution lease making preparative high performance liquid chromatography of 22- diene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase
For pure methanol, flow velocity 140mLmin-1, Detection wavelength 210nm, detector ELSD, collect tR=31min component；
(6) crystallize：By tR=31min component concentration, with volume ratio be 100: 1 methanol-water crystallization, obtain (20R)-
22E-24- ethyl cholestane -4,22- diene -3- ketone.
Embodiment 3
A kind of method that (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf, including with
Lower step：
(1) alcohol extracting：Dry Job's tears cauline leaf is crushed, adds 90% ethanol of 8-12 times of weight, is heated to 65 DEG C, backflow
Extraction 4 times, each 2h, merge extract solution, be concentrated under reduced pressure to obtain extractum A；
(2) extract：Add moisture to dissipate the extractum A of step (1), with the petroleum ether extraction 4 times of 10 times of weight, merge petroleum ether
Part is extracted, is concentrated to give medicinal extract B；
(3) primary column chromatography：It is 15: 1~5 with volume ratio by the medicinal extract B of step (2) 200-300 mesh silica gel column chromatographies
: 1 petroleum ether-ethyl acetate gradient elution, eluent is made into TLC detections, collection contains (20R) -22E-24- ethyl cholesterics
The elution of alkane -4,22- diene -3- ketone point；
(4) secondary column chromatography：By step (3) washing containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
De- point use 200-300 mesh silica gel column chromatographies, and eluant, eluent is absolute dichloromethane, and eluent is made into TLC detections, collect contain (20R)-
The elution of 22E-24- ethyl cholestane -4,22- diene -3- ketone point；
(5) the efficient liquid chromatography of preparative isolates and purifies：Step (4) is contained into (20R) -22E-24- ethyls cholestane -4,
The elution lease making preparative high performance liquid chromatography of 22- diene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase
For pure methanol, flow velocity 140mLmin-1, Detection wavelength 210nm, detector ELSD, collect tR=31min component；
(6) crystallize：By tR=31min component concentration, with volume ratio be 100: 1 methanol-water crystallization, obtain (20R)-
22E-24- ethyl cholestane -4,22- diene -3- ketone.
Embodiment 4
A kind of method that (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf, including with
Lower step：
(1) alcohol extracting：Dry Job's tears cauline leaf is crushed, 90% ethanol of 11 times of weight is added, is heated to 65 DEG C, backflow carries
Take 4 times, each 2h, merge extract solution, be concentrated under reduced pressure to obtain extractum A；
(2) extract：Add moisture to dissipate the extractum A of step (1), with the petroleum ether extraction 4 times of 11 times of weight, merge petroleum ether
Part is extracted, is concentrated to give medicinal extract B；
(3) primary column chromatography：It is 15: 1~5 with volume ratio by the medicinal extract B of step (2) 200-300 mesh silica gel column chromatographies
: 1 petroleum ether-ethyl acetate gradient elution, eluent is made into TLC detections, collection contains (20R) -22E-24- ethyl cholesterics
The elution of alkane -4,22- diene -3- ketone point；
(4) secondary column chromatography：By step (3) washing containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
De- point use 200-300 mesh silica gel column chromatographies, and eluant, eluent is absolute dichloromethane, and eluent is made into TLC detections, collect contain (20R)-
The elution of 22E-24- ethyl cholestane -4,22- diene -3- ketone point；
(5) the efficient liquid chromatography of preparative isolates and purifies：Step (4) is contained into (20R) -22E-24- ethyls cholestane -4,
The elution lease making preparative high performance liquid chromatography of 22- diene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase
For pure methanol, flow velocity 140mLmin-1, Detection wavelength 210nm, detector ELSD, collect tR=31min component；
(6) crystallize：By tR=31min component concentration, with volume ratio be 100: 1 methanol-water crystallization, obtain (20R)-
22E-24- ethyl cholestane -4,22- diene -3- ketone.
To Fig. 1-Fig. 7's1H-NMR、13C-NMR, HSQC, COSY, UV, MS etc. are analyzed, specific as follows：
Note：* chemical shift is interchangeable, and * * chemical shifts are interchangeable, and ol represents signal overlap (signal
overlapping)。
By ES-TOF MS+:m/z 411.36[M+H]+,433.34[M+Na]+,449.32[M+K]+,843.71[2M+
Na]+,1254.08[3M+Na]+,ES-TOF MS─:M/z 409.35 [M-H]-and the molecular weight for speculating the compound is 410.
By1δ in H-NMR (600MHz, CDCl3)H5.15, dd, J=15.2,8.7Hz；5.02, dd, J=15.1,8.8Hz
Signal, which speculates, one group of typical double bond hydrogen signal, and is trans double bond, separately there is δH5.72, s independent double bond hydrogen signal.
With reference to13C-NMR (150MHz, CDCl3)) and 135 ° of DEPT, thus it is speculated that the compound shares 29 carbon atom signals,
Wherein 6 methyl (CH3), 9 methylene (CH2), 10 methines (CH), 4 quaternary carbons (C) speculate there are 29 carbon atoms, 46
Individual hydrogen atom, and δC200.8 be carbonyl carbon signals, thus it is speculated that has an oxygen atom, in summary speculates that molecular formula is C29H46O, push away
Survey as triterpene or steroidal compounds.It is 7 to calculate degree of unsaturation, removes two double bonds and the degree of unsaturation of a carbonyl, also 4
Degree of unsaturation, thus it is speculated that have 4 rings.δC123.7,171.7,138.1,129.4 it is double bond signal.
Hydrocarbon signal is corresponded by HSQC two-dimensional nucleus magnetic spectrum, with reference to δ in COSY two-dimensional nucleus magnetic spectrumsH5.15 with δH
5.02 δH5.15 with δH2.04 δH2.04 with δH1.01 δH5.02 with δH1.53 δH1.53 with δH0.84, δH 1.53
With 0.79, δH1.58 with δHThe functional group of 0.72 supposition presence (1- methyl -4- ethyl -5- methyl -2- alkene)-hexyl, i.e., 10
Carbon atom, remaining carbon atom speculate the tetracyclic triterpene ketone or Fourth Ring ketosteroid compouds being made up of 19 carbon, pass through comparison
Document Rizvi, Syed Q.A.Williams, John R.Synthesis and carbon-13nuclear magnetic
resonance studies ofΔ5saturated 4,4-disubstituted 3-
Ketosteroids.J.Org.Chem.1981, the data of similar structure in 46,1127-32., it is 4- alkene -3- steroids to determine parent nucleus
Ketone, and δ in COSY two-dimensional nucleus magnetic spectrumsH1.19 with δH2.04 determine the connection of (1- methyl -4- ethyl -5- methyl -2- alkene)-hexyl
At 17 of 4- alkene -3- sterones, then by comparing document Xiao-Ling Wang, Anne-Emmanuelle Hay, et
al.Kurt.Structure elucidation and NMR assignments of two new triterpenoids
from the stems of Paragonia pyramidata(Bignoniaceae)[J].Magn.Reson.Chem.2011,
49:184-189.
Middle identical structure determination compound is (20R) -22E-24-ethylcholesta-4,22-dien-3-one, name
Referred to as (20R) -22E-24- ethyls cholestane -4,22- diene -3- ketone.Its chemical structural formula is：
Claims (6)
1. extracting the method for (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone in a kind of Job's tears cauline leaf, its feature exists
In comprising the following steps：
（1）Alcohol extracting：Dry Job's tears cauline leaf is crushed, 90% ethanol is added, is heated to 60-70 DEG C, refluxing extraction, extract solution subtracts
Pressure is concentrated to give extractum A；
（2）Extraction：By step（1）Extractum A add moisture to dissipate, with petroleum ether extraction, petroleum ether portion is concentrated to give medicinal extract
B；
（3）Primary column chromatography：By step（2）Medicinal extract B 200-300 mesh silica gel column chromatographies, with petroleum ether-ethyl acetate gradient
Elution, eluent is made into TLC detections, collects the elution containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone
Point；
（4）Secondary column chromatography：By step（3）Elution containing (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone point
With 200-300 mesh silica gel column chromatographies, eluant, eluent is absolute dichloromethane, eluent is made into TLC detections, collection contains (20R) -22E-
The elution of 24- ethyl cholestane -4,22- diene -3- ketone point；
（5）The efficient liquid chromatography of preparative isolates and purifies：By step（4）Contain (20R) -22E-24- ethyl cholestane -4,22- two
The elution lease making preparative high performance liquid chromatography of alkene -3- ketone isolates and purifies, chromatographic column C18Post, diameter 8cm, mobile phase are pure first
Alcohol, Detection wavelength are 210 nm, detector ELSD, collect tR=31 min component；
（6）Crystallization：By tR=31 min component concentration, with methanol-water crystallization, obtains (20R) -22E-24- ethyls cholestane -4,
22- diene -3- ketone.
2. (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf according to claim 1
Method, it is characterised in that step（1）The number of the heating and refluxing extraction is 3-5 times, each 1.5-2.5h, 90% ethanol consumption
For 8-12 times of Job's tears cauline leaf weight.
3. (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf according to claim 1
Method, it is characterised in that step（2）The number of the extraction is 3-5 times, and the dosage of petroleum ether is 8-12 times of extractum A weight.
4. (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf according to claim 1
Method, it is characterised in that step（3）The volume ratio of the petroleum ether-ethyl acetate is 15: 1~5: 1.
5. (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf according to claim 1
Method, it is characterised in that step（5）The flow velocity of the mobile phase is 140 mLmin-1。
6. (20R) -22E-24- ethyl cholestane -4,22- diene -3- ketone is extracted in Job's tears cauline leaf according to claim 1
Method, it is characterised in that step（6）The volume ratio of the methanol-water is 100: 1.
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| CN201710763248.7A CN107383141A (en) | 2017-08-30 | 2017-08-30 | The method that the ketone of 24 ethyl cholestane of (20R) 22E, 4,22 diene 3 is extracted in Job's tears cauline leaf |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111491524A (en) * | 2017-12-19 | 2020-08-04 | 森永乳业株式会社 | Preparation method of Aloe powder |
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| CN106380501A (en) * | 2016-08-09 | 2017-02-08 | 右江民族医学院 | Method for extracting stigmasterol from coix stems |
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2017
- 2017-08-30 CN CN201710763248.7A patent/CN107383141A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106380501A (en) * | 2016-08-09 | 2017-02-08 | 右江民族医学院 | Method for extracting stigmasterol from coix stems |
Non-Patent Citations (3)
| Title |
|---|
| NARUMI, YASUHISA: "《Identification of sterols and steroidal 3-ones in the seeds of Echinochloa》", 《NIHON YUKAGAKKAISHI》 * |
| TAKATSUTO.S: "《Occurrence of Potential Brassinosteroid Precursor Steroids in Seeds of Wheat and Foxtail Millet》", 《JOURNAL OF PLANT RESEARCH 》 * |
| 郭力，康文艺主编: "《中药化学》", 31 August 2015, 中国医药科技出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111491524A (en) * | 2017-12-19 | 2020-08-04 | 森永乳业株式会社 | Preparation method of Aloe powder |
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Application publication date: 20171124 |