CN101456896A - Puncturevine furostanol saponins compounds and preparation method thereof - Google Patents
Puncturevine furostanol saponins compounds and preparation method thereof Download PDFInfo
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- CN101456896A CN101456896A CNA200710188591XA CN200710188591A CN101456896A CN 101456896 A CN101456896 A CN 101456896A CN A200710188591X A CNA200710188591X A CN A200710188591XA CN 200710188591 A CN200710188591 A CN 200710188591A CN 101456896 A CN101456896 A CN 101456896A
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Abstract
The invention relates to the technical field of compound extraction, in particular to a puncturevine furostanol saponin compound and an extraction method thereof. The puncturevine furostanol saponin compound has the following structure: 3-O-{beta-D-xylopyranose radical-(1,3)-[beta-D- xylopyranose radical -(1,2)]-beta-D-pyran glucose radical -(1,4)-[alpha-L- pyran rhamnose radical-(1,2)]-beta-D-galactopyranose radical}-22-methoxy radical-26-O-{beta-D- pyran glucose radical }-puncturevine sapogenin. The preparation method comprises the following steps: coating silica gel vent with puncturevine furostanol total saponin, carrying out the elution through a lower layer eluent made of chloroform, methanol and water with different proportion, carrying out the collection step by step with each portion of 100ml, carrying out the thin layer inspection, merging puncturevine new glycoside monomeric compound solution, carrying out the decompression and concentration of the solution till the solution is dried, and carrying out recrystallization through methanol to obtain white needle-like crystal.
Description
Technical field:
The present invention relates to compound extractive technique field, be specifically related to a kind of puncturevine furostanol saponins compounds and extracting method thereof.
Background technology:
Puncture vine has another name called Fructus Atriplicis Sibiricae, Fructus Tribuli, hard puncture vine.Nature and flavor suffering, hardship, tepor, slightly poisonous, go into liver, lung channel, have diffusing wind, make eye bright, the effect of the therapeutic method to keep the adverse qi flowing downward, promoting circulation of blood, tonifying kidney and benefiting sperm.Chinese medicine puncture vine tradition medicinal part is its fruit, and its main component comprises compositions such as puncture vine steroidal saponin, flavones, polysaccharide and alkaloid.The total saponins that extracts in the puncture vine (content about about 40%) is mainly used in the treatment cardiovascular and cerebrovascular diseases clinically, as present Xinnaotong capsule for treating blood vessel of heart and brain or Xinnao Shutong sheet etc.Kind of steroidal saponin surplus having 10 in the puncturevine herb wherein mainly contains three kinds of steroidal saponins, and the furostanol saponin compounds occupies an important position in these three kinds of steroidal saponins, and it directly affects treatment cardiovascular and cerebrovascular diseases effect.
Summary of the invention:
The present invention will provide a kind of puncturevine furostanol saponins compounds and preparation method thereof.
Technical scheme provided by the present invention comprises: a kind of puncturevine furostanol saponins compounds, and its structural formula is:
A kind of preparation method of puncturevine furostanol saponins compounds comprises the steps:
Getting silicagel column on the puncturevine furostanol total saponins, is that elutriant carries out wash-out with chloroform-methyl alcohol-water different ratios lower floor, and substep is collected, every part of about 100ml, and the thin layer inspection merges monomeric compound solution, is evaporated to driedly, uses recrystallizing methanol, must white needle.
In the such scheme, last silicagel column behind the recrystallization.Further improve purity.
The present invention has prepared a kind of furostanol saponin compounds that can determine structural formula, lays a good foundation for continuing research.
Embodiment:
A kind of puncturevine furostanol saponins compounds, its structural formula is:
A kind of preparation method of puncturevine furostanol saponins compounds:
Get the puncturevine furostanol total saponins and go up silicagel column (70 * 1000mm) in right amount, with chloroform-methyl alcohol-water (65:35:10) lower floor is that elutriant carries out wash-out, substep is collected, every part of about 100ml, the thin layer inspection merges wherein 85 parts, be evaporated to dried, use recrystallizing methanol, last again silicagel column gets the about 400mg of white needle.
A kind of preparation method of puncturevine furostanol saponins compounds:
Get the puncturevine furostanol total saponins and go up silicagel column (70 * 1000mm) in right amount, with chloroform-methyl alcohol-water (60:35:15) lower floor is that elutriant carries out wash-out, substep is collected, every part of about 100ml, the thin layer inspection merges wherein 70 parts of the new glycosides solution of puncture vine, be evaporated to dried, use recrystallizing methanol, last again silicagel column gets the about 360mg of white needle.
The extracting method of the puncturevine furostanol total saponins that is adopted in the such scheme can be: get sandbur medicinal material 1kg, pulverize, first fries in shallow oil that to add pH value be 5.0 water, and amount of water is 8 times, carries out refluxing extraction each 2 hours, filters; Second fries in shallow oil that to add pH value be 6.0 water, and amount of water is 6 times, carries out refluxing extraction each 1 hour, filters; The 3rd fries in shallow oil that to add pH value be 8.0 water, and amount of water is 6 times, carries out refluxing extraction each 1 hour, filters, and filtrate merges.(0.085Mpa) being evaporated to relative density is 1.05 ~ 1.15, and it is 65% that adding ethanol makes pure content, leaves standstill 18 hours at 55 ℃ with merging filtrate, filter, (0.085Mpa) be evaporated to nothing alcohol flavor, concentrated solution low temperature (about 4 ℃) left standstill 24 hours filtrate, filtered at 50 ℃ again.Concentrated solution adds 3 times of water gaging dilution back D101 macroporous adsorptive resins by having handled well, extremely colourless with 20% ethanol elution earlier, use 60% ethanol elution again, collect 60% ethanol eluate, in 50 ℃ of concentrating under reduced pressure, the Fructus Tribuli total saponins 56g after the vacuum-drying (60 ℃).
Physico-chemical property: this product is a white, needle-shaped crystals, odorless, and bitter is soluble in methyl alcohol, the second alcohol and water, is slightly soluble in the acetoneand ethyl acetate, is dissolved in hardly in chloroform and the ether.217～219 ℃ of fusing points (decomposition).Through consulting this compound is the furostanol saponin compounds.
Purity is determined: all be single spot through 3 development system inspection knowledges on thin layer plate.The point sample amount is 10 times of suitable method of inspection point sample amount.Chromatogram does not show the impurity spot.
Structural confirmation:
(1) instrument: UV-2201 type ultraviolet-visible pectrophotometer
The UAVANCE-DRX-500 nuclear magnetic resonance analyser
The ESQUIRE-LC/MS mass spectrograph
The UNICAM-2010FTIR infrared spectrometer
(2) chemical process:
With above-mentioned white crystals o'clock on two silica gel G-CMC thin layer plate, put diosgenin and monose reference substance again, 60 ℃ of airtight hydrolysis are 60 minutes in hydrochloric acid vapour, take out, airing, a plate launches with chloroform-methyl alcohol (98:2), paradimethy laminobenzaldehyde colour developing with improvement, one punctation appears, and inconsistent with diosgenin, illustrate that sapogenin is not a diosgenin.Another plate launches with chloroform-methyl alcohol-water (30:12:4), phthalic acid-aniline chromogenic reagent, and the spot of sample sugar is consistent with rhamnosyl, glucose, wood sugar and semi-lactosi.Illustrate rhamnosyl, glucose, wood sugar and semi-lactosi are arranged in this compound.
(3) UV spectrum
The maximum absorption that UV spectrum provides the new glycosides of puncture vine is 192nm.
(4) ESI-MS spectrum
ESI-MS provides m/z:1383.5[M+K]
+, 1367[M+Na]
+, 1313.6[M-OCH
3], the 4493[aglycon]
+The molecular weight that draws this compound thus is 1344.The syncaryon magnetic resonance spectrum
1H,
13C and DEPT spectrum, the molecular formula of this compound is C
62H
104O
31
(5) IR spectrum
Infrared spectra provides 3641 (υ
OH), 2935,2863 (υ
CH), 1464,1392 (δ
CH), 1057 (υ
C-0) cm
-1Deng absorption peak.
(6) NMR spectrum
(7) Tang ownership and contact
By utilizing 1D and 2D gradient fields NMR technology, comprise 1D gradient fields selectivity TOCSY and GOESY, 2D gradient fields COSY, TOCSY, HSQC, HSQC-TOCSY and NOESY, determine that its sugar is respectively beta galactose, α-rhamnosyl, β-glucose and β wood sugar, catenation sequence β-D-xylopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranose base of sugar is connected with 3 of aglycons, and β-D-glucopyranosyl is connected to 26 of aglycons.
Analysis by above chemical process, spectroscopic data, reach with pertinent literature and compare, determine that this All new compounds is 3-O-{ β-D-xylopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranose base-22-methoxyl group-26-O-{ β-D-glucopyranosyl }-total saponins of tribulus unit.
Owing to have a saponin(e open loop structure, be inferred as the puncturevine furostanol saponins compounds according to the chemical structure of gained.It is applied to treat in the medication preparation of cardiovascular and cerebrovascular diseases, has determined curative effect, effective advantage.
Claims (3)
1, a kind of puncturevine furostanol saponins compounds, its structural formula is:
2, the preparation method of a kind of puncturevine furostanol saponins compounds as claimed in claim 1, it is characterized in that: comprise the steps, getting silicagel column on the puncture vine cottonrose hibiscus steroid total saponins, is that elutriant carries out wash-out with chloroform-methyl alcohol-water different ratios lower floor, and substep is collected, every part of about 100ml, thin layer is checked, merges the new glycosides monomeric compound of puncture vine solution, is evaporated to dried, use recrystallizing methanol, get white needle.
3, the preparation method of a kind of puncturevine furostanol saponins compounds as claimed in claim 2 is characterized in that: last silicagel column behind the recrystallization.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102590432A (en) * | 2009-07-20 | 2012-07-18 | 甘肃奇正藏药有限公司 | Detection method for medicine for curing cold nature yellow water disease |
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2007
- 2007-12-12 CN CN200710188591XA patent/CN101456896B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102590432A (en) * | 2009-07-20 | 2012-07-18 | 甘肃奇正藏药有限公司 | Detection method for medicine for curing cold nature yellow water disease |
| CN102590432B (en) * | 2009-07-20 | 2014-08-06 | 甘肃奇正藏药有限公司 | Detection method for medicine for curing cold nature yellow water disease |
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| CN101456896B (en) | 2012-02-01 |
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