CN101633678A - Shaanxi euonymus glycoside I extracted from Shaanxi euonymus and extraction technique thereof - Google Patents
Shaanxi euonymus glycoside I extracted from Shaanxi euonymus and extraction technique thereof Download PDFInfo
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- CN101633678A CN101633678A CN 200910065906 CN200910065906A CN101633678A CN 101633678 A CN101633678 A CN 101633678A CN 200910065906 CN200910065906 CN 200910065906 CN 200910065906 A CN200910065906 A CN 200910065906A CN 101633678 A CN101633678 A CN 101633678A
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Abstract
The invention relates to a Shaanxi euonymus glycoside I extracted from Shaanxi euonymus and an extraction technique thereof. The technique comprises: stems and leaves of fresh Shaanxi euonymus are taken and then processed by histiocyte cataclase in acetone water solution at the room temperature; solvent is extracted, decompressed and recovered to obtain dry powder which is dissolved and centrifugated when being added with water; supernate passes through macroporous absorption resin column and then washed by water and 10% of methyl alcohol until eluent is colorless; after that, 10% of methyl alcohol eluent can be obtained, and solvent is decompressed at the low temperature and recovered to obtain dry powder which is then dissolved in gel column and eluted by water, so that eluent can be obtained; then, the obtained eluent is dripped onto a thin layer plate to be spread, and sprayed by anisaldehyde-concentrated sulfuric acid color development reagent, so as to show blue at first and then be changed into red fluid; the fluid sequentially passes through MCI Gel CHP-20 column, toyopearl HW-40 column, hydroxypropyl sephadex LH-20 column and silicagel column, so that colorless oily matter which is the Shaanxi euonymus glycoside I can be obtained. The Shaanxi euonymus glycoside I is a new compound, and the preparation method of the compound is convenient in operation, strong in reliability and great in economic and social benefits.
Description
One, technical field
The present invention relates to Shaanxi galactitol glycosides I and the extraction process thereof from the winged euonymus of Shaanxi, extracted.
Two, background technology
Shaanxi winged euonymus (Euonymus schensianus Maxi m.) is Celastraceae (Celastraceae) Euonymus (Euonymus) plant, has another name called spun gold and hangs butterfly, golden butterfly.According to " Xinhua's book on Chinese herbal medicine outline " record, this section plant has insecticidal activity more, mainly concentrates on Thunder God Calamus, Euonymus, Celastrus.Since the eighties in 20th century, Chinese scholar has been carried out extensive studies to the insecticidal activity of the many plants of Celastraceae, finds that wherein the Shaanxi winged euonymus has food refusal and anesthetic action to insect larvae.Be distributed widely in south, China North China, each province, Central China mainly is distributed in Funiu Shan Mountain district, Henan Province.Why does the Shaanxi winged euonymus have insecticidal activity? how its effective constituent is extracted is not seen that so far open report is arranged.
Three, summary of the invention
At above-mentioned situation, for overcoming the deficiency of prior art, the present invention's purpose is exactly by the Shaanxi winged euonymus being carried out the chemical constitution study of system, from Shaanxi winged euonymus leaf, stem, separate and identify a kind of new compound, thereby provide a kind of Shaanxi galactitol glycosides I and extraction process of from the winged euonymus of Shaanxi, extracting thereof, can effectively solve the problem of from the winged euonymus of Shaanxi, extracting activeconstituents Shaanxi galactitol glycosides I, the technical scheme of its solution is, the Shaanxi galactitol glycosides I that the present invention is alleged, colorless oil; Specific rotatory power is [α]
D 20-14.5 (c0.23, MeOH); Be soluble in acetone, methyl alcohol.Aubepine-vitriol oil spraying post-heating shows blue earlier, then becomes redness (105 ℃).HR-TOF-MS m/z:439.2307[M+Na]
+(calculated value: 439.2308), molecular formula: C
21H
36O
8, its structural formula is:
The extraction process of Shaanxi galactitol glycosides I of the present invention is: get fresh Shaanxi winged euonymus stem, leaf, in 70% aqueous acetone solution, extract twice under room temperature 15-25 ℃ with flash extracter (extraction equipment commonly used) historrhexis, each 15-20 minute, extracting solution merges 45 ℃ of decompression and solvent recoveries of back low temperature, get dry powder, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorptive resins Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries of low temperature get dry powder, with dry powder with gel Toyopearl HW-40 post on the water dissolution, the water wash-out, get elutriant, the elutriant point is dropped in thin layer plate (thin layer plate is known common agents plate) go up expansion, launch back with aubepine-vitriol oil developer spraying (aubepine-vitriol oil developer is known developer commonly used), show blue down earlier at 105 ℃, after the look RF value (the spot dot center of component is to the distance and the ratio of solvent front to the initial point distance of initial point) that reddens be stream part of 0.4, collect this stream part and obtain component A, component A is successively by MCI Gel CHP-20 post, Toyopearl HW-40 post, hydroxypropyl dextrane gel SephadexLH-20 post, silicagel column get colourless oily mater Shaanxi galactitol glycosides I.
The present invention is a kind of new compound, its preparation method advanced person, science, easy to operate, Shaanxi winged euonymus sample to Shaanxi, Henan, Shandong and other places carries out the repeated multiple times preparation as stated above, all obtained identical or akin result, shown good reliability of the present invention, efficiently solved and from the winged euonymus of Shaanxi, extract activeconstituents Shaanxi galactitol glycosides I, for the application of Shaanxi winged euonymus provides favourable technique means and pharmaceutical use, economic and social benefit is huge.
Four, description of drawings
Fig. 1 is the structural formula of Shaanxi galactitol glycosides I.
Fig. 2 is compound Shaanxi galactitol glycosides I's
1The H-NMR spectrum.
Fig. 3 is compound Shaanxi galactitol glycosides I's
13The C-NMR spectrum.
Fig. 4 is the hsqc spectrum of compound Shaanxi galactitol glycosides I.
Fig. 5 is the HMBC spectrum of compound Shaanxi galactitol glycosides I.
Fig. 6 is the IR spectrum of compound Shaanxi galactitol glycosides I.
Fig. 7 is the HR-TOF-MS spectrum of compound Shaanxi galactitol glycosides I.
Fig. 8 is the UV spectrum of compound Shaanxi galactitol glycosides I.
Five, embodiment
Below in conjunction with embodiment the specific embodiment of the present invention is elaborated.
In implementing and testing, used instrument of the present invention and material: column chromatography filler Diaion HP-20, MCIGel CHP-20 produce for Mitsubishi chemical company, Toyopearl HW-40 is that Japanese TOSOH company produces, Sephadex LH-20 is that Parmacia Biotech company produces, column chromatography used silica gel H produces (160-200 order) by Haiyang Chemical Plant, Qingdao, tlc silica gel is that Haiyang Chemical Plant, Qingdao produces (granulometric range 10-40 μ m), with 0.5%CMC-Na making sheet, dry in the shade 105 ℃ of activation 0.5h.
Nucleus magnetic resonance DPX-400 (400MHz for
1H-NMR and 100MHz for
13C-NMR) nmr determination, TMS are interior mark, by Institute of Analysis of Zhengzhou University for survey.The infrared spectrophotometer model is Shimadzu FTIR-8201, and for survey, used mass spectrograph is an APEX II type to mass spectrum by Institute of Analysis of Zhengzhou University.Fusing point is measured with the Kofler micro melting point apparatus, and is not calibrated.N-1000 type Rotary Evaporators (Shanghai Ai Lang Instr Ltd.), SHB-B95A type circulation ability of swimming is used vacuum pump (Zhengzhou Greatwall Scientific Industrial ﹠ Trading Co., Ltd.) more, DFZ-3 type vacuum drying oven (the medical thermostatic equipment in Shanghai factory).
Get Henan and produce fresh Shaanxi winged euonymus stem, leaf 10kg, in 70% aqueous acetone solution, extract twice under 18 ℃ of the room temperatures with flash extracter historrhexis, the 1st time 20 minutes, the 2nd time 15 minutes, extracting solution merged back 45 ℃ of decompression and solvent recoveries, got dry powder 410g, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorptive resins Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries get dry powder 15g, with dry powder with gel Toyopearl HW-40 post on the water dissolution, the water wash-out gets elutriant, the elutriant point is dropped on the thin layer plate launch, launching the back sprays with aubepine-vitriol oil developer, show down earlier blue at 105 ℃, after the redden RF value of look be stream part of 0.4, collect this stream and part obtain component A, component A is successively by MCI Gel CHP-20 post, Toyopearl HW-40 post, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column gets 26mg Shaanxi galactitol glycosides I.
Get Shaanxi and produce fresh Shaanxi winged euonymus stem, leaf 15kg, in 70% aqueous acetone solution, extract twice under 20 ℃ of the room temperatures with flash extracter historrhexis, each each 18 minutes, extracting solution merges back 45 ℃ of decompression and solvent recoveries, get dry powder 605g, dry powder adds the water-dispersion dissolving, and is centrifugal, macroporous adsorptive resins DiaionHP-20 on the supernatant liquor, water washes to elutriant colourless, uses 10% washed with methanol colourless to elutriant then, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries, dry powder 23g, with dry powder with gel Toyopearl HW-40 post on the water dissolution, water wash-out, get elutriant, the elutriant point dropped on the thin layer plate launch, launch the back, show blue down earlier at 105 ℃ with aubepine-vitriol oil developer spraying, after the redden RF value of look be stream part of 0.4, collect this stream part and obtain component A, component A passes through MCI Gel CHP-20 post, Toyopearl HW-40 post successively, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column obtains 39.5mg Shaanxi galactitol glycosides I.
Get Shandong and produce fresh Shaanxi winged euonymus stem, leaf 20kg, in 70% aqueous acetone solution, extract twice under 22 ℃ of the room temperatures with flash extracter historrhexis, 15 minutes for the first time, the 2nd time 20 minutes, extracting solution merged back 45 ℃ of decompression and solvent recoveries, got dry powder 825g, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorbent resin lives in Diaion HP-20 on the supernatant liquor, and water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries get dry powder 32g, with the water-soluble gel Toyopearl HW-40 post of going up of dry powder, the water wash-out gets elutriant, the elutriant point is dropped on the thin layer plate launch, launching the back sprays with aubepine-vitriol oil developer, show down earlier blue at 105 ℃, after the redden RF value of look be stream part of 0.4, collect this stream and part obtain component A, component A is successively by MCI Gel CHP-20 post, Toyopearl HW-40 post, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column obtains 51mg Shaanxi galactitol glycosides I.
The structure elucidation of Shaanxi galactitol glycosides I of the present invention: analyze after deliberation, and through experimental test, Shaanxi galactitol glycosides I, colorless oil; Specific rotatory power is [α]
D 20-14.5 (c0.23, MeOH); Be soluble in acetone, methyl alcohol.Aubepine-vitriol oil spraying post-heating shows blue earlier, then becomes redness (105 ℃).HR-TOF-MS m/z:439.2307[M+Na]
+(calculated value: 439.2308), molecular formula: C
21H
36O
8UV: λ
Max MeOHNm (log ε): 205.9nm; IR (KBr): υ
MaxCm
-1: 3366,2924,2862,1611,1588,1463,1375. with GJH-14's
1H-NMR spectrum is compared, except at δ
H4.58-3.08 between have more outside the signal of 7 hydrogen protons, its residue spectral peak is all quite similar, contrasts the two
13The C-NMR spectrum is at δ
C97.6-62.3 between have more 6 carbon signals, can release this compound thus is to be aglycon with GJH-14, has connected a glucose again.
1In the H-NMR spectrum, 5 hydrogen proton signals, wherein δ appear in low place
H5.96 (1H, dd, J=10.7,17.3Hz, H-2), 5.21 (1H, dd, J=1.9,17.3Hz, H-1t) and 4.96 (1H, dd, J=1.9,10.7Hz H-1c) is the ABX system of a vinyl, δ
H5.68 (1H, dt, J=15.5,6.4Hz, H-5) and δ
H5.51 (1H, d, J=15.5Hz, H-6) two protons on trans double bond of formation, its coupling constant is J=15.5Hz.δ
H3.88 (J=6.9Hz is a methine protons signal H-10), and is connected with oxy radical for 1H, t; δ
H2.20 (2H, t, J=6.4Hz, H-4), 1.86 (2H, m, H-8) and 1.84 (2H, m H-9) are 3 methylene signals; δ
H1.20 (3H, s, H-14), 1.27 (3H, s, H-15), 1.11 (3H, s, H-12) and 1.11 (3H, s H-13) are 4 methyl signals.Above signal and GJH-14's
1The H-NMR spectrum signal is identical substantially.In addition, δ
H4.58 (1H, d, J=7.8Hz, H-1 ') is end group hydrogen signal on the glucose, known by inference by its coupling constant to be beta comfiguration.
13Show 21 carbon signals in the C-NMR spectrum, remove 15 carbon signals on the aglycon, all the other 6 carbon signal (δ
C97.6,77.3,76.2,74.2,71.1,62.3) and should be the carbon signal on the glucose.In the HMBC spectrum, δ
H(4.58 1H, d, J=7.8Hz, H-1 ') and δ
C78.5 (C-11) and δ
C74.2 (C-2 ') has long-range relevant, illustrates that glucose is connected on 11.Therefore, the structure of determining GJH-17 for (3S, 7R, 10S)-3,11-dihydroxyl-7,10-epoxy-3,7,11-trimethylammonium 12 carbon-1,5-diene-11-O-β-D-glucoside.Do not appear in the newspapers through consulting document, be defined as a new compound, called after Shaanxi galactitol glycosides I.Simultaneously, this compound shows all that through various insects larvas such as rice borer, locust being carried out tens of tests larva is had food refusal and anesthetic action, has insecticidal activity.
Following table provides The compounds of this invention Shaanxi galactitol glycosides I's
1H-NMR (400MHz, Acetone-d
6) and
13C-NMR (100MHz, Acet one-d
6) data.
Annotate: this table has provided the hydrocarbon ownership of this compound, the exactness that certification structure is resolved.
Claims (5)
1, a kind of Shaanxi galactitol glycosides I, it is characterized in that: the molecular formula of said Shaanxi galactitol glycosides I is C
21H
36O
8, structural formula is:
2, the extraction process of the described Shaanxi of claim 1 galactitol glycosides I, it is characterized in that: get fresh Shaanxi winged euonymus stem, leaf, in 70% aqueous acetone solution, extract twice under room temperature 15-25 ℃ with flash extracter historrhexis, each 15-20 minute, extracting solution merges 45 ℃ of decompression and solvent recoveries of back low temperature, get dry powder, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorptive resins Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries of low temperature get dry powder, with dry powder with gel Toyopearl HW-40 post on the water dissolution, the water wash-out, get elutriant, the elutriant point dropped on the thin layer plate launch, launch the back, show blue down earlier at 105 ℃ with aubepine-vitriol oil developer spraying, after the look RF value that reddens be stream part of 0.4, collect this stream part and obtain component A, component A passes through MCI Gel CHP-20 post, Toyopearl HW-40 post successively, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column gets colourless oily mater Shaanxi galactitol glycosides I.
3, the extraction process of Shaanxi galactitol glycosides I according to claim 2, it is characterized in that, get Henan and produce fresh Shaanxi winged euonymus stem, leaf 10kg, in 70% aqueous acetone solution, extract twice under 18 ℃ of the room temperatures with flash extracter historrhexis, the 1st time 20 minutes, the 2nd time 15 minutes, extracting solution merges back 45 ℃ of decompression and solvent recoveries, get dry powder 410g, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorptive resins Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries get dry powder 15g, with dry powder with gel Toyopearl HW-40 post on the water dissolution, the water wash-out gets elutriant, the elutriant point is dropped on the thin layer plate launch, launching the back sprays with aubepine-vitriol oil developer, show down earlier blue at 105 ℃, after the redden RF value of look be stream part of 0.4, collect this stream and part obtain component A, component A is successively by MCI Gel CHP-20 post, Toyopearl HW-40 post, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column gets 26mg Shaanxi galactitol glycosides I.
4, the extraction process of Shaanxi galactitol glycosides I according to claim 2, it is characterized in that, get Shaanxi and produce fresh Shaanxi winged euonymus stem, leaf 15kg, in 70% aqueous acetone solution, extract twice under 20 ℃ of the room temperatures with flash extracter historrhexis, each each 18 minutes, extracting solution merges back 45 ℃ of decompression and solvent recoveries, get dry powder 605g, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorptive resins Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries, dry powder 23g, with dry powder with gel ToyopearlHW-40 post on the water dissolution, water wash-out, get elutriant, the elutriant point dropped on the thin layer plate launch, launch the back, show blue down earlier at 105 ℃ with aubepine-vitriol oil developer spraying, after the redden RF value of look be stream part of 0.4, collect this stream part and obtain component A, component A passes through MCI Gel CHP-20 post, Toyopearl HW-40 post successively, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column obtains 39.5mg Shaanxi galactitol glycosides I.
5, the extraction process of Shaanxi galactitol glycosides I according to claim 2, it is characterized in that, get Shandong and produce fresh Shaanxi winged euonymus stem, leaf 20kg, in 70% aqueous acetone solution, extract twice under 22 ℃ of the room temperatures with flash extracter historrhexis, 15 minutes for the first time, the 2nd time 20 minutes, extracting solution merges back 45 ℃ of decompression and solvent recoveries, get dry powder 825g, dry powder adds the water-dispersion dissolving, centrifugal, macroporous adsorbent resin lives in Diaion HP-20 on the supernatant liquor, water washes to elutriant colourless, use 10% washed with methanol colourless then to elutriant, 10% meoh eluate that obtains, 45 ℃ of decompression and solvent recoveries get dry powder 32g, with the water-soluble gel Toyopearl HW-40 post of going up of dry powder, the water wash-out gets elutriant, the elutriant point is dropped on the thin layer plate launch, launching the back sprays with aubepine-vitriol oil developer, show down earlier blue at 105 ℃, after the redden RF value of look be stream part of 0.4, collect this stream and part obtain component A, component A is successively by MCI Gel CHP-20 post, Toyopearl HW-40 post, hydroxypropyl dextrane gel Sephadex LH-20 post, silicagel column obtains 51mg Shaanxi galactitol glycosides I.
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| CN116789721A (en) * | 2022-10-24 | 2023-09-22 | 大理大学 | Application of farnesane sesquiterpenoids in preventing trichinosis |
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| CN116789721A (en) * | 2022-10-24 | 2023-09-22 | 大理大学 | Application of farnesane sesquiterpenoids in preventing trichinosis |
| CN116789721B (en) * | 2022-10-24 | 2024-05-28 | 大理大学 | Application of farnesane sesquiterpenoids in preventing trichinosis |
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