CN103012517B - Iso-aurone glucoside compound, preparation method and application thereof - Google Patents
Iso-aurone glucoside compound, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an iso-aurone glucoside compound, a preparation method and an application of the iso-aurone glucoside compound. The iso-aurone glucoside compound is obtained by separating cassia fistula; the molecular formula is C21H2OO10; the structure formula is shown in the description: the name of the compound is 5,6-dyhydroxy iso-aurone-4'-O-beta-D-glucoside. The preparation method comprises the following steps of: treating raw material, ultrasonically extracting, carrying out silica-gel column chromatography, carrying out separating high pressure liquid chromatography separation and carrying out gel column chromatography. The invention also discloses application of the iso-aurone glucoside compound in preparation of drugs with resistance to tobacco mosaic virus. The iso-aurone glucoside compound is firstly separated from the cassia fistula; and the molecular formula and the structure can be confirmed. The iso-aurone glucoside compound has the advantages of simple and easy extraction method and simple compound structure; and the artificial synthesis is also easy to carry out. Through the half-leaf method test, the relative inhibition ratio of the compound for the tobacco mosaic virus is 32.3% and higher than the contrast ningnanmycin with the relative inhibition ratio for the tobacco mosaic virus of 28.6%, so that the compound can be used as the pilot compound for the drugs with resistance to tobacco mosaic virus.
Description
Technical field
The invention belongs to effective ingredients in plant extractive technique field, be specifically related to a kind of Aurone compound and its preparation method and application.
Background technology
Cassia fistula L. (
cassia fistula), have another name called golden anxious rain, laburnum, gold rain, Persian Chinese honey locust, Fructus cassiae fistulae (Cassia fistula L.), long fruit tree, A Bole, ox horn tree etc., Hong Kong many titles chitling beans are plants of a kind of leguminosae cassia.Cassia fistula L. extensively in the torrid zone and subtropical zone plantation, except can doing landscape tree or shade tree, its function cure mainly for profit just, strong muscle, open retardance, diarrhea.For halitosis, have sore throat, enteron aisle hot cause dysentery, sacroiliitis, stimulate the menstrual flow.Show through modern study, the pericarp of Cassia fistula L. is containing flavones (flavonoids), anthraquinone, chromone, alkaloid, sterol, triterpene, containing abundant free fatty acids, wax and hydrocarbon polymer in the seed of leather hard, containing the glycoside of unsaturated wax, aloin, hydroxyl methoxy anthraquinone and 11 seed amino acids in pulp, as arginine, leucine, methionine(Met), phenylalanine, tryptophane, aspartic acid, L-glutamic acid etc.Flavones is the biologically active substance that a class occurring in nature extensively exists, and because in plant, flavone component structure type is many, stereochemistry is complicated, has multiple biological activity, very active to the research in this field both at home and abroad; Different aurones belongs to rare flavones, because different Aurone compound has good biological activity, no matter is naturally occurring, or the different aurones glucoside compound that synthetic obtains, and all causes the extensive concern of chemist.Therefore, in further investigation Cassia fistula L., the type of flavones, has more far reaching significance to the utility value promoting Cassia fistula L..
Summary of the invention
The first object of the present invention is to provide a kind of different aurones glucoside compound; Second object is the preparation method providing this compound; 3rd object is to provide this compound preparing the application in resisting tobacco mosaic virus medicine.
The first object of the present invention is achieved in that described different aurones glucoside compound is separated from Cassia fistula L. and obtains, and its molecular formula is C
21h
20o
10, structural formula is:
This Compound nomenclature is: the different aurones of 5,6-dihydroxyl-4 '-
o-β-d-Glucose glycosides.
The second object of the present invention is achieved in that described different aurones glucoside compound and its preparation method and application comprises Feedstock treating, supersound extraction, silica gel column chromatography, high pressure liquid chromatography separation, gel filtration chromatography, is specially:
A, Feedstock treating: get Cassia fistula L. complete stool, coarse reduction 20 ~ 40 order;
B, supersound extraction: the ethanol with 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, each 4 ~ 8h, merged by extracting solution, filter, concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: by the pure dissolve with methanol of medicinal extract weight ratio 1.5 ~ 3 times amount, with silicagel column upper after the 80-100 order silica gel mixed sample of medicinal extract weight 1 ~ 3 times, take volume proportion as the chloroform-methanol gradient wash of 20:1 ~ 10:10, collect the elutriant of each several part respectively and concentrate, merging identical part with TLC monitoring;
D, high pressure liquid chromatography are separated: the elutriant getting volume proportion 7:3 part, and the methyl alcohol with 16 ~ 20% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains the crude product of the compounds of this invention;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of crude product weight ratio 1 ~ 2 times amount, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described different Aurone compound.
The third object of the present invention is achieved in that described different aurones glucoside compound is preparing the application in resisting tobacco mosaic virus medicine.
Different aurones glucoside compound of the present invention separates from Cassia fistula L. first, adopts the POP data validations such as nucleus magnetic resonance, mass spectrum, infrared spectra, UV spectrum its molecular formula and structure.The present invention's different aurones glucoside compound extracting method is simple, and compound structure is simple, and synthetic is also easy to realize.This compound is by the activity of its resisting tobacco mosaic virus of half leaf method experimental test, result proves that this compound is 32.2% to the relative inhibition of tobacco mosaic virus (TMV), higher than 28.6% of contrast Ningnanmycin, illustrate that this compound has good activity of resisting tobacco mosaic virus, can be used as the guiding compound of activity of resisting tobacco mosaic virus.
Accompanying drawing explanation
Fig. 1 is preparation method's process flow sheet of the present invention;
Fig. 2 be the compounds of this invention proton nmr spectra (
1h NMR) figure.
Fig. 3 be the compounds of this invention carbon-13 nmr spectra (
13c NMR) figure.
Fig. 4 is the main HMBC correlogram of the compounds of this invention.
Embodiment
Below in conjunction with accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
Different aurones glucoside compound of the present invention is separated and obtains from Cassia fistula L., and its molecular formula is C
21h
20o
10, structural formula is:
This Compound nomenclature is: the different aurones of 5,6-dihydroxyl-4 '-
o-β-d-Glucose glycosides (5,6-dihydroxy-
isoaurone-4′-
O-
β-D-glucopyranoside）。
Different aurones glucoside compound of the present invention and its preparation method and application comprises Feedstock treating, supersound extraction, silica gel column chromatography, high pressure liquid chromatography separation, gel filtration chromatography, is specially:
A, Feedstock treating: get Cassia fistula L. complete stool, coarse reduction 20 ~ 40 order;
B, supersound extraction: the ethanol with 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, each 4 ~ 8h, merged by extracting solution, filter, concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: by the pure dissolve with methanol of medicinal extract weight ratio 1.5 ~ 3 times amount, with silicagel column upper after the 80-100 order silica gel mixed sample of medicinal extract weight 1 ~ 3 times, take volume proportion as the chloroform-methanol gradient wash of 20:1 ~ 10:10, collect the elutriant of each several part respectively and concentrate, merging identical part with TLC monitoring;
D, high pressure liquid chromatography are separated: the elutriant getting volume proportion 7:3 part, and the methyl alcohol with 16 ~ 20% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains the crude product of the compounds of this invention;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of crude product weight ratio 1 ~ 2 times amount, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described different Aurone compound.
Described pure methyl alcohol is as eluent, and sub-bottle is collected, and as calculated with every bottle of 100 mL, so invention compound is in the 8 to the 9 bottle, i.e. 0.8 ~ 0.9 L of effluent liquid.
Alcohol concn described in step B is 70%, supersound extraction 3 times, each 6h.
Medicinal extract described in the step C pure dissolve with methanol of its weight 2 times.
Medicinal extract described in step C mixes sample with 80 ~ 100 order Silica Gel Silica gel that medicinal extract weighs 1 ~ 2 times after dissolve with methanol.
Chloroform-methanol volume proportion described in step C is 20:1,9:1,8:2,7:3,6:4,5:5.
Silicagel column described in step C medicinal extract weight 1 ~ 2 times amount 200 ~ 300 object silica gel dress post.
Moving phase described in D step is the methyl alcohol of 18%.
The pure dissolve with methanol of the crude product weight ratio described in E step 1.5 times.
Different aurones glucoside compound of the present invention is preparing the application in resisting tobacco mosaic virus medicine.
Different aurones glucoside compound of the present invention separates from Cassia fistula L. first, adopts the POP data validations such as nucleus magnetic resonance, mass spectrum, infrared spectra, UV spectrum its molecular formula and structure.The present invention's different aurones glucoside compound extracting method is simple, and compound structure is simple, and synthetic is also easy to realize.High pressure liquid chromatography of the present invention can be selected to pacify prompt logical sequence 1,100 half preparation high pressure liquid chromatography, and gel filtration chromatography step have employed Sephadex LH-20 gel column, and the gel column of other types can realize object of the present invention equally.
Tobacco of the present invention is raw materials used not to be limited by area and kind, and all can realize the present invention, to derive from the Cassia fistula L. sample in Dehong county, Yunnan, the present invention will be further described below:
Embodiment 1
Cassia fistula L. sample picks up from Dehong county, Yunnan, and Cassia fistula L. sample complete stool 5.5kg is crushed to 20 orders.Sample after pulverizing is placed in 60% ethanol supersound extraction 2 times, each 4h, merged by extracting solution, filter, concentrating under reduced pressure obtains medicinal extract 360g.In medicinal extract, add the pure methyl alcohol of 500 mL, dissolve the thick silica gel mixed sample of 80 order of rear 600g, then go up silicagel column, in silicagel column, load the 200 order silica gel of 1500 g; Take volume proportion as the chloroform-methanol mixed solvent gradient wash of 20:1,9:1,8:2,7:3,6:4,5:5, collect the elutriant of each several part respectively and concentrate, merge identical part with TLC monitoring.Get the elutriant of volume proportion 7:3 part, the methyl alcohol with 16% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18 ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains head product 0.86 g of the compounds of this invention.Add the pure methyl alcohol of 2.2 mL in the crude product, upper Sephadex LH-20 gel column after dissolving, by methanol-eluted fractions, namely the 0.8-0.9 L partial concentration of collecting wash-out effluent liquid obtains sterling 0.63 g of the compounds of this invention.
Embodiment 2
Cassia fistula L. sample picks up from Dehong county, Yunnan, and Cassia fistula L. sample complete stool 6kg is crushed to 40 orders.Sample after pulverizing is placed in 80% ethanol supersound extraction 4 times, each 8h, merged by extracting solution, filter, concentrating under reduced pressure obtains medicinal extract 410g.In medicinal extract, add the pure methyl alcohol of 900 mL, with the thick silica gel mixed sample of 100 order of 800 g after dissolving, then go up silicagel column, in silicagel column, load the 300 order silica gel of 1800 g; Take volume proportion as the chloroform-methanol mixed solvent gradient wash of 20:1,9:1,8:2,7:3,6:4,5:5, collect the elutriant of each several part respectively and concentrate, merge identical part with TLC monitoring.Get the elutriant of volume proportion 7:3 part, the methyl alcohol with 16% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains head product 0.92 g of the compounds of this invention.Add the pure methyl alcohol of 2.2 mL in the crude product, upper Sephadex LH-20 gel column after dissolving, by methanol-eluted fractions, namely the 0.8-0.9 L partial concentration of collecting wash-out effluent liquid obtains sterling 0.88 g of the compounds of this invention.
Embodiment 3
Cassia fistula L. sample picks up from Dehong county, Yunnan, and Cassia fistula L. sample complete stool 4.5kg is crushed to 30 orders.Sample after pulverizing is placed in 70% ethanol supersound extraction 3 times, each 6h, merged by extracting solution, filter, concentrating under reduced pressure obtains medicinal extract 364g.In medicinal extract, add the pure methyl alcohol of 700 mL, with the thick silica gel mixed sample of 90 order of 550 g after dissolving, then go up silicagel column, in silicagel column, load the 250 order silica gel of 900 g; Take volume proportion as the chloroform-methanol mixed solvent gradient wash of 20:1,9:1,8:2,7:3,6:4,5:5, collect the elutriant of each several part respectively and concentrate, merge identical part with TLC monitoring.Get the elutriant of volume proportion 7:3 part, the methyl alcohol with 18% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains head product 0.58 g of the compounds of this invention.Add the pure methyl alcohol of 2.2 mL in the crude product, upper Sephadex LH-20 gel column after dissolving, by methanol-eluted fractions, namely the 0.8-0.9 L partial concentration of collecting wash-out effluent liquid obtains sterling 0.46 g of the compounds of this invention.
Embodiment 4
Different aurones glucoside compound prepared by Example 3 carries out mass spectrum, infrared spectra, ultraviolet spectral analysis and nuclear-magnetism and detects, and result is: this compound is yellow jelly, UV spectrum (solvent is methyl alcohol),
max(log) 390(3.32), 260(3.58), 210(4.02) and nm; Infrared spectra (pressing potassium bromide troche)
max3423,2911,2864,1675,1657,1625,1543,1436,1352,1142,908,858,779cm
-1; High resolution mass spectrum provides quasi-molecular ion peak
m/z[431.0971 M-H]
-(calculated value 431.0978).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
21h
20o
10, degree of unsaturation is 12.Compound
1h NMR signal
δ h8.11(2H, d,
j=8.8 Hz, H-2 ', 6 ') and 6.91(2H, d,
j=8.8 Hz, H-3 ', 5 ') aromatic ring of display existence 1 AA ' BB ' type, also have in addition 2 non-couplings aromatic protons signal [
δ h6.59(1H, s, H-4) and 6.33(1H, s, H-7)], 1 independently olefinic proton signal
δ h7.79(1H, s, H-10), and 1 group of glucosyl group [
δ h5.25(1H, d,
j=7.3, H-1 ' ');
δ h3.21 ~ 3.68(6H, m, H-2 ' ', H-3 ' ', H-4 ' ', H-5 ' ', H-6 ' ')] signal.Compound
13c NMR data (see table 1) also show and there is different aurones structure and glucosyl group.According to H-10(
δ h7.79) and C-2(
δ c169.9) the relevant also different aurones structure of alleged occurrence of HMBC.H-1 ' ' in glucose (
δ h5.25 d) and C-4 ' (
δ c161.1 long-range HMBC s) are relevant confirms that glucosyl group is substituted in C-4 ', the coupling constant of glucosyl group proton H-1 ' ' (
j=7.3 Hz) show that glucose and different aurones pass through
β-glycosidic link connects.The configuration of different aurones double bond (
e-and
z-) determine by the chemical displacement value of H-10,
zthe chemical displacement value of-different aurones at high field region (7.4 ~ 7.5 ppm), if chemical displacement value low place (
δ h7.7 ~ 8.0 ppm) be then
e-isomer, the chemical displacement value of the compounds of this invention H-10 (
δ h7.79) confirm that compound is
e-isomer.Because glucosyl group substituting group position is determined in compound, the unimodal signal of two non-couplings from proton nmr spectra (
δ h6.59 and
δ h6.33) can infer that two hydroxyls are substituted in C-5 and C-6 position, the different aurones that C-5 and the C-6 position that the hydrogen spectrum of compound and carbon modal data also and were in the past reported replaces is basically identical; According to the above results, the structure of this different aurones glucoside compound can be determined.
Table 1 compound
1h and
13c NMR data (CD
3oD, 400 and 100 M Hz)
| No. | d C (m) | d H (m, J, Hz) |
| 2 | 169.9 s | |
| 3 | 120.0 s | |
| 4 | 109.4 d | 6.59, s |
| 5 | 145.0 s | |
| 6 | 147.4 s | |
| 7 | 105.1 d | 6.33, s |
| 8 | 154.5 s | |
| 9 | 118.8 s | |
| 10 | 142.6 d | 7.79, s |
| 1′ | 126.9 s | |
| 2′,6′ | 132.3 d | 8.11, d, J=8.8 |
| 3′,5′ | 115.1 d | 6.91, d, J=8.8 |
| 4′ | 161.1 s | |
| 1′′ | 104.3 d | 5.25, d, J=7.3 |
| 2′′ | 75.8 d | 3.44 m |
| 3′′ | 78.4 d | 3.42 m |
| 4′′ | 71.4 d | 3.32 m |
| 5′′ | 78.1 d | 3.21 m |
| 6′′ | 62.7 t | 3.53, 3.68 m |
Embodiment 5
Different aurones glucoside compound prepared by Example 1,2 detects according to the method for embodiment, obtains identical structure.
Embodiment 6
The different aurones glucoside compound prepared with embodiment 3, for raw material, adopts half leaf method to carry out activity of resisting tobacco mosaic virus detection.
When the mass concentration of medicament is 50 μ g/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, (leaf is capable normal to choose the blade being applicable to test, anosis without worm), first blade is evenly sprinkled fine emery powder, with writing brush, tobacco mosaic virus (TMV) source (3.0 × 10-3) for subsequent use is evenly put on the blade sprinkled with silicon carbide, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20min, take out, to spill on defoliation sheet the globule and about liquid, two and half leaves are restored and is emitted on the enamel son of an influential official cover glass being covered with toilet paper moisturizing, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3d and visible withered spot.Each process set second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition:
XI%=（CK-T）/CK×100%
Wherein:
X is relative inhibition (%);
CK is soaked in the withered spot number (individual) that half in clear water connects malicious leaf;
T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
Result shows: the relative inhibition of this compound is 32.2%, far above the relative inhibition 28.6% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (7)
1. a different aurones glucoside compound preparation method, it is characterized in that: described compound is separated and obtains from Cassia fistula L., its molecular formula is C
21h
20o
10, structural formula is:
This Compound nomenclature is: the different aurones of 5,6-dihydroxyl-4 '-
o-β-d-Glucose glycosides; Its preparation method comprises Feedstock treating, supersound extraction, silica gel column chromatography, high pressure liquid chromatography separation, gel filtration chromatography, is specially:
A, Feedstock treating: get Cassia fistula L. complete stool, coarse reduction 20 ~ 40 order;
B, supersound extraction: the ethanol with 60 ~ 80% is solvent, supersound extraction 2 ~ 4 times, each 4 ~ 8h, merged by extracting solution, filter, concentrating under reduced pressure becomes medicinal extract;
C, silica gel column chromatography: by the pure dissolve with methanol of medicinal extract weight ratio 1.5 ~ 3 times amount, with silicagel column upper after the 80-100 order silica gel mixed sample of medicinal extract weight 1 ~ 3 times, take volume proportion as the chloroform-methanol gradient wash of 20:1,9:1,8:2,7:3,6:4,5:5, collect the elutriant of each several part respectively and concentrate, merging identical part with TLC monitoring;
D, high pressure liquid chromatography are separated: the elutriant getting volume proportion 7:3 part, and the methyl alcohol with 16 ~ 20% is moving phase, take specification as 20mm × 250mm, the C of 5 μm
18preparative column is stationary phase, and flow velocity is 18ml/min, and UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, collects the chromatographic peak of 16.4min, and repeatedly cumulative rear evaporate to dryness, obtains the crude product of described compound;
E, gel filtration chromatography: upper Sephadex LH-20 gel column after the pure dissolve with methanol of crude product weight ratio 1 ~ 2 times amount, carry out wash-out with pure methyl alcohol, sub-bottle is collected, and the 0.8-0.9 L partial concentration of wash-out effluent liquid is described different aurones glucoside compound.
2. different aurones glucoside compound preparation method according to claim 1, is characterized in that: the alcohol concn described in step B is 70%, supersound extraction 3 times, each 6h.
3. different aurones glucoside compound preparation method according to claim 1, is characterized in that: the pure dissolve with methanol of its weight 2 times of the medicinal extract described in step C.
4. different aurones glucoside compound preparation method according to claim 1, is characterized in that: the medicinal extract described in step C weighs 80 ~ 100 order silica gel mixed samples of 1 ~ 2 times after dissolve with methanol with medicinal extract.
5. different aurones glucoside compound preparation method according to claim 1, is characterized in that: silicagel column medicinal extract weight 1 ~ 2 times amount 200 ~ 300 object silica gel dress post described in step C.
6. different aurones glucoside compound preparation method according to claim 1, is characterized in that: the moving phase described in D step is the methyl alcohol of 18%.
7. different aurones glucoside compound preparation method according to claim 1, is characterized in that: the pure dissolve with methanol of the crude product weight ratio described in E step 1.5 times.
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