CN104592330A - Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative - Google Patents
Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative Download PDFInfo
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Abstract
The invention belongs to the technical fields of forest chemistry and active ingredients of trees and in particular relates to a novel kaempferol derivative, namely kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside [kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside], a preparation method of the kaempferol derivative, and application of the kaempferol derivative in preparation of antibacterial products. The root and bark of Sophora japonica (Sophora japonica L.) are taken as raw materials, the preparation process is standardized and simple, and the experiment proves that the kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside has a strong effect of inhibiting strain growth.
Description
Technical field
The invention belongs to chemistry of forest product and trees activeconstituents technical field, be specifically related to be separated from Chinese scholar tree (Sophora japonica L.) root skin and obtain a kind of new kaempferol derivative and kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides [kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside] and its production and use.
Background technology
The deciduous tree that Chinese scholar tree (Sophorajaponica L.) is pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora (SophoraL.), another name Chinese scholartree, middle Chinese scholar tree, family Chinese scholartree, house lizard Chinese scholartree, spire Chinese scholartree, sophora bud tree etc., it is extensively distributed in the most area of China.The Chinese scholar tree height of tree can reach 15-25m, has root nodule, is suitable for moistening fertile soil (Yang Xin, etc., northern gardening, 2011, (19): 175-178).Document is recorded and is shown, the Chinese scholartree leaf of Chinese scholar tree, sophora flower, Chinese scholartree glue, fruit, bark and tree root all can be used as medicine (Zhao Ken field, etc., plant research, 1999,19 (3): 281-285).Till now, researchist is from Chinese scholar tree all multiple locations extraction and isolation to multiple secondary metabolite, and wherein, flavonoid compound is its main component (Zhang LB, et a1., Fitoterapia, 2013,87:89-92).
In recent years, because of many reasons, Resistant strain continues to increase, and the resistance strengthen continuously of pathogenic bacterium in the bacterial strain such as bacterium and fungi, causes clinical infection case fatality rate to continue to increase.At present, food, the world of medicine scientific research personnel are just actively devoted to find the natural bacteriostatic agent of safety, efficient, wide spectrum.Plant is the natural treasure-house of Substance, and document shows, the whole world had been reported that kind more than 1600 had and suppressed the higher plant of harmful organism, and wherein mycostatic have 94 kinds, and that presses down bacterium has 11 kinds, anti-viral have 17 kinds.Separately there is made at least 1389 kind of plant will likely as sterilant (should to iron, etc., Southwest University for Nationalities journal (natural science edition), 31 (3): 402-409).Thus, in Secondary Metabolism of Plant natural component, find the important thinking (Liu Haiyan, etc., Hebei Agricultural Sciences, 2005,21 (4): 254-257,328) that the material with bacteriostatic activity has become exploitation efficient germicide.
Summary of the invention
The object of this invention is to provide a kind of new kaempferol derivative and kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides [kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside].
Another object of the present invention is to provide the method preparing kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides from the root skin of pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora (SophoraL.) trees Chinese scholar tree (Sophora japonica L.).
3rd object of the present invention is to provide bacteriostatic activity effect purposes of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides.
Technical scheme of the present invention is summarized as follows:
Kaempferol derivative provided by the invention is the compound of following structural formula:
Compound molecule formula of the present invention is C
28h
24o
14, chemistry kaempferol-3-O-by name (4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, the English of its correspondence is called kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside.
From Chinese scholar tree root skin, prepare the method for kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, comprise the steps:
(1) the Chinese scholar tree root skin plant material of pulverizing is got, be 1: 1 ~ 1: 15 aqueous acetone solutions adding that concentration expressed in percentage by volume is 1% ~ 99% in mass ratio, normal temperature or heating or microwave or ultrasonic extraction 1 ~ 6 time, each 1 ~ 48 hour, filter, filtrate reduced in volume, to 1% ~ 20% of original volume, obtains crude extract;
(2) water of crude extract quality 1 ~ 6 times is added, stir, add the n-hexane extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, residue water layer is added the chloroform extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, will again remain water layer and add the extraction into ethyl acetate 1 ~ 6 time of crude extract quality 1 ~ 6 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through at least one of silica gel column chromatography and gel filtration chromatography.
This preparation method has that yield is high, production cost is low, the feature of technique simple specification.
Experiment confirms that kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides all has stronger restraining effect (being respectively 0.5 and 4.0 μ g/ml to the corresponding minimal inhibitory concentration of above-mentioned two kinds of bacterial strains) to the streptococcus aureus (Staphylococcus aureus) in gram-positive microorganism and the Klebsiella pneumonia (Klebsiella pneumonia) in Gram-negative bacteria, the fungistatic effect suitable (Liu Suanyan NEOMYCIN SULPHATE is respectively 0.5 and 2.0 μ g/ml to streptococcus aureus and Klebsiella pneumonia minimal inhibitory concentration) of its fungistatic effect and positive control group Liu Suanyan NEOMYCIN SULPHATE (neomycin).This shows that kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides can suppress the growth of common causative bacterial strain, can be used as efficient antiseptic-germicide and is applied to the fields such as food, healthcare products, pharmaceuticals, makeup.
Embodiment
With reference to the following example by easier, comprehend the present invention, providing embodiment is to illustrate the present invention, instead of limits the present invention by any way.
Embodiment 1:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 3 aqueous acetone solution adding that concentration expressed in percentage by volume is 70% in mass ratio, extract at room temperature 3 times, each 36 hours, and filter, filtrate reduced in volume, to 10% of original volume, obtains crude extract;
(2) water of crude extract quality 3 times is added, stir, add the n-hexane extraction 3 times of crude extract quality 3 times, be separated, residue water layer is added the chloroform extraction 3 times of crude extract quality 3 times, be separated, will again remain water layer and add the extraction into ethyl acetate 3 times of crude extract quality 3 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through silica gel column chromatography.
The Structural Identification of this compound:
The m/z [M+Na] of this compound is shown by fast atom bombardment mass spectroscopy(FABMS) (FAB MS)
+be 607, m/z [M+H]
+be 585, in conjunction with
1h NMR and
13c NMR spectrum show that its molecular formula is C
28h
24o
14.
1h NMR composes proton peak [δ 8.01 (2H, d, J=8.5Hz in (data are in table 1), H-2 ', 6 ') and δ 6.90 (2H, d, J=8.5Hz, H-3 ', 5 ')] the B ring that shows this compound is typical AA ' BB ' formula proton aromatic nucleus.Proton signal [δ 6.20 (1H, d, J=2.3Hz, H-6) and δ 6.39 (1H, d, J=2.3Hz, H-8)] shows that its A ring is Phloroglucinol type.And
13it is typical flavonol that C NMR peak data [δ 159.4 (C-2), 134.8 (C-3), 179.4 (C-4)] discloses this compound.Therefore, the aglycon of this compound is confirmed as kaempferol.
?
1during H NMR composes, show in this compound containing α-L-rhamnopyranosyloxyhy glucosides [1 terminal hydrogen δ 5.29 (1H, br s, H-1 "), methyl δ 0.95 (3H, d; J=6.1Hz; H-6 ") and δ 3.52 ~ 5.03 (4H, H-2 ", 3 ", 4 ", 5 ")].
Proton signal δ 7.09 (2H, s, H-2 " ', 6 " ') combine
13c NMR data [δ 121.9 (C-1 " '), 110.1 (C-2 " ', 6 " '), 146.4 (C-3 " ', 5 " '), 139.9 (C-4 " ')] show in this compound, to comprise a galloyl.
(1H, br s, H-1 ") have Long-Range Correlation with the carbon signal δ 134.8 (C-3) on kaempferol to the rhamnosyl terminal hydrogen δ 5.29 of this compound of HMBC spectrum display, determine that α-L-rhamnopyranosyloxyhy glucosides is connected with the C-3 position of kaempferol.And proton peak δ 5.03 (1H on rhamnosyl; dd; J=10.3Hz; J=9.7Hz; carbon signal δ on H-4 ") and galloyl 168.3 (C-7 " ') there is Long-Range Correlation, then 7 " ' number position and α-L-rhamnopyranosyloxyhy glucosides 4 " number position determining galloyl is connected.
To sum up, the structure of this compound is confirmed as kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides.
Through retrieval, this compound is the new kaempferol derivative never reported before this.This compound is white amorphous powder, and fusing point is 191 ~ 193 DEG C, specific rotation
this compound has uv-absorbing under ultraviolet lamp 254nm wavelength, and the color reaction of spraying of the iron trichloride ethanolic soln (mass percent) with 1% is deep green.In TLC test, when launching with the solvent systems of glacial acetic acid-water volume ratio 3: 47, the R of this compound
fvalue is 0.49, and when launching with the solvent systems of the trimethyl carbinol-glacial acetic acid-water volume ratio 3: 1: 1, the R of this compound
fvalue is 0.73.
Table 1. kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
1h (400MHz) and
13c NMR (100MHz) modal data (CD
3oD)
Embodiment 2:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 4 aqueous acetone solution adding that concentration expressed in percentage by volume is 60% in mass ratio, microwave extraction 4 times, each 3 hours, and filter, filtrate reduced in volume, to 8% of original volume, obtains crude extract;
(2) water of crude extract quality 2 times is added, stir, add the n-hexane extraction 4 times of crude extract quality 2 times, be separated, residue water layer is added the chloroform extraction 4 times of crude extract quality 2 times, be separated, will again remain water layer and add the extraction into ethyl acetate 4 times of crude extract quality 2 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through gel filtration chromatography.
Embodiment 3:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 2 aqueous acetone solution adding that concentration expressed in percentage by volume is 80% in mass ratio, supersound extraction 2 times, each 4 hours, and filter, filtrate reduced in volume, to 5% of original volume, obtains crude extract;
(2) water of crude extract quality 4 times is added, stir, add the n-hexane extraction 2 times of crude extract quality 4 times, be separated, residue water layer is added the chloroform extraction 2 times of crude extract quality 4 times, be separated, will again remain water layer and add the extraction into ethyl acetate 2 times of crude extract quality 4 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through gel filtration chromatography and silica gel column chromatography.
Embodiment 4:
The bacteriostatic activity of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides is evaluated with minimal inhibitory concentration method
1. experiment material
1.1 experimental strains: adopt the streptococcus aureus (Staphylococousaureus) in gram-positive microorganism and the Klebsiella pneumonia (Klebsiella pneumonia) in Gram-negative bacteria for examination bacterial classification in this experiment.Above two kinds of bacterial strains provide by Microbiological Lab of food engineering institute of University Of Science and Technology Of Tianjin.
1.2 experimental installations: isothermal vibration device, constant incubator, Bechtop etc.
1.3 candidate drug: above-mentioned kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides purity after HPLC measures is 99.9%, and the positive control group selected is the Liu Suanyan NEOMYCIN SULPHATE of broad-spectrum high efficacy.
2. operation steps: describe step in the minimal inhibitory concentration method reference literature that test adopts and carry out (Rabe T, van StadenJ, Journal of Ethnopharmacology, 2000,73,171-174).Each group of experiment all independently carries out three times, gets its mean value calculation.
Experimental result is as shown in table 2.Result shows, kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides all has stronger inhibit activities to streptococcus aureus and Klebsiella pneumonia, and its fungistatic effect is suitable with positive control group Liu Suanyan NEOMYCIN SULPHATE fungistatic effect.
Table 2. kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides and Liu Suanyan NEOMYCIN SULPHATE are to the minimal inhibitory concentration (μ g/ml) of experimental strain
Claims (3)
1. the compound of following structural formula:
Chemistry kaempferol-3-O-by name (4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, the English of its correspondence is called kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside.
2. the preparation method of claim 1 compound, is characterized in that comprising the steps:
(1) the Chinese scholar tree root skin plant material of pulverizing is got, be 1: 1 ~ 1: 15 acetonitrile solutions adding that concentration expressed in percentage by volume is 70% ~ 99% in mass ratio, normal temperature or heating or ultrasonic or microwave radiation exaraction 1 ~ 6 time, each 1 ~ 48 hour, filter, filtrate reduced in volume, to 1% ~ 20% of original volume, obtains crude extract;
(2) add the water of crude extract quality 1 ~ 6 times, stir, add the n-hexane extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, residue water layer is added the petroleum ether extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, petroleum ether layer concentrating under reduced pressure is obtained petroleum ether extraction phase;
(3) petroleum ether extraction prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through at least one of silica gel column chromatography and gel filtration chromatography.
3. the application of claim 1 compound in the antibacterial product of preparation.
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CN104961779A (en) * | 2015-05-25 | 2015-10-07 | 天津科技大学 | Caffeoyl group-containing tannin derivative, and preparation technology and application thereof |
CN105198943A (en) * | 2015-09-24 | 2015-12-30 | 安徽农业大学 | Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof |
CN105237598A (en) * | 2015-09-24 | 2016-01-13 | 安徽农业大学 | Flavone oxygen glycoside compound named as camellikaempferoside B, and preparation method and applications thereof |
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