CN104592330B - A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use - Google Patents
A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use Download PDFInfo
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- CN104592330B CN104592330B CN201510053365.5A CN201510053365A CN104592330B CN 104592330 B CN104592330 B CN 104592330B CN 201510053365 A CN201510053365 A CN 201510053365A CN 104592330 B CN104592330 B CN 104592330B
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- kaempferol
- galloyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention belongs to chemistry of forest product and trees active component technical field, and in particular to a kind of new kaempferol derivative is the O of Kaempferol 3 (4 " galloyl) α L rhamnopyranosyloxyhies glucosides [O of kaempferol 3 (4 " galloyl) α L rhamnopyranoside] and preparation method thereof and the application in antibacterial product is prepared.The present invention is with Chinese scholar tree (Sophorajapon1ca L.) root skin as raw material; its preparation technology specification is simple, and experiment proves that the O of Kaempferol 3 (4 " galloyl) growth of α L rhamnopyranosyloxyhies glucosides to bacterial strain has stronger inhibitory action.
Description
Technical field
The invention belongs to chemistry of forest product and trees active component technical field, and in particular to from Chinese scholar tree (Sophora
Japonica L.) in root skin a kind of isolated new kaempferol derivative be Kaempferol -3-O- (4 "-galloyl)-α -
L- rhamnopyranosyloxyhies glucosides [kaempferol-3-O- (4 "-galloyl)-α-L-rhamnopyranoside] and preparation method thereof
And purposes.
Background technology
Chinese scholar tree (Sophorajaponica L.) is pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora
The deciduous tree of (Sophora L.), alias Chinese scholartree, middle Chinese scholar tree, family Chinese scholartree, house lizard Chinese scholartree, spire Chinese scholartree, sophora bud tree etc., its is widely distributed
In the most area of China.The Chinese scholar tree height of tree has root nodule up to 15-25m, is suitable for moistening fertile soil (Yang Xin, etc. north
Fang Yuanyi, 2011, (19)：175-178).Document is recorded and shown, the Chinese scholartree leaf of Chinese scholar tree, sophora flower, Chinese scholartree glue, fruit, bark and tree root are all
Can be used as medicine (Zhao Ken fields, etc. plant research, 1999,19 (3)：281-285).Till now, researcher is many from Chinese scholar tree
Position is extracted and is isolated to various secondary metabolites, wherein, flavone compound is its main component (Zhang LB, et
A1., Fitoterapia, 2013,87：89-92).
In recent years, because of many reasons, antibody-resistant bacterium persistently increases, and the drug resistance of pathogenic bacteria is held in the bacterial strain such as bacterium and fungi
Continuous enhancing, causes clinical infection case fatality rate persistently to increase.At present, food, the world of medicine scientific research personnel are just actively working to find
Safe efficient, wide spectrum natural bacteriostatic agent.Plant is the natural treasure-house of Substance, and document shows that the whole world has been reported
Crossing kind more than 1600 has the higher plant for suppressing harmful organism, and wherein restraining epiphyte has 94 kinds, and that presses down bacterium has 11 kinds, anti-viral
Have 17 kinds.(opening to iron, etc. Southwest University for Nationalities separately to have at least 1389 kinds plants of information to would be possible as bactericide
Journal (natural science edition), 31 (3)：402-409).Thus, being found in Secondary Metabolism of Plant natural component has bacteriostatic activity
Material turned into exploitation efficient germicide important thinking (Liu Haiyan, etc. Hebei Agricultural Sciences, 2005,21 (4)：254-
257,328).
The content of the invention
It is an object of the invention to provide a kind of new kaempferol derivative be Kaempferol -3-O- (4 "-galloyl)-α -
L- rhamnopyranosyloxyhies glucosides [kaempferol-3-O- (4 "-galloyl)-α-L-rhamnopyranoside].
It is a further object to provide from pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora
Kaempferol -3-O- (4 "-nutgall acyls are prepared in the root skin of (Sophora L.) trees Chinese scholar tree (Sophora japonica L.)
Base)-α-L- rhamnopyranosyloxyhy glucosides method.
Third object of the present invention is to provide Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides
Bacteriostatic activity effect purposes.
Technical scheme is summarized as follows：
The kaempferol derivative that the present invention is provided is the compound of following structural formula：
Compound molecule formula of the invention is C28H24O14, chemical entitled Kaempferol -3-O- (4 "-galloyl)-α-L-
Rhamnopyranosyloxyhy glucosides, and its corresponding English entitled kaempferol-3-O- (4 "-galloyl)-α-L-
rhamnopyranoside。
The method that Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides is prepared from Chinese scholar tree root skin, bag
Include following steps：
(1) the Chinese scholar tree root skin plant material of crushing is taken, is in mass ratio that 1: 1~1: 15 addition concentration expressed in percentage by volumes are 1%
~99% aqueous acetone solution, normal temperature or heating or microwave or ultrasonic wave extraction 1~6 time, 1~48 hour every time, filtering, filtrate
The 1%~20% of original volume is concentrated under reduced pressure into, crude extract is obtained；
(2) water of 1~6 times of crude extract quality is added, stirring adds the n-hexane extraction 1~6 of 1~6 times of crude extract quality
It is secondary, separate, the chloroform that remaining water layer adds 1~6 times of crude extract quality is extracted 1~6 time, separate, remaining water layer will add again
Enter 1~6 times of crude extract quality ethyl acetate extract 1~6 time, separating ethyl acetate layer and last water layer, by ethyl acetate
Layer is concentrated under reduced pressure to obtain ethyl acetate extraction phase；
(3) ethyl acetate extraction phase prepares Kaempferol -3- through at least one of silica gel column chromatography and gel filtration chromatography
O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides.
The characteristics of preparation method has yield high, low production cost, process is simple specification.
Experiment confirms Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides in gram-positive bacteria
Friedlander's bacillus in staphylococcus aureus (Staphylococcus aureus) and Gram-negative bacteria
(Klebsiella pneumonia) has stronger inhibitory action, and (the corresponding minimal inhibitory concentration to above two bacterial strain is distinguished
It is 0.5 and 4.0 μ g/ml), its fungistatic effect (neomycin pair suitable with the fungistatic effect of positive control group neomycin (neomycin)
Staphylococcus aureus and Friedlander's bacillus minimal inhibitory concentration are respectively 0.5 and 2.0 μ g/ml).This show Kaempferol-
3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhies glucosides can suppress the growth of common causative bacterial strain, can be used as efficient antibacterial
Agent is applied to the fields such as food, health products, pharmaceuticals, cosmetics.
Specific embodiment
With reference to the following example will be easier, the present invention is more fully understood, be given embodiment be in order to illustrate the present invention,
Rather than the limitation present invention by any way.
Embodiment 1：
The preparation of Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides
(1) the Chinese scholar tree root skin plant material of crushing is taken, in mass ratio for add acetone that concentration expressed in percentage by volume be 70% at 1: 3
The aqueous solution, normal temperature is extracted 3 times, and 36 hours every time, filtering, filtrate decompression was concentrated into the 10% of original volume, obtains crude extract；
(2) water of 3 times of crude extract quality, stirring, the n-hexane extraction of 3 times of addition crude extract quality 3 times is added to separate,
The chloroform that remaining water layer adds 3 times of crude extract quality is extracted 3 times, is separated, 3 times of crude extract quality will be added by remaining water layer again
Ethyl acetate extract 3 times, separating ethyl acetate layer and last water layer to obtain ethyl acetate extraction by ethyl acetate layer is concentrated under reduced pressure
Take phase；
(3) ethyl acetate extraction phase prepares Kaempferol -3-O- (4 "-galloyl)-α-L- through silica gel column chromatography
Rhamnopyranosyloxyhy glucosides.
The Structural Identification of the compound：
The m/z [M+Na] of the compound is shown by fast atom bombardment mass spectroscopy (FAB MS)+It is 607, m/z [M+H]+It is 585,
With reference to1H NMR and13C H NMR spectroscopies show that its molecular formula is C28H24O14。
1In H H NMR spectroscopies (data are shown in Table 1) proton peak [δ 8.01 (2H, d, J=8.5Hz, H-2 ', 6 ') and δ 6.90 (2H,
D, J=8.5Hz, H-3 ', 5 ')] show the compound B rings be typical case's AA ' BB ' formula proton aromatic rings.Proton signal [δ 6.20
(1H, d, J=2.3Hz, H-6) and δ 6.39 (1H, d, J=2.3Hz, H-8)] show that its A ring is phloroglucin type.And13C NMR
Peak data [δ 159.4 (C-2), 134.8 (C-3), 179.4 (C-4)] discloses the compound for typical flavonols.Therefore, the change
The aglycon of compound is confirmed as Kaempferol.
1In H H NMR spectroscopies, show in the compound containing α-L- rhamnopyranosyloxyhies glucosides [1 terminal hydrogen δ 5.29
(1H, br s, H-1 "), a 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 " ') combine13C NMR datas [δ 121.9 (C-1 " '), 110.1 (C-
2 " ', 6 " '), 146.4 (C-3 " ', 5 " '), 139.9 (C-4 " ')] show in the compound comprising a galloyl.
HMBC spectrums show the (carbon signals on 1H, br s, H-1 ") and Kaempferol of rhamnose terminal hydrogen δ 5.29 of the compound
δ 134.8 (C-3) has Long-Range Correlation, determines that α-L- rhamnopyranosyloxyhies glucosides is connected with C-3 of Kaempferol.And matter on rhamnose
Carbon signal δ 168.3 (C-7 " ') on sub- peak δ 5.03 (1H, dd, J=10.3Hz, J=9.7Hz, H-4 ") and galloyl has
Long-Range Correlation, it is determined that the 7 of galloyl " ' number position and α-L- rhamnopyranosyloxyhies glucosides 4 " number position is connected.
To sum up, the structure of the compound is confirmed as Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranoses
Glycosides.
Through retrieval, the compound is the new kaempferol derivative never reported before this.The compound is white without fixed
Type powder, fusing point is 191~193 DEG C, optical activityThe compound is in uviol lamp 254nm
There is UV absorption under wavelength, it is dark green with 1% ferric trichloride ethanol solution (mass percent) spraying chromogenic reaction.TLC
In experiment, when being launched with the solvent system of glacial acetic acid-water volume ratio 3: 47, the R of the compoundfIt is 0.49 to be worth, and with the tert-butyl alcohol-
When the solvent system of glacial acetic acid-water volume ratio 3: 1: 1 launches, the R of the compoundfBe worth is 0.73.
Kaempferol-the 3-O- of table 1. (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides1H (400MHz) and13C NMR
(100MHz) modal data (CD3OD)
Embodiment 2：
The preparation of Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides
(1) the Chinese scholar tree root skin plant material of crushing is taken, in mass ratio for add acetone that concentration expressed in percentage by volume be 60% at 1: 4
The aqueous solution, Microwave Extraction 4 times, 3 hours every time, filtering, filtrate decompression was concentrated into the 8% of original volume, obtains crude extract；
(2) water of 2 times of crude extract quality, stirring, the n-hexane extraction of 2 times of addition crude extract quality 4 times is added to separate,
The chloroform that remaining water layer adds 2 times of crude extract quality is extracted 4 times, is separated, 2 times of crude extract quality will be added by remaining water layer again
Ethyl acetate extract 4 times, separating ethyl acetate layer and last water layer to obtain ethyl acetate extraction by ethyl acetate layer is concentrated under reduced pressure
Take phase；
(3) ethyl acetate extraction phase prepares Kaempferol -3-O- (4 "-galloyl)-α-L- through gel filtration chromatography
Rhamnopyranosyloxyhy glucosides.
Embodiment 3：
The preparation of Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides
(1) the Chinese scholar tree root skin plant material of crushing is taken, in mass ratio for add acetone that concentration expressed in percentage by volume be 80% at 1: 2
The aqueous solution, ultrasonic extraction 2 times, 4 hours every time, filtering, filtrate decompression was concentrated into the 5% of original volume, obtains crude extract；
(2) water of 4 times of crude extract quality, stirring, the n-hexane extraction of 4 times of addition crude extract quality 2 times is added to separate,
The chloroform that remaining water layer adds 4 times of crude extract quality is extracted 2 times, is separated, 4 times of crude extract quality will be added by remaining water layer again
Ethyl acetate extract 2 times, separating ethyl acetate layer and last water layer to obtain ethyl acetate extraction by ethyl acetate layer is concentrated under reduced pressure
Take phase；
(3) ethyl acetate extraction phase through gel filtration chromatography and silica gel column chromatography prepare Kaempferol -3-O- (4 "-do not eat
Sub- acyl group)-α-L- rhamnopyranosyloxyhy glucosides.
Embodiment 4：
The antibacterial of Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides is evaluated with minimal inhibitory concentration method
Activity
1. experiment material
1.1 experimental strains：For examination strain using the staphylococcus aureus in gram-positive bacteria in this experiment
Friedlander's bacillus (Klebsiella in (Staphylococous aureus) and Gram-negative bacteria
pneumonia).Both the above bacterial strain is provided by Microbiological Lab of food engineering institute of University Of Science and Technology Of Tianjin.
1.2 experimental facilities：Isothermal vibration device, constant incubator, superclean bench etc..
1.3 candidate drugs：Above-mentioned Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhies glucosides is determined through HPLC
Purity is 99.9% afterwards, and the positive control group of selection is the neomycin of broad-spectrum high efficacy.
2. operating procedure：Test use minimal inhibitory concentration method reference literature in describe step carry out (Rabe T,
Van Staden J, Journal of Ethnopharmacology, 2000,73,171-174).Each group experiment is independently carried out
Three times, take its mean value calculation.
Experimental result is as shown in table 2.Result shows, and Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranoses
Glycosides has stronger inhibitory activity to staphylococcus aureus and Friedlander's bacillus, and its fungistatic effect and positive control group are newly mould
Plain fungistatic effect is suitable.
Kaempferol-the 3-O- of table 2. (4 "-galloyl)-α-L- rhamnopyranosyloxyhies glucosides and neomycin to experimental strain most
Small Mlc (μ g/ml)
Claims (1)
1. the preparation technology of a kind of kaempferol derivative Kaempferol -3-O- (4 "-galloyl)-α-L- rhamnopyranosyloxyhy glucosides,
It is characterized in that comprising the following steps：
(1) take the Chinese scholar tree root skin plant material of crushing, be in mass ratio 1: 1~1: 15 add concentration expressed in percentage by volumes be 70%~
99% acetonitrile solution, normal temperature or adds thermally or ultrasonically or microwave radiation exaraction 1~6 time, 1~48 hour every time, filtering, filtrate
The 1%~20% of original volume is concentrated under reduced pressure into, crude extract is obtained；
(2) water of 1~6 times of crude extract quality is added, is stirred, the n-hexane extraction of 1~6 times of addition crude extract quality 1~6 time,
Separate, remaining water layer is added the petroleum ether extraction 1~6 time of 1~6 times of crude extract quality, separate, petroleum ether layer is concentrated under reduced pressure
Obtain petroleum ether extraction phase；
(3) petroleum ether extraction through at least one of silica gel column chromatography and gel filtration chromatography prepare Kaempferol -3-O- (4 " -
Galloyl)-α-L- rhamnopyranosyloxyhy glucosides.
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| CN104961779B (en) * | 2015-05-25 | 2017-09-29 | 天津科技大学 | A kind of tannins derivative and its preparation technology and application containing coffee acyl |
| CN105198943B (en) * | 2015-09-24 | 2017-12-22 | 安徽农业大学 | A kind of entitled tea hill how glycosides A acylated flavonoids glucosides and its preparation method and application |
| CN105237598B (en) * | 2015-09-24 | 2017-12-22 | 安徽农业大学 | A kind of entitled tea hill how glycosides B flavones oxygen glycosides compound and its preparation method and application |
| CN106928289B (en) * | 2017-02-22 | 2019-09-20 | 安徽农业大学 | A kind of four glucosides of acylation flavones and its extracting method and application |
| CN107312050B (en) * | 2017-08-28 | 2019-11-22 | 天津科技大学 | A kind of preparation process of galloyl flavonol glycosides in katsura tree branch |
| CN113115798B (en) * | 2021-04-23 | 2022-03-29 | 北京农学院 | Application of Chinese scholartree in biological control, biological control medicament and preparation method thereof |
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| WO2012107205A1 (en) * | 2011-02-08 | 2012-08-16 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Sweetener and/or a sweetness enhancer, sweetener compositions, methods of making the same and consumables containing the same |
| US20140271996A1 (en) * | 2013-03-14 | 2014-09-18 | Indra Prakash | Beverages containing rare sugars |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012107205A1 (en) * | 2011-02-08 | 2012-08-16 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Sweetener and/or a sweetness enhancer, sweetener compositions, methods of making the same and consumables containing the same |
| US20140271996A1 (en) * | 2013-03-14 | 2014-09-18 | Indra Prakash | Beverages containing rare sugars |
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