CN103880896B - Lithocarpus polystachyus (wall) Rehd separates novel dihydrochalcone glycosides compound and preparation method thereof - Google Patents
Lithocarpus polystachyus (wall) Rehd separates novel dihydrochalcone glycosides compound and preparation method thereof Download PDFInfo
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- CN103880896B CN103880896B CN201410028298.7A CN201410028298A CN103880896B CN 103880896 B CN103880896 B CN 103880896B CN 201410028298 A CN201410028298 A CN 201410028298A CN 103880896 B CN103880896 B CN 103880896B
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Abstract
The present invention relates to a kind of natural drug, be specifically related to a kind of new dihydrochalcone glycosides compound and preparation method thereof in Lithocarpus polystachyus (wall) Rehd.The present invention provides a kind of new dihydrochalcone glycosides compound and preparation method thereof, and described novel dihydrochalcone glycosides compound is isolated from Lithocarpus polystachyus (wall) Rehd, the structure formula (I) of this compound.The preparation method of described formula (I) compound: a. explosion；B. extract；C. concentrate；D. separate.
Description
Technical field
The present invention relates to isolated and purified a kind of novel dihydrochalcone glycosides compound and preparation method thereof from Lithocarpus polystachyus (wall) Rehd, belong to
In phytochemistry extraction process technology field.
Background technology
Dihydrochalcone-like compound is the compound that a class has benzchromones mother nucleus structure, for chalcone α, β
The plants such as position double bond hydrogenation forms, and this type is less in plant kingdom's distribution, can be Compositae, Rosaceae, Liliaceae separate
Arrive.
Dihydrochalcone-like compound is a class bioactive substance, has an antioxidation, antitumor, and anti-diabetic is antibacterial
And the effect such as estrogen.
Lithocarpus polystachyus (wall) Rehd, is mainly derived from being dried of Fagaceae Lithocarpus Polystachys (Wall.) Rena
Leaf, the compound of isolated from Lithocarpus polystachyus (wall) Rehd, by literature search, this is novel dihydrochalcone glycosides compound, its separation side
Method also has no that document is reported.
Summary of the invention
It is an object of the invention to provide a kind of novel dihydrochalcone glycosides compound in Lithocarpus polystachyus (wall) Rehd；
Further object is that the method for separating and preparing that a kind of noval chemical compound is provided；
Third object of the present invention is to provide the authentication method of a kind of noval chemical compound.
A kind of novel dihydrochalcone glycosides compound isolated and purified from Lithocarpus polystachyus (wall) Rehd of the present invention, it is characterised in that have with
Lower molecular formula and structural formula:
Molecular formula is: C26H31O14
Structural formula is:
Chemical name is: 4 ', 6 ', 4-trihydroxy-dihydrochalcone-2 '-β-D-Glucose-(6 ' → 1 ' ')--L-I
Primary glucosides
The present invention can also be prepared as the compound containing structure above and salt thereof or derivant.Wherein this compound
Salt or derivant can be but not limited to following several:
A. the hydroxyl on this compound flavone parent nucleus can separately or concurrently methylate, and generates methyl-derivatives, topology example
For:
Ⅰ
Ⅱ
Ⅲ
Ⅳ
Ⅴ
B. the hydroxyl on this compound flavone parent nucleus can be separately or concurrently in Na+, K+Slaine is formed Deng metal ion reaction
Derivant, example derivant structure is:
Ⅰ
Ⅱ
Ⅲ
C. the 5-hydroxyl on this compound and A, B derivant flavone parent nucleus, 4-carbonyl can be with Al+,Mg+Gold is formed Deng combining
Belong to complex.Structural formula is as follows:
D. this compound and A, derivant described in B, C can occur intramolecular dehydration, and example derivant structure is as follows:
The preparation method of a kind of novel dihydrochalcone glycosides compound isolated and purified from Lithocarpus polystachyus (wall) Rehd of the present invention, its feature
It is that there is following technical process and step:
A. Lithocarpus polystachyus (wall) Rehd medicinal material coarse powder, adds 70% alcohol reflux 2 ~ 4 times of 10 times of volumes, united extraction liquid, reduces pressure back
Receiving to without alcohol taste, with 80 DEG C of heating in water bath of distilled water, stir to all dissolvings, dislocation is in separatory funnel.Add ethyl acetate
Extracting 3 ~ 5 times, water layer discarded, ethyl acetate layer is collected, and is concentrated into thick shape through decompression Rotary Evaporators.
B. above-mentioned ethyl acetate extract is dissolved with 50% methanol, use ODS column chromatography, with 20%, 30%, 40% methanol gradient
Eluting；Each gradient elution total amount is 3 or 4 times of column volumes；Each gradient is divided into 9 or 12 fractions, a total of 27 or 36
Fraction；According to the analysis of polyam ide TLC chromatograph, take 4-7 bottle eluate or 5-10 bottle eluate decompression Rotary Evaporators
Concentrate dry, obtain methanol-water extract.
C. said extracted thing again with methanol is dissolved, add the polyamide that a certain amount of granularity is 100-200 mesh, stir
Mix uniformly；After methanol volatilizees, upper polyamide column；Carrying out gradient elution with alcohol-water, ethanol content is respectively 20%, and 30%,
40%；Each gradient elution total amount is 3 or 4 times of column volumes；Each gradient is again divided into 9 or 12 fractions, a total of 27 or 36
Individual fraction；According to polyam ide TLC plate and the assay of high-efficient liquid phase analysis chromatograph, collect 5-7 fraction or 7-10 fraction
Inject high performance liquid preparative chromatography instrument purification, discard impurity peaks, collect main constituent peak.
D. the rotated evaporimeter of composition of above-mentioned gained after purification is concentrated, in 60 DEG C of vacuum drying, i.e. obtain new dihydro
Chalcone derivative glycoside compound.
The condition of above-mentioned preparative chromatograph is as follows: chromatographic column is with octadecylsilane chemically bonded silica as filler, and flowing is mutually
Methanol: water=40:60, flow velocity is v=15ml/min, and column temperature is room temperature, and detection wavelength is 280nm.
Its outward appearance of novel dihydrochalcone glycoside compound of the inventive method gained is crocus colloid substance, is dissolved in water, first
Alcohol.
Accompanying drawing explanation
Fig. 1 be the compounds of this invention carbon-13 nmr spectra spectrogram (13C-NMR)
Fig. 2 be the compounds of this invention proton nmr spectra spectrogram (1H-NMR)
Fig. 3 is the UV spectrogram of the compounds of this invention
Fig. 4 is the IR spectrogram of the compounds of this invention
Fig. 5 is the hsqc spectrum figure of the compounds of this invention
Fig. 6 is the structural formula of the compounds of this invention
Specific embodiments
By the description of detailed description below, the present invention is further described, but described and be only the preferable of the present invention
Embodiment, is not limitation of the present invention, and the amendment that those skilled in the art make according to the basic conception of invention, as long as not
Depart from the basic thought of the present invention, all within protection scope of the present invention.
Embodiment 1: Lithocarpus polystachyus (wall) Rehd medicinal material coarse powder 500g, adds 70% alcohol reflux 2 ~ 4 times of 10 times of volumes, united extraction
Liquid, recovered under reduced pressure, to without alcohol taste, with 80 DEG C of heating in water bath of distilled water, stirs to all dissolvings, and dislocation is in separatory funnel.Add
Ethyl acetate extracts 3 ~ 5 times, water layer discarded, and ethyl acetate layer is collected, and is concentrated into thick shape through decompression Rotary Evaporators.Use ODS post
Chromatography (column volume is 600ml), with 20%, 30%, 40% methanol elution gradient；Each gradient elution total amount is 3 times of column volumes；Often
One gradient is divided into 9 fractions, a total of 27 fractions；According to the analysis of polyam ide TLC chromatograph, take 4-7 bottle eluate and wash
De-thing decompression Rotary Evaporators concentrates dry, obtains methanol-water extract.This extract again with methanol is dissolved, adds 30g's
Granularity is the polyamide of 100-200 mesh, stirs；After methanol volatilizees, upper polyamide column (column volume is 600ml)；
Carrying out gradient elution with alcohol-water, ethanol content is respectively 20%, and 30%, 40%；Each gradient elution total amount is 3 times of column volumes；
Each gradient is again divided into 9 fractions, a total of 27 fractions；According to polyam ide TLC plate and high-efficient liquid phase analysis chromatograph
Assay, collects 5-7 fraction and injects high performance liquid preparative chromatography instrument purification, discard impurity peaks, collect main constituent peak.By pure
After change the rotated evaporimeter of the composition of gained concentrate, in 60 DEG C of vacuum drying, i.e. obtaining outward appearance is yellow colloidal material, i.e. this
Bright target product 20mg.
The condition of above-mentioned preparative chromatograph is as follows: chromatographic column is with octadecylsilane chemically bonded silica as filler, and flowing is mutually
Methanol: water=40:60, flow velocity is v=15ml/min, and column temperature is room temperature, and detection wavelength is 280nm.
Embodiment 2: the Structural Identification of the yellow jelly obtained by above-described embodiment obtained by embodiment 1
Target compound of the present invention, yellow colloidal, Molish reacting positive.It is dissolved in hot water, methanol, ethanol, acetone, insoluble
In petroleum ether, ethyl acetate.TLC(polyamide film, developing solvent: ethyl acetate: methanol: glacial acetic acid: water (15:2:1:1), second
Acetoacetic ester: methanol: formic acid: water (15:1.5:1:1), water: n-butyl alcohol: acetone: formic acid (8:1:1:0.5) etc., developer: 5%
AlCl3 ethanol solution) aobvious blue-fluorescence speckle, the reaction of HCl-Mg powder does not show color, after reacting with magnesium acetate under uviol lamp in
The glimmering color of sky blue.
As follows through wave spectrum analysis the data obtained:
H-NMR:7. 03 (2H, d), 6.64 (2H, d), often group proton all show as doublet, show above being
The signal characteristic of B ring H in flavone structure, and show that B ring is symmetrical structure；5.93(d, 1.0h), 6.13(d, 1.0h), coupling constant
Being 2.1.0hz, this should be 3 '-H and 5 '-H long-range coupling and splitting of causing is divided into bimodal.4.57(t, 2H), 2.81(t,
2H) being respectively the mutual coupled signal in α, β position, triplet, wherein α position is affected by C=O, is in low field, so chemical shift is than β position
Height, this result verification dihydrochalcone structure of compound；4.93(d, 1.0h, J=7.2) it is the anomeric proton of glucose
C1 ' '-H signal, chemical shift is multiple for remaining 6 proton signal on sugar between 3.16-3.73.
13C-NMR:204.7ppm is C=O signal peak.Other signals assignment is shown in Table 1.
Claims (4)
1. a novel dihydrochalcone glycosides compound isolated and purified from Lithocarpus polystachyus (wall) Rehd, its outward appearance is crocus colloid substance,
There is following molecular formula and structural formula:
Molecular formula is: C26H31O14
Structural formula is:
Chemistry is entitled: 4 ', 6 ', 4-trihydroxy-dihydrochalcone-2 '-β-D-Glucose-(6 ' → 1 ")--L-arabinose glycosides.
2. the method for novel dihydrochalcone glycoside compound described in isolated and purified claim 1 from Lithocarpus polystachyus (wall) Rehd, it is characterised in that
There is following technical process and step:
A. take a certain amount of Lithocarpus polystachyus (wall) Rehd explosion powder, dissolve in 70 DEG C of stirred in water bath with the distilled water of 10 times amount.After dissolving completely
Being placed in separatory funnel, add ethyl acetate and extract 3-5 time, water layer discarded, ethyl acetate layer is collected, dense through decompression Rotary Evaporators
It is reduced to thick shape；
B. above-mentioned ethyl acetate extract is dissolved with 50% methanol, use ODS column chromatography, with 20%, 30%, 40% methanol gradient
Eluting；Each gradient elution total amount is 3 or 4 times of column volumes；Each gradient is divided into 9 or 12 fractions, a total of 27 or 36
Fraction；According to the analysis of polyam ide TLC chromatograph, take 4-7 bottle eluate or 5-10 bottle eluate decompression Rotary Evaporators
Concentrate dry, obtain methanol-water extract；
C. said extracted thing again with methanol is dissolved, upper polyamide column；Carrying out gradient elution with alcohol-water, ethanol content is respectively
It is 20%, 30%, 40%；Each gradient elution total amount is 3 or 4 times of column volumes；Each gradient is again divided into 9 or 12 and evaporates
Point, a total of 27 or 36 fractions；According to polyam ide TLC plate and the assay of high-efficient liquid phase analysis chromatograph, collect 5-7
Fraction or 7-10 fraction inject high performance liquid preparative chromatography instrument purification, discard impurity peaks, collect main constituent peak；
D. the rotated evaporimeter of composition of above-mentioned gained after purification is concentrated, in 60 DEG C of vacuum drying, i.e. obtain new dihydro and look into ear
Glycoside compounds.
The preparation side of a kind of novel dihydrochalcone glycoside compound isolated and purified from Lithocarpus polystachyus (wall) Rehd the most according to claim 2
Method, it is characterised in that the condition of described preparative chromatograph is: chromatographic column, with octadecylsilane chemically bonded silica as filler, flows
Dynamic is methanol mutually: water=40:60, flow velocity is v=15ml/min, and column temperature is room temperature, and detection wavelength is 280nm.
The preparation method of novel dihydrochalcone glycoside compound the most according to claim 2, it is characterised in that when using post color
Spectrum is with polyamide for fixing phase time, and chromatography polyamide used is 120 mesh resins, and eluant used is that alcohol-water enters
Row gradient elution, ethanol content is respectively 20%, and 30%, 40%.
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Citations (3)
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| CN101709316A (en) * | 2009-10-30 | 2010-05-19 | 华南理工大学 | Method for synthesizing new hesperidin through high-flux enzyme process |
| CN101775050A (en) * | 2010-01-04 | 2010-07-14 | 广东省食品工业研究所 | Alpha-glucose-based new hesperidin dihydrochalcone as well as preparation method and application thereof |
| CN102351921A (en) * | 2011-08-23 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Preparation method of neohesperidin dihydrochalcone |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101709316A (en) * | 2009-10-30 | 2010-05-19 | 华南理工大学 | Method for synthesizing new hesperidin through high-flux enzyme process |
| CN101775050A (en) * | 2010-01-04 | 2010-07-14 | 广东省食品工业研究所 | Alpha-glucose-based new hesperidin dihydrochalcone as well as preparation method and application thereof |
| CN102351921A (en) * | 2011-08-23 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Preparation method of neohesperidin dihydrochalcone |
Non-Patent Citations (4)
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| Dihydrochalcone glycosides from Oxytropis myriophylla.;Gaimei She, et al.,;《Chemistry Central Journal》;20111109;第5卷(第71期);第1-3页 * |
| New dihydrochalcone glycosides from Lithocarpus litseifolius and the phenomenon of C–H→C–D exchange observed in NMR spectra of phenolic components.;Zhen-Hua Chen, et al.,;《Journal of Asian Natural Products Research》;20090605;第11卷(第6期);第508-513页 * |
| RSLC快速测定多穗柯甜茶中5种甜味成分.;何春年等，;《中国中药杂志》;20120430;第37卷(第7期);第961-965页 * |
| 野金柴化学成分的分离和研究.;金弘昕等，;《中成药》;20121231;第34卷(第12期);第2362-2364页 * |
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