CN104829659B - A kind of compound and its preparation and application - Google Patents
A kind of compound and its preparation and application Download PDFInfo
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- CN104829659B CN104829659B CN201510173054.2A CN201510173054A CN104829659B CN 104829659 B CN104829659 B CN 104829659B CN 201510173054 A CN201510173054 A CN 201510173054A CN 104829659 B CN104829659 B CN 104829659B
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Abstract
The invention provides compound and its preparation and application shown in a kind of formula (I), the compound has stronger antioxidation activity.
Description
Technical field
The present invention relates to medicine extractive technique field, more particularly to a kind of compound and its preparation and application.
Background technology
Free radical, refers to the hazardous compound produced in body oxidation reaction, with strong oxidizing property, can damage the group of body
Knit and cell, and then cause chronic disease and aging effect.Modern study shows, when various factors has broken interior free yl life
Into during dynamic equilibrium with elimination, free radical will be made to exceed physiology limit, so as to cause the damage of large biological molecule, enzyme inactivation
Deng.Due to these damaging actions, the aging of body can be caused, producing various lesions includes apoplexy, heart disease, tumour, glycosuria
Disease, hyperlipidemia, chronic kidney hypofunction, nerve degenerative diseases, cataract etc..A large amount of crowds and experimental study show, rationally take
Antioxidant or free radical scavenger, can effectively control the generation of these diseases, play good prevention effect.Therefore, look for
Medicine to Green Tea Extract is always focus place of concern.
The content of the invention
In view of this, the technical problem to be solved in the present invention is to provide a kind of compound and its preparation and application, prepares
Compound have stronger antioxidation activity.
The invention provides compound shown in a kind of formula (I)：
Present invention also offers the preparation method of compound shown in a kind of formula (I), including：
A) white Peony Root is extracted with ethanol, ethanol extract is obtained；
B) by step A) obtained ethanol extract is mixed with water, and extracted respectively with ethyl acetate and n-butanol,
Obtain acetic acid ethyl ester extract and n-butyl alcohol extract；
C) by step B) obtained n-butyl alcohol extract carries out pillar layer separation, entered with ethyl acetate, methanol mixed solvent
Row gradient elution, the ethyl acetate, methanol volume ratio are (1~50):1, collect ethyl acetate, methanol volume ratio for (1~
20):1 isolated component；
D) by step C) obtained component carries out reversed-phase column chromatography separation, entered with 5%~80% aqueous solutions of organic solvent
Row gradient elution, collects the isolated component of 15%~50% aqueous solutions of organic solvent；The organic solvent is methanol, ethanol
Or acetonitrile；
E) by step D) obtained component carries out chromatographic separation and purification, carried out with 8%~30% aqueous solutions of organic solvent
Elution, obtains compound shown in formula (I)；The organic solvent is methanol, ethanol or acetonitrile；
It is preferred that, the step A) be specially：
White Peony Root is extracted with alcohol reflux, ethanol extract is obtained.
It is preferred that, the weight ratio of the white Peony Root and ethanol is 1：(8~15).
It is preferred that, the step D) in, the flow velocity of gradient elution is 3mL/min~5mL/min.
It is preferred that, the step D) in, the pillar layer separation uses C18Post, C30Post or C8Post.
It is preferred that, the step E) in, the chromatographic separation and purification is high performance liquid chromatography separation, mesolow preparation chromatogram
Separation or normal pressure pillar layer separation.
Present invention also offers application of the compound in Green Tea Extract medicine is prepared shown in a kind of formula (I),
Present invention also offers a kind of medicine for Green Tea Extract, including compound shown in formula (I),
Compared with prior art, the invention provides a kind of compound with structure shown in formula (I), it has anti-oxidant
Activity, can be used for preparing Green Tea Extract medicine.
Brief description of the drawings
The ESI-MS figures of compound shown in the formula (I) that Fig. 1 provides for the present invention；
The nucleus magnetic hydrogen spectrum figure of compound shown in the formula (I) that Fig. 2 provides for the present invention；
The nuclear-magnetism carbon spectrogram of compound shown in the formula (I) that Fig. 3 provides for the present invention；
The HSQC figures of compound shown in the formula (I) that Fig. 4 provides for the present invention；
The HMBC figures of compound shown in the formula (I) that Fig. 5 provides for the present invention；
The HMQC-TOCSY figures of compound shown in the formula (I) that Fig. 6 provides for the present invention.
Embodiment
The invention provides compound shown in a kind of formula (I)：
Above-claimed cpd has antioxidation activity, can be used for preparing Green Tea Extract medicine.
Present invention also offers the preparation method of compound shown in a kind of formula (I), including：
A) white Peony Root is extracted with ethanol, ethanol extract is obtained；
B) by step A) obtained ethanol extract is mixed with water, and extracted respectively with ethyl acetate and n-butanol,
Obtain acetic acid ethyl ester extract and n-butyl alcohol extract；
C) by step B) obtained n-butyl alcohol extract carries out reversed-phase column chromatography separation, molten with ethyl acetate, methanol mixing
Agent carries out gradient elution, and the ethyl acetate, methanol volume ratio are (1~50):1, it is (1 to collect ethyl acetate, methanol volume ratio
~20):1 isolated component；
D) by step C) obtained component carries out pillar layer separation, and ladder is carried out with 5%~80% aqueous solutions of organic solvent
Degree elution, collects the isolated component of 15%~50% aqueous solutions of organic solvent；The organic solvent is methanol, ethanol or second
Nitrile；
E) by step D) obtained component carries out chromatographic separation and purification, carried out with 8%~30% aqueous solutions of organic solvent
Elution, obtains compound shown in formula (I)；The organic solvent is methanol, ethanol or acetonitrile；
The present invention is using white Peony Root as raw material, the RADIX PAEONIAE ALBA that the white Peony Root can be known to the skilled person
Material, the present invention has no specifically limited to this.
The present invention is first extracted white Peony Root with alcohol reflux, and extract solution is concentrated to obtain ethanol extract.This
In invention, the weight ratio preferably 1 of the white Peony Root and ethanol：(8~15), more preferably 1：(9~14), the present invention's
In one specific embodiment, the weight ratio preferably 1 of the white Peony Root and ethanol：10.
Obtain after ethanol extract, it is mixed with water, obtain suspension, and carried out respectively with ethyl acetate and n-butanol
Extraction, acetic acid ethyl ester extract and n-butyl alcohol extract are respectively obtained after concentration, drying；It is currently preferred, first using acetic acid
Ethyl ester is extracted, and is then extracted using n-butanol, can make it that impurity content is less in n-butyl alcohol extract；The present invention
In, the weight of the ethyl acetate and extract is than being preferably (0.8~1.2)：1, the weight ratio of the n-butanol and extract
Preferably (0.8~1.2)：1；In the present invention, the number of times of the extraction is preferably 3~5 times.
Then, obtained n-butyl alcohol extract is subjected to pillar layer separation, present invention preferably employs silicagel column, with acetic acid second
Ester, methanol mixed solvent carry out gradient elution, and the ethyl acetate, methanol volume ratio are preferably (1~50):1, collect acetic acid second
Ester, methanol volume ratio are (1~20):1 isolated component, and concentrate.The present invention is molten to the ethyl acetate, methanol mixing
The concentration gradient of agent is simultaneously not particularly limited, and can be chosen according to actual needs, in one particular embodiment of the present invention, described
Ethyl acetate, the volume ratio of methanol are 50: 1,30: 1,20: 1,10: 1,5: 1,1: 1.In another specific embodiment of the present invention
In, after elution, it is 10 to collect ethyl acetate, methanol volume ratio:1 isolated component.
Obtain after said components, carry out reversed-phase column chromatography separation, gradient is carried out with 5%~80% aqueous solutions of organic solvent
Elution, collects the isolated component of 15%~50% aqueous solutions of organic solvent, and concentrate.More preferably collecting 18%~20% has
The isolated component of machine solvent aqueous solution.In the present invention, the organic solvent is methanol, ethanol or acetonitrile, more preferably first
Alcohol.The present invention is to the concentration gradient of the aqueous solutions of organic solvent and is not particularly limited, and can choose according to actual needs, at this
In one specific embodiment of invention, the methanol, the volume ratio of water is 5%, 10%, 20%, 30%, 40%, 50%,
60%th, 70%, 80%.In the present invention, the flow velocity of the gradient elution is preferably 3mL/min~5mL/min, more preferably
3.5mL/min~4.5mL/min.In the present invention, above-mentioned concentration is volumetric concentration.It is currently preferred, it is described to isolate and purify
Using C18Post, C30Post or C8Post.Product separation is carried out present invention preferably employs the method for reversed phase chromatography separation.
Obtain after said components, then carry out chromatographic separation and purification, washed with 8%~30% aqueous solutions of organic solvent
It is de-, you can to obtain compound shown in formula (I), the component molecular amount of collection is 493.1202 [M-H]-.It is currently preferred, it is described
Organic solvent is methanol, ethanol or acetonitrile, more preferably acetonitrile.In one particular embodiment of the present invention, the eluent
For 10% acetonitrile solution.It is described to isolate and purify preferably high performance liquid chromatography separation in the present invention.The high-efficient liquid phase color
The Detection wavelength of spectrum separation is preferably 210nm~254nm.In one particular embodiment of the present invention, the high-efficient liquid phase color
The Detection wavelength of spectrum separation is 230nm.
The present invention is to the method for above-mentioned concentration and is not particularly limited, the method for concentration that can be known in the art, the present invention
The method for being preferred to use decompression is concentrated, and is removed solvent and is obtained concentrate.
The present invention has carried out Structural Identification to obtained compound, as a result referring to Fig. 1~Fig. 6, wherein, Fig. 1 is the present invention
The ESI-MS figures of compound shown in the formula (I) of offer, the nucleus magnetic hydrogen spectrum figure of compound shown in the formula (I) that Fig. 2 provides for the present invention,
The nuclear-magnetism carbon spectrogram of compound shown in the formula (I) that Fig. 3 provides for the present invention, compound shown in the formula (I) that Fig. 4 provides for the present invention
HSQC figures, the HMBC figures of Fig. 5 compounds shown in the formula (I) that provides of the present invention, Fig. 6 is shown for the formula (I) of the invention provided
The HMQC-TOCSY figures of compound.
Specifically, can learn that m/z is 493.1202 [M-H] by Fig. 1 mass spectral analysis-(calculated value is
493.1199), and then determine that compound molecule formula is C19H26O15。
According to characteristic peak in Fig. 2 nucleus magnetic hydrogen spectrum figures1(the 2H, s), in conjunction with feature in Fig. 3 nuclear-magnetism carbon spectrograms of H NMR δ 7.16
Peak13C NMR δ 167.6,146.5,140.0,121.2,110.5, illustrate that the compound contains a galloyl；Simultaneously1H
NMR observes a sugared anomeric proton signal δ 5.42 (1H, d, J=3.4Hz),13Except the carbon of 5 galloyls in C NMR
Carbon signal on 12 sugar is shown outside signal, wherein there are two end group carbon signal δ 93.5,104.9, further according to Fig. 4~Fig. 6, is led to
Cross HSQC, HMBC, HMQC-TOCSY and determine that the glycan molecule is sucrose；And proton letter in sucrose H-3 ' positions is observed in HMBC spectrums
Number δ 5.53 is related to galloyl δ 167.6 (C=O), so determining that the compound that the present invention is provided is 3 '-O- nutgall acyls
The sucrose ,-O-galloylsucrose of English name 3 ', its structure is as follows：
All hydrocarbon signals assignments of the compound are referring to table 1, and table 1 is compound shown in the formula (I) of the invention provided
Nuclear magnetic data.
The nuclear magnetic data of compound shown in the formula (I) that the present invention of table 1 is provided
Note：Test condition is deuterated methanol,1H NMR 400MHz,13C NMR 100MHz。
Present invention also offers application of the compound in Green Tea Extract medicine is prepared shown in a kind of formula (I).By this hair
Bright embodiment understands that compound of the present invention has good Scavenging ability.
Present invention also offers a kind of medicine for Green Tea Extract, including compound shown in formula (I),
In the present invention, acceptable auxiliary material in medicine is preferably also included in the medicine.
The present invention has obtained compound shown in formula (I) by carrying out extraction research to white Peony Root, and by above-mentionedization
Compound carries out cell experiment, it is found that it has obvious inhibiting effect to free radical, and then preparing Green Tea Extract drug field tool
There is potential application.
The compound provided to further illustrate the present invention with reference to embodiment the present invention and its preparation and application
It is described in detail.
Embodiment 1
White Peony Root 10Kg, is extracted, extract solution is through the ethanol extract that is concentrated under reduced pressure to obtain with 10 times of amount alcohol refluxs.This is extracted
Thing is re-dissolved in water and suspension is made, respectively with ethyl acetate and extracting n-butyl alcohol, obtains acetic acid ethyl acetate extract and n-butanol extraction
Take liquid, through being concentrated under reduced pressure, dry after respectively obtain acetic acid ethyl ester extract and n-butyl alcohol extract, n-butyl alcohol extract utilizes silicon
Plastic column chromatography, with acetate-methanol (50: 1,30: 1,15:: 1,8: 1,5: 1,1: 1) gradient elution, evaporated per 500mL mono-
Point, take acetate-methanol (8: 1) part, after being concentrated under reduced pressure, recycle C18 pillar layer separations, with methanol-water (5%~
60%) gradient elution, the flow velocity of eluent is 3-5mL/min, and a cut is collected per 80mL, collects the elution of 18% methanol-water
Cut, after being concentrated under reduced pressure, is isolated and purified through preparing liquid phase HPLC, using C18 posts, with 230nm wavelength detectings, and 10% acetonitrile-
Water elution, obtains compound 8mg shown in formula (I), and pure ＞ 95% is detected through liquid phase.Its ESI-MS figure is shown in Fig. 1, by scheming
1 understands, its molecular weight is 493.1202 [M-H]-。
Compound progress magnetic resonance detection to preparation determines its structure, and testing result is shown in Fig. 2 and Fig. 3, and Fig. 2 is nuclear-magnetism
Hydrogen spectrogram, Fig. 3 is nuclear-magnetism carbon spectrogram, and its nuclear magnetic data is as follows：
1H NMR(400MHz,CD3OD) δ 7.16 (2H, s, H-2 ", 6 "), 5.53 (1H, d, J=7.8Hz, H-3 '), 5.42
(1H, d, J=3.4Hz, H-1), 4.39 (1H, t, J=7.8Hz, H-4 '), 3.95 (1H, m, H-5 '), 3.93 (1H, m, H-2),
3.84 (1H, m, H-6b), 3.76 (1H, dd, J=12.2,4.2Hz, H-6a), 3.83 (2H, m, H-6 '), 3.65 (1H, m, H-
1H, d, J=12.4Hz, H-1 ' b), 1H, m, H-1 ' a), 3.57,3.64 5) ((3.44 (1H, m, H-4), 3.42 (1H, m, H-3).
13C NMR(100MHz,CD3OD) δ 167.6 (C=O), 146.5 (C-3 ", 5 "), 140.0 (C-4 "), 121.2 (C-
1″),110.5(C-2″,6″),104.9(C-2′),93.5(C-1),84.4(C-5′),79.9(C-3′),74.8(C-5),74.7
(C-2),74.0(C-4′),73.1(C-3),71.2(C-4),65.2(C-1′),63.1(C-6′),62.2(C-6)。
Its structure is further detected by two-dimentional nuclear-magnetism again, testing result is shown in Fig. 4~Fig. 6, wherein, Fig. 4 carries for the present invention
The HSQC figures of compound shown in the formula (I) of confession, the HMBC figures of compound shown in the formula (I) that Fig. 5 provides for the present invention, Fig. 6 is this
The HMQC-TOCSY figures of compound shown in the formula (I) provided are provided.
From above-mentioned detection, compound prepared by the present invention has structure shown in formula (I).
Embodiment 2
White Peony Root 10Kg, is extracted, extract solution is through the ethanol extract that is concentrated under reduced pressure to obtain with 10 times of amount alcohol refluxs.This is extracted
Thing is re-dissolved in water and suspension is made, respectively with ethyl acetate and extracting n-butyl alcohol, obtains acetic acid ethyl acetate extract and n-butanol extraction
Take liquid, through being concentrated under reduced pressure, dry after respectively obtain acetic acid ethyl ester extract and n-butyl alcohol extract, n-butyl alcohol extract utilizes silicon
Plastic column chromatography, with acetate-methanol (50: 1,30: 1,15:: 1,8: 1,5: 1,1: 1) gradient elution, evaporated per 500mL mono-
Point, take acetate-methanol (8: 1) part, after being concentrated under reduced pressure, recycle C18 pillar layer separations, with methanol-water (5%~
60%) gradient elution, the flow velocity of eluent is 3-5mL/min, and a cut is collected per 80mL, collects the elution of 18% methanol-water
Cut, after being concentrated under reduced pressure, is isolated and purified, using C18 posts, with 230nm wavelength detectings, 10% acetonitrile-water through preparing liquid phase HPLC
Elution, obtains the compounds of this invention 8mg, and pure ＞ 95% is detected through liquid phase.
Structure is detected according to the identical method of embodiment 1, as a result shows that it has structure shown in formula (I).
Embodiment 3
White Peony Root 12Kg, is extracted, extract solution is through the ethanol extract that is concentrated under reduced pressure to obtain with 12 times of amount alcohol refluxs.This is extracted
Thing is re-dissolved in water and suspension is made, respectively with ethyl acetate and extracting n-butyl alcohol, obtains acetic acid ethyl acetate extract and n-butanol extraction
Take liquid, through being concentrated under reduced pressure, dry after respectively obtain acetic acid ethyl ester extract and n-butyl alcohol extract, n-butyl alcohol extract utilizes silicon
Plastic column chromatography, with acetate-methanol ((50: 1,20: 1,10:: 1,5: 1,1: 1) gradient elution, per mono- cut of 800mL, take
Acetate-methanol (5: 1) part, recycles C18 pillar layer separations after being concentrated under reduced pressure, with methanol-water (10%~80%) ladder
Degree elution, the flow velocity of eluent is 3-5mL/min, and a cut is collected per 120mL, 22% methanol-water eluting fraction is collected, subtracts
Isolated and purified after pressure concentration through preparing liquid phase HPLC, using C18 posts, with 230nm wavelength detectings, the elution of 10% acetonitrile-water is obtained
The compounds of this invention 3mg, pure ＞ 95% is detected through liquid phase.
Structure is detected according to the identical method of embodiment 1, as a result shows that it has structure shown in formula (I).
The anti-oxidant experiment of embodiment 4
3 '-the O-galloylsucrose prepared using DPPH free radicals to the present invention antioxidation activity in vitro is commented
Valency, adds the 0.05mmol/L DPPH ethanol solutions of the fresh configurations of 2mL in 5mL centrifuge tubes, adds what is prepared with absolute ethyl alcohol
Various concentrations (specific concentration is how many) each 300 μ L of solution to be measured, shake up, and lucifuge stands 30min at room temperature, with absolute ethyl alcohol
Its absorbance (As) value under 517nm is determined as reference, blank pair is used as instead of solution to be measured using 300 μ L absolute ethyl alcohols
According to determining its absorbance (A0) value, mixed using sample solution with 2mL absolute ethyl alcohols as sample controls, determine its absorbance
(Ax) value, to eliminate the color of sample itself, and using vitamin C as positive control, experimental result is shown in Table 2, and table 2 is the present invention
The anti-oxidant experimental result of embodiment 2 collects.
DPPH clearance rates=[1- (As- Ax)/A0] × 100%
The anti-oxidant experimental result of 2 embodiment of table 2 collects
According to the data of table 2, it is seen then that 3 '-O-galloylsucrose prepared by present invention antioxidation activity is better than dimension
Raw element C.
From above-described embodiment, the compound that the present invention is provided has good antioxidation activity.
The explanation of above example is only intended to the method and its core concept for helping to understand the present invention.It should be pointed out that pair
, under the premise without departing from the principles of the invention, can also be to present invention progress for those skilled in the art
Some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (9)
1. compound shown in a kind of formula (I)：
2. the preparation method of compound shown in a kind of formula (I), including：
A) white Peony Root is extracted with ethanol, ethanol extract is obtained；
B) by step A) obtained ethanol extract is mixed with water, and extracted respectively with ethyl acetate and n-butanol, obtain
Acetic acid ethyl ester extract and n-butyl alcohol extract；
C) by step B) obtained n-butyl alcohol extract carries out pillar layer separation, and ladder is carried out with ethyl acetate, methanol mixed solvent
Degree elution, the ethyl acetate, methanol volume ratio are (1~50):1, it is (1~20) to collect ethyl acetate, methanol volume ratio:1
Isolated component；
D) by step C) obtained component carries out reversed-phase column chromatography separation, and ladder is carried out with 5%~80% aqueous solutions of organic solvent
Degree elution, collects the isolated component of 15%~50% aqueous solutions of organic solvent；The organic solvent is methanol, ethanol or second
Nitrile；
E) by step D) obtained component carries out chromatographic separation and purification, eluted with 8%~30% aqueous solutions of organic solvent,
Obtain compound shown in formula (I)；The organic solvent is methanol, ethanol or acetonitrile；
3. preparation method according to claim 2, it is characterised in that the step A) be specially：
White Peony Root is extracted with alcohol reflux, ethanol extract is obtained.
4. preparation method according to claim 3, it is characterised in that the weight ratio of the white Peony Root and ethanol is 1：(8
~15).
5. preparation method according to claim 2, it is characterised in that the step D) in, the flow velocity of gradient elution is
3mL/min~5mL/min.
6. preparation method according to claim 2, it is characterised in that the step D) in, the separation uses C18Post, C30
Post or C8Post.
7. preparation method according to claim 2, it is characterised in that the step E) in, the chromatographic separation and purification is
High performance liquid chromatography separation, mesolow prepare chromatographic isolation or normal pressure pillar layer separation.
8. application of the compound in Green Tea Extract medicine is prepared shown in a kind of formula (I),
9. a kind of medicine for Green Tea Extract, including compound shown in formula (I),
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3596622B2 (en) * | 1993-11-08 | 2004-12-02 | 株式会社ノエビア | External preparation for preventing skin aging |
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2015
- 2015-04-13 CN CN201510173054.2A patent/CN104829659B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| Galloylsucroses from rhubarbs.;Yoshiki Kashiwada, et al.,;《Phytochemrstry》;19881231;第70卷(第5期);第1469-1472页. * |
| 杭白芍的化学成分.;李彬等，;《药学与临床研究》;20090630;第17卷(第3期);第204-206页. * |
| 白芍的化学成分研究.;张晓燕等，;《沈阳药科大学学报》;20010131;第18卷(第1期);第30-32页. * |
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