CN105503971A - Plant-sourced compound, preparation method and application thereof - Google Patents
Plant-sourced compound, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a plant-sourced compound and its preparation method and application. The plant-sourced compound is characterized by comprising a structural formula as shown in the formula (I). The preparation method of the plant-sourced compound comprises the following steps: Step 1, extracting a Rhodiola rosea medicinal material to obtain a water extract; Step 2, carrying out reversed-phase column chromatography separation on the water extract obtained in the Step 1, carrying out gradient elution by using 5v/v%-80 v/v% of an organic solvent aqueous solution, and collecting a component obtained after separation of 15v/v%-50 v/v% of an organic solvent aqueous solution; and Step 3, carrying out chromatographic separation and purification on the component obtained in the Step 2, and carrying out elution by using 8 v/v%-30 v/v% of an organic solvent aqueous solution so as to obtain the compound as shown in the formula (I). The organic solvent is methanol, ethanol or acetonitrile. The compound provided by the invention has good antioxidant activity and can be applied in preparation of antioxidants.
Description
Technical field
The invention belongs to anti-oxidation medicine technical field, particularly relate to a kind of phytochemical with antioxygenation, the preparation method of this compound, and the application of this compound.
Background technology
Root of Kirilow Rhodiola (formal name used at school: RhodiolaroseaL.), another name: Rhodiola rosea, sweeps sieve agate boolean (Tibetan name) etc.; For per nnial herb, high 10-20 centimetre.Root is sturdy, conical, and meat is isabelline, and the most fibrous root of collar portion tool, rhizome is short, thick shape, cylindrical, by the lepidiod leaf that most imbricate arranges.Root of Kirilow Rhodiola growth is in the high and cold pollution-free area of height above sea level 1800 ~ 2500 meters, and its growing environment is severe, thus has very strong vitality and special adaptability.Can do medicinal, can tonifying Qi clearing lung-heat, intelligence development is nourished heart, and is to act on Chinese medicine widely simply.Also there is very large cosmetic result, can skin care product be made, also edible.Function cures mainly: have tonifying Qi clearing lung-heat, intelligence development is nourished heart, effect of hemostasis with astringents, dissipating blood stasis for subsidence of swelling.Cure mainly deficiency of vital energy and physically weak, after being ill chilly, shortness of breath and fatigue, cough due to lung-heat, spitting of blood, leukorrhea diarrhoea, wound etc.
Anti-oxidant class medicine can reduce the infringement of oxyradical to vessel wall, thus plays the effect of anti-atherosclerosis.Conventional anti-oxidant class medicine comprises vitamin-E, vitamins C etc.
Alcohol has anti-oxidant, scavenging free radicals and affect the pharmacological action of arachidonic acid metabolism, has good preventive and therapeutic effect to diseases such as Parkinson's disease, alzheimer's disease, viral hepatitis.Trans-resveratrol has significant protective effect to the rat brain mitochondria caused by oxyradical, membrane phospholipid can be suppressed to degrade, mitochondrial swelling, increases membrane fluidity, improves mitochondrial state, improves resistance of oxidation 3#, 4.Its polyphenol hydroxy structure has oxidation-resistance, significantly can suppress the generation 3##4 of <+> in the oxidative damage process of hepatomicrosome, brain mitochondria and synaptosome.The antioxygenation of trans-resveratrol is that it has one of important mechanism of multi-biological effect.Research confirms that the antioxygenation of trans-resveratrol is better than vitamin-E and vitamins C, and energy scavenging free radicals, especially hydroxy radical qiao, make <+> from damage, also by suppressing the formation of glutathione disulfide, make gsh be in reduced state, thus suppress the formation of free radical.
Summary of the invention
The first object of the present invention is to provide a kind of phytochemical.
The second object of the present invention is to provide a kind of preparation method of phytochemical.
In order to realize above-mentioned first object, the invention provides a kind of phytochemical, it has structural formula shown in formula I;
In order to realize above-mentioned second object, the invention provides a kind of preparation method of phytochemical, comprising the following steps:
Step 1, extracts Root of Kirilow Rhodiola medicinal material water, obtains water extract;
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, carries out gradient elution with the aqueous solutions of organic solvent of 5v/v% ~ 80v/v%, collects 15v/v% ~ 50v/v% aqueous solutions of organic solvent and is separated the component obtained; Described organic solvent is methyl alcohol, ethanol or acetonitrile;
Step 3, component step 3 obtained carries out chromatographic separation and purification, carries out wash-out with the aqueous solutions of organic solvent of 8v/v% ~ 30v/v%, obtains compound shown in formula I; Described organic solvent is methyl alcohol, ethanol or acetonitrile.
The preparation method of the present invention's phytochemical as above, preferably, described step 1 is specially: mixed with water by Root of Kirilow Rhodiola medicinal material and carry out refluxing extraction, obtain water extract.More electedly, the weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:2 ~ 25.
The preparation method of the present invention's phytochemical as above, preferably, in described step 2, the flow velocity of gradient elution is 5mL/min ~ 100mL/min.
The preparation method of the present invention's phytochemical as above, preferably, in described step 2, described separation adopts XB-C
18post, XB-Phenyl post or XB-C
8post.
The preparation method of the present invention's phytochemical as above, preferably, in described step 3, described chromatographic separation and purification is that high performance liquid chromatography is separated, mesolow preparative chromatography is separated or normal pressure pillar layer separation.
The present invention also provides above-mentioned phytochemical preparing the application in anti-oxidation medicine.
The present invention also provides a kind of anti-oxidation medicine, comprises phytochemical described above.
The invention has the beneficial effects as follows:
The anti-oxidant activity of p-coumaricacid-4-O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranoside prepared by the present invention is similar to vitamins C, has good anti-oxidant activity.
Accompanying drawing explanation
Fig. 1 is the ESI-MS figure of compound 1 prepared by the embodiment of the present invention 1;
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of compound 1 prepared by the embodiment of the present invention 1;
Fig. 3 is the nuclear-magnetism carbon spectrogram of compound 1 prepared by the embodiment of the present invention 1;
Fig. 4 is the HSQC figure of compound 1 prepared by the embodiment of the present invention 1;
Fig. 5 is the HMBC figure of compound 1 prepared by the embodiment of the present invention 1;
Fig. 6 is the HSQC-TOCSY figure of compound 1 prepared by the embodiment of the present invention 1;
Fig. 7 is the compound 1 of the embodiment of the present invention 1 preparation
1h-
1hCOSY schemes;
Fig. 8 is the structural formula of compound shown in formula I of the present invention.
Embodiment
Be described in detail embodiment of the present invention below in conjunction with embodiment, unreceipted actual conditions person in embodiment, the condition of conveniently conditioned disjunction manufacturers suggestion is carried out.Agents useful for same or the unreceipted production firm person of instrument, being can by the conventional products of commercial acquisition.
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.More electedly, the weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:8 ~ 15.
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, carries out gradient elution with the aqueous solutions of organic solvent of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained; Described organic solvent is methyl alcohol, ethanol or acetonitrile; Reversed-phase column chromatography is separated and adopts XB-C
18post, XB-Phenyl post or XB-C
8post.
Step 3, component step 3 obtained carries out chromatographic separation and purification, carries out wash-out with the aqueous solutions of organic solvent of 8v/v% ~ 30v/v%, obtains compound shown in formula I; Described organic solvent is methyl alcohol, ethanol or acetonitrile.Described chromatographic separation and purification is that high performance liquid chromatography is separated, mesolow preparative chromatography is separated or normal pressure pillar layer separation.
Reagent used in following examples 1-5, raw material sources or specification are as follows:
Chromatographic Pure Methanol (OCEANPAK) HPLC level;
Chromatographically pure ethanol (OCEANPAK) HPLC level;
Trifluoroacetic acid aqueous solution (OCEANPAK) HPLC level;
XB-C
18post, the moon rising sun, 50*250mm, 21.2*250mm10 μm;
XB-Phenyl post, the moon rising sun, 50*250mm, 21.2*250mm10 μm;
XB-C
8post, the moon rising sun, 50*250mm, 21.2*250mm10 μm.
Embodiment 1
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.The weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:8.
Step 2, water extract step 1 obtained utilizes XB-C
18post carries out reversed-phase column chromatography separation, carries out gradient elution with the methanol aqueous solution of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained;
Step 3, component step 3 obtained carries out high performance liquid chromatography separation and purification, carries out wash-out with the methanol solution of 8v/v% ~ 30v/v%, obtains compound 1.
Embodiment 2
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.The weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:15.
Step 2, water extract step 1 obtained utilizes XB-C
8post carries out reversed-phase column chromatography separation, carries out gradient elution with the aqueous ethanolic solution of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained;
Step 3, component step 3 obtained carries out the separation and purification of mesolow preparative chromatography, carries out wash-out with the aqueous ethanolic solution of 8v/v% ~ 30v/v%, obtains compound shown in formula I.
Embodiment 3
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.The weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:10.
Step 2, water extract step 1 obtained utilizes XB-Phenyl post to carry out reversed-phase column chromatography separation, carries out gradient elution with the acetonitrile solution of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained;
Step 3, component step 3 obtained carries out normal pressure column chromatography separating purification, carries out wash-out with the acetonitrile solution of 8v/v% ~ 30v/v%, obtains compound shown in formula I.
Embodiment 4
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.The weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:2.
Step 2, water extract step 1 obtained utilizes XB-C
18post carries out reversed-phase column chromatography separation, carries out gradient elution with the acetonitrile solution of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained;
Step 3, component step 3 obtained carries out the separation and purification of mesolow preparative chromatography, carries out wash-out with the methanol aqueous solution of 8v/v% ~ 30v/v%, obtains compound shown in formula I.
Embodiment 5
The preparation method of phytochemical, comprises the following steps:
Step 1, mixes Root of Kirilow Rhodiola medicinal material with water and carries out refluxing extraction, obtain water extract.The weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:25.
Step 2, water extract step 1 obtained utilizes XB-Phenyl post to carry out reversed-phase column chromatography separation, carries out gradient elution with the acetonitrile solution of 5v/v% ~ 80v/v%, and the flow velocity of gradient elution is 5mL/min ~ 100mL/min; Collect 15v/v% ~ 50v/v% aqueous solutions of organic solvent and be separated the component obtained;
Step 3, component step 3 obtained carries out high performance liquid chromatography separation and purification, carries out wash-out with the acetonitrile solution of 8v/v% ~ 30v/v%, obtains compound shown in formula I.
Embodiment 6
Structural Identification has been carried out to the compound that above-described embodiment 1 obtains, result is see Fig. 1 ~ Fig. 7, wherein, the ESI-MS that Fig. 1 is compound shown in formula I provided by the invention schemes, Fig. 2 is the nucleus magnetic hydrogen spectrum figure of compound shown in formula I provided by the invention, the nuclear-magnetism carbon spectrogram that Fig. 3 is compound shown in formula I provided by the invention, the HSQC that Fig. 4 is compound shown in formula I provided by the invention schemes, the HMBC that Fig. 5 is compound shown in formula I provided by the invention schemes, the HSQC-TOCSY that Fig. 6 is compound shown in formula I provided by the invention schemes, Fig. 7 is compound shown in formula I provided by the invention
1h-
1hCOSY schemes.
Concrete, compound is white powder, can learn that m/z is 487.1455 [M-H] by the mass spectroscopy of Fig. 1
-(calculated value is 487.1457), and then deterministic adduct molecule formula is C
21h
28o
13.
According to characteristic peak in Fig. 2 nucleus magnetic hydrogen spectrum figure
1hNMR δ 7.56 (2H, d, J=8.8Hz), 7.12 (2H, d, J=8.8Hz) are the Hydrogen Proton signal on one group of Isosorbide-5-Nitrae substituted benzene ring; δ 7.62 (1H, d, J=16.0Hz), 6.37 (1H, d, J=16.0Hz) are the Hydrogen Proton signal of one group of trans double bond; δ 5.04 (1H, d, J=7.7Hz), 4.61 (1H, d, J=7.7Hz) are the anomeric proton signal of two β pyranose form sugar.Characteristic peak in composition graphs 3 nuclear-magnetism carbon spectrogram again
13cNMR shows 21 carbon signals, wherein has 9 for sp
2the carbon signal of hydridization, δ 170.9,160.7,145.8,130.8 (× 2), 130.1,118.0 (× 2), 117.8, point out this compound parent nucleus to be P-coumaric acid; All the other 12 is the carbon signal on 2 sugar, wherein has two end group carbon signal δ 101.4,105.3.Carrying out ownership by hsqc spectrum to part carbon signal, to observe the sub-δ of matrix 5.04 relevant to δ 101.4, and δ 4.61 is relevant to δ 105.3.By HSQC, HMBC, HMQC-TOCSY,
1h-
1hCOSY is defined as two glucose.In HMBC spectrum, wherein δ 5.04 is relevant to δ 160.7 (C-4), δ 4.61 is relevant to δ 87.6 (C-3 '), so determine that compound provided by the invention is p-Coumaric Acid-4-O-β-D-Glucopyranose-(1 → 3)-O-β-D-glucopyranoside, English name p-coumaricacid-4-O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranoside, table 1 is the nuclear magnetic data of compound shown in formula I provided by the invention.Its structure as shown in Figure 8.
The nuclear magnetic data of compound shown in table 1 formula I provided by the invention
Note: test condition is deuterated methanol,
1hNMR400MHz,
13cNMR100MHz.
The anti-oxidant experiment of embodiment 7
The antioxidation activity in vitro of p-coumaricacid-4-O-β-D-glucopyranosyl-(1 → the 3)-O-β-D-glucopyranoside adopting the present invention of DPPH radical pair to prepare is evaluated, the 0.05mmol/LDPPH ethanolic soln of the fresh configuration of 2mL is added in several 5mL centrifuge tube, add with the solution of each 300 μ L of different concns solution to be measured of dehydrated alcohol preparation, shake up, under room temperature, lucifuge leaves standstill 30min, measures the absorbancy of gained solution under 517nm (Ax) value after each concentration solution-treated to be measured respectively;
Its absorbancy (Ax) value under 517nm is measured using dehydrated alcohol as reference;
Replace solution to be measured to add centrifuge tube (inside having the 0.05mmol/LDPPH ethanolic soln of the fresh configuration of 2mL) as blank using 300 μ L dehydrated alcohols, measure absorbancy (A0) value;
Mix as sample controls using solution to be measured with 2mL dehydrated alcohol, be made into 1 successively, 0.5,0.4,0.2, the solution of 0.1mg/mL, measure its absorbancy (Ax) value, to eliminate the color of sample itself;
Using vitamins C as positive control.VC take water as solvent, be made into 1 successively, 0.5,0.4,0.2, the solution of 0.1mg/mL, measure its resistance to oxidation, experiment condition is identical with sample.
DPPH clearance rate=[1-(A
s-A
x)/A
0] × 100%;
Select IC50 value for the testing index of extract removing DPPH ability, set up sample concentration and free radical scavenging activity regression equation, calculate when clearance rate is 50%, sample concentration is IC50.When after the extract adding certain mass concentration, DPPH Free Radical Signal obviously weakens, and absorbance reduces with the increase of drug quality concentration, and clearance rate improves along with the increase of mass concentration, illustrate that extract has significant scavenging(action) to DPPH free radical, and in obvious amount-result relation.With clearance rate to drug quality concentration the regression equation, compound y=0.8303x+0.1761, R2=0.9981IC50=0.39mgmL
-1; Contrast medicine vitamins C y=0.395x+0.468, R2=0.9996, IC50=0.081mgmL
-1.
Result shows, the anti-oxidant activity of p-coumaricacid-4-O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranoside prepared by the present invention is similar to vitamins C.From above-described embodiment, compound provided by the invention has good anti-oxidant activity.
Above embodiment is only exemplary embodiment of the present invention, and be not used in restriction the present invention, protection scope of the present invention is defined by the claims.Those skilled in the art can in essence of the present invention and protection domain, and make various amendment or equivalent replacement to the present invention, this amendment or equivalent replacement also should be considered as dropping in protection scope of the present invention.
Claims (9)
1. a phytochemical, is characterized in that, has structural formula shown in formula I;
2. a preparation method for phytochemical, comprises the following steps:
Step 1, extracts Root of Kirilow Rhodiola medicinal material water, obtains water extract;
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, carries out gradient elution with the aqueous solutions of organic solvent of 5v/v%% ~ 80v/v%, collects 15v/v%% ~ 50v/v% aqueous solutions of organic solvent and is separated the component obtained; Described organic solvent is methyl alcohol, ethanol or acetonitrile;
Step 3, component step 3 obtained carries out chromatographic separation and purification, carries out wash-out with the aqueous solutions of organic solvent of 8v/v%% ~ 30v/v%, obtains compound shown in formula I; Described organic solvent is methyl alcohol, ethanol or acetonitrile.
3. the preparation method of phytochemical according to claim 2, is characterized in that, described step 1 is specially: mixed with water by Root of Kirilow Rhodiola medicinal material and carry out refluxing extraction, obtain water extract.
4. the preparation method of phytochemical according to claim 3, is characterized in that, the weight ratio of described Root of Kirilow Rhodiola medicinal material and water is 1:2 ~ 25.
5. the preparation method of the phytochemical according to any one of claim 2-4, is characterized in that, in described step 2, the flow velocity of gradient elution is 5mL/min ~ 100mL/min.
6. the preparation method of phytochemical according to claim 5, is characterized in that, in described step 2, described separation adopts XB-C
18post, XB-Phenyl post or XB-C
8post.
7. the preparation method of phytochemical according to claim 2, is characterized in that, in described step 3, described chromatographic separation and purification is that high performance liquid chromatography is separated, mesolow preparative chromatography is separated or normal pressure pillar layer separation.
8. described in a claim 1, phytochemical is preparing the application in anti-oxidation medicine.
9. an anti-oxidation medicine, comprises phytochemical described in claim 1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107513019A (en) * | 2016-06-16 | 2017-12-26 | 江苏康缘药业股份有限公司 | Compound, its preparation method and the application extracted from Rhodiola |
| CN113185560A (en) * | 2021-04-30 | 2021-07-30 | 山东省分析测试中心 | Phenolic glycoside compound and preparation method and application thereof |
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2015
- 2015-11-26 CN CN201510844554.4A patent/CN105503971B/en active Active
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107513019A (en) * | 2016-06-16 | 2017-12-26 | 江苏康缘药业股份有限公司 | Compound, its preparation method and the application extracted from Rhodiola |
| CN107513019B (en) * | 2016-06-16 | 2020-06-26 | 江苏康缘药业股份有限公司 | Compound extracted from rhodiola rosea, preparation method and application thereof |
| CN113185560A (en) * | 2021-04-30 | 2021-07-30 | 山东省分析测试中心 | Phenolic glycoside compound and preparation method and application thereof |
| CN113185560B (en) * | 2021-04-30 | 2022-07-12 | 山东省分析测试中心 | Phenolic glycoside compound and preparation method and application thereof |
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