CN105503971B - A kind of phytochemical, preparation method and application - Google Patents
A kind of phytochemical, preparation method and application Download PDFInfo
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- CN105503971B CN105503971B CN201510844554.4A CN201510844554A CN105503971B CN 105503971 B CN105503971 B CN 105503971B CN 201510844554 A CN201510844554 A CN 201510844554A CN 105503971 B CN105503971 B CN 105503971B
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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Abstract
The present invention discloses a kind of phytochemical, preparation method and application, phytochemical, which is characterized in that has structural formula shown in formula (I).The preparation method of phytochemical, includes the following steps：Step 1, root of kirilow rhodiola medicinal material is extracted with 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 the isolated component of 15v/v%~50v/v% aqueous solutions of organic solvent；Step 3, component step 2 obtained carries out chromatographic separation and purification, is eluted with the aqueous solutions of organic solvent of 8v/v%~30v/v%, obtains compound shown in formula (I)；The organic solvent is methanol, ethyl alcohol or acetonitrile.Compound provided by the invention has good antioxidant activity, can be applied to prepare anti-oxidation medicine.
Description
Technical field
The invention belongs to anti-oxidation medicine technical fields, more particularly to a kind of plant source chemical combination with antioxidation
The application of object, the preparation method of the compound and the compound.
Background technique
Root of kirilow rhodiola (scientific name：Rhodiola rosea L.), alias：Rhodiola rosea sweeps sieve Ma boolean (hiding name) etc.；For
Herbaceos perennial, it is 10-20 centimetres high.Root thickness are strong, and cone, meat is isabelline, and rootstock has most fibrous roots, and rhizome is short,
Thick shape, cylindrical, the squamaceous leaf arranged by most imbricates.Root of kirilow rhodiola is grown in 1800~2500 meters of height above sea level high and cold no dirts
Area is contaminated, growing environment is severe, thus has very strong vitality and special adaptability.Can make it is medicinal, can tonifying Qi it is clear
Lung, intelligence development nourishing heart are to act on extensive Chinese medicine simply.Also there is very big cosmetic result, skin care item can be made, it is also edible.Function
It cures mainly：There is the effect of tonifying Qi clearing lung-heat, intelligence development nourishing heart, controlling of bleeding with astringents, eliminating stasis to subdue swelling.Cure mainly that deficiency of vital energy and physically weak, chilly, shortness of breath are weary after being ill
Power, cough with lung heat, hemoptysis, leukorrhea diarrhea, traumatic injury etc..
Anti-oxidant class drug can reduce damage of the oxygen radical to vascular wall, to play the role of anti-atherosclerosis.
Common anti-oxidant class drug includes vitamin E, vitamin C etc..
Alcohol have it is anti-oxidant, remove free radical and influence arachidonic acid metabolic pharmacological action, to Parkinson's disease,
The diseases such as Alzheimer disease, virus hepatitis have preferable preventive and therapeutic effect.Resveratrol is to rat caused by oxygen radical
Brain mitochondria has significant protective effect, membrane phospholipid can be inhibited to degrade, mitochondrial swelling, increases membrane fluidity, improves mitochondria
Energetic supersession state, improve oxidation resistance 3#, 4.Its polyphenol hydrogen-oxygen based structures has inoxidizability, can significantly inhibit liver particle
During the oxidative damage of body, brain mitochondria and synaptosome<+>Generation 3##4.The antioxidation of resveratrol is that it has
One of the important mechanism of multi-biological effect.Research confirms that the antioxidation of resveratrol is better than vitamin E and vitamin
C, and free radical, especially hydroxy radical can be removed, make<+>From damage, it can also pass through the shape of inhibition glutathione disulfide
At making glutathione be in reducing condition, to inhibit 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 that above-mentioned first purpose, the present invention provide a kind of phytochemical, with structure shown in formula (I)
Formula；
In order to realize that above-mentioned second purpose, the present invention provide a kind of preparation method of phytochemical, including following step
Suddenly：
Step 1, root of kirilow rhodiola medicinal material is extracted with water, obtains water extract；
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, with the organic of 5v/v%~80v/v%
Solvent aqueous solution carries out gradient elution, collects the isolated component of 15v/v%~50v/v% aqueous solutions of organic solvent；It is described
Organic solvent is methanol, ethyl alcohol or acetonitrile；
Step 3, component step 2 obtained carries out chromatographic separation and purification, with the water-organic solvent of 8v/v%~30v/v%
Solution is eluted, and compound shown in formula (I) is obtained；The organic solvent is methanol, ethyl alcohol or acetonitrile.
The preparation method of present invention phytochemical as described above, it is preferable that the step 1 is specially：By red scape
Its medicinal material is mixed with water carries out refluxing extraction, obtains water extract.More electedly, the weight ratio of the root of kirilow rhodiola medicinal material and water is
1:2~25.
The preparation method of present invention phytochemical as described above, it is preferable that in the step 2, gradient elution
Flow velocity is 5mL/min~100mL/min.
The preparation method of present invention phytochemical as described above, it is preferable that in the step 2, the separation is adopted
Use XB-C18Column, XB-Phenyl column or XB-C8Column.
The preparation method of present invention phytochemical as described above, it is preferable that in the step 3, the chromatography point
It is high performance liquid chromatography separation, mesolow preparation chromatographic isolation or normal pressure pillar layer separation from purifying.
The present invention also provides above-mentioned phytochemicals to prepare the application in anti-oxidation medicine.
The present invention also provides a kind of anti-oxidation medicines, include phytochemical as described above.
The beneficial effects of the invention are as follows：
P-coumaric acid-4-O- β-D-glucopyranosyl- (1 → 3)-O- β-D- prepared by the present invention
The antioxidant activity of glucopyranoside is similar to vitamin C, has good antioxidant activity.
Detailed description of the invention
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 compound 1 prepared by the embodiment of the present invention 11H-1HCOSY figure；
Fig. 8 is the structural formula of compound shown in formula (I).
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, actual conditions are not specified in embodiment
Person carries out according to conventional conditions or manufacturer's recommended conditions.Reagents or instruments used without specified manufacturer, being can be with
Conventional products that are commercially available.
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.More electedly, the red scape
The weight ratio of its medicinal material and water is 1:8~15.
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, with the organic of 5v/v%~80v/v%
Solvent aqueous solution carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/v%~50v/
The isolated component of v% aqueous solutions of organic solvent；The organic solvent is methanol, ethyl alcohol or acetonitrile；Reversed-phase column chromatography separation
Using XB-C18Column, XB-Phenyl column or XB-C8Column.
Step 3, component step 2 obtained carries out chromatographic separation and purification, with the water-organic solvent of 8v/v%~30v/v%
Solution is eluted, and compound shown in formula (I) is obtained；The organic solvent is methanol, ethyl alcohol or acetonitrile.The chromatographic isolation is pure
Turn to high performance liquid chromatography separation, mesolow preparation chromatographic isolation or normal pressure pillar layer separation.
Reagent used in following example 1-5, raw material sources or specification are as follows：
HPLC grades of Chromatographic Pure Methanol (OCEANPAK)；
HPLC grades of chromatography straight alcohol (OCEANPAK)；
HPLC grades of trifluoroacetic acid aqueous solution (OCEANPAK)；
XB-C18Column, the moon rising sun, 10 μm of 50*250mm, 21.2*250mm；
XB-Phenyl column, the moon rising sun, 10 μm of 50*250mm, 21.2*250mm；
XB-C8Column, the moon rising sun, 10 μm of 50*250mm, 21.2*250mm.
Embodiment 1
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.The root of kirilow rhodiola medicinal material with
The weight ratio of water is 1:8.
Step 2, water extract step 1 obtained utilizes XB-C18Column carry out reversed-phase column chromatography separation, with 5v/v%~
The methanol aqueous solution of 80v/v% carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/
The isolated component of v%~50v/v% aqueous solutions of organic solvent；
Step 3, component step 2 obtained carries out high performance liquid chromatography separation purifying, with the first of 8v/v%~30v/v%
Alcohol liquid is eluted, and compound 1 is obtained.
Embodiment 2
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.The root of kirilow rhodiola medicinal material with
The weight ratio of water is 1:15.
Step 2, water extract step 1 obtained utilizes XB-C8Column carry out reversed-phase column chromatography separation, with 5v/v%~
The ethanol water of 80v/v% carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/
The isolated component of v%~50v/v% aqueous solutions of organic solvent；
Step 3, the component that step 2 obtains is subjected to mesolow and prepares chromatographic separation and purification, with 8v/v%~30v/v%'s
Ethanol water is eluted, and compound shown in formula (I) is obtained.
Embodiment 3
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.The root of kirilow rhodiola medicinal material with
The weight ratio of water is 1:10.
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation using XB-Phenyl column, with 5v/v%
The acetonitrile solution of~80v/v% carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/
The isolated component of v%~50v/v% aqueous solutions of organic solvent；
Step 3, component step 2 obtained carries out normal pressure column chromatography separating purification, with the acetonitrile of 8v/v%~30v/v%
Aqueous solution is eluted, and compound shown in formula (I) is obtained.
Embodiment 4
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.The root of kirilow rhodiola medicinal material with
The weight ratio of water is 1:2.
Step 2, water extract step 1 obtained utilizes XB-C18Column carry out reversed-phase column chromatography separation, with 5v/v%~
The acetonitrile solution of 80v/v% carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/
The isolated component of v%~50v/v% aqueous solutions of organic solvent；
Step 3, the component that step 2 obtains is subjected to mesolow and prepares chromatographic separation and purification, with 8v/v%~30v/v%'s
Methanol aqueous solution is eluted, and compound shown in formula (I) is obtained.
Embodiment 5
The preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is mixed with water and carries out refluxing extraction, obtain water extract.The root of kirilow rhodiola medicinal material with
The weight ratio of water is 1:25.
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation using XB-Phenyl column, with 5v/v%
The acetonitrile solution of~80v/v% carries out gradient elution, and the flow velocity of gradient elution is 5mL/min~100mL/min；Collect 15v/
The isolated component of v%~50v/v% aqueous solutions of organic solvent；
Step 3, component step 2 obtained carries out high performance liquid chromatography separation purifying, with the second of 8v/v%~30v/v%
Nitrile aqueous solution is eluted, and compound shown in formula (I) is obtained.
Embodiment 6
Structural Identification is carried out to the compound that above-described embodiment 1 obtains, as a result referring to FIG. 1 to FIG. 7, wherein Fig. 1 is this
The ESI-MS figure of compound shown in the formula (I) provided is invented, Fig. 2 is the nuclear-magnetism hydrogen of compound shown in formula provided by the invention (I)
Spectrogram, Fig. 3 are the nuclear-magnetism carbon spectrogram of compound shown in formula provided by the invention (I), and Fig. 4 is shown in formula provided by the invention (I)
The HSQC of compound schemes, and Fig. 5 is the HMBC figure of compound shown in formula provided by the invention (I), and Fig. 6 is formula provided by the invention
(I) HSQC-TOCSY of compound shown in schemes, and Fig. 7 is compound shown in formula provided by the invention (I)1H-1HCOSY figure.
Specifically, compound is white powder, it can learn that m/z is 487.1455 [M-H]-by the mass spectral analysis of Fig. 1
(calculated value 487.1457), and then determine that compound molecule formula is C21H28O13。
Characteristic peak in nucleus magnetic hydrogen spectrum figure according to fig. 21H NMR δ 7.56 (2H, d, J=8.8Hz), 7.12 (2H, d, J=
It 8.8Hz), is 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=
It 16.0Hz), is 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 pyranoid form sugar.In conjunction with characteristic peak in Fig. 3 nuclear-magnetism carbon spectrogram13C NMR shows 21 carbon letters
Number, wherein having 9 is sp2The carbon signal of hydridization, δ 170.9,160.7,145.8,130.8 (× 2), 130.1,118.0 (× 2),
117.8, prompting the compound parent nucleus is p-Coumaric Acid；Remaining 12 are the carbon signal on 2 sugar, wherein there are two end group carbon to believe
Number δ 101.4,105.3.Ownership is carried out to part carbon signal by hsqc spectrum and observes that the sub- δ 5.04 of matrix is related to δ 101.4, δ
4.61 is related to δ 105.3.By HSQC, HMBC, HMQC-TOCSY,1H-1HCOSY is determined as two glucose.In HMBC spectrum,
Wherein δ 5.04 is related to δ 160.7 (C-4), and δ 4.61 is related to δ 87.6 (C-3 '), so determining compound provided by the invention
For p-Coumaric Acid -4-O- β-D- glucopyranose-(1 → 3)-O- β-D- glucopyranoside, English name p-
Coumaric acid-4-O- β-D-glucopyranosyl- (1 → 3)-O- β-D-glucopyran oside, table 1 are this hair
The nuclear magnetic data of compound shown in the formula (I) of bright offer.Its structure is as shown in Figure 8.
The nuclear magnetic data of compound shown in 1 formula provided by the invention (I) of table
Note：Test condition is deuterated methanol,1H NMR 400MHz,13C NMR 100MHz。
The anti-oxidant experiment of embodiment 7
Using DPPH free radical to p-coumaric acid-4-O- β-D-glucopyranosyl- (1 prepared by the present invention
→ 3) antioxidation activity in vitro of-O- β-D-glucopyranoside is evaluated, and it is new that 2mL is added in several 5mL centrifuge tubes
The 0.05mmol/L DPPH ethanol solution of fresh configuration is added each 300 μ L's of various concentration solution to be measured prepared with dehydrated alcohol
Solution shakes up, and is protected from light stands 30min at room temperature, and acquired solution is at 517nm after measuring the solution processing to be measured of each concentration respectively
Absorbance (Ax) value；
Its absorbance (Ax) value at 517nm is measured using dehydrated alcohol as reference；
Replacing solution to be measured that centrifuge tube is added with 300 μ L dehydrated alcohols (inside has the 0.05mmol/L of the fresh configuration of 2mL
DPPH ethanol solution) it is used as blank control, measure absorbance (A0) value；
It is mixed using solution to be measured with 2mL dehydrated alcohol as sample controls, is successively made into 1,0.5,0.4,0.2,0.1mg/
The solution of mL measures its absorbance (Ax) value, to eliminate the color of sample itself；
Using vitamin C as positive control.VC takes water as a solvent, be successively made into 1,0.5,0.4,0.2,0.1mg/mL it is molten
Liquid, measures its resistance to oxidation, and experiment condition is identical as sample.
DPPH clearance rate=[1- (As-Ax)/A0] × 100%；
It selects IC50 value to remove the testing index of DPPH ability for extract, establishes sample concentration and free radical scavenging activity returns
Return equation, calculates when clearance rate is 50%, sample concentration is IC50.After the extract of certain mass concentration is added,
DPPH Free Radical Signal obviously weakens, and absorbance value reduces with the increase of drug quality concentration, and clearance rate is with mass concentration
Increase and improve, illustrate that extract has a significant scavenging effect to DPPH free radical, and be in apparent amount-result relation.With clear
Except rate is fitted regression equation, compound y=0.8303x+0.1761, R to drug quality concentration2=0.9981IC50=
0.39mg·mL-1；Comparison medicine vitamin C y=0.395x+0.468, R2=0.9996, IC50=0.081mgmL-1。
The result shows that p-coumaric acid-4-O- β-D-glucopyranosyl- (1 → 3)-O- prepared by the present invention
The antioxidant activity of β-D-glucopyranoside is similar to vitamin C.As can be seen from the above embodiments, provided by the inventionization
Closing object has good antioxidant activity.
Above embodiments are only exemplary embodiment of the present invention, are not used in the limitation present invention, protection scope of the present invention
It is defined by the claims.Those skilled in the art can within the spirit and scope of the present invention make respectively the present invention
Kind modification or equivalent replacement, this modification or equivalent replacement also should be regarded as being within the scope of the present invention.
Claims (9)
1. a kind of phytochemical, which is characterized in that have structural formula shown in formula (I)；
2. a kind of preparation method of phytochemical, includes the following steps：
Step 1, root of kirilow rhodiola medicinal material is extracted with water, obtains water extract；
Step 2, water extract step 1 obtained carries out reversed-phase column chromatography separation, with the organic solvent of 5v/v%~80v/v%
Aqueous solution carries out gradient elution, collects the isolated component of 15v/v%~50v/v% aqueous solutions of organic solvent；It is described organic
Solvent is methanol, ethyl alcohol or acetonitrile；
Step 3, component step 2 obtained carries out chromatographic separation and purification, with the aqueous solutions of organic solvent of 8v/v%~30v/v%
It is eluted, obtains the compound as shown in following formula (I)；The organic solvent is methanol, ethyl alcohol or acetonitrile；
3. the preparation method of phytochemical according to claim 2, which is characterized in that the step 1 is specially：It will
Root of kirilow rhodiola medicinal material is mixed with water carries out refluxing extraction, obtains water extract.
4. the preparation method of phytochemical according to claim 3, which is characterized in that the root of kirilow rhodiola medicinal material and water
Weight ratio be 1:2~25.
5. according to the preparation method of the described in any item phytochemicals of claim 2-4, which is characterized in that the step 2
In, the flow velocity of gradient elution is 5mL/min~100mL/min.
6. the preparation method of phytochemical according to claim 5, which is characterized in that in the step 2, described point
From using XB-C18Column, XB-Phenyl column or XB-C8Column.
7. the preparation method of phytochemical according to claim 2, which is characterized in that in the step 3, the color
Spectrum, which isolates and purifies, prepares chromatographic isolation or normal pressure pillar layer separation for high performance liquid chromatography separation, mesolow.
8. phytochemical described in a kind of claim 1 is preparing the application in anti-oxidation medicine.
9. a kind of anti-oxidation medicine includes phytochemical described in claim 1.
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| 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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