CN103655802A - Method for extracting antioxidant active component from rose leaf - Google Patents
Method for extracting antioxidant active component from rose leaf Download PDFInfo
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Abstract
The invention discloses a method for extracting antioxidant active components from rose leaves. The method comprises the following steps: (1) drying fresh rose leaves in the sun, crushing and sieving the rose leaves to obtain rose leaf granules; (2) extracting the rose leaf granules with an extraction solvent to obtain an extract; (3) centrifuging the extract to obtain a supernatant and concentrating the supernatant to obtain a concentrated liquid; (4) extracting the concentrated liquid sequentially with ethyl ether, ethyl acetate and water saturated normal butanol solution to obtain an ethyl ether extract, an ethyl acetate extract, a normal butanol extract and a water extract respectively, then concentrating the extracts respectively to obtain an ethyl ether extractive, an ethyl acetate extractive, a normal butanol extractive and a water extractive, and respectively labeling the extractives as Fa, Fb, Fc and Fd, so as to obtain the antioxidant components extracted from rose leaves. The method for screening antioxidant active components provided by the invention employs products from separation of a free radical solution from a liquid chromatography column for online reaction, and the separation and screening are carried out continuously, so as to quickly detect the antioxidant active components.
Description
Technical field
The present invention relates to the extracting method of anti-oxidation active substance in a kind of rose leaf.
Background technology
Human homergy or can produce free radical under various stressed conditions, excessive free radical can cause a series of diseases such as cancer, aging, diabetes, at this moment just needs supplemented with exogenous antioxidant to maintain interior free yl balance.Suppress the generation of free radical, make its quick quencher, repair its oxidative damage that human body is caused significant to health, the mensuration of finding natural anti-oxidation active component and antioxidant activity has become current focus.
Rose leaf is the leaf of Rosaceae Rosa machaka Flos Rosae Rugosae, and rose leaf contains a large amount of flavone compounds.This compounds can not only be removed the free radical of chain initiating stage in antioxidation reaction, and the free radical in can Direct Acquisition radical reaction chain, and blocking-up free chain reaction plays the dual function of prevention and chain rupture.At present, the existing extractive technique of extracting flavone compound from plant, but few for the report that extracts flavone compound from rose leaf both at home and abroad, only find the employing microwave extraction rose leaf flavone such as Jia Changhong, it is high that but the method requires instrument and equipment, and operating cost is high, and range of application is narrower, can not promote on a large scale, therefore also not have in the market standardized product to occur.
Aspect the mensuration of antioxidant activity, can adopt at present extract to carry out its antioxidant activity of Fast Measurement to ABTS free radical and DPPH radical scavenging activity, but, what these methods were measured is the gross activity of extract, but not one-component, and the method adopts colorimetry to measure, and is easily subject to the interference of substrate.
Summary of the invention
The extracting method that the object of this invention is to provide anti-oxidation active substance in a kind of rose leaf.
In a kind of rose leaf provided by the present invention, the extracting method of anti-oxidation active substance, comprises the steps:
(1) fresh rose leaf obtains rose leaf granule through drying by pulverizing and sieving;
(2) with rose leaf granule described in extraction solvent extraction, obtain extracting solution; Described extraction solvent is water or ethanol water;
(3) described extracting solution is through the centrifugal supernatant that obtains; Described supernatant is through the concentrated concentrated solution that obtains;
(4) described concentrated solution is extracted with ether, ethyl acetate and water saturated butanol solution successively, obtain respectively ether extraction liquid, acetic acid ethyl acetate extract, butanol extraction liquid and water extract, again respectively through concentrated ethereal extract, acetic acid ethyl ester extract, n-butyl alcohol extract and the water extract of obtaining, be labeled as respectively Fa, Fb, Fc and Fd, extract and obtained the antioxidant in rose leaf.
Described method also comprises the step that the antioxidant in described Fa, Fb, Fc and Fd is extracted:
Described Fa, Fb, Fc and Fd are carried out respectively to liquid chromatograph separated, detecting the liquid chromatogram I that is extracted thing under the condition that wavelength is 270nm and 350nm successively; Each component after separation is reacted with free-atom aqueous solution, then enters detector and detects, and obtains each extract and the reacted chemical composition collection of illustrative plates of described free-atom aqueous solution II detecting under the condition that wavelength is 270nm, 350nm and 747nm; Contrast the absworption peak under 270nm, 350nm and 747nm condition in described chemical composition collection of illustrative plates II, under identical retention time, when if the absworption peak under 270nm and 350nm condition is negative absorption peak under 747nm condition, component corresponding to this retention time is anti-oxidation active substance, and the component of collecting under this retention time is anti-oxidation active substance.
In above-mentioned method, in step (1), through described in the moisture content of rose leaf after drying can be 4%～8%;
The granularity of described rose leaf granule can be 20～80 orders.
In above-mentioned method, in step (2), in described ethanol water, the volume content of ethanol can be 10%～90%;
The temperature of described extraction can be 40～80 ℃, and the time of described extraction can be 60～80min;
The mass ratio of described extraction solvent and described rose leaf granule can be 5～30:1;
The number of times of described extraction can be 1～3 time.
In above-mentioned method, in step (3), described centrifugal rotating speed can be 3000～4800r/min, and the described centrifugal time can be 5～30min;
Described concentrated temperature can be 40～80 ℃;
The concentration of described concentrated solution can be 5～8 ° of Brix.
In above-mentioned method, in step (4), the volume ratio of described concentrated solution and described ether can be 1:2～3;
The volume ratio of ether raffinate and described ethyl acetate can be 1:2～3;
The volume ratio of ethyl acetate raffinate and described water-saturated n-butanol can be 1:2～3;
The number of times of described extraction can be 1～2 time;
Described concentrated temperature can be 40～70 ℃.
In above-mentioned method, described free-atom aqueous solution can be the aqueous solution of 2,2-azino-bis-(3-ethyl-benzothiazole-6-sulfonic acid) di-ammonium salts (ABTS);
Described free-atom aqueous solution can be 0.65～0.75 at the absorbance at 747nm place;
To be described free-atom aqueous solution react to produce with oxidation-resistant active ingredient in extract negative peak in described liquid chromatogram II fades, and absorbance reduces and causes.
In above-mentioned method, the temperature of described reaction can be 25～35 ℃.
In above-mentioned method, the condition of described liquid chromatograph separation is as follows: chromatographic column is Agilent Zorbax AQ post; Mobile phase A is water (containing the formic acid of mass concentration 2%) mutually, and Mobile phase B is acetonitrile mutually; Gradient elution program: 0～15min, 0%～10%B; 15～20min, 10%B; 20～30min, 10%～15%B; 30～40min, 15%B; 40～50min, 15%～20%B; 50～60min, 20%B; 60～65min, 20%～30%B.
In above-mentioned method, can detect the described anti-oxidation active substance filtering out by LC-MS.Then can to the antioxidant content identifying, carry out quantitatively by standard substance, the standard curve of the removing free radical ability that reference standard polyphenoils is set up, carries out Quantitative Comparison to the removing free radical ability of different antioxidant contents.
The present invention has following beneficial effect:
1, in method provided by the invention, rose leaf wide material sources, production technology is simple, and technological parameter is reasonable, and equipment investment cost is low, has higher economic results in society and wide industrial prospect.
2, anti-oxidation active substance screening technique provided by the invention, can solve the oxidation resistance that common method can only be measured total extract, can not measure the deficiency of the oxidation resistance of monomer.
3, anti-oxidation active substance screening technique provided by the invention adopts free-atom aqueous solution afterproduct separated with liquid-phase chromatographic column to react online, and separation screening carries out continuously, can detect fast and have oxidation-resistant active ingredient.
Accompanying drawing explanation
Fig. 1 is the process chart of method of the present invention.
Fig. 2 is the flow chart of the method for online screening antioxidant content (step (6)) in the inventive method.
Fig. 3 is the comparison diagram of the liquid chromatograph of ether extraction liquid in embodiment 1.
Fig. 4 is the comparison diagram of liquid chromatograph in acetic acid ethyl acetate extract in embodiment 1.
Fig. 5 is the comparison diagram of liquid chromatograph in butanol extraction liquid in embodiment 1.
Fig. 6 is the comparison diagram of liquid chromatograph in water extract in embodiment 1.
The specific embodiment
The experimental technique using in following embodiment if no special instructions, is conventional method.
In following embodiment, material used, reagent etc., if no special instructions, all can obtain from commercial channels.
ABTS free-atom aqueous solution preparation: the ABTS(Sigma company of getting 7mmol/L, Shanghai) aqueous solution mixes with the potassium persulfate solution of 2.45mmol/L, more than lucifuge reaction 12h, before experiment, with methanol, ABTS storing solution being diluted to 747nm place absorbance is 0.65～0.75.
Embodiment 1,
After fresh rose leaf is dried (its water content is 5%), pulverized 20 mesh sieves and obtained rose leaf granule.Take 50g rose leaf granule and add after triangular flask, add 500g deionized water, at 70 ℃, extract 3 times, extract 60min at every turn, merge the extracting solution obtaining.Extracting solution after merging is obtained to 1.5 ° of Brix supernatant after the centrifugal 15min of 4500r/min, and 60 ℃ of concentrating under reduced pressure, obtain 6 ° of Brix concentrated solutions.This concentrated solution is added to ether, ethyl acetate and water-saturated n-butanol solution successively with 1:2 volume ratio, all extract 2 times and obtain successively ether extraction liquid, acetic acid ethyl acetate extract, butanol extraction liquid and water extract.Above-mentioned each extract is evaporated to respectively dry at 50 ℃, obtain ethereal extract (Fa) 2.36g, acetic acid ethyl ester extract (Fb) 3.85g, n-butyl alcohol extract (Fc) 3.94g, and water extract (Fd) 2.97g, dissolve respectively and be settled to 200mL with methanol solution, cross respectively 0.45 μ m film, separated through high performance liquid chromatography, separation condition is: Agilent Zorbax AQ post (250mm * 4.6mm i.d., 5 μ m); Mobile phase A is water (containing concentration 2% formic acid) mutually, and Mobile phase B is acetonitrile mutually; Gradient elution program: 0～15min, 0%～10%B; 15～20min, 10%B; 20～30min, 10%～15%B; 30～40min, 15%B; 40～50min, 15%～20%B; 50～60min, 20%B; 60～65min, 20%～30%B.Sample size 10 μ L; Flow velocity is 0.8ml/min; 25 ℃ of column temperatures; Detect wavelength 270nm and 356nm.Device detects after testing, obtains the liquid chromatogram of four kinds of extracts, is denoted as composition collection of illustrative plates, and collects separated each component obtaining.
The ABTS free-atom aqueous solution preparing is pumped into past column reaction system with 0.5mL/min flow velocity, and thermostat temperature is 30 ℃, and ABTS flow of solution enters detector after response system, after 747nm place absorbance balance, and baseline zeroing.Press above-mentioned condition by four kinds of extract solutions difference sample introductions, each component and ABTS free-atom aqueous solution that liquid chromatograph separation obtains enter detector after past column reaction system response, record the retention time under 270nm, 356nm and 747nm, obtain respectively corresponding collection of illustrative plates, be denoted as the rear collection of illustrative plates of reaction; Absworption peak under 270nm, 350nm and 747nm condition in collection of illustrative plates after contrast reaction, under identical retention time, when if the absworption peak under 270nm and 350nm condition is negative absorption peak under 747nm condition, component corresponding to this retention time is anti-oxidation active substance, and the component of collecting under this retention time obtains anti-oxidation active substance.
Wherein, the comparison diagram of ethereal extract (Fa) as shown in Figure 3, the comparison diagram of acetic acid ethyl ester extract (Fb) as shown in Figure 4, the comparison diagram of n-butyl alcohol extract (Fc) as shown in Figure 5, the comparison diagram of water extract (Fd) as shown in Figure 6, filters out the component with negative peak and is anti-oxidation active substance.
To the anti-oxidation active substance filtering out in each extract, adopt LC-MS technology to carry out qualitative analysis.
In conjunction with the standard diagram of each antioxidant, can learn, in ethereal extract, altogether detect 10 kinds of antioxidant such as Quercetin, Quercetin 3-β-D-Glucose glycoside, apigenin-8-C-glucoside; In acetic acid ethyl ester extract, detect 14 kinds of antioxidant such as catechin, rutin; In n-butyl alcohol extract, detect 15 kinds of antioxidant such as chlorogenic acid; In water extract, detect 11 kinds of antioxidant such as middle quininic acid.
Embodiment 2,
After fresh rose leaf is dried (its water content is 6%), pulverized 20 mesh sieves and obtained rose leaf granule.Take 50g rose leaf granule and add after triangular flask, add the ethanol water of 1000g ethanol volumn concentration 50%, at 70 ℃, extract 2 times, extract 60min at every turn, merge the extracting solution that obtains 1.2 ° of Brix.This extracting solution is obtained to supernatant after the centrifugal 15min of 4500r/min, then at 55 ℃ concentrating under reduced pressure, obtain the concentrated solution of 6 ° of Brix.This concentrated solution is added to ether, ethyl acetate and water-saturated n-butanol solution successively with 1:3 volume ratio, extract and obtain successively ether extraction liquid, acetic acid ethyl acetate extract, butanol extraction liquid and water extract 1 time.Each extract is evaporated to respectively dry at 45 ℃, obtain ethereal extract (Fa) 2.12g, acetic acid ethyl ester extract (Fb) 3.89g, n-butyl alcohol extract (Fc) 3.57g, and water extract (Fd) 2.84g, dissolve respectively and be settled to 200mL with methanol solution, cross respectively 0.45 μ m film, separated through high performance liquid chromatography, separation condition is: Agilent Zorbax AQ post (250mm * 4.6mm i.d., 5 μ m); Mobile phase A is water (containing concentration 2% formic acid) mutually, and Mobile phase B is acetonitrile mutually; Gradient elution program: 0～15min, 0%～10%B; 15～20min, 10%B; 20～30min, 10%～15%B; 30～40min, 15%B; 40～50min, 15%～20%B; 50～60min, 20%B; 60～65min, 20%～30%B.Sample size 10 μ L; Flow velocity is 0.8ml/min; 25 ℃ of column temperatures; Detect wavelength 270nm, 356nm.Device detects after testing, obtains the liquid chromatogram of four kinds of extracts, is denoted as composition collection of illustrative plates, and collects separated each component obtaining.
The ABTS free-atom aqueous solution preparing is pumped into past column reaction system with 0.7mL/min flow velocity, and thermostat temperature is 35 ℃, and ABTS flow of solution enters detector after response system, after 747nm place absorbance balance, and baseline zeroing.Press above-mentioned condition by four kinds of extract solutions difference sample introductions, each component and ABTS free-atom aqueous solution that liquid chromatograph separation obtains enter detector after past column reaction system response, record the retention time under 270nm, 356nm and 747nm, obtain respectively corresponding collection of illustrative plates, be denoted as the rear collection of illustrative plates of reaction; Absworption peak in the rear collection of illustrative plates of contrast reaction under 270nm, 350nm and 747nm condition, under identical retention time, when if the absworption peak under 270nm and 350nm condition is negative absorption peak under 747nm condition, component corresponding to this retention time is anti-oxidation active substance, and the component of collecting under this retention time obtains anti-oxidation active substance.
To the anti-oxidation active substance filtering out in each extract, adopt LC-MS technology to carry out qualitative analysis.
In conjunction with the standard diagram of each antioxidant, can learn, in ethereal extract, altogether detect 10 kinds of antioxidant such as Quercetin, Quercetin 3-β-D-Glucose glycoside, apigenin-8-C-glucoside; In acetic acid ethyl ester extract, detect 14 kinds of antioxidant such as catechin, rutin; In n-butyl alcohol extract, detect 15 kinds of antioxidant such as chlorogenic acid; In water extract, detect 11 kinds of antioxidant such as middle quininic acid.
Claims (9)
1. an extracting method for anti-oxidation active substance in rose leaf, comprises the steps:
(1) fresh rose leaf obtains rose leaf granule through drying by pulverizing and sieving;
(2) with rose leaf granule described in extraction solvent extraction, obtain extracting solution; Described extraction solvent is water or ethanol water;
(3) described extracting solution is through the centrifugal supernatant that obtains; Described supernatant is through the concentrated concentrated solution that obtains;
(4) described concentrated solution is extracted with ether, ethyl acetate and water saturated butanol solution successively, obtain respectively ether extraction liquid, acetic acid ethyl acetate extract, butanol extraction liquid and water extract, again respectively through concentrated ethereal extract, acetic acid ethyl ester extract, n-butyl alcohol extract and the water extract of obtaining, be labeled as respectively Fa, Fb, Fc and Fd, extract and obtained the anti-oxidation active substance in rose leaf.
2. extracting method according to claim 1, is characterized in that: described method also comprises the step that the antioxidant in described Fa, Fb, Fc and Fd is extracted:
Described Fa, Fb, Fc and Fd are carried out respectively to liquid chromatograph separated, detecting the liquid chromatogram I that is extracted thing under the condition that wavelength is 270nm and 350nm successively; Each component after separation is reacted with free-atom aqueous solution, then enters detector and detects, and obtains each extract and the reacted chemical composition collection of illustrative plates of described free-atom aqueous solution II detecting under the condition that wavelength is 270nm, 350nm and 747nm; Contrast the absworption peak under 270nm, 350nm and 747nm condition in described chemical composition collection of illustrative plates II, under identical retention time, when if the absworption peak under 270nm and 350nm condition is negative absorption peak under 747nm condition, component corresponding to this retention time is anti-oxidation active substance, and the component of collecting under this retention time is anti-oxidation active substance.
3. method according to claim 1 and 2, is characterized in that: in step (1), through described in the moisture content of rose leaf after drying be 4%～8%;
The granularity of described rose leaf granule is 20～80 orders.
4. according to the method described in any one in claim 1-3, it is characterized in that: in step (2), in described ethanol water, the volume content of ethanol is 10%～90%;
The temperature of described extraction is 40～80 ℃, and the time of described extraction is 60～80min;
The mass ratio of described extraction solvent and described rose leaf granule is 5～30:1;
The number of times of described extraction is 1～3 time.
5. according to the method described in any one in claim 1-4, it is characterized in that: in step (3), described centrifugal rotating speed is 3000～4800r/min, and the described centrifugal time is 5～30min;
Described concentrated temperature is 40～80 ℃;
The concentration of described concentrated solution is 5～8 ° of Brix.
6. according to the method described in any one in claim 1-5, it is characterized in that: in step (4), the volume ratio of described concentrated solution and described ether is 1:2～3;
The volume ratio of ether raffinate and described ethyl acetate is 1:2～3;
The volume ratio of ethyl acetate raffinate and described water-saturated n-butanol is 1:2～3;
The number of times of described extraction is 1～2 time;
Described concentrated temperature is 40～70 ℃.
7. according to the method described in any one in claim 2-6, it is characterized in that: described free-atom aqueous solution is the aqueous solution of 2,2-azino-bis-(3-ethyl-benzothiazole-6-sulfonic acid) di-ammonium salts;
The absorbance of described free-atom aqueous solution at 747nm place is 0.65～0.75.
8. according to the method described in any one in claim 2-7, it is characterized in that: the temperature of described reaction is 25～35 ℃.
9. according to the method described in any one in claim 1-8, it is characterized in that: the described anti-oxidation active substance going out by LC-MS evaluation and screening.
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| CN107019222A (en) * | 2017-04-13 | 2017-08-08 | 盐城工学院 | The extraction process of anti-oxidation active substance and the preparation technology of antioxidation activity particle |
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