CN103954700A - Method used for procyanidin content detection and identification - Google Patents
Method used for procyanidin content detection and identification Download PDFInfo
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Abstract
The invention discloses a method used for procyanidin content detection and identification, relates to a method used for detecting content of procyanidin in natural substances, health food, and medicines, and belongs to the field of organic chemistry. The method is characterized in that: analytically pure methanol is taken as a solvent; samples is mixed with analytically pure methanol, an obtained mixture is subjected to ultrasonic treatment at 40KHz for 20min, and is subjected to centrifugation at 4000r/min, and then a supernatant is collected so as to prepare a sample solution. Beneficial effects of the method are that: common experiment equipment and materials are used in the detection processes, and method popularization and application are convenient; sample pretreatment of the content detection part is simple, procyanidin B2 is taken as a reference substance, detection results are accurate, and result difference caused by difference of reference substances is avoided; reliable HPLC method is adopted for the product identification part, characteristic spectrums of different procyanidin products from different sources are established, identification on the sources can be realized effectively, and method specificity is high.
Description
Technical field
The present invention relates to a kind of detection method for natural materials, medicine procyanidin content, belong to organic chemistry filed, specifically a kind of mensuration procyanidin content and mirror method for distinguishing.
Background technology
Procyanidin (Proanthocyanidins), also be called condensed tannin (condensed tannins) or PCA, a kind ofly by several catechin compounds, to be polymerized, the plant polyphenol compounds with flavan-3-alcohol structure, be present in nature various plants, in the plants such as ginkgo leaf, grape pip, cowberry, pine bark, lotus pod, rose, all contain procyanidin.Research shows that procyanidin not only has very strong antioxidation activity; also there is good antitumor activity, Efficacy of Protecting Vascular Endothelial, adjusting blood pressure function, anti-inflammatory and irritated function simultaneously; be the effective constituent of several functions food, the various procyanidin of therefore extracting from plant are in recent years widely used in all kinds of health foods.
Because procyanidin is the element of the first species and complicated compound thereof, lack again the contrast that business can be used simultaneously, therefore, the content assaying method of procyanidin mainly contains spectrophotometric method, high performance liquid chromatography at present; Discrimination method mainly contains thin-layered chromatography, high performance liquid chromatography.
The ultimate principle of spectrophotometric method is to utilize procyanidin to be degraded under the condition of mineral acid existence and heating, produces red cyanidin, at 546nm place, has absorption maximum, measures procyanidin compounds.The method is representative is that the < < health food of 2007 editions is evaluated and technical manual > >.Though spectrophotometric method can record procyanidin total amount, in method, stipulate that procyanidin reference substance is too general, should not buy, and the method can not be differentiated procyanidin source.
The ultimate principle of HPLC is to utilize pre-treatment that procyanidin is degraded into anthocyanidin or sample after pre-treatment, and recycling HPLC chromatographic column is separated by the kinds of ingredients in procyanidin, more quantitative with standard items.Though the former can measure procyanidin content, can not differentiate the product of separate sources; The latter is due to the composition more complicated of procyanidin, and selected standard items are different, and result is just different, so the method is difficult to the procyanidin of accurate quantitative analysis overwhelming majority product.That the former is representative is the mensuration > > of PCA in GB/T22244-2008 < < health food; That the latter is representative is American Pharmacopeia (USP35) < < grape pip procyanidin > >.
The ultimate principle of thin-layered chromatography is to utilize procyanidin constituents and other impurity component to fixedly phase ability is different, make in the mobile process that flows through mutually fixing phase, continuous generation Adsorption and desorption is attached, adsorb again, desorption again, thereby reach the object disconnected from each other of each composition, thereby recycle the object that suitable colour developing reaches discriminating.The specificity that the method is differentiated for procyanidin series products is poor, therefore can not effectively differentiate procyanidin source.That representative is American Pharmacopeia (USP35) < < grape pip procyanidin > >.Because the extract product price variance of separate sources procyanidin is large, all kinds of procyanidin products are most of low without unified examination criteria or examination criteria, particularly the discriminating of separate sources procyanidin report is very few, cause some illegal businessmans to be spiked in high price product with the procyanidin product of low price, adulterate, disrupt the market, and harm eater's health and safety.
At present the most frequently used assay method is all very long detection time, and the reaction time all, more than half an hour, can not be accomplished fast detecting, and because speed and accuracy are particular about in online detection, this several method all can not meet the demand of being convenient to method promotion and application at present.
Summary of the invention
The present invention, mainly for the deficiencies in the prior art, proposes a kind of mensuration procyanidin content and mirror method for distinguishing, and it can carry out at normal temperatures and pressures to the sample containing procyanidin, and required time is short and nontoxic, and testing result is accurate.
For achieving the above object, a kind of mensuration procyanidin content of the present invention and mirror method for distinguishing, its implementation is as follows:
1, sample solution preparation: take 50-100mg sample and be placed in 50mL volumetric flask, add 30mL methyl alcohol, with the ultrasonic processing of 40KHz 20min, let cool to room temperature, add methyl alcohol to scale, shake up, get supernatant after centrifugal with 4000r/min, i.e. sample solution;
2, the drafting of typical curve: precision takes procyanidin standard items B
2(>=99%) 10mg, be dissolved in 10mL methyl alcohol, draw respectively this solution 0mL, 0.1mL, 0.25mL, 0.5mL, 1.0mL, 1.5mL and be placed in tool plug conical flask, adopt the assay method identical with sample to survey absorbance, take concentration (mg/mL) as horizontal ordinate, absorbance be ordinate typical curve processed;
3, Specimen Determination: after normal butyl alcohol is mixed by the volume ratio of 95:5 with hydrochloric acid, take out 6mL and be placed in tool plug conical flask, add again 0.2mL ammonium ferric sulfate solution and 1mL sample solution, mix, put 98-100 ℃ of boiling water bath and reflux, accurately heat after 40min, put immediately in 2-10 ℃ of cold water after cooling 15min, in 546nm wavelength place, survey absorbance, with typical curve, calculate the content of procyanidin in sample.
A kind of mensuration procyanidin mirror method for distinguishing of the present invention, usings acetonitrile as Mobile Phase Additives, by gradient elution, realizes the discriminating of procyanidin sample, and concrete steps are as follows:
1. standard model solution preparation: take sample 200mg and be placed in 50mL volumetric flask, add and analyze pure methyl alcohol 40mL, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after filtering with microporous membrane;
2. solution preparation: take sample 200mg and be placed in 50mL volumetric flask, add and analyze pure methyl alcohol 40mL, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
3. chromatographic condition: chromatographic column: PRP-125cm * 4.6mm * 5 μ m,
Mobile phase A: analyze pure acetonitrile
Mobile phase B: 0.3% phosphate aqueous solution
| Time (min) | 0 | 45 | 65 | 66 | 85 |
| Mobile phase A | 10 | 20 | 60 | 10 | 10 |
| Mobile phase B | 90 | 80 | 40 | 90 | 90 |
Flow velocity: 1ml/min
Check wavelength: 278nm
Column temperature: room temperature
Sample size: 5 μ L.
Described miillpore filter aperture is 0.45 μ m.
4. HPLC discrimination ratio is:
Under above-mentioned chromatographic condition, after instrument stabilizer, sample introduction records chromatogram, duplicate spectrogram and standard model spectrogram.
Described procyanidin B
2as spectrophotometry procyanidin reference substance, described procyanidin B
2reference substance is provided by ChromaDex.
Described rigidity styrene-divinylbenzene copolymer microspheroidal filled column is procyanidin HPLC discriminating chromatographic column, and this chromatographic column is provided by Hamilton.
The concentration of described methyl alcohol is pure for analyzing.
A kind of method of measuring procyanidin content of the present invention, its beneficial effect is: the present invention is with analyzing pure methyl alcohol as solvent, sample is mixed in to the ultrasonic processing of 40KHz 20min with analyzing pure methyl alcohol, gets supernatant after centrifugal with 4000r/min, make sample solution.Its beneficial effect is: this testing process is used normal experiment equipment and material, is convenient to method promotion and application; The pre-treatment of assay sample segment is simple, determines procyanidin B
2as reference substance, measurement result is accurate, has avoided due to the different result differences that cause of reference substance; Product differentiates that part has adopted reliable HPLC method, has set up the feature spectrogram of separate sources procyanidin series products, can effectively differentiate its source, and method specificity is strong.
Accompanying drawing explanation
Fig. 1 is mossberry extract standard model HPLC chromatogram;
Fig. 2 is grape seed extract standard model HPLC chromatogram;
Fig. 3 is peanut coat extract standard model HPLC chromatogram.
Embodiment
Following examples are that the present invention further goes out to set forth.
Embodiment 1
1, sample solution preparation: take mossberry extract sample 50mg sample and be placed in 50mL volumetric flask, add 30mL to analyze pure methyl alcohol, with the ultrasonic processing of 40KHz 20min, let cool to room temperature, add and analyze pure methyl alcohol to scale, shake up, after centrifugal with 4000r/min, get supernatant, i.e. sample solution;
2, the drafting of typical curve: precision takes procyanidin standard items B
2(>=99%) 10mg, being dissolved in 10mL analyzes in pure methyl alcohol, draw respectively this solution 0mL, 0.1mL, 0.25mL, 0.5mL, 1.0mL, 1.5mL and be placed in tool plug conical flask, adopt the assay method identical with sample to survey absorbance, take concentration (mg/mL) as horizontal ordinate, absorbance be ordinate typical curve processed;
3, Specimen Determination: after normal butyl alcohol is mixed by the volume ratio of 95:5 with hydrochloric acid, take out 6mL and be placed in tool plug conical flask, add again 0.2mL ammonium ferric sulfate solution and 1mL sample solution, mix, put 100 ℃ of boiling water baths and reflux, accurately heat after 40min, put immediately in 2 ℃ of cold water after cooling 15min, in 546nm wavelength place, survey absorbance, with typical curve, calculate the content of procyanidin in sample;
4, HPLC differentiates:
1. chromatographic condition: chromatographic column: PRP-125cm * 4.6mm * 5 μ m
Mobile phase A: analyze pure acetonitrile
Mobile phase B: 0.3% phosphate aqueous solution
| Time (min) | 0 | 45 | 65 | 66 | 85 |
| Mobile phase A | 10 | 20 | 60 | 10 | 10 |
| Mobile phase B | 90 | 80 | 40 | 90 | 90 |
Flow velocity: 1ml/min
Check wavelength: 278nm
Column temperature: room temperature
Sample size: 5 μ L
2. solution preparation: take the about 200mg of mossberry extract sample and be placed in 50mL volumetric flask, add and analyze pure methyl alcohol 40mL, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
3. standard model solution preparation: take the about 200mg of mossberry extract standard model and be placed in 50mL volumetric flask, add the about 40mL of methyl alcohol, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
5, HPLC discrimination ratio is:
Under above-mentioned chromatographic condition, after instrument stabilizer, sample introduction records chromatogram, duplicate spectrogram and standard model spectrogram.
Embodiment 2
1, sample solution preparation: take grape seed extract sample 50mg sample and be placed in 50mL volumetric flask, add 30mL to analyze pure methyl alcohol, with the ultrasonic processing of 40KHz 20min, let cool to room temperature, add and analyze pure methyl alcohol to scale, shake up, after centrifugal with 4000r/min, get supernatant, i.e. sample solution;
2, the drafting of typical curve: precision takes procyanidin standard items B
2(>=99%) 10mg, being dissolved in 10mL analyzes in pure methyl alcohol, draw respectively this solution 0mL, 0.1mL, 0.25mL, 0.5mL, 1.0mL, 1.5mL and be placed in tool plug conical flask, adopt the assay method identical with sample to survey absorbance, take concentration (mg/mL) as horizontal ordinate, absorbance be ordinate typical curve processed;
3, Specimen Determination: after normal butyl alcohol is mixed by the volume ratio of 95:5 with hydrochloric acid, take out 6mL and be placed in tool plug conical flask, add again 0.2mL ammonium ferric sulfate solution and 1mL sample solution, mix, put 100 ℃ of boiling water baths and reflux, accurately heat after 40min, put immediately in 10 ℃ of cold water after cooling 15 minutes, in 546nm wavelength place, survey absorbance, with typical curve, calculate the content of procyanidin in sample;
4, HPLC differentiates:
1. chromatographic condition: chromatographic column: PRP-125cm * 4.6mm * 5 μ m
Mobile phase A: analyze pure acetonitrile
Mobile phase B: 0.3% phosphate aqueous solution
| Time (min) | 0 | 45 | 65 | 66 | 85 |
| Mobile phase A | 10 | 20 | 60 | 10 | 10 |
| Mobile phase B | 90 | 80 | 40 | 90 | 90 |
Flow velocity: 1ml/min
Check wavelength: 278nm
Column temperature: room temperature
Sample size: 5 μ L
2. solution preparation: take the about 200mg of grape seed extract sample and be placed in 50mL volumetric flask, add and analyze the about 40mL of pure methyl alcohol, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
3. standard model solution preparation: take the about 200mg of grape seed extract standard model and be placed in 50mL volumetric flask, add the about 40mL of methyl alcohol, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
5, HPLC discrimination ratio is with embodiment 1.
Embodiment 3
1, sample solution preparation: take peanut coat extract sample 100mg sample and be placed in 50mL volumetric flask, add 30mL to analyze pure methyl alcohol, with the ultrasonic processing of 40KHz 20min, let cool to room temperature, add and analyze pure methyl alcohol to scale, shake up, after centrifugal with 4000r/min, get supernatant, i.e. sample solution;
2, the drafting of typical curve: precision takes procyanidin standard items B
2(>=99%) 10mg, being dissolved in 10mL analyzes in pure methyl alcohol, draw respectively this solution 0mL, 0.1mL, 0.25mL, 0.5mL, 1.0mL, 1.5mL and be placed in tool plug conical flask, adopt the assay method identical with sample to survey absorbance, take concentration (mg/mL) as horizontal ordinate, absorbance be ordinate typical curve processed;
3, Specimen Determination: after normal butyl alcohol is mixed by the volume ratio of 95:5 with hydrochloric acid, take out 6mL and be placed in tool plug conical flask, add again 0.2mL ammonium ferric sulfate solution and 1mL sample solution, mix, put 100 ℃ of boiling water baths and reflux, accurately heat after 40min, put immediately in 10 ℃ of cold water after cooling 15min, in 546nm wavelength place, survey absorbance, with typical curve, calculate the content of procyanidin in sample;
4, HPLC differentiates:
1. chromatographic condition: chromatographic column: PRP-125cm * 4.6mm * 5 μ m
Mobile phase A: analyze pure acetonitrile
Mobile phase B: 0.3% phosphate aqueous solution
| Time (min) | 0 | 45 | 65 | 66 | 85 |
| Mobile phase A | 10 | 20 | 60 | 10 | 10 |
| Mobile phase B | 90 | 80 | 40 | 90 | 90 |
Flow velocity: 1ml/min
Check wavelength: 278nm
Column temperature: room temperature
Sample size: 5 μ L
2. solution preparation: take the about 200mg of peanut coat extract sample and be placed in 50mL volumetric flask, add and analyze the about 40mL of pure methyl alcohol, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
3. standard model solution preparation: take the about 200mg of peanut coat extract standard model and be placed in 50mL volumetric flask, add the about 40mL of methyl alcohol, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
5, HPLC discrimination ratio is with embodiment 1.
The foregoing is only preferred embodiment of the present invention, in order to limit the present invention, within the spirit and principles in the present invention not all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (3)
1. a method of measuring procyanidin content, is characterized in that:
(1) sample solution preparation: take 50-100mg sample and be placed in 50mL volumetric flask, add 30mL methyl alcohol, with the ultrasonic processing of 40KHz 20min, let cool to room temperature, add methyl alcohol to scale, shake up, get supernatant after centrifugal with 4000r/min, i.e. sample solution;
(2) drafting of typical curve: precision takes procyanidin standard items B
2(>=99%) 10mg, be dissolved in 10mL methyl alcohol, draw respectively this solution 0mL, 0.1mL, 0.25mL, 0.5mL, 1.0mL, 1.5mL and be placed in tool plug conical flask, adopt the assay method identical with sample to survey absorbance, take concentration (mg/mL) as horizontal ordinate, absorbance be ordinate typical curve processed;
(3) Specimen Determination: after normal butyl alcohol is mixed by the volume ratio of 95:5 with hydrochloric acid, take out 6mL and be placed in tool plug container, add again 0.2mL ammonium ferric sulfate solution and 1mL sample solution, mix, put 98-100 ℃ of boiling water bath and reflux, accurately heat after 40min, put immediately in 2-10 ℃ of cold water after cooling 15min, in 546nm wavelength place, survey absorbance, with typical curve, calculate the content of procyanidin in sample.
2. utilize assay method described in claim 1 to differentiate a method for procyanidin in material, it is characterized in that: comprise the following steps: using acetonitrile as Mobile Phase Additives, by gradient elution, realize the discriminating of procyanidin sample, concrete steps are as follows:
1. standard model solution preparation: take sample 200mg and be placed in 50mL volumetric flask, add and analyze pure methyl alcohol 40mL, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after filtering with microporous membrane;
2. solution preparation: take sample 200mg and be placed in 50mL volumetric flask, add and analyze pure methyl alcohol 40mL, to be cooled to room temperature constant volume after 40KHz sonic oscillation 30min, measure with sample introduction after 0.45 μ m filtering with microporous membrane;
3. chromatographic condition: chromatographic column: PRP-125cm * 4.6mm * 5 μ m,
Mobile phase A: analyze pure acetonitrile
Mobile phase B: 0.3% phosphate aqueous solution
Flow velocity: 1ml/min
Check wavelength: 278nm
Column temperature: room temperature
Sample size: 5 μ L.
3. assay method is differentiated and be it is characterized in that the method for procyanidin in material: described miillpore filter aperture is 0.45 μ m as claimed in claim 2.
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| CN106841432A (en) * | 2017-01-10 | 2017-06-13 | 威海百合生物技术股份有限公司 | A kind of discriminating of Bilberry fruit P.E and its assay method of procyanidins content |
| CN107478758A (en) * | 2017-07-28 | 2017-12-15 | 大连大学 | The chemical composition standard finger-print and its construction method of cranberry and application |
| CN107843661A (en) * | 2015-12-30 | 2018-03-27 | 晨光生物科技集团股份有限公司 | Grape seed extract distinguishing method between true and false |
| CN108287202A (en) * | 2017-12-07 | 2018-07-17 | 佛山科学技术学院 | A method of detection honey vinegar black soya bean procyanidins |
| CN109470649A (en) * | 2018-12-24 | 2019-03-15 | 晨光生物科技集团股份有限公司 | A kind of near infrared detection method of Proanthocyanidins from Grape Seeds content |
| CN112114071A (en) * | 2020-09-21 | 2020-12-22 | 南京泛成生物科技有限公司 | Method for identifying vaccinium myrtillus extract and vaccinium vitis-idaea extract and determining proportion of mixture of vaccinium myrtillus extract and vaccinium vitis-idaea extract |
| CN113156036A (en) * | 2021-05-25 | 2021-07-23 | 浙江大学 | Method for analyzing proanthocyanidin structure by combining hydrophilic effect and reversed phase liquid chromatography |
| CN117929053A (en) * | 2024-01-29 | 2024-04-26 | 广东省农业科学院茶叶研究所 | Method for rapidly detecting relative content of small She Ziya tea anthocyanin |
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Cited By (12)
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| CN107843661A (en) * | 2015-12-30 | 2018-03-27 | 晨光生物科技集团股份有限公司 | Grape seed extract distinguishing method between true and false |
| CN107843661B (en) * | 2015-12-30 | 2023-02-24 | 晨光生物科技集团股份有限公司 | Method for identifying authenticity of grape seed extract |
| CN106841432A (en) * | 2017-01-10 | 2017-06-13 | 威海百合生物技术股份有限公司 | A kind of discriminating of Bilberry fruit P.E and its assay method of procyanidins content |
| CN107478758A (en) * | 2017-07-28 | 2017-12-15 | 大连大学 | The chemical composition standard finger-print and its construction method of cranberry and application |
| CN108287202A (en) * | 2017-12-07 | 2018-07-17 | 佛山科学技术学院 | A method of detection honey vinegar black soya bean procyanidins |
| CN109470649A (en) * | 2018-12-24 | 2019-03-15 | 晨光生物科技集团股份有限公司 | A kind of near infrared detection method of Proanthocyanidins from Grape Seeds content |
| CN109470649B (en) * | 2018-12-24 | 2021-05-11 | 晨光生物科技集团股份有限公司 | Near-infrared detection method for content of procyanidine in grape seeds |
| CN112114071A (en) * | 2020-09-21 | 2020-12-22 | 南京泛成生物科技有限公司 | Method for identifying vaccinium myrtillus extract and vaccinium vitis-idaea extract and determining proportion of mixture of vaccinium myrtillus extract and vaccinium vitis-idaea extract |
| CN113156036A (en) * | 2021-05-25 | 2021-07-23 | 浙江大学 | Method for analyzing proanthocyanidin structure by combining hydrophilic effect and reversed phase liquid chromatography |
| CN113156036B (en) * | 2021-05-25 | 2022-08-05 | 浙江大学 | Method for analyzing proanthocyanidin structure by combining hydrophilic effect and reversed phase liquid chromatography |
| CN117929053A (en) * | 2024-01-29 | 2024-04-26 | 广东省农业科学院茶叶研究所 | Method for rapidly detecting relative content of small She Ziya tea anthocyanin |
| CN117929053B (en) * | 2024-01-29 | 2024-08-09 | 广东省农业科学院茶叶研究所 | Method for rapidly detecting relative content of small She Ziya tea anthocyanin |
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Application publication date: 20140730 |