CN102141519B - Method for detecting procyanidins content - Google Patents
Method for detecting procyanidins content Download PDFInfo
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Abstract
The invention provides a method for detecting the procyanidins content, comprising the following steps of sample treatment, chromogenic reagent preparation and sample detection. In the method, ethanol is used as a solvent, replacing methanol, and a dry powder sample is completely dissolved at higher temperature and under ultrasoud, thereby the disadvantage that the sample is difficult to completely dissolve in high-concentration ethanol is solved. With the regulation of the ethanol concentration of a semi-finished solution, the problems that tedious steps of needing to evaporate the semi-finished solution to dryness firstly and then dissolving the sample with the methanol, reducing degradation of procyanidins in the evaporating process and the like of the traditional vanillin-hydrochloric acid method are solved, detection which needs short time without toxicity and is suitable for carrying out in the production field in real time is carried out on a finished product, a semifinishs product or a raw material containing the procyanidins under normal temperature and pressure, a detection result is accurate, the detection is truly accurate, rapid and simple, and the production efficiency of the product is enhanced. Compared with the traditional method for detecting the procyanidins, the method for detecting the procyanidins content is more rapid, the operation is more simple, the repeatability of the result is good, and the accuracy is high.
Description
Technical field
The present invention relates to a kind of detection method for natural materials, medicine, health food, beverage and cosmetics procyanidin content.
Background technology
Procyanidin (Proanthocyanidins), also be called condensed tannin (condensed tannins), a kind ofly to be polymerized by several catechin compounds, plant polyphenol compounds with flavan-3-alcohol structure, be present in the nature various plants, all contain procyanidin in the plants such as ginkgo leaf, grape pip, cowberry, pine bark, lotus pod, rose.Confirm that after deliberation procyanidin has very strong anti-oxidant and radical scavenging activity, and cardiovascular and cerebrovascular is had preferably protective effect.
Because procyanidin is the element of the first species and complicated compound thereof, lack again simultaneously commercial available contrast, therefore, the content assaying method of procyanidin mostly is colourimetry at present, comprises acid butanols method, vanillin method, 4-di methyl amino cinnamaldehyde method, ammonium molybdate method, ammonium ceric sulfate, ferric salt-potassium ferricyanide etc.Acid butanols ratio juris is that procyanidin is transformed into the coloured anthocyanidin of tool under acid condition, thereby calculates the content of procyanidin by measuring absorbance; The vanillic aldehyde ratio juris is that vanillic aldehyde is transformed into cationic molecule under acid condition, and are combined and form coloured material in the phloroglucin of A ring or resorcinol nucleophilic site in the flavan-3-alcohol structure, utilize absorbance to calculate the content of procyanidin; 4-di methyl amino cinnamaldehyde ratio juris is similar to vanillin method, the 4-di methyl amino cinnamaldehyde is transformed into cationic molecule under acid condition, are combined and form coloured material in the phloroglucin of A ring or resorcinol nucleophilic site in the flavan-3-alcohol structure, utilize absorbance to calculate the content of procyanidin.And mostly additive method is to detect the method for polyphenol, contains the higher product of flavones ingredient for those, and the measured value of these methods can be significantly higher.But the acid butanols method that specificity is relatively high and vanillin method are when measuring the ginkgo procyanidin, and also exist obvious deficiency: acid butanols method is vulnerable to the impact of anthocyanidin and accessory substance, and result's repeatability and reliability are relatively poor; Although 4-di methyl amino cinnamaldehyde method is highly sensitive in vanillin method, because the absorption coefficient of monomer is apparently higher than polymeric absorption coefficient, so its measurement result is subject to the impact of monomer and obviously higher easily.
The most frequently used assay method is vanillin method at present, but the method for bibliographical information exists obvious deficiency equally, and method is various, and is also ununified so far.Vanillin-sulfuric acid method [Bao Junzhu, Chen Yuekun, Xu Guihua. measure the method for Proanthocyanidin from Grape-seed Extracts. research of agricultural science, 2005,26 (1): 43-45.] in testing process, can produce very large heat when adding sulfuric acid, so its measurement result is subject to the oxidative degradation of procyanidin and obviously on the low side; Initial vanillic aldehyde-salt acid system [Zhao Yi, Huang Yumei, Yang Yanping. the progress of grape seed procyanidine content assaying method. Gansu college of traditional Chinese medicine journal, 2006,23 (6): 43-46.], developer is the vanillic aldehyde methanol solution of 6mL 4% and the concentrated hydrochloric acid mixed solution of 3mL, lucifuge reaction 15 hours; By improvement [Chunyang LI, Xu Shiying, Wang Zhang. low concentration vanillic aldehyde-salt acid system is measured the research of procyanidin content in grape pip, the stalk. food industry science and technology, 2004,25 (6): 128-130.], the hydrochloric acid of employing 4% and 0.5% vanillic aldehyde methanol solution develop the color, 30 ℃ of control temperature of reaction, 30 minutes reaction time.But the reaction dissolvent of above-mentioned vanillin method is methyl alcohol, and toxicity is large, is used for very inconvenience of On-line Product production testing, needs to carry out under special laboratory environment; And this several method is all very long detection time, and the reaction time all more than half an hour, can not be accomplished fast detecting, because speed and accuracy are particular about in online detection, this several method all can not satisfy the demand of online detection at present.
Summary of the invention
Technical matters to be solved by this invention provides a kind of method that detects procyanidin content, and it can carry out at normal temperatures and pressures to the sample that contains procyanidin, and required time is short and nontoxic, and testing result is accurate.
For this reason, the present invention is by the following technical solutions:
1. sample preparation
Be dissolved in the ethanolic solution that mass percent is 60-95% after will containing the sample pretreatment of procyanidin.
2. developer preparation
Then hydrochloric acid and vanillic aldehyde are mixed composition chromogenic reaction liquid with the ethanol solution constant volume respectively, and the volume accounting of hydrochloric acid in chromogenic reaction liquid is 6-15%, and the quality accounting of vanillic aldehyde in chromogenic reaction liquid is 0.5-2%;
3. sample detection
With reaction under the procyanidin ethanolic solution that configures and chromogenic reaction liquid normal temperature 5-12 minute, then with the absorbance of spectrophotometric determination reactant liquor at 496nm place, calibration curve method calculating procyanidin content.
According to the different sample sources that contain procyanidin, sample pretreatment has diverse ways:
1. online production finished product or dry powder sample: be that the ethanol of 60-95% substitutes methyl alcohol in traditional vanillic aldehyde-salt acid system as the solvent of dissolution sample with mass percent, sample is at temperature 40-50.℃, assisting a ruler in governing a country dissolving with ultrasonic, the result has solved the problem that test sample can not be dissolved in high concentration ethanol fully; And with the solution of the methyl alcohol in the alternative traditional vanillic aldehyde of absolute ethyl alcohol-salt acid system as the developer configuration, solved with methyl alcohol and detected toxicity problem.
2. the semi-finished product solution during online production: the concentration of alcohol by adjusting semi-finished product solution is to 60-95%, having solved traditional vanillic aldehyde-salt acid system needs first the semi-finished product solution evaporate to dryness also to be used again the loaded down with trivial details step of methyl alcohol dissolution sample, greatly shortened the running time, reduced the degraded in evaporate to dryness process when procyanidin is used former detection method, accelerated reaction velocity, improve the accuracy that detects, solved the online difficult problem that detects of methyl alcohol.
On the basis of adopting technique scheme, the present invention also can adopt following further technical scheme:
Describedly contain the procyanidin sample to be dissolved in mass percent be 80% ethanolic solution, or the semi-finished product solution during with online production is adjusted concentration of alcohol to 80%.
The volume ratio of hydrochloric acid in chromogenic reaction liquid is 10%, and the quality accounting of described vanillic aldehyde in chromogenic reaction liquid is 1%.
Reaction time is 8 minutes, and temperature of reaction is normal temperature.
The described sample that contains procyanidin to be measured is ginkgo biloba p.e, grape seed extract, Pine Bark, Bilberry fruit P.E, Receptaculum nelumbinis extract, Flos Rosae Rugosae extract etc.
Owing to adopt technique scheme of the present invention, the present invention replaces methyl alcohol as solvent, at higher temperature and ultrasonic lower dissolving dry powder sample by the improvement to vanillin method with ethanol, make it to dissolve fully, solved sample and in high concentration ethanol, be difficult to consoluet shortcoming; By adjusting the concentration of alcohol of semi-finished product solution, solve the loaded down with trivial details step that traditional vanillic aldehyde-salt acid system need to be used to semi-finished product solution elder generation evaporate to dryness the methyl alcohol dissolution sample again simultaneously, reduced the problems such as degraded of procyanidin in the evaporate to dryness process.Can finished product, semi-manufacture or the raw material that contain procyanidin be carried out at normal temperatures and pressures, required time is short and nontoxic and be suitable for detecting in real time in the production scene, and testing result is accurate, really accomplishes accurately fast and conveniently, improves the production efficiency of product.The present invention is more convenient with respect to the method for before mensuration procyanidin, operation is more simple, result's good reproducibility, accuracy are high, is specially adapted to the Real-Time Monitoring of procyanidin content in the process of producing product.
Description of drawings
Fig. 1 is that concentration of alcohol is on the figure that affects of absorbance.
Fig. 2 is that concentration of hydrochloric acid is on the figure that affects of absorbance.
Fig. 3 is that vanillic aldehyde concentration is on the figure that affects of absorbance.
Fig. 4 is that the reaction time is on the figure that affects of absorbance.
Embodiment
Embodiment 1, the foundation of optimum response system
(1), replace methyl alcohol as the solvent of reaction system with ethanol, prepare developer: 10ml hydrochloric acid enters the 50ml volumetric flask, uses the absolute ethyl alcohol constant volume, makes developer A; The 1g vanillic aldehyde enters the 50ml volumetric flask, uses the anhydrous alcohol solution constant volume, makes developer B; Face the time spent, developer A and B were mixed in 1: 1 by volume.
When (2) sample prepares, determining of best concentration of alcohol: take by weighing the procyanidin contrast, use first anhydrous alcohol solution, again the procyanidin check sample is diluted with water to same concentration, the different ethanol concentration gradient is set: 50%, 60%, 70%, 80%, 90%, 95%, measure each sample absorbance (seeing Fig. 1) with the developer of step 1, determine when mass percent is 60-95% to be the concentration of alcohol of measuring procyanidin content in the production run, wherein 80% is the best of measuring procyanidin content in the production run; 60-95% is the concentration of alcohol that concentration of alcohol detects finished product Central Plains anthocyanidin content, wherein 95% concentration of alcohol for concentration of alcohol detection finished product Central Plains anthocyanidin content.Above number percent is mass percent.
(3) determining of reaction system maximum absorption wavelength: after the sample chromogenic reaction to 80% concentration of alcohol and 95% concentration of alcohol, carry out full wavelength scanner, determine that 496nm is maximum absorption wavelength.
(4) determining of the best concentration of hydrochloric acid of reaction system: vanillic aldehyde reaction final concentration is 1%, change the final concentration of reaction system hydrochloric acid: 1%, 2%, 4%, 6%, 8%, 10%, 12%, 15%, measure each sample absorbance (seeing Fig. 2) with the developer of step 1, determine that volume ratio 6-15% is the reacting salt acid concentration, wherein 10% is the best concentration of hydrochloric acid of reaction.
(5) determining of the best vanillic aldehyde concentration of reaction system: the hydrochloric acid reaction final concentration is 10%, change the final concentration of reaction system vanillic aldehyde: 0.25%, 0.5%, 1%, 1.5%, 2%, measure each sample absorbance (seeing Fig. 3) with the developer of step 1, determine that 0.5-2% is reaction vanillic aldehyde concentration, wherein 1% is the best vanillic aldehyde concentration of reaction.Above number percent is mass percent.
(6) the determining of reaction system optimum reacting time (seeing Fig. 4): the hydrochloric acid reaction final concentration is 10%, and vanillic aldehyde reaction final concentration is 1%, determines to be the reaction time in 5～12 minutes, and wherein 8 minutes is optimum reacting time.
The comparison of several method procyanidin content in measuring ginkgo biloba p.e commonly used of embodiment 2
(1) method set up of the present invention: take by weighing respectively 35.9,34.0,37.7,33.9,47.5, the 38.6mg ginkgo biloba p.e enters the 10ml volumetric flask, the ethanol with 80% is dissolved under 46 ℃ with constant volume behind the ultrasonic dissolution.With reaction under the absolute ethyl alcohol nitrite ion normal temperature that contains percent by volume 10% hydrochloric acid and mass percent 1% vanillic aldehyde 8 minutes, absorbance was detected at the 496nm place, detects with calibration curve method, and getting average procyanidin content is 8.34%, RSD=1.09%.
(2) hydrochloric acid-vanillin method in the document: take by weighing respectively 27.9,40.0,36.9,34.0, the 30.8mg ginkgo biloba p.e enters the 10ml volumetric flask, dissolves constant volume with methyl alcohol.With the methyl alcohol nitrite ion 30 degree reactions that contain percent by volume 4% hydrochloric acid and mass percent 1% vanillic aldehyde 30 minutes, absorbance was detected at the 500nm place, and getting average procyanidin content is 8.38%, RSD=1.79%.
(3) hydrochloric acid normal butyl alcohol method: accurately take by weighing the 10mg sample, with methyl alcohol dissolving and be settled to 100ml.During reaction, get the 1ml sample solution, the HCL/n-BuOH solution of 6ml 5%, 0.2ml 2% ammonium ferric sulfate solution, boiling water bath cooled off rapidly with cold water after 40 minutes, and the 546nm place measures absorbance.
This method measuring principle is that procyanidin is hydrolyzed to anthocyanidin, but should reaction can generate colourless accessory substance, so measurement result can be on the low side.Measured by this method and to obtain that procyanidin content is 7.43%, RSD=5.88% in the ginkgo biloba p.e.
(4) sulfuric acid-vanillin method: accurately take by weighing the 10mg sample, with methyl alcohol dissolving and be settled to 10ml.During reaction, get the 0.5ml sample solution, 2.5ml mass percent 3% vanillic aldehyde methanol solution, 2.5ml percent by volume 30% sulfuric acid, 30 ℃ of lucifuge reaction 20min, the 500nm place measures absorbance.
Measured by this method and to obtain that procyanidin content is 8.29%, RSD=3.16% in the ginkgo biloba p.e.
(5) 4-di methyl amino cinnamaldehyde method: accurately take by weighing the 25mg sample, with 70 ethanol dissolvings and be settled to 50ml.During reaction, get the 1ml sample solution, 3ml 4-di methyl amino cinnamaldehyde solution, reaction is 25 minutes under the normal temperature, and the 640nm place measures absorbance.
Measured by this method and to obtain that procyanidin content is 8.47%, RSD=2.11% in the ginkgo biloba p.e.
By comparing with method for distinguishing, method required time used herein is the shortest, and relative standard deviation is little as a result, and measurement result and other method are basically identical.And reagent that the present invention adopts is nontoxic reagent, can be used for the online detection of production.
The detection of procyanidin content in embodiment 3 ginkgo leaves
(1) take by weighing the 20g ginkgo leaf, pulverize, enter the 250ml round-bottomed flask, add 150ml 80 ethanol, 90 degree refluxing extraction 1 hour are filtered, and repeat to extract 2 times again, and merging filtrate gets the about 430ml of filtrate S1.Get 1ml filtrate, recording procyanidin content with described detection method provided by the invention is 0.148mg/ml, and minute is 10 minutes (minutes: the T.T. of calculating from being sampled to the result).
Other takes by weighing the 20g ginkgo leaf, pulverizes, and enters the 250ml round-bottomed flask, adds 150ml 80 ethanol, and 90 degree refluxing extraction 1 hour are filtered, and repeat to extract 2 times again, and merging filtrate gets the about 430ml of filtrate S2.Get 10ml filtrate, drying under reduced pressure adds the dissolving of 10ml methyl alcohol, and recording procyanidin content with the vanillin method of bibliographical information is 0.146mg/ml, and minute is 56 minutes.
The detection of procyanidin content in the embodiment 4 ginkgo biloba p.e production runes
(1) gets semi-manufacture ethanolic solution 200ml in online early stage in the ginkgo leaf leaching process, solution decompression is concentrated into without the alcohol flavor, is splined on the macroreticular resin of handling well, after the washing, with mass percent 70% ethanol elution, get the about 150ml of 70% alcohol elution S3.Get the 1ml sample, adjust concentration of alcohol to mass percent 90% with absolute ethyl alcohol, recording procyanidin content with described detection method provided by the invention is 0.206mg/ml, and minute is 11 minutes.
(2) get online 70% ethanol elution semi-manufacture 200ML in the ginkgo leaf leaching process, through drying under reduced pressure, get ginkgo biloba p.e 464mg, recording procyanidin with described detection method provided by the invention is 37.20mg, percentage by weight is 8.02%, the procyanidin yield is 0.186%, and minute is 10 minutes.
The detection of procyanidin content in the embodiment 5 grape seed extract production runes
(1) the grape pip raw material detects
Take by weighing the 10g grape pip, pulverize, enter the 250ml round-bottomed flask, add 100ml mass percent 50% ethanol, 90 degrees centigrade of refluxing extraction 1 hour are filtered, and repeat to extract 2 times again, and merging filtrate gets the about 280ml of filtrate.Get 1ml filtrate, recording procyanidin content with described detection method provided by the invention is 1.668mg/ml, and namely the procyanidin total amount is 467.04mg.
(2) the grape pip intermediate product detects
The filtrate decompression of getting in the grape pip leaching process is concentrated into without the alcohol flavor, is splined on the macroreticular resin of handling well, after the washing, with mass percent 70% ethanol elution, gets the about 150ml of 70% alcohol elution.Get the 1ml sample, recording procyanidin content with described detection method provided by the invention is 2.579mg/ml, and namely the procyanidin total amount is 386.85mg.
(3) grape seed extract detects
Get grape seed extract 787.69mg, recording the procyanidin total amount with described detection method provided by the invention is 382.17mg, and percentage by weight is 45.52%, and the procyanidin yield is 3.82%.
The detection of procyanidin content in the embodiment 6 Pine Bark production runes
(1) the pine bark raw material detects
Take by weighing the 10g pine bark, pulverize, enter the 250ml round-bottomed flask, add 100ml mass percent 50% ethanol, 90 degrees centigrade of refluxing extraction 1 hour are filtered, and repeat to extract 2 times again, and merging filtrate gets the about 280ml of filtrate.Get 1ml filtrate, recording procyanidin content with described detection method provided by the invention is 0.462mg/ml, and namely the procyanidin total amount is 129.36mg.
(2) the pine bark intermediate product detects
Filtrate decompression in the pine bark leaching process is concentrated into without the alcohol flavor, is splined on the macroreticular resin of handling well, after the washing, with mass percent 70% ethanol elution, get the about 150ml of 70% alcohol elution.Get the 1ml sample, recording procyanidin content with described detection method provided by the invention is 0.701mg/ml, and namely the procyanidin total amount is 105.15mg.
(3) Pine Bark detects
Get Pine Bark 487.69mg, recording the procyanidin total amount with described detection method provided by the invention is 102.33mg, and percentage by weight is 20.98%, and the procyanidin yield is 1.02%.
Claims (8)
1. online method that detects procyanidin content, it has adopted following steps its feature:
I. sample preparation
Be dissolved in the ethanolic solution that mass percent is 60-95% after will containing the sample pretreatment of procyanidin;
II. developer preparation
Then hydrochloric acid and vanillic aldehyde are mixed composition chromogenic reaction liquid with the ethanol solution constant volume respectively, and the volume accounting of hydrochloric acid in chromogenic reaction liquid is 6-15%, and the quality accounting of vanillic aldehyde in chromogenic reaction liquid is 0.5-2%;
III. sample detection
With reaction under the procyanidin ethanolic solution that configures and chromogenic reaction liquid normal temperature 5-12 minute, then with the absorbance of spectrophotometric determination reactant liquor at 496nm place, calibration curve method calculating procyanidin content.
2. the method for a kind of online detection procyanidin content as claimed in claim 1, when it is characterized in that the described sample that contains procyanidin is the finished product of online production, sample is used ultrasonic assist in dissolving at temperature 40-50 ℃.
3. the method for a kind of online detection procyanidin content as claimed in claim 1 when it is characterized in that the semi-finished product solution when the described sample that contains procyanidin is online production, is adjusted the semi-finished product solution concentration of alcohol to 60-95%.
4. a kind of method that detects procyanidin content as claimed in claim 1 is characterized in that the volume accounting of described hydrochloric acid in chromogenic reaction liquid is 10%, and the quality accounting of described vanillic aldehyde in chromogenic reaction liquid is 1%.
5. the method for a kind of online detection procyanidin content as claimed in claim 1 is characterized in that the reaction time is 8 minutes.
6. a kind of method that detects procyanidin content as claimed in claim 2 is characterized in that the described finished product that contains procyanidin to be measured is the procyanidin extract of ginkgo leaf.
7. the method for a kind of online detection procyanidin content as claimed in claim 1, it is characterized in that the described sample that contains procyanidin to be measured be in the ginkgo biloba p.e production run at line products.
8. the method for a kind of online detection procyanidin content as claimed in claim 6, it is characterized in that described ginkgo biloba p.e percentage by weight is 80% ethanol and assists a ruler in governing a country dissolving with ultrasonic down at 46 ℃, with reaction under the absolute ethyl alcohol nitrite ion normal temperature that contains percent by volume 10% hydrochloric acid and mass percent 1% vanillic aldehyde 8 minutes, absorbance is detected at the 496nm place, measures its content with calibration curve method.
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| CN102507558A (en) * | 2011-11-03 | 2012-06-20 | 湖南科技大学 | Rapid detection method of microorganism producing proanthocyanidin |
| CN102818863B (en) * | 2012-06-01 | 2014-02-05 | 浙江康恩贝制药股份有限公司 | Method for identifying proanthocyanidins in ginkgo leaf preparation |
| CN104198653B (en) * | 2014-09-17 | 2016-03-02 | 山东金诃药物研究开发有限公司 | The detection method of a kind of black matrimony vine |
| CN105223049A (en) * | 2015-08-28 | 2016-01-06 | 河南科技大学 | A kind of extracting method of plant leaf blade anthocyanidin |
| CN105510319A (en) * | 2015-12-07 | 2016-04-20 | 湖南科技大学 | Method for quickly identifying color of seed coats of rape seeds in early development period |
| CN107957402A (en) * | 2017-11-20 | 2018-04-24 | 江苏艾兰得营养品有限公司 | The ultraviolet spectrophotometry of quick measure nutrient health product procyanidins content |
| CN111579507A (en) * | 2020-05-22 | 2020-08-25 | 国珍健康科技（北京）有限公司 | Sulfuric acid-vanillin method for detecting content of procyanidine |
| CN114354523A (en) * | 2022-01-08 | 2022-04-15 | 杭州市农业科学研究院 | Rapid comparison method for content of procyanidine in radix tetrastigme leaves of different provenances |
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