CN109521118A - Method that is a kind of while measuring 4 kinds of phenolic substancess in myrtle fruit - Google Patents
Method that is a kind of while measuring 4 kinds of phenolic substancess in myrtle fruit Download PDFInfo
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- CN109521118A CN109521118A CN201811550491.1A CN201811550491A CN109521118A CN 109521118 A CN109521118 A CN 109521118A CN 201811550491 A CN201811550491 A CN 201811550491A CN 109521118 A CN109521118 A CN 109521118A
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- resveratrol
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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Abstract
A kind of ultra-performance liquid chromatography measure simultaneously gallic acid in myrtle fruit, ellagic acid, piceatannol, 4 kinds of phenolic substancess of resveratrol method, pretreated sample to be tested is subjected to Ultra Performance Liquid Chromatography instrument detection: gradient elution according to the following conditions, mobile phase is -0.2% phosphoric acid of acetonitrile；Elution requirement: 6% acetonitrile 0~2min, 6%~20% acetonitrile 2~4min, 20%~60% acetonitrile 4~10min, 6% 10~12min of acetonitrile；215~380nm of Detection wavelength；0.1~0.6ml/min of flow velocity；25~50 DEG C of column temperature；0.5~15 μ L of sampling volume；Diode array detector；WatersT3 chromatographic column (2.1mm × 100mm, 1.6 μm).Of the invention easy to be quick, reagent consumption is few, and stability is good, high sensitivity.
Description
Technical field
The present invention relates to Chinese medicine chemical component detection fields, specially a kind of to be examined simultaneously using ultra-performance liquid chromatography
The method for surveying gallic acid, ellagic acid, 4 kinds of piceatannol, resveratrol phenols components in myrtle fruit.
Background technique
Hill gooseberry Rhodomyrtus tomentosa (Ait.) Hassk., which is that Myrtaceae Myrtus is evergreen, spends more small filling
Wood, also known as harvest son, downy rosemyrtle fruit etc., it is a kind of excellent wild plant resource, is mainly distributed on country in Southeast Asia, abounds in especially
The south of state and Japan etc. is regional, and fruit is rich in flavones, polyphenol and polysaccharide and other multiple active components.Known phenolic substances tool
Have a pharmacological actions such as anti-oxidant, antitumor and anti-inflammatory, study polyphenol component in myrtle fruit have good learning value and
Exploitation prospect.
Currently, the detection method of phenolic substances mainly has ultraviolet spectrophotometry, high performance liquid chromatography and efficient liquid phase
Chromatographic tandem mass spectrography etc..Spectrophotometry is cumbersome, and sensitivity is low, poor reproducibility；And high performance liquid chromatography will be simultaneously
Measuring a variety of phenolic substancess, time-consuming, and reagent consumption is big；Although high performance liquid chromatography tandem mass spectrometry has high-resolution, Gao Ling
The advantages that sensitivity, high reproducibility, but testing cost is high, popularity rate is low.
Summary of the invention
The technical problem to be solved by the present invention is to be based on ultra performance liquid chromatography (UPLC) technology, establish a kind of more simple
Just, quickly, reagent consumption less, high sensitivity, gallic acid in myrtle fruit can be measured simultaneously, is ellagic acid, resveratrol, white
The method of the content of skin China fir alcohol.
The present invention solves above-mentioned technical problem and is adopted the technical scheme that: a kind of ultra performance liquid chromatography while measuring peach
Gallic acid in golden ma fruit, ellagic acid, piceatannol, 4 kinds of phenolic substancess of resveratrol method, comprising the following steps:
(1) myrtle fruit Med Mat Appreciation；
(2) configuration of standard solution: precision weighs gallic acid, ellagic acid, resveratrol, piceatannol reference substance and is placed in
In brown volumetric flask, add methanol to dissolve and be diluted to scale, shake up, be respectively prepared 100.00~500.00 μ g/mL of gallic acid,
100.00~500.00 μ g/mL of ellagic acid, 100.00~500.00 μ g/mL of piceatannol, 100.00~500.00 μ of resveratrol
The reference substance solution of g/mL；Face the used time, successively dilute above-mentioned standard solution with methanol respectively, is configured to the standard work of various concentration
Make liquid；
(3) sample pre-treatments: beating powder for myrtle fruit, and sieving, by obtained myrtle fruit sample powder, drying to constant weight,
It sets in drier and stores；0.3~10.0g myrtle fruit powder is accurately weighed to be placed in stuffed conical flask, precision addition 10~
200mL95% ethyl alcohol, weighed weight, under the conditions of 50~1500W, 25~100kHz, 25~65 DEG C ultrasonic extraction 20~
120min is let cool, and filtration is placed in brown volumetric flask and saves, and is crossed after 0.19~0.45 μm of filter membrane for content measuring；
(4) ultra performance liquid chromatography detects, and chromatographic condition is as follows:
Chromatographic column: 2.1mm × 100mm, 1.6 μm of WatersT3 chromatographic column；Mobile phase: second
- 0.2% phosphoric acid of nitrile；Condition of gradient elution: 6% acetonitrile 0~2min, 6%~20% 2~4min of acetonitrile, 20%~60% acetonitrile 4
~10min, 6% 10~12min of acetonitrile；Detection wavelength: 215~380nm；Flow velocity: 0.1~0.6ml/min；Column temperature: 25~50
℃；0.5~15 μ L of sampling volume.
Further, the invention also includes below for verifying the precision of the method, stability and the rate of recovery
Step:
(5) the method range of linearity, precision and detection limit calculate: accurate respectively to draw difference under above-mentioned chromatographic condition
The gallic acid of concentration, ellagic acid, piceatannol, resveratrol reference substance solution inject liquid chromatograph, with chromatographic peak peak face
Product y is ordinate, using concentration x as abscissa, draws standard curve；Respectively to gallic acid, ellagic acid, resveratrol, white skin
China fir alcohol reference substance solution carries out 3~15 parallel determinations, calculates gallic acid, ellagic acid, resveratrol, piceatannol peak area
With the RSD of transit time, verification method precision；It is provided according to IUPAC, calculates this law detection limit.
(6) stability test: precision weighs sample powder, prepares test sample by step (3) sample-pretreating method, respectively
0 after preparation, 4,8,12,24,48h sample introduction, peak area is measured；Calculate gallic acid, ellagic acid, resveratrol, piceatannol
Whether the relative standard deviation of peak area, verification sample are stable in 48h.
(7) recovery test: precision weighs 9 parts of myrtle fruit powder sample, prepares by step (3) sample-pretreating method
Test sample, the gallic acid prepared respectively to every a addition step (2), ellagic acid, resveratrol, piceatannol standard are molten
Liquid, each concentration of standard solution prepares 3 parts of parallel samples, and sample introduction is analyzed, calculates the rate of recovery and relative standard deviation.
The present invention using ultra-performance liquid chromatography simultaneously detect gallic acid in myrtle fruit, ellagic acid, piceatannol,
The content of resveratrol has the advantages that ultrahigh speed, high separation, high sensitivity, high stability and low consumption, and specific manifestation is such as
Under:
(1) ultra-performance liquid chromatography of the present invention simultaneously detect gallic acid in myrtle fruit, ellagic acid, piceatannol,
Resveratrol, sample pre-treatments use ultrasonic extraction, entire detection time 12min, and Mobile-phase reagent consumption only needs 2mL, has
It is easy, quickly, reagent consumption less, high sensitivity, high repeatability and other advantages.
(2) it is provided according to IUPAC, this law detection limit (3 σ, n=11) gallic acid is 7.55ng/mL, and ellagic acid is
2.32ng/mL, piceatannol 63.69ng/mL, resveratrol 4.59ng/mL.
(3) present invention can be used for the quality control and quantitative analysis to myrtle fruit medicinal material, while to containing gallic acid, tan
Spending other medicinal materials analysis of acid, piceatannol, resveratrol has important references value.
Detailed description of the invention
Fig. 1 is the ultraviolet spectrogram of gallic acid, ellagic acid, piceatannol, resveratrol reference substance in the present invention, wherein
A represents gallic acid, and B represents ellagic acid, and C represents piceatannol, and D represents resveratrol.
Fig. 2 is the canonical plotting of gallic acid reference substance in the present invention.
Fig. 3 is the canonical plotting of ellagic acid reference substance in the present invention.
Fig. 4 is the canonical plotting of middle white skin China fir alcohol reference substance of the present invention.
Fig. 5 is the canonical plotting of resveratrol reference substance in the present invention.
Fig. 6 be the present invention in gallic acid (A), ellagic acid (B), piceatannol (C), resveratrol (D) reference substance and
Myrtle fruit (E) sample chromatogram figure, wherein 1 represents gallic acid, 2 represent ellagic acid, and 3 represent piceatannol, and 4 represent white black false hellebore
Alcohol.
Specific embodiment
Below with reference to specific implementation method and attached drawing, technical scheme is described further.
The myrtle fruit medicinal material place of production used by 3 embodiments as described below is respectively MeiZhou,GuangDong, Guangxi Pingyue County and wide
Western Wuzhou is identified as the dry fruit of hill gooseberry Rhodomyrtus tomentosa (Ait.) Hassk..
Embodiment 1
(1) configuration of standard solution: precision weighs gallic acid, ellagic acid, resveratrol, piceatannol reference substance and is placed in
In brown volumetric flask, add methanol to dissolve and be diluted to scale, shake up, 123.40 μ g/mL of gallic acid, ellagic acid is respectively prepared
The reference substance solution of 370.05 μ g/mL, 242.26 μ g/mL of piceatannol, 225.50 μ g/mL of resveratrol；Again with methanol is successively
Above-mentioned standard solution is diluted, the standard working solution of various concentration is configured to.
(2) sample pre-treatments: MeiZhou,GuangDong myrtle fruit medicinal material beats powder, crosses 60 meshes, accurately weighs 2.0g fine powder, as
In 50ml stuffed conical flask, precision is added 95% EtOH Sonicate of 30mL (350W, 53kHz, 30 DEG C) and extracts 30min, lets cool, and filters
It crosses, is placed in brown volumetric flask and saves, 0.2 μm of filter membrane was crossed before the content measuring used time.
(3) chromatographic condition: chromatographic column: WatersT3 chromatographic column (2.1mm × 100mm, 1.6 μ
m)；Mobile phase: -0.2% phosphoric acid of acetonitrile；Condition of gradient elution: 0~2min, 6% acetonitrile；2~4min, 6%~20% acetonitrile；4
~10min, 20%~60% acetonitrile；10~12min, 6% acetonitrile；Detection wavelength: 280nm；Flow velocity: 0.20mL/min；Column temperature:
35℃；5 μ L of sampling volume.
(4) the method range of linearity, precision and detection limit: under step (3) chromatographic condition, accurate absorption is different dense respectively
The gallic acid of degree, ellagic acid, piceatannol, resveratrol reference substance solution inject liquid chromatograph, with chromatographic peak peak area
(y) it is ordinate, with concentration (x) for abscissa, draws standard curve.When gallic acid concentration is in 3.12~24.68 μ g/mL,
Ellagic acid concentration is in 4.63~74.01 μ g/mL ranges, and piceatannol concentration is in 5.05~121.13 μ g/mL ranges, resveratrol
For concentration in 0.224~4.51 μ g/mL range, gallic acid regression equation is y=3577.9x+1605.1, r=0.9996；Tan
Spending sour regression equation is y=3872.1x+1267.5, r=0.9997；Piceatannol regression equation is y=4568.9x+
1730.9；Resveratrol regression equation is y=9797x+117.11.
1 gallic acid of table, ellagic acid, resveratrol, piceatannol linear equation and related coefficient
11 parallel determinations are carried out to gallic acid, ellagic acid, resveratrol, piceatannol reference substance solution respectively, are not had
Gallate-based, ellagic acid, piceatannol, resveratrol peak area RSD be respectively 1.6%, 2.7%, 3.0%, 2.5%, migration
Time RSD is respectively 0.8%, 0.2%, 0.1%, 0.5%.It is provided according to IUPAC, this law detection limit (3 σ, n=11) galla turcica
Acid be 7.55ng/mL, ellagic acid 2.32ng/mL, piceatannol 63.69ng/mL, resveratrol 4.59ng/mL.
(5) stability test: precision weighs MeiZhou,GuangDong myrtle fruit sample powder, by step (2) sample pre-treatments side
Legal system available test product measures peak area respectively 0 after preparation, 4,8,12,24,48h sample introduction.Calculate gallic acid, ellagic acid,
The relative standard deviation of resveratrol, piceatannol peak area, respectively 2.1%, 1.8%, 2.7%, 2.9%, 2.3%,
3.1%, sample is stablized in 48h.
(6) recovery test: precision weighs 9 parts of MeiZhou,GuangDong myrtle fruit powder sample, by step (2) sample pre-treatments
Method prepares test sample, a certain concentration gallic acid for preparing respectively to every a test sample addition step (1), ellagic acid, white
Veratryl alcohol, piceatannol standard solution, each concentration prepares three parts of parallel samples, and sample introduction is analyzed, calculates the rate of recovery and opposite
Standard deviation.It the results are shown in Table 2.
The rate of recovery (n=3) that 4 kinds of phenolic substancess measure in 2 MeiZhou,GuangDong myrtle fruit of table
(7) sample analysis detects: gallic acid, ellagic acid, piceatannol, white black false hellebore in MeiZhou,GuangDong myrtle fruit medicinal material
The content results that alcohol is detected through ultra high efficiency liquid phase are shown in Table 3.
The assay (n=3) of 4 kinds of phenolic substancess in 3 myrtle fruit of table
Embodiment 2
(1) configuration of standard solution is the same as embodiment 1.
(2) sample pre-treatments: Guangxi Pingyue County myrtle fruit medicinal material beats powder, crosses 60 meshes, accurately weighs 3.0g fine powder, as
In 100ml stuffed conical flask, precision is added 95% EtOH Sonicate of 50mL (350W, 53kHz, 30 DEG C) and extracts 40min, lets cool, mistake
Filter, is placed in brown volumetric flask and saves, and 0.2 μm of filter membrane was crossed before the content measuring used time.
(3) chromatographic condition is the same as embodiment 1.
(4) the method range of linearity, precision and detection limit are the same as embodiment 1.
(5) stability test: precision weighs Guangxi Pingyue County myrtle fruit sample powder, by step (2) sample pre-treatments side
Legal system available test product measures peak area respectively 0 after preparation, 4,8,12,24,48h sample introduction.Calculate gallic acid, ellagic acid,
The relative standard deviation of piceatannol, resveratrol peak area, respectively 2.4%, 2.4%, 2.5%, 1.8%, 3.1%,
2.8%, sample is stablized in 48h.
(6) recovery test: precision weighs 9 parts of Guangxi Pingyue County myrtle fruit powder sample, by step (2) sample pre-treatments
Method prepares test sample, a certain concentration gallic acid for preparing respectively to every a test sample addition step (1), ellagic acid, white
Skin China fir alcohol, resveratrol standard solution, each concentration prepares three parts of parallel samples, and sample introduction is analyzed, calculates the rate of recovery and opposite
Standard deviation.It the results are shown in Table 4.
The rate of recovery (the n=that 4 Guangxi Pingyue County myrtle fruit gallic acid of table, ellagic acid, piceatannol, resveratrol measure
3)
(7) sample analysis detects: ultra performance liquid chromatography detects to obtain gallic acid, ellagic acid, piceatannol, resveratrol
Content results be shown in Table 5.
The assay (n=3) of gallic acid, ellagic acid, piceatannol, resveratrol in 5 myrtle fruit of table
Embodiment 3
(1) configuration of standard solution is the same as embodiment 1.
(2) sample pre-treatments: Guangxi Wuzhou myrtle fruit medicinal material beats powder, crosses 60 meshes, accurately weighs 2.0g fine powder, as
In 100ml stuffed conical flask, precision is added 95% EtOH Sonicate of 30mL (350W, 53kHz, 30 DEG C) and extracts 40min, lets cool, mistake
Filter, is placed in brown volumetric flask and saves, and 0.2 μm of filter membrane was crossed before the content measuring used time.
(3) chromatographic condition is the same as embodiment 1.
(4) the method range of linearity, precision and detection limit are the same as embodiment 1.
(5) stability test: precision weighs Guangxi Wuzhou myrtle fruit sample powder, by step (2) sample pre-treatments side
Legal system available test product measures peak area respectively 0 after preparation, 4,8,12,24,48h sample introduction.Calculate gallic acid, ellagic acid,
The relative standard deviation of piceatannol, resveratrol peak area, respectively 1.7%, 2.1%, 2.4%, 2.2%, 2.4%,
2.4%, sample is stablized in 48h.
(6) recovery test: precision weighs 9 parts of Guangxi Wuzhou myrtle fruit powder sample, by step (2) sample pre-treatments
Method prepares test sample, a certain concentration gallic acid for preparing respectively to every a test sample addition step (1), ellagic acid, white
Skin China fir alcohol, resveratrol standard solution, each concentration prepares three parts of parallel samples, and sample introduction is analyzed, calculates the rate of recovery and opposite
Standard deviation.It the results are shown in Table 6.
The rate of recovery (the n=that 6 Guangxi Wuzhou myrtle fruit gallic acid of table, ellagic acid, piceatannol, resveratrol measure
3)
(7) sample analysis detects: ultra performance liquid chromatography detects to obtain gallic acid, ellagic acid, piceatannol, resveratrol
Content results be shown in Table 7.
The assay (n=3) of gallic acid, ellagic acid, piceatannol, resveratrol in 7 myrtle fruit of table
Claims (4)
1. a kind of ultra performance liquid chromatography measures gallic acid in myrtle fruit, ellagic acid, piceatannol, resveratrol 4 simultaneously
The method of kind phenolic substances, which comprises the following steps:
(1) myrtle fruit Med Mat Appreciation；
(2) configuration of standard solution: precision weighs gallic acid, ellagic acid, resveratrol, piceatannol reference substance and is placed in brown
In volumetric flask, add methanol to dissolve and be diluted to scale, shake up, 100.00~500.00 μ g/mL of gallic acid, tan flower is respectively prepared
100.00~500.00 μ g/mL of acid, 100.00~500.00 μ g/mL of piceatannol, 100.00~500.00 μ g/mL of resveratrol
Reference substance solution；Face the used time, successively dilute above-mentioned standard solution with methanol respectively, is configured to the standard work of various concentration
Liquid；
(3) sample pre-treatments: beating powder for myrtle fruit, and sieving, by obtained myrtle fruit sample powder, drying to constant weight, sets dry
It is stored in dry device；0.3~10.0g myrtle fruit powder is accurately weighed to be placed in stuffed conical flask, precision addition 10~
200mL95% ethyl alcohol, weighed weight, under the conditions of 50~1500W, 25~100kHz, 25~65 DEG C ultrasonic extraction 20~
120min is let cool, and filtration is placed in brown volumetric flask and saves, and is crossed after 0.19~0.45 μm of filter membrane for content measuring；
(4) ultra performance liquid chromatography detects, and chromatographic condition is as follows:
Chromatographic column: 2.1mm × 100mm, 1.6 μm of WatersT3 chromatographic column；Mobile phase: acetonitrile-
0.2% phosphoric acid；Condition of gradient elution: 6% acetonitrile 0~2min, 6%~20% acetonitrile 2~4min, 20%~60% acetonitrile 4~
10min, 6% 10~12min of acetonitrile；Detection wavelength: 215~380nm；Flow velocity: 0.1~0.6ml/min；Column temperature: 25~50 DEG C；
0.5~15 μ L of sampling volume.
2. ultra performance liquid chromatography according to claim 1 measures gallic acid in myrtle fruit, ellagic acid, white skin simultaneously
The method of China fir alcohol, resveratrol, which is characterized in that further include the verifying step that the method range of linearity, precision and detection limit calculate
It is rapid:
Under above-mentioned chromatographic condition, precision draws gallic acid, ellagic acid, piceatannol, the resveratrol of various concentration respectively
Reference substance solution injects liquid chromatograph, and using chromatographic peak peak area y as ordinate, using concentration x as abscissa, it is bent to draw standard
Line；3~15 parallel determinations are carried out to gallic acid, ellagic acid, resveratrol, piceatannol reference substance solution respectively, are calculated
Gallic acid, ellagic acid, resveratrol, piceatannol peak area and transit time RSD, verification method precision；According to
IUPAC regulation, calculates this law detection limit.
3. ultra performance liquid chromatography according to claim 1 measures gallic acid in myrtle fruit, ellagic acid, white skin simultaneously
The method of China fir alcohol, resveratrol, which is characterized in that further include the verification step of following stability test:
Precision weighs sample powder, prepares test sample by step (3) sample-pretreating method, respectively 0 after preparation, 4,8,12,
24,48h sample introduction measures peak area；Calculating gallic acid, ellagic acid, resveratrol, the relative standard of piceatannol peak area are inclined
Whether difference, verification sample are stable in 48h.
4. ultra performance liquid chromatography according to claim 1 detects gallic acid in myrtle fruit, ellagic acid, white skin simultaneously
The method of China fir alcohol, resveratrol, which is characterized in that further include the verification step of following recovery test:
Precision weighs 9 parts of myrtle fruit powder sample, test sample is prepared by step (3) sample-pretreating method, respectively to each
Gallic acid, the ellagic acid, resveratrol, piceatannol standard solution of part addition step (2) preparation, each concentration of standard solution
3 parts of parallel samples are prepared, and sample introduction is analyzed, calculates the rate of recovery and relative standard deviation.
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| CN110108808A (en) * | 2019-04-12 | 2019-08-09 | 广西壮族自治区兽医研究所 | Method that is a kind of while evaluating oxidation-resistant active ingredient and content in downy rosemyrtle root |
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| CN113480510A (en) * | 2020-09-12 | 2021-10-08 | 中国科学院华南植物园 | Rapid preparation and application of phloroglucinol derivatives in myrtle fruits |
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