CN106596800B - A kind of a variety of flavone component rapid assay methods of Herba Epimedii based on UPLC/Q-TOF - Google Patents
A kind of a variety of flavone component rapid assay methods of Herba Epimedii based on UPLC/Q-TOF Download PDFInfo
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Abstract
The present invention provides a kind of a variety of flavone component rapid assay methods of Herba Epimedii based on UPLC/Q-TOF, including two steps: 1) extracting epimedium herb with 40% EtOH Sonicate;2) qualitative and quantitative determination is carried out to icariin, Epimedin A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B and the precious leaves of pulse plants glycosides II ingredient in epimedium herb using ultra performance liquid chromatography-flight time mass spectrum joint technology.The present invention provides a kind of method for efficiently carrying out qualitative and quantitative detection to many indexes ingredient in epimedium herb using LC-MS, and this method detection efficiency is high, as a result accurately, has significant ground meaning in the quality control of epimedium herb crude drug.
Description
Technical field
The present invention provides a kind of chromatographic process, more specifically to a kind of Herba Epimedii based on UPLC/Q-TOF is a variety of
Flavone component rapid assay methods.
Technical background
Flavone compound (flav onoids) is a kind of important Secondary Metabolite Production in Plants, formed in flower color,
Pollen germination, attract pollination entomophila and seed dispersal, resist ultraviolet radiation, prevent pathogenic microorganism infect and plant with it is micro-
It plays a significant role during biological identification etc. mutually.In addition, flavonoids also has anti-inflammatory, antibacterial, anti-oxidant, antitumor etc.
Multiple biological activities are the principle active components of some important Chinese medicines.Have proven to (the letter of Herba Epimedii medicinal ingredient flavone compound
Claim " effective flavonoids ") have and adjusts patrogenesis, prevent osteoporosis, adjust immune function, is anti-oxidant, anti-aging, anti-swollen
The physiological functions such as tumor, anti-hepatotoxin, vasodilator, thus Herba Epimedii be considered as China it is most widely used, it is most long, most open
Send out one of the Chinese medicine of potentiality.The chemical component of epimedium herb mainly has flavone compound and polysaccharide compound, Herba Epimedii
Effective component is primarily referred to as flavone compound in medicinal material, and the content of barren wort total chromocor accounts for 1.01%-8.81%, " pharmacopeia " rule
General flavone is determined not less than 5%.Characteristic component is icariin, content about 0.1897%-1.8742%, " medicine in epimedium herb
Allusion quotation " must not provide less than 0.50%.Wherein, main epimedium flavone constituents have icariin, Epimedin A, Epimedin B,
Epimedin C, icariside I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, the precious leaves of pulse plants
10 kinds of glycosides II etc..
Summary of the invention
To solve the above problems, the present invention provides a kind of a variety of flavone components of the Herba Epimedii based on UPLC/Q-TOF are quick
Measuring method, including two steps:
1) epimedium herb is extracted with 40% EtOH Sonicate;
2) using ultra performance liquid chromatography-flight time mass spectrum joint technology to the icariin in epimedium herb, court
The leaves of pulse plants determines A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides
A, arrow leaves of pulse plants glycosides B and precious leaves of pulse plants glycosides II ingredient carry out qualitative and quantitative determination.
The chromatographic condition of the ultra performance liquid chromatography are as follows: 50mm × 2.1mm, 3 μm, C18Chromatographic column Phenomenex;Stream
Dynamic phase: 0.1% aqueous formic acid and acetonitrile, flow velocity: 0.2mL/min;Column temperature: 40 DEG C;Sample volume: 2 μ L, condition of gradient elution
Are as follows:
0~8min, 40%~53% acetonitrile;
8~8.1min, 40% acetonitrile;
8.1~10min, 40% acetonitrile.
The flight time mass spectrum be Q-TOF high resolution mass spectrum, the Mass Spectrometry Conditions of Q-TOF high resolution mass spectrum are as follows: ion source:
ESI, positive/negative ion mode acquire respectively, IS:+5500V/-4500V;GS1:50Psi;CUR:20Psi;GS2:45Psi;
TEMP:550 DEG C;DP:65V;CE:45V;CES:15V;Detection pattern is information association acquisition mode, and multiple quality loses and moves
State background deduction is the condition for triggering second level, meets the condition and preferentially carries out second level scanning.
The method have the benefit that: the present invention provide it is a kind of using LC-MS efficiently in epimedium herb
The method that many indexes ingredient carries out qualitative and quantitative detection, this method detection efficiency is high, as a result accurately, raw in epimedium herb
There is significant meaning in the quality control of medicine.
Detailed description of the invention
The XIC of Fig. 1 mixing reference substance schemes;
The TIC of Fig. 2 mixing reference substance schemes;
The XIC of Fig. 3 sample schemes;
The TIC of Fig. 4 sample schemes;
Remarks: equipment is the triple level four bars mass spectrums of API4000 type using AB company (AB SCIEX company) in the present invention
Instrument, does not connect UV detector module, detection pattern MRM+, totally 10 standard items, and contains qualitative, quota ion pair totally 20,
So can only obtain XIC figure and TIC figure from workstation software." Fig. 3 Fig. 4 mass spectrogram " is that work station carries quantitation software
The quota ion figure that MultiQuant 3.0 is extracted according to quantitative parameter can be corresponded with the extraction ion overlay chart of Fig. 2,
So It is not necessary to being labeled again to each ion.
Specific embodiment
The investigation of 1 chromatographic condition of embodiment
1. chromatography and Mass Spectrometry Conditions
UPLC condition: chromatographic column Phenomenex C18 column (50mm × 2.1mm, 3 μm);Mobile phase: A is aqueous formic acid
(0.1%), B is acetonitrile, gradient elution, elution program are as follows: 0~8min, 40%~53%B;8~8.1min, 40%B;8.1~
10min, 40%B.Flow velocity: 0.2mL/min;Column temperature: 40 DEG C;Sample volume: 2 μ L.
MS/MS Mass Spectrometry Conditions: ion source: ESI;IS:5500V;GS1:55Psi;CUR:15Psi;GS2:55Psi;TEMP:
600℃;Detection pattern: MRM+;Collision gas: Medium.Quota ion pair, qualitative ion pair remove cluster voltage
(Declusteringpotential, DP), collision energy (Collision energy, CE).
Q-TOF high resolution mass spectrum condition: ion source: ESI, positive/negative ion mode acquire respectively, IS:+5500V/-
4500V;GS1:50Psi;CUR:20Psi;GS2:45Psi;TEMP:550 DEG C;DP:65V;CE:45V;CES:15V;Detection pattern
For IDA (information association acquisition mode), multiple quality loss (MMDF) and dynamic background deduct the item that (DBS) is triggering second level
Part meets the condition and preferentially carries out second level scanning.
2. prepared by reference substance stock solution
Icariin, Epimedin A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-mouse are taken respectively
Lee's glycosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II reference substance are appropriate, accurately weighed, are placed in same 25mL and hold
In measuring bottle, additive color spectrum methanol makes to dissolve in right amount, is made containing icariin, Epimedin A, Epimedin B, epimedin C, icariside
I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, treasured leaves of pulse plants glycosides II be respectively 0.1024,
0.1004, the mixing control of 0.0972,0.1044,0.1028,0.0992,0.1004,0.1068,0.1020,0.0984mg/mL
Product stock solution.
3. prepared by test solution
Medicinal material pretreatment: the fresh medicinal material sample of different sources is cleaned, and sets in baking oven 60 DEG C of drying, take dry blade in
It is crushed in high speed disintegrator, it is spare to cross No. 3 sieves.
Test solution preparation: taking epimedium herb powder about 0.2g, accurately weighed, sets in 10mL measuring bottle, is added 40%
Appropriate amount of ethanol, ultrasonic 40min take out, let cool to room temperature, then be settled to scale with 40% ethyl alcohol, mix, and cross 0.22 μm of micropore filter
Film to get.
4. detecting the confirmation of limit
It takes the reference substance stock solution under above-mentioned item appropriate, is diluted step by step, examined according to above-mentioned chromatography, Mass Spectrometry Conditions sample introduction
It surveys, concentration when with target compound S/N=3 is limited as its detection;It is icariin, Epimedin A, Epimedin B, epimedin C, excessive
The detection of the sheep leaves of pulse plants time glycosides I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II
Limit is respectively as follows: 0.47ng/mL, 0.72ng/mL, 0.89ng/mL, 0.87ng/mL, 0.52ng/mL, 0.67ng/mL, 0.72ng/
mL、0.43ng/mL、0.58ng/mL、0.12ng/mL。
5. linear relationship is investigated
It takes above-mentioned mixing reference substance stock solution appropriate, is mixed with the series that chromatography methanol is diluted to 9 various concentrations step by step
Reference substance solution, 0.22 μm of miillpore filter filtration distinguish 2 μ L of sample introduction by above-mentioned chromatography, Mass Spectrometry Conditions, are vertical with peak area (Y)
Coordinate is that abscissa draws standard curve with sample introduction concentration (X).
6. Precision Experiment
Precision draws mixed reference substance solution 2 μ L (icariin, Epimedin A, Epimedin B, epimedin C, icariside
I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II content are respectively as follows:
512ng/mL、502ng/mL、486ng/mL、522ng/mL、514ng/mL、496ng/mL、502ng/mL、534ng/mL、
510ng/mL, 492ng/mL), continuous sample introduction 5 times, the peak area of 10 kinds of ingredients is recorded respectively, calculates RSD value, as a result Herba Epimedii
Glycosides is 1.38%, Epimedin A 1.72%, Epimedin B 2.37%, epimedin C 2.15%, icariside I are
2.34%, icariside I I is 2.78%, 2 "-rhamnopyranosyl icariside I I is 1.21%, arrow leaves of pulse plants glycosides A is 1.87%,
Arrow leaves of pulse plants glycosides B is 2.64%, treasured leaves of pulse plants glycosides II is 1.83%, shows that instrument precision is good.
7. repeated experiment
Precision weighs 6 parts of No. 1 medicinal material sample, prepares test solution, 2 μ L of sample introduction, according to 10 kinds of ingredients of calculated by peak area
Content, icariin, Epimedin A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-as the result is shown
Rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, the average content difference 0.50% of precious leaves of pulse plants glycosides II, 2.08%,
0.95%, 0.89%, 0.002%, 0.07%, 0.02%, 0.96%, 0.02%, 0.07%, RSD be 1.35%,
2.22%, 1.55%, 2.34%, 2.56%, 2.77%, 1.54%, 1.75%, 2.18%, 2.04%, show that this method repeats
Property is good.
8. stability experiment
The test solution in same test solution step 7 is taken, by above-mentioned chromatographic condition, place 0 at room temperature respectively,
2,4,8, sample introduction is analyzed by 12h, records peak area.Icariin, Epimedin A, Epimedin B, epimedin C, Herba Epimedii as the result is shown
Secondary glycosides I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II peak area
RSD is respectively 2.13%, 2.21%, 1.47%, 1.85%, 1.42%, 1.85%, 1.04%, 1.72%, 2.09%,
1.58%, show that this method has good stability.
9. the rate of recovery is tested
5 parts of each 0.1g of epimedium herb sample are taken, it is accurately weighed, it is placed in 10mL measuring bottle, it is accurate respectively that mixing pair is added
(contain icariin, Epimedin A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-sandlwood according to product 0.2mL
Glycosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II mass concentration be respectively as follows: 512ng/mL, 502ng/mL,
486ng/mL, 522ng/mL, 514ng/mL, 496ng/mL, 502ng/mL, 534ng/mL, 510ng/mL, 492ng/mL), preparation
At test solution, sample introduction measurement records peak area, calculates sample recovery rate and RSD value, icariin, Epimedin A, towards the leaves of pulse plants
Determine B, epimedin C, icariside I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B,
The rate of recovery of precious leaves of pulse plants glycosides II is respectively 99.2%, 98.4%, 101.7%, 98.5%, 103.6%, 102.7%, 99.1%,
103.9%, 97.6%, 104.5%, RSD value be respectively 1.37%, 1.48%, 1.49%, 2.12%, 2.44%, 1.65%,
1.89%, 2.45%, 2.93%, 2.52%.Show that this method rate of recovery is good.
The a variety of flavone component rapid assay methods of Herba Epimedii of the embodiment 2 based on UPLC/Q-TOF are in Herba Epimedii sample
Using
Precision weighs different sources E. Pubescens powder 2.0g respectively, prepares test sample according to the method in embodiment 1
Solution, 2 μ L of sample introduction calculate content.
Using the chromatography in embodiment 1, Mass Spectrometry Conditions, positive and negative ion type collection is carried out to E. Pubescens sample, entirely
Total ion current figure is scanned, acquired results import PeakView software, and it is correct less than 5ppm, isotope distribution will to meet quality error
And the compound containing secondary fragment is confirmed as target substance, in conjunction with functions, number such as PeakView software Formula Finder
According to library and secondary fragment cracking rule, has found 32 compounds (as described in Fig. 3,4), lead altogether from Herba Epimedii alcohol extracting sample
It to be flavones ingredient.By to the excessive sheep of leaves of pulse plants glycosides, Epimedin A, Epimedin B, epimedin C, icariside I, icariside
II, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow leaves of pulse plants glycosides B, precious leaves of pulse plants glycosides II second level spectrum analysis known to (such as Fig. 1,2
It is described), containing the secondary fragment ions for sloughing pyranoside group and alkyl, meet the cracking rule of flavone compound.
The qualitative analysis, for the selection of quantitative detection classes of compounds and corresponding MRM quantitative analysis method foundation provide it is accurate and
Reliable reference data.
Claims (1)
1. a kind of a variety of flavone component rapid assay methods of Herba Epimedii based on UPLC/Q-TOF, it is characterised in that: including two
Step:
1) epimedium herb is extracted with 40% EtOH Sonicate;
2) using ultra performance liquid chromatography-flight time mass spectrum joint technology to the icariin, fixed towards the leaves of pulse plants in epimedium herb
A, Epimedin B, epimedin C, icariside I, icariside I I, 2 "-rhamnopyranosyl icariside I I, arrow leaves of pulse plants glycosides A, arrow
Leaves of pulse plants glycosides B and precious leaves of pulse plants glycosides II ingredient carry out qualitative and quantitative determination;
The chromatographic condition of the ultra performance liquid chromatography are as follows: 50mm × 2.1mm, 3 μm, C18Chromatographic column Phenomenex;Mobile phase:
0.1% aqueous formic acid and acetonitrile, flow velocity: 0.2mL/min;Column temperature: 40 DEG C;Sample volume: 2 μ L, condition of gradient elution are as follows:
0~8min, 40%~53% acetonitrile;
8~8.1min, 40% acetonitrile;
8.1~10min, 40% acetonitrile;
The flight time mass spectrum be Q-TOF high resolution mass spectrum, the Mass Spectrometry Conditions of Q-TOF high resolution mass spectrum are as follows: ion source: ESI,
Positive/negative ion mode acquires respectively, IS:+5500V/-4500V;GS1:50Psi;CUR:20Psi;GS2:45Psi;TEMP:550
℃;DP:65V;CE:45V;CES:15V;Detection pattern is information association acquisition mode, multiple quality loss and dynamic background button
Except the condition to trigger second level, meets the condition and preferentially carry out second level scanning.
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