CN105784904A - LC-MS/MS (liquid chromatography-tandem mass spectrometry) method for determining cordycepin metabolite in liver microsome - Google Patents
LC-MS/MS (liquid chromatography-tandem mass spectrometry) method for determining cordycepin metabolite in liver microsome Download PDFInfo
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Abstract
The invention belongs to the technical field of medicine detection, discloses an LC-MS/MS (liquid chromatography-tandem mass spectrometry) method for determining cordycepin metabolite in liver microsome, and particularly relates to the LC-MS/MS method for analyzing and determining the cordycepin metabolite in the liver microsome. The LC-MS/MS method mainly includes the steps of (1) incubation of the liver microsome containing cordycepin; (2) preprocessing of a sample; (3) analysis of the sample, thereby determining the cordycepin metabolite in the liver microsome. The LC-MS/MS has the advantages of convenience in operation, sample processing simplicity, high analysis speed, high specificity and high flexibility, provides technical support for researching extrametabolites of the cordycepin in the liver microsome while laying a methodological foundation for researching in-vivo and in-vitro metabolites of the cordycepin, and accordingly has a great significance.
Description
Technical field
The invention belongs to medicine detection technique field, be specifically related to a kind of LC-MS method measuring cordycepin metabolite in hepatomicrosome.
Background technology
Medicine enters after in organism, the reactions such as a series of oxidation, reduction, hydrolysis, combination can be there is under the effect of different enzymes, liver is the major organs that these metabolic responses occur medicine, it it is the body main place that carries out bioconversion, containing huge Cytochrome P450 (CYP450) the enzyme system participating in drug metabolism, I phase and the II phase metabolic response of most drug all rely on liver enzyme system and (first pass effect of medicine derives from this) occur.Therefore in drug metabolism field, the important component part that hepatomicrosome experiment in vitro is studied as In vitro metabolism is increasingly subject to people's attention.
Cordycepin is first the ucleosides antibiotics separated from fungus, Bently etc. confirm that cordycepin is by adenosine and a kind of nucleotide having the deoxypentose of carbon side chain to form in succession, therefore it is also referred to as 3'-Deoxyadenosine (3'-deoxyadenosine, 3'-dA), there is the biologic activity such as antibacterial, antitumor, antiinflammatory, have become as a study hotspot at present.The molecular formula of cordycepin is C10H13N5O3, molecular weight is 251, fusing point 230～231 DEG C, and ultraviolet light maximum absorption wavelength is 259nm.Cordycepin major part in vivo follows metabolism of purine nucleotide approach, at ADA Adenosine deaminase (adenosinedeaminase, ADA) quick deaminizating under effect and become the metabolite 3'-deoxyinosine nucleoside of inactive, all the other fractions are then phosphorylated to triphosphoric acid cordycepin (be likely cordycepin and have bioactive composition) (AgarwalRP, SagarSM, ParksRE.JrBiochemPharmacol, 1975,24 (6): 693-701；YUNG-JENTSAI,LIE-CHWENLIN,TUNG-HUTSAI.PharmacokineticsofAdenosineandCordycepin,aBioactiveConstituentofCordycepssinensisinRat,J.Agric.FoodChem.2010,58,4638-4643).Currently for the research of cordycepin, focus mostly at extraction and purification process and pharmacology activity research, up to now, have no with hepatomicrosome be model In vitro metabolism study.
Summary of the invention
The present invention seeks to the vacancy for existing research, it is provided that measuring the LC-MS detection method of cordycepin metabolite in hepatomicrosome, the method has easy and simple to handle, sample treatment is simple, analysis speed is fast, high specificity, highly sensitive advantage.Thering is provided technical support for studying cordycepin in-vitro metabolic product in hepatomicrosome, methodology basis is established in the inside and outside metabolism research for research cordycepin simultaneously, significant.
The technical solution used in the present invention is:
Measure the LC-MS method of cordycepin metabolite in hepatomicrosome, comprise the following steps:
1) temperature of cordycepin hepatomicrosome incubates cultivation
Culture bottle adds hepatomicrosome, NADP, NADH, G-6-P, G-6-PDH and MgCl2After, add three (methylol) aminomethane hydrochloride buffer and be made into liver microsomes incubation system；2-5min is incubated 37 DEG C of full temperature agitator temperature, it is quantitatively adding cordycepin three (methylol) aminomethane hydrochloride buffer again, starts reaction, after 30min, culture bottle is taken out from full temperature agitator, it is rapidly added cold organic solvent A and terminates metabolic response, obtain and warm incubate product；
2) sample treatment
Temperature is incubated the centrifugal 10min of product vortex oscillation 30s, 5000r/min, accurate Aspirate supernatant, after drying up under a nitrogen, obtains residue；Residue methanol redissolves, and after vortex oscillation, 5000r/min is centrifuged 10min, Aspirate supernatant, and after supernatant crosses 0.22 μm of microporous filter membrane, sample introduction 10 μ L carries out liquid quality inspection；
3) sample analysis
Carrying out cordycepin metabolite determination in hepatomicrosome, actual conditions is as follows:
Chromatographic condition:
Chromatographic column: DiamonsilTMODSC18；Mobile phase: methanol: water=15:85；Elution time: t=32min；Sample size: 10 μ L；Detection wavelength: λ=260nm；Column temperature: 30 DEG C；Flow velocity: 0.5mL/min；
Mass Spectrometry Conditions:
First mass spectrometric: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Electron spray voltage: 4.0bar；Dry gas stream speed: 10L/min；Dry temperature: 200 DEG C；
Second order ms: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Collision gas: nitrogen；Capillary voltage: 2.8kV；Taper hole voltage: 3.0V；Source temperature: 110 DEG C；Desolventizing temperature: 350 DEG C；Desolvation gas flow: 10L/min；Collision energy: 15-25eV.
Described measuring the LC-MS method of cordycepin metabolite, described step 1 in hepatomicrosome) organic solvent A is methanol or acetonitrile, its addition volume is 2-4 times of reaction system.
Described measure the LC-MS method of cordycepin metabolite, described step 3 in hepatomicrosome) in chromatographic column model be DiamonsilTMODSC18Chromatograph 250mm × 4.6mm, 5 μm.
Described measure the LC-MS method of cordycepin metabolite, step 1 in hepatomicrosome) in the pH of three (methylol) aminomethane hydrochloride buffer be 7.4.
Described measuring the LC-MS method of cordycepin metabolite, step 1 in hepatomicrosome) concentration range that the concentration range that concentration range is 2.0-4.0mg/mL, NADP is 0.5-1.0mmol/L, NADH of hepatomicrosome is 0.5-1.0mmol/L, G-6-P concentration in incubation system be the concentration range of 10mmol/L, G-6-PDH is 1.0-2.0IU/mL, MgCl2Concentration be 4.0mmol/L, cordycepin concentration range be 1.0-1.5mg/10mL.
Described measures the LC-MS method of cordycepin metabolite in hepatomicrosome, and described hepatomicrosome is the hepatomicrosome of mice, rat or people.
Described measure the LC-MS method of cordycepin metabolite, step 1 in hepatomicrosome) in the concentration of three (methylol) aminomethane hydrochloride buffer be 50mmol/L.
The method have the advantages that
The present invention adopts rat liver microsomes that cordycepin is carried out In vitro metabolism, by LC-MS detection method, metabolite is measured, cordycepin metabolic pathway in rat liver after measured, at deaminase (adenosinedeaminase, ADA) quick deaminizating under effect and become the metabolite 1 of inactive, confirm through MS1 and MS2 mass spectral analysis, [M+H] detected+To be 253.0932,137.0413 be sloughs the fragment ion peak of adenine after 3'-deoxyribose, and 110.0315 is the fragment obtained after hexatomic ring open loop in adenine after sloughing 3'-deoxyribose.It is thus determined that metabolite 1 is 3'-deoxyinosine nucleoside.It addition, have metabolite 2 at about 4.6min and 10.3min and have metabolite 3 to produce, structure is undetermined.
The present invention adopts rat liver microsomes that cordycepin is carried out In vitro metabolism, by optimizing reaction condition, determine its best incubation system, and set up a kind of cordycepin metabolite being suitable for and LC-MS method simple and quick, that selectivity good, detection sensitivity is high, it is possible to establish methodology basis for studying the metabolism of cordycepin inside and outside further.
Accompanying drawing explanation
Fig. 1 is the total ions chromatogram that hepatomicrosome converts cordycepin
Fig. 2 is hepatomicrosome total ions chromatogram
Fig. 3 is cordycepin total ions chromatogram
Fig. 4 is cordycepin extraction ion figure of metabolite 1 in hepatomicrosome
Fig. 5 is cordycepin structural formula of metabolite 1 in hepatomicrosome
Fig. 6 is the approach that cordycepin changes into metabolite 1 in hepatomicrosome
Fig. 7 is cordycepin MS fragment pathways of metabolite 1 in hepatomicrosome
Fig. 8 is cordycepin extraction ion figure of metabolite 2 in hepatomicrosome
Fig. 9 is cordycepin extraction ion figure of metabolite 3 in hepatomicrosome
Detailed description of the invention
Instrument and reagent
Oxidized form of nicotinamide-adenine dinucleotide I (NADP) and DPNH (NADH) are purchased from Shanghai Ru Ji biotechnology Development Co., Ltd.
G6P (G-6-P) and glucose-6-phosphate dehydrogenase (G-6-PDH) are purchased from Nanjing Dou Lai biotech firm.
Three (methylol) aminomethane (Tris) is purchased from Chemical Reagent Co., Ltd., Sinopharm Group.
Hydrochloric acid is purchased from Shandong Yuwang Industrial Co., Ltd. Chemical Company.
Magnesium chloride (is with six water of crystallization) purchased from Rui Jin, Tianjin specialization cosmetic company limited.
Methanol (analytical pure), methanol (chromatographically pure) are purchased from Shandong Yuwang Industrial Co., Ltd. Chemical Company.
Efficient liquid phase cordycepin is laboratory self-control, content >=98%.
SPF level SD male rat, body weight 230～250g, long-living bio tech ltd, Liaoning provide.
The high phase chromatograph of liquid of Agilent 1260 (Agilent company of the U.S.), it is furnished with quaternary pump, online degasser, automatic sampler, column oven and diode array detector, and Brooker 7.0TFT-ICR mass spectrometer system (Bruker company of Germany), water generation high phase chromatograph system and WatersLCTPremierXE system (Waters, US), desk centrifuge (Anting Scientific Instrument Factory, Shanghai), electronic balance (Mei Tesi-Tuo benefit instrument (Shanghai) Co., Ltd.), full temperature agitator (Harbin Donglian Electronic & Technology Development Co., Ltd.), RE52-99 Rotary Evaporators (Shanghai Yarong Biochemical Instrument Plant), KQ5200E type ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd.).
Solution preparation
Tris-HCl buffer: precision weighs three (methylol) aminomethane (Tris) 6.0565g, hydrochloric acid 3.5mL, adds deionized water and is settled to 1000mL；
NADP solution: precision weighing 18.96mg, adds Tris-HCl buffer and is settled to 2mL；
NADH solution: precision weighing 8.64mg, adds Tris-HCl buffer and is settled to 2mL；
G-6-P solution: precision weighing 72.96mg, adds Tris-HCl buffer and is settled to 2mL；
G-6-PDH solution: precision weighing 0.14mg, adds Tris-HCl buffer and is settled to 2mL；
MgCl2Solution: precision weighing 19.44mg, adds Tris-HCl buffer and is settled to 2mL；
Cordycepin solution: precision weighing 2mg, adds Tris-HCl buffer and is settled to 2mL；
Hepatomicrosome solution: laboratory is made by oneself, and concentration is 25.88mg/mL.
Embodiment 1
Measure the LC-MS method of cordycepin metabolite in hepatomicrosome, comprise the following steps
1) temperature of cordycepin hepatomicrosome incubates cultivation
Transformation system is 2mL, adds hepatomicrosome solution 154 μ L, NADP solution 166 μ L, NADH solution 164 μ L, G-6-P solution 166 μ L, G-6-PDH solution 144 μ L, MgCl in culture bottle2Solution 166 μ L, shakes up after adding 840 μ L tri-(methylol) aminomethane hydrochloride buffers, puts into the full temperature agitator temperature in preheated 37 DEG C and incubates 5min, adds 200 μ L cordycepin solution, starts reaction.In course of reaction, culture bottle is taken out after logical oxygen 30s, 30min by every 20min on liquid level from agitator, is rapidly added cold 6mL methanol and terminates metabolic response.
2) sample treatment
Temperature incubates product vortex oscillation 30s, centrifugal (rotating speed 5000r/min) 10min, accurate Aspirate supernatant, after drying up under a nitrogen, residue 1mL methanol redissolves, after vortex oscillation, centrifugal (rotating speed 5000r/min) 10min, Aspirate supernatant, crosses 0.22 μm of microporous filter membrane, and sample introduction 10 μ L carries out HPLC-MS detection.
3) LC-MS analysis
Temperature incubates product after sample treatment, carries out the mensuration of metabolite, and actual conditions is as follows: chromatographic column: DiamonsilTMODSC18Chromatograph (250mm × 4.6mm, 5 μm)；Mobile phase: methanol: water=15:85；Elution time: t=32min；Sample size: 10 μ L；Detection wavelength: λ=260nm；Flow velocity: 0.5mL/min.
Mass Spectrometry Conditions:
First mass spectrometric: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Electron spray voltage: 4.0bar；Dry gas stream speed: 10L/min；Dry temperature: 200 DEG C.
Second order ms: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Collision gas: nitrogen；Capillary voltage: 2.8kV；Taper hole voltage: 3.0V；Source temperature: 110 DEG C；Desolventizing temperature: 350 DEG C；Desolvation gas flow: 10L/min；Collision energy: 15-25eV.
Result is such as shown in 1-9, Fig. 1 is the total ions chromatogram that cordycepin converts in hepatomicrosome, Fig. 2 is blank hepatomicrosome total ions chromatogram, Fig. 3 is the total ions chromatogram of cordycepin standard substance, by comparison diagram 1 and Fig. 2, Fig. 3, can be seen that, after cordycepin converts in hepatomicrosome, at retention time respectively 4.6min, 10.3min with 13.0min all occurs in that the chromatographic peak newly increased, comparison diagram 3, can be seen that cordycepin converts completely, namely after cordycepin converts in hepatomicrosome, method by liquid quality detection, obtain metabolite.Fig. 4 is cordycepin extraction chromatography of ions figure of metabolite 1 in hepatomicrosome, it can be seen that be the metabolite of 4.6min in retention time, and by the supposition of liquid matter secondary fragment, as shown in Figure 6, obtain the structure of metabolite 1, as it is shown in figure 5, be 3'-deoxyinosine nucleoside.Fig. 7 speculates in conjunction with document to obtain, the metabolic pathway schematic diagram of cordycepin.Fig. 8 and Fig. 9 respectively cordycepin is found out in extraction ion figure, the figure of metabolite 2 and metabolite 3 in hepatomicrosome, can measure, by the method for embodiment 1, the metabolite that cordycepin converts in hepatomicrosome.
Claims (7)
1. measure the LC-MS method of cordycepin metabolite in hepatomicrosome, it is characterised in that comprise the following steps:
1) temperature of cordycepin hepatomicrosome incubates cultivation
Culture bottle adds hepatomicrosome, NADP, NADH, G-6-P, G-6-PDH and MgCl2After, add three (methylol) aminomethane hydrochloride buffer and be made into liver microsomes incubation system；2-5min is incubated 37 DEG C of full temperature agitator temperature, it is quantitatively adding three (methylol) aminomethane hydrochloride buffer of cordycepin again, starts reaction, after 30min, culture bottle is taken out from full temperature agitator, it is rapidly added cold organic solvent A and terminates metabolic response, obtain and warm incubate product；
2) sample treatment
Temperature is incubated the centrifugal 10min of product vortex oscillation 30s, 5000r/min, accurate Aspirate supernatant, after drying up under a nitrogen, obtains residue；Residue methanol redissolves, and after vortex oscillation, 5000r/min is centrifuged 10min, Aspirate supernatant, and after supernatant crosses 0.22 μm of microporous filter membrane, sample introduction 10 μ L carries out liquid quality inspection；
3) sample analysis
Carrying out cordycepin metabolite determination in hepatomicrosome, actual conditions is as follows:
Chromatographic condition:
Chromatographic column: DiamonsilTMODSC18；Mobile phase: methanol: water=15:85；Elution time: t=32min；Sample size: 10 μ L；Detection wavelength: λ=260nm；Column temperature: 30 DEG C；Flow velocity: 0.5mL/min；
Mass Spectrometry Conditions:
First mass spectrometric: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Electron spray voltage: 4.0bar；Dry gas stream speed: 10L/min；Dry temperature: 200 DEG C；
Second order ms: ionization pattern: electron spray ionisation (ESI)；Scan pattern: cation scans；Collision gas: nitrogen；Capillary voltage: 2.8kV；Taper hole voltage: 3.0V；Source temperature: 110 DEG C；Desolventizing temperature: 350 DEG C；Desolvation gas flow: 10L/min；Collision energy: 15-25eV.
2. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, its feature exists
In described step 1) organic solvent A is methanol or acetonitrile, its addition volume is 2-4 times of reaction system.
3. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, it is characterised in that: described step 3) in chromatographic column model be DiamonsilTMODSC18Chromatograph 250mm × 4.6mm, 5 μm.
4. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, it is characterised in that: step 1) in the pH of three (methylol) aminomethane hydrochloride buffer be 7.4.
5. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, it is characterised in that: step 1) concentration range that the concentration range that concentration range is 2.0-4.0mg/mL, NADP is 0.5-1.0mmol/L, NADH of hepatomicrosome is 0.5-1.0mmol/L, G-6-P concentration in incubation system be the concentration range of 10mmol/L, G-6-PDH is 1.0-2.0IU/mL, MgCl2Concentration be 4.0mmol/L, cordycepin concentration range be 1.0-1.5mg/10mL.
6. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, it is characterised in that: described hepatomicrosome is the hepatomicrosome of mice, rat or people.
7. the LC-MS method of cordycepin metabolite in mensuration hepatomicrosome according to claim 1, it is characterised in that: step 1) in the concentration of three (methylol) aminomethane hydrochloride buffer be 50mmol/L.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106970176A (en) * | 2017-06-06 | 2017-07-21 | 辽宁大学 | A kind of method of Paeoniflorin metabolite in measure hepatomicrosome |
| CN113624869A (en) * | 2021-07-30 | 2021-11-09 | 上海市疾病预防控制中心 | Method for rapidly determining organic matter conversion substance in real sample with high flux and high accuracy |
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| CN102643318A (en) * | 2012-03-28 | 2012-08-22 | 辽宁大学 | Method for extracting refined cordycepin from Cordyceps militaris fruit body |
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| CN1854730A (en) * | 2005-04-18 | 2006-11-01 | 清华大学 | Method for diagnosing gout and hyperuicemia by serum analysis |
| CN102643318A (en) * | 2012-03-28 | 2012-08-22 | 辽宁大学 | Method for extracting refined cordycepin from Cordyceps militaris fruit body |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106970176A (en) * | 2017-06-06 | 2017-07-21 | 辽宁大学 | A kind of method of Paeoniflorin metabolite in measure hepatomicrosome |
| CN113624869A (en) * | 2021-07-30 | 2021-11-09 | 上海市疾病预防控制中心 | Method for rapidly determining organic matter conversion substance in real sample with high flux and high accuracy |
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