CN110531007B - Detection method of arachidonic acid-like substance - Google Patents

Detection method of arachidonic acid-like substance Download PDF

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CN110531007B
CN110531007B CN201910999577.0A CN201910999577A CN110531007B CN 110531007 B CN110531007 B CN 110531007B CN 201910999577 A CN201910999577 A CN 201910999577A CN 110531007 B CN110531007 B CN 110531007B
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唐堂
王宏
郑彬
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Wuhan Mai Tver Biological Technology Co ltd
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Jiaxing Metware Metabolic Biological Technology Co ltd
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Abstract

The invention discloses a method for detecting arachidonic acid-like substances, which comprises the following steps of adding 300 parts of water containing 0.005% BHT into 100 parts of samples by volume fraction; adding 500 parts of methyl tert-butyl ether, centrifuging, transferring an upper organic phase, and keeping a lower aqueous phase; adding 500 parts of ethyl acetate into the lower aqueous phase, centrifuging, and combining the upper organic phase with the upper organic phase obtained in the previous step; and blowing the combined upper organic phase by using nitrogen, re-dissolving by using an acetonitrile-isopropanol solution, and detecting by using a machine. The internal standard selected by the method is stable, accurate detection is realized in a positive and negative ion mode, no interference is generated on the detection of the arachidonic acid-like substance, the detection repeatability is good, impurities are obviously reduced in the detection method, the pollution to an instrument can be greatly reduced, the method is convenient and quick, the extraction time is short, the detection signal-to-noise ratio is obviously improved, and the sensitivity is greatly improved.

Description

Detection method of arachidonic acid-like substance
Technical Field
The invention belongs to the technical field of detection of arachidonic acid-like substances, and particularly relates to a method for detecting the arachidonic acid-like substances.
Background
Metabolites such as hydroxyeicosatetraenoic acid (HETES), dihydroxyeicosatetraenoic acid (DiHETES), epoxyeicosatetraenoic acid (EETs), Prostaglandin (PGs) and Thromboxane (TX), which are produced by enzymatic metabolism of arachidonic acid by cyclooxygenase (COX-2), Lipoxygenase (LOX) and cytochrome P450 enzymes, are eicosanoic acids which are the main components of eicosanoids, and the content of these endogenous eicosanoids in biological fluids and tissues is very low.
However, the existing pretreatment preparation method for the substances has the problems of high cost, complexity, low content in samples, difficulty in detection and the like. Therefore, how to develop a method which is low in cost, convenient, and capable of improving detection sensitivity and reducing detection noise is a technical problem to be solved in the prior art.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made in view of the above-mentioned technical drawbacks.
Therefore, as one aspect of the invention, the invention overcomes the defects in the prior art and provides a method for detecting arachidonic acid-like substances.
In order to solve the technical problems, the invention provides the following technical scheme: a method for detecting arachidonic acid-like substances comprises,
to 100 parts by volume of the sample, 300 parts of water containing 0.005% BHT was added;
adding 500 parts of methyl tert-butyl ether, centrifuging, transferring an upper organic phase, and keeping a lower aqueous phase;
adding 500 parts of ethyl acetate into the lower aqueous phase, centrifuging, and combining the upper organic phase with the upper organic phase obtained in the previous step;
and blowing the combined upper organic phase by using nitrogen, re-dissolving by using an acetonitrile-isopropanol solution, and detecting by using a machine.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: adding 500 parts of methyl tert-butyl ether, and centrifuging, wherein the centrifugation comprises centrifuging at 10000rpm at 4 ℃ for 3 min; adding 500 parts of ethyl acetate into the lower aqueous phase, and centrifuging, including centrifuging at 10000rpm at 4 ℃ for 3 min.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: the re-dissolving is carried out by using an acetonitrile-isopropanol solution, wherein the volume ratio of acetonitrile: 1-isopropyl alcohol: 1.
as a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: the sample comprises a plasma sample.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: and the method also comprises the step of replacing a solvent with the 2-chlorophenylalanine to serve as an internal standard, and reflecting the collection condition of an actual sample through the peak area and retention time of the 2-chlorophenylalanine in the detection process.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: the concentration of the 2-chlorophenylalanine is 1 mu g/mL.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: and the method also comprises the steps of using a mixed standard sample of 4, 4' -methylenebis (2-chloroaniline), p-anisidine, L-tyrosine methyl ester, 3-chloroaniline, 2, 4-dimethylquinoline, sulfapyridine, atrazine, sulfadoxine, DL-leucine, N-benzoyl-L-tyrosine ethyl ester, 6-phenyl-2-thiouracil, N- (o-toluoyl) glycine, 2-methyl-5-nitroimidazole-1-ethanol, glycyrrhetinic acid, flavanone, epsilon-caprolactone and 2-aminopyridine as a quality control material, detecting at least two pins of the quality control material each time, and analyzing the state of the detector according to the overlapping condition of spectrograms.
As a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: the 4, 4' -methylene bis (2-chloroaniline) is prepared from the following components in percentage by mass: p-anisidine: l-tyrosine methyl ester: 3-chloroaniline: 2, 4-dimethylquinoline: sulfapyridine: atrazine: sulfadoxine: DL-leucine: N-benzoyl-L-tyrosine ethyl ester: 6-phenyl-2-thiouracil: n- (o-toluoyl) glycine: 2-methyl-5-nitroimidazole-1-ethanol: glycyrrhetinic acid: flavanone: epsilon-caprolactone: 2-aminopyridine ═ 1: 0.5: 0.5: 2: 1: 0.4: 0.1: 0.1: 0.2: 0.5: 0.5: 1: 1: 0.1: 0.5: 2: 0.2.
as a preferred scheme of the detection method of the arachidonic acid-like substance, the method comprises the following steps: the concentration of the 4, 4' -methylene-bis (2-chloroaniline) is 1 mu g/mL, the concentration of p-anisidine is 0.5 mu g/mL, the concentration of L-tyrosine methyl ester is 0.5 mu g/mL, the concentration of 3-chloroaniline is 2 mu g/mL, the concentration of 2, 4-dimethylquinoline is 1 mu g/mL, the concentration of sulfapyridine is 0.4 mu g/mL, the concentration of atrazine is 0.1 mu g/mL, the concentration of sulfadoxine is 0.1 mu g/mL, the concentration of DL-leucine is 0.2 mu g/mL, the concentration of N-benzoyl-L-tyrosine ethyl ester is 0.5 mu g/mL, the concentration of 6-phenyl-2-thiouracil is 0.5 mu g/mL, the concentration of N- (o-toluoyl) glycine is 1 mu g/mL, and the concentration of p-anisidine is 0.5 mu g/mL, The concentration of 2-methyl-5-nitroimidazole-1-ethanol is 1 mug/mL, the concentration of glycyrrhetinic acid is 0.1 mug/mL, the concentration of flavanone is 0.5 mug/mL, the concentration of epsilon-caprolactone is 2 mug/mL, and the concentration of 2-aminopyridine is 0.2 mug/mL.
The invention has the beneficial effects that: according to the invention, various arachidonic acid compounds are detected simultaneously, the extraction rate of arachidonic acid substances is higher by combining ethyl acetate and MTBE than by extracting with a single solvent, the signal-to-noise ratio during detection is obviously improved, and the detection sensitivity of the substances is obviously improved by the method.
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In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without inventive exercise. Wherein:
FIG. 1 is a chromatogram peak of 23 arachidonic acid detection.
FIG. 2 is a diagram showing the peak overlapping condition of 17 mixed-standard quality control substances in a liquid chromatography-mass spectrometer.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with examples are described in detail below.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1:
the method adopts the ultra-high performance liquid chromatography-triple quadrupole/linear ion TRAP tandem mass spectrometry (UPLC-QTRAP) technology, the mass spectrometer is AB Sciex Q-TRAP 6500, and the analysis software is Multi Quant.
100uL of human plasma samples were taken in EP tubes and 300uL of water (containing 0.005% BHT) was added;
adding 500uL MTBE (methyl tert-butyl ether) into an EP tube, uniformly mixing by vortex, centrifuging for 3min at 10000rpm under the condition of 4 ℃, transferring an upper layer of organic phase into a new EP tube, and keeping a lower layer of water phase;
adding 500uL of ethyl acetate into the lower aqueous phase, uniformly mixing by vortex, centrifuging for 3min at 10000rpm under the condition of 4 ℃, and combining the upper organic phase with the upper organic phase obtained in the previous step;
and blowing the combined upper organic phase by using nitrogen, re-dissolving by using acetonitrile/isopropanol (1: 1), filling into a sample bottle, and detecting by using a machine.
Liquid phase mass spectrum conditions:
mobile phase a was acetonitrile/water/acetic acid 60/40/0.02(v/v/v), phase B was acetonitrile/isopropanol 50/50(v/v), flow rate was 0.4mL/min, column temperature 40 ℃, injector temperature: 4 ℃, sample size 10 μ L, column: ACQUITY UPLC HSS T3(i.d.2.1X100mm,1.8 μm), MRM detection window set to 60sec, Target Scan Time set to 1.000sec, IonSpray Voltage set to-4500V, Ion Mode set to negative, Temperature set to 550 ℃, Ion Source Gas 1 to 50psi, Ion Source Gas 2 to 60psi, Entrance Potential to 10psi, Curtain Gas to 35psi, mobile phase gradients are given in the following table:
Time(min) A(％) B(％)
0 99.9 0.1
4.0 45 55
5.0 1 99
6.8 1 99
7.0 99.9 0.1
10.0 Stop
ion pair information of the machine:
Figure BDA0002240856280000041
Figure BDA0002240856280000051
the chromatogram obtained by the detection on the computer is shown in figure 1, and as can be seen from figure 1, the chromatographic peak separation is good and the repeatability is good by adopting the sample extraction method.
In addition, the invention adopts 2-chlorophenylalanine as an internal standard, water as a solvent to prepare an internal standard extracting solution with the concentration of 1 mug/mL, and the internal standard 2-chlorophenylalanine extracting solution replaces a pure organic solvent to extract experimental samples, so that the concentration of the internal standard in each sample is ensured to be consistent, and the collection condition of the actual sample is reflected by the collection condition of the internal standard. In order to monitor whether the running state of the instrument is normal or not in the detection process, the quality control product for metabonomics detection consists of 17 mixed labels which are screened, the solvent of the 17 mixed labels is 70 percent methanol water, and the 17 standard samples and the final using concentration of the quality control product are shown in a table 1:
TABLE 1
Figure BDA0002240856280000052
Figure BDA0002240856280000061
Figure BDA0002240856280000071
Figure BDA0002240856280000081
The peak overlap of 17 mixed standard quality control products on the LC-MS instrument is shown in FIG. 2. As can be seen from figure 2, the peak areas RSD of the repeated samples of the 17 mixed standard quality control products are all within 10%, and under the experimental conditions of the invention, the retention time of the 17 mixed standard quality control products is dispersed within 0.5-6.5 min, and the retention time of the samples is dispersed within 0.5-6 min, and the 17 mixed standard quality control products of the invention have good repeatability and good chromatographic peak separation and superposition, so that the 17 mixed standard quality control products of the invention can accurately reflect the stability of the instrument operation in the detection process of the arachidonic acid-like substances.
The detection limits of various types of arachidonic acid substances which can be detected in the same reaction hole are shown in the following table:
name of substance Detection limit (nM)
5-HETrE 1.00
RvD1 1.00
LTB4 1.00
(±)5-HEPE 0.10
(±)4-HDHA 0.10
13-HOTrE 0.10
PGD2 0.10
5,6-DiHETrE 0.10
TxB3 0.10
9-HOTrE 0.10
(±)8-HETE 0.10
9,10-DiHOME 0.10
(±)17-HDHA 0.10
PGE3 0.10
(±)15-HETE 0.10
(±)16-HETE 1.00
PGJ2 1.00
5(S),6(S)-DiHETE 1.00
5(S),15(S)-DiHETE 1.00
(±)7-HDHA 1.00
PGK1 1.00
PDX 1.00
5-oxoETE 1.00
Example 2 (comparative example):
100uL of plasma sample was taken in an EP tube, and 300uL of water (containing 0.005% BHT) was added;
adding 500uL MTBE (methyl tert-butyl ether) into an EP tube, uniformly mixing by vortex, centrifuging for 3min at 10000rpm under the condition of 4 ℃, transferring an upper layer of organic phase into a new EP tube, and keeping a lower layer of water phase;
adding 500uL of MTBE (methyl tert-butyl ether) into the lower aqueous phase, uniformly mixing by vortex, centrifuging for 3min at 4 ℃ at 10000rpm, and combining the upper organic phase with the upper organic phase obtained in the previous step;
and blowing the combined upper organic phase by using nitrogen, re-dissolving by using acetonitrile/isopropanol (1: 1), filling into a sample bottle, and waiting for detection on a machine.
Example 3 (comparative example):
100uL of plasma sample was taken in an EP tube, and 300uL of water (containing 0.005% BHT) was added;
adding 500uL of ethyl acetate into an EP tube, uniformly mixing by vortex, centrifuging for 3min at 10000rpm under the condition of 4 ℃, transferring an upper layer of organic phase into a new EP tube, and keeping a lower layer of aqueous phase;
adding 500uL of ethyl acetate into the lower aqueous phase, uniformly mixing by vortex, centrifuging for 3min at 10000rpm under the condition of 4 ℃, and combining the upper organic phase with the upper organic phase obtained in the previous step;
and blowing the combined upper organic phase by using nitrogen, re-dissolving by using acetonitrile/isopropanol (1: 1), filling into a sample bottle, and waiting for detection on a machine.
The signal-to-noise ratio of the arachidonic acid-like substances extracted by the extraction methods of examples 1-3 is shown in Table 1. The extraction rate of arachidonic acid-like substances extracted by the extraction methods of examples 1-3 is shown in Table 2. The extraction rate is calculated by adopting a method for calculating the standard recovery rate, namely, a 20mM standard substance is added into a sample to be detected, and the sample is extracted and then detected, wherein the calculation formula is as follows: (sample peak area with standard-sample peak area without standard)/peak area of standard was detected separately.
TABLE 1 comparison of signal-to-noise ratios of arachidonic acid-like substances extracted by the extraction methods of examples 1-3
Figure BDA0002240856280000091
Figure BDA0002240856280000101
TABLE 2 examples 1-3 extraction methods for extracting arachidonic acid-like substances
Figure BDA0002240856280000102
Figure BDA0002240856280000111
According to the invention, various arachidonic acid compounds are detected simultaneously, the extraction rate of arachidonic acid substances is higher by combining ethyl acetate and MTBE than by extracting with a single solvent, the signal-to-noise ratio during detection is obviously improved, and the detection sensitivity of the substances is obviously improved by the method.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.

Claims (3)

1. A method for detecting an arachidonic acid-like substance, which is characterized by comprising the following steps: comprises the steps of (a) preparing a mixture of a plurality of raw materials,
adding 300 parts of water containing 0.005% BHT into 100 parts of samples by volume;
adding 500 parts of methyl tert-butyl ether, centrifuging at 4 deg.C and 10000rpm for 3min, transferring the upper organic phase, and retaining the lower aqueous phase;
adding 500 parts of ethyl acetate into the lower aqueous phase, centrifuging at 4 ℃ and 10000rpm for 3min, and combining the upper organic phase with the upper organic phase obtained in the previous step;
blowing the combined upper organic phase by nitrogen, re-dissolving by using an acetonitrile-isopropanol solution, and detecting by using a machine;
wherein, by volume ratio, acetonitrile: 1-isopropyl alcohol: 1;
in the detection process, 2-chlorophenylalanine is used as an internal standard instead of a solvent, the collection condition of an actual sample is reflected by the peak area and retention time of the 2-chlorophenylalanine, and the concentration of the 2-chlorophenylalanine is 1 mu g/mL;
in the detection process, a mixed standard sample of 4, 4' -methylenebis (2-chloroaniline), p-anisidine, L-tyrosine methyl ester, 3-chloroaniline, 2, 4-dimethylquinoline, sulfapyridine, atrazine, sulfadoxine, DL-leucine, N-benzoyl-L-tyrosine ethyl ester, 6-phenyl-2-thiouracil, N- (o-toluoyl) glycine, 2-methyl-5-nitroimidazole-1-ethanol, glycyrrhetinic acid, flavanone, epsilon-caprolactone and 2-aminopyridine is used as a quality control material, at least two needles of quality control materials are used for each detection, analyzing the state of a detection instrument according to the overlapping condition of the spectrograms, wherein the content of the 4, 4' -methylene-bis (2-chloroaniline) is as follows by mass ratio: p-anisidine: l-tyrosine methyl ester: 3-chloroaniline: 2, 4-dimethylquinoline: sulfapyridine: atrazine: sulfadoxine: DL-leucine: N-benzoyl-L-tyrosine ethyl ester: 6-phenyl-2-thiouracil: n- (o-toluoyl) glycine: 2-methyl-5-nitroimidazole-1-ethanol: glycyrrhetinic acid: flavanone: epsilon-caprolactone: 2-aminopyridine ═ 1: 0.5: 0.5: 2: 1: 0.4: 0.1: 0.1: 0.2: 0.5: 0.5: 1: 1: 0.1: 0.5: 2: 0.2.
2. the method for detecting an arachidonic acid-like substance according to claim 1, wherein: the sample comprises a plasma sample.
3. The method for detecting an arachidonic acid-like substance according to claim 1, wherein: the concentration of the 4, 4' -methylene-bis (2-chloroaniline) is 1 mu g/mL, the concentration of p-anisidine is 0.5 mu g/mL, the concentration of L-tyrosine methyl ester is 0.5 mu g/mL, the concentration of 3-chloroaniline is 2 mu g/mL, the concentration of 2, 4-dimethylquinoline is 1 mu g/mL, the concentration of sulfapyridine is 0.4 mu g/mL, the concentration of atrazine is 0.1 mu g/mL, the concentration of sulfadoxine is 0.1 mu g/mL, the concentration of DL-leucine is 0.2 mu g/mL, the concentration of N-benzoyl-L-tyrosine ethyl ester is 0.5 mu g/mL, the concentration of 6-phenyl-2-thiouracil is 0.5 mu g/mL, the concentration of N- (o-toluoyl) glycine is 1 mu g/mL, and the concentration of p-anisidine is 0.5 mu g/mL, The concentration of 2-methyl-5-nitroimidazole-1-ethanol is 1 mug/mL, the concentration of glycyrrhetinic acid is 0.1 mug/mL, the concentration of flavanone is 0.5 mug/mL, the concentration of epsilon-caprolactone is 2 mug/mL, and the concentration of 2-aminopyridine is 0.2 mug/mL.
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