CN113063838A - Lipid carbon-carbon double bond isomer mass spectrum imaging method based on visible light catalysis and application thereof - Google Patents
Lipid carbon-carbon double bond isomer mass spectrum imaging method based on visible light catalysis and application thereof Download PDFInfo
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Abstract
The invention provides a visible light catalysis-based lipid carbon-carbon double bond isomer mass spectrometry imaging method and application thereof, belonging to the technical field of mass spectrometry detection. The invention sprays a novel derivatization reagent on the surface of the tissue slice, then carries out tissue in-situ derivatization reaction under the catalysis of visible light, and further adopts MALDI mass spectrometry imaging technology to carry out mass spectrometry imaging analysis on the derivatized tissue slice, thereby realizing in-situ visual characterization of lipid C ═ C double bond isomer in biological tissue, and having good value of practical popularization and application.
Description
Technical Field
The invention belongs to the technical field of mass spectrometry detection, and particularly relates to a visible light catalysis-based lipid carbon-carbon double bond isomer mass spectrometry imaging method and application thereof.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
Lipid components such as fatty acids and phospholipids play an essential role in constructing cell biological membranes, transmitting biological signals, regulating cell energy metabolism, and the like. There is a growing body of evidence that changes in lipid composition in the body are closely related to the development of various diseases such as tumors, alzheimer's disease, and senile dementia. The method adopts Mass Spectrometry Imaging (MSI) to carry out in-situ visual detection on lipid components in biological tissues, can master the spatial variation characteristics of lipid molecules under physiological and pathological conditions of organisms, and can improve the understanding of the biological action of the lipid molecules. It is noted that the fatty acid chains of unsaturated lipid molecules usually have carbon-carbon double bonds (C ═ C), which results in a variety of different C ═ C double bond lipid isomers in the organism, and the role of different C ═ C double bond lipid isomers in the body is often different.
The mass spectrometry imaging technology can be used for scanning and detecting lipid molecules in a tissue sample point by point according to spatial positions to obtain a data array of the relationship between the intensity and the position of the lipid ions, and then, the mass spectrometry imaging software is used for carrying out visual reconstruction on different lipid ions according to the intensities and the spatial positions of the different lipid ions to finally realize the imaging analysis of various lipid molecules. However, for different C ═ C isomers of lipids in biological tissues, it is difficult to perform visual analysis directly on the different C ═ C isomers using mass spectrometry imaging techniques, since they have the same value of mass-to-charge ratio (m/z).
In order to solve this problem, researchers have used ultraviolet-catalyzed pueran oa-buchi (pb) derivatization to localize the C ═ C double bond position in lipids, and then analyzed the characteristic fragment ions of the C ═ C isomers of different lipids using mass-spectrometry collision-induced dissociation (CID) -MS/MS. Further, the distribution characteristics of fragment ions of different lipid C-C isomers in different regions of tissues are extracted in a targeted mode, so that mass spectrum imaging analysis of the different lipid C-C isomers can be realized. However, the inventors have found that carrying out the Patern oa (PB) derivatization directly on tissue sections is susceptible to environmental influences and requires very stringent reaction conditions. Furthermore, the derivatization reaction of Patern oa (PB) needs to be carried out under UV radiation, which not only causes side reactions but also can be harmful to the health of the experimenter.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a MALDI mass spectrometry imaging method of lipid C ═ C double bond isomer based on visible light catalytic derivatization and application thereof. A novel derivatization reagent is sprayed on the surface of the tissue slice, then tissue in-situ derivatization reaction is carried out under the catalysis of visible light, and mass spectrometry imaging analysis is further carried out on the derivatized tissue slice by adopting a MALDI mass spectrometry imaging technology, so that in-situ visual characterization of lipid C-C double bond isomers in biological tissues is realized.
In order to achieve the technical purpose, the technical scheme adopted by the invention is as follows:
in a first aspect of the invention, there is provided the use of 3-benzoylpyridine in MALDI mass spectrometry imaging based on visible light catalysed derivatisation of a C ═ C double bond isomer of a lipid.
Wherein, in the application, the 3-benzoylpyridine is used as a derivatization reagent.
In a second aspect of the present invention, there is provided a MALDI mass spectrometry imaging method for a C ═ C double bond isomer of a lipid based on visible light catalytic derivatization, the method at least comprising:
spraying a derivatization reagent on the surface of a sample to be tested, catalyzing the derivatization reaction by adopting visible light irradiation, and obtaining a derivatization product of unsaturated lipid after the reaction is finished;
and spraying a MALDI matrix on the sample to be detected after the derivatization treatment, and then carrying out MALDI mass spectrometry imaging analysis.
Wherein the derivatization reagent is 3-benzoylpyridine, and the structural formula of the derivatization reagent is shown as the formula (I):
in a third aspect of the invention, the application of the MALDI mass spectrometry imaging method for the C ═ C double bond isomer of lipid based on visible light catalytic derivatization in-situ lipid analysis is provided.
The beneficial technical effects of one or more technical schemes are as follows:
(1) the catalytic light source used in the technical scheme is 405nm visible light, and the harm to an experiment operator is small.
(2) The derivatization reagent used in the technical scheme is 3-benzoylpyridine, and the derivatization reagent is simple, has mild reaction conditions and is suitable for in-situ derivatization of unsaturated lipid on the surface of tissue.
(3) In the technical scheme, a pyridine group containing tertiary amine can be introduced into a lipid structure through derivatization reaction, so that the ionization efficiency of mass spectrum is improved, and MALDI mass spectrum imaging detection of lipids such as unsaturated fatty acid, unsaturated phosphatidylcholine and the like can be realized.
(4) In the technical scheme, through derivatization reaction, a pyridine group containing tertiary amine can be introduced into an unsaturated fatty acid structure, and the fatty acid has a carboxylic acid group, so that MALDI mass spectrometry imaging detection of the derivatized fatty acid can be carried out in a positive ion detection mode and a negative ion detection mode, and the method has good practical popularization and application values.
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The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a reaction scheme of unsaturated lipids with 3-benzoylpyridine;
FIG. 2 is a schematic diagram of the CID-MS/MS fragmentation positions of the derivatives produced after reaction of unsaturated lipids with 3-benzoylpyridine;
FIG. 3 is a CID-MS/MS spectrum of a derivative generated by three double bond position isomers of fatty acid C18:1 in example 1 of the present invention;
FIG. 4 is the CID-MS/MS spectrum and the mass spectrum image of two double bond position isomer derivatives of Phosphatidylcholine (PC) C34:1 in example 2 of the present invention.
FIG. 5 is the CID-MS/MS spectrum and the mass spectrum image of two double bond position isomer derivatives of Phosphatidylcholine (PC) C36:1 in example 3 of the present invention.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise. It is to be understood that the scope of the invention is not to be limited to the specific embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention.
As mentioned above, carrying out the Patern oa (PB) derivatization directly on tissue sections is susceptible to environmental influences and requires very stringent reaction conditions. Furthermore, the derivatization reaction of Patern oa (PB) needs to be carried out under UV radiation, which not only causes side reactions but also can be harmful to the health of the experimenter.
In view of the above, in one embodiment of the present invention, there is provided the use of 3-benzoylpyridine (CAS: 5424-19-1) for MALDI mass spectrometry imaging of C ═ C double bond isomers of lipids based on visible light catalyzed derivatization.
In still another embodiment of the present invention, in said use, said 3-benzoylpyridine is used as a derivatizing agent.
In another embodiment of the present invention, a MALDI mass spectrometry imaging method based on visible light catalyzed derivatization of C ═ C double bond isomers of lipids is provided, the method at least comprising:
spraying a derivatization reagent on the surface of a sample to be tested, and catalyzing a derivatization reaction by adopting visible light irradiation to obtain a derivatization product of unsaturated lipid after the reaction is finished;
and spraying a MALDI matrix on the sample to be detected after the derivatization treatment, and then carrying out MALDI mass spectrometry imaging analysis.
Wherein, the sample to be detected can be a tissue slice; further, the tissue section may be animal tissue section, such as rat brain tissue section. In one embodiment of the present invention, the tissue section is specifically prepared by the following steps: and (3) preparing a frozen section of the biological tissue, transferring the frozen section to an ITO-indium tin oxide conductive glass slide, and drying in vacuum to obtain the biological tissue.
In another embodiment of the present invention, the derivatizing agent is 3-benzoylpyridine having a structural formula as shown in formula (I):
in yet another embodiment of the present invention, the derivatizing agent is a solution of 3-benzoylpyridine, the concentration of the 3-benzoylpyridine solution being 2-20mM, preferably 10 mM.
In another embodiment of the invention, the solvent used for the 3-benzoylpyridine solution is a mixed solution of water and acetonitrile; further, the volume ratio of water to acetonitrile is 95:5 to 5:95, preferably the volume ratio of water to acetonitrile is 50: 50. The concentration of the 3-benzoylpyridine solution and the dosage proportion of the solvent are controlled, so that the subsequent derivatization reaction efficiency is improved.
In yet another embodiment of the present invention, the temperature of the spray of the derivatizing agent, 3-benzoylpyridine, is controlled to be 40-80 deg.C, preferably 70 deg.C.
In yet another embodiment of the present invention, the derivatizing agent, 3-benzoylpyridine, is spray injected at a flow rate of 0.01-0.05mL/min, preferably 0.03 mL/min.
In yet another embodiment of the present invention, the derivatizing agent, 3-benzoylpyridine, is sprayed onto the surface of the sample at a density of 50-150nM/cm2Preferably 100nM/cm2。
The derivatization level of the unsaturated lipid on the tissue surface of the sample to be detected is improved by controlling and optimizing the spraying temperature, the spraying injection flow rate and the spraying density of the derivatization reagent 3-benzoylpyridine.
In still another embodiment of the present invention, the visible light wavelength is 405-520nm, preferably 405nm, 450nm and 520nm, and more preferably 405 nm. At this visible wavelength, the catalytic efficiency is higher.
In another embodiment of the present invention, the irradiation time of the sample surface with visible light is 1min to 60min, preferably 30 min.
In still another embodiment of the present invention, the MALDI spray matrix used is any one of α -nitrile-4-hydroxycinnamic acid, 9-aminoacridine, and 1, 5-diaminonaphthalene, preferably 1, 5-diaminonaphthalene.
In another embodiment of the present invention, MALDI-TOF/TOF mass spectrometry is used to perform scanning analysis on the derivatized sample, wherein the scanning mode is an MS/MS scanning mode.
In yet another embodiment of the present invention, the ion source voltage 1 and ion source voltage 2 are set to 20kV and 19.45kV, respectively, and the lens voltage is set to 18.3kV, when MALDI-MS/MS analysis is performed on the derivatized sample.
In another embodiment of the present invention, there is provided an application of the MALDI mass spectrometry imaging method for lipid C ═ C double bond isomers based on visible light catalytic derivatization in lipid in situ analysis.
Wherein the lipid is unsaturated lipid, and further comprises unsaturated fatty acid and unsaturated phospholipid.
The invention is further illustrated by the following examples, which are not to be construed as limiting the invention thereto. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
Example 1: visible light catalytic derivatization mass spectrometry imaging analysis of fatty acid C ═ C double bond isomer on glass slide
(1) 10mg of 6Z-Fatty Acid (FA) -C18:1, 9Z-FA-C18:1, 11Z-FA-C18:1 control, respectively, were precisely weighed into a 10mL volumetric flask, and 10mL of acetonitrile: vortex and mix the water (50:50, v/v) solution evenly, and obtain 6Z-FA-C18:1, 9Z-FA-C18:1, 11Z-FA-C18:1 solution after ultrasonic treatment for 3 minutes;
(2) respectively passing the above solutions of different fatty acid isomers with C ═ C double bond through HTX TM-SprayerTMThe fatty acid control substance is sprayed on the ITO-indium tin oxide conductive glass slide by the sprayer, and the density of the fatty acid control substance on the ITO-indium tin oxide conductive glass slide is 4.7nmol/cm2；
(3) 18.3mg of 3-benzoylpyridine was precisely weighed into a 10mL volumetric flask, and 10mL of acetonitrile was added: vortex and mix the water (50:50, v/v) solution evenly, and obtain 10 mmol/L3-benzoylpyridine solution after 3 minutes of ultrasonic treatment;
(4) passing the 3-benzoylpyridine solution through HTX TM-SprayerTMThe spraying instrument is sprayed on an ITO-indium tin oxide conductive glass slide with different fatty acid C ═ C double bond isomer reference substances on the surface, and the spraying density of the 3-benzoylpyridine is 100nM/cm2。
(5) Placing the slide coated with the fatty acid C ═ C double bond isomer reference substance and 3-benzoylpyridine in a closed foam box with the length, width and height of 30cm, 10cm and 15cm respectively, and irradiating for 30 minutes under the visible light of 405nm and 200 mW;
(6) precisely weigh 25mg of 1, 5-diaminonaphthalene into a 10mL volumetric flask, add 10mL of acetonitrile: mixing the solution of water (50:50, v/v) by vortex, and performing ultrasonic treatment for 10 minutes to obtain a 1, 5-diaminonaphthalene solution;
(7) using HTX TM-SprayerTMThe spraying instrument sprays the 1, 5-diaminonaphthalene solution on the glass slide after photocatalysis, and the spraying conditions are as follows: the spraying speed is 0.05mL/min, the distance between the spraying tracks is 3mm, and the cycle times are 12 times;
(8) and (3) carrying out full-scan mass spectrometry analysis on the sample after the matrix is sprayed by using a Brukrapiflex MALDI-TOF/TOF type mass spectrometer, and extracting a mass spectrometry image of the FA-C18:1 after derivatization by using SCiLS Lab 2018b data processing software, wherein the extracted ion is + m/z 466.3.
(9) In-situ secondary MS/MS analysis is carried out on the fragment carriers respectively coated with 6Z-FA-C18:1, 9Z-FA-C18:1 and 11Z-FA-C18:1 on the surfaces by using a Brookrafiflex MALDI-TOF/TOF type mass spectrometer, the secondary analysis parent ions are + m/Z466.3 ions, and characteristic secondary mass spectrum profiles of 6Z-FA-C18:1, 9Z-FA-C18:1 and 11Z-FA-C18:1 are obtained, and are shown in figure 3.
(10) And (3) respectively and targetedly extracting mass spectrum imaging images of 6Z-FA-C18:1, 9Z-FA-C18:1 and 11Z-FA-C18:1 secondary fragment ions on the glass slide by using SCiLS Lab 2018b data processing software.
Example 2: derivatization mass spectrometry of two double bond position isomers of Phosphatidylcholine (PC) -C34:1 in rat brain
(1) Taking fresh rat brain tissue, and utilizing a CryoStar microtome of a thermoelectric company to prepare frozen sections of coronal planes and horizontal planes of the brain tissue with the thickness of 12 mu m;
(2) frozen sections of the coronal plane and the horizontal plane of the brain tissue are transferred onto an ITO-indium tin oxide conductive glass slide and dried for 15 minutes in vacuum.
(3) 18.3mg of 3-benzoylpyridine was precisely weighed into a 10mL volumetric flask, and 10mL of acetonitrile was added: vortex and mix the water (50:50, v/v) solution evenly, and obtain 10 mmol/L3-benzoylpyridine solution after 3 minutes of ultrasonic treatment;
(4) passing the 3-benzoylpyridine solution through HTX TM-SprayerTMSpraying the 3-benzoylpyridine onto slices of coronal and horizontal planes of brain tissue at a density of 100nM/cm2。
(5) Placing the brain tissue slice sprayed with the 3-benzoylpyridine in a closed foam box with the length, width and height of 30cm, 10cm and 15cm respectively, and irradiating for 30 minutes at 405nm under 200mW visible light;
(6) precisely weigh 25mg of 1, 5-diaminonaphthalene into a 10mL volumetric flask, add 10mL of acetonitrile: mixing the solution of water (50:50, v/v) by vortex, and performing ultrasonic treatment for 10 minutes to obtain a 1, 5-diaminonaphthalene solution;
(7) using HTX TM-SprayerTMThe spraying instrument sprays the 1, 5-diaminonaphthalene solution on the glass slide after photocatalysis, and the spraying conditions are as follows: the spraying speed is 0.05mL/min,the distance between the spraying tracks is 3mm, and the cycle times are 12 times;
(8) and (3) carrying out full-scan mass spectrometry imaging analysis on the brain tissue section after the matrix is sprayed by using a Brukrapiflex MALDI-TOF/TOF type mass spectrometer imager, and extracting a mass spectrometry imaging chart of the derivatized PC-C34:1 by using SCiLS Lab 2018b data processing software, wherein the extracted ion is + m/z 943.6.
(9) And (3) carrying out in-situ secondary MS/MS analysis on the brain tissue section by using a Brookrafiflex MALDI-TOF/TOF type mass spectrum imager, wherein secondary analysis parent ions are derivatized PC-C34:1(+ m/z 943.6) ions, and an obtained characteristic secondary mass spectrum profile is shown in an attached figure 4.
(10) Analysis of the PC-C34:1 secondary mass spectrum after derivatization revealed that two C ═ C isomers, PC 16:0_18:1(Δ 9) and PC 16:0_18:1(Δ 11), were present in the brain tissue for PC-C34:1, the characteristic secondary fragment ion for PC 16:0_18:1(Δ 9) was + m/z 650.4, and the characteristic secondary fragment ion for PC 16:0_18:1(Δ 11) was + m/z 678.6.
(11) The mass spectrum imaging of the secondary fragment ions of PC 16: 0-18: 1 (delta 9) and PC 16: 0-18: 1 (delta 11) in brain tissue was targeted by SCiLS Lab 2018b data processing software, see FIG. 4.
Example 3: derivatization mass spectrometry of two double bond position isomers of Phosphatidylcholine (PC) -C36:1 in rat brain
(1) Taking fresh rat brain tissue, and utilizing a CryoStar microtome of a thermoelectric company to prepare frozen sections of coronal planes and horizontal planes of the brain tissue with the thickness of 12 mu m;
(2) frozen sections of the coronal plane and the horizontal plane of the brain tissue are transferred onto an ITO-indium tin oxide conductive glass slide and dried for 15 minutes in vacuum.
(3) 18.3mg of 3-benzoylpyridine was precisely weighed into a 10mL volumetric flask, and 10mL of acetonitrile was added: vortex and mix the water (50:50, v/v) solution evenly, and obtain 10 mmol/L3-benzoylpyridine solution after 3 minutes of ultrasonic treatment;
(4) passing the 3-benzoylpyridine solution through HTX TM-SprayerTMSpraying the 3-benzoylpyridine onto slices of coronal and horizontal planes of brain tissue at a density of 100nM/cm2。
(5) Placing the brain tissue slice sprayed with the 3-benzoylpyridine in a closed foam box with the length, width and height of 30cm, 10cm and 15cm respectively, and irradiating for 30 minutes at 405nm under 200mW visible light;
(6) precisely weigh 25mg of 1, 5-diaminonaphthalene into a 10mL volumetric flask, add 10mL of acetonitrile: mixing the solution of water (50:50, v/v) by vortex, and performing ultrasonic treatment for 10 minutes to obtain a 1, 5-diaminonaphthalene solution;
(7) using HTX TM-SprayerTMThe spraying instrument sprays the 1, 5-diaminonaphthalene solution on the glass slide after photocatalysis, and the spraying conditions are as follows: the spraying speed is 0.05mL/min, the distance between the spraying tracks is 3mm, and the cycle times are 12 times;
(8) and (3) carrying out full-scan mass spectrometry imaging analysis on the brain tissue section after the matrix is sprayed by using a Brukrapiflex MALDI-TOF/TOF type mass spectrometer imager, and extracting a mass spectrometry imaging chart of the derivatized PC-C36:1 by using SCiLS Lab 2018b data processing software, wherein the extracted ion is + m/z 971.6.
(9) And (3) carrying out in-situ secondary MS/MS analysis on the brain tissue section by using a Brookrafiflex MALDI-TOF/TOF type mass spectrum imager, wherein secondary analysis parent ions are derivatized PC-C36:1(+ m/z 971.6) ions, and an obtained characteristic secondary mass spectrum profile is shown in an attached figure 5.
(10) Analysis of the PC-C36:1 secondary mass spectrum after derivatization revealed that two C ═ C isomers, PC 18:0_18:1(Δ 9) and PC 18:0_18:1(Δ 11), were present in the brain tissue for PC-C36:1, the characteristic secondary fragment ion for PC 18:0_18:1(Δ 9) was + m/z 678.5, and the characteristic secondary fragment ion for PC 18:0_18:1(Δ 11) was + m/z 706.5.
(11) Mass spectrum imaging of secondary fragment ions of PC 18: 0-18: 1 (delta 9) and PC 18: 0-18: 1 (delta 11) in brain tissue was targeted by SCiLS Lab 2018b data processing software, see FIG. 5.
It should be noted that the above examples are only used to illustrate the technical solutions of the present invention and not to limit them. Although the present invention has been described in detail with reference to the examples given, those skilled in the art can modify the technical solution of the present invention as needed or equivalent substitutions without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
- The application of 3-benzoylpyridine in MALDI mass spectrometry imaging of C ═ C double bond isomer of lipid based on visible light catalytic derivatization.
- 2. The use according to claim 1, wherein the 3-benzoylpyridine is used as derivatizing agent.
- 3. MALDI mass spectrometry imaging method of lipid C ═ C double bond isomers based on visible light catalytic derivatization, characterized in that it comprises at least:spraying a derivatization reagent on the surface of a sample to be tested, and irradiating visible light to catalyze a derivatization reaction;and spraying a MALDI matrix on the sample to be detected after the derivatization treatment, and then carrying out MALDI mass spectrometry imaging analysis.
- 4. The method of claim 3, wherein the sample to be tested is a tissue section; preferably, the tissue slices are animal tissue slices.
- 5. The method of claim 3, wherein the derivatizing agent is 3-benzoylpyridine having the formula (I):
preferably, the derivatization reagent is a 3-benzoylpyridine solution, and the concentration of the 3-benzoylpyridine solution is 2-20mM, preferably 10 mM;preferably, the solvent selected for the 3-benzoylpyridine solution is a mixed solution of water and acetonitrile; it is further preferred that the volume ratio of water to acetonitrile is 95:5 to 5:95, and it is further preferred that the volume ratio of water to acetonitrile is 50: 50. - 6. The method of claim 5,the spraying temperature of the derivatization reagent 3-benzoylpyridine is controlled to be 40-80 ℃, and preferably 70 ℃;the spraying injection flow rate of the derivatization reagent 3-benzoylpyridine is 0.01-0.05mL/min, preferably 0.03 mL/min;the spraying density of the derivatization reagent 3-benzoylpyridine on the surface of the sample is 50-150nM/cm2Preferably 100nM/cm2。
- 7. The method according to claim 3, wherein the visible light wavelength is 405-520nm, preferably 405nm, 450nm and 520nm, more preferably 405 nm;preferably, the irradiation time of the visible light wavelength on the sample surface is 1min to 60min, and more preferably 30 min.
- 8. A method according to claim 3, wherein the MALDI spray matrix used is any one of α -nitrile-4-hydroxycinnamic acid, 9-aminoacridine, 1, 5-diaminonaphthalene, preferably 1, 5-diaminonaphthalene.
- 9. The method of claim 3, wherein MALDI-TOF/TOF mass spectrometry is used for scanning analysis of the derivatized sample, and the scanning mode is MS/MS scanning mode.
- 10. Use of the MALDI mass spectrometry imaging method based on visible light catalysed derivatisation of a lipid C ═ C double bond isomers according to any of claims 3 to 9 in lipid in situ analysis;preferably, the lipid is an unsaturated lipid, further comprising an unsaturated fatty acid and an unsaturated phospholipid.
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