CN107632095A - A kind of detection method of crop glycolipid and phosphatide - Google Patents
A kind of detection method of crop glycolipid and phosphatide Download PDFInfo
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- CN107632095A CN107632095A CN201710847156.7A CN201710847156A CN107632095A CN 107632095 A CN107632095 A CN 107632095A CN 201710847156 A CN201710847156 A CN 201710847156A CN 107632095 A CN107632095 A CN 107632095A
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- glycolipid
- phosphatide
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- 229930186217 Glycolipid Natural products 0.000 title claims abstract description 52
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000001514 detection method Methods 0.000 title claims abstract description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000012071 phase Substances 0.000 claims abstract description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011259 mixed solution Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- 239000012488 sample solution Substances 0.000 claims abstract description 9
- 238000003859 hyphenated technique Methods 0.000 claims abstract description 4
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- 239000004753 textile Substances 0.000 claims abstract description 3
- 150000002500 ions Chemical class 0.000 claims description 28
- 239000000523 sample Substances 0.000 claims description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 235000019257 ammonium acetate Nutrition 0.000 claims description 10
- KDYAPQVYJXUQNY-OPHDRXFHSA-N 1,2-di-(alpha-linolenoyl)-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](OC[C@@H](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)O[C@@H]1CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KDYAPQVYJXUQNY-OPHDRXFHSA-N 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 7
- 239000005695 Ammonium acetate Substances 0.000 claims description 7
- 229940043376 ammonium acetate Drugs 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical group [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 3
- 238000000889 atomisation Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 description 9
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- -1 sterol lipid Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 240000008790 Musa x paradisiaca Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 3
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 3
- 235000009429 Gossypium barbadense Nutrition 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 3
- 238000004808 supercritical fluid chromatography Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 235000018322 upland cotton Nutrition 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- QZXMUPATKGLZAP-DXLAUQRQSA-N [(2S)-1-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](OC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)O[C@@H]1CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QZXMUPATKGLZAP-DXLAUQRQSA-N 0.000 description 2
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000006353 environmental stress Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002313 glycerolipids Chemical class 0.000 description 2
- 230000002949 hemolytic effect Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
- 150000003905 phosphatidylinositols Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003408 sphingolipids Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 1
- WRGQSWVCFNIUNZ-GDCKJWNLSA-N 1-oleoyl-sn-glycerol 3-phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O WRGQSWVCFNIUNZ-GDCKJWNLSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 241000234295 Musa Species 0.000 description 1
- 244000131316 Panax pseudoginseng Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 102000011420 Phospholipase D Human genes 0.000 description 1
- 108090000553 Phospholipase D Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 210000003763 chloroplast Anatomy 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002327 glycerophospholipids Chemical class 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
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- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229940067626 phosphatidylinositols Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 125000000830 polyketide group Chemical group 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002541 precursor ion scan Methods 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 150000003135 prenol lipids Chemical class 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003313 saccharo lipids Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004724 ultra fast liquid chromatography Methods 0.000 description 1
Landscapes
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The present invention relates to the detection method of a kind of crop glycolipid and phosphatide.The detection method is analyzed sample solution using efficient liquid phase with mass spectrometric hyphenated technique；Wherein, mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile acid in positive ion detection pattern, and the volume ratio of methanol, acetonitrile and water is 42.5 in the mixed solution:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile acid；Mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile base in anionic textiles pattern, and the volume ratio of methanol, acetonitrile and water is 42.5 in the mixed solution:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile base.Detection method provided by the invention can realize the high accuracy of crop glycolipid and phosphatide and highly sensitive qualitative, quantitative, and mass-to-charge ratio can be accurate to after decimal point the 3rd；The detection limit to crop content of phospholipid can be reduced simultaneously, it is quantitative more accurate.
Description
Technical field
The invention belongs to glycolipid and phosphatide detection field, and in particular to a kind of detection method of crop glycolipid and phosphatide.
Background technology
Lipid is generally divided into following eight major class：Fatty acid（fatty acids）, glycerolipid（glycerolipids）、
Glycerophosphatide class（glycerophospholipids）, sphingolipid（sphingolipids）, sterol lipid（sterol
lipids）, pregnenolone lipid（prenollipids）, glycolipid class（saccharolipids）, more polyethylene kinds
（polyketides）.Glycolipid is the compound that sugar is connected by its hemiacetal hydroxyl with glycosidic bond with lipid.In view of lipid part
Difference, glycolipid can be divided into glycosyl sphingolipid, glyceroglycolipid and the glycolipid as derived from steroids, and wherein lipid moieties are glyceride
Title glyceroglycolipid, it includes thio isorhamnose monoacylglycerol（SQMG）, thio isorhamnose diglyceride（SQDG）, it is single
Galactolipin diacylglycerol（MGDG, Monogalaetosyldiacylglycerol）, Digalactosyl diacylglycerol（DGDG,
Digalactosyldiacylglycerol）.Glyceroglycolipid is primarily present in plant kingdom and microorganism, is bacterial protoplast
The main constituents of film, plant chloroplast class cyst membrane, participate in the identification activity of cell membrane.Glycerophosphatide molecule by 1 phosphoric acid,
4 parts such as 1 glycerol backbone, 1 hydrophilic head R and 1 hydrophobic tail composition.Hydrophilic head R is the polarity of phospholipid molecule
End, can be choline, monoethanolamine, inositol, serine, glycerine, form different types of glycerophosphatide compound：Phosphatidic acid
（Phosphoric acid, PA）, lysophosphatidic acid（LPA）, phosphatidyl choline（Phosphatidylcholine, PC）, haemolysis
Property phosphatidyl choline（Lysophosphatidylcholine, LPC）, phosphatidyl-ethanolamine
（Lysophosphatidylethanolamine, PE）, hemolytic phosphatidyl-ethanolamine（LPE）, phosphatidylinositols
（Phosphatidylinositol, PI）, LPI（LPI）, phosphatidylserine
（Phosphatidylserine, PS）, hemolytic phosphatidylserine（LPS）, phosphatidyl glycerol
（Phosphatidylglycerol, PG）, lysophosphatidyl glycerol（Lysophosphatidylglycerol, LPG）.Hydrophobic tail
Portion is the non-polar end of phospholipid molecule, mainly contains different carbon numbers by one or two（n= 14-22）With different degrees of unsaturation
（n=0-6）Fatty acid chain form.
Rice, cotton and banana etc. are extremely important industrial crops, development and response environment stress to these crops
Mechanism Study, there is highly important theory value and extensive realistic meaning.Existing result of study points out the phosphorus in plant
Fat and its relevant metabolic pathway participate in the response a variety of environment stresses of plant.Therefore by improving phospholipid level internal in crop
Qualitative and quantitative detection level is studied, and is advantageous to the functional study of crop phosphatide, so as to improve crop breeding and Improvement in Shape tool
There is important actual application value.
Phytoglycolipid and phosphatide detection method are a lot, including thin-layer chromatography（Thin-Layer Chromatography,
TLC）Method, gas-chromatography（Gas chromatography, GC）Method, Capillary Electrophoresis（Capillary
Electrophoresis, CE）Method, supercritical fluid chromatography（Supercritical fluid chromatography, SFC）
Method, high performance liquid chromatography（High performance liquid chromatography, HPLC）Method and various mass spectrums（Mass
Spectrum, MS）Technology, and chromatograph-mass spectrometer coupling technology.But detection spirit of these technologies to glycolipid and phosphatide cpd
Sensitivity is unsatisfactory, and qualitative ability is not also strong.
Therefore, the detection method of the crop glycolipid and phosphatide of developing a kind of high detection sensitivity has important Research Significance
And application value.
The content of the invention
It is an object of the invention to overcome, phytoglycolipid in the prior art and phosphatide detection method sensitivity be low, qualitative ability
A kind of the defects of not strong, there is provided detection method of crop glycolipid and phosphatide.The crop glycolipid of offer of the present invention and the inspection of phosphatide
Survey method can realize the high accuracy of crop glycolipid and phosphatide and highly sensitive qualitative detection, while can reduce to crop sugar
The detection limit of fat and content of phospholipid, it is quantitative more accurate.
For achieving the above object, the present invention adopts the following technical scheme that：
A kind of detection method of crop glycolipid and phosphatide, the detection method comprise the following steps：
S1：Add after chloroform is vibrated to abundant dissolving and filter into the crop sample of glycolipid containing crop and phosphatide；Then in adding
Mark mixed liquor, methanol and ammonium acetate obtain sample solution；
S2：Sample solution in S1 is analyzed with mass spectrometric hyphenated technique using efficient liquid phase；
Wherein, positive ion detection pattern：Mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile acid, and the mixing is molten
The volume ratio of methanol, acetonitrile and water is 42.5 in liquid:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile acid；
Anionic textiles pattern：Mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile base, first in the mixed solution
The volume ratio of alcohol, acetonitrile and water is 42.5:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile base.
Phosphatide and glycolipid fractions kind more than totally one hundred, species is different, and its chain length and saturation degree are also different.In order to effective whole
Elution, and separate, it is necessary to select suitable mobile phase ratio.Isopropanol, methanol and acetonitrile have preferable polarity, this hair
Bright inventor, which studies, to be found, is 42.5 when selecting volume ratio:42.5:The mixed solution of 15 methanol, acetonitrile and water, and add
When the volatile base such as the volatile acids such as formic acid, acetic acid or ammonium formate, ammonium acetate improves sample ionization, it can be washed by liquid phase gradient
The de- elution and separation for realizing most of glycolipids and phosphatide in crop.
Preferably, volatile acid is formic acid or acetic acid in mobile phase A and Mobile phase B, the volume fraction of the volatile acid
For 0.1%.Now by detecting the feature such as structure of glycolipid and phosphatide in sample positive ion mode can be selected to be detected.
Preferably, volatile base is ammonium formate or ammonium acetate in mobile phase A and Mobile phase B, the volume of the volatile base
Fraction is 0.1%.Now by detecting the feature such as structure of glycolipid and phosphatide in sample negative ion mode can be selected to be examined
Survey.
Preferably, liquid phase condition of gradient elution is in S2：0 ~ 10 minute, 40% Mobile phase B；10 ~ 35 minutes, 40% ~ 65% stream
Dynamic phase B；35 ~ 42 minutes, 0% Mobile phase B.
Preferably, chromatographic column is PhenomenexKinetex C18 in S2.
Preferably, flow rate of mobile phase is 300 μ L/min in S2；Column temperature is 40 DEG C；Sample size is 8 μ L.
Preferably, mass spectrometer system is AB SCIEX TripleTOF 5600+ mass spectrometer systems in S2, the mass spectrographic ginseng
Number is arranged to：Atomization gas：55 psi；Aid in gas：55 psi；Gas curtain gas：35 psi；Ion source temperature：300℃；Voltage：-
4.5KV/5.5KV.Collision voltage（CE）, positive ion mode, PE and LysoPE ,+28V；PC and LysoPC ,+40V；MGDG ,+
21 V；DGDG ,+24 V；Negative ion mode, PI, -58V；PG, LysoPG and PA, -57V；PS, -34V.
Preferably, filtered in S1 from the nylon membrane that bore is 0.22 micron.
Preferably, the extracting method of the crop sample of glycolipid containing crop and phosphatide is as follows in the S1：
S1：Soaked in isopropanol and the mixed solution of antioxidant that fresh crop sample is quickly adding at 73 ~ 77 DEG C；
S2：Extractant is added to extract to sample turned white the mixed solution in S1；Then extract, centrifuge to obtain organic phase；
S3：Organic phase produces the crop sample containing glycolipid and phosphatide in drying S2.
The higher glycolipid and phospholipid fraction that can extract polarity of isopropanol polarity, while the addition of antioxidant can prevent sugar
Oxidized and phospholipase D is activated in atmosphere for fat and phosphatide.Fresh crop sample is immersed into rapidly into 73 ~ 77 DEG C DEG C to contain
Among BHT isopropanol, isopropanol can extract the glycolipid and phospholipid fraction of polarity；Furthermore with the extractant that polarity is larger,
It can be very good to realize the extraction of glycolipid and phosphatide.
Preferably, the temperature of mixed solution is 75 DEG C in the S1.
Preferably, the oxidant is 2,6 one BHTs, butylated hydroxy anisole or the 2- tert-butyl groups to benzene
One kind in diphenol.
Preferably, the antioxidant in the S1 mixed solutions be that volume fraction is 0.01% 2,6 one di-t-butyls pair
Cresols.
Preferably, the fresh crop sample is one kind in rice leaf, cotton leaf or banana pulp.
Preferably, centrifugal rotational speed is 500rpm in the S4, and centrifugation time is 3 minutes.
Preferably, the temperature that nitrogen dries up in S6 is 35 ~ 40 DEG C.
Compared with prior art, the present invention has the advantages that：
The detection method of crop glycolipid and phosphatide provided by the invention, the high accuracy and Gao Ling of crop glycolipid and phosphatide can be achieved
The qualitative, quantitative of sensitivity, mass-to-charge ratio can be accurate to after decimal point the 3rd；The detection to crop content of phospholipid can be improved simultaneously
Limit is quantitative more accurate.
Brief description of the drawings
Fig. 1 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of glycolipid MGDG positive ion modes；
Fig. 2 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of glycolipid DGDG positive ion modes；
Fig. 3 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of phosphatide PC positive ion modes；
Fig. 4 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of phosphatide PE positive ion modes；
Fig. 5 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of phosphatide PI negative ion modes；
Fig. 6 is the mass spectrogram that the embodiment of the present invention 1 detects the detection of phosphatide PS negative ion modes；
Wherein, Prec precursor；NL is neutral loss；"+" and "-" represent positive ion mode and anion respectively
Pattern.
Embodiment
The present invention is expanded on further with reference to embodiment.These embodiments are merely to illustrate the present invention rather than limitation
The scope of the present invention.The experimental method of unreceipted actual conditions in lower example embodiment, generally according to this area normal condition or is pressed
The condition suggested according to manufacturer；Used raw material, reagent etc., unless otherwise specified, being can be from the business such as conventional market
The raw material and reagent that approach obtains.The change for any unsubstantiality that those skilled in the art is done on the basis of the present invention
And replace and belong to scope of the present invention.
The detection method of the crop glycolipid of embodiment 1 and phosphatide
The present embodiment is detected from following material and reagent：
One：Material and reagent
Material：Rice（Nipponbare）, cotton（Upland cotton YZ1）, banana（Brazilian any of several broadleaf plants）
Extract solution：Chloroform and methanol：Chloroform=2:1（v/v）
Phosphatide internal standard：6.6 nmol di14:0-PC, 6.6 nmol 13:0-lysoPC, 6.6 nmol 19:0-lysoPC,
3.6 nmol di14:0-PE, 3.6 nmol 14:0-lysoPE, 3.6 nmol 18:0-lysoPE, 3.6 nmol
di14:0-PG, 3.6 nmol 14:0-lysoPG, 3.6 nmol 18:0-lysoPG, 3.6 nmol di14:0-PA,
2.4 nmol di14:0-PS and 1.63 nmol di18:0-PI.
Glycolipid internal standard：44.55 nmol 16:0–18:0-MGDG, 35.45 nmol di18:0-MGDG, 8.65 nmol
16:0–18:0-DGDG, and 31.28 nmol di18:0-DGDG.
Mobile phase：A:Methanol：Acetonitrile：Water=42.5:42.5:15, add 0.1% formic acid（Positive ion mode）Or 3mM acetic acid
Ammonium（Negative ion mode）；B：The formic acid of isopropanol+0.1%（Positive ion mode）Or 3mM ammonium acetates（Negative ion mode）
Efficient liquid phase and mass spectrometry system：Shimadzu 20A UFLC efficient liquid phase instrument；AB SCIEX TripleTOF® 5600+
Mass spectrometer system；
Chromatographic column：PhenomenexKinetex C18 150 x 2.1 mm 2.6μ.
2nd, the extracting method of the crop sample containing glycolipid and phosphatide
The extracting method of crop sample containing glycolipid and phosphatide is as follows：
（1）Fresh plant sample is quickly adding into the isopropanol of 75 DEG C of preheatings of 3mL（Containing 0.01% BHT）Middle 15 points of immersion
Clock.
（2）1.5mL chloroforms and 0.6mL ultra-pure waters are added, is mixed.Then in being shaken on normal temperature shaking table 1 hour.
（3）Sample is transferred in a new vial, adds 4mL chloroform/methanol（2:1）Containing 0.01% BHT, shake
30 minutes, then sample solution is transferred to new vial.Repeat this step several times（About three times）All become to all samples
In vain.
（4）1mL 1M potassium chloride is added into the vial containing sample solution, rocks mixing, then 500rpm centrifugations 3
Minute, abandoning supernatant.2mL ultra-pure waters are added, are rocked, then 500rpm is centrifuged 3 minutes, abandoning supernatant.
（5）Plant sample after extraction is dried overnight at 105 DEG C, weighs dry weight, gained dry weight is 9 ~ 47mg.
（6）Solution is dried up with nitrogen（Temperature is 35-40 DEG C）.
3rd, detection method
The present embodiment detects crop glycolipid and phosphatide as follows：
1. adding the sample that 1mL chloroforms dry up to nitrogen, vibrate to sample and fully dissolve；
2. with 0.22 micron of nylon membrane filtered sample solution；
3. taking a part of sample, add 10 μ L internal standard mixed liquors so that finally the mixing liquid proportional containing sample is chloroform：Methanol：
（300mM）Ammonium acetate=300:665:35（v/v/v）, cumulative volume 1.8mL, being placed in brown, to enter sample to be detected；
4. use efficient liquid phase and mass spectrometric hyphenated technique（HPLC-MS/MS）Crop phosphatide is analyzed.
Chromatographic column：The μ liquid-phase conditions of 150 x of PhenomenexKinetex C18,2.1 mm 2.6：
Mobile phase：A:Methanol：Acetonitrile：Water=42.5:42.5:15, add 0.1% formic acid（Positive ion mode）Or 3mM ammonium acetates（It is negative
Ion mode）；
B：The formic acid of isopropanol+0.1%（Positive ion mode）Or 3mM ammonium acetates（Negative ion mode）Flow velocity：300 µL/min；Column temperature：
40 ℃；Sample size：8 µL.
Liquid phase gradient condition is as follows：
| Time（min） | Mobile phase A（%） | Mobile phase B（%） |
| 10 | 60 | 40 |
| 35 | 35 | 65 |
| 42 | Terminate |
Mass spectrographic parameter is arranged to：Atomization gas：55 psi；Aid in gas：55 psi；Gas curtain gas：35 psi；Ion source temperature：300
℃；Electron spray voltage：+ 5.5 kV or -4.5 kV；Collision voltage（CE）：Positive ion mode, PE and lysoPE ,+28V；PC and
LysoPC ,+40V；MGDG ,+21 V；DGDG ,+24 V；Negative ion mode, PI, -58V；PG, lysoPG and PA, -57V；
PS, -34V.
Empirical tests, using the detection method of the present invention, the most phosphatide of crop can be eluted during gradient elution
In the peak width of component, 15s or so, kind of phosphatide and more than 30 kinds of glycolipid fractions about more than 100 are can detect；And the present invention sensitivity and
Accuracy is more preferable, can more accurately observational measurement crop phosphatide（Mass-to-charge ratio can be accurate to after decimal point the 3rd）, together
When can provide more accurately quantify detection limit.Method on the present embodiment is in rice（Nipponbare）, cotton（Upland cotton
YZ1）, banana（Brazilian any of several broadleaf plants）The testing result of middle glycolipid and phosphatide is shown in Table 1.Fig. 1 ~ 6 are several conventional glycolipid such as MGDG（Such as figure
1）、DGDG（Such as Fig. 2）With phosphatide such as PC（Such as Fig. 3）、PE（Such as Fig. 4）、PI（Such as Fig. 5）、PS（Such as Fig. 6）Mass spectrogram.
Glycolipid and phosphatide basal level in the crop of table 1（Nmol/mg dry weights）
| Lipid class | Scan Mode | Rice（Nipponbare） | Cotton（Upland cotton YZ1） | Banana（Brazilian any of several broadleaf plants） |
| MGDG | +NL179 | 370.259±15.417 | 201.531±41.871 | 2.331±0.711 |
| DGDG | +NL341 | 127.068±14.765 | 55.938±7.829 | 0.741±0.371 |
| PA | -pre153 | 2.182±0.269 | 0.396±0.077 | 1.839±0.066 |
| PC | +pre184 | 20.740±2.814 | 9.440±1.748 | 7.350±0.117 |
| PE | +NL141 | 7.557±0.306 | 3.295±0.618 | 2.895±0.051 |
| PG | -pre153 | 20.583±0.806 | 4.076±1.113 | 2.118±0.025 |
| PI | -pre153 | 4.240±0.617 | 6.232±0.570 | 2.258±0.0265 |
| PS | -NL87 | 0.944±0.290 | 0.784±0.085 | 0.554±0.027 |
| LPC | +pre184 | 0.527±0.071 | 0.240±0.058 | 0.389±0.002 |
| LPE | +NL141 | 0.174±0.027 | 0.048±0.013 | 0.538±0.001 |
| LPG | -pre153 | 0.125±0.021 | 0.132±0.045 | 0.047±0.001 |
Annotation：Prec:Precursor, precursor ion-scan, NL:Neutral loss, neutral loss scan is positive and negative, represents
Negative ions pattern.
Claims (10)
1. the detection method of a kind of crop glycolipid and phosphatide, it is characterised in that the detection method comprises the following steps：
S1：Add after chloroform is vibrated to abundant dissolving and filter into the crop sample of glycolipid containing crop and phosphatide；Then in adding
Mark mixed liquor, methanol and ammonium acetate obtain sample solution；
S2：Sample solution in S1 is analyzed with mass spectrometric hyphenated technique using efficient liquid phase；
Wherein, positive ion detection pattern：Mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile acid, and the mixing is molten
The volume ratio of methanol, acetonitrile and water is 42.5 in liquid:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile acid；
Anionic textiles pattern：Mobile phase A is the mixed solution of methanol, acetonitrile, water and volatile base, first in the mixed solution
The volume ratio of alcohol, acetonitrile and water is 42.5:42.5:15；Mobile phase B is the mixed solution of isopropanol and volatile base.
2. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that chlorine in the sample solution
The volume ratio of imitative, methanol and ammonium acetate is 300:665:35.
3. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that in mobile phase A and Mobile phase B
Volatile acid is formic acid or acetic acid, and the volume fraction of the volatile acid is 0.1%.
4. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that in mobile phase A and Mobile phase B
Volatile base is ammonium formate or ammonium acetate, and the volume fraction of the volatile base is 0.1%.
5. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that liquid phase gradient elution bar in S2
Part is：0 ~ 10 minute, 40% Mobile phase B；10 ~ 35 minutes, 40% ~ 65% Mobile phase B；35 ~ 42 minutes, 0% Mobile phase B.
6. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that chromatographic column is in S2
PhenomenexKinetex C18。
7. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that flow rate of mobile phase is in S2
300 µL/min；Column temperature is 40 DEG C；Sample size is 8 μ L.
8. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that mass spectrometer system is AB in S2
SCIEX TripleTOF 5600+ mass spectrometer systems, the mass spectrographic parameter are arranged to：Atomization gas：55 psi；Aid in gas：55
psi；Gas curtain gas：35 psi；Ion source temperature：300℃；Voltage：-4.5KV/5.5KV；Collision voltage（CE）, cation mould
Formula, PE and LysoPE ,+28V；PC and LysoPC ,+40V；MGDG ,+21 V；DGDG ,+24 V；Negative ion mode, PI ,-
58V；PG, LysoPG and PA, -57V；PS, -34V.
9. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that glycolipid containing crop in the S1
It is as follows with the extracting method of the crop sample of phosphatide：
S1：Soaked in isopropanol and the mixed solution of antioxidant that fresh crop sample is quickly adding at 73 ~ 77 DEG C；
S2：Extractant is added to extract to sample turned white the mixed solution in S1；Then extract, centrifuge to obtain organic phase；
S3：Organic phase produces the crop sample containing glycolipid and phosphatide in drying S2.
10. the detection method of crop glycolipid and phosphatide according to claim 1, it is characterised in that antioxidant is 2 in S1,
One kind in 6 one BHTs, butylated hydroxy anisole or 2- TBHQs.
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