CN109917054A - A kind of method of gibberellin detection sensitivity in raising crop sample - Google Patents
A kind of method of gibberellin detection sensitivity in raising crop sample Download PDFInfo
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- CN109917054A CN109917054A CN201910133854.XA CN201910133854A CN109917054A CN 109917054 A CN109917054 A CN 109917054A CN 201910133854 A CN201910133854 A CN 201910133854A CN 109917054 A CN109917054 A CN 109917054A
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- 229930191978 Gibberellin Natural products 0.000 title claims abstract description 57
- 239000003448 gibberellin Substances 0.000 title claims abstract description 57
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 238000001514 detection method Methods 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000035945 sensitivity Effects 0.000 title claims abstract description 13
- 238000001212 derivatisation Methods 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims abstract description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 16
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 230000014759 maintenance of location Effects 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000007664 blowing Methods 0.000 claims abstract description 3
- 150000002500 ions Chemical class 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 239000012973 diazabicyclooctane Substances 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 239000003375 plant hormone Substances 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- -1 diterpenoids compound Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- YKYMGFHOJJOSEB-UHFFFAOYSA-N butan-1-ol;potassium Chemical compound [K].CCCCO YKYMGFHOJJOSEB-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Abstract
The invention belongs to the trace detection fields of plant hormone, and in particular to a method of improve gibberellin detection sensitivity in crop sample.Gibberellin sample extraction liquid is obtained first from crop sample；Excessive derivatization reagent solution is added into gibberellin sample extraction liquid, adds excessive base catalyst, isothermal vibration performs the derivatization reaction, then after blowing, redissolve through nitrogen, obtains the crop sample for the LC-MS product of derivatization containing gibberellin detected；Ion pair information and retention time information are inputted in instrument, while the MS detection parameters are set, by crop sample sample detection.Heretofore described derivatization reagent reaction condition is mild, reaction step is simple, reactivity is very high, there is preferable selectivity for the gibberellin of trace, and derivatization reagent itself is positively charged, conducive to the ionization of derivatization product, the Ionization Efficiency of gibberellin can be greatly improved, thus the extremely strong detection sensitivity for increasing gibberellin in crops.
Description
Technical field
The invention belongs to the trace detection fields of plant hormone, and in particular to gibberellin inspection in a kind of raising crop sample
The method for surveying sensitivity.
Background technique
Gibberellin (Gibberellins) is a kind of plant growth regulator for belonging to diterpenoids compound, is sprouted in seed
Hair, growth of seedling, yielding positive results etc. has different physiological roles, be widely used melon fruits and vegetables, cereal crops,
In the production processes such as gardening.Since content of the gibberellin in plant is lower, it is carried out the higher pre-treatment of quantitative requirement and
Enrichment method, wherein Mass Spectrometer Method sensitivity can effectively be improved using the method for derivatization, reduce amount of samples, reduced
Instrumental pollution.By introducing polysubstituted amino group on gibberellin, the substance is improved in mass spectrum under positive ion mode
Ionization Efficiency, to improve detection sensitivity.The derivatization reagent for the gibberellin reported at present mainly has bromo three-level
Amine and bromo quaternary ammonium salt both, although can to a certain extent enhance sensitivity, derivatization is complicated for operation, to preceding place
Reason requires height, and needs special global analysis column, and testing cost is excessively high.
Summary of the invention
The present invention is in view of the deficiencies of the prior art, and it is an object of the present invention to provide gibberellin detection spirit in a kind of raising crop sample
The method of sensitivity.
For achieving the above object, the technical solution adopted by the present invention are as follows:
The method of gibberellin detection sensitivity, includes the following steps: in a kind of raising crop sample
(1) gibberellin sample extraction liquid is obtained from crop sample；
(2) gibberellin derivative reaction: being dissolved in solvent for derivatization reagent first, then to gibberellin sample extraction liquid
It is middle that excessive derivatization reagent solution is added, excessive base catalyst is added, after being sufficiently mixed uniformly, isothermal vibration spreads out
Biochemical reaction obtains gibberellin derivatization product after reaction, then after blowing, redissolve through nitrogen, obtains containing for what LC-MS was detected
The crop sample of gibberellin derivatization product；
(3) LC-MS is detected: being carried out LC-MS mark product exploitation first with gibberellin derivatization product and is obtained corresponding retain
Time and ion pair information；Then ion pair information and retention time information are inputted in instrument, while Mass Spectrometer Method ginseng is set
The crop sample sample detection of the product of derivatization containing gibberellin obtained by step (2) is obtained gibberellin in crop sample by number
The testing result of content.
In above scheme, the molecular structural formula of derivatization reagent described in step (2) is as follows:
Wherein R1=OSO2R3 or I, wherein R3=CH3Or mono/di/tri-o/m/p-R4substituted
Phenyl, R4=Me, Et, Pr, i-Pr, OCH3、OCH2CH3、NO2、F、Cl、CN、HCO、CH3COI；R2=CH3Or CH2CH3, n=
0~4.
In above scheme, the base catalyst being added in step (2) is selected from following a kind of: TEA (triethanolamine),
Pyridine (pyridine), DMAP (4-dimethylaminopyridine), t-BuOK (butanol potassium), t-BuONa (sodium butoxide), EtONa (ethyl alcohol
Sodium), ethylenediamine, ammonium hydroxide, diethylamine, DIPEA (N, N- diisopropylethylamine), (1,4- diazabicylo [2.2.2] is pungent by DABCO
Alkane).
In above scheme, the temperature of gibberellin derivative reaction described in step (2) is 20~100 DEG C, derivative reaction
Time be 0.5~3h.
In above scheme, in step (2), the solvent are as follows: CH3CN:H2O=90:10~60:40.
In above scheme, step (3) the MS detection parameters setting are as follows: DP range is set as 10~70eV, EP range
It is set as 4500~5500eV, CE range is set as 10~70eV, and CEP range is set as 20~80eV.
Beneficial effects of the present invention are as follows: derivatization reagent reaction condition of the present invention is mild, and reaction step is simple, instead
It answers activity very high, has preferable selectivity for the gibberellin of trace, and derivatization reagent itself is positively charged, be conducive to derivatization and produce
The ionization of object can greatly improve the Ionization Efficiency of gibberellin, while the present invention is also optimized for gibberellin
The LC-MS testing conditions of derivatization product, thus the extremely strong detection sensitivity for increasing gibberellin in crops.In addition, of the invention
The detection method can greatly reduce sample usage amount for expensive industrial crops and rare sample, reduce testing cost.
Specific embodiment
For a better understanding of the present invention, below with reference to the embodiment content that the present invention is furture elucidated, but it is of the invention
Content is not limited solely to the following examples.
Embodiment 1
The method of gibberellin detection sensitivity, includes the following steps: in a kind of raising crop sample
(1) acquisition of gibberellin sample extraction liquid: weighing 100mg biological sample powder, is rapidly added 1ml 70%ACN and mentions
Solvent, ice bath are taken, ultrasonic 10min, 14000r/min are centrifuged 5min, pipette supernatant, be repeated once to get extracting solution；
(2) it gibberellin derivative reaction: is performed the derivatization after gibberellin sample extraction liquid and derivatization reagent are mixed anti-
It answers, reaction equation is as follows:
Derivative reaction condition: being dissolved in solvent for derivatization reagent, then after mixing with gibberellin sample extraction liquid, is added
Catalyst alkali, 85 DEG C of concussion 1h perform the derivatization reaction, after reaction, blow through nitrogen, 200ul water/acetonitrile/formic acid (950/49/
1, volume ratio) redissolve after, the sample of the gained product of derivatization containing gibberellin is for detecting；
The molecular formula of the derivatization reagent selected in the present embodiment are as follows: C4H11IN+, structural formula is
Average molecular weight 200.04, m/z:199.99 (100.0%), 201.00 (4.3%),
Elemental analysis result: C, 24.02；H,5.54；I,63.44；N,7.00.Derivatization reagent dosage is 20ul, 10umol/ml；It is molten
Agent are as follows: CH3CN/H2O=80:20；The catalyst alkali selected is 20ul TEA；
(3) LC-MS is detected: being carried out LC-MS mark product exploitation using gibberellin derivatization product and is obtained corresponding retention time
With ion pair information, it is arranged the MS detection parameters (as shown in table 1 below), the gibberellin in gained extracting solution is reacted to step (2)
Derivative compound carries out LC-MS detection.
1 retention time of table, ion pair and the MS detection parameters
LC-MS detection is carried out to not derivative gibberellin using the MS detection parameters in table 1 simultaneously, by gibberellin and is spread out
The LC-MS testing result of biochemical gibberellin is compared, and comparison result is as shown in table 2 below, and comparing result is shown, in rice sample
The detection signal strength of gibberellin significantly increases after derivative and type dramatically increases.
The LC-MS testing result of 2 gibberellin of table and derivatization gibberellin compares
Further, the present invention chooses crop sample rice, barley and wheat, is detected using the above method wherein red mould
The content of element examines the LC-MS of the derivative front and back of rice gibberellin, the derivative front and back of barley gibberellin, the derivative front and back of gibberella saubinetii element
It surveys result to be compared, for comparison result as shown in table 3, table 4,3 result of table illustrates the method for the invention in addition to there is rice
Effect is outer, also has effect to other species containing gibberellin such as barley and wheat.
LC-MS testing result before 3 crops gibberellin of table is derivative
LC-MS testing result after 4 crops gibberellin of table is derivative
Obviously, above-described embodiment is only intended to clearly illustrate made example, and is not the limitation to embodiment.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And the obvious variation or change therefore amplified
It moves within still in the protection scope of the invention.
Claims (6)
1. a kind of method for improving gibberellin detection sensitivity in crop sample, which comprises the steps of:
(1) gibberellin sample extraction liquid is obtained from crop sample；
(2) gibberellin derivative reaction: being dissolved in solvent for derivatization reagent first, then adds into gibberellin sample extraction liquid
Enter excessive derivatization reagent solution, add excessive base catalyst, after being sufficiently mixed uniformly, isothermal vibration is performed the derivatization
Reaction, obtains gibberellin derivatization product after reaction, then after blowing, redissolves through nitrogen, and containing for obtaining detecting for LC-MS is red mould
The crop sample of plain derivatization product；
(3) LC-MS is detected: being carried out LC-MS mark product exploitation first with gibberellin derivatization product and is obtained corresponding retention time
With ion pair information；Then ion pair information and retention time information are inputted in instrument, while the MS detection parameters are set, it will
The crop sample sample detection of the product of derivatization containing gibberellin obtained by step (2), obtains GA content in crop sample
Testing result.
2. the method according to claim 1, wherein the molecular structural formula of derivatization reagent described in step (2)
It is as follows:
Wherein R1=OSO2R3 or I, wherein R3=CH3Or mono/di/tri-o/m/p-R4substituted phenyl, R4=
Me、Et、Pr、i-Pr、OCH3、OCH2CH3、NO2、F、Cl、CN、HCO、CH3COI；R2=CH3Or CH2CH3, n=0~4.
3. the method according to claim 1, wherein the base catalyst being added in step (2) is selected from as next
Kind: TEA, Pyridine, DMAP, t-BuOK, t-BuONa, EtONa, ethylenediamine, ammonium hydroxide, diethylamine, DIPEA, DABCO.
4. the method according to claim 1, wherein the temperature of gibberellin derivative reaction described in step (2)
It is 20~100 DEG C, the time of derivative reaction is 0.5~3h.
5. the method according to claim 1, wherein in step (2), the solvent are as follows: CH3CN:H2O=90:10
~60:40.
6. the method according to claim 1, wherein step (3) the MS detection parameters setting are as follows: DP range
It is set as 10~70eV, EP range is set as 4500~5500eV, and CE range is set as 10~70eV, and CEP range is set as 20
~80eV.
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| CN201910133854.XA CN109917054B (en) | 2019-02-22 | 2019-02-22 | Method for improving detection sensitivity of gibberellin in crop sample |
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Cited By (1)
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