CN110018258A - The method for qualitative and quantitative detection of sulfur-containing compound in a kind of Yunnan truffle - Google Patents
The method for qualitative and quantitative detection of sulfur-containing compound in a kind of Yunnan truffle Download PDFInfo
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- CN110018258A CN110018258A CN201910349705.7A CN201910349705A CN110018258A CN 110018258 A CN110018258 A CN 110018258A CN 201910349705 A CN201910349705 A CN 201910349705A CN 110018258 A CN110018258 A CN 110018258A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/64—Electrical detectors
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
- G01N30/8624—Detection of slopes or peaks; baseline correction
- G01N30/8631—Peaks
- G01N30/8634—Peak quality criteria
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/045—Standards internal
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
- G01N2030/047—Standards external
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/062—Preparation extracting sample from raw material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/64—Electrical detectors
- G01N2030/685—Electrical detectors flame photometry
Abstract
The invention discloses a kind of method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle, which is characterized in that with the volatile component in the method extraction truffle sample of headspace solid-phase microextraction；By in the volatile component sample introduction of extraction to gas-chromatography-flame photometric detector combination equipment, quantitative detection is carried out to sulfur-containing compound by establishing calibration curve equation；Under the same conditions into n-alkane, the retention index RI of volatile materials is calculated by KOVATS retention index formula, and qualitative detection is carried out to sulfur-containing compound.The present invention carries out the analysis detection of qualitative, quantitative using headspace solid-phase microextraction combination gas-chromatography-flame photometric detector to the target sulfur-containing compound in truffle, and operating procedure is few, and qualitative, quantitative is accurate, is simple and efficient.
Description
Technical field
It is specific bright to be related to a kind of determining for sulfur-containing compound in Yunnan truffle the invention belongs to truffle composition detection technical field
Property quantitative detecting method.
Background technique
In recent years, the yield of Chinese truffle and export volume cumulative year after year, but it is domestic non-to the research of domestic truffle flavor
It is often few.In truffle, the content of C8 compound is in the majority, mainly provides mushroom, the characteristic perfume of soil, but it is found that really
Brought for truffle pungent, garlic is fragrant, and Moschus and peculiar fragrance are that concentration is lower, the lower sulfur-containing compound of threshold value.Sulfur-bearing chemical combination
Object play the role of to the contribution of the flavor of truffle it is conclusive, such as: dimethyl disulfide, NSC 97324,1,2,4- trithios
Heterocycle pentane, thiophene derivant etc. are considered as the character flavor compound of truffle.Dimethyl sulfide, dimethyl disulfide, three
Dimethyl sulfide and 3- (methyl mercapto) propionic aldehyde are the basis of Europe and Asia black pine fragrance.The perfume (or spice) of most critical in kahikatea dew
Gas ingredient is bis- (methyl mercapto) methane (BMTM).Manufacturer uses BMTM as the seasoning of truffle oil and various flavor truffle food
Agent, because it has apparent truffle odor characteristic.
Currently, common SPME combination GC-MS can simply and efficiently in extractive analysis truffle volatile flavor component, but
Be it is lower for concentration some in truffle, threshold value also extremely low crucial sulfur-containing compound can not detected.And flame luminosity
Detector (FPD) be it is a kind of have highly selective, highly sensitive detector to phosphorous, sulfur-containing compound, can be efficiently to pine
Sulfur-containing compound in dew carries out the analysis of qualitative, quantitative.
Summary of the invention
The technical problems to be solved by the present invention are: providing a kind of qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle
Method, this method can carry out detailed analysis detection to the sulfur-containing compound of truffle.
In order to solve the above-mentioned technical problems, the present invention provides a kind of qualitative, quantitative inspections of sulfur-containing compound in Yunnan truffle
Survey method, which comprises the steps of:
Step 1): with the volatile component in the method extraction truffle sample of headspace solid-phase microextraction；
Step 2): the volatile component sample introduction of step 1) extraction to gas-chromatography-flame photometric detector is combined equipment
In, quantitative detection is carried out to sulfur-containing compound by establishing calibration curve equation；
Step 3): under the same conditions into n-alkane, the guarantor of volatile materials is calculated by KOVATS retention index formula
Index RI is stayed, qualitative detection is carried out to sulfur-containing compound.
Preferably, in the step 1) truffle sample using the black pine, white from Yunnan Nanhua County autonomous region, the Yi nationality, distributed over Yunnan, Sichuan and Guizhou
At least one of truffle and false recessed truffle.
Preferably, the truffle sample in the step 1) are as follows: after cleaning the truffle of fresh picking, it is equal to select head size
Even, truffle similar in color is ground into truffle mud, is put into -8 DEG C of refrigerators and is sealed, for use.
Preferably, the step 2) specifically: truffle sample is put into headspace solid-phase microextraction bottle, internal standard compound is added,
30min is extracted at 44~46 DEG C using divinylbenzene/carbon molecular sieve/polydimethylsiloxane fiber head, then extraction equipment is inserted
Enter gas-chromatography-flame photometric detector sample injector, desorbs 5min under 250 DEG C not shunt mode.
It is highly preferred that the internal standard compound uses concentration for the 2- methyl -3- tetrahydrofuran mercaptan of 100mg/L.
Preferably, gas-chromatography-flame photometric detector parameter in the step 2) are as follows: use HP-INNOWAX (60m
× 0.25mm × 0.25 μm) chromatographic column, N2For carrier gas, flow is that 1.8mL/min. injector temperature is 250 DEG C, temperature program:
50 DEG C of reservation 3min, are warming up to 100 DEG C with the rate of 10 DEG C/min, retain 5min, are warming up to 140 DEG C with 3 DEG C/min, retain
10min rises to 200 DEG C with 2 DEG C/min, retains 5min；FPD temperature is set as 250 DEG C, and PMT voltage is set in 500V；Sample introduction side
Formula is not shunt, and keeps 5min.
Preferably, the method for quantitative detection is external standard method in the step 2), and standard substance used in quantitative detection is
Methyl mercaptan, dimethyl sulfide, dimethyl disulfide, double methyl mercapto methane, 3- methylthiopropionaldehyde, dimethyl sulfoxide, 2- acetyl group
At least one in thiazole, dipropyl trisulfide ether, three methyl mercapto propyl alcohol, dimethyl sulfone and bis- (2- methyl-3-furyl) disulfides
Kind.
Preferably, the step 3) specifically: under identical instrument condition, into n-alkane, by going out for n-alkane
Peak time calculates the retention index RI of volatile materials according to KOVATS retention index formula, carries out qualitative inspection to sulfur-containing compound
It surveys.
Preferably, the number of alkyl groups of n-alkane is C in the step 3)4-C30。
Qualitative calculation formula is as follows:
Wherein, RIxFor the retention index of determinand；txFor the retention time of volatile materials, min；tzFor with volatility object
Matter carbon atom belongs to the retention time of identical n-alkane, min；Z is the carbon atom number of volatile materials.
Quantitative detecting method uses external standard method, and calibration curve equation is as follows:
(Ax/Ai)=a (Cx/Ci)+b formula 2；
Wherein, AxFor the peak area of standard items, AiFor the peak area of internal standard compound, CxFor the concentration of sulfur-containing compound, CiIt is interior
The concentration of object is marked, a is slope, and b is intercept.
The present invention is using headspace solid-phase microextraction combination gas-chromatography-flame photometric detector to the target sulfur-bearing in truffle
Compound carries out the analysis detection of qualitative, quantitative, and operating procedure is few, and qualitative, quantitative is accurate, is simple and efficient.
Detailed description of the invention
Fig. 1 is the GC-FPD chromatogram of fresh black pine；
Fig. 2 is the GC-FPD chromatogram of fresh white truffle；
Fig. 3 is the GC-FPD chromatogram of the fresh recessed truffle of vacation.
Specific embodiment
In order to make the present invention more obvious and understandable, hereby with preferred embodiment, and attached drawing is cooperated to be described in detail below.
Embodiment 1
The method for qualitative and quantitative detection of sulfur-containing compound in a kind of Yunnan truffle, comprising the following steps:
1, material and instrument and equipment
1.1 material
The black pine (T1) for originating from Yunnan Nanhua County autonomous region, the Yi nationality, distributed over Yunnan, Sichuan and Guizhou is selected, Yunnan kahikatea reveals (T2), the false recessed truffle in Yunnan
(T3) truffle of three different cultivars is tested.
1.2 instrument and equipment
7890A-5973C type GC-MS combined instrument, Agilent Technologies (China) Co., Ltd, water-bath, blender, low temperature
Refrigerator
2, experimental method and content
The pre-treatment of 2.1 truffles
It goes after cleaning the truffle of fresh picking, selects that head is uniform in size, and truffle similar in color is put into JYL-C051
In type blender, it is ground into truffle mud, -8 DEG C of refrigerators is put into and is sealed, for use.
2.2 GC-FPD detection
2.2.1 headspace solid-phase microextraction: the fresh truffle sample of 2.0g is accurately weighed, 20mL headspace solid-phase microextraction bottle is put into
In, it is added 5 μ L internal standard compounds (100mg/L 2- methyl -3- tetrahydrofuran mercaptan), using 50/30 μm of DVB/CAR/PDMS (diethyl
Alkene benzene/carbon molecular sieve/polydimethylsiloxane) fiber head extracts 30min at (45 ± 1) DEG C, then by extraction equipment be inserted into GC into
Sample device desorbs 5min under 250 DEG C not shunt mode；
2.2.2 HP-INNOWAX (60m × 0.25mm × 0.25 μm) chromatographic column, N GC condition: are used2For carrier gas, flow
It is 250 DEG C for 1.8mL/min. injector temperature, temperature program: 50 DEG C of reservation 3min are warming up to 100 with the rate of 10 DEG C/min
DEG C, retain 5min, be warming up to 140 DEG C with 3 DEG C/min, retain 10min, rises to 200 DEG C with 2 DEG C/min, retain 5min.FPD temperature
Degree is set as 250 DEG C, and PMT voltage is set in 500V.Input mode is not shunt, and keeps 5min；
Into n-alkane (C4-C30), the appearance time of n-alkane is calculated according to KOVATS retention index formula and is volatilized
Property substance retention index (RI), to sulfur-containing compound carry out qualitative detection.
Qualitative calculation formula is as follows:Wherein RIxRefer to for the reservation of determinand
Number；txFor the retention time of volatile materials, min；tzWhen reservation to belong to identical n-alkane with volatile materials carbon atom
Between, min；Z is the carbon atom number of volatile materials.
The quantitative detecting method is external standard method, standard substance used in quantitative detection be methyl mercaptan, dimethyl sulfide,
Dimethyl disulfide, double methyl mercapto methane, 3- methylthiopropionaldehyde, dimethyl sulfoxide, 2- acetylthiazole, dipropyl trisulfide ether,
Three methyl mercapto propyl alcohol, dimethyl sulfone, bis- (2- methyl-3-furyl) disulfides.Mark product are dissolved in the truffle matrix of simulation, are matched
It is set to the mother liquor of 1000ppm.
11 sulfide standard items mother liquors are respectively diluted to 1:5,1:10,1:20,1:50,1 in proportion:
100,1:200 times.
Calibration curve equation is as follows: AxFor the peak area of standard items, AiFor the peak area of internal standard compound, CxFor sulfur-containing compound
Concentration, CiFor the concentration of internal standard compound, a is slope, and b is intercept.
3, results and discussion
The GC-FPD chromatogram of three kinds of truffles is as shown in Figs. 1-3.Table 1-3 is qualitative sulfur-containing compound in three kinds of truffles.
Qualitative sulfur-containing compound in the fresh black pine of table 1
Qualitative sulfur-containing compound in 2 fresh white truffle of table
| Serial number | Sulfur-containing compound | Qualitative fashion | HP-INNOWAX |
| 1 | Methyl mercaptan | FPD, RI | 696 |
| 2 | Dimethyl sulfide | FPD, RI | 721 |
| 3 | Dimethyl disulfide | FPD, RI | 1086 |
| 4 | Double methyl mercapto methane | FPD, RI | 1268 |
| 5 | 3- methylthiopropionaldehyde | FPD, RI | 1476 |
| 6 | 2- acetylthiazole | FPD, RI | 1652 |
| 7 | Dipropyl trisulfide ether | FPD, RI | 1659 |
| 8 | Three methyl mercapto propyl alcohol | FPD, RI | 1706 |
| 9 | Dimethyl sulfone | FPD, RI | 1929 |
Qualitative sulfur-containing compound in the fresh recessed truffle of vacation of table 3
| Serial number | Sulfur-containing compound | Qualitative fashion | HP-INNOWAX |
| 1 | Dimethyl sulfide | FPD, RI | 721 |
| 2 | Dimethyl disulfide | FPD, RI | 1086 |
| 3 | Double methyl mercapto methane | FPD, RI | 1268 |
| 4 | 3- methylthiopropionaldehyde | FPD, RI | 1476 |
| 5 | 2- acetylthiazole | FPD, RI | 1652 |
| 6 | Dipropyl trisulfide ether | FPD, RI | 1659 |
| 7 | Three methyl mercapto propyl alcohol | FPD, RI | 1706 |
| 8 | Bis- (2- methyl-3-furyl) disulfides | FPD, RI | 2156 |
Table 1-3 can be seen that the sulfur-containing compound that three different cultivars truffles detected from GC-FPD, pass through N-alkanes
It is qualitative to sulfur-containing compound progress that hydrocarbon calculates RI value.
11 standard items are made into the standard solution of 6 various concentration gradients by table 4, are detected by GC-FPD, are drawn respectively
Calibration curve equation out.
Table 4
Normal equation equation is established, outer marking quantitative is carried out to 11 kinds of sulfur-containing compounds, as shown in table 5.
Table 5
Conclusion: sulfur-bearing is carried out by truffle of the headspace solid-phase microextraction combination GC-FPD to three, same place of production different cultivars
The qualitative and quantitative analysis of compound identifies 9 kinds, 8 kinds and 9 kinds sulfide in kahikatea dew and false recessed truffle from black pine respectively,
By the way that RI value is qualitative and quantified by external standard method, calibration curve equation is established, it is precisely quantitative to key sulfur-containing compound.Three differences
There are many differences on content for the truffle of kind, and it is dimethyl sulfide that wherein content is highest, in the truffle of three kinds
Both provide the breath of rotten Chinese cabbage and corn.The sulfur-containing compound that the method produces truffle to Yunnan, which has, deeper more fully to be examined
Analysis is surveyed, is provided fundamental basis for the critical sulfide fragrance research of domestic truffle.The invention method can also be applied to other
In the more food inspection of sulfur content.
Claims (9)
1. the method for qualitative and quantitative detection of sulfur-containing compound in a kind of Yunnan truffle, which comprises the steps of:
Step 1): with the volatile component in the method extraction truffle sample of headspace solid-phase microextraction；
Step 2): by the volatile component sample introduction of step 1) extraction to gas-chromatography-flame photometric detector combination equipment, lead to
It crosses and establishes calibration curve equation to sulfur-containing compound progress quantitative detection；
Step 3): under the same conditions into n-alkane, refer to by the reservation that KOVATS retention index formula calculates volatile materials
Number RI carries out qualitative detection to sulfur-containing compound.
2. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1, which is characterized in that described
Step 1) in truffle sample using in black pine, kahikatea dew and false recessed truffle from Yunnan Nanhua County autonomous region, the Yi nationality, distributed over Yunnan, Sichuan and Guizhou extremely
Few one kind.
3. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1, which is characterized in that described
Truffle sample in step 1) are as follows: after cleaning the truffle of fresh picking, it is uniform in size to select head, truffle similar in color,
It is ground into truffle mud, -8 DEG C of refrigerators is put into and is sealed, for use.
4. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1, which is characterized in that described
Step 2) specifically: truffle sample is put into headspace solid-phase microextraction bottle, internal standard compound is added, using divinylbenzene/carbon molecules
Sieve/polydimethylsiloxane fiber head extracts 30min at 44~46 DEG C, then extraction equipment is inserted into gas-chromatography-flame luminosity
The sample injector of detector desorbs 5min under 250 DEG C not shunt mode.
5. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as claimed in claim 4, which is characterized in that described
Internal standard compound uses concentration for the 2- methyl -3- tetrahydrofuran mercaptan of 100mg/L.
6. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1 or 4, which is characterized in that
Gas-chromatography-flame photometric detector parameter in the step 2) are as follows: use HP-INNOWAX chromatographic column, N2For carrier gas, stream
It is 250 DEG C that amount, which is 1.8mL/min. injector temperature, and temperature program: 50 DEG C of reservation 3min are warming up to the rate of 10 DEG C/min
100 DEG C, retain 5min, be warming up to 140 DEG C with 3 DEG C/min, retain 10min, rises to 200 DEG C with 2 DEG C/min, retain 5min；FPD
Temperature is set as 250 DEG C, and PMT voltage is set in 500V；Input mode is not shunt, and keeps 5min.
7. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1, which is characterized in that described
The method of quantitative detection is external standard method in step 2), and standard substance used in quantitative detection is methyl mercaptan, dimethyl sulfide, two
Methyl disulfide, double methyl mercapto methane, 3- methylthiopropionaldehyde, dimethyl sulfoxide, 2- acetylthiazole, dipropyl trisulfide ether, three
At least one of methyl mercapto propyl alcohol, dimethyl sulfone and bis- (2- methyl-3-furyl) disulfides.
8. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as described in claim 1, which is characterized in that described
Step 3) specifically: under identical instrument condition, into n-alkane, the appearance time of n-alkane is retained according to KOVATS
Exponential formula calculates the retention index RI of volatile materials, carries out qualitative detection to sulfur-containing compound.
9. the method for qualitative and quantitative detection of sulfur-containing compound in Yunnan truffle as claimed in claim 1 or 8, which is characterized in that
The number of alkyl groups of n-alkane is C in the step 3)4-C30。
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Cited By (1)
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| US20120100255A1 (en) * | 2009-07-03 | 2012-04-26 | Richard Splivallo | Production of natural truffle flavours from truffle mycelium |
| CN108181390A (en) * | 2017-12-21 | 2018-06-19 | 北京工商大学 | The quantitative detecting method of sulfur-containing compound in a kind of white wine |
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| CN111323505A (en) * | 2020-03-18 | 2020-06-23 | 中国农业科学院兰州畜牧与兽药研究所 | Method for detecting sulfur-containing compounds in volatile flavor substances of fermented meat products |
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Application publication date: 20190716 |