CN103163248B - Method for identifying blended soy sauce - Google Patents
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Abstract
The invention discloses a method for identifying blended soy sauce. The method adopts a manner of detecting whether characteristic components exist in a soy sauce sample to be detected, and if the characteristic components are detected in the soy sauce sample, the soy sauce is judged as the blended soy sauce, wherein the characteristic component can be one or more of isoleucyl-leucine, isoleucyl-leucine derivatives, isoleucyl-isoleucine, isoleucyl-isoleucine derivatives, leucyl-isoleucine, leucyl-isoleucine derivatives, leucyl-leucine and leucyl-leucine derivatives. The method has the advantages that the application range is wide, the identifying accuracy rate is high, and the operation is simple.
Description
Technical field
The present invention relates to the authentication method of soy sauce, relate in particular to a kind of authentication method of blended soy sauce.
Background technology
Soy sauce be China traditional brewage goods, the history of existing more than 2000 year, has become flavouring indispensable in common people's daily life so far.China's soy sauce annual production at present reaches 5,000,000 tons, accounts for 60% of world's annual production, and gross annual output value exceedes 16,000,000,000 yuan.By the difference of production technology, soy sauce is divided into and makes soy sauce and two kinds of blended soy sauces.Wherein, make soy sauce and refer to take soybean, wheat or wheat bran as raw material, through the microorganism liquid flavoring with special color of making that ferments; And blended soy sauce is that to make soy sauce be main body, forms with acid hydrolyzed vegetable protein matter liquid (AHVPS), food additives mixed preparing, production cost is lower.At present, owing to making soy sauce and the price difference of blended soy sauce, many retailers are in order to pursue high repayment, blended soy sauce is sold titled with the name making soy sauce, this serious infringement consumers in general's interests, therefore, differentiate and be of great practical significance with blended soy sauce making soy sauce.
Make soy sauce at present and have two classes with the discrimination method of blended soy sauce: a class is that the single characteristic chemical constituent detecting in blended soy sauce is differentiated, there is propylene chlorohydrin (3-Monochlo-Propane-1 for judging to make soy sauce with the non-index making soy sauce (being feature prompting thing) at present, 2-diol, 3-MCPD) and laevulic acid, but showing these two feature prompting things, research has its limitation: the raw material A HVPS of blended soy sauce in process of production, at hydrochloric acid catalysis, under hot conditions, about 10h just can thoroughly be hydrolyzed into free amino acid by phytoprotein, its subsidiary reaction generates 3-MCPD, this material can be carcinogenic and be caused sterility.And in making soy sauce, do not contain 3-MCPD, therefore can differentiate blended soy sauce by detecting 3-MCPD content.But in AHVPS production run, by the later stage adding the technique processing method such as hydrolytic accelerating agent, negative pressure steam distillation in hydrolysis, be less than 0.01mg/kg thereby make in AHVPS the content of 3-MCPD reduce to, to such an extent as to be difficult to detect.Laevulic acid (being called again levulinic acid) is distinctive a kind of composition in AHVPS.In AHVPS production run, in plant material, starch becomes glucose through acidolysis, and conversion of glucose becomes hydroxymethylfurfural, then resolves into laevulic acid, and traditional zymotic explained hereafter makes soy sauce and only contains extremely the laevulic acid of trace.In Japan and Taiwan, distinguish and make soy sauce and blended soy sauce by the make soy sauce content of middle laevulic acid of mensuration, if the content of laevulic acid exceedes 0.1% in soy sauce, just prove not make soy sauce.But the content of the laevulic acid to making soy sauce, in AHVPS, caramel colorant such as Li Guoji is measured, find that in soy sauce, levulinic acid content is lower, levulinic acid content more (high-load is 15.79%) in AHVPS, contain laevulic acid (high-load reaches 8.02%) and also measure in caramel colorant, because caramel colorant is the legal adjuvant that makes soy sauce, therefore, cannot differentiate and add making soy sauce and blended soy sauce of caramel colorant by mensuration laevulic acid, so the method still has larger application limitation.
Another kind of discrimination method is mainly to be made soy sauce and realized with the physicochemical property difference of blended soy sauce by searching.During adopting amino-acid nitrogen and the ratio of full nitrogen to judge to make soy sauce, the proposition such as Yan Yong whether adds AHVPS and adding proportion thereof, it thinks that the middle amino-acid nitrogen that normally makes soy sauce is 0.5 left and right with the ratio of full nitrogen, generally be not more than 0.57, and the amino-acid nitrogen of AHVPS is 0.79 with the ratio of full nitrogen, can judge in soy sample, whether to have added AHVPS by detecting in sample amino-acid nitrogen and the ratio of full nitrogen, but in reality detects, find, the method accuracy rate is lower.Wang Sheng etc. have reported and have adopted amounts of ammonium salt to distinguish the method making soy sauce with blended soy sauce, its principle is that the middle amounts of ammonium salt that normally makes soy sauce is little, and AHVPS uses hydrochloric acid in the time producing, in the time that being become to amino acid, proteolysis produces ammonia, ammonia and acid are combined into ammonium salt, and therefore its amounts of ammonium salt is relatively high.But the ammonium salt in caramel colorant can produce larger interference to this discrimination method.The utilizations such as State of Zhao China make soy sauce and the otherness of the infrared spectrogram of blended soy sauce, by Fourier transform middle infrared spectrum in conjunction with the inclined to one side square law of minimum, to making soy sauce, blended soy sauce, AHVPS can realize category analysis and discriminating, but because the method is to utilize the characteristic fingerprint peak making soy sauce in infrared spectrum to differentiate, and the infrared signature fingerprint peaks the incomplete similarity that make soy sauce of different brands, different brewage process, therefore the method applicable surface is narrower.
As can be seen here, how prior art is improved, the authentication method that a kind of simple to operate, blended soy sauce that accuracy rate is high, widely applicable is provided, can and make soy sauce blended soy sauce and effectively make a distinction, and this is the current technical issues that need to address in this area.
Summary of the invention
In view of this, the object of the present invention is to provide a kind of authentication method of blended soy sauce, simplify the operation course, improve the accuracy rate of identifying, the scope of application that expands evaluation.
For solving above technical matters, technical scheme of the present invention is:
An authentication method for blended soy sauce, detects in soy sample to be measured whether have property material, if detect property material in soy sample to be measured, judges that described soy sample is blended soy sauce; Wherein, described property material be in isoleucyl--leucine, isoleucyl--leucine derivant, isoleucyl--isoleucine, isoleucyl--isoleucine derivant, leucyl-isoleucine, leucyl-isoleucine derivant, LEU-LEU, LEU-LEU derivant any one or multiple.
Preferably, after being diluted, soy sample to be measured carries out again the detection of property material.
Preferably, soy sample to be measured is carried out carry out again after 20 times of dilutions more than volume the detection of property material.
Preferably, soy sample to be measured is first carried out to derivatization treatment, and then detect in the soy sample after derivatization treatment whether have property material.
Preferably, will after soy sample dilution to be measured, carry out derivatization treatment and then detect in the soy sample after derivatization treatment whether have property material.
Preferably, described derivatization treatment is: in soy sample to be measured, add borate buffer solution and o-phthalaldehyde(OPA) and beta-mercaptoethanol.
Preferably, adopt HPLC-MS to detect in soy sample to be measured, whether there is property material, under the negative ion detection mode of MS, the extraction ion flow graph that is 243.5 by scanning mass-to-charge ratio and the ion flow graph of property material standard items contrast, if there is the chromatographic peak that retention time is close in two figure, sample ions is extracted to the Information in Mass Spectra of this chromatographic peak in flow graph and the Information in Mass Spectra of property material standard items contrasts, if molecular weight, quasi-molecular ion peak is consistent with the Information in Mass Spectra of one or more property materials in standard items with ion fragment peak, show that described soy sample exists property material, judge that described soy sample is blended soy sauce.
Preferably, the chromatographic peak that described retention time is close refers to that retention time differs the chromatographic peak that is no more than 0.2min.
Preferably, adopt high HPLC-MS to detect and in the soy sample of derivatization treatment, whether have property material, under the negative ion detection mode of MS, the extraction ion flow graph that is 419.5 by scanning mass-to-charge ratio and the ion flow graph of property material standard items contrast, if there is the chromatographic peak that retention time is close in two figure, sample ions is extracted to the Information in Mass Spectra of this chromatographic peak in flow graph and the Information in Mass Spectra of property material standard items derivatization product contrasts, if molecular weight, quasi-molecular ion peak is consistent with the Information in Mass Spectra of one or more property materials in standard items with ion fragment peak, show that described soy sample exists property material, judge that described soy sample is blended soy sauce.
Preferably, the chromatographic peak that described retention time is close refers to that retention time differs the chromatographic peak that is no more than 0.2min.
Compared with prior art, the authentication method of blended soy sauce of the present invention, by detecting whether contain property material in soy sample to be measured, as contain property material, identify that it is blended soy sauce, due to described property material be not present in make soy sauce with the legal adjuvant of other soy sauce in, therefore the method can be suitable for the soy sauce goods that different brands and brewing method are produced, be not subject to the impact of other food additives, applied range.
Further, owing to adopting HPLC-MS to detect soy sauce to be measured, can accurately filter out property material, accuracy rate is high.
Further, the sample pre-treatments step of described method is divided into two kinds of modes, and a kind of mode is only to dilute, and another kind of mode is derivatization treatment again after dilution, and its process is all simple to operate, and can obtain qualification result in 60min, and detection efficiency is high.
Embodiment
In order to make those skilled in the art understand better technical scheme of the present invention, below by specific embodiment, the present invention is described in further detail.
The authentication method of blended soy sauce of the present invention is: detect in soy sample to be measured whether have property material, if detect property material in soy sample to be measured, judge that described soy sample is blended soy sauce; Wherein, described property material be in isoleucyl--leucine, isoleucyl--leucine derivant, isoleucyl--isoleucine, isoleucyl--isoleucine derivant, leucyl-isoleucine, leucyl-isoleucine derivant, LEU-LEU, LEU-LEU derivant any one or multiple.Isoleucyl--leucine, isoleucyl--isoleucine, leucyl-isoleucine, LEU-LEU are the distinctive 4 kinds of chemical compositions of blended soy sauce, make soy sauce and the legal adjuvant of other soy sauce in do not exist.
Detect in soy sample to be measured and whether have property material, can preferably adopt HPLC-MS(is high performance liquid chromatography and mass spectrographic coupling) detect, HPLC-MS detects as preferred version, but be not unique scheme, as long as detecting the method that whether has described property material in soy sample to be measured, can serve as embodiment of the present invention, the methods such as such as high performance liquid chromatography (HPLC), GC-MS(gas chromatography-mass spectrography), ion-exchange chromatography amino acid analysis method and Pulsed integrated amperometric electrochemical detection method.
By specific embodiment and application examples, the authentication method of blended soy sauce of the present invention is elaborated below.
Embodiment mono-
The authentication method of the blended soy sauce in the present embodiment is:
(1) get soy sample 1mL to be measured, be settled to 20mL with one-level water, as need testing solution.
(2) accurately take isoleucyl--leucine (Ile-Leu), isoleucyl--isoleucine (Ile-Ile), leucyl-isoleucine (Leu-Ile) and the each 20mg of LEU-LEU (Leu-Leu) standard reference material, with being settled to 10mL after the water-soluble solution of one-level, shake up, be formulated as mixed standard solution.
(3) adopt HPLC-MS to detect respectively above-mentioned need testing solution and mixed standard solution.
HPLC condition is made as: chromatographic column is C
18post, 250 × 4.6mm, column temperature: 40 ℃, flow velocity 1mL/min, it is 220nm that ultraviolet detects wavelength, and wash-out mobile phase ratio is water-acetonitrile (75:25, v/v), and sample size is 25 μ L.
MS condition is made as: ion gun is ESI, and sweep limit is: 150-500amu, and nitrogen flow rate is: 10.0L/min; Ion source temperature is 150 ℃, and Mass Spectrometer Method adopts negative ion mode, and the compound that is 244 to molecular weight carries out single ion detection scanning (SIM) scanning, and scanning mass-to-charge ratio (m/z) is set as 243.5.
(4) detect by above-mentioned condition, obtain the ion extraction flow graph of soy sample to be measured and mixed standard solution, if there is the chromatographic peak that retention time is close (retention time differs and is no more than 0.2min) in two figure, sample ions is extracted to the Information in Mass Spectra of this chromatographic peak in flow graph and the Information in Mass Spectra (in table 1) of Ile-Leu, Ile-Ile, Leu-Ile, Leu-Leu contrasts: if molecular weight, quasi-molecular ion peak and ion fragment peak are all consistent, show to exist in this soy sample to be measured this compound corresponding in table 1.In soy sample to be measured, detect a kind of compound or multiple compounds in table 1, all can judge that this soy sample to be measured is blended soy sauce.Otherwise if there is not the listed Information in Mass Spectra of table 1 in the ion extraction flow graph of sample, this soy sample to be measured does not exist any compound in table 1, judge that this soy sample to be measured is for making soy sauce.
The retention time of distinctive 4 kinds of chemical compositions and Information in Mass Spectra in table 1 blended soy sauce
Embodiment bis-
The authentication method of the blended soy sauce in the present embodiment is:
(1) get soy sample 1mL to be measured, add successively borate buffer solution (pH10.4) 1mL, the o-phthalaldehyde(OPA) 0.5mL of 10mg/mL and the beta-mercaptoethanol 0.5mL of 10mg/mL of 0.1mol/L, be settled to 20mL with one-level water, shake up, as need testing solution.
(2) accurately take Ile-Leu, Ile-Ile, Leu-Ile, the each 20mg of Leu-Leu standard reference material, with being settled to 10mL after the water-soluble solution of one-level, after shaking up, get this solution 1mL, add successively borate buffer solution (pH10.4) 1mL, the o-phthalaldehyde(OPA) 0.5mL of 10mg/mL and the beta-mercaptoethanol 0.5mL of 10mg/mL of 0.1mol/L, be settled to 10mL with one-level water, shake up, as mixed standard solution.
(3) adopt HPLC-MS to detect respectively above-mentioned need testing solution and mixed standard solution.
HPLC condition is made as: chromatographic column is C
18post, 150 × 4.6mm, column temperature: 35 ℃, flow velocity 1mL/min, it is 340nm that ultraviolet detects wavelength, adopts gradient elution, and elution program is in table 2, and sample size is 25 μ L.
Table 2 HPLC gradient elution mobile phase ratio
MS condition is made as: ion gun is ESI, and sweep limit is: 150-1000amu, and nitrogen flow rate is: 10.0L/min; Ion source temperature is 150 ℃, and Mass Spectrometer Method adopts negative ion mode, and the compound that is 420 to molecular weight carries out SIM scanning, and scanning m/z is set as 419.5.
(4) detect by above-mentioned condition, obtain the ion extraction flow graph of soy sample to be measured and mixed standard solution, if there is the chromatographic peak that retention time is close (retention time differs and is no more than 0.2min) in two figure, the Information in Mass Spectra that sample ions is extracted to this chromatographic peak in flow graph contrasts with the Information in Mass Spectra (in table 3) of Ile-Leu, Ile-Ile, Leu-Ile, Leu-Leu derivatization product: if molecular weight, quasi-molecular ion peak and ion fragment peak are all consistent, show that this soy sample to be measured exists this compound corresponding in table 3.In soy sample to be measured, detect a kind of compound or multiple compounds in table 3, all can judge that this soy sample to be measured is blended soy sauce.Otherwise if there is not the listed Information in Mass Spectra of table 3 in the ion extraction flow graph of sample, this soy sample to be measured does not exist any compound in table 3, judge that this soy sample to be measured is for making soy sauce.
Retention time and the Information in Mass Spectra of distinctive 4 kinds of chemical composition derivatization afterproducts in table 3 blended soy sauce
Wherein, in soy sample to be measured, add borate buffer solution and o-phthalaldehyde(OPA) and beta-mercaptoethanol to carry out derivatization treatment, this is a kind of preferred version to distinctive 4 kinds of chemical composition derivatization treatment in blended soy sauce, but be not unique scheme, embodiment of the present invention can be served as long as can react with distinctive 4 kinds of chemical compositions in blended soy sauce the derivatization method of generation stable product, for example, the method such as dansyl chloride derivatization method or chloro-carbonic acid fluorenes active carbon method can be adopted in other embodiments.
By application examples, the effect of authentication method of the present invention is verified below:
Application examples one
Get 4 kinds of commercially available blended soy sauces, 4 kinds of samples that make soy sauce, 5 kinds of AHVPS, above-mentioned sample carries out authentication process by embodiment mono-, within 60 minutes, has obtained qualification result, evaluation speed is fast, qualification result is in table 4, and from the data of table 4,4 kinds of blended soy sauces and 5 seed amino acid liquid all can detect one or more compositions that obtain in Ile-Leu, Ile-Ile, Leu-Ile, Leu-Leu, and 4 kinds make soy sauce and can't detect this 4 kinds of compounds, identify that accuracy rate is 100%.
Table 4 blended soy sauce is identified accuracy rate investigation
(O represents existence; X representative does not exist)
Application examples two
The raw material A HVPS of blended soy sauce is added to enter and make soy sauce, the mass percent that is mixed with AHVPS is respectively 10%, 30%, 50%, 70%, 90% mixed liquor, above-mentioned sample is processed by the authentication method of embodiment mono-, within 60 minutes, obtain qualification result, evaluation speed is fast, qualification result is in table 5, AHVPS addition is 10%, 30%, 50%, 70%, 90% sample all can detect and obtain Ile-Leu, Ile-Ile, Leu-Ile, one or more compositions in Leu-Leu, can't detect this 4 kinds of compounds and do not add in the making soy sauce of AHVPS, identify that accuracy rate is 100%.
Table 5 adds the sample identification that makes soy sauce of different proportion AHVPS
(O represents existence; X representative does not exist)
Below be only the preferred embodiment of the present invention, it should be pointed out that above-mentioned preferred implementation should not be considered as limitation of the present invention, protection scope of the present invention should be as the criterion with claim limited range.For those skilled in the art, without departing from the spirit and scope of the present invention, can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (10)
1. an authentication method for blended soy sauce, is characterized in that, adopts HPLC-MS to detect in soy sample to be measured whether have property material, if detect property material in soy sample to be measured, judges that described soy sample is blended soy sauce; Wherein, described property material be in isoleucyl--leucine, isoleucyl--isoleucine, leucyl-isoleucine, LEU-LEU any one or multiple;
Wherein, HPLC condition is made as: chromatographic column is C
18post, 250 × 4.6mm, column temperature: 40 ℃, flow velocity 1mL/min, it is 220nm that ultraviolet detects wavelength, wash-out mobile phase ratio is water-acetonitrile=75:25(v/v), sample size is 25 μ L;
MS condition is made as: ion gun is ESI, and sweep limit is: 150-500amu, and nitrogen flow rate is: 10.0L/min; Ion source temperature is 150 ℃, and Mass Spectrometer Method adopts negative ion mode, and the compound that is 244 to molecular weight carries out single ion detection scanning (SIM) scanning, and scanning mass-to-charge ratio (m/z) is set as 243.5.
2. the authentication method of blended soy sauce according to claim 1, is characterized in that, carries out the detection of property material after soy sample to be measured is diluted again.
3. the authentication method of blended soy sauce according to claim 2, is characterized in that, soy sample to be measured is carried out carrying out after 20 times of dilutions more than volume again to the detection of property material.
4. the authentication method of blended soy sauce according to claim 1, it is characterized in that, adopt HPLC-MS to detect in soy sample to be measured, whether there is property material, under the negative ion detection mode of MS, the extraction ion flow graph that is 243.5 by scanning mass-to-charge ratio and the ion flow graph of property material standard items contrast, if there is the chromatographic peak that retention time is close in two figure, sample ions is extracted to the Information in Mass Spectra of this chromatographic peak in flow graph and the Information in Mass Spectra of property material standard items contrasts, if molecular weight, quasi-molecular ion peak is consistent with the Information in Mass Spectra of one or more property materials in standard items with ion fragment peak, show that described soy sample exists property material, judge that described soy sample is blended soy sauce.
5. the authentication method of blended soy sauce according to claim 4, is characterized in that, the chromatographic peak that described retention time is close refers to that retention time differs the chromatographic peak that is no more than 0.2min.
6. the authentication method of a blended soy sauce, it is characterized in that, adopt HPLC-MS to detect whether there is property material in the soy sample to be measured of derivatization treatment, if detect property material in soy sample to be measured, judge that described soy sample is blended soy sauce; Wherein, described property material be in isoleucyl--leucine derivant, isoleucyl--isoleucine derivant, leucyl-isoleucine derivant, LEU-LEU derivant any one or multiple;
HPLC condition is made as: chromatographic column is C
18post, 150 × 4.6mm, column temperature: 35 ℃, flow velocity 1mL/min, it is 340nm that ultraviolet detects wavelength, adopts gradient elution, and HPLC gradient elution mobile phase ratio is in table 1, and sample size is 25 μ L; MS condition is made as: ion gun is ESI, and sweep limit is: 150-1000amu, and nitrogen flow rate is: 10.0L/min; Ion source temperature is 150 ℃, and Mass Spectrometer Method adopts negative ion mode, and the compound that is 420 to molecular weight carries out SIM scanning, and scanning m/z is set as 419.5;
Table 1HPLC gradient elution mobile phase ratio
7. the authentication method of blended soy sauce according to claim 6, is characterized in that, is after soy sample dilution to be measured, to carry out forming after derivatization treatment through the soy sample to be measured of derivatization treatment.
8. according to the authentication method of the blended soy sauce described in claim 6 or 7, it is characterized in that, described derivatization treatment is: in soy sample to be measured, add borate buffer solution and o-phthalaldehyde(OPA) and beta-mercaptoethanol.
9. according to the authentication method of the blended soy sauce described in claim 6 or 7, it is characterized in that, adopt HPLC-MS to detect and in the soy sample of derivatization treatment, whether have property material, under the negative ion detection mode of MS, the extraction ion flow graph that is 419.5 by scanning mass-to-charge ratio and the ion flow graph of property material standard items contrast, if there is the chromatographic peak that retention time is close in two figure, sample ions is extracted to the Information in Mass Spectra of this chromatographic peak in flow graph and the Information in Mass Spectra of property material standard items derivatization product contrasts, if molecular weight, quasi-molecular ion peak is consistent with the Information in Mass Spectra of one or more property materials in standard items with ion fragment peak, show that described soy sample exists property material, judge that described soy sample is blended soy sauce.
10. the authentication method of blended soy sauce according to claim 9, is characterized in that, the chromatographic peak that described retention time is close refers to that retention time differs the chromatographic peak that is no more than 0.2min.
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