CN105372341A - Method for identifying Brassica napus L honey phenolic characteristic marker - Google Patents
Method for identifying Brassica napus L honey phenolic characteristic marker Download PDFInfo
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Abstract
The invention discloses a method for identifying a Brassica napus L honey phenolic characteristic marker. The method includes the steps of determining characteristic phenolic compounds in Brassica napus L honey by comparing phenolic compound characteristics of different varieties of honey, analyzing Brassica napus L honey samples from different provinces in China to confirm that the selected characteristic phenolic compounds are not influenced by producing areas, identifying the determined Brassica napus L honey characteristic phenolic compounds through a quadrupole time-of-flight mass spectrometer, obtaining spectrum and mass spectrum information of the compounds, and finally determining the compounds as the phenolic compounds with the maximum ultraviolet absorption wavelength of 276.2 nm, the molecular weight of 362 and the molecular formula of C16H26O9. The method is reasonable in design, a selected analysis instrument is high in sensitivity and high in feasibility, the Brassica napus L honey phenolic characteristic marker can be accurately identified, and meanwhile the reliable basis is provided for identifying the situation that Brassica napus L honey as low-price honey is mixed into high-price honey or directly sold as high-price honey.
Description
Technical field
The present invention relates to a kind of discrimination method of rape honey phenols signature identification thing, belong to field of food science.
Background technology
Honey (honey) is the crude sweet material that the nectar of honeybee collection nectariferous plant secretion is brewageed.There are some researches show, honey has antibacterial, anti-oxidant, anti-infective, antiatherosclerosis, the effect such as antitumor, and therefore honey is liked by consumers in general deeply.But because honey price is higher, on domestic market, honey quality is very different, some illegal businessmans, under economic interests are ordered about, carry out adulterated to honey, to reach the object of cutting down cost and reaping staggering profits.Honey adulteration comprises two kinds of modes: (1) directly adds syrup class material in natural honey product; (2) low price honey added to or directly pretend to be high price honey to sell, adulterated also referred to as kind.Honey component is complicated and the honey component of different plant source is close, and therefore honey types is adulterated is the one of the most difficult discriminating in honey adulteration form.Phenolic compound contamination in honey and the kind of nectariferous plant closely related, determine that the phenols marker of variety classes honey is significant for the adulterated discriminating of kind of honey.
Rape (
brassicacampestrisL.) strong adaptability, cold-resistant drought-enduring, the widest in China's cultivated area as nectariferous plant, output is maximum, and element is famous with " iron nectar source ".The rape florescence is 25-30 days, the flowering time southeast, 2 to March of southwest, 3 to April of In Middle And Lower Reaches of Changjiang River, 6 to July of northern area, the Yellow River.Rape honey is light amber, slightly muddy, has the fragrance of acid and rape flower, very easily crystallization, is creamy white after crystallization.Because output is high, relative to the honey of other kinds, rape honey is cheap, therefore is often used to adulterated in high price honey.
Summary of the invention
The object of the invention is to provide a kind of discrimination method of rape honey phenols signature identification thing, the method uses high performance liquid chromatography series diode array detector (HPLC DAD) to determine the phenols signature identification thing of rape honey, level Four bar time of-flight mass spectrometer is used to identify information such as this phenols signature identification thing molecular weight, thus determine rape honey phenols signature identification thing, provide reliable basis for differentiating that rape honey to mix as low price honey or directly pretends to be high price honey to sell.
The determination of rape honey phenols signature identification thing differentiates that rape honey mixes as sweet at a low price or directly pretend to be the sweet key of selling of high price, and for this reason, inventor has carried out following experiment:
(1) choose five kinds of common high price honey and comprise Mel Jujubae, honey of lungan flowers, honey of lychee flowers, Mel and sweet potato honey sample adding distil water fully dissolve, hydrochloric acid solution is used to regulate its pH value to be 2, obtain honey sample aqueous solution, honey sample aqueous solution is injected with in the chromatographic column of XAD 2 type resin, be aqueous hydrochloric acid solution and the distilled water flushing of 2 successively by pH value, remove carbohydrate isopolarity material, phenolic compound is retained on resin, wash-out is carried out with methyl alcohol, meoh eluate is removed by the mode of reduced pressure concentration, gained residue methyl alcohol dissolves, constant volume, be mixed with test sample solution, seal latter 4 DEG C to keep in Dark Place, rape honey sample does same treatment,
(2) use the test solution of HPLC-DAD to Mel Jujubae, honey of lungan flowers, honey of lychee flowers, Mel, sweet potato honey and rape honey sample to carry out determination and analysis, determine that rape honey sample retention time is the Characteristic chromatographic peak of 50.49min;
(3) gather the rape honey sample of Different sources, extract phenolic compound according to step (1) method;
(4) use the test solution of HPLC-DAD to the rape honey sample of Different sources to carry out determination and analysis, retention time is that the chromatographic peak intensity of 50.49min is maximum and appear at all in examination rape honey sample solution;
(5) use high-resolution mass spectrometer QTOF-MS to analyze the characteristic peak that in rape honey sample, retention time is 50.49min, the molecular weight obtaining this characteristic compound is 362;
Above-mentioned liquid phase chromatogram condition is: chromatographic column: ZorbaxSB-C18 (250mm × 4.6mm, 5 μm); Mobile phase: the formic acid solution of 0.15% and methyl alcohol; Flow rate of mobile phase: 1.0mL/min; Type of elution: gradient elution; Determined wavelength: 254nm, 280nm, 290nm, 320nm; Column temperature: 30 DEG C;
Above-mentioned Mass Spectrometry Conditions is: ion gun: electron spray ionisation source (ESI); Data acquisition scheme: negative ion mode; Data acquisition range: m/z100 ~ 1000; Source parameters: cracking voltage: 130V; Capillary voltage: 4kV; Nebulizer gas pressure: 45psig; Vaporizer temperature 350 DEG C; Dry gas (N
2) volumetric flow rate 10L/min.
By above-mentioned experiment, inventor obtains the discrimination method of rape honey phenols signature identification thing in a kind of honey, comprises the following steps:
(1) honey adding distil water is fully dissolved, hydrochloric acid solution is used to regulate its pH value to be 2, obtain honey sample aqueous solution, honey sample aqueous solution is injected with in the chromatographic column of XAD 2 type resin, be aqueous hydrochloric acid solution and the distilled water flushing of 2 successively by pH value, remove carbohydrate isopolarity material, phenolic compound is retained on resin, wash-out is carried out with methyl alcohol, meoh eluate is removed by the mode of reduced pressure concentration, gained residue methyl alcohol dissolves, constant volume, is mixed with test sample solution, seals latter 4 DEG C and keep in Dark Place;
(2) HPLC-DAD is used to carry out determination and analysis to the test solution of honey sample, if occur, retention time is the Characteristic chromatographic peak of 50.49min, further use high-resolution mass spectrometer QTOF-MS analyzes the characteristic peak that in honey sample, retention time is 50.49min, if there is molecular weight is 362, molecular formula is C
16h
26o
9characteristic compound, be namely mixed with rape honey in provable honey.
Above-mentioned liquid phase chromatogram condition is: chromatographic column: ZorbaxSB-C18 (250mm × 4.6mm, 5 μm); Mobile phase: the formic acid solution of 0.15% and methyl alcohol; Flow rate of mobile phase: 1.0mL/min; Type of elution: gradient elution; Determined wavelength: 254nm, 280nm, 290nm, 320nm; Column temperature: 30 DEG C;
Above-mentioned Mass Spectrometry Conditions is: ion gun: electron spray ionisation source (ESI); Data acquisition scheme: negative ion mode; Data acquisition range: m/z100 ~ 1000; Source parameters: cracking voltage: 130V; Capillary voltage: 4kV; Nebulizer gas pressure: 45psig; Vaporizer temperature 350 DEG C; Dry gas (N
2) volumetric flow rate 10L/min.
Level Four bar time of-flight mass spectrometer (QTOF-MS), as typical high resolution mass spectroscope, is one of powerful of identification.Relative to common liquid chromatograph, it can provide the relative molecular weight of analyte, the information such as chemical formula and structure.At present, by mass spectrum and chromatograph joint used method, be widely used in the fields such as clinical medicine, environmental protection, the evaluation of pesticides, national defense chemistry, Food Chemistry, organic chemistry, this shows that it has higher accuracy as qualitative, quantitative tool.
Advantage of the present invention and good effect: in (1) the present invention, determined rape honey feature phenols marker has extremely strong absorption at ultraviolet 280nm wavelength place do not detect or obvious characteristic compound that content is few in other high price honey.(2) carry out repeatedly extraction and analysis checking to the rape honey sample picking up from Chinese different province and area, prove that rape honey middle-molecular-weihydroxyethyl is 362, molecular formula is C
16h
26o
9feature phenols marker stable existence, do not affect by the place of production.(3) the present invention adopts level Four bar time of-flight mass spectrometer to analyze target compound, obtains this compound accurate molecular weight and molecular formula, provides reliable basis for differentiating that rape honey to mix as low price honey or directly pretends to be high price honey to sell.
Accompanying drawing explanation
Fig. 1 is Mel Jujubae, honey of lungan flowers, honey of lychee flowers, Mel, sweet potato honey and the HPLC-DAD chromatogram of rape honey sample at ultraviolet 280nm wavelength place;
Fig. 2 is the HPLC-DAD chromatogram of 17 batches of rape honey samples at ultraviolet 280nm wavelength place picking up from 7 different provinces, the whole nation;
Fig. 3 is that in rape honey sample, retention time is the uv absorption spectra of the characteristic compounds of 50.49min chromatographic peak;
Fig. 4 is that in rape honey sample, retention time is one-level (ms) mass spectrogram of the characteristic compounds of 50.49min chromatographic peak;
Fig. 5 is that in rape honey sample, retention time is secondary (ms/ms) mass spectrogram of the characteristic compounds of 50.49min chromatographic peak;
Fig. 6 is that in rape honey sample, retention time is the HPLC-DAD chromatogram of rape honey sample at ultraviolet 280nm wavelength place of 50.49min chromatographic peak.
Embodiment
Be further described below in conjunction with drawings and Examples.
Take five kinds of common high price honey respectively and comprise Mel Jujubae, honey of lungan flowers, honey of lychee flowers, Mel and each 20g of sweet potato honey sample, be placed in 200mL beaker, add 120mL distilled water and carry out dissolving and use hydrochloric acid solution adjust ph to 2; The sample solution of gained is injected the chromatographic column that AmberliteXAD-2 type resin has been housed, 300mLpH value is used to be the aqueous hydrochloric acid solution of 2 successively, 400mL distilled water wash-out, fully to remove carbohydrate isopolarity material, again with the aldehydes matter that 300mL methanol-eluted fractions is adsorbed on resin, collect meoh eluate, 40 DEG C of reduced pressure concentrations, residue be settled to 4mL and with after 0.45 ì m organic system filtering with microporous membrane as test solution, 4 DEG C of sealings are kept in Dark Place, analyze for HPLC-DAD, rape honey sample does same treatment.
During HPLC DAD analyzes, chromatographic column is ZorbaxSB-C18 chromatographic column (250mm × 4.6mm, 5 μm), and mobile phase A is methyl alcohol, and B is the aqueous formic acid of 0.15%; Flow rate of mobile phase is 1.0mL/min; Sample size is 5 ì L; Determined wavelength: 254nm, 280nm, 290nm, 320nm; Column oven temperature: 30 DEG C.Gradient elution program is as follows: 0min-10minB95%-85%; 10min-20minB85%; 20min-25minB85%-83%; 25min-30minB83%-70%; 30min-50minB70% 60%; 50min 60minB60% 45%; 60min 70minB45% 20%; 70min 75minB80%;
Analyzed by HPLC-DAD, Mel Jujubae, honey of lungan flowers, honey of lychee flowers, Mel, sweet potato honey and rape honey sample chromatogram figure are compared, obtains the characteristic peak (retention time is the chromatographic peak of 50.49min) of rape honey sample see Fig. 1.
Gather the rape honey sample in Sichuan, Hubei, Shaanxi, Qinghai, Jiangsu, Zhejiang, seven different provinces, Yunnan, extract phenolic compound.Carry out HPLC-DAD analysis, obtain the HPLC-DAD chromatogram of 17 batches of rape honey samples at ultraviolet 280nm wavelength place, 17 batches of rape honey samples all have Characteristic chromatographic peak to occur, see table 1 and Fig. 2 when 50.49min.
Use high-resolution mass spectrometer-level Four bar time of-flight mass spectrometer, analyzing retention time in rape honey sample is in the negative ion mode the characteristic peak of 50.49min, obtains the Information in Mass Spectra of this characteristic compound.First mass spectrometric shows its quasi-molecular ion peak: m/z:361.1504 [M-H]
-, obtain fragment ion molecular weight by second order ms and be respectively: 199.0971,155.1078,137.0974,101.0246.Molecule is lost and is met common phenolic compound feature (H
2o is 18, CO
2be 44), and its UV-absorbance maximum is 276.2nm, meets aldehydes matter spectral absorption characteristics, infers that this characteristic compounds belongs to phenolic compound, its molecular formula is C
16h
26o
9.See Fig. 3-6.
According to said method, determine the feature phenolic compound in rape honey, and obtain its molecular weight and molecular formula by mass spectrophotometry.Therefore, the present invention is applicable to differentiate rape honey phenols signature identification thing and provides reliable basis for differentiating that rape honey to mix as low price honey or directly pretends to be high price honey to sell.
Table 1 Different sources rape honey sample message
| Sample number into spectrum | Title | Hua Yuan | Geographical source | Acquisition time |
| YC1 | Rape honey | Brassica campestris L. | Sichuan | 2014.7 |
| YC2 | Rape honey | Brassica campestris L. | Zigong, Sichuan | 2014.7 |
| YC3 | Rape honey | Brassica campestris L. | Mianyang, Sichuan | 2014.7 |
| YC4 | Rape honey | Brassica campestris L. | Jianyang of Sichuan | 2014.7 |
| YC5 | Rape honey | Brassica campestris L. | Inland river, Sichuan | 2014.7 |
| YC6 | Rape honey | Brassica campestris L. | Sichuan Meishan | 2014.7 |
| YC7 | Rape honey | Brassica campestris L. | Jing Zhou, Hubei | 2014.4 |
| YC8 | Rape honey | Brassica campestris L. | Hubei is when sun | 2014.4 |
| YC9 | Rape honey | Brassica campestris L. | Hanzhong Bao He | 2013.4 |
| YC10 | Rape honey | Brassica campestris L. | Yang County, Hanzhong | 2013.4 |
| YC11 | Rape honey | Brassica campestris L. | Shuan Ru town, Ankang | 2013.4 |
| YC12 | Rape honey | Brassica campestris L. | Jian Min town, Ankang | 2013.4 |
| YC13 | Rape honey | Brassica campestris L. | Area just outside a city gate town, Ankang | 2014.7 |
| YC14 | Rape honey | Brassica campestris L. | Qinghai Men Yuan | 2014.12 |
| YC15 | Rape honey | Brassica campestris L. | Dongtai | 2013.4 |
| YC16 | Rape honey | Brassica campestris L. | Ningbo of Zhejiang | 2013.12 |
| YC17 | Rape honey | Brassica campestris L. | Luoping of Yunnan | 2013.12 |
Claims (3)
1. the discrimination method of rape honey phenols signature identification thing in honey, is characterized in that comprising the following steps:
(1) honey adding distil water is fully dissolved, hydrochloric acid solution is used to regulate its pH value to be 2, obtain honey sample aqueous solution, honey sample aqueous solution is injected with in the chromatographic column of XAD 2 type resin, be aqueous hydrochloric acid solution and the distilled water flushing of 2 successively by pH value, remove carbohydrate isopolarity material, phenolic compound is retained on resin, wash-out is carried out with methyl alcohol, meoh eluate is removed by the mode of reduced pressure concentration, gained residue methyl alcohol dissolves, constant volume, is mixed with test sample solution, seals latter 4 DEG C and keep in Dark Place;
(2) HPLC-DAD is used to carry out determination and analysis to the test solution of honey sample, if occur, retention time is the Characteristic chromatographic peak of 50.49min, further use high-resolution mass spectrometer QTOF-MS analyzes the characteristic peak that in honey sample, retention time is 50.49min, if there is molecular weight is 362, molecular formula is C
16h
26o
9characteristic compound, be namely mixed with rape honey in provable honey.
2. the discrimination method of rape honey phenols signature identification thing in honey according to claim 1, is characterized in that: described liquid phase chromatogram condition is: chromatographic column: ZorbaxSB-C18 (250mm × 4.6mm, 5 μm); Mobile phase: the formic acid solution of 0.15% and methyl alcohol; Flow rate of mobile phase: 1.0mL/min; Type of elution: gradient elution; Determined wavelength: 254nm, 280nm, 290nm, 320nm; Column temperature: 30 DEG C.
3. the discrimination method of rape honey phenols signature identification thing in honey according to claim 1, is characterized in that: described Mass Spectrometry Conditions is: ion gun: electron spray ionisation source ESI; Data acquisition scheme: negative ion mode; Data acquisition range: m/z100 ~ 1000; Source parameters: cracking voltage: 130V; Capillary voltage: 4kV; Nebulizer gas pressure: 45psig; Vaporizer temperature 350 DEG C; Dry gas N
2volumetric flow rate 10L/min.
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| CN108152389A (en) * | 2017-12-03 | 2018-06-12 | 西北大学 | A kind of method for differentiating honey of lychee flowers |
| CN110609108A (en) * | 2019-09-17 | 2019-12-24 | 西北大学 | Method for identifying amorpha fruticosa honey flower source marker |
| CN110749663A (en) * | 2018-07-24 | 2020-02-04 | 江苏出入境检验检疫局动植物与食品检测中心 | Method for identifying whether honey is doped with non-milk powder foreign protein |
| CN111426776A (en) * | 2020-06-12 | 2020-07-17 | 中国农业科学院蜜蜂研究所 | Application of HQR as characteristic marker of schefflera octophylla honey |
| CN111458422A (en) * | 2020-03-13 | 2020-07-28 | 中国农业科学院蜜蜂研究所 | Identification method of mature rape honey |
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| CN107529618A (en) * | 2016-11-09 | 2018-01-02 | 中国检验检疫科学研究院 | The quick determination method of phenolic compound in a kind of articles for washing |
| CN107024434A (en) * | 2017-03-28 | 2017-08-08 | 西北大学 | A kind of method for differentiating excessive hot-working Mel Jujubae |
| CN107024434B (en) * | 2017-03-28 | 2019-06-04 | 西北大学 | A method of identifying excessive hot-working Mel Jujubae |
| CN108152389A (en) * | 2017-12-03 | 2018-06-12 | 西北大学 | A kind of method for differentiating honey of lychee flowers |
| CN110749663A (en) * | 2018-07-24 | 2020-02-04 | 江苏出入境检验检疫局动植物与食品检测中心 | Method for identifying whether honey is doped with non-milk powder foreign protein |
| CN110609108A (en) * | 2019-09-17 | 2019-12-24 | 西北大学 | Method for identifying amorpha fruticosa honey flower source marker |
| CN111458422A (en) * | 2020-03-13 | 2020-07-28 | 中国农业科学院蜜蜂研究所 | Identification method of mature rape honey |
| CN111458421A (en) * | 2020-03-13 | 2020-07-28 | 中国农业科学院蜜蜂研究所 | Identification method of mature rape honey |
| CN111426776A (en) * | 2020-06-12 | 2020-07-17 | 中国农业科学院蜜蜂研究所 | Application of HQR as characteristic marker of schefflera octophylla honey |
| CN111426776B (en) * | 2020-06-12 | 2020-10-23 | 中国农业科学院蜜蜂研究所 | Application of HQR as characteristic marker of schefflera octophylla honey |
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Application publication date: 20160302 |