CN107807184A - Application of the triptolide as the biomarker of toxic honey - Google Patents
Application of the triptolide as the biomarker of toxic honey Download PDFInfo
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- CN107807184A CN107807184A CN201710939867.7A CN201710939867A CN107807184A CN 107807184 A CN107807184 A CN 107807184A CN 201710939867 A CN201710939867 A CN 201710939867A CN 107807184 A CN107807184 A CN 107807184A
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Abstract
The present invention relates to field of food safety, specifically discloses triptolide and is applied as the biomarker of toxic honey and its in toxic honey is differentiated.The present invention has found by research, and triptolide is particularly suitable for use in the identification and identification of toxic honey, and the early diagnosis of honeybee poisoning crowd.On this basis, present invention further proposes a kind of UHPLC Q Exactive plus detection methods of triptolide, and the Pretreatment and detection parameters of honeybee sample are optimized.The biomarker and detection method of toxic honey provided by the present invention, to protecting the life and health of honey consumer and safeguarding that honeybee consumption industry healthy development has important practical significance.
Description
Technical field
The present invention relates to field of food safety, specifically, is related to biological marker of the triptolide as toxic honey
Thing and its applied in toxic honey is differentiated.
Background technology
Honey is that honeybee acquires the nectar of nectariferous plant or honeydew mixes with its secretion, through brewing it after a while
What is formed afterwards has confectionery.Honey belongs to traditional wholefood, has beauty, beauty treatment, a healthcare function such as calm the nerves, it is deep by
The common people like.Under normal circumstances, honey sweetness is tasty, nontoxic.Vast territory and abundant resources in China, and subregion, which is dispersed with, largely to be had
Malicious nectariferous plant, such as tripterygium wilfordii, tripterygium hypoglaucum hutcs, the rhizome of Chinese monkshood, Azalea pontica and elegant jessamine.Honeybee acquire these plants nectar it
Afterwards, toxic honey will be brewed into, these honey are typically smaller to honeybee toxicity, but larger to the toxicity of people, and people once eats by mistake
After these toxic honeies, honey poisoning, severe patient even causing death occurs.
According to incompletely statistics, 2014-2016, triennial China have broken out 9 honey poisoning events altogether, have been related to
Poisoning crowd is up to 99 people, and causing death's has 13 people.It can be seen that honey poisoning is endangered seriously China, it is related to as many as number, causes
The height of dead rate, already belongs to serious public health event, is paid close attention to by the whole society.Honey poisoning not newly shows in the recent period
As the Ming Dynasty《Compendium of Materia Medica》In detailed describe " July does not eat raw honey, makes us descending cholera cruelly ".Ancients in production and living just
Have appreciated that the honey that summer produced may be poisonous, particularly in the weather of arid, it is prone to poisoning;And suspect
Toxic honey may be related to poisonous nectariferous plant.In addition, the external report for also having " honey poisoning " event, especially adjoins
, there is the generation of honey poisoning event in the Turkey area of Black Sea and the Nepal area of Qinghai-Tibet Platean every year.By to honey
The investigation of poisoning Nectar Plants, it is determined that these toxic honeies are the flowers that poisonous kind azalea is acquired by honeybee
Honey.Scientific research personnel by toxic honey and poisoning personnel's blood analysis, find grayanotoxin (Grayanotoxin,
GTX) I and III is toxic honey major toxicity composition, and is marked G-III as the biology of azalea toxic honey
Will thing.At present, the reason for relevant China's honey poisoning event, it is to acquire tripterygium wilfordii and macleaya cordata by honeybee that scholars, which suspect,
Nectar and pollen, its foundation is that substantial amounts of macleaya cordata pollen and a small amount of tripterygium wilfordii are found that in the sample of toxic honey
Powder.Bee product supervision, inspection and testing analysis center of the Ministry of Agriculture (Beijing) always works on the investigation of poisonous nectariferous plant and had for many years
The research work of poisonous wasp honey, by the continuous observation in multiple honey poisoning incident regions, has primarily determined that toxic honey and honeybee
Acquire tripterygium wilfordii, the nectar height correlation of tripterygium hypoglaucum hutcs.Pass through lab analysis, it was found that the middle tripterygium wilfordii first of tripterygium wilfordii
Element moves to nectar, is transferred to after being gathered by honeybee in honey.But doubtful there is poisonous wasp in this seminar by more than 80 of collection
Sweet sample analysis is found that the average content of triptolide in toxic honey is only 500 μ g/kg.Based on triptolide small
Median lethal dose LD50 0.92mg/kg in mouse, contained triptolide is not enough to causing death in honey, therefore, single
The pure mark using triptolide as honey is not scientific and reasonable enough.Therefore, in toxic honey still containing it is unidentified go out
High toxic material.It is identified in tripterygium wilfordii plant at present and identify more than 300 and plant compound, can be substantially by it
Tripterygium wilfordii diterpenes diterpenoids, triterpenes and alkaloids are classified as, the toxicity of wherein diterpene-kind compound is most strong, and there is notable physiology to live
Property;Triterpene and alkaloids toxicity are relatively small, have been applied respectively in terms of medicine and insecticide.With thunder in diterpene product
The materials such as public rattan A prime, B prime, 15- hydroxyls triptolide and 16- hydroxyl triptolides are metabolism table, are that Thunder God Calamus is planted
Thing causes the most important composition of people's poisoning.Investigation finds that the toxic honey that people takes in 20-50g can cause people to be poisoned, and severe patient is very
To death.Therefore, substantial amounts of tripterygium wilfordii diterpenes diterpenoids material may be contained in toxic honey, except the triptolide reported it
Outside, its analog may also be contained.Based on this, the research of toxic honey biomarker is carried out in this research, it is intended to selects most
Good mark.
The material base of the intoxicating of toxic honey is illustrated, it is significant to identify and identify its biomarker.Have
Poisonous wasp honey once comes into the market, it will seriously endangers the life and health of honey consumer.Biomarker based on toxic honey
Its discrimination method can be quickly developed, so as to be the quick of the distribution of monitoring toxic honey, circulation and honey poisoning event
Diagnosis provides technical support.
The content of the invention
It is an object of the invention to the deficiency for the identification of existing toxic honey and authentication method, one kind is identified and identified
Brand-new toxic honey biomarker, and the detection method of toxic honey is established using the mark, for toxic honey
Identification and the diagnosis of honey poisoning crowd.
To achieve these goals, the present invention adopts the following technical scheme that.
One of technical scheme is:Triptolide as biomarker toxic honey identification and identification
The application of aspect.
The chemical structural formula of the triptolide is as shown in Figure 3.
The two of technical scheme are:Establish a kind of based on liquid phase series connection high resolution mass spectrum technology for detection honey sample
The method of triptolide in this.This method is using UHPLC-Q Exactive PuLs detection honey samples, by checking its figure
In spectrum whether the characteristic peak containing triptolide, judge honey whether be toxic honey, be based primarily upon triptolide in liquid
The accurate m/z values of retention time, accurate m/z values and its characteristic fragment ion in matter.
Specifically, described detected using UHPLC-Q Exactive PuLs in the collection of illustrative plates of honey sample should contain thunder
The accurate m/z values of public rattan B prime:377.16003([M+H]+;C20H25O7 +), its tolerance should be within 5ppm.
In addition, in order to improve the distinguishing ability of toxic honey, the retention time of the chromatographic peak of described triptolide should
This meets 4.5min (allowable error should be less than 0.5min).And Thunder God should be contained in its MS/MS collection of illustrative plates (daughter ion collection of illustrative plates)
(the C of fragments characteristic ion m/z 211.07590 of rattan B prime14H11O2 +), (C of m/z 155.0860812H11 +), m/z 167.08608
(C13H11 +)m/z 183.08099(C13H11O+), (C of m/z 195.0809914H11O+), and the error of its accurate mass number should
Less than 5ppm.Only meet tripterygium wilfordii second simultaneously in accurate m/z values, retention time and fragments characteristic ions in honey sample
The feature of element, can affirm that the honey sample contains triptolide, and will be to be classified as toxic honey sample.
Further, when honey sample is detected, preferred pair its use following pre-treating method:Take honey sample 2g
Add 4mL water dissolving, mix, be completely dissolved honey, then again plus 10mL ethyl acetate, after whirling motion 3min, 6000g from
Heart 5min, takes upper organic phase;Lower floor's liquid is extracted once with 10mL ethyl acetate again, and whirling motion centrifuges the same first step, is closed
And the organic phase extracted twice, under 40 DEG C of water-baths, nitrogen drying.Then dissolved with 1mL 20% methanol-water, cross 0.22 μm
Filter membrane, treat that machine is analyzed.
It should be appreciated that the technology after equal proportion expansion is carried out to the dosage of above-mentioned agents useful for same or raw material or is reduced
Scheme, it is substantially identical with the above.
Further, when being detected using UHPLC-Q Exactive plus to honey sample, described liquid-phase condition
It is as follows:
Chromatographic column:For C18 chromatographic columns, column temperature is room temperature:20℃.
Flow phase composition:Mobile phase A is 0.1% formic acid water, and Mobile phase B is 0.1% formic acid acetonitrile.
Condition of gradient elution is:0-1.0min, 5% B;1.0-2.0min, 5-20% B;2.0-6.5min, 20-
50% B;6.5-7.0min, 50-80% B;7.0-7.1min, 80-100% B;7.1-8.5min, 100%B;8.5-
8.6min, 100-5% B;8.6-10min 95% B.
Flow velocity:0.30mL/min;Sample size:3.0μL.
Described Mass Spectrometry Conditions are as follows:
Source parameters:
The flow velocity (sheath gas flow rate) 45 of sheath gas;Aid in the flow velocity (aux gas flow rate) 10 of gas;
The flow velocity (sweep gas flow rate) 0 of gear cone gas;Electron spray voltage (spray voltage) 3.5kV;Ion conduit
320 DEG C of temperature (capillary temperature);S-lens RF level are set to 60;Temperature (the Heater of ion gun
temperature)350℃
The pattern of collection is the F μ Ll MS-ddMS2 under positive ion mode:
Wherein F μ Ll MS design parameter sets as follows:Resolution ratio (Resolution):70000;AGC Target:
3e6;Maximum IT:100ms;Scan range:200-800Da;Spectrum data:Centroid.
Wherein dd-MS2 design parameter sets as follows:Resolution ratio (Resolution):15000;AGC Target:
1.6e5;Maximum IT:50ms;Loop count:1;Isolation window:2.0Da;NCE:42;Spectrum
data:Centroid.And in dd settings, Minimum AGC:8.0e3;Apex trigger:2-6s;Exclude
isotope:on;Dynamic exclus:8.0s.
The triptolide detected using UHPLC-Q Exactive plus instruments in honey of the announcement of the present invention, base
In the accurate mass number that high resolution mass spectrum provides, this method has higher specificity and sensitivity, and its detection limit can reach 2
μg/kg.The instrument used based on this method and the parameter announced, different assay laboratories and testing agency can be according to liquid phase strings
Join the relevant knowledge of high resolution mass spectrum technology, parameter therein is necessarily adjusted.Moreover, even lacking tripterygium wilfordii second
, still can be by checking the accurate mass of triptolide and its fragment ion of characteristic come really in the case of plain reference substance
Determine whether contain triptolide in honey sample.Triptolide is as tripterygium wilfordii and the characteristic chemical combination of tripterygium hypoglaucum hutcs
Thing, by detecting in honey whether contain triptolide to differentiate whether honey contains tripterygium wilfordii toxic honey.
The present invention relates to raw material or reagent be ordinary commercial products, the operation being related to is unless otherwise specified
This area routine operation.
On the basis of common sense in the field is met, above-mentioned each optimum condition, it can be mutually combined, obtain specific embodiment party
Formula.
Brief description of the drawings
Fig. 1 is the accurate extraction mass chromatogram (RT=5.37min) of triptolide:(a) tripterygium wilfordii nectar sample;
(b) toxic honey sample;(c) normal honey sample.
Fig. 2 is the mass spectrogram (A) and its daughter ion collection of illustrative plates (B) of the accurate mass number of triptolide.
Fig. 3 is the chemical structural formula of triptolide.
Fig. 4 is the accurate extraction particle flux of triptolide (RT=5.37min) and triptolide in tripterygium wilfordii fresh flower
Chromatogram (RT=6.72min).
Fig. 5 is the accurate extraction particle flux of tripterygium wilfordii fresh flower honey triptolide (RT=5.37min) and triptolide
Chromatogram (RT=6.72min).
The accurate extraction particle flux color of triptolide (RT=5.37min) and triptolide in Fig. 6 tripterygium wilfordii honey
Spectrogram (RT=6.72min):(a) the toxic honey sample of Huangshi tripterygium wilfordii planting base collection is come from;(b) come from
The tripterygium wilfordii honey sample of Chongqing WuLong;(c) the tripterygium wilfordii honey sample of Xiushan, Chongqing is come from.
Embodiment
The preferred embodiment of the present invention is described in detail below in conjunction with embodiment.It is it will be appreciated that following real
Providing merely to play the purpose of explanation for example is applied, is not used to limit the scope of the present invention.The skill of this area
Art personnel can carry out various modifications and replacement in the case of without departing substantially from spirit of the invention and spirit to the present invention.
Experimental method used in following embodiments is conventional method unless otherwise specified.
Material used, reagent etc., unless otherwise specified, are commercially obtained in following embodiments.
Embodiment 1
Test case:
1st, test material:Fresh flower, nectar and the toxic honey of tripterygium wilfordii;
Wherein, the nectar of tripterygium wilfordii and toxic honey are mainly in Huangshi China Resources, Hubei Wuhan three nine-day periods after the winter solstice medicine tripterygium wilfordii planting matrix
Ground obtains.
At the beginning of mid-June at florescence to August in tripterygium wilfordii, the fresh flower of tripterygium wilfordii is plucked, and thunder is drawn using capillary glass tube
The nectar of public rattan.In addition, in order to obtain the honey of tripterygium wilfordii, 4 casees are placed at the beginning of 5 months before the florescence of tripterygium wilfordii planting base
Honeybee, two casees Apis melliferas, honeybee in two casees, and before placement, honey and pollen in honeycomb are removed, after beehive is placed 2 weeks,
Allow honeybee to collect enough honey to be stored in honeycomb, then each beehive collection honey 100-500g, be more than in honeycomb
Honey is destroyed.
2nd, totally 80 parts of common honey sample where is bought from market or beekeeper, such as acacia honey, twigs of the chaste tree honey, rape
Honey, lichee honey, jujube flower honey, longan, honey, lime tree honey and all flower honey.
3rd, 2016 and in June, 2017-tripterygium wilfordii of August part and the florescence of tripterygium hypoglaucum hutcs, from it has been reported that crossing
Honey poisoning collection 83 parts of honey in region occurred frequently, such as Hefeng of Hubei, Lichuan, Chongqing, Sichuan, Fujian Taining, Dali, Yao
The provinces and cities such as peace, Nujiang, auspicious cloud.
The doubtful toxic honey sample of above-mentioned collection is handled using following pre-treating method, then using UHPLC-Q
Exative Plus instruments sample introduction is analyzed.
Pre-treating method is specially:Take honey sample 2g to add 4mL water dissolving, mix, be completely dissolved honey, then
Again plus 10mL ethyl acetate, after whirling motion 3min, 6000g centrifugation 5min, take upper organic phase;Lower floor's liquid is again with 10mL's
Ethyl acetate extracts once, and whirling motion centrifuges the same first step, merges the organic phase extracted twice, under 40 DEG C of water-baths, nitrogen drying.
Then dissolved with 1mL 20% methanol-water, cross 0.22 μm of filter membrane, treat that machine is analyzed.
As for collection tripterygium wilfordii fresh flower, through shredding, tissue is homogenized and then entered according to above-mentioned honey Sample pretreatment method
Row processing, is then analyzed using UHPLC-Q Exative Plus instruments sample introduction.
The collecting amount of tripterygium wilfordii nectar is less, does not carry out the measures such as extraction and cleaning, only by 100 μ L tripterygium wilfordii nectar
Diluted with 900 μ L 20% methanol-water, cross 0.22 μm of filter membrane, treat that machine is analyzed.
When being detected using UHPLC-Q Exactive plus, liquid-phase condition and Mass Spectrometry Conditions such as the foregoing skill of the present invention
Described in art scheme.
By contrasting retention time (RT=5.37min) of the triptolide in chromatogram, accurate mass number m/z:
Main fragment ion in 377.16003 (see Fig. 2A) and accurately MS/MS collection of illustrative plates (see Fig. 2 B), determine the nectar of tripterygium wilfordii and have
Contain substantial amounts of triptolide in poisonous wasp honey.Detailed the illustrating in tripterygium wilfordii nectar and honey of Fig. 1 contains triptolide,
And corresponding chromatographic peak is not contained then in normal honey sample.It could therefore be concluded that the toxicity in poisonous nectariferous plant tripterygium wilfordii
Material triptolide is enriched in honey by the gathering honey behavior of honeybee.
Except detecting triptolide in the fresh flower, nectar and the honey that are gathered in the tripterygium wilfordii planting base of Huangshi
Outside, also detect the triptolide reported before (see Fig. 4, Fig. 5 and Fig. 6 a).But the result of accurate quantitative analysis shows have
The content of triptolide is typically larger than triptolide in poisonous wasp honey sample, is approximately 3-10 times of triptolide.Early stage text
The acute toxicity test in mouse of report triptolide is offered, its LD50 is 0.80mg/kg b.w., than triptolide
0.93mg/kg b.w. are larger.But in view of triptolide whether exists compared with triptolide in toxic honey sample
Certain advantage is respectively provided with content and toxicity.Based on this, the biological marker using triptolide as tripterygium wilfordii toxic honey
Thing is more scientific and reasonable.
To verify the reliability of conclusion, the present invention gathers the honey sample conduct of more than 80 part different cultivars in China
Blank control, as a result triptolide it has been not detected by all honey samples of collection.Moreover, the present invention was in 2016
With the tripterygium wilfordii of 2017 and the florescence of tripterygium hypoglaucum hutcs, 83 parts of doubtful honey samples are acquired 6-8 months, pass through detection point
Analysis, wherein triptolide and triptolide are detected in 30 parts of samples, wherein the tripterygium wilfordii second in all positive samples
The content of element is above more than 3 times of triptolide, and its content is between 20-6300ug/kg.Honey has been illustrated in Fig. 6 b and 6c
The accurate extraction particle flux chromatogram of triptolide and A prime in sample, it is seen that triptolide contains in toxic honey sample
Amount is higher than triptolide.
Thereby determine that, triptolide is more scientific and reasonable as the biomarker of tripterygium wilfordii toxic honey.
It should be appreciated that after equal proportion expansion is carried out to the dosage of above-described embodiment agents useful for same or raw material or is reduced
Technical scheme, it is substantially identical with above-described embodiment.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (8)
1. triptolide as biomarker in differentiating honey whether containing tripterygium wilfordii toxic honey in terms of application.
2. it is a kind of detection honey in whether the method containing tripterygium wilfordii toxic honey, it is characterised in that detection honey sample in be
It is no to contain triptolide.
3. according to the method for claim 2, it is characterised in that honey sample is detected using UHPLC-Q Exactive PuLs
This, by check in its collection of illustrative plates whether the characteristic peak containing triptolide, judge whether honey is toxic honey.
4. according to the method for claim 3, it is characterised in that triptolide is UHPLC-Q Exactive plus'
Contain m/z 377.16003 ([M+H] in accurate extraction particle flux chromatogram+, C20H25O7 +) quasi-molecular ion peak, its accurate matter
The error of amount number should be less than 5ppm.
5. according to the method for claim 4, it is characterised in that should contain in the daughter ion collection of illustrative plates (MS/MS) of triptolide
There are (the C of fragment ion m/z 211.0759014H11O2 +), m/z155.08608 (C12H11 +), m/z167.08608 (C13H11 +)m/z
183.08099(C13H11O+), (C of m/z 195.0809914H11O+), and the error of its accurate mass number should be less than 5ppm.
6. according to the method described in any one of claim 2~5, it is characterised in that honey sample before detection, is located before carrying out
Reason:Honey sample is taken to be added to the water dissolving, mixing is completely dissolved honey, and organic phase is extracted using ethyl acetate.
7. according to the method for claim 6, it is characterised in that after extracting organic phase using ethyl acetate, nitrogen drying, so
Dissolved afterwards with 20% methanol-water, cross 0.22 μm of filter membrane.
8. according to the method described in any one of claim 2~5, it is characterised in that examined using UHPLC-Q Exactive PuLs
Liquid-phase condition during survey is as follows:
Mobile phase is:A:0.1% formic acid water, B:0.1% formic acid acetonitrile;
Flow velocity:0.30ml/min;Chromatogram column temperature is:30℃;
Sample size is:5μL;Chromatographic column type is C18;
Using gradient elution program;UHPLC-Q Exactive plus Mass Spectrometry Conditions are as follows:
Ionization mode:Positive ion mode;
Drainage pattern is F μ Ll Mass and ddMS2;Atomization gas temperature:320.
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CN111646898A (en) * | 2020-08-06 | 2020-09-11 | 中国农业科学院蜜蜂研究所 | Chenopodium quinotoxin III hapten, artificial antigen, preparation method and application thereof |
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CN111440185A (en) * | 2020-03-31 | 2020-07-24 | 中国农业科学院蜜蜂研究所 | Hapten and application thereof in detection of tripdiolide and triptolide |
CN111440185B (en) * | 2020-03-31 | 2021-05-14 | 中国农业科学院蜜蜂研究所 | Hapten and application thereof in detection of tripdiolide and triptolide |
CN111646898A (en) * | 2020-08-06 | 2020-09-11 | 中国农业科学院蜜蜂研究所 | Chenopodium quinotoxin III hapten, artificial antigen, preparation method and application thereof |
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