WO2011023230A1 - Method of extracting mycotoxins from cereal grains - Google Patents
Method of extracting mycotoxins from cereal grains Download PDFInfo
- Publication number
- WO2011023230A1 WO2011023230A1 PCT/EP2009/061051 EP2009061051W WO2011023230A1 WO 2011023230 A1 WO2011023230 A1 WO 2011023230A1 EP 2009061051 W EP2009061051 W EP 2009061051W WO 2011023230 A1 WO2011023230 A1 WO 2011023230A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mycotoxins
- extraction
- solvent
- weight
- ethanol
- Prior art date
Links
- 231100000678 Mycotoxin Toxicity 0.000 title claims abstract description 32
- 239000002636 mycotoxin Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000004464 cereal grain Substances 0.000 title claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims description 20
- LINOMUASTDIRTM-QGRHZQQGSA-N deoxynivalenol Chemical compound C([C@@]12[C@@]3(C[C@@H](O)[C@H]1O[C@@H]1C=C(C([C@@H](O)[C@@]13CO)=O)C)C)O2 LINOMUASTDIRTM-QGRHZQQGSA-N 0.000 claims description 8
- 229930002954 deoxynivalenol Natural products 0.000 claims description 8
- LINOMUASTDIRTM-UHFFFAOYSA-N vomitoxin hydrate Natural products OCC12C(O)C(=O)C(C)=CC1OC1C(O)CC2(C)C11CO1 LINOMUASTDIRTM-UHFFFAOYSA-N 0.000 claims description 8
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 claims description 8
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 claims description 7
- RWQKHEORZBHNRI-BMIGLBTASA-N ochratoxin A Chemical compound C([C@H](NC(=O)C1=CC(Cl)=C2C[C@H](OC(=O)C2=C1O)C)C(O)=O)C1=CC=CC=C1 RWQKHEORZBHNRI-BMIGLBTASA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims 2
- 238000000605 extraction Methods 0.000 abstract description 19
- 239000011877 solvent mixture Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 6
- 230000033228 biological regulation Effects 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- VYLQGYLYRQKMFU-UHFFFAOYSA-N Ochratoxin A Natural products CC1Cc2c(Cl)cc(CNC(Cc3ccccc3)C(=O)O)cc2C(=O)O1 VYLQGYLYRQKMFU-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- DAEYIVCTQUFNTM-UHFFFAOYSA-N ochratoxin B Natural products OC1=C2C(=O)OC(C)CC2=CC=C1C(=O)NC(C(O)=O)CC1=CC=CC=C1 DAEYIVCTQUFNTM-UHFFFAOYSA-N 0.000 description 4
- 238000012421 spiking Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930195730 Aflatoxin Natural products 0.000 description 3
- 239000005409 aflatoxin Substances 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- XWIYFDMXXLINPU-UHFFFAOYSA-N Aflatoxin G Chemical compound O=C1OCCC2=C1C(=O)OC1=C2C(OC)=CC2=C1C1C=COC1O2 XWIYFDMXXLINPU-UHFFFAOYSA-N 0.000 description 1
- BXFOFFBJRFZBQZ-QYWOHJEZSA-N T-2 toxin Chemical compound C([C@@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 BXFOFFBJRFZBQZ-QYWOHJEZSA-N 0.000 description 1
- BXFOFFBJRFZBQZ-UHFFFAOYSA-N T2 Toxin Natural products C1=C(C)C(OC(=O)CC(C)C)CC2(COC(C)=O)C1OC1C(O)C(OC(C)=O)C2(C)C11CO1 BXFOFFBJRFZBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B9/00—Preservation of edible seeds, e.g. cereals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/23—Removal of unwanted matter, e.g. deodorisation or detoxification by extraction with solvents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
- G01N33/10—Starch-containing substances, e.g. dough
Definitions
- the present invention relates to a method of extracting mycotoxins from cereal grains and in particular to a method of solvent extraction employing an alcohokwater based extraction solvent.
- Mycotoxins tend to be very stable and may produce severe illness when ingested, inhaled, or introduced into the body by any other means.
- mycotoxins are known to be poisonous or carcinogenic when consumed by humans or animals.
- Mycotoxins are produced by molds and fungi during their growth on food and feed and may remain in food and feed long after the mold or fungus that produced them has died. Therefore products that are not visibly moldy or do not test positive for mold count can still contain potentially dangerous levels of mycotoxins.
- the method employed is disclosed as requiring the extraction of the mycotoxin from the cereal grain sample using known solvent extraction methods involving an alcohol/water solvent comprised in a known manner.
- mycotoxins from grain involves the use of a high concentration
- alcohol-in-water solvent typically a 70%:30% (weightweight)
- methanokwater solvent although other components may be added in relatively small amounts in particular to adjust in a known manner the pH value of the solvent dependent on other process steps of a particular assay method.
- cereal samples were subjected to mycotoxin extraction using the internationally approved methanokwater (70:30 by weight) and using an ethanol:water (30:70 by weight) solvent according to the present invention.
- the extracts were then analysed using the same analysis method to determine the amounts of specific mycotoxin present in the extract.
- the DON extract was filtered through filter-paper and cleaned in a solid phase extraction column, such as the MultiSep column which is available from Romer Labs Diagnostic GmbH of TuIIn Austria. Acetonitrile from the extract was evaporated; the extract then diluted with water and cleaned through an IAC. The analyte was eluted using methanol and analysed using a standard HPLC-ultra violet (UV) arrangement.
- a solid phase extraction column such as the MultiSep column which is available from Romer Labs Diagnostic GmbH of TuIIn Austria.
- Acetonitrile from the extract was evaporated; the extract then diluted with water and cleaned through an IAC.
- the analyte was eluted using methanol and analysed using a standard HPLC-ultra violet (UV) arrangement.
- the ZEA extract was filtered through filter-paper and diluted with a
Abstract
A method of extracting mycotoxins from a sample of cereal grains comprising recovering the mycotoxins from the sample by extraction using an ethanol:water solvent mixture constituted with ethanol present in an amount of between substantially 20% to 40% by weight, preferably between substantially 28% to 34% by weight and most preferably in an amount of substantially 30% by weight.
Description
Description
Method of Extracting Mycotoxins from Cereal Grains
[0001] The present invention relates to a method of extracting mycotoxins from cereal grains and in particular to a method of solvent extraction employing an alcohokwater based extraction solvent.
[0002] Mycotoxins tend to be very stable and may produce severe illness when ingested, inhaled, or introduced into the body by any other means. For instance, mycotoxins are known to be poisonous or carcinogenic when consumed by humans or animals. Mycotoxins are produced by molds and fungi during their growth on food and feed and may remain in food and feed long after the mold or fungus that produced them has died. Therefore products that are not visibly moldy or do not test positive for mold count can still contain potentially dangerous levels of mycotoxins.
[0003] Several countries have currently established or proposed regulations for control of mycotoxins (primarily the aflatoxins) in food and animal feed. In order to harmonize these regulations, the Food and Drug Administration, for example, has established guidelines for the levels of aflatoxin permitted in commodities for further processing. The permitted levels vary depending upon the intended end usage of the commodity. The European Union, for example, has also established regulations for the levels of ochratoxin A (OTA), Deoxynivalenol (DON); Zearalenone (ZON) and several other mycotoxins.
[0004] The enforcement of these regulations requires accurate monitoring of suspected commodities. However, since mycotoxins tend to be
inhomogeneously distributed throughout a lot of cereal it becomes prohibitively expensive to carry out laboratory analysis on the number of samples required to be representatitive of the particular lot. Therefore, there is a continuous need for a very simple, rapid and inexpensive method for detecting the presence of mycotoxins in a lot of cereal grain so that, a lot containing mycotoxins may be identified to allow further, more accurate analysis to be performed in a laboratory. Accordingly, it is highly desirable that in order to monitor potential food quality an assay for mycotoxins should be carried out 'in-field', generally outside of laboratory
conditions, such as in granaries, grain-trading and grain-processing businesses and even on farm, for example at grain silos before and during storage.
[0005] It is known, from for example US 2009 0081808 (Burmeister et al.) to
provide a method of and a device for rapid detection of mycotoxins which enable detection by relatively unskilled personnel in a simple rapid and inexpensive manner. The method employed is disclosed as requiring the extraction of the mycotoxin from the cereal grain sample using known solvent extraction methods involving an alcohol/water solvent comprised in a known manner.
[0006] Solvent extraction is a vital step in most detection methodologies. If
extraction is unable to be performed reliably then the results from the analysis will be unreliable. Indeed, within the European Union there is no specific determination method requirement, rather certain performance criteria are mandated (Currently Commission Regulation (EC) No
401/2006 of 23 February 2006).
[0007] One widely accepted method of efficiently and repeatably extracting
mycotoxins from grain involves the use of a high concentration
alcohol-in-water solvent, typically a 70%:30% (weightweight)
methanokwater solvent, although other components may be added in relatively small amounts in particular to adjust in a known manner the pH value of the solvent dependent on other process steps of a particular assay method.
[0008] However this solvent is highly flammable. For this reasons the 'in-field' adoption of simple mycotoxin detection devices may be resisted at least because of safety concerns relating to the solvent.
[0009] It is an aim of the present invention to provide a method of solvent
extraction of mycotoxin from cereal grain by which the above disadvantage is at least reduced.
[0010] This is achieved by a method according to claim 1 by which mycotoxin extraction from a cereal grain sample is achieved using a solvent comprising ethanol and water in which the ethanol is present in the region of between substantially 20% to 40% by weight, particularly between
substantially 28% to 34% by weight and most particularly at substantially 30% by weight.
[0011] Using ethanol in these concentrations provides a solvent which is not flammable but which still provides efficient extraction of mycotoxins from cereal grains.
[0012] It is generally appreciated that the efficacy of a solvent depends in part on the molecular size of the alcohol - as the size decreases the efficacy increases. Surprisingly then, since ethanol is a larger molecule than methanol it is been found by the inventor that the use of ethanol at concentrations much less than that used for methanol produces extraction efficiencies comparable to those of the known methanokwater (70:30) solvent when employed in the extraction of mycotoxins from cereal grains.
[0013] Comparison of mvcotoxin determinations
[0014] In order to test the extraction efficiency (Recovery) of the solvent
according to the present invention cereal samples were subjected to mycotoxin extraction using the internationally approved methanokwater (70:30 by weight) and using an ethanol:water (30:70 by weight) solvent according to the present invention. The extracts were then analysed using the same analysis method to determine the amounts of specific mycotoxin present in the extract.
[0015] Initially, a batch of malt was tested for the presence of OTA; DON; and
ZON. This was done by grinding 5Og of the sample to a maximum particle size of 1 mm; adding 250ml of acetonitrile:water (80:20) extraction solvent and shaking for 60 minutes in an orbital shaker at around 200rpm. The extract was then tested for the presence of the mycotoxins using the associated analysis methods described below. None of these mycotoxins were determined to be present in the malt batch.
[0016] Thereafter, three parallel samples from the batch were each spiked with a known amount of a different one of the three mycotoxins tested for above, see Table 1 for spiking levels. Extraction was again performed for sixty minutes (time not critical but selected to repeat the initial extraction conditions) in an orbital shaker at around 200 rpm in essentially the same manner each time but with different extraction solvents as indicated in
Table 1.
[0017] The OTA extract was filtered through filter-paper and diluted with a
phosphate buffered saline (PBS) buffer pH7,4/water (9+1). The filtered and diluted extract was then cleaned through an immu no-affinity column (IAC); the analyte eluted using methanol/acetic acid (98+2) and analysed using a standard High Performance Liquid Chromatography - fluorescence (HPLC-FI) arrangement.
[0018] The DON extract was filtered through filter-paper and cleaned in a solid phase extraction column, such as the MultiSep column which is available from Romer Labs Diagnostic GmbH of TuIIn Austria. Acetonitrile from the extract was evaporated; the extract then diluted with water and cleaned through an IAC. The analyte was eluted using methanol and analysed using a standard HPLC-ultra violet (UV) arrangement.
[0019] The ZEA extract was filtered through filter-paper and diluted with a
PBS-buffer ph7,4/water (2,5+50). The filtered and diluted extract was then cleaned through an IAC; the analyte eluted using acetonitrile and analysed using the standard HPLC-FI arrangement
[0020] The above was repeated with a further two sets of three samples and all of the analysis results are presented in Table 1 below together with the current official Swedish extraction efficiency requirements:
[0021]
Table 1
Extraction Mycotoxin Recovery (%)
(60 minutes in a OTA DON ZON
shaking device at (spiking level) (spiking level) (spiking level)
200 rpm) (2,59 ppb) (536 ppb) (55 ppb)
Methanokwater 97 84 71
(70:30)
Ethanokwater 97 107, 108 84, 94, 92 71 , 56, 59 (30:70)
Legal 70 - 110 70 - 120 70 - 120 requirements
[0022] From the above it can be readily determined that:
[0023] For OTA the mean recovery percentage is 104; the standard deviation is 6 and the rsd is 6;
[0024] For DON the mean recovery percentage is 90; the standard deviation is 5 and the rsd is 6; and
[0025] For ZON the mean recovery percentage is 63; the standard deviation is 8 and the rsd is 13;
[0026] It can be seen from Table 1 that the extraction efficiency of an extraction method using a solvent according to the present invention is substantially similar to that using the commonly employed methanokwater solvent.
[0027] It will be appreciated that the method according to the present invention is suitable for use in extracting other mycotoxins, such as T2-toxin and aflatoxins, from cereal grains and that it is intended that the scope of protection afforded to the invention is limited only by the wording of the claims and not by the exemplary comparative study provided above.
Claims
1. A method of extracting one or more mycotoxins from a sample of cereal grains comprising combining the sample with a solvent comprising an alcohol in water mixture characterised in that the solvent comprises a mixture constituted with ethanol present in an amount of between substantially 20% to 40% by weight.
2. A method as claimed in Claim 1 characterised in that the ethanol is present in an amount of between substantially 28% to 34% by weight.
3. A method as claimed in Claim 1 or Claim 2 characterised in that the ethanol is present in an amount of substantially 30% by weight.
4. A method according to any preceding claim characterised in that the
mycotoxins to be extracted are one or more selected from the group consisting of ochratoxin A (OTA), Deoxynivalenol (DON) and Zearalenone (ZON).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2009/061051 WO2011023230A1 (en) | 2009-08-27 | 2009-08-27 | Method of extracting mycotoxins from cereal grains |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2009/061051 WO2011023230A1 (en) | 2009-08-27 | 2009-08-27 | Method of extracting mycotoxins from cereal grains |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2011023230A1 true WO2011023230A1 (en) | 2011-03-03 |
Family
ID=41479241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2009/061051 WO2011023230A1 (en) | 2009-08-27 | 2009-08-27 | Method of extracting mycotoxins from cereal grains |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2011023230A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102313810A (en) * | 2011-07-29 | 2012-01-11 | 上海交通大学 | Chemiluminescent immunoassay method for rapidly detecting zearalenone toxin |
| ITMI20111788A1 (en) * | 2011-10-04 | 2013-04-05 | Giuseppe Arena | DECONTAMINATION TREATMENT PROCEDURE FOR DRIED FRUIT, SHELLFISH, CEREALS, VEGETABLES, SPICES, COFFEE AND OTHER OLEAGINOUS SEEDS FROM AFLATOSSINS AND / OR OTHER MICROCOSSINS AND PLANT TO IMPLEMENT THAT TREATMENT |
| WO2016063104A1 (en) | 2014-10-20 | 2016-04-28 | Foss Analytical A/S | Determination of analytes in a sample matrix by solvent extraction |
| CN111474335A (en) * | 2020-03-10 | 2020-07-31 | 安徽科杰粮保仓储设备有限公司 | Grain mycotoxin on-line detection method and device based on immunosensor |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102313810A (en) * | 2011-07-29 | 2012-01-11 | 上海交通大学 | Chemiluminescent immunoassay method for rapidly detecting zearalenone toxin |
| ITMI20111788A1 (en) * | 2011-10-04 | 2013-04-05 | Giuseppe Arena | DECONTAMINATION TREATMENT PROCEDURE FOR DRIED FRUIT, SHELLFISH, CEREALS, VEGETABLES, SPICES, COFFEE AND OTHER OLEAGINOUS SEEDS FROM AFLATOSSINS AND / OR OTHER MICROCOSSINS AND PLANT TO IMPLEMENT THAT TREATMENT |
| WO2016063104A1 (en) | 2014-10-20 | 2016-04-28 | Foss Analytical A/S | Determination of analytes in a sample matrix by solvent extraction |
| CN107110759A (en) * | 2014-10-20 | 2017-08-29 | 福斯分析仪器公司 | Pass through the analyte in solvent extraction determination sample matrix |
| US10545076B2 (en) | 2014-10-20 | 2020-01-28 | Foss Analytical A/S | Determination of analytes in a sample matrix by solvent extraction |
| CN111474335A (en) * | 2020-03-10 | 2020-07-31 | 安徽科杰粮保仓储设备有限公司 | Grain mycotoxin on-line detection method and device based on immunosensor |
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