CN109497506A - A kind of acrylamide natural inhibitor - Google Patents
A kind of acrylamide natural inhibitor Download PDFInfo
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- CN109497506A CN109497506A CN201811500401.8A CN201811500401A CN109497506A CN 109497506 A CN109497506 A CN 109497506A CN 201811500401 A CN201811500401 A CN 201811500401A CN 109497506 A CN109497506 A CN 109497506A
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- China
- Prior art keywords
- acrylamide
- water chestnut
- extract
- butyl alcohol
- concentration
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 239000003112 inhibitor Substances 0.000 title claims abstract description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000000284 extract Substances 0.000 claims abstract description 43
- 235000003283 Pachira macrocarpa Nutrition 0.000 claims abstract description 40
- 235000014364 Trapa natans Nutrition 0.000 claims abstract description 40
- 235000009165 saligot Nutrition 0.000 claims abstract description 40
- 241001083492 Trapa Species 0.000 claims abstract description 39
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 13
- 239000011149 active material Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 206010030113 Oedema Diseases 0.000 claims abstract 2
- 210000000952 spleen Anatomy 0.000 claims abstract 2
- 230000005764 inhibitory process Effects 0.000 claims description 16
- 239000003208 petroleum Substances 0.000 claims description 7
- 239000012259 ether extract Substances 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 claims 2
- 240000008867 Capsella bursa-pastoris Species 0.000 claims 2
- 238000010640 amide synthesis reaction Methods 0.000 claims 1
- 235000019684 potato crisps Nutrition 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 8
- 238000000605 extraction Methods 0.000 abstract description 4
- 244000285774 Cyperus esculentus Species 0.000 abstract description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000126 substance Substances 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229910001868 water Inorganic materials 0.000 description 16
- 239000000654 additive Substances 0.000 description 14
- 230000000996 additive effect Effects 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000010828 elution Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- -1 orcin glucoside Chemical class 0.000 description 8
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 5
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 5
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002203 pretreatment Methods 0.000 description 5
- 235000005875 quercetin Nutrition 0.000 description 5
- 229960001285 quercetin Drugs 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- GXAVBFNRWXCOPY-UHFFFAOYSA-N 1,4-dihydroxy-2,6-dimethoxybenzene Chemical compound COC1=CC(O)=CC(OC)=C1O GXAVBFNRWXCOPY-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 4
- 235000005487 catechin Nutrition 0.000 description 4
- 229950001002 cianidanol Drugs 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 3
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 3
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 3
- 235000012734 epicatechin Nutrition 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002021 butanolic extract Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000010829 isocratic elution Methods 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 235000012249 potassium ferrocyanide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- WBZPEZUBVIAKKS-UJPOAAIJSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol Chemical compound COC1=CC=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 WBZPEZUBVIAKKS-UJPOAAIJSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- 235000006226 Areca catechu Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 240000001085 Trapa natans Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000010675 chips/crisps Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000013575 mashed potatoes Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000000276 potassium ferrocyanide Substances 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000006920 protein precipitation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
-
- 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
Abstract
The invention discloses a kind of acrylamide natural inhibitors, the inhibitor is water chestnut active material, and the water chestnut active material is one of the total acetone extract of water chestnut skin 70%, water chestnut skin acetic acid ethyl ester extract, water chestnut skin n-butyl alcohol extract, water chestnut severe edema due to hypofunction of the spleen extract or a variety of mixtures.The water chestnut skin n-butyl alcohol extract was 25%, 55% or 95% ethanol eluate of macroreticular resin, and the optium concentration for inhibiting acrylamide to be formed is respectively as follows: 1.0 × 10‑5 mg/mL、1.0×10‑3 Mg/mL and 1.0 × 10‑3 mg/mL.Present invention extraction of chufa active material from water chestnut skin is formed for inhibiting potato crisp chip to bake process acrylamide, wherein n-butyl alcohol extract inhibiting effect is stronger, its 25% ethanol eluate of macroreticular resin inhibits acrylamide effect best, can be used for developing green, safe and efficient acrylamide natural inhibitor.
Description
Technical field
The present invention relates to food processing fields, and in particular to a kind of acrylamide natural inhibitor.
Background technique
Acrylamide be the few food of moisture content it is fried, the high temperature process such as bake during a kind of nuisance for generating
Matter.In order to reduce harm of the acrylamide to the mankind, the inhibition research that food processing process acrylamide is formed is nearly ten years
Hot spot concerned by people.Using plant extracts as additive inhibit food processing process in acrylamide formed research more by
To paying close attention to for numerous researchers.
Summary of the invention
To solve the above problems, the present invention provides a kind of acrylamide natural inhibitor, the extraction of chufa from water chestnut skin
Active material, the formation of acrylamide during effectively food being inhibited to bake.
To achieve the above object, the technical scheme adopted by the invention is as follows:
A kind of acrylamide natural inhibitor, the inhibitor are water chestnut active material；The water chestnut active matter
Matter is the total acetone extract of water chestnut skin 70%, water chestnut skin acetic acid ethyl ester extract, water chestnut skin n-butyl alcohol extract, water chestnut skin
One of water extract or a variety of mixtures.
Preferably, the water chestnut skin n-butyl alcohol extract was 25%, 55% or 95% ethanol eluate of macroreticular resin, suppression
The optium concentration that acrylamide processed is formed is respectively as follows: 1.0 × 10-5 mg/mL、1.0×10-3 Mg/mL and 1.0 × 10-3 mg/mL。
Further, the water chestnut skin n-butyl alcohol extract was 25% ethanol eluate of macroreticular resin, and optimal inhibition concentration is
1.0×10-5 mg/mL；Wherein, the n-butyl alcohol extract crosses the Isosorbide-5-Nitrae-dihydroxy contained in 25% ethanol eluate of macroreticular resin
Base -2,6- dimethoxy benzene -1-β- D- glucopyranoside is best to acrylamide formation inhibitory effect, and optimal inhibition concentration is
1.0×10-2 Mg/mL, inhibiting rate 32.81%.
Preferably, the water chestnut active material is water chestnut skin petroleum ether extract, and concentration is 1.0 × 10-7 mg/mL。
The invention has the following advantages:
Extraction of chufa active material is formed for inhibiting potato crisp chip to bake process acrylamide from water chestnut skin, wherein n-butanol
Extract inhibiting effect is stronger, and 25% ethanol eluate of macroreticular resin inhibits acrylamide effect best, can be used for developing green
Color, safe and efficient acrylamide natural inhibitor.
Detailed description of the invention
Fig. 1 is acrylamide standard curve.
Fig. 2 is acrylamide high-efficient liquid phase chromatogram in potato crisp chip sample.
Fig. 3 is the high-efficient liquid phase chromatogram (1.25 μ g/mL) of acrylamide standard items.
Fig. 4 is the influence that the additive of various concentration forms acrylamide.
Fig. 5 is inhibitory effect of the various concentration additive to acrylamide in potato crisp chip.
Fig. 6 is that the initial gross separation of n-butanol portion purifies process.
Fig. 7 is the effect that ethanol eluate inhibits acrylamide to be formed.
Fig. 8 is inhibiting rate of the ethanol eluate additive to acrylamide of various concentration.
Fig. 9 is that 25% ethanol eluate is partially separated flow chart.
Figure 10 is that Fr.1.1 is partially separated flow chart.
Figure 11 is that Fr.1.1.3 is partially separated flow chart.
Figure 12 is the chemical formula of compound 1..
Figure 13 is the chemical formula of compound 2..
Figure 14 is the chemical formula of compound 3..
Figure 15 is the chemical formula of compound 4..
Figure 16 is the chemical formula of compound 5..
Figure 17 is the effect that various concentration additive inhibits acrylamide to be formed.
Figure 18 is inhibiting rate of the various concentration additive to acrylamide.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.Following embodiment will be helpful to the technology of this field
Personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the ordinary skill of this field
For personnel, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to the present invention
Protection scope.
Embodiment 1
Potato crisp chip baking temperature is 160 DEG C in the present embodiment, and baking times are 5 min.
70% acetone total extract of water chestnut skin and petroleum ether layer, ethyl acetate layer, n-butanol layer and water layer extract are used super
It is 1.0,1.0 × 10 that pure water is configured to concentration respectively-1、1.0×10-2、1.0×10-3、1.0×10-5、1.0×10-7、1.0×
10-9Each 10.0 mL of the dilution of mg/mL is spare.
The analysis method of 1.1 acrylamides
Referring to the acrylamide analysis method that Cai Wen is established, high-efficient liquid phase chromatogram condition is chromatographic column: reverse phase C-18 column；Flowing
Phase: methanol: water (v:v, 5:95)；Detector: DAD detector；Sample volume: 10.0 μ L；Detection wavelength: 210 nm；Flow velocity: 0.6
mL/min；Column temperature: 30 DEG C.
The drafting of the standard curve of 1.2 acrylamides
(1) CarrezI reagent: 15.00 g potassium ferrocyanides are weighed and are dissolved in 100 mL ultrapure waters；CarrezII reagent: it weighs
30.00 g zinc sulfate are dissolved in 100 mL ultrapure waters.
(2) it takes 0.0050 g acrylamide standard items to be dissolved in aqueous solution of 50 mL containing 5% methanol, obtains 100 μ g/mL
Acrylamide standard reserving solution, it is stand-by as 4 DEG C of refrigerators.
(3) by the standard reserving solution prepared with ultrapure water be diluted to concentration be 10.0,5.0,2.5,1.25,0.625,
The series of standards liquid of 0.3125 μ g/mL carries out HPLC analysis using chromatographic condition described in acrylamide analysis method.
Made axis of abscissas (X) with the mass concentration of standard sample, corresponding peak area is axis of ordinates (Y), draws the range of linearity and exists
The standard curve of 0.3125 μ of μ g/mL~10.0 g/mL, acquires equation of linear regression with this.
It is 10.0,5.0,2.5,1.25,0.625,0.3125 μ g/ that the standard reserving solution prepared in (2), which is diluted to concentration,
The standard solution of mL.HPLC measurement is carried out according to chromatographic condition described in acrylamide analysis method, makes peak area to dense
The standard curve of degree obtains linear regression equation y=63032x-1240.3, R2=0.9998 .The result shows that in 0.3125 μ g/
Linear dependence is good in the concentration range of the μ of mL~10.0 g/mL.
The preparation of 1.3 potato crisp chip samples
Totally 36 parts of 2.00 g of every part of mealy potato that drying to constant weight are weighed, prepared water chestnut is separately added into (3) of 3.2.3
The dilution 1.1 of the various concentration of each layer extract liquor such as 70% acetone total extract of skin and petroleum ether, ethyl acetate, n-butanol, water
ML, blank control group are added ultrapure water and the face of equivalent, claim the 1.60 uniform press-in dies of g mashed potatoes, and 1 mm of thickness, straight is made
The disk of 4 cm of diameter is put into and extracts preheated baking oven, at 160 DEG C of temperature, takes out cooling rapidly after baking 5 min, obtains
Potato crisp chip sample, every 1.12 g of tablet quality.
1.4 sample pre-treatments
During baking potato chips, the pre-treatment step of sample is as follows:
(1) it grinds: 1.12 g potato crisp chips being ground into fine powder with mortar, are poured into beaker.
(2) it extracts and removes protein: 3.5 mL ultrapure waters are added and extract acrylamide, then are separately added into protein precipitation
15% potassium ferrocyanide of agent, 1.0 mL and molten 1.0 mL of 30% zinc sulfate, at room temperature 660 r/min magnetic agitation, 5 min, then 4000
R/min is centrifuged 20 min, obtains 2.5 mL of supernatant.
(3) it cleans: taking 0.5 mL of supernatant, cross C18 solid phase extraction column, with the ultrapure water elution of 1.5 mL, collect elution
Liquid crosses 0.45 μm of water system syringe-type miillpore filter, measures acrylamide chromatographic peak area by the method for 3.2.4.Every group real in parallel
It tests 3 times.
The chromatogram of potato crisp chip and acrylamide mark product compares
As seen from Figure 3, the high-efficient liquid phase color spectral peak peak shape of acrylamide standard items is good, and retention time is 8.50 min.Fig. 2 is
Potato crisp chip at 160 DEG C after roasted 5 min carries out HPLC analysis according to chromatographic condition described in acrylamide analysis method
The chromatogram of acrylamide content is detected, Fig. 3 is the high-efficient liquid phase chromatogram of acrylamide mark product under the same conditions, by figure
The comparison of 2 and Fig. 3 is as it can be seen that acrylamide mark product appearance time is 8.50 min, corresponding chromatographic peak visual target peak peak in Fig. 2
Type is good, and acrylamide peak can separate well with other miscellaneous peaks, this sample method and condition are third suitable for potato crisp chip
The detection of acrylamide content.
The effect that various concentration additive inhibits acrylamide to be formed
Each layer extract such as 70% acetone extract of water chestnut skin and petroleum ether, ethyl acetate, n-butanol, water respectively with 1.0,1.0
×10-1、1.0×10-2、1.0×10-3、1.0×10-5、1.0×10-7、1.0×10-9The concentration of mg/mL is respectively added to soil
In bean powder (blank control group adds distilled water), 5 min are baked at 160 DEG C, potato crisp chip is made, carry out sample according still further to 1.4
Pre-treatment, then chromatographic condition described in acrylamide analysis method carries out propylene in HPLC analysis detection potato crisp chip sample
The content of amide, is as a result shown in Fig. 4.
As shown in Figure 4,70% acetone total extract of water chestnut skin and its opposed polarity solvent extract are added native as additive
The formation for baking process acrylamide to potato crisp chip in bean powder has inhibiting effect, and there are certain dosage effects for inhibitory effect
Relationship, but in non-existing linear relationship.When additive be in low concentration of water it is flat when, each additive to acrylamide have inhibition make
With wherein 70% acetone total extract, acetic acid ethyl ester extract, n-butyl alcohol extract, water extract are 1.0 × 10-9~1.0 ×
10-3In the concentration range of mg/mL, acrylamide inhibition increases with the increase of concentration, until inhibiting rate reaches maximum value；But
More than 1.0 × 10-3After mg/mL concentration level, with the increase of additive concentration, occurs inhibiting rate instead and be gradually reduced, very
The phenomenon that promoting acrylamide formation to appearance.And petroleum ether extract is 1.0 × 10-9~1.0 × 10-7Mg/mL concentration model
In enclosing, concentration is positively correlated with acrylamide inhibiting rate, until inhibiting rate reaches maximum value；But more than 1.0 × 10-7Mg/mL is dense
After degree is horizontal, with the increase of additive concentration, above-mentioned similar phenomenon is also presented.In 70% acetone total extract of water chestnut skin, petroleum
Ether extract, acetic acid ethyl ester extract, n-butyl alcohol extract, in water extract, inhibition of the n-butyl alcohol extract to acrylamide
Effect is best, and optimal inhibition concentration is 1.0 × 10-3When mg/mL, inhibiting rate reaches 17.14%.
Embodiment 2
(1) experimental raw: the butanol extraction liquid of water chestnut active material is made by oneself to obtain by this laboratory；D101 type macroreticular resin
(scrutiny institute is recovered in Tianjin)；Heavy duty detergent tlc silica gel (Qingdao Haiyang).
Macroporous resin purification n-butyl alcohol extract
Methanol is added into n-butyl alcohol extract to being completely dissolved, sample is mixed with the macroreticular resin D101 of 3 times of extract quality, by first
Alcohol evaporates into dry, dress column.Eluted respectively with 25%, 55%, 95% volumetric concentration ethyl alcohol, after concentration respectively 15.09 g,
4.58 g,1.45 g.The specific flow chart that extracts is shown in Fig. 6.
The effect that opposed polarity eluent inhibits acrylamide to be formed
After the concentration of macroreticular resin eluent, being configured to concentration respectively is 1.0,1.0 × 10-1、1.0×10-2、1.0×10-3、
1.0×10-5、1.0×10-7、1.0×10-9The dilution of mg/mL is spare.Separately take respectively the above various concentration 25%, 55%,
Each 1.1 mL of 95% ethanol eluate is added in mealy potato (blank control group adds distilled water) and according to 1.3 methods prepares potato
Crisp chip cools down rapidly after baking 5 min at 160 DEG C, sample pre-treatments is carried out according to 1.4, in acrylamide analysis method
The chromatographic condition carries out HPLC detection, surveys the content of acrylamide in potato crisp chip, as a result sees Fig. 7, Fig. 8.
By Fig. 7, Fig. 8 it is found that different concentration ethanol eluent has suppression effect to the formation of acrylamide in potato crisp chip,
Wherein the optimal inhibition concentration of 25% ethanol eluate is 1.0 × 10-5 Mg/mL, inhibiting rate 24.69%, and 55% and 95%
The optimal inhibition concentration of ethanol eluate be respectively 1.0 × 10-3Mg/mL, inhibiting rate are respectively 3.91% and 15.44%, can
See that 25% ethanol eluate is better than 55%, 95% ethanol eluate to the inhibitory effect of acrylamide, and its inhibiting rate compares n-butanol
Extract it is high by 44.04%, it can be seen that the isolating and purifying of water chestnut bark extract facilitates potato crisp chip and bakes process acryloyl
The raising of amine inhibiting rate, this naturally presses down to separate more efficient acrylamide from 25% ethanol eluate in next step
Preparation provides scientific basis.
Embodiment 3
Experimental raw and reagent
(1) experimental material: n-butyl alcohol extract crosses 25% ethanol eluate after macroreticular resin；1. compound is orcin grape
2. glucosides, compound are 1,4- dihydroxy -2,6- dimethoxy benzene -1-β3.-D- glucopyranoside, compound are L- color ammonia
4. acid, compound are 2,4- dihydroxy -3- methylbenzene -2-β5.-D- glucopyranoside, compound are 1,4- dihydroxy -3- first
Oxygroup benzene -4-β- D- glucopyranoside；Chromatographic grade Quercetin (Shanghai Yuan Ye Biotechnology Co., Ltd)；Chromatographic grade table catechu
Element (Chinese pharmaceutical biological product identifies institute)；Chromatographic grade catechin (Chinese food drug identification research institute)；C18, gel (Germany
Merck)；Tlc silica gel, column chromatography silica gel (Qingdao Haiyang).
Experimental method
It is 1. orcin glucoside, compound compound is 2. 1,4- dihydroxy -2,6- dimethoxy benzene -1-β- D- pyrans
3. glucoside, compound are 4. L-Trp, compound are 2,4- dihydroxy -3- methylbenzene -2-β- D- glucopyranoside,
5. compound is 1,4- dihydroxy -3- methoxybenzene -4-β- D- glucopyranoside and Quercetin, tea element, epicatechin three
A standard items, being configured to concentration respectively is 1.0,1.0 × 10-1、1.0×10-2、1.0×10-3、1.0×10-5、1.0×10-7、
1.0×10-9Each 10.0 mL of the dilution of mg/mL is spare.Potato crisp chip is prepared according to 1.3 methods, bakes 5 at 160 DEG C
It is cooled down rapidly after min, carries out sample pre-treatments according to 1.4, with the progress of chromatographic condition described in acrylamide analysis method
HPLC detection, surveys the content of acrylamide in potato crisp chip.
As a result with analysis
Water chestnut activated monomer isolates and purifies
Eluent Fr1(15.09 g of 25% volumetric concentration ethyl alcohol) through RP-C18Column, silicagel column, partly prepares efficient liquid at gel column
Mutually further isolate and purify.H2O:MeOH (90:10 → 85:15 → 80:20 → 85:25) carries out gradient elution, respectively obtains
Fr1.1(3.41 g),Fr1.2(4.45 g),Fr1.3(4.51 g),Fr1.4(0.34 g).Its separation process is shown in Fig. 9.
Fr1.1 (3.41 g) obtains Fr.1.1.1 (230 mg), Fr.1.1.2 through positive thin-layer chromatography combining data detection
(890 mg),Fr.1.1.3 (910 mg),Fr.1.1.4 (68 mg).Its separation process is shown in Figure 10.
Fr1.1.3 (910 mg) by reversely be partly prepared Fr.1.1.3.1 (74 mg), Fr.1.1.3.2 (17 mg),
Fr.1.1.3.3 (56 mg).Its separation process is shown in Figure 11.
(1) Fr.1.1.1 component (230 mg) is dissolved with methanol, with half preparative high-performance liquid chromatographic instrument of reverse phase
(C18 column) is separated, and in the case where ultraviolet wavelength is 210 nm, uses H2O:MeOH (95:5), flow velocity are that 2 mL/min carry out waiting ladders
Degree elution, the min of tr=87 obtain compound 1. (17 mg).The min of tr=25 obtains compound 2. (22 mg).
(2) Fr.1.1.2 component (890 mg) is dissolved with methanol, crosses gel column and is eluted with 100% methanol,
56 mg are obtained, then are separated with half preparative high-performance liquid chromatographic instrument of reverse phase (C18 column), in the case where ultraviolet wavelength is 210 nm, are used
H2O:MeOH (95:5), flow velocity are that 2 mL/min carry out Gradient elution, obtain compound 3. (4 mg).
(3) Fr.1.1.3 component (910 mg) is dissolved with methanol, with half preparative high-performance liquid chromatographic instrument of reverse phase
(C18 column) is separated, and in the case where ultraviolet wavelength is 210 nm, uses H2O:MeOH (95:5), flow velocity are that 2 mL/min carry out waiting ladders
Degree elution, obtains Fr.1.1.3.1 (74 mg), Fr.1.1.3.2 (17 mg), Fr.1.1.3.3 (56 mg).Fr.1.1.3.1 mistake
Silicagel column PE:EA (50:50) carries out isocratic elution and obtains 48 mg, then with half preparative high-performance liquid chromatographic instrument of reverse phase (C18 column) into
Row separation uses H in the case where ultraviolet wavelength is 210 nm2O:MeOH (95:5), flow velocity are that 2 mL/min progress Gradient elution must be changed
Close object 4. (36 mg)；Fr.1.1.3.2, which crosses silicagel column PE:EA (50:50) and carries out isocratic elution, to be obtained compound 8. (6 mg) no
It is pure；Fr.1.1.3.3 is separated with half preparative high-performance liquid chromatographic instrument of reverse phase (C18 column), in the case where ultraviolet wavelength is 210 nm,
Use H2O:MeOH (95:5), flow velocity are that 1.5 mL/min carry out Gradient elution, and obtaining compound, 5. (3 mg), compound be 6.
(1.3 mg).
(4) Fr.1.1.4 component (68 mg) is dissolved with methanol, with half preparative high-performance liquid chromatographic instrument of reverse phase
(C18 column) is separated, and in the case where ultraviolet wavelength is 210 nm, uses H2O:MeOH (95:5), flow velocity are that 2 mL/min carry out waiting ladders
Degree elution, obtains compound 7. (0.8 mg).
The Structural Identification of water chestnut activated monomer
Compound is 1.: 17 mg, colorless crystalline, are soluble in methanol by m.p.:132-133 DEG C.
?1H-NMR(400 MHz, CD3OD) in spectrogram, by chemical shiftδ H6.42 ppm(1H,s),δ H 6.37
Ppm(1H,s),δ H6.30 ppm(1H,s), deducibility compound 1. in have one 1,3,5- trisubstituted phenyl ring knots
Structure, as shown in figure 12.Chemical shiftδ H2.22 ppm(3H,s), it is methyl hydrogen signal, chemical shiftδ H 3.26-3.43 ppm
(4H,m) be sugar chain on proton signal.
?13C-NMR(101 MHz, CD3OD in), by chemical shiftδ C 160.1, 159.2, 141.3, 111.2,
109.8,102.2,102.1 ppm, preliminary judgement is with the presence of phenyl ring, chemical shiftδ C 21.64 ppm are methyl carbon signal.
Compound 1. orcin glucoside, molecular formula are determined that it is through consulting related data by above-mentioned analysis
Are as follows: C13H18O7, relative molecular mass 286.
Compound is 2.: 22 mg, amorphous solid, are dissolved in dimethyl sulfoxide by m.p.:214-216 DEG C.
?1H-NMR(400 MHz, DMSO-d 6) in spectrogram, by chemical shiftδ H6.06 ppm(2H,s), deducibility
Closing has one 1 in object 2,3,4,5- quaternary phenyl ring, such as Figure 13.Chemical shiftδ H3.68 ppm(6H,s), illustrate the change
Object is closed there are two methoxyl group and is in symmetric position.
?13C-NMR(101 MHz, DMSO-d6) in, by chemical shift δ C 153.9,153.2,153.2,127.5,
103.5,93.8,93.8 ppm, with the presence of phenyl ring, 56.14 ppm of chemical shift δ C is methoxyl group signal for preliminary judgement.δC
106.48 ppm are the end carbon signal of sugar.
Compound is 3.: 4 mg, faint yellow solid, are dissolved in diluted acid diluted alkaline by m.p:289 DEG C.
?1H-NMR (400 MHZ,DMSO-d 6) in spectrogram, by chemical shiftδ H 7.56 (1H, d, J=7.8 Hz),
6.97 (1H, t,J=7.3 Hz), 7.06 (1H,t,J=7.3Hz,), 7.34 (1H,d,J=8.0Hz), it is known that in compound
Containing 1,2- disubstituted benzenes ring, 7.20 (1H,s) illustrate there is alkene.
?13C-NMR(101 MHz, DMSO-d 6) in, by chemical shiftδ C124.1, 109.6, 118.3, 118.5,
120.7,111.3,136.4,127.3 ppm explanation has phenyl ring,δ C170.3 ppm, illustrate there is carbonyl.
Compound 3. L-Trp, molecular formula are determined that it is through consulting related data by above-mentioned analysis are as follows:
C11Hl2N2O2, relative molecular mass 204.
Compound is 4.: 36 mg, amorphous solid are soluble in methanol.
?1H-NMR(400 MHz, CD3OD) in spectrogram, by chemical shiftδ H6.28 ppm(1H,s),δ H 6.25-
6.21 ppm(2H,s), deducibility compound 4. in have a trisubstituted phenyl ring.Chemical shiftδ H2.16 ppm(3H,s)
Position methyl hydrogen signal.
?13C-NMR(101 MHz, CD3OD in), by chemical shiftδ C168.1, 167.6, 148.8, 119.3, 117.4,
110.4 ppm are the carbon signal on aromatic rings, chemical shiftδ C30.9 ppm are methyl carbon signals.Chemical shiftδ C 110.08
Ppm is the end carbon signal of sugar, structure such as Fig. 5-7.
By HMBC map it is found thatδ H6.28 ppm withδ C167.6 andδ C148.2 havingJ 2 Relationship, withδ C 168.1、δ C
119.3 havingJ 3 Relationship.δ H6.24 ppm withδ C117.4 andδ C167.6 havingJ 2 Relationship, withδ C 110.4、δ C168.1 havingJ 3It closes
System.δ H6.22 ppm withδ C119.3 andδ C168.1 havingJ 2 Relationship, withδ C148.8 andδ C167.6 havingJ 3 Relationship.By upper
The analysis stated is it is found that 4. compound is 2,4- dihydroxy -3- methylbenzene -2-β- D- glucopyranoside.
Compound is 5.: 3 mg, colorless amorphous powder are dissolved in dimethyl sulfoxide.
?13C-NMR(101 MHz, DMSO-d 6) in, by chemical shiftδ C 147.8, 107.9, 151.0, 152.4,
115.2,107.9,102.5,74.7,74.7,70.4,99.8,67.3,55.5 ppm, preliminary judgement have phenyl ring to deposit
In chemical shiftδ C 55.5 ppm are methoxyl group signal.δ C 107.9 ppm are the end carbon signal of sugar.
Isosorbide-5-Nitrae-dihydroxy -3- methoxybenzene -4- is determined that it is through consulting related data by above-mentioned analysisβ- D- pyrrole
Glucopyranoside glycosides, relative molecular mass 298.
The comparison that water chestnut activated monomer and flavones inhibit acrylamide to be formed
As shown in Figure 14, compound 1., 2., 3., 4., 5. and Quercetin, epicatechin, catechin as additive be added soil
There are inhibiting effect, but these additive concentration and acryloyl to the formation of acrylamide in potato crisp chip soybean in bean powder
It is in non-linear relation between amine content.Found out by Figure 17, Figure 18, compound 1., 2., 3., 4., 5. and Quercetin, table
In theine, catechin, compound 1., compound 4., the optimal inhibition concentration of Quercetin, catechin be 1.0 × 10-3 Mg/mL,
Reaching maximal percentage inhibition at this time is respectively 30.24%, 30.53%, 25.98%, 24.9%, and compound 2., compound 3., compound
5., the optimal inhibition concentration of epicatechin be 1.0 × 10-2 Mg/mL, reach at this time maximal percentage inhibition be respectively 32.81%,
18.64%,28.18%,24.9%.Compound 1., 2., 4., 5. preferable to acrylamide inhibitory effect, and compound 2. > chemical combination
4. 1. > compound is 5. for > compound for object；Compound is 2. best to the inhibitory effect of acrylamide, i.e., optimal inhibition concentration is 1.0
×10-2When mg/mL, inhibiting rate reaches 32.81%.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make a variety of changes or modify within the scope of the claims, this not shadow
Ring substantive content of the invention.In the absence of conflict, the feature in embodiments herein and embodiment can any phase
Mutually combination.
Claims (6)
1. a kind of acrylamide natural inhibitor, it is characterised in that: the inhibitor is water chestnut active material.
2. a kind of acrylamide natural inhibitor as described in claim 1, it is characterised in that: the water chestnut
Shepherd's purse active material is the total acetone extract of water chestnut skin 70%, water chestnut skin acetic acid ethyl ester extract, water chestnut skin extracting n-butyl alcohol
One of object, water chestnut severe edema due to hypofunction of the spleen extract or a variety of mixtures.
3. a kind of acrylamide natural inhibitor as claimed in claim 2, it is characterised in that: the water chestnut skin extracting n-butyl alcohol
Object was 25%, 55% or 95% ethanol eluate of macroreticular resin, the optium concentration for inhibiting acrylamide to be formed is respectively as follows: 1.0 ×
10-5 mg/mL、1.0×10-3 Mg/mL and 1.0 × 10-3 mg/mL。
4. a kind of acrylamide natural inhibitor as claimed in claim 3, it is characterised in that: the water chestnut skin extracting n-butyl alcohol
Object was 25% ethanol eluate of macroreticular resin, and optimal inhibition concentration is 1.0 × 10-5 mg/mL。
5. a kind of acrylamide natural inhibitor as claimed in claim 4, it is characterised in that: the n-butyl alcohol extract is excessive
1,4- dihydroxy -2,6- dimethoxy benzene-the 1- contained in 25% ethanol eluate of hole resinβ- D- glucopyranoside is to propylene
Amide formation inhibitory effect is best, and optimal inhibition concentration is 1.0 × 10-2 Mg/mL, inhibiting rate 32.81%.
6. a kind of acrylamide natural inhibitor as described in claim 1, it is characterised in that: the water chestnut
Shepherd's purse active material is water chestnut skin petroleum ether extract, and concentration is 1.0 × 10-7 mg/mL。
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| CN110574911A (en) * | 2019-11-07 | 2019-12-17 | 贺州学院 | Water chestnut skin extract and application thereof |
| CN113209077A (en) * | 2021-05-15 | 2021-08-06 | 西北农林科技大学 | Application of quercetin compounds in protection of hepatotoxicity caused by acrylamide |
| CN113349344A (en) * | 2021-05-08 | 2021-09-07 | 西北农林科技大学 | Processing method capable of inhibiting acrylamide content in high-temperature roasted beef balls |
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| CN104557835A (en) * | 2014-12-29 | 2015-04-29 | 贺州学院 | Method for extracting eleocharin D from eleocharis tuberosa peels |
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| CN104557835A (en) * | 2014-12-29 | 2015-04-29 | 贺州学院 | Method for extracting eleocharin D from eleocharis tuberosa peels |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110574911A (en) * | 2019-11-07 | 2019-12-17 | 贺州学院 | Water chestnut skin extract and application thereof |
| CN113349344A (en) * | 2021-05-08 | 2021-09-07 | 西北农林科技大学 | Processing method capable of inhibiting acrylamide content in high-temperature roasted beef balls |
| CN113209077A (en) * | 2021-05-15 | 2021-08-06 | 西北农林科技大学 | Application of quercetin compounds in protection of hepatotoxicity caused by acrylamide |
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