CN105918772A - Class-I carboxymethyl lysine removing agent and application thereof - Google Patents
Class-I carboxymethyl lysine removing agent and application thereof Download PDFInfo
- Publication number
- CN105918772A CN105918772A CN201610375742.1A CN201610375742A CN105918772A CN 105918772 A CN105918772 A CN 105918772A CN 201610375742 A CN201610375742 A CN 201610375742A CN 105918772 A CN105918772 A CN 105918772A
- Authority
- CN
- China
- Prior art keywords
- cml
- application
- remover
- food
- quinones
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- RRUYWEMUWIRRNB-LURJTMIESA-N (2s)-6-amino-2-[carboxy(methyl)amino]hexanoic acid Chemical compound OC(=O)N(C)[C@H](C(O)=O)CCCCN RRUYWEMUWIRRNB-LURJTMIESA-N 0.000 title claims abstract description 59
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 8
- 235000013305 food Nutrition 0.000 claims abstract description 32
- 150000004053 quinones Chemical group 0.000 claims abstract description 23
- 239000000126 substance Substances 0.000 claims abstract description 19
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 18
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallyl group Chemical group C1(=C(C(=CC=C1)O)O)O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 7
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 7
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Chemical group C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 claims description 14
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Chemical group Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 claims description 14
- 235000012734 epicatechin Nutrition 0.000 claims description 14
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 11
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical group C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims description 10
- -1 table GC Chemical compound 0.000 claims description 9
- 239000004472 Lysine Substances 0.000 claims description 8
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical group C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Chemical group OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 6
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 4
- 102000030523 Catechol oxidase Human genes 0.000 claims description 4
- 108010031396 Catechol oxidase Proteins 0.000 claims description 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Chemical group 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 claims description 4
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Chemical group C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 4
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims description 4
- 235000005875 quercetin Nutrition 0.000 claims description 4
- 229960001285 quercetin Drugs 0.000 claims description 4
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims description 4
- 235000005493 rutin Nutrition 0.000 claims description 4
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims description 4
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims description 4
- 229960004555 rutoside Drugs 0.000 claims description 4
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical group OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 4
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical group O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims description 3
- 229940079877 pyrogallol Drugs 0.000 claims description 3
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Chemical group OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 150000001557 benzodiazepines Chemical group 0.000 claims description 2
- 235000004883 caffeic acid Nutrition 0.000 claims description 2
- 229940074360 caffeic acid Drugs 0.000 claims description 2
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Chemical group OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims description 2
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000009498 luteolin Nutrition 0.000 claims description 2
- 235000013372 meat Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical group C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims 2
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Chemical group OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Chemical group OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 claims 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 abstract description 25
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 230000007935 neutral effect Effects 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 10
- 229940030275 epigallocatechin gallate Drugs 0.000 description 10
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 9
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000008363 phosphate buffer Substances 0.000 description 8
- 230000001629 suppression Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000001471 micro-filtration Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- NKQPRNDTEUZYKT-UHFFFAOYSA-N cyclohex-5-ene-1,2,3,4-tetrone Chemical group O=C1C=CC(=O)C(=O)C1=O NKQPRNDTEUZYKT-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000001972 liquid chromatography-electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000006199 nebulizer Substances 0.000 description 4
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 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 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 238000002013 hydrophilic interaction chromatography Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010007558 Cardiac failure chronic Diseases 0.000 description 1
- QRYRORQUOLYVBU-VBKZILBWSA-N Carnosic acid Natural products CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 description 1
- 108010087806 Carnosine Proteins 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 206010027336 Menstruation delayed Diseases 0.000 description 1
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 235000009392 Vitis Nutrition 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 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
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 description 1
- 229940044199 carnosine Drugs 0.000 description 1
- 239000001551 castor spp. extract Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C7/00—Other dairy technology
- A23C7/04—Removing unwanted substances other than lactose or milk proteins from milk
- A23C7/043—Removing unwanted substances other than lactose or milk proteins from milk using chemicals in liquid or solid state, e.g. flocculating, adsorbing or extracting agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention discloses a class-I carboxymethyl lysine removing agent and application thereof. The removing agent is a quinones substance formed by the oxidization of polyphenol containing a catechol or pyrogallol structure unit. The removing agent is applied to the reduction of the content of carboxymethyl lysine in a food system. The quinones substance has stronger capability of removing AGEs (Advanced Glycation End Products) in the food system of which the pH is neutral or alkaline, and when the quinones substance is added after the food system generates the CML or before the CML is generated, the level of the CML in the system can be effectively reduced.
Description
Technical field
The present invention relates to food processing field, be specifically related to carboxymethyl lysine (CML) and eliminate system
Agent, can reduce the content of the CML generated in food system, as food by capture CML
Additive and extensively utilize.
Background technology
Advanced glycosylation end products (AGEs) is to be produced late period at Maillard reaction by food or organism
A highly oxidized compound of class.Now there are some researches show, AGEs may be with diabetes, chronic heart failure
Exhaust, the generation of the disease such as atherosclerosis relevant to development.Food-borne AGEs is absorbed into via digestive tract
Enter human body, human body AGEs level will be promoted.Long-term food-borne AGEs taking in excess, the most free
State AGEs (glycated amino acid), will cause potential health hazard to human body.
The generation of the means of existing minimizing AGEs content predominantly suppression AGEs: 1) antioxidant, energy
Removing system free radical, the process that suppression is converted to AGEs by the Amadori product of free radical mediated, such as:
VE, rutin, ferulic acid, VC, Quercetin, carnosine etc.；2) dicarbonyl compound trapping agent, can capture
The intermediate product Biformyl of AGEs formation and then the formation of suppression AGEs, such as: aminoguanidine (AG), pyrrole
Tremble amine (VB6) etc.；3) amino competitor, can be with the ammonia on lysine containing amino in its molecular structure
There is Maillard reaction, and then the generation of suppression AGEs in base competition, such as: VB1And derivant (thiamine
Element phosplate, TPP) etc..
As a example by typical case's AGEs carboxymethyl-lysine (CML), existing inhibitor reduces system CML and contains
The possible path of amount, therefore need to be at body as it is shown in figure 1, be the suppression to the part path forming CML
System adds inhibitor before forming CML and can be only achieved the effect reducing CML level.In actual production,
Inhibitor adds the AGEs that front food system has contained certain level, and existing inhibitor cannot be complete
The generation (suppression ratio is about 10%-50%) of full inhibition system AGEs, but, in food system
The AGEs existed, existing means will be unable to eliminate.
Currently there are no and be specifically designed in food the research that existing AGEs eliminates, the most AGEs is not eliminated
Agent is applied to the report in food processing.
Summary of the invention
For solving the problems referred to above, it is an object of the invention to provide a class CML remover, be specifically related to contain
The quinones substance that the polyphenol oxidase of catechol or pyrogallol structure is formed is to CML in simulated foods system
Elimination effect.Remover can be had CML by capture system under certain condition and then be reached CML
The purpose eliminated, its capture principle is as shown in Figure 2.
The purpose of the present invention is achieved through the following technical solutions:
Carboxymethyl lysine remover, described remover is containing catechol or pyrogallol structure list
The quinones substance that the polyphenol oxidase of unit is formed.
Described polyphenol includes 4-methyl pyrocatechol, epicatechin, L-Epicatechin gallate, coffee
Acid, Quercetin, epigallocatechin gallate (EGCG), table GC, luteolin, rutin.
The application in terms of reducing food system carboxymethyl-lysine content of the described remover.
In food system, add described remover, control pH >=7 of system.Preferably, described system
PH is 8.
The reaction temperature of described system is 25-100 DEG C.
The addition of described remover is the 2-3% of system lysine content.
Described remover adds after food system does not generates or generated CML.
Wherein said food system includes milk product, grain and goods thereof, flavoring agent, meat and goods thereof, tank
Head goods.
The present invention, in simulated foods system (glu-lysine system), utilizes liquid chromatography tandem matter
The quinones that polyphenol containing catechol or pyrogallol construction unit is formed by spectrometry (LC-MS/MS)
Material and CML add and thing is identified.Stability according to the quinones substance formed can be divided into:
Stablize quinones substance and be easily polymerized quinones substance two class.
Described stablize quinones substance add with CML and product identify concretely comprise the following steps:
(1) it is 10mM, quinones substance with phosphate buffer (pH 7.0) the preparation CML of 0.2M
Solution for 1mM；
(2) above-mentioned mixing liquid is stirred at room temperature 1min, processes through 0.22 μm micro-filtration membrane, make
With LC-ESI-MS/MS to adding and thing carries out Structural Identification.
Described LC type is HP 1100, and testing conditions is:
Chromatographic column: ZIC-HILIC chromatographic column 2.1 × 150mm, 3.5 μm
Column temperature: 25 DEG C
Flowing phase: A: ammonium acetate solution (6.5mM)/acetonitrile (10:90, pH 5.5)；B: ammonium acetate
Aqueous solution (6.5mM)/acetonitrile (40:60, pH 5.5)；Gradient elution
Flow velocity: 0.1mL/min
Sample size: 10 μ L；
Described ESI-MS/MS type is HP 1100, and testing conditions is:
Ion source: ESI+
Dry gas temperature: 200 DEG C
Atomization air pressure: 50psi
Two grades of fragmentation voltage: 1.00V
Sweep limits: m/z 50-750
Described quinones substance of stablizing captures specifically comprising the following steps that of CML ability examination
(1) with 0.2M phosphate buffer (pH 4.5) preparation quinonoid solution so that it is concentration is 0.08mM；
(2) with the solution that phosphate buffered saline CML is 1-10mM of 0.2M；
(3) above-mentioned (1) and (2) solution is after Stopped-flow mixing chamber equal-volume mixes, and pH is
5.0,7.0 or 8.0；
(4) Stopped-flow is used, by reaction system during monitoring 25 DEG C in ultraviolet-visible light district
Absorbance change (200-750nm), measures the kinetics of 4MBQ Yu CML.
Described easy polymerization quinones substance add with CML and product identify concretely comprise the following steps:
(1) with the phosphate buffer (pH 8.0) of 0.2M prepare lysine (Lys) be 0.1M,
Glucose (Glu) is that the solution of 0.1M carrys out simulated foods system；
(2) in (1) described simulated foods system, add 2～3% tie containing catechol or pyrogallol
The quinone that the polyphenol oxidase of structure is formed；
(3) by sample in 80 DEG C or 100 DEG C of heating in water bath 1h；
(4) take sample after 1mL heating, add distilled water and be settled to 5mL；
(5) take 1mL diluent to process through 0.22 μm micro-filtration membrane, use UPLC-ESI-MS/MS to adding
Structural Identification is carried out with thing.
Described UPLC uses Agilent SB1290 type, and testing conditions is:
Chromatographic column: Agilent SB-C18Chromatographic column 2.1 × 50mm, 1.8 μm
Column temperature: 25 DEG C
Flowing phase: A) formic acid: water=1:1000 (v:v), B) acetonitrile
Gradient elution program: 0min (85%A)-4min (15%A)-8min (15%A)-10min (85%
A)；
Flow velocity: 0.2mL/min
Sample size: 5 μ L；
Mass spectrum uses type to be maxis Impact, and testing conditions is:
Ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Dry gas temperature: 180 DEG C
Nebulizer pressure: 0.3bar
Mass-to-charge ratio sweep limits: m/z50-1000
The present invention is to form adjacent benzene diquinone by catechol oxidation, and then adjacent benzene diquinone can directly and CML
The purpose that in reacting thus reaching system, existing CML eliminates.The present invention uses LC-ESI-MS/MS to identify
Quinones adds and product with CML's.As a result, it was confirmed that containing catechol or the polyphenol of pyrogallol structure
The quinones substance that oxidation is formed has capture effect to the CML in simulated foods system.
Compared with prior art, there is advantages that
(1) polyphenol containing catechol or pyrogallol structure is the material of a class Nantural non-toxic side effect,
Wherein, epicatechin, L-Epicatechin gallate, epigallocatechin gallate (EGCG) and table roasting youngster
Theine is the additive tea polyphenols allowing in National Standard of the People's Republic of China GB2760-2014 to use
Main component；Caffeic acid, as one of Semen Vitis viniferae extract main component, is regarded as It is generally accepted by FDA
Security classes additive (GRAS)；Rutin and Quercetin are as Citrus reticulata Blanco extract main component, and 4-methyl is adjacent
Benzodiazepines, as the main component of castoreum extract, is regarded as the security classes that It is generally accepted equally by FDA
Additive (GRAS)；The AGEs that system has been generated by the quinones substance that above-mentioned substance oxidation is formed has
Good elimination effect, compensate for AGEs inhibitor and system has existed AGEs adiaphorous defect.
(2) quinones substance of the present invention is the disappearing of AGEs in neutral or alkaline food system to pH
Removing solid capacity is higher.
(3) quinones substance of the present invention adds (see embodiment 1) after food system generates CML
Or interpolation (see embodiment 2-4) all can effectively reduce system CML level when not generating CML.
Accompanying drawing explanation
Fig. 1 is the possible path figure that inhibitor suppression CML is formed.
Fig. 2 is the pathway figure that quinones substance reacts with CML.
Fig. 3 is 4-methyl neighbour's benzene diquinone (4MBQ) and CML adds and a of thing) first mass spectrometric figure, b) two
Level mass spectrum and may structure and fracture mode.
Fig. 4 is EC quinones to be added and a of thing (80 DEG C of heating 1h) with CML) first mass spectrometric figure, b) two
Level mass spectrum.
Fig. 5 is to add the possible molecular structural formula with thing and fracture mode described in Fig. 4.
Fig. 6 is EC quinones to be added and a of thing (100 DEG C of heating 1h) with CML) first mass spectrometric figure, b)
Second order ms figure and may structure and fracture mode.
Fig. 7 is that EGCG quinones adds with CML and a of thing (100 DEG C of heating 1h)) first mass spectrometric figure,
B) second order ms figure.
Fig. 8 is to add the possible molecular structural formula with thing and fracture mode described in Fig. 7.
Detailed description of the invention
Elaborate below in conjunction with specific embodiment.
Embodiment 1
4-methyl neighbour's benzene diquinone (4MBQ) capture CML ability is identified and is added and identifies with product structure,
Specifically include following steps:
(1) 0.2M phosphate buffer (pH 4.5) preparation 4MBQ solution is used so that it is concentration is
0.08mM；
(2) with the solution that phosphate buffered saline CML is 1-10mM of 0.2M, make with above-mentioned
(1), after the mixing of solution equal-volume, pH is 5.0,7.0 or 8.0；
(3) Stopped-flow is used, by reaction system during monitoring 25 DEG C in ultraviolet-visible light district
(200-750nm) absorbance change, measures the kinetics of 4MBQ Yu CML；
(4) preparing CML with the phosphate buffer (pH 7.0) of 0.2M is that 10mM, 4MBQ are
The solution of 1mM；
(5) described to (4) mixing liquid is stirred at room temperature 1min, at 0.22 μm micro-filtration membrane
Reason, prepares liquid to be measured；
LC-ESI-MS/MS is finally used to use following testing conditions that prepared testing sample is detected.
Described LC type is HP 1100, and testing conditions is:
Chromatographic column: ZIC-HILIC chromatographic column 2.1 × 150mm, 3.5 μm
Column temperature: 25 DEG C
Flowing phase: A: ammonium acetate solution (6.5mM)/acetonitrile (10:90, pH 5.5)；B: ammonium acetate
Aqueous solution (6.5mM)/acetonitrile (40:60, pH 5.5)；Gradient elution
Flow velocity: 0.1mL/min
Sample size: 10 μ L；
Described ESI-MS/MS type is HP 1100, and testing conditions is:
Ion source: ESI+
Dry gas temperature: 200 DEG C
Atomization air pressure: 50psi
Two grades of fragmentation voltage: 1.00V
Sweep limits: m/z 50-750.
Above-mentioned Stopped-flow is used to obtain, the 4MBQ apparent kinetics constant to CML capture effect
(kobs) and second-order kinetics constant (k2) as shown in table 1, show that 4MBQ is to body when pH >=7
In system, the capture ability of CML is strong.When CML be 5mM, 4MBQ be 1mM time, pH 8.0,25
4MBQ in 4MBQ can capture system in 5 minutes at DEG C～at CML, pH7.0,25 DEG C of 36%
In system can being captured in 5 minutes～the CML of 14%.
1:25 DEG C of table, pH 5,7,8 times, the apparent kinetics constant (k that 4MBQ with CML reactsobs)、
Second-order kinetics constant (k2)
Use above-mentioned LC-ESI-MS/MS, use above-mentioned testing conditions that above-mentioned liquid to be measured is detected,
Obtain capturing first mass spectrometric (Fig. 3 a) and second order ms figure (Fig. 3 b) of product, thus can release reaction and produce
The structure chart of thing and possible fracture mode, as shown in Figure 3 b.
Embodiment 2
Epicatechin (EC) quinones capture CML is added the Structural Identification with product, specifically includes following step
Rapid:
(1) with the phosphate buffer (pH 8.0) of 0.2M prepare respectively lysine (Lys) be 0.1M,
Glucose (Glu) is that the solution of 0.1M carrys out simulated foods system；
(2) take the simulated foods system described in 1mL (1), add the EC quinone of 2mM；
(3) by sample in 80 DEG C of heating in water bath 1h；
(4) take sample after 1mL heating, add distilled water and be settled to 5mL；
(5) take 1mL diluent to process through 0.22 μm micro-filtration membrane, use UPLC-ESI-MS/MS pair
Add and carry out Structural Identification with thing.
Described UPLC uses Agilent SB1290 type, and testing conditions is:
Chromatographic column: Agilent SB-C18Chromatographic column 2.1 × 50mm, 1.8 μm
Column temperature: 25 DEG C
Flowing phase: A) formic acid: water=1:1000 (v:v), B) acetonitrile
Gradient elution program: 0min (85%A)-4min (15%A)-8min (15%A)-10min (85%
A)；
Flow velocity: 0.2mL/min
Sample size: 5 μ L；
Mass spectrum uses type to be maxis Impact, and testing conditions is:
Ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Dry gas temperature: 180 DEG C
Nebulizer pressure: 0.3bar
Mass-to-charge ratio sweep limits: m/z 50-1000
Use above-mentioned UPLC-ESI-MS/MS, use above-mentioned testing conditions that above-mentioned sample is detected,
Add to EC quinones and CML and the first mass spectrometric (Fig. 4 a) of thing and second order ms figure (Fig. 4 b), can push away
Go out the structure chart of product and possible fracture mode, as shown in Figure 5.EC quinones and CML are described
Reaction forms new material, thus eliminates CML.
Embodiment 3
Epicatechin (EC) quinones capture CML is added the Structural Identification with product, specifically includes following step
Rapid:
(1) with the phosphate buffer (pH 8.0) of 0.2M prepare respectively lysine (Lys) be 0.1M,
Glucose (Glu) is that the solution of 0.1M carrys out simulated foods system；
(2) take the simulated foods system described in 1mL (1), add the EC quinone of 2mM；
(3) by sample in 100 DEG C of heating in water bath 1h；
(4) take sample after 1mL heating, add distilled water and be settled to 5mL；
(5) take 1mL diluent to process through 0.22 μm micro-filtration membrane, use UPLC-ESI-MS/MS pair
Add and carry out Structural Identification with thing.
Described UPLC uses Agilent SB1290 type, and testing conditions is:
Chromatographic column: Agilent SB-C18Chromatographic column 2.1 × 50mm, 1.8 μm
Column temperature: 25 DEG C
Flowing phase: A) formic acid: water=1:1000 (v:v), B) acetonitrile
Gradient elution program: 0min (85%A)-4min (15%A)-8min (15%A)-10min (85%
A)；
Flow velocity: 0.2mL/min
Sample size: 5 μ L；
Mass spectrum uses type to be maxis Impact, and testing conditions is:
Ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Dry gas temperature: 180 DEG C
Nebulizer pressure: 0.3bar
Mass-to-charge ratio sweep limits: m/z 50-1000
Use above-mentioned UPLC-ESI-MS/MS, use above-mentioned testing conditions that above-mentioned sample is detected,
Add to EC quinones and CML and the first mass spectrometric (Fig. 6 a) of thing and second order ms figure (Fig. 6 b), thus
The structure chart of product and possible fracture mode can be released, as shown in Figure 6 b.
Embodiment 4
Epigallocatechin gallate (EGCG) (EGCG) quinones capture CML is added the structure mirror with product
Fixed, specifically include following steps:
(1) with the phosphate buffer (pH 8.0) of 0.2M prepare lysine (Lys) be 0.1M,
Glucose (Glu) is that the solution of 0.1M carrys out simulated foods system；
(2) take the simulated foods system described in 1mL (1), add the EGCG quinone of 3mM；
(3) by sample in 80 DEG C of heating in water bath 1h；
(4) take sample after 1mL heating, add distilled water and be settled to 5mL；
(5) take 1mL diluent to process through 0.22 μm micro-filtration membrane, use UPLC-ESI-MS/MS pair
Add and carry out Structural Identification with thing.
Described UPLC uses Agilent SB1290 type, and testing conditions is:
Chromatographic column: Agilent SB-C18Chromatographic column 2.1 × 50mm, 1.8 μm
Column temperature: 25 DEG C
Flowing phase: A) formic acid: water=1:1000 (v:v), B) acetonitrile
Gradient elution program: 0min (85%A)-4min (15%A)-8min (15%A)-10min (85%
A)；
Flow velocity: 0.2mL/min
Sample size: 5 μ L；
Mass spectrum uses type to be maxis Impact, and testing conditions is:
Ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Dry gas temperature: 180 DEG C
Nebulizer pressure: 0.3bar
Mass-to-charge ratio sweep limits: m/z 50-1000.
Use above-mentioned UPLC-ESI-MS/MS, use above-mentioned testing conditions that above-mentioned sample is detected,
Obtain EGCG quinones and CML to add and the first mass spectrometric (Fig. 7 a) of thing and second order ms figure (Fig. 7 b),
Thus can release the structure chart of product and possible fracture mode, as shown in Figure 8.
Claims (9)
1. carboxymethyl lysine remover, it is characterised in that described remover is containing catechol
Or the quinones substance that the polyphenol oxidase of pyrogallol construction unit is formed.
Remover the most according to claim 1, it is characterised in that described polyphenol includes that 4-methyl is adjacent
Benzodiazepines, epicatechin, L-Epicatechin gallate, caffeic acid, Quercetin, epigallo catechin
Epicatechol gallate, table GC, luteolin, rutin.
3. remover described in claim 1 or 2 is in terms of reducing food system carboxymethyl-lysine content
Application.
Application the most according to claim 3, it is characterised in that disappear described in adding in food system
Except agent, control pH >=7 of system.
Application the most according to claim 3, it is characterised in that the pH of described system is 8.
Application the most according to claim 3, it is characterised in that the reaction temperature of described system is
25-100℃。
7. according to the application described in claim 3 or 4 or 5 or 6, it is characterised in that described remover
The 2-3% that addition is system lysine content.
Application the most according to claim 7, it is characterised in that described remover is at food system not
Add after generating or generated CML.
9. according to the application described in claim 3 or 4 or 5 or 6, it is characterised in that described food body
System includes milk product, grain and goods thereof, flavoring agent, meat and goods thereof, tin product.
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| CN111000154A (en) * | 2019-12-30 | 2020-04-14 | 南京黄教授食品科技有限公司 | Method for reducing advanced glycosylation end products of roasted chicken during frying |
| CN113925168A (en) * | 2021-10-28 | 2022-01-14 | 湖北工业大学 | Application of EGCG quinone as inhibitor for resisting AGEs (angiotensin-converting enzyme) release in gastrointestinal tract |
| CN114903070A (en) * | 2022-05-23 | 2022-08-16 | 湖北工业大学 | Low AGEs waffles with high sensory quality and preparation method thereof |
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| CN111000154A (en) * | 2019-12-30 | 2020-04-14 | 南京黄教授食品科技有限公司 | Method for reducing advanced glycosylation end products of roasted chicken during frying |
| CN111000154B (en) * | 2019-12-30 | 2022-06-17 | 南京黄教授食品科技有限公司 | Method for reducing advanced glycosylation end products of roasted chicken during frying |
| WO2022247095A1 (en) * | 2021-05-25 | 2022-12-01 | 浙江大学 | Hydrophilic interaction chromatography-reversed phase liquid chromatography coupled analysis method for proanthocyanidin structure |
| CN113925168A (en) * | 2021-10-28 | 2022-01-14 | 湖北工业大学 | Application of EGCG quinone as inhibitor for resisting AGEs (angiotensin-converting enzyme) release in gastrointestinal tract |
| CN114903070A (en) * | 2022-05-23 | 2022-08-16 | 湖北工业大学 | Low AGEs waffles with high sensory quality and preparation method thereof |
| CN114916572A (en) * | 2022-05-23 | 2022-08-19 | 湖北工业大学 | Low-AGEs EGCG quinone-cookie and preparation method thereof |
| CN114916571A (en) * | 2022-05-23 | 2022-08-19 | 湖北工业大学 | Application of EC quinone in improving toughness biscuit quality |
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Effective date of registration: 20200819 Address after: About 100 meters to the right of Houhu village committee, Jinghai Town, Huilai County, Jieyang City, Guangdong Province Patentee after: Guangdong Zhongxu Agriculture Co., Ltd Address before: 510640 Tianhe District, Guangdong, No. five road, No. 381, Co-patentee before: GUANGDONG CHONGQING FONT BIOCHEMICAL SCIENCE & TECHNOLOGY Co.,Ltd. Patentee before: SOUTH CHINA University OF TECHNOLOGY |