CN113666899B - Calcium complex of flavonoid compound and preparation method and application thereof - Google Patents
Calcium complex of flavonoid compound and preparation method and application thereof Download PDFInfo
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- CN113666899B CN113666899B CN202010408124.9A CN202010408124A CN113666899B CN 113666899 B CN113666899 B CN 113666899B CN 202010408124 A CN202010408124 A CN 202010408124A CN 113666899 B CN113666899 B CN 113666899B
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- kaempferol
- calcium
- complex
- solution
- calcium complex
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- 239000011575 calcium Substances 0.000 title claims abstract description 87
- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 51
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229930003935 flavonoid Natural products 0.000 title abstract description 25
- 235000017173 flavonoids Nutrition 0.000 title abstract description 25
- -1 flavonoid compound Chemical class 0.000 title abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 6
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 claims abstract description 138
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims abstract description 70
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 claims abstract description 69
- 235000008777 kaempferol Nutrition 0.000 claims abstract description 69
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims abstract description 69
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910001424 calcium ion Inorganic materials 0.000 claims abstract description 35
- 239000000126 substance Substances 0.000 claims abstract description 16
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 13
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 13
- 235000006708 antioxidants Nutrition 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 230000002000 scavenging effect Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 2
- 230000007760 free radical scavenging Effects 0.000 abstract description 7
- 230000033116 oxidation-reduction process Effects 0.000 abstract description 7
- 238000011160 research Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 11
- 150000002215 flavonoids Chemical class 0.000 description 10
- 235000008576 Mitragyna parvifolia Nutrition 0.000 description 9
- 240000004093 Mitragyna parvifolia Species 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 description 6
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 description 6
- 229940117893 apigenin Drugs 0.000 description 6
- 235000008714 apigenin Nutrition 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 5
- 239000001639 calcium acetate Substances 0.000 description 5
- 229960005147 calcium acetate Drugs 0.000 description 5
- 235000011092 calcium acetate Nutrition 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 4
- 239000011648 beta-carotene Substances 0.000 description 4
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 4
- 235000013734 beta-carotene Nutrition 0.000 description 4
- 229960002747 betacarotene Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 230000002292 Radical scavenging effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 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 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001669 calcium Chemical class 0.000 description 2
- 235000021466 carotenoid Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- VCCRNZQBSJXYJD-UHFFFAOYSA-N galangin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=CC=C1 VCCRNZQBSJXYJD-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NHLRLBJZRLVLJH-UHFFFAOYSA-N 3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1.C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 NHLRLBJZRLVLJH-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 1
- 240000006108 Allium ampeloprasum Species 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910014472 Ca—O Inorganic materials 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- GQODBWLKUWYOFX-UHFFFAOYSA-N Isorhamnetin Natural products C1=C(O)C(C)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 GQODBWLKUWYOFX-UHFFFAOYSA-N 0.000 description 1
- 229930194248 Licoflavone Natural products 0.000 description 1
- MEHHCBRCXIDGKZ-UHFFFAOYSA-N Licoflavone C Natural products CC(C)=CCC1=C(O)C=C(O)C(C(C=2)=O)=C1OC=2C1=CC=C(O)C=C1 MEHHCBRCXIDGKZ-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 1
- 241000241413 Propolis Species 0.000 description 1
- 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 1
- CVBNMWXECPZOLM-UHFFFAOYSA-N Rhamnetin Natural products COc1cc(O)c2C(=O)C(=C(Oc2c1)c3ccc(O)c(O)c3O)O CVBNMWXECPZOLM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241001174051 Thesium arvense Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 238000013211 curve analysis Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 230000008030 elimination Effects 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
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- 235000019261 food antioxidant Nutrition 0.000 description 1
- CIPSYTVGZURWPT-UHFFFAOYSA-N galangin Natural products OC1=C(Oc2cc(O)c(O)cc2C1=O)c3ccccc3 CIPSYTVGZURWPT-UHFFFAOYSA-N 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- JBQATDIMBVLPRB-UHFFFAOYSA-N isoliquiritigenin Natural products OC1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 JBQATDIMBVLPRB-UHFFFAOYSA-N 0.000 description 1
- DXDRHHKMWQZJHT-FPYGCLRLSA-N isoliquiritigenin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)C1=CC=C(O)C=C1O DXDRHHKMWQZJHT-FPYGCLRLSA-N 0.000 description 1
- 235000008718 isoliquiritigenin Nutrition 0.000 description 1
- 235000008800 isorhamnetin Nutrition 0.000 description 1
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N isorhamnetin Chemical compound C1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 IZQSVPBOUDKVDZ-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 description 1
- 235000007743 myricetin Nutrition 0.000 description 1
- 229940116852 myricetin Drugs 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- SUYJZKRQHBQNCA-UHFFFAOYSA-N pinobanksin Natural products O1C2=CC(O)=CC(O)=C2C(=O)C(O)C1C1=CC=CC=C1 SUYJZKRQHBQNCA-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012019 product validation Methods 0.000 description 1
- 229940069949 propolis Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- JGUZGNYPMHHYRK-UHFFFAOYSA-N rhamnetin Chemical compound C=1C(OC)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 JGUZGNYPMHHYRK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
- A23L33/165—Complexes or chelates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
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Abstract
The invention relates to an antioxidant, and particularly discloses a calcium complex of a flavonoid compound, a preparation method and application thereof, wherein the structural general formula of the flavonoid compound is shown as formula I. The kaempferol in the flavonoid compound is exemplified by kaempferol solution and calcium ion solution, and the kaempferol-calcium complex is obtained by mixing and reacting the kaempferol solution and the calcium ion solution, and the chemical structural formula of the kaempferol-calcium complex is shown as formula II. Experimental research shows that the kaempferol-calcium complex has higher free radical scavenging activity and lower oxidation-reduction potential compared with kaempferol, and can be used as antioxidant, for example, in products with antioxidant requirements, such as food, medicine, cosmetics, skin care products, etc.
Description
Technical Field
The present invention relates to antioxidants, and in particular to calcium complexes of flavonoids.
Background
Kaempferol (Kaempferol, kaem), also known as thesium iii, is one of flavonoids, chemical name 3,5,7,4'-tetrahydroxyflavone (3, 5,7,4' -tetrahydroxyflavone), relative to molecular weight 286.23, the pure monomer is yellow crystalline powder. Are widely found in a variety of vegetables and fruits, such as leeks, tomatoes, broccoli, grapefruits, strawberries. Pure products have been extracted from tea, propolis, wu Zhenzi and other green plants. Some researches report that kaempferol has free radical scavenging activity, is a good natural antioxidant, and has various biological activities of anti-inflammatory, anticancer, antibacterial, diabetes treatment and the like.
If the performance of kaempferol can be studied deeply, even if an antioxidant with higher oxidation resistance is developed by using the kaempferol, the application range of kaempferol can be widened, and the effect and advantages of the kaempferol can be exerted to a greater extent.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a calcium complex of flavonoid compounds, and a preparation method and application thereof.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
in a first aspect, the present invention provides a calcium complex of a flavonoid compound, characterized in that the flavonoid compound has the following structural formula:
wherein R is 1 ，R 2 ，R 3 ，R 4 ，R 1 ′，R 2 ′，R 3 ′，R 4 ′，R 5 ' is selected from one of hydrogen, hydroxyl, C1-5 alkyl, C3-5 alkenyl and C1-5 alkoxy or isomer thereof respectively;
at the same time, R 1 ，R 2 ，R 3 ，R 4 ，R 1 ′，R 2 ′，R 3 ′，R 4 ′，R 5 At least one of the's' needs to be hydroxyl.
The flavonoid compounds described herein include naturally occurring flavonoid compounds and derivatives thereof that have been chemically modified.
The invention takes kaempferol as a representative, and experiments prove that the kaempferol can be matched with calcium ions to form a kaempferol-calcium complex shown in a formula II. Further, it was found from a plurality of experiments that flavonoids having the same 3-and 4-positions structure as kaempferol (shown in FIG. 3) are obtained by the above-mentioned general structure, i.e., flavonoids having calcium ions at the 3-and 4-positions are complexed with each other, thereby obtaining the corresponding flavonoidsCalcium complex of the compound. And the 3, 4-position of the flavonoid compound having the above general structure has higher complexing activity with metal ions according to common knowledge in the art, thus R 1 ，R 2 ，R 3 ，R 4 ，R 1 ′，R 2 ′，R 3 ′，R 4 ′，R 5 The selection of the substituents limited by the above range does not affect the coordination of the flavonoid compound with Ca (II) at the 3-and 4-positions. In order to increase the scavenging activity of free radicals after complexing Ca (II), R 1 ，R 2 ，R 3 ，R 4 ，R 1 ′，R 2 ′，R 3 ′，R 4 ′，R 5 The' at least one substituent is selected to be a hydroxyl group so that the free radical scavenging activity of the hydroxyl group at other positions is promoted after the flavonoid compound is complexed with Ca (II).
The flavonoid compounds may be, for example, licoflavone, isoliquiritigenin, galangin, inulins, fepristone, quercetin, rhamnetin, isorhamnetin, and myricetin and derivatives thereof as shown in fig. 6, but are not limited thereto.
In a second aspect, the invention provides a kaempferol-calcium complex, wherein the chemical structural formula of the kaempferol-calcium complex is shown as formula II, and M is Ca.
The kaempferol-calcium complex provided by the invention has a wave number of 1650cm in an infrared spectrum -1 、1615cm -1 、1365cm -1 、1223cm -1 And 582cm -1 There is a characteristic absorption peak in the vicinity.
In a third aspect, the invention provides a preparation method of the kaempferol-calcium complex, which comprises the steps of mixing a kaempferol solution with a calcium ion solution to obtain a reaction product, and obtaining the kaempferol-calcium complex.
And (3) evaporating the obtained reaction product under reduced pressure, washing with a mixed solvent of 1:1 methanol and water, filtering and drying to obtain a finished product of the kaempferol-calcium complex.
Preferably, the solute of the calcium ion solution is weak acid calcium salt.
It has been found that when a calcium salt of a strong acid is used as a solute, the strong acid generated by the product needs to be neutralized to promote the formation of a complex, i.e., after the kaempferol solution is mixed with the calcium ion solution, an alkaline substance is added to neutralize the acid generated after the mixing, and the pH of the mixed solution is adjusted to be neutral.
Further preferably, the molar ratio of kaempferol to calcium ions is 1:19-19:1, namely under the molar ratio, the kaempferol-calcium complex can be prepared; in order to better promote the formation of the kaempferol-calcium complex, a relatively excessive amount of calcium ions may be employed to shorten the time for obtaining the kaempferol-calcium complex, and thus the above molar ratio is more preferably not more than 2:1.
Optionally, ethanol is used as a solvent of the kaempferol and calcium ion solution; solubilization can also be carried out with dimethyl sulfoxide under high concentration conditions. After dimethyl sulfoxide is solubilized in ethanol, kaempferol is less than or equal to 1mM, and calcium ions are less than or equal to 500 mu M.
Alternatively, the concentration of the kaempferol solution may be 100. Mu.M to 1mM, and the concentration of the calcium ion solution may be 50. Mu.M to 500. Mu.M. However, in practical applications, the concentration of the above solution is not limited to this, and for example, when milk is used as a calcium ion donor solution, the calcium ion concentration can be on the order of mM, and casein, whey protein and milk fat globules in milk can be combined with flavonoids to improve the solubility of the flavonoids in milk.
In a third aspect, the invention provides the use of the kaempferol-calcium complex as an antioxidant and scavenging free radicals.
The experiment proves that the kaempferol-calcium complex has lower oxidation-reduction potential and higher free radical scavenging activity compared with the kaempferol, and has the characteristics of naturalness, no toxicity and good physiological function, so that the kaempferol-calcium complex can be used as an antioxidant, for example, in products with antioxidant requirements, such as foods, medicines, cosmetics, skin care products and the like.
The application may be embodied in a method for improving the oxidation resistance of a calcium-containing substance, for example, for a milk product rich in calcium ions, kaempferol may be used as a food additive, and kaempferol is added thereto to react with calcium ions in the calcium-containing substance to generate a kaempferol-calcium complex having oxidation resistance, thereby performing oxidation protection on the calcium-containing substance. And as kaempferol widely exists in various vegetables and fruits, the kaempferol is green and harmless, and the safety is reliably ensured.
More specifically, when kaempferol is added to the calcium-containing material, the kaempferol is slightly soluble in water, and can be added in an emulsifying manner by using an emulsifying agent, thereby improving the solubility of the kaempferol.
The raw materials or the reagents involved in the invention are all common commercial products, and the related operations are all routine operations in the field unless specified.
The above-mentioned preferable conditions can be combined with each other to obtain a specific embodiment on the basis of common knowledge in the art.
The invention has the beneficial effects that:
the invention utilizes kaempferol and calcium ions to form a kaempferol-calcium complex, and adopts ultraviolet visible absorption spectrum, infrared spectrum, mass spectrum, electrochemistry, residence spectrum and nanosecond time resolution spectrum to determine the structure and free radical scavenging activity of the kaempferol-calcium complex generated by kaempferol and calcium. Utilizes the better super-delocalization and large pi bond conjugated system of kaempferol and the empty orbit of Ca (II) to promote the formation of the complex.
The invention further researches the antioxidation mechanism of the kaempferol and Ca (II) complex, and can provide a new thought for flavonoid compounds as food additives, antioxidants and candidate drugs.
Drawings
FIG. 1 is a mass spectrum of the kaempferol-calcium complex of the invention.
FIG. 2 shows the analysis result of the ultraviolet visible absorption spectrum component in experimental example 1 of the present invention; wherein, the left graph shows the change of the ultraviolet visible absorption spectrum after Ca (II) is added into kaempferol, the embedded graph shows the analysis result of equimolar continuous change (Job-plot) components, and the right graph shows the non-change of the ultraviolet visible absorption spectrum after Ca (II) is added into contrasted apigenin.
FIG. 3 shows chemical formulas of kaempferol and apigenin.
FIG. 4 shows the result of redox potential analysis in experimental example 1 of the present invention.
FIG. 5 shows the results of radical scavenging experiments in Experimental example 1 of the present invention.
FIG. 6 shows an example of flavonoids that can be complexed with Ca (II) at the 3 and 4 positions.
Detailed Description
Reagents used in embodiments of the invention include: kaempferol (Kaem,>98%) and apigenin (Api,>98%) from Shaanxi Huike plant Co., ltd; calcium acetate (C) 4 H 6 CaO 4 ，>99%) from Shanghai Taitan technologies Co., ltd; beta-carotene, ferrocene (98%), sodium perchlorate (NaClO) 4 ,>98%) was purchased from Sigma-Aldrich (st.louis, MO), wherein beta-carotene was recrystallized from n-hexane and acetone, and purity was 98% as determined by high performance liquid chromatography; DPPH (digital versatile disc) · (>97%, beijing) from Zhongsheng Ruitai technologies Co., ltd; HPLC grade methanol is purchased from Mreda Limited (Lake Forest, calif., USA), HPLC grade ethanol (99.9% or more) Fine chemical research works (Tianjin), chloroform @>99%, beijing chemical plant) through an alumina column.
The experimental apparatus used in the embodiments of the present invention includes: agilent ultraviolet visible spectrophotometer Cary 60; fourier infrared spectrophotometers (Bruker Tensor 27, karlsruhe, germany); mass spectrum Thermo ScientificTM Q ExactiveTM HF (Waltham, MA, USA); the Shanghai Chen Hua electrochemical workstation CHI 760D; dwell spectrum (RX 2000, applied Photophysics Ltd, surrey, united Kingdom); nd 3+ : YAG laser (Quanta-Ray PRO-230,Spectra Physics Lasers,Inc, mountain View, calif., USA).
Preferred embodiments of the present invention will be described in detail below with reference to examples. It is to be understood that the following examples are given for illustrative purposes only and are not intended to limit the scope of the present invention. Various modifications and alterations of this invention may be made by those skilled in the art without departing from the spirit and scope of this invention.
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
EXAMPLE 1 kaempferol-calcium Complex
1. Raw materials
Kaempferol (Kaem,>98%) from Shaanxi Huidae plant Co., ltd; calcium acetate (C) 4 H 6 CaO 4 ，>99%) from Shanghai Taitan technologies Co., ltd; HPLC grade ethanol (more than or equal to 99.9%) and chloroform (Tianjin) from fine chemical research works>99%, beijing chemical plant) through an alumina column.
2. Preparation method
(1) Preparing kaempferol solution:
dissolving kaempferol in ethanol, solubilizing with 2% dimethyl sulfoxide, and performing ultrasonic treatment to obtain kaempferol solution with concentration of 1 mM;
(2) Preparing a calcium ion solution:
dissolving calcium acetate in ethanol, solubilizing with 2% dimethyl sulfoxide, and performing ultrasonic treatment to obtain calcium ion solution with concentration of 500 μm;
(3) Mixing the kaempferol solution and the calcium ion solution according to the volume ratio of 2:1, and carrying out reduced pressure evaporation to dryness, washing, filtering and drying to obtain the product.
3. Product validation
(1) Mass spectrometry:
the obtained product was subjected to mass spectrometry (cation mode) and the results are shown in FIG. 1. Experimental values (exp.) and theoretical values (cal.) as shown in table 1.
Table 1 experimental (exp.) and theoretical (Cal.) values of the mass spectrum
| Exp.(m/z) | Cal.(m/z) | Complex compound |
| 652/653 | 651/652/653 | Ca(II)-(Kaem-H) 2 +Na + +H 2 O |
| 657/658/659 | 657/658/659 | Ca(II)-(Kaem-H) 2 +H + +C 2 H 5 OH |
Note that: complex Ca (II) - (Kaem-H) 2 Hereafter abbreviated as Ca (II) -Kaem 2 。
(2) Ultraviolet visible absorption spectrum and Job-plot equimolar continuous change curve analysis:
firstly, under different molar ratios of kaempferol and Ca (II), the absorption spectrum of the formed complex is that: the UV-visible absorption spectrum of the complex was measured using a mixture of 20. Mu.M Kaem and 2 to 320. Mu.M Ca (II) in ethanol, as shown in FIG. 2 (left panel).
In ethanol solution, the maximum absorption of kaempferol is 368nm, after Ca (II) is added, 425nm shoulder appears at the long wave, and no absorption peak appears in the long wave direction of Ca (II) alone, so that the Ca (II) is proved to be matched with kaempferol.
Next, an absorption spectrum was obtained by controlling the total concentration of Ca (II) to 50. Mu.M and changing the molar ratio of kaempferol to Ca (II) to 1:19 to 19:1. Calculating the proportion by adopting a Job's plot method, taking an absorption value at 440nm wavelength in an absorption spectrum as an ordinate, taking the mole fraction of metal ions as an abscissa, performing linear fitting to obtain a Job's plot curve, and obtaining the proportion of the reaction of kaempferol and Ca (II) through the abscissa at the intersection point.
Job-Plot results (inset in the left panel of FIG. 2) show a Ca (II) to kaempferol ratio of 1:2 production of Ca (II) -Kaem 2 The structure of the kaempferol-calcium complex is further verified by combining the mass spectrum results.
Further, as a comparison test, apigenin which is the same flavonoid substance is used for replacing kaempferol (the chemical structural formulas of the apigenin and the kaempferol are shown as figure 3, and the 4-position groups and the 5-position groups are the same), and the analysis result of ultraviolet-visible absorption spectrum shows that Ca (II) is not matched with apigenin, so that Ca (II) is not matched with kaempferol at the 4-position and the 5-position.
Thus, it can be demonstrated that the coordination site of kaempferol and calcium ions is at the 3,4 positions.
(3) And (3) infrared spectrum analysis:
and mixing the obtained product with KBr, tabletting, and carrying out infrared spectrum vibration absorption peak analysis, wherein the result is as follows:
the carbonyl vibration peak of pure kaempferol is 1657cm -1 After Ca (II) ions are added, the oxygen on the carbonyl group is matched with Ca (II), so that the electron cloud density of the carbonyl group is reduced, and the carbonyl group moves to a low wave number by 7cm -1 The method comprises the steps of carrying out a first treatment on the surface of the 582cm of low-frequency fingerprint area -1 Stretching vibration of Ca-O occurs.
The infrared spectrum major frequencies are listed in table 2:
TABLE 2 vibration absorption peak (cm) of infrared spectrum -1 )
| Compounds of formula (I) | ν(C＝O) | ν(C＝C) | ν(C-OH) | ν(C-O-C) | ν(M-O) |
| Kaempferol | 1657 | 1613 | 1372 | 1243 | - |
| Kaempferol-calcium complex | 1650 | 1615 | 1365 | 1223 | 582 |
From this, it can be seen that the kaempferol and calcium acetate react and then are matched at the carbonyl position, and the peak position is shifted backward after the matching.
In conclusion, the structure of the obtained product was proved to be Ca (II) -Kaem 2 Structure (shown in formula II).
It is further verified that flavonoids having the same 3-and 4-positions structure as kaempferol can be complexed with calcium ions to form the corresponding calcium complexes of flavonoids.
EXAMPLE 2 kaempferol-calcium Complex
This embodiment differs from embodiment 1 in that: calcium chloride is adopted to replace calcium acetate, and the pH value of the solution is adjusted to be neutral after the mixture is mixed with kaempferol.
The obtained product was confirmed to have the same structure as the products obtained in example 1 and example 2 by mass spectrometry and infrared spectral vibration absorption peak analysis.
Experimental example 1
This experimental example is used to illustrate the oxidation resistance of kaempferol-calcium complex.
1. Oxidation-reduction potential
In this experimental example, 100. Mu.M kaempferol solution (Kaem) and 1000. Mu.M calcium ion solution (Ca-Kaem) were added to the solution by cyclic voltammetry 2 ) The redox potential was measured.
The cyclic voltammetry is specifically as follows: the working electrode was a glassy carbon electrode and the reference electrode was a silver ion electrode (0.10. Mu.M NaClO 4 +0.10μM AgNO 3 ) The auxiliary electrode is a platinum electrode. 0.10 mu M NaClO 4 As electrolyte, 50. Mu.M ferrocene was used as an internal standard. The scanning range is-0.5V to +0.9V, and the scanning speed is 0.05V/s.
As a result, as shown in FIG. 4, the oxidation-reduction potential of kaempferol in the solvent was 0.166V, and after adding an excessive amount of Ca (II) solution, the oxidation-reduction potential was significantly reduced to-0.081V. The method shows that the oxidation-reduction potential can be obviously reduced and the oxidation resistance can be obviously improved by adding the calcium ion solution into the kaempferol solution.
2. Free radical scavenging activity
(1) Kaempferol and kaempferol-calcium complex pair DPPH · Radical scavenging ability assay: measurement of 100. Mu.M DPPH using Cary 60 · 、100μM DPPH · +50μM Kaem、100μM DPPH · Absorption spectra of +50. Mu.M Kaem+50. Mu.M Ca (II) at different times, and on the ordinate, the absorption value (absorpance) at 516nm, and on the abscissa, the time (t) were taken as the DPPH for each sample pair · And (3) analyzing the free radical scavenging activity and mechanism of the sample according to the scavenging kinetic curve, wherein the experimental solvent is ethanol.
(2) Determination of the beta-carotene cation radical scavenging Capacity of Kaempferol and Kaempferol-calcium Complex: a quartz cell with an optical path of 1cm was used, and the experimental solvents were ethanol, chloroform=7:3. Chloroform is used to promote the formation of cationic free radicals from beta-carotene. The antioxidant activity was analyzed using kinetic data at 940 nm. The absorbance of β -Car was 0.5, the concentration of Kaem was 50. Mu.M, and the concentration of Ca (II) was 500. Mu.M.
As shown in FIG. 5, 50. Mu.M kaempferol is respectively contained in,Removal of 100. Mu.M DPPH without 500. Mu.M calcium ion · (left panel, 516 nm) and 5. Mu.M beta. -carotene cationic radical beta. -Car ·+ (right panel, 940 nm) kinetics of the reaction (500. Mu.M calcium ion alone as control).
DPPH · Formula C 18 H 12 N 5 O 6 1, 1-diphenyl-2-trinitrophenylhydrazine (1, 1-diphenyl-2-picrylhydrazyl) is a dark purple crystal at normal temperature. DPPH (digital versatile disc) · Scavenging activity is often used as an indicator to evaluate the ability of an antioxidant to scavenge free radicals in a hydrogen transfer manner. The 516nm kinetics results in FIG. 4 show that Ca (II) is not compared with DPPH · Reacting Ca (II) -Kaem 2 DPPH removal · Is 181 times faster than Kaem precursor.
Carotenoid radical cations (Car ·+ ) Is the free radical of carotenoid oxidized product in electron transfer mode, and is photo-induced to generate Car ·+ The rapid clean-up dynamics of (c) may help to obtain antioxidant capacity information. Taking β -Car as an example:
β-Car→β-Car ·+ +e -
the kinetics at 940nm showed that neither Ca (II) ions nor Kaem alone were compatible with beta-Car ·+ After the Kaem is matched with Ca (II), the beta-Car is obviously accelerated ·+ The second-order reaction rate constant was (5.44.+ -. 0.02). Times.10 8 L·mol -1 ·s -1 。
Comparative example 1
Experiments show that certain divalent metal ions (such as zinc ions) can also form complexes with kaempferol, but the oxidation resistance of the obtained complexes is far lower than that of kaempferol-calcium complexes.
To demonstrate this, this comparative example uses zinc ions instead of calcium ions, zinc and kaempferol also complex at the 3,4 positions, but depending on the concentration of the ligand, 1 can be generated separately: 1 or 2:1 kaempferol-zinc complex. Oxidation-reduction potential of kaempferol-zinc complex and kaempferol-calcium complex and DPPH elimination · And beta-Car ·+ Second order reaction rate constant k of free radical Car·+ And k DPPH· (L·mol -1 ·s -1 ) The results of the comparison are shown in Table 3.
TABLE 3 comparison of antioxidant properties of Kaempferol-Zinc complexes and Kaempferol-calcium complexes
Note that: m is Zn or Ca.
From this, it can be seen that the kaempferol-calcium complex pair DPPH is superior to the kaempferol-zinc complex · And beta-Car ·+ The scavenging rate of the catalyst is obviously accelerated, and the scavenging effect on free radicals is more obvious.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (9)
1. The kaempferol-calcium complex is characterized in that the chemical structural formula of the kaempferol-calcium complex is shown as formula II, wherein M is Ca.
2. The method for preparing kaempferol-calcium complex as claimed in claim 1, wherein the kaempferol-calcium complex is obtained by mixing kaempferol solution with calcium ion solution to obtain reaction product.
3. The method of claim 2, wherein the solute of the calcium ion solution is a weak acid calcium salt;
or, the solute of the calcium ion solution is a strong acid calcium salt, and after the kaempferol solution and the calcium ion solution are mixed, the pH value of the mixed solution is adjusted to be neutral.
4. The method according to claim 2 or 3, wherein the molar ratio of kaempferol to calcium ions is 1:19-19:1.
5. The method of claim 4, wherein the molar ratio of kaempferol to calcium ions is no greater than 2:1.
6. The method according to claim 5, wherein the concentration of the kaempferol solution is 100. Mu.M to 1mM, and the concentration of the calcium ion solution is 50. Mu.M to 500. Mu.M.
7. Use of the kaempferol-calcium complex of claim 1 as an antioxidant.
8. Use of the kaempferol-calcium complex of claim 1 for scavenging free radicals.
9. A method for improving the oxidation resistance of a calcium-containing substance, characterized in that kaempferol is added to the calcium-containing substance to react with calcium ions in the calcium-containing substance to produce the kaempferol-calcium complex of claim 1 having oxidation resistance.
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