CN109331061B - Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof - Google Patents
Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof Download PDFInfo
- Publication number
- CN109331061B CN109331061B CN201811346769.3A CN201811346769A CN109331061B CN 109331061 B CN109331061 B CN 109331061B CN 201811346769 A CN201811346769 A CN 201811346769A CN 109331061 B CN109331061 B CN 109331061B
- Authority
- CN
- China
- Prior art keywords
- kurarinol
- ethanol
- application
- kuh
- seng
- 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.)
- Active
Links
- 102000003425 Tyrosinase Human genes 0.000 title claims abstract description 20
- 108060008724 Tyrosinase Proteins 0.000 title claims abstract description 20
- 229930003935 flavonoid Natural products 0.000 title claims abstract description 20
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 20
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 19
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 18
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000010828 elution Methods 0.000 claims abstract description 12
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 239000011347 resin Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 208000012641 Pigmentation disease Diseases 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000001179 sorption measurement Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 3
- 241000246044 Sophora flavescens Species 0.000 claims description 19
- 230000002087 whitening effect Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000000022 bacteriostatic agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 12
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 3
- 241000193985 Streptococcus agalactiae Species 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000004071 biological effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000469 ethanolic extract Substances 0.000 abstract 3
- 230000002265 prevention Effects 0.000 abstract 1
- XMUPAAIHKAIUSU-QRQCRPRQSA-N kurarinol Chemical compound C1([C@H]2OC=3C(C[C@@H](CCC(C)(C)O)C(C)=C)=C(O)C=C(C=3C(=O)C2)OC)=CC=C(O)C=C1O XMUPAAIHKAIUSU-QRQCRPRQSA-N 0.000 description 185
- KDADHLPROOOPIC-UHFFFAOYSA-N neokurarinol Natural products COc1cc(O)ccc1C1CC(=O)c2c(OC)cc(O)c(CC(CCC(C)(C)O)C(C)=C)c2O1 KDADHLPROOOPIC-UHFFFAOYSA-N 0.000 description 23
- -1 flavonoid compound Chemical class 0.000 description 18
- 229930003944 flavone Natural products 0.000 description 14
- 235000011949 flavones Nutrition 0.000 description 14
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 13
- 150000002212 flavone derivatives Chemical class 0.000 description 13
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 13
- LNIQZRIHAMVRJA-UHFFFAOYSA-N isoformononetin Chemical compound C=1C(OC)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 LNIQZRIHAMVRJA-UHFFFAOYSA-N 0.000 description 12
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 description 9
- 229930013930 alkaloid Natural products 0.000 description 9
- 150000003797 alkaloid derivatives Chemical class 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- YKGCBLWILMDSAV-SFHVURJKSA-N isoxanthohumol Chemical compound C1([C@H]2OC=3C(CC=C(C)C)=C(O)C=C(C=3C(=O)C2)OC)=CC=C(O)C=C1 YKGCBLWILMDSAV-SFHVURJKSA-N 0.000 description 9
- 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 8
- 239000000839 emulsion Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- LTTQKYMNTNISSZ-MWTRTKDXSA-N (2S)-(-)-kurarinone Chemical compound C1([C@H]2OC=3C(C[C@@H](CC=C(C)C)C(C)=C)=C(O)C=C(C=3C(=O)C2)OC)=CC=C(O)C=C1O LTTQKYMNTNISSZ-MWTRTKDXSA-N 0.000 description 6
- OKQQXHUICMLKQI-UHFFFAOYSA-N Citrusinol Chemical compound C=12C=CC(C)(C)OC2=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C=C1 OKQQXHUICMLKQI-UHFFFAOYSA-N 0.000 description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 6
- WUADCCWRTIWANL-UHFFFAOYSA-N biochanin A Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O WUADCCWRTIWANL-UHFFFAOYSA-N 0.000 description 6
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 6
- XQVFLLMCNGKXSM-UHFFFAOYSA-N kurarinone Natural products COc1cc(O)c(C(CC=C(C)C)C(=C)C)c2OC(CC(=O)c12)c3ccc(O)cc3O XQVFLLMCNGKXSM-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 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 description 6
- 235000009498 luteolin Nutrition 0.000 description 6
- KTAQQSUPNZAWEY-OSPHWJPCSA-N (2S)-2'-methoxykurarinone Chemical compound COC1=CC(O)=CC=C1[C@H]1OC2=C(C[C@@H](CC=C(C)C)C(C)=C)C(O)=CC(OC)=C2C(=O)C1 KTAQQSUPNZAWEY-OSPHWJPCSA-N 0.000 description 5
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 5
- XRYVAQQLDYTHCL-IQMFZBJNSA-N Sophoraflavanone G Natural products C1([C@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)C[C@@H](CC=C(C)C)C(C)=C)=CC=C(O)C=C1O XRYVAQQLDYTHCL-IQMFZBJNSA-N 0.000 description 5
- ISQRJFLLIDGZEP-CMWLGVBASA-N Sophoricoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)C=C1 ISQRJFLLIDGZEP-CMWLGVBASA-N 0.000 description 5
- ISQRJFLLIDGZEP-KJRRRBQDSA-N Sophoricoside Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1ccc(C=2C(=O)c3c(O)cc(O)cc3OC=2)cc1 ISQRJFLLIDGZEP-KJRRRBQDSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 description 5
- 235000007625 naringenin Nutrition 0.000 description 5
- 229940117954 naringenin Drugs 0.000 description 5
- XRYVAQQLDYTHCL-CMJOXMDJSA-N sophoraflavanone G Chemical compound C1([C@@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)C[C@@H](CC=C(C)C)C(C)=C)=CC=C(O)C=C1O XRYVAQQLDYTHCL-CMJOXMDJSA-N 0.000 description 5
- PIAPWPAWQGDOMN-SXAWMYDMSA-N (e)-1-[2,4-dihydroxy-6-methoxy-3-[(2r)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]phenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one Chemical compound COC1=CC(O)=C(C[C@@H](CC=C(C)C)C(C)=C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1O PIAPWPAWQGDOMN-SXAWMYDMSA-N 0.000 description 4
- TUUXBSASAQJECY-UHFFFAOYSA-N Anhydroicaritin Natural products C1=CC(OC)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1 TUUXBSASAQJECY-UHFFFAOYSA-N 0.000 description 4
- PIAPWPAWQGDOMN-UHFFFAOYSA-N Kuraridine Natural products COC1=CC(O)=C(CC(CC=C(C)C)C(C)=C)C(O)=C1C(=O)C=CC1=CC=C(O)C=C1O PIAPWPAWQGDOMN-UHFFFAOYSA-N 0.000 description 4
- DKEYBVYGENRHLN-UHFFFAOYSA-N Norkurarinone Natural products CC(=CCC(Cc1c(O)cc(C)c2C(=O)CC(Oc12)c3ccc(O)cc3O)C(=C)C)C DKEYBVYGENRHLN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 235000005875 quercetin Nutrition 0.000 description 4
- 229960001285 quercetin Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 3
- HKQYGTCOTHHOMP-UHFFFAOYSA-N Formononetol Natural products C1=CC(OC)=CC=C1C1=COC2=CC(O)=CC=C2C1=O HKQYGTCOTHHOMP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000219823 Medicago Species 0.000 description 3
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000007240 daidzein Nutrition 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229930003949 flavanone Natural products 0.000 description 3
- 150000002207 flavanone derivatives Chemical class 0.000 description 3
- 235000011981 flavanones Nutrition 0.000 description 3
- 235000012055 fruits and vegetables Nutrition 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229960004441 tyrosine Drugs 0.000 description 3
- JASGTHLRBAGTGY-PZJWPPBQSA-N (2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-(3-methylbut-3-enyl)-2,3-dihydrochromen-4-one Chemical compound C(CC(=C)C)C=1C(=CC(=C2C([C@@H]([C@H](OC=12)C1=C(C=C(C=C1)O)O)O)=O)OC)O JASGTHLRBAGTGY-PZJWPPBQSA-N 0.000 description 2
- FWTJDNRRDUBKEM-UHFFFAOYSA-N 2,3-dihydroxy-2-(4-methoxyphenyl)-3h-chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1(O)C(O)C(=O)C2=CC=CC=C2O1 FWTJDNRRDUBKEM-UHFFFAOYSA-N 0.000 description 2
- QXNWZXMBUKUYMD-ITUXNECMSA-N 4-keto-beta-carotene Chemical compound CC=1C(=O)CCC(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 QXNWZXMBUKUYMD-ITUXNECMSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YLZYAUCOYZKLMA-UHFFFAOYSA-N O-Methyl-maackiain Natural products O1C2=CC=3OCOC=3C=C2C2C1C1=CC=C(OC)C=C1OC2 YLZYAUCOYZKLMA-UHFFFAOYSA-N 0.000 description 2
- SLEPYIDGMPDTFO-UHFFFAOYSA-N Pterocarpin Natural products COc1ccc2C3Oc4c5OCOc5ccc4C3COc2c1 SLEPYIDGMPDTFO-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 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 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YLZYAUCOYZKLMA-SJCJKPOMSA-N pterocarpin Chemical compound O1C2=CC=3OCOC=3C=C2[C@H]2[C@@H]1C1=CC=C(OC)C=C1OC2 YLZYAUCOYZKLMA-SJCJKPOMSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LPEPZZAVFJPLNZ-SFHVURJKSA-N sophoraflavanone B Chemical compound C1([C@@H]2CC(=O)C=3C(O)=CC(O)=C(C=3O2)CC=C(C)C)=CC=C(O)C=C1 LPEPZZAVFJPLNZ-SFHVURJKSA-N 0.000 description 2
- YEDFEBOUHSBQBT-UHFFFAOYSA-N 2,3-dihydroflavon-3-ol Chemical class O1C2=CC=CC=C2C(=O)C(O)C1C1=CC=CC=C1 YEDFEBOUHSBQBT-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 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 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000006142 Luria-Bertani Agar Substances 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 229940124200 Melanin inhibitor Drugs 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000219784 Sophora Species 0.000 description 1
- 101710147108 Tyrosinase inhibitor Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- YXPMCBGFLULSGQ-YHEDCBSUSA-N echinenone Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(=O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CCCC2(C)C YXPMCBGFLULSGQ-YHEDCBSUSA-N 0.000 description 1
- 235000006932 echinenone Nutrition 0.000 description 1
- 230000000385 effect on melanoma Effects 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 229930003939 flavanonol Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229930186726 kushecarpin Natural products 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008099 melanin synthesis Effects 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 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 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YHWNASRGLKJRJJ-UHFFFAOYSA-N sophoraflavanone B Natural products C1C(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2OC1C1=CC=C(O)C=C1 YHWNASRGLKJRJJ-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K36/489—Sophora, e.g. necklacepod or mamani
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Dermatology (AREA)
- Mycology (AREA)
- Birds (AREA)
- Botany (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Communicable Diseases (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity and a preparation method thereof, wherein kuh-seng dregs are used as raw materials, waste materials are changed into things of value, ethanol is added for reflux extraction, filtration is carried out, filtrate is dried to obtain ethanol extract, after the ethanol extract is dissolved by methanol, the ethanol extract is loaded on AB-8 type macroporous adsorption resin, then gradient elution is carried out by ethanol with the concentration of 10%, 20%, 30%, 40%, 50%, 60%, 70% and 80%, and 50-70% of elution part is collected. The effective part prepared by the invention has obvious inhibitory activity on tyrosinase, has obvious antibacterial effect on staphylococcus aureus and streptococcus agalactiae, has good prevention and treatment effects on human body pigmentation diseases caused by excessive melanin, and has obvious and wide biological activity.
Description
Technical Field
The invention relates to a traditional Chinese medicine extract, in particular to a flavone effective part with tyrosinase inhibition and bacteriostasis functions in sophora flavescens decoction dregs, and belongs to the technical field of medicines.
Background
Radix Sophorae Flavescentis, a dry root of Sophoraflaviscens ait. of Leguminosae, is bitter in taste and cold in nature, and has effects of clearing heat, eliminating dampness, killing parasites, and promoting urination. The lightyellow sophora root is widely distributed and planted in most places in China; the main productions are Shanxi, Henan, Hebei, inner Mongolia and so on. Modern pharmacological studies show that alkaloid components in the radix sophorae flavescentis have biological activities of resisting tumors, hepatitis B viruses, inflammation, bacteria and insects and the like, and are widely applied to development of products such as pharmaceutical preparations, biological pesticides, veterinary drugs and the like. The market demand of the sophora flavescens as a common bulk Chinese medicinal material variety is increased year by year, and meanwhile, the quantity of solid wastes and byproducts generated in the preparation process is huge, and the solid wastes and the byproducts are discarded without an effective utilization way, so that the resource waste is caused, and the green and sustainable development of the sophora flavescens resource industry is not facilitated for a long time.
At present, alkaloid components in sophora flavescens are mostly used as raw materials in the related preparation industry of sophora flavescens, and water or acidic aqueous solution is mostly used as an extraction solvent when the alkaloid components are extracted. Because alkaloid components in the sophora flavescens are easy to dissolve in an acidic aqueous solution, while flavonoid components are poor in water solubility and are not easy to dissolve under an acidic condition, most of the alkaloid components are reserved in the herb residues after alkaloid extraction. Researches show that the flavonoids contained in radix sophorae flavescentis are mostly isovaleryl-substituted flavanone and flavanonol, and a small amount of flavonoids, isoflavones, pterocarpans and echinenone.
Tyrosinase is a key enzyme for melanin synthesis, and the expression and activity of tyrosinase are closely related to browning of fruits and vegetables and human body pigmentation diseases. Therefore, the tyrosinase inhibitor can be used as a melanin inhibitor to be applied to the fields of food, cosmetics, medicines and the like.
Disclosure of Invention
The purpose of the invention is: the radix sophorae flavescentis dregs after the alkaloid is extracted from the radix sophorae flavescentis are fully utilized, the effective parts of the total flavonoids in the radix sophorae flavescentis dregs are extracted through an optimal optimization process method, and experimental researches show that the effective parts of the total flavonoids in the radix sophorae flavescentis dregs prepared by the method have obvious tyrosinase inhibitory activity and bacteriostatic activity, and are high in total flavonoids content and few in impurities.
The technical scheme is as follows: the invention adopts the following technical scheme:
an effective component of radix Sophorae Flavescentis flavonoid with tyrosinase inhibitory activity and antibacterial activity is extracted from radix Sophorae Flavescentis residue, and the effective component comprises flavonoid compound with the following structure:
the preparation method of the kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, which is disclosed by the invention, comprises the following steps of:
(1) drying and crushing the sophora flavescens dregs, adding 40-80% ethanol according to the material-liquid ratio of 1g to 10-50 ml, carrying out reflux extraction for 1-2 times, each time for 2 hours, and concentrating the extracting solution under reduced pressure to obtain a dry substance;
(2) dissolving the dried substance obtained in the step (1) with 95% ethanol, and filtering;
(3) and (3) concentrating the filtrate obtained in the step (2) under reduced pressure to obtain a dry substance, adding a small amount of methanol, ultrasonically dissolving, slowly adsorbing on a macroporous adsorption resin column, sequentially eluting with ethanol with volume concentration of 10%, 20%, 30%, 40%, 50%, 60%, 70% and 80% which is 5-8 times of the volume of the column, and collecting the 50-70% ethanol elution part.
As a preferred embodiment, the preparation method of the flavonoid effective fraction having tyrosinase inhibitory activity and antibacterial activity described above is characterized by comprising the following steps:
and (3) the macroporous adsorption resin column in the step (3) is AB-8 type, and finally, an ethanol elution part with the volume concentration of 60% is collected.
A whitening emulsion comprising the flavonoid effective fraction of Sophora flavescens Aiton having tyrosinase inhibitory activity and antibacterial activity according to claim 1.
An agent for inhibiting browning of fruits and vegetables, which comprises the flavonoid effective fraction of Sophora flavescens having tyrosinase inhibitory activity and antibacterial activity according to claim 1.
A medicament for preventing and treating pigmentation in a human body caused by melanin abnormality, which comprises the effective fraction of the flavonoid represented by claim 1 having tyrosinase inhibitory activity and antibacterial activity.
The kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity is applied to preparing fruit and vegetable enzymatic browning inhibitors, whitening cosmetics and bacteriostats and preventing and treating human body pigmentation diseases or melanoma caused by melanin abnormality.
The above-mentioned application, the dosage form of the medicine or cosmetic includes solid powder, aqueous solution, alcoholic solution, emulsion, mask, cataplasm, injection, infusion solution, powder injection, granule, tablet, electuary, powder, oral liquid, sugar-coated agent, film-coated tablet, enteric-coated tablet, capsule, buccal agent, pill, paste, pellet, spray, drop pill, oral disintegrating agent or pellet.
The invention has the advantages that:
the method changes waste into valuable, and makes full use of the sophora flavescens dregs after the alkaloid is extracted from the sophora flavescens, and extracts the effective part with high content of total flavonoids in the sophora flavescens dregs by an optimal optimization process method. The extraction process of the invention is reasonable, the cost is low, and the invention can be used for industrial production.
Drawings
FIG. 1 is a UPLC-MS comparison of total ion current for different concentrations of ethanol elution sites;
in the figure, A: eluting with 10% ethanol; b: 20% ethanol elution fraction; c: eluting with 30% ethanol; d: eluting with 40% ethanol; e: eluting with 50% ethanol; f: eluting with 60% ethanol; g: eluting with 70% ethanol; h: 80% ethanol elution part.
Detailed Description
The substance and advantageous effects of the present invention will be described in further detail with reference to examples, which are provided only for illustrating the present invention and not for limiting the present invention. In addition, after reading the teaching of the present invention, those skilled in the art can make various changes or modifications to the invention, and these equivalents also fall within the scope of the claims appended to the present application.
EXAMPLE 1 preparation of effective fractions
Extracting 10 kg radix Sophorae Flavescentis residue (15 times volume of radix Sophorae Flavescentis residue obtained after extracting alkaloid by percolating with 1% acetic acid water solution) with 8 times of 80% ethanol under ultrasonic wave for 3 times, 1 hr each time, concentrating under reduced pressure to dry, dissolving the dried product with 95% ethanol, filtering, concentrating the filtrate under reduced pressure, drying, adding methanol for ultrasonic dissolution, loading onto macroporous resin AB-8 chromatographic column, eluting with 8 volumes of 10%, 20%, 30%, 40%, 50%, 60%, 70% and 80% ethanol in sequence, and collecting each eluted part.
The invention adopts the following method to measure the flavone content of the eluent with different volume concentrations of ethanol (10 percent to 80 percent).
Detection conditions of UPLC-TOF-MS/MS:
the instrument comprises the following steps: AB Sciex5600+ time-of-flight mass spectrometer, Shimadzu LC10A high performance liquid chromatograph
A chromatographic column: an ACQUITY UPLC BEH C18 column (100 mm. times.2.1 mm,1.7 μm),
mobile phase: 0.1% aqueous formic acid (a) -acetonitrile (B), gradient elution: 0 → 15min, 5% B → 50% B; 15 → 20min, 50% B → 80% B; 20 → 25min, 80% B → 80% B; the flow rate is 0.4mL/min, and the column temperature is 40 ℃; the amount of sample was 2. mu.L.
Mass spectrum conditions: a positive and negative ion mode; and (4) CUR: 35.000 psi; GS 1: 55.000 psi; GS 2: 55.000 psi; TEM: 550.000 deg.C; CE: 10.000V (negative ion mode); DP: 60.000V (negative ion mode); the scanning ranges m/z 100-.
The results are shown in FIG. 1: 10%, 20%, 30%, 40%, 50%, 60%, 70% and 80% of the ethanol eluates contain the following flavones:
the total flavone content of the 10% ethanol eluate was 12.5%. Mainly comprises the following components: 4-O- β -D-glucopyranoside, 3 '-hydroxy-kushenol O, 3',4 '-dihydroxy-isoflavone-7-O- β -D-glucopyranoside, 2, 3-dihydroxy-4' -methoxyflavanone 7-O- β -D-apiose- (1 → 6) - β -D-glucopyranoside;
the total flavone content of the 20% ethanol eluate was 18.4%. Mainly comprises the following components: cheilone-4-O- β -D-glucopyranoside, 3' -hydroxy-kushenol O, 3',4' -dihydroxy-isoflavone-7-O- β -D-glucopyranoside, 2, 3-dihydroxy-4 ' -methoxyflavanone 7-O- β -D-apiose- (1 → 6) - β -D-glucopyranoside, kuschecarin D, biochanin a, 7-methoxy-4 ' -hydroxyisoflavone, isoxanthohumol, homosophoricine;
the total flavone content of the 30% ethanol eluent is 16.3%. Mainly comprises the following components: mosoxanone-4-O-beta-D-glucopyranoside, 3 '-hydroxy-kushenol O, 3',4 '-dihydroxy-isoflavone-7-O-beta-D-glucopyranoside, 5,4' -dihydroxy-isoflavone-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, daidzein-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, 2-hydroxy-6- [2- (4-hydroxyphenyl) -2-carbonyl ] benzoic acid-3-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, kurarinol J, 7-hydroxy-4 '-methoxy-flavanone-3' -O- β -D-glucopyranoside, trifoliosid, 2, 3-dihydroxy-4 '-methoxy-flavanone-7-O- β -D-xylose- (1 → 6) - β -D-glucopyranoside, kurarinol O, biochanin a, kurarinol H, kurarinol K, 4' -hydroxy-isoflavone-7-O- β -D-apiose- (1 → 6) - β -D-glucopyranoside, garicin, kurarinol N, kurarinone, sophoricoside G;
the total flavone content of 40% ethanol eluate was 26.7%. Mainly comprises the following components: 3 '-hydroxy-kushenol O, 5,4' -dihydroxy-isoflavone-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, daidzein-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, kurarinol J, 7-hydroxy-4 '-methoxy-flavanone-3' -O-beta-D-glucopyranoside, pterocarpin, pseudoobtigenin-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, 2, 3-dihydroxy-4 '-methoxyflavanone-7-O-beta-D-xylose- (2, 3-dihydroxy-4' -methoxyflavanone-7-O-beta-D-xylopyranoside 1 → 6) - β -D-glucopyranoside, kurarinol O, 4' -methoxy-isoflavone-7-O- β -D-apiose- (1 → 6) - β -D-glucopyranoside, kushecarpin D, daidzein, biochanin a, kurarinol H, isodehydroicaritin, kurarinol W, kurarinol K, kurarinol P, kurarinol glycol, 7-methoxy-4 ' -hydroxyisoflavone, kurarinol G, naringenin, isoxanthohumol, kurarinol Q, homosophoricol, kurarinol N, kurarinone, kurarinol D, sophoricoside G, 2' -methoxykurarinone;
the total flavone content of the 50% ethanol eluate was 35.1%. Mainly comprises the following components: 7-hydroxy-4 '-methoxy-flavanone-3' -O-beta-D-glucopyranoside, pseudooblitigin-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, 2, 3-dihydroxy-4 '-methoxy-flavanone-7-O-beta-D-xylose- (1 → 6) -beta-D-glucopyranoside, kurarinol O, 4' -methoxy-isoflavone-7-O-beta-D-apiose- (1 → 6) -beta-D-glucopyranoside, pterocarpin, luteolin, daidzein, biochanin A, kurarinol H, isodehydroicaritin, kurarinol W, kurarinol K, kurarinol P, 4 '-hydroxy-isoflavone-7-O-beta-D-apiose- (1 → 6) -beta-D-glucopyranoside, (2R,3R) -8-isopentenyl-7, 2',4 '-trihydroxy-5-methoxyflavanonol, kurarinol, pseudobigenin, luteolin, 7-methoxy-4' -hydroxyisoflavone, kurarinol G, naringenin, isoxanthohumol, kurarinol Q, rikanone G, quercetin, homosophoricol, sophorafinol, 5-methoxy-7, 2',4' -trihydroxy-8-isopentenyl flavone, kurarinol V, kurarinol N, sophoflavone B, kurarinone, 5-methyl kurarinol C, kurarinol X, kurarinol S, anhydroicaritin, neokurarinol, kurarinol R, kurarinol C, kurarinol D, sophoricone flavanone G, (2S) -7,4 '-dihydroxy-5-methoxy-8- (gamma, gamma-dimethylallyl) -flavanone, citrusinol, 8-lavandiol, kuraridine, norkurarinone, 5, 7-dihydroxy-8-lavandione, kurarinol E, richardnone A, kurarinol M, kurarinol A, 2' -methoxykurarinone;
the total flavone content of the 60% ethanol eluate was 41.2%. Mainly comprises the following components: luteolin, daidzein, biochanin A, kurarinol H, isodehydroicaritin, kurarinol W, kurarinol K, kurarinol P, 4 '-hydroxy-isoflavone-7-O-beta-D-apiose- (1 → 6) -beta-D-glucopyranoside, (2R,3R) -8-isopentenyl-7, 2',4 '-trihydroxy-5-methoxydihydroflavonol, kurarinol, pseudobiotinin, luteolin, 7-methoxy-4' -hydroxyisoflavone, kurarinol G, naringenin, isoxanthohumol, kurarinol Q, richardinone G, quercetin, homosophoricilin, sophorafinol, 5-methoxy-7, 2',4' -trihydroxy-8-isopentenyl flavone, kurarinol V, kurarinol N, alfalfa lactone, 5, 7-dihydroxy-8 (R, R-dimethylallyl) pyrone, sophorflavone B, kurarinone, 5-methylkurarinol C, kurarinol X, kurarinol S, anhydroicaritin, kurarinol F, neokurarinol, kurarinol R, kurarinol C, kurarinol D, sophoraflavanone G, sophoraflavanone B, kurarinol L, kurarinol U, (2S) -7,4 '-dihydroxy 5-methoxy-8- (gamma, gamma-dimethylallyl) -flavanone, citrinol, 8-lavandiol, kuraridine, norkurarinone, 5, 7-dihydroxy-8-lavandula chromone, neonol E, richardnone A, kurarinol M, kurarinol A, 2' -methoxykurarinone, kurarinol B;
the total flavone content of the 70% ethanol eluate was 37.3%. Mainly comprises the following components: biochanin A, kurarinol H, kurarinol K, kurarinol P, 4 '-hydroxy-isoflavone-7-O-beta-D-apiose- (1 → 6) -beta-D-glucopyranoside, kurarinol, pseudobiotinin, luteolin, 7-methoxy-4' -hydroxyisoflavone, kurarinol G, naringenin, isoxanthohumol, kurarinol Q, richinone G, quercetin, sophoricol, 5-methoxy-7, 2',4' -trihydroxy-8-isopentenyl flavone, kurarinol V, kurarinol N, medicago lactone, 5, 7-dihydroxy-8 (r, r-dimethylallyl) pyrone, sophoaflavone B, kurarinone, 5-methylkurarinol C, kurarinol X, kurarinol S, anhydroicaritin, kurarinol F, neokurarinol, kurarinol R, kurarinol C, kurarinol D, sophoricoside G, sophoricoside B, kurarinol L, kurarinol U, (2S) -7,4 '-dihydroxy-5-methoxy-8- (γ, γ -dimethylallyl) -flavanone, citrusinol, 8-lavandiol, kuraridine, norkurarinone, 5, 7-dihydroxy-8-lavandinone, kurarinol E, richardnone a, kurarinol M, kurarinol a, 2' -methoxykurarinone, kurarinol B;
the total flavone content of 80% ethanol eluent is 32.5%. Mainly comprises the following components: kurarinol K, kurarinol P, kurarinol, pseudobiotagenin, luteolin, 7-methoxy-4 '-hydroxyisoflavone, naringenin, isoxanthohumol, kurarinol Q, quercetin, garbinin, sophorafinol, 5-methoxy-7, 2',4 '-trihydroxy-8-prenylflavone, kurarinol V, kurarinol N, medicago lactone, 5, 7-dihydroxy-8 (R, R-dimethylallyl) pyrone, sophorafenone B, kurarinone, 5-methylkurarinol C, kurarinol X, kurarinol S, anhydroicaritin, kurarinol F, neokurarinol, kurarinol R, kurarinol C, kurarinol D, sophoricoside G, sophorico flavanone B, kurarinol L, kurarinol U, (2S) -7,4' -dihydroxy-5-methoxy-8- (gamma), gamma-dimethylallyl) -flavanone, citrusinol, 8-lavender kaempferol, kuraridine, norkurarinone, 5, 7-dihydroxy-8-lavender chromone, kurarinol E, rikainone A, kurarinol M, kurarinol A, 2' -methoxykurarinone, and kurarinol B.
Comparing the detection results to obtain: the 60% ethanol elution fraction is particularly preferred because the active ingredient of flavone contained in the 60% ethanol elution fraction is rich and high in content, and contains few impurities.
Example 2 evaluation of tyrosinase inhibitory Activity of the effective fraction of Sophora flavescens residue extract
Dissolving the 10-80% ethanol eluate prepared in example 1 in methanol respectively to prepare 5mg/mL solution, and diluting to 2.500, 1.250, 0.625, 0.312, 0.156, and 0.078 mg/mL-1Six concentrations. Preparation of 5mg/mL-1The L-tyrosine solution of (2), 0.1mol/L phosphate buffer solution, 15mmol/L L-tyrosine solution, 0.25 mg/mL-1Tyrosinase, etc. Placing each group of reaction solution in a test tube, keeping the temperature in a water bath at 37 ℃ for 10min, adding 0.50mL of L-tyrosine solution respectively, reacting for 15min, quickly transferring into a cuvette, measuring the absorbance of each group at 475nm, and calculating the inhibition rate of the extraction solution with different polarity parts on tyrosinase.
The enzyme activity inhibition rate was [ (A2-A1) - (B2-B1) ]/(A2-A1) × 100%
A1 is the absorption value of no inhibitor at 0 min; a2 is the absorption value after 20min without inhibitor;
b1 is the absorption value of inhibitor added at 0 min; b2 is the absorption value of the inhibitor added after 20 min.
The inhibition rate and IC50 value of each effective part of radix Sophorae Flavescentis residue extract at six concentrations are shown in Table 1,
TABLE 1 tyrosinase activity inhibition rate and IC50 value of six concentrations of effective components of radix Sophorae Flavescentis residue extract
Example 3 evaluation of bacteriostatic Activity of effective fractions of Sophora flavescens Aiton residue extract
Dissolving the 10-80% ethanol eluate prepared in example 1 in methanol respectively to prepare 5mg/mL solution, and diluting to 2.500, 1.250, 0.625, 0.312, 0.156, and 0.078 mg/mL-1Six concentrations. Preparing qualitative filter paper into 6mm round piece with a puncher, placing into a dry culture dish, sterilizing with high pressure steam at 121 deg.C for 20min, and placing the filter paper piece into a sterilized culture dish. Dripping 5 μ L of medicinal liquid into each paper sheet, and drying in a drying oven to remove solvent. And uniformly coating the diluted bacteria liquid on LB agar by using a sterilized cotton swab, taking sterilized paper sheets, sequentially clamping the sterilized paper sheets by using a sterilized forceps, sequentially dipping the sterilized paper sheets on the agar, standing for 30min, culturing in an incubator at 37 ℃ for 24h, observing the size of a bacteriostatic zone, calculating an average value, and calculating the minimum bacteriostatic concentration (MIC). The results of the inhibitory activity of different elution parts of the sophora flavescens decoction dregs on staphylococcus aureus and streptococcus agalactiae are shown in a table 2.
TABLE 2 inhibitory Activity of effective fractions of Sophora flavescens Aiton residue extract against Staphylococcus aureus and Streptococcus agalactiae
The experimental results in tables 1 and 2 show that the extract obtained by extracting the sophora flavescens dregs can be subjected to AB-8 type macroporous resin chromatography, and particularly eluted by using ethanol with the volume concentration of 60%, so that the total flavone containing 8 different structural types can be obtained, and the content of the total flavone can reach more than 80%. The tyrosinase inhibitory activity and the antibacterial activity show that 60 percent of ethanol eluted substance has the best activity at the same time, and very good technical effect is achieved!
Example 4 preparation of whitening emulsion
1. Prepared according to the formulation of table 3: mixing the extracts in phase A, adding into 70 deg.C heated polyethylene glycol 400, adding glycerol and deionized water, and mixing;
dissolving B phase at 80 deg.C, and mixing; adding phase A into phase B, homogenizing for 10min, cooling to 50 deg.C, adding phase C, homogenizing for 5min, aging for 24 hr, and packaging.
TABLE 3 whitening lotion formulation table
2. Effect on B16F10 cell proliferation
The influence of whitening emulsion on B16F10 cell proliferation is observed through MTT experiment, the dosage of the whitening emulsion is set to be 5, 10, 20 and 40ug/ml according to the effective part of sophora flavescens decoction dregs, and the dosage of the whitening emulsion is set to be 5, 10, 20 and 40ug/ml according to the contrast medicament: the MTT experimental result of Table 4 shows that the whitening emulsion has a strong inhibition effect on B16F10 cell proliferation, and has a good proportional relation within a dosage range of 5-80 ug/ml, and after the administration of the whitening emulsion is carried out for 24 hours, the cell activity of a normal cell group is obviously weakened along with the prolonging of the culture time, which shows that the traditional Chinese medicine compound extracting solution has a strong inhibition effect on melanoma cells.
comparison with cell control group*P<0.05,**P<0.01
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (1)
1. The application of effective component of kuh-seng flavonoid with tyrosinase inhibitory activity and antibacterial activity; the application is the application in preparing whitening cosmetics, the application in preparing bacteriostatic agents and the application in preparing medicaments for preventing and treating human body pigmentation diseases or melanoma diseases caused by abnormal melanin;
the effective part of the kuh-seng flavonoid is prepared by the following method:
(1) drying and crushing the sophora flavescens dregs, adding 40-80% ethanol according to the material-liquid ratio of 1g to 10-50 ml, carrying out reflux extraction for 1-2 times, each time for 2 hours, and concentrating the extracting solution under reduced pressure to obtain a dry substance;
(2) dissolving the dried substance obtained in the step (1) with 95% ethanol, and filtering;
(3) and (3) concentrating the filtrate obtained in the step (2) under reduced pressure to obtain a dried substance, adding a small amount of methanol, ultrasonically dissolving, slowly adsorbing on an AB-8 type macroporous adsorption resin column, sequentially eluting with ethanol with volume concentration of 10%, 20%, 30%, 40%, 50%, 60%, 70% and 80% which is 5-8 times of the volume of the column, and collecting a 60% ethanol elution part.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811346769.3A CN109331061B (en) | 2018-11-13 | 2018-11-13 | Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811346769.3A CN109331061B (en) | 2018-11-13 | 2018-11-13 | Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109331061A CN109331061A (en) | 2019-02-15 |
CN109331061B true CN109331061B (en) | 2021-09-14 |
Family
ID=65314928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811346769.3A Active CN109331061B (en) | 2018-11-13 | 2018-11-13 | Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109331061B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113264912B (en) * | 2021-05-20 | 2023-07-04 | 中国热带农业科学院热带生物技术研究所 | Method for extracting 2- (2-phenethyl) chromone component from agilawood and application thereof |
CN118370763A (en) * | 2024-06-27 | 2024-07-23 | 山东方舟生物科技有限公司 | Application of isopentenyl flavonoid compound in kuh-seng extract in preparation of product for preventing and treating pathogenic bacteria of dairy cows |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101084989A (en) * | 2007-07-11 | 2007-12-12 | 石任兵 | Method for preparing general flavone and total alkaloid of sophora flavescens simultaneously |
CN103044424A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Method for enriching and purifying matrine in kuh-seng |
CN104771456A (en) * | 2014-01-15 | 2015-07-15 | 中国科学院上海生命科学研究院湖州营养与健康产业创新中心 | Application of bistort rhizome extract in inhibition of tyrosinase activity |
CN106008172A (en) * | 2016-05-18 | 2016-10-12 | 江南大学 | Preparation method and application of effective part with tyrosinase inhibition effect in mulberry twigs |
-
2018
- 2018-11-13 CN CN201811346769.3A patent/CN109331061B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101084989A (en) * | 2007-07-11 | 2007-12-12 | 石任兵 | Method for preparing general flavone and total alkaloid of sophora flavescens simultaneously |
CN103044424A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Method for enriching and purifying matrine in kuh-seng |
CN104771456A (en) * | 2014-01-15 | 2015-07-15 | 中国科学院上海生命科学研究院湖州营养与健康产业创新中心 | Application of bistort rhizome extract in inhibition of tyrosinase activity |
CN106008172A (en) * | 2016-05-18 | 2016-10-12 | 江南大学 | Preparation method and application of effective part with tyrosinase inhibition effect in mulberry twigs |
Non-Patent Citations (4)
Title |
---|
Comparative analysis of sixteen flavonoids from different parts of Sophora flavescens Ait. by ultra high-performance liquid chromatography–tandem mass spectrometry;ZebinWeng;《Journal of Pharmaceutical and Biomedical Analysis》;20180630;第156卷;全文 * |
甘草药渣中黄酮类成分及其抗氧化活性的研究;方诗琦;《中成药》;20151031;第37卷(第11期);全文 * |
苦参的成分及质量分析研究进展;陈静;《广东药学院学报》;20120531;第28卷(第5期);参见第569页最后一段,第570第1段 * |
酪氨酸酶抑制剂的研究进展;陈清西;《厦门大学学报(自然科学版)》;20071231;第46卷(第02期);第274页右栏最后2段,第275页第1段,右栏最后一段,第276页右栏第3段 * |
Also Published As
Publication number | Publication date |
---|---|
CN109331061A (en) | 2019-02-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Hussain et al. | Phytopharmacological potential of different species of Morus alba and their bioactive phytochemicals: A review | |
Milena et al. | Advantages of contemporary extraction techniques for the extraction of bioactive constituents from black elderberry (Sambucus nigra L.) flowers | |
Ismail et al. | Characterizing the phenolic constituents of baobab (Adansonia digitata) fruit shell by LC-MS/QTOF and their in vitro biological activities | |
CN101062077B (en) | Method for preparing stevia whole stevioside and stevia whole flavone at the same time | |
Feng et al. | Hypolipidemic and antioxidant effects of total flavonoids of Perilla Frutescens leaves in hyperlipidemia rats induced by high-fat diet | |
Dashora et al. | Antitumor activity of Dendrophthoe falcata against ehrlich ascites carcinoma in swiss albino mice | |
CN101336987B (en) | Preparation method of total flavone of Hovenia dulcisThunb | |
CN101062078B (en) | Extract of stevia whole stevioside and stevia whole flavone and the preparing method thereof | |
CN101336978B (en) | Extraction method of total flavone of Hovenia dulcisThunb | |
CN109331061B (en) | Kuh-seng flavonoid effective part with tyrosinase inhibitory activity and antibacterial activity, preparation method and application thereof | |
Arivukkarasu et al. | Detection and Quantification of Anti-oxidant markers like Rutin, Catechin, Quercetin, Gallic acid, Ellagic acid, Ferulic acid, Vitexin and Mangiferin in Herbal raw materials available in market belongs to Rutaceae family by HPTLC Technique | |
Dashora et al. | Antioxidant Activities of Dendrophthoe falcata (Lf) Etting | |
CN102321144A (en) | Method for extracting ursolic acid from red jujube | |
Kaur et al. | Metabolic fingerprinting of different populations of Phyllanthus niruri L. from Punjab using electrospray ionization mass spectrometry (ESI–MS) | |
CN104382968A (en) | Method for extracting common andrographis paniculata total lactone, pharmaceutical composition of andrographis paniculata total lactone and use of pharmaceutical composition | |
CN106333972B (en) | Antifatigue effective part extract of okra and its preparation method and application | |
CN101543505A (en) | Medicine for preventing and treating Alzheimer's disease and preparing method thereof | |
CN108042661B (en) | White tea extract rich in dihydromyricetin and application thereof in preparing medical health products | |
CN110194754A (en) | A kind of ligularia fischeri fat-soluble extract and its preparation method and application | |
Ajoko et al. | HPLC analysis and anti-inflammatory effect of methanol extract of the leaves of triumfetta cordifolia A. Rich.(Malvaceae) Available in Bayelsa State, Nigeria | |
US20130122119A1 (en) | Phyllanthus amarus compositions and method of extracting same | |
Supe et al. | HPLC method for analysis of bioactive compound from Momordica charantia | |
CN105646638B (en) | The preparation method of pedunculoside | |
EKEKE et al. | Phytochemical study on Commelina diffusa burn. F. Subsp. Diffusa JK Morton and Commelina erecta l.(commelinaceae) | |
Avello et al. | Identification of water-soluble compounds contained in aqueous extracts and fractions obtained from leaves of ugni molinae to determine their effect on the viability of human gastric cancer cells |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |