CN107510706A - 木棉花抗糖尿病活性组分的制备、组成及用途 - Google Patents
木棉花抗糖尿病活性组分的制备、组成及用途 Download PDFInfo
- Publication number
- CN107510706A CN107510706A CN201610425954.6A CN201610425954A CN107510706A CN 107510706 A CN107510706 A CN 107510706A CN 201610425954 A CN201610425954 A CN 201610425954A CN 107510706 A CN107510706 A CN 107510706A
- Authority
- CN
- China
- Prior art keywords
- common bombax
- bombax flower
- content
- diabetic
- group
- 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.)
- Pending
Links
- 241000219071 Malvaceae Species 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 230000003178 anti-diabetic effect Effects 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims abstract description 21
- AEDDIBAIWPIIBD-ZJKJAXBQSA-N mangiferin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC=2C(=CC(O)=C(O)C=2)C2=O)C2=C1O AEDDIBAIWPIIBD-ZJKJAXBQSA-N 0.000 claims abstract description 17
- -1 acyl tyrosine Chemical compound 0.000 claims abstract description 14
- 239000000284 extract Substances 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- WVLYNCZFGCFUAG-FUFTYFEXSA-N [(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-3-yl] 4-hydroxybenzoate Chemical compound O([C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO)C=1C(=C2C(=O)C3=CC(O)=C(O)C=C3OC2=CC=1O)O)C(=O)C1=CC=C(O)C=C1 WVLYNCZFGCFUAG-FUFTYFEXSA-N 0.000 claims abstract description 10
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims abstract description 10
- YWQSXCGKJDUYTL-UHFFFAOYSA-N Mangiferin Natural products CC(CCC=C(C)C)C1CC(C)C2C3CCC4C(C)(C)CCCC45CC35CCC12C YWQSXCGKJDUYTL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 229940043357 mangiferin Drugs 0.000 claims abstract description 8
- WVLYNCZFGCFUAG-UHFFFAOYSA-N muraxanthone Natural products OC1C(O)C(CO)OC(C=2C(=C3C(=O)C4=CC(O)=C(O)C=C4OC3=CC=2O)O)C1OC(=O)C1=CC=C(O)C=C1 WVLYNCZFGCFUAG-UHFFFAOYSA-N 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 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 claims description 8
- 235000005875 quercetin Nutrition 0.000 claims description 6
- 235000005493 rutin Nutrition 0.000 claims description 6
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims 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 claims description 4
- 239000003472 antidiabetic agent Substances 0.000 claims description 4
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 229930182478 glucoside Natural products 0.000 claims description 4
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 4
- 229960001285 quercetin Drugs 0.000 claims description 4
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims description 4
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims description 4
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims description 4
- 229960004555 rutoside Drugs 0.000 claims description 4
- VZPAURMDJZOGHU-UHFFFAOYSA-N N-benzoyl-L-phenylalanyl-L-phenylalaniol acetate Natural products C=1C=CC=CC=1CC(NC(=O)C=1C=CC=CC=1)C(=O)NC(COC(=O)C)CC1=CC=CC=C1 VZPAURMDJZOGHU-UHFFFAOYSA-N 0.000 claims description 3
- 108010080154 N-benzoylphenylalanylphenylalinol acetate Proteins 0.000 claims description 3
- JMFSHKGXVSAJFY-UHFFFAOYSA-N Saponaretin Natural products OCC(O)C1OC(Oc2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccc(O)cc4)C(O)C1O JMFSHKGXVSAJFY-UHFFFAOYSA-N 0.000 claims description 3
- MOZJVOCOKZLBQB-UHFFFAOYSA-N Vitexin Natural products OCC1OC(Oc2c(O)c(O)cc3C(=O)C=C(Oc23)c4ccc(O)cc4)C(O)C(O)C1O MOZJVOCOKZLBQB-UHFFFAOYSA-N 0.000 claims description 3
- VZPAURMDJZOGHU-DQEYMECFSA-N [(2s)-2-[[(2s)-2-benzamido-3-phenylpropanoyl]amino]-3-phenylpropyl] acetate Chemical compound C([C@@H](COC(=O)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=CC=CC=1)C1=CC=CC=C1 VZPAURMDJZOGHU-DQEYMECFSA-N 0.000 claims description 3
- GQZLXTLYIXYZIJ-ZEQRLZLVSA-N aurantiamide acetate Natural products CC(=O)OC[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)c2ccccc2)c3ccccc3 GQZLXTLYIXYZIJ-ZEQRLZLVSA-N 0.000 claims description 3
- MYXNWGACZJSMBT-VJXVFPJBSA-N isovitexin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC(=CC2=O)C=3C=CC(O)=CC=3)C2=C1O MYXNWGACZJSMBT-VJXVFPJBSA-N 0.000 claims description 3
- OYJCWTROZCNWAA-UHFFFAOYSA-N isovitexin Natural products OCC1OC(C(O)C(O)C1O)c2c(O)cc3CC(=CC(=O)c3c2O)c4ccc(O)cc4 OYJCWTROZCNWAA-UHFFFAOYSA-N 0.000 claims description 3
- 230000011218 segmentation Effects 0.000 claims description 3
- LEEDEKWKJVUWGA-YKXBDCQTSA-N trans-Dideoxyclovamide Chemical compound C([C@@H](C(=O)O)NC(=O)\C=C\C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LEEDEKWKJVUWGA-YKXBDCQTSA-N 0.000 claims description 3
- ODBRNZZJSYPIDI-UHFFFAOYSA-N 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=C(OC(=CC2=O)C=3C=C(O)C(O)=CC=3)C2=C1O ODBRNZZJSYPIDI-UHFFFAOYSA-N 0.000 claims description 2
- SLMMZNONABTNIB-DNQXCXABSA-N Aurantiamide Natural products OC[C@@H](Cc1ccccc1)NC(=O)[C@@H](CC(=O)c2ccccc2)Cc3ccccc3 SLMMZNONABTNIB-DNQXCXABSA-N 0.000 claims description 2
- KSVKECXWDNCRTM-UHFFFAOYSA-N Deacetyl-asperglaucid Natural products C=1C=CC=CC=1CC(NC(=O)C=1C=CC=CC=1)C(=O)NC(CO)CC1=CC=CC=C1 KSVKECXWDNCRTM-UHFFFAOYSA-N 0.000 claims description 2
- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 claims description 2
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 claims description 2
- 108010025480 aurantiamide Proteins 0.000 claims description 2
- ODBRNZZJSYPIDI-VJXVFPJBSA-N isoorientin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC(=CC2=O)C=3C=C(O)C(O)=CC=3)C2=C1O ODBRNZZJSYPIDI-VJXVFPJBSA-N 0.000 claims description 2
- OVSQVDMCBVZWGM-QCKGUQPXSA-N isoquercetin Natural products OC[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O OVSQVDMCBVZWGM-QCKGUQPXSA-N 0.000 claims description 2
- KSVKECXWDNCRTM-GOTSBHOMSA-N n-[(2s)-1-[[(2s)-1-hydroxy-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]benzamide Chemical compound C([C@@H](CO)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1C=CC=CC=1)C1=CC=CC=C1 KSVKECXWDNCRTM-GOTSBHOMSA-N 0.000 claims description 2
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- LEEDEKWKJVUWGA-AVFOEOQDSA-N (2s)-3-(4-hydroxyphenyl)-2-[[(z)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)\C=C/C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LEEDEKWKJVUWGA-AVFOEOQDSA-N 0.000 claims 1
- OVSQVDMCBVZWGM-LQSBFMDOSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-LQSBFMDOSA-N 0.000 claims 1
- 235000019082 Osmanthus Nutrition 0.000 claims 1
- 241000333181 Osmanthus Species 0.000 claims 1
- 235000013402 health food Nutrition 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 241000700159 Rattus Species 0.000 abstract description 59
- 210000004369 blood Anatomy 0.000 abstract description 37
- 239000008280 blood Substances 0.000 abstract description 37
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 34
- 239000008103 glucose Substances 0.000 abstract description 27
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 25
- 238000010828 elution Methods 0.000 abstract description 11
- 235000013305 food Nutrition 0.000 abstract description 9
- 206010022489 Insulin Resistance Diseases 0.000 abstract description 5
- 150000002989 phenols Chemical class 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 108020004414 DNA Proteins 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- 239000012071 phase Substances 0.000 description 21
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 235000000346 sugar Nutrition 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 230000036542 oxidative stress Effects 0.000 description 12
- 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 10
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical group O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 10
- 229960004346 glimepiride Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 102000004877 Insulin Human genes 0.000 description 9
- 108090001061 Insulin Proteins 0.000 description 9
- 229940125396 insulin Drugs 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 230000009182 swimming Effects 0.000 description 9
- LXEKPEMOWBOYRF-QDBORUFSSA-N AAPH Chemical compound Cl.Cl.NC(=N)C(C)(C)\N=N\C(C)(C)C(N)=N LXEKPEMOWBOYRF-QDBORUFSSA-N 0.000 description 8
- 235000001727 glucose Nutrition 0.000 description 8
- 241000628997 Flos Species 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000007760 free radical scavenging Effects 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- 230000005778 DNA damage Effects 0.000 description 6
- 231100000277 DNA damage Toxicity 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 6
- 108010023302 HDL Cholesterol Proteins 0.000 description 5
- 230000003064 anti-oxidating effect Effects 0.000 description 5
- 239000000401 methanolic extract Substances 0.000 description 5
- 239000013612 plasmid Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 108010028554 LDL Cholesterol Proteins 0.000 description 4
- 210000001015 abdomen Anatomy 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 238000003304 gavage Methods 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000003908 liver function Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 244000146553 Ceiba pentandra Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 208000004880 Polyuria Diseases 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 3
- 230000035619 diuresis Effects 0.000 description 3
- 238000001962 electrophoresis Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 2
- 235000003301 Ceiba pentandra Nutrition 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 206010018473 Glycosuria Diseases 0.000 description 2
- 241000186652 Sporosarcina ureae Species 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 125000005909 ethyl alcohol group Chemical group 0.000 description 2
- 206010016256 fatigue Diseases 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000037308 hair color Effects 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 230000037356 lipid metabolism Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 230000004792 oxidative damage Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- FZIPCQLKPTZZIM-UHFFFAOYSA-N 2-oxidanylpropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O FZIPCQLKPTZZIM-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
- 108010022579 ATP dependent 26S protease Proteins 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 244000293889 Bombax malabaricum Species 0.000 description 1
- 235000004480 Bombax malabaricum Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000522215 Dipteryx odorata Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 241001480055 Quercus mongolica Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- 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 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- YQYBUJYBXOVWQW-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 YQYBUJYBXOVWQW-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 102000016679 alpha-Glucosidases Human genes 0.000 description 1
- 108010028144 alpha-Glucosidases Proteins 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229930014669 anthocyanidin Natural products 0.000 description 1
- 150000001452 anthocyanidin derivatives Chemical class 0.000 description 1
- 235000008758 anthocyanidins Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000006075 aqueous methanolic extract Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940030275 epigallocatechin gallate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 150000002304 glucoses Chemical class 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012160 loading buffer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002552 multiple reaction monitoring Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 238000007410 oral glucose tolerance test Methods 0.000 description 1
- 210000004279 orbit Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 108700022737 rat Fat1 Proteins 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- JUJBNYBVVQSIOU-UHFFFAOYSA-M sodium;4-[2-(4-iodophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].C1=CC([N+](=O)[O-])=CC=C1N1[N+](C=2C=CC(I)=CC=2)=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=N1 JUJBNYBVVQSIOU-UHFFFAOYSA-M 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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)
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
本发明公开了一种木棉花的抗糖尿病活性组分,即木棉花醇提物经大孔树脂分段的甲醇‑水1:1洗脱部分。该组分富含酚类和酰胺类成分,这些成分的总含量占有效组分总重的70%以上,其中,原儿茶酸和芒果苷的含量分别大于20%,muraxanthone的含量大于10%,N‑对香豆酰酪氨酸的含量大于5%。该木棉花活性组分能够降低糖尿病大鼠血糖,改善糖耐量异常,增加胰岛素敏感性。本发明涉及该木棉花活性组分的制备、成分及生物活性特别是抗糖尿病活性,以及它们在药物、(功能)食品等方面的应用。
Description
技术领域
本发明属于天然药物领域,涉及木棉花的抗糖尿病活性组分、其组成成分及生物活性。
背景技术
随着生活节奏加快及生活习惯和饮食结构的改变,糖尿病患病率近年来急剧增加,估计患者人数9240万,糖尿病将成为继癌症和心脑血管疾病之后的第三大人类杀手[Yang, W.; Lu, J.; Wen,g J.; etc. Prevalence of diabetes among men and womenin China. The New England Journal of Medicine. 2010, 362(12): 1090-1101]。糖尿病患者的高血糖症往往伴随着血脂异常,引起血管、心、脑、肾等重要器官的损害,从而引发冠心病等心血管并发症[王学美. 2型糖尿病血脂异常的治疗进展[J]. 世界华人消化杂志, 2006, 14(4): 359-364.]。研究表明,胰岛素抵抗和胰岛β细胞功能受损是II型糖尿病的主要病因[任春久, 张瑶, 崔为正, 等. 氧化应激在2型糖尿病发病机制中的作用研究进展. 生理学报. 2013, 65(6): 664-673]。长期的高血糖症会增加活性氧(ROS)的产生,ROS可通过损伤β细胞DNA、线粒体等促进β细胞凋亡,也可通过产生过多脂质过氧化物损伤β细胞的结构和功能。ROS过剩和抗氧化能力不足还会导致氧化应激,氧化应激可以通过激活一系列应激信号通路而阻断胰岛素作用通路,从而导致胰岛素抵抗[刘颐轩, 宋桉, 王芸,等. 氧化应激在肥胖及胰岛素抵抗中的作用研究进展. 解放军医药杂志. 2014, 26(1):99-101; 李爱琴, 陆环, 徐文静, 等. 氧化应激与二型糖尿病的研究进展. 现代生物医学进展. 2010, 10(12): 2371-2371, 2378]。此外,研究表明,具有抗氧化、清除自由基作用的药物可以增强氧化防御系统的抗氧化力,通过改善β细胞的功能起到防治糖尿病及其并发症的功效[Jeong-Sook Lee. Effects of soy protein and genistein on bloodglucose, antioxidant enzyme activities, and lipid profile in streptozotocin-induced diabetic rats. Life Sciences, 2006, 79(16): 1578-1584]。
木棉花为木棉科木棉属植物木棉(Bombax malabaricum DC. 或B. ceiba L.)的干燥花。主产于我国广西、广东、四川、贵州和云南等省区及越南、缅甸、印度等地。民间采其花、皮与根,用于清热利湿、祛风除湿、活血消肿、散结止痛 [齐一萍, 郭舜民. 木棉的化学成分与药理作用研究. 福建医药杂志, 2002, 24(3): 119-120]。木棉花中含有花青素、黄酮、倍半萜类、酚类、类固醇、糖类以及氨基酸等,具有抗氧化、抗菌、保肝以及心脏保护及抗肿瘤的作用[Ali M. El-Hagrassi, Mamdouh M. Ali, Abeer F. Osman, etc.Phytochemical investigation and biological studies of Bombax malabaricumflowers. Nat Prod Res, 2011, 25(2): 141–151]等多种生理活性。
本发明公开木棉花单体化合物和4种粗提物的抗氧化活性以及木棉花主要活性部分(大孔树脂水-甲醇1:1洗脱部分,以下简称木棉花1:1相)对链脲佐菌素(STZ)诱导的糖尿病大鼠的治疗作用。木棉花1:1相能够改善糖尿病大鼠的状态(包括毛色、精神状态、饮水量、尿量等);降低糖尿病大鼠血糖,改善糖耐量异常,增加胰岛素敏感性;调节糖尿病大鼠脂代谢紊乱,提高抗氧化应激能力;对糖尿病大鼠的肝脏损伤也有一定的保护作用。
发明内容
本发明的目的在于提供对II型糖尿病有益的木棉花活性组分,内容包括:将木棉花醇提液浓缩后上DIAION HP20大孔树脂用水-甲醇梯度洗脱,1:1洗脱部位得到木棉花活性组分;该活性组分经糖尿病模型大鼠实验有抗糖尿病作用。
本发明还提供化学结构如图1所示的11种木棉花成分。这11种成分的名称分别为:原儿茶酸 (protocatechuic acid, 1)、芒果苷(mangiferin, 2)、muraxanthone (3)、N-反式对香豆酰酪氨酸(N-(E)-p-coumaroyltyrosine, 4)、N-顺式对香豆酰酪氨酸(N-(Z)-p-coumaroyltyrosine, 5)、木犀草素-6-C-葡萄糖苷( luteolin-6-C-glucoside, 6)、异槲皮素 (isoquercetin, 7)、异牡荆素 (isovitexin, 8)、芦丁(rutin, 9)、槲皮素(quercetin, 10)、橙黄胡椒酰胺(aurantiamide, 11)。
本发明还提供含上述木棉花成分的抗糖尿病活性组分及其药物制剂;本发明的又一个方面,提供木棉花成分作为抗氧化剂及在抗氧化方面的应用;另一个方面,本发明提供木棉花成分及其组合物用作药物及其在抗氧化应激和/或自由基的药物方面的应用。
本发明的再一方面,提供木棉花活性组分的制备方法,包括步骤如下:(1)木棉花粉碎后用溶剂(优选甲醇或70%乙醇)提取后过滤,滤液浓缩得提取物; (2)提取物悬浮于水中经大孔树脂粗分,分别用水、水-甲醇1:1和甲醇洗脱得到水相、水-甲醇1:1相、甲醇相。水-甲醇1:1相为活性组分,有很强的抗氧化活性并对糖尿病模型大鼠有明显的降血糖作用。
因此,本发明还涉及含有上述木棉花活性组分的组合物。本发明所述组合物,可按常规方法通过将所述木棉花活性组分与制作药物、食品或化妆品的载体混合来制备。
在本发明木棉花的活性组分及其用途的一个优选方案中,木棉花活性组分的制备方法和成分分析,包括以下步骤:
1)将木棉花用甲醇回流提取,提取液浓缩干燥后得木棉花甲醇提取物;
2)木棉花甲醇提取物悬浮于水中经14-15倍 (树脂ml:提取物g) DIAION HP20大孔树脂分段,大孔树脂用2倍量水洗脱后用4倍量水-甲醇1:1洗脱,水-甲醇1:1洗脱部分为活性组分;
3)对活性组分中的主要成分进行定量分析,图1中的化合物1-11总含量为70%-85%,其中,原儿茶酸和芒果苷的含量分别大于20%, muraxanthone (6)的含量大于10%,N-对香豆酰酪氨酸的含量大于5%(反式的含量高于顺式的)。
本发明的创造性和新发现为:得到了具有明显降低糖尿病大鼠血糖水平的木棉花活性组分,即醇提取物大孔树脂的甲醇-水1:1洗脱部分,其中,原儿茶酸和芒果苷的含量分别大于20%,muraxanthone的含量大于10%,酚类化合物总含量大于70%。木棉花1:1相给药(200 mg/kg)3周后,能够改善糖尿病大鼠消瘦、精神不振、多饮、多食和多尿等症状;显著降低空腹血糖水平(P<0.01),改善糖耐量及胰岛素耐量异常,维持体内葡萄糖稳定,增加机体对外源胰岛素的敏感性;改善脂代谢紊乱;血浆转氨酶水平明显降低,说明对糖尿病大鼠的肝脏的具有一定的保护作用;调节氧化应激水平,SOD活性增强,MDA水平降低。另外,1:1相及木棉花的6个成分(1-3, 7, 9-10)显示很强的清除DPPH自由基的能力,并且对过氧自由基引起的DNA损伤具有明显的保护作用。化合物1和10表现出了良好的抑制麦芽糖酶活性。
附图说明
图1是木棉花抗糖尿病有效组分的主要成分结构图
图2是内标化合物ISa和ISb的结构图
图3是木棉花提取物的UHPLC-MS图;由上到下依次为1:1相、甲醇相、水相和甲醇提取物(1原儿茶酸、2芒果苷、3 muraxanthone、4 N-反式对香豆酰酪氨酸、5 N-顺式对香豆酰酪氨酸、6木犀草素-6-C-葡萄糖苷、7 异槲皮素、8异牡荆素、9芦丁、10槲皮素、11橙黄胡椒酰胺)
图4是化合物1,2,10抑制ROO•诱导的DNA损伤作用图;泳道1:正常DNA;泳道2:DNA中加入22.5 mM AAPH; 泳道3-5:分别为DNA中加入化合物1,2,10(1 mM)和22.5 mM AAPH。泳道4的条带过亮是因为化合物本身具有荧光
图5是化合物2,7,9抑制ROO•诱导的DNA损伤作用图;泳道1:正常DNA;泳道2:DNA中加入22.5 mM AAPH; 泳道4-6:分别为DNA中加入化合物2,7,9(1 mM)和22.5 mM AAPH
具体实施方式
具体实施方式对本发明涉及的木棉花活性组分的制备、组成和活性作详细说明。这些实施例仅用来例证,而不是对本发明保护范围的限制。
实施例1:木棉花活性组分的制备
木棉花(420g)甲醇回流提取浓缩后经大孔树脂(120×540 mm)分段,先后用水(14000 ml)、水-甲醇1:1(24000 ml)、甲醇(14000 ml)洗脱,3部分洗脱液减压浓缩后分别得到水相(180 g)、1:1相(80 g)和甲醇相(130 g)。活性研究证明1:1相为木棉花抗糖尿病活性组分。
实施例2:木棉花提取物及大孔树脂所得组分中各成分的含量
选用的图2所示的酚类化合物ISa和酰胺化合物ISb为内标化合物,其中ISb用于化合物4, 5, 11的定量,ISa用于其他成分的定量。
将活性组分1:1相等样品溶于含内标(10 μg/mL的ISa, 100 μg/mL的 ISb)甲醇中,0.22 μm微滤至进样瓶备用。标准品化合物溶于DMSO配制成10 μg/mL的储备液。混合后,稀释成9个浓度梯度,加入内标使所有溶液均含10 μg/mL的ISa和100 μg/mL的 ISb。
UPLC条件:流动相A为含0.1%的甲酸的超纯水,B为色谱纯甲醇。洗脱程序为:0min, 20% B; 1 min, 27% B; 2 min, 28.3% B; 6.5 min, 28.3% B; 8 min, 100% B; 10min, 100% B。流速为0.4 mL/min,进样量为2 µL,柱温为30 °C。
MS条件:采用多反应监测模式(MRM),毛细管电压4 kV,雾化器压力45 psi,干燥气流速11 L·min-1,电喷雾离子源温度350 °C。MRM模式下化合物的优化条件如表1所示。图3为木棉花甲醇提取物及大孔树脂各洗脱部分在MRM模式下的UHPLC-MS图;
表1定量成分的优化MRM条件
表2 木棉花提取物及各组分中11个主要化合物的含量(mg/g)
化合物 | 甲醇提取物 | 水相 | 1:1相 | 甲醇相 |
1 | 60.44±2.70 | 5.72±0.45 | 235.48±9.45 | 3.64±0.07 |
2 | 47.51±2.58 | 1.44±0.10 | 232.26±8.08 | 3.72±0.04 |
3 | 14.42±1.01 | 0.11±0.00 | 103.93.±1.11 | ND |
4 | 4.77±0.34 | 0.35±0.02 | 41.66±1.09 | 0.92±0.02 |
5 | 4.92±0.54 | 0.80±0.03 | 18.76±1.40 | 0.83±0.10 |
6 | 4.00±0.30 | ND | 27.96±2.07 | 0.18±0.01 |
7 | 2.59±0.06 | 0.33±0.01 | 19.05±1.14 | 0.22±0.01 |
8 | 3.35±0.35 | 0.09±0.00 | 18.49±2.02 | 0.79±0.03 |
9 | 1.24±0.04 | 0.38±0.02 | 8.11±0.18 | 0.17±0.01 |
10 | 1.90±0.13 | 0.05±0.00 | 0.29±0.01 | 7.60±0.37 |
11 | 0.61±0.01 | ND | 0.01±0.00 | 2.15±0.03 |
总含量 | 706 |
ND: 检测不到
1原儿茶酸、2芒果苷、3 muraxanthone、4 N-反式对香豆酰酪氨酸、5 N-顺式对香豆酰酪氨酸、6木犀草素-6-C-葡萄糖苷、7异槲皮素、8 异牡荆素、9 芦丁、10槲皮素、11橙黄胡椒酰胺
用建立的MRM定量方法测定各浓度梯度的混合标准品,以待测化合物与内标的面积比为纵坐标,待测化合物浓度为横坐标,建立标准曲线,测定样品后通过标准曲线计算样品中各化合物的含量。
用上述优化的定量条件对木棉花甲醇提取物及大孔树脂各流份分析结果列于表2; 其中,1:1相的成分含量最高。
实施例3:木棉花抗氧化活性
1,1-二苯基苦基苯肼(DPPH)自由基清除实验
96孔板中加入10 μL样品无水乙醇溶液(1 μg/mL)和190 μL DPPH溶液(0.1 mM),室温下避光反应20 min,酶标仪520 nm下测定各孔吸光值(A)。空白对照用10 μL无水乙醇和190 μL DPPH溶液(0.1 mM );颜色对照用10 μL样品(1 μg/mL)和190 μL无水乙醇。DPPH清除率计算公式如下:
对DPPH自由基清除率%=100×[A对照- (A样品–A颜色对照)] /A对照
A对照为对照孔的吸光度, A样品为样品孔的吸光度, A颜色对照为颜色对照孔的吸光度;
清除率在50%以上的样品进一步稀释后再测定对DPPH自由基清除率。以样品终浓度(50、25、12.5、6.25、3.125 μg/mL)和对应清除率建立标准曲线,计算EC50(清除率达到50%时的样品终浓度)表3;
表3 木棉花主要成分的自由基清除活性
抑制 ROO•诱导的DNA氧化损伤作用
根据天根质粒小提试剂盒提取超螺旋质粒pUC18,所用菌种是大肠杆菌BL21。抑制DNA氧化损伤实验参考文献[Y. Zhong, F. Shahidi. Lipophilised epigallocatechingallate (EGCG) derivatives and their antioxidant potential in food andbiological systems. Food Chemistry, 2012, 131(1): 22–30]。利用过氧游离基(ROO•)造成超螺旋质粒DNA的损伤,通过凝胶电泳检测断裂的DNA链,测定化合物对ROO•的清除作用。所用试剂为:0.5 M的磷酸钠缓冲液(PBS, PH=7.4); 22.5 mM的AAPH 溶液; 120 ng/mL的超螺旋质粒DNA pUC18溶液; 1 mM的化合物溶液。具体实验过程如下:
样品组:2 μL DNA+4 μL AAPH+2 μL待测化合物+2 μL PBS
空白对照组:2 μL DNA+6 μL超纯水+2 μL PBS
损伤对照组:2 μL DNA+4 μL AAPH+2 μL超纯水+2 μL PBS
混合溶液在37℃黑暗培养1小时后加入2 μL的上样缓冲液混匀后进行电泳。0.7% (w/v)琼脂糖用PH 8.5的TAE电泳缓冲液(2 M Tris-醋酸,100 mM EDTA)配制,溶胶后加入核酸染料(1 mM,胶与核酸染料比例是10 mL:1 μL)。80 V电压下电泳40 min,然后置于全自动凝胶成像分析系统中观察拍照。
环状质粒DNA以超螺旋的状态存在,DNA受到过氧自由基的损伤后会开环,严重损伤的DNA会变成线性。这三种不同构型分子进行电泳时的迁移速率由大到小为:环状超螺旋DNA>线型DNA>开环DNA。图4和图5中的泳道1为DNA的正常超螺旋状态,泳道2为加入22.5 mM的AAPH后DNA的损伤状态。结果表明,化合物1、2、7、9和10均可增强DNA超螺旋状态的保留,说明可以清除ROO•,从而保护DNA免受损伤。
实验显示,酚酸和黄酮类化合物显示了较强的DPPH自由基清除活性,富含这类成分的1:1相具有较强的DPPH自由基清除活性。
细胞中的羟自由基和过氧自由基等活性氧引起氧化应激,造成DNA损伤,从而引起突变和癌变[M. Valkoa, C. J. Rhodesb, J. Moncola, etc. Free radicals, metalsand antioxidants in oxidative stress-induced cancer. Chemico-BiologicalInteractions, 2006, 160 (1): 1-40]。本实验对具有DPPH自由基清除活性的化合物进行了抑制DNA损伤活性测试,发现化合物(1, 2, 7, 9, 10)对DNA损伤具有很好的抑制作用,表明这些化合物可作为潜在的抗突变剂。
实施例4:木棉花活性组分对糖尿病大鼠的降血糖作用
研究了预实验中活性最好的1:1相对糖尿病大鼠的降血糖作用。50只大鼠适应性喂养一周后随机抽取6只作为正常组,给予普通饲料,其余大鼠用高脂饲料喂养。4周后,大鼠禁食12 h,高脂饲料组按45 mg/kg的剂量腹腔注射1%的链脲佐菌素(STZ)柠檬酸-柠檬酸钠缓冲液(0.1 M,PH=4.2 - 4.5),正常组注射等体积的缓冲液。5天后大鼠禁食不禁水12h,尾部采血,用血糖仪及血糖试纸检测血糖,以空腹血糖≧12视为造模成功。
高脂饲料喂养组大鼠随机分为糖尿病模型组、格列美脲组和给药组。其中给药组每组8只大鼠,正常组、模型组和格列美脲组每组6只大鼠。1:1相给药剂量为200 mg/kg,格列美脲给药量定为1.5 mg/kg,模型组和正常组灌胃等量纯净水,继续原喂养方式给药3周。给药期间,每周观察大鼠的精神状态、毛色、进食量、进水量和排尿量等,并且每周测一次空腹血糖。
糖耐量实验(OGTT):给药3周后,大鼠禁食不禁水12 h,以2g/kg剂量灌胃50%葡萄糖溶液,于灌胃前(0 min),灌胃后30、60、和120 min测定血糖。
胰岛素耐量实验(ITT):糖耐量实验1天后,血糖基本稳定,禁食不禁水12 h,腹部皮下注射0.5 U/kg胰岛素的生理盐水溶液,测定注射前(0 min),及注射后30、60、和120min各时间点血糖。以0 min血糖为100%,计算各时间点血糖变化。
生化指标检测:总胆固醇(T-CHO)测试盒(序号A111-1)、甘油三酯(TG)测试盒(A110-1)、高密度脂蛋白胆固醇(HDL-C)测试盒(序号A112-1)、低密度脂蛋白胆固醇(LDL-C)测试盒(序号A113-1)、丙二醛(MDA)测定试剂盒(TBA法, 序号A003-1)、总超氧化物歧化酶(SOD)测定试剂盒(WST-1法,序号A001-3)均购于南京建成生物工程研究。大鼠血糖回升稳定后,禁食不禁水12 h,乙醚麻醉,眼眶取血,低温离心5 min(13500转)。取上清得血清,分装保存备用。取血后迅速取下胰腺并将周围组织分离,从相同部位取下胰腺1 g,生理盐水冲洗干净,在1 mL冰生理盐水中匀浆,剩余部分于-80 ℃保存备用。用试剂盒对大鼠血清的氧化应激指标SOD活力和MDA, 血脂指标TC、TG、LDL-C和HDL-C,及肝功能指标AST和ALT进行检测。
木棉花1:1相对糖尿病大鼠状态的影响:与正常组大鼠相比,糖尿病大鼠反应迟钝、精神不振、毛色暗淡、无光泽,并且出现多饮、多食、多尿和尿糖等症状。给药三周后,与模型组相比,给药各组和格列美脲组大鼠毛色光泽改善,并且饮水量和尿量减少。
木棉花1:1相对糖尿病大鼠空腹血糖状况的影响:如表4所示,在造模后给药前正常组的血糖水平显著低于其他各组(P<0.01),并且给药组各组和模型组没有明显差异(P>0.05),说明本实验中糖尿病大鼠模型建立成功。
表4 各组大鼠空腹血糖比较
在给药1周、2周和3周后,给药组大鼠的血糖较给药前均有所降低,在第3周时降低了16%,并且低于格列美脲组(阳性对照组)。给药组大鼠随着给药时间的增加血糖水平也在降低,在给药第二周和第三周血糖水平已经显著低于模型组(P<0.01)。格列美脲组给药两周和三周后血糖较第一周升高,但与模型组相比仍有显著性差异(P<0.05),这可能是由于大鼠胰岛细胞遭到破坏,胰岛素分泌不足,导致难以发挥格列美脲的降糖作用。
木棉花活性组分对糖尿病大鼠葡萄糖耐量的影响:表5表示各组大鼠口服葡萄糖后120分钟内血糖变化。结果表明,所有组大鼠在口服葡萄糖后30 min内血糖均达到最高值,之后又逐渐下降,其中正常组和给药组在120 min后血糖逐渐下降到口服葡萄糖前的水平(0 min),表现出了较好的降糖作用,而模型组和格列美脲组在30-120 min内血糖虽然有所降低,但仍高于口服葡萄糖前的水平。正常组和给药组大鼠血糖水平在各时间点均显著低于模型组(P<0.01或P<0.05);
表5 各组大鼠的葡萄糖耐量比较
木棉花提取物对糖尿病大鼠胰岛素耐量的影响:表6表示各组大鼠腹部皮下注射胰岛素(Ins)后120分钟内血糖变化。分析结果可知,正常组和给药各时间点血糖与模型组相比存在显著差异(P<0.01或P<0.05),各组大鼠在注射Ins后血糖水平均下降,其中正常组、给药组和格列美脲组在注射30 min后变化率较大,在60 min时各组大鼠血糖变化更为显著,分别降低了39.8%,31.7%和20.1%,而模型组只下降了3.5%,说明木棉花1:1相和格列美脲可显著增强糖尿病大鼠对外源性胰岛素的敏感性;
表 6各组大鼠的胰岛素耐量比较
木棉花提取物对糖尿病大鼠血脂水平的影响:表7显示了各组大鼠的血脂水平,分析结果可知,与正常组相比,模型组大鼠的LDL-C、TC、TG显著升高(P<0.01),HDL-C显著下降(P<0.05),说明模型组大鼠血脂存在异常。给药3周后,木棉花1:1相给药组和格列美脲组LDL-C、HDL-C、TC和TG水平均有所改善;
表7各组大鼠血脂的比较
木棉花提取物对糖尿病大鼠肝脏功能的影响:表8显示的是各组大鼠的丙氨酸转氨酶(ALT)和谷草转氨酶(AST)值比较。分析数据可知,模型组大鼠AST和ALT的值明显大于正常组(P<0.01),说明糖尿病大鼠肝功能明显受损。给药组的AST和ALT较模型组均有显著降低(P<0.01),说明给药组可以有效改善糖尿病大鼠肝脏损伤;
表8各组大鼠肝功能的比较
木棉花提取物对糖尿病大鼠氧化应激指标的影响:表9显示的是各组大鼠SOD活力和MDA含量。模型组大鼠MDA含量显著高于正常组(P<0.01),SOD活力显著低于正常组(P<0.01),表明模型组大鼠的过氧化水平显著升高,处于氧化应激状态。与模型组相比,给药组和格列美脲组MDA含量显著降低(P<0.01或P<0.05),SOD活力显著升高(P<0.01),说明1:1相能提高糖尿病大鼠抗氧化能力,调整氧化应激状态;
表9 各组大鼠SOD和MDA比较
由于上述实例所述木棉花活性组分及其大多数成分均有清除自由基活性,该活性组分对实验动物还有很好的降血糖作用,所以该活性组分及纯成分预期对糖尿病患者有益;
本实验得到木棉花活性组分的方法简单,制备条件温和,适用于大批量生产。
上述仅为本发明较佳的具体实施方法,本发明保护范围不应受此限制,熟悉本领域的技术人员在本发明的技术范围内,以简单变化或替换所得的技术方案均落入本发明的保护范围。
Claims (4)
1.一种木棉花的抗糖尿病有效组分,其主要成分为原儿茶酸 (protocatechuic acid,1)、芒果苷(mangiferin, 2)、muraxanthone (3)、N-反式对香豆酰酪氨酸(N-(E)-p-coumaroyltyrosine, 4)、N-顺式对香豆酰酪氨酸(N-(Z)-p-coumaroyltyrosine, 5)、木犀草素-6-C-葡萄糖苷( luteolin-6-C-glucoside, 6)、异槲皮素 (isoquercetin, 7)、异牡荆素 (isovitexin, 8)、芦丁(rutin, 9)、槲皮素(quercetin, 10)、橙黄胡椒酰胺(aurantiamide, 11)。这些成分的总含量占有效组分总重的70%-85%,其中,原儿茶酸(1)和芒果苷(2)的含量分别大于20%,muraxanthone (3)的含量大于10%,N-对香豆酰酪氨酸(4,5)的含量大于5%(反式的含量高于顺式)。
2.权利要求1所述木棉花抗糖尿病活性组分的制备方法,包括木棉花醇提物的制备,大孔树脂分段,水洗去高极性杂质,水-甲醇1:1洗脱物为抗糖尿病活性组分。
3.权利要求2所述的提取溶剂为甲醇或乙醇或其含水或不含水的混合溶剂。
4.权利要求1所述木棉花活性组分在抗糖尿病的保健食品或药品中的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610425954.6A CN107510706A (zh) | 2016-06-15 | 2016-06-15 | 木棉花抗糖尿病活性组分的制备、组成及用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610425954.6A CN107510706A (zh) | 2016-06-15 | 2016-06-15 | 木棉花抗糖尿病活性组分的制备、组成及用途 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN107510706A true CN107510706A (zh) | 2017-12-26 |
Family
ID=60720991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610425954.6A Pending CN107510706A (zh) | 2016-06-15 | 2016-06-15 | 木棉花抗糖尿病活性组分的制备、组成及用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107510706A (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109021035A (zh) * | 2018-09-18 | 2018-12-18 | 云南中烟工业有限责任公司 | 一种苯乙酰胺类化合物、其制备方法和用途 |
EP3737390A4 (en) * | 2018-01-10 | 2021-12-01 | Brightseed, Inc. | COMPOSITION FOR MODULATING METABOLISM |
EP3737389A4 (en) * | 2018-01-10 | 2021-12-01 | Brightseed, Inc. | METHOD OF MODULATING METABOLISM |
US11647776B2 (en) | 2019-11-11 | 2023-05-16 | Brightseed, Inc. | Extract, consumable product and method for enriching bioactive metabolite in an extract |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1903236A (zh) * | 2006-08-04 | 2007-01-31 | 朱海芸 | 具有抗糖尿病活性的药物组合物 |
CN102119942A (zh) * | 2011-03-04 | 2011-07-13 | 中国药科大学 | 木棉叶总酚提取物、其制备方法和治疗2型糖尿病的应用 |
-
2016
- 2016-06-15 CN CN201610425954.6A patent/CN107510706A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1903236A (zh) * | 2006-08-04 | 2007-01-31 | 朱海芸 | 具有抗糖尿病活性的药物组合物 |
CN102119942A (zh) * | 2011-03-04 | 2011-07-13 | 中国药科大学 | 木棉叶总酚提取物、其制备方法和治疗2型糖尿病的应用 |
Non-Patent Citations (1)
Title |
---|
李旭森等: "木棉的化学成分及药理作用研究进展", 《中国野生植物资源》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3737390A4 (en) * | 2018-01-10 | 2021-12-01 | Brightseed, Inc. | COMPOSITION FOR MODULATING METABOLISM |
EP3737389A4 (en) * | 2018-01-10 | 2021-12-01 | Brightseed, Inc. | METHOD OF MODULATING METABOLISM |
US11642323B2 (en) | 2018-01-10 | 2023-05-09 | Brightseed, Inc. | Method for modulating metabolism |
CN109021035A (zh) * | 2018-09-18 | 2018-12-18 | 云南中烟工业有限责任公司 | 一种苯乙酰胺类化合物、其制备方法和用途 |
CN109021035B (zh) * | 2018-09-18 | 2021-04-06 | 云南中烟工业有限责任公司 | 一种苯乙酰胺类化合物、其制备方法和用途 |
US11647776B2 (en) | 2019-11-11 | 2023-05-16 | Brightseed, Inc. | Extract, consumable product and method for enriching bioactive metabolite in an extract |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Li et al. | HPLC fingerprint analysis of Phyllanthus emblica ethanol extract and their antioxidant and anti-inflammatory properties | |
Wang et al. | Efficient extraction of flavonoids from Flos Sophorae Immaturus by tailored and sustainable deep eutectic solvent as green extraction media | |
Deng et al. | Phenolic compounds and bioactivities of pigmented rice | |
CN103816296B (zh) | 紫珠总苷提取物及其制备方法和用途 | |
CN101181317B (zh) | 马齿苋提取物及其制备方法和用途 | |
CN104940049B (zh) | 雪莲果植物提取物的提取方法、提取物及应用 | |
CN107510706A (zh) | 木棉花抗糖尿病活性组分的制备、组成及用途 | |
Zhang et al. | α-Glucosidase inhibitory activity by the flower buds of Lonicera japonica Thunb | |
CN104825463B (zh) | 白肉灵芝提取物的代谢调节及抗缺氧的用途 | |
CN110615821A (zh) | 一种桑葚提取物、提取分离方法及其应用 | |
CN104523479B (zh) | 青刺尖提取物在美白用品中的应用及美白用品 | |
CN106798762A (zh) | 一种植物提取物及其制备方法和应用 | |
CN101401829A (zh) | 一种野金柴活性提取物及其制备方法和应用 | |
CN109288760A (zh) | 一种植物精粹面霜及其制备方法 | |
CN109364073A (zh) | 一种荜茇酰胺生物碱在制备治疗白癜风中促进黑色素生成的药物中的用途 | |
CN105030914B (zh) | 粗壮女贞苦丁茶提取物在α-葡萄糖苷酶抑制剂的应用 | |
CN103446278A (zh) | 一种海棠提取物及其制备、应用 | |
Wang et al. | Hypoglycemic effect of Camellia chrysantha extract on type 2 diabetic mice model | |
CN102370674A (zh) | 一种桑寄生提取物及其制备方法与应用 | |
CN105012826A (zh) | 一种益智叶提取物及其制备方法、应用 | |
CN104926958A (zh) | 从泽兰中提取泽兰多糖的方法及其应用 | |
CN103664568B (zh) | 环草石斛二聚芪类化合物及其制备方法和应用 | |
CN104257756B (zh) | 一种桑白皮脂肪油在制备降糖药物中的应用 | |
CN113730466A (zh) | 一种黑莓提取物的制备方法及其应用 | |
Jun et al. | Antioxidant, anti‐inflammatory, and anticancer function of Engleromyces goetzei Henn aqueous extract on human intestinal Caco‐2 cells treated with t‐BHP |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20171226 |
|
RJ01 | Rejection of invention patent application after publication |