CN102389440A - 环烯醚萜类化合物在制备抗骨质疏松药物中的应用 - Google Patents
环烯醚萜类化合物在制备抗骨质疏松药物中的应用 Download PDFInfo
- Publication number
- CN102389440A CN102389440A CN2011104085645A CN201110408564A CN102389440A CN 102389440 A CN102389440 A CN 102389440A CN 2011104085645 A CN2011104085645 A CN 2011104085645A CN 201110408564 A CN201110408564 A CN 201110408564A CN 102389440 A CN102389440 A CN 102389440A
- Authority
- CN
- China
- Prior art keywords
- iridoid
- chemical compound
- ligustri lucidi
- fructus ligustri
- gets
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 title abstract description 13
- 230000003262 anti-osteoporosis Effects 0.000 title abstract description 7
- 229940079593 drug Drugs 0.000 title abstract 5
- 230000000694 effects Effects 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 210000004027 cell Anatomy 0.000 claims abstract description 46
- 239000000284 extract Substances 0.000 claims abstract description 34
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 230000004069 differentiation Effects 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000010828 elution Methods 0.000 claims description 18
- 238000000605 extraction Methods 0.000 claims description 18
- 210000004409 osteocyte Anatomy 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000010898 silica gel chromatography Methods 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000013641 positive control Substances 0.000 claims description 9
- 238000004809 thin layer chromatography Methods 0.000 claims description 9
- 229960005309 estradiol Drugs 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 claims description 5
- 230000024245 cell differentiation Effects 0.000 claims description 5
- 230000003595 spectral effect Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229930182833 estradiol Natural products 0.000 claims description 4
- SMSRUMQQXKEQCV-VDXFDKNHSA-N nuezhenoside G13 Natural products COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=CC)[C@H]1CC(=O)Oc3ccc(CCO[C@@H]4O[C@H](COC(=O)C[C@H]5C(=CC)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)OC=C5C(=O)OC)[C@@H](O)[C@H](O)[C@H]4O)cc3 SMSRUMQQXKEQCV-VDXFDKNHSA-N 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 235000013399 edible fruits Nutrition 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012567 medical material Substances 0.000 claims description 3
- 241000830535 Ligustrum lucidum Species 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 abstract description 20
- 102000002260 Alkaline Phosphatase Human genes 0.000 abstract description 15
- 108020004774 Alkaline Phosphatase Proteins 0.000 abstract description 15
- 210000000963 osteoblast Anatomy 0.000 abstract description 8
- 238000002474 experimental method Methods 0.000 abstract description 7
- STKUCSFEBXPTAY-GSUVRYNNSA-N methyl (4s,5z,6s)-5-ethylidene-4-[2-oxo-2-[[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy]ethyl]-6-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4h-pyran-3-carboxylate Chemical compound O([C@@H]\1OC=C([C@H](C/1=C/C)CC(=O)OC[C@@H]1[C@H]([C@H](O)[C@@H](O)[C@H](OCCC=2C=CC(O)=CC=2)O1)O)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O STKUCSFEBXPTAY-GSUVRYNNSA-N 0.000 abstract description 7
- 230000001737 promoting effect Effects 0.000 abstract description 4
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 3
- 230000004072 osteoblast differentiation Effects 0.000 abstract description 3
- 102000004169 proteins and genes Human genes 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- -1 ether terpenoid Chemical class 0.000 description 10
- 238000001514 detection method Methods 0.000 description 9
- 210000000988 bone and bone Anatomy 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000001963 growth medium Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012224 working solution Substances 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000031700 light absorption Effects 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 230000001582 osteoblastic effect Effects 0.000 description 4
- 210000002997 osteoclast Anatomy 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 244000309466 calf Species 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- STKUCSFEBXPTAY-UHFFFAOYSA-N (8E)-nuezhenide Natural products CC=C1C(CC(=O)OCC2C(C(O)C(O)C(OCCC=3C=CC(O)=CC=3)O2)O)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O STKUCSFEBXPTAY-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 210000002805 bone matrix Anatomy 0.000 description 2
- 239000012930 cell culture fluid Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- 230000001009 osteoporotic effect Effects 0.000 description 2
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 230000011218 segmentation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical class OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 102000055006 Calcitonin Human genes 0.000 description 1
- 108060001064 Calcitonin Proteins 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010010582 Congenital osteodystrophy Diseases 0.000 description 1
- 208000007652 Dysostoses Diseases 0.000 description 1
- 201000001324 Dysostosis Diseases 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000201295 Euphrasia Species 0.000 description 1
- YPZRHBJKEMOYQH-UYBVJOGSSA-N FADH2 Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1COP(O)(=O)OP(O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C(NC(=O)NC2=O)=C2NC2=C1C=C(C)C(C)=C2 YPZRHBJKEMOYQH-UYBVJOGSSA-N 0.000 description 1
- YTNIXZGTHTVJBW-SCRDCRAPSA-N FMNH2 Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2NC2=C1NC(=O)NC2=O YTNIXZGTHTVJBW-SCRDCRAPSA-N 0.000 description 1
- 206010017076 Fracture Diseases 0.000 description 1
- 108010033040 Histones Proteins 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- 241000735234 Ligustrum Species 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000013275 Somatomedins Human genes 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 208000012886 Vertigo Diseases 0.000 description 1
- 206010047531 Visual acuity reduced Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 206010006007 bone sarcoma Diseases 0.000 description 1
- 230000037118 bone strength Effects 0.000 description 1
- 229960004015 calcitonin Drugs 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000002279 cholagogic effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 238000012850 discrimination method Methods 0.000 description 1
- TYJOJLOWRIQYQM-UHFFFAOYSA-L disodium;phenyl phosphate Chemical compound [Na+].[Na+].[O-]P([O-])(=O)OC1=CC=CC=C1 TYJOJLOWRIQYQM-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002121 endocytic effect Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035806 respiratory chain Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 108010048734 sclerotin Proteins 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229940041022 streptomycins Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 238000003805 vibration mixing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Images
Landscapes
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110408564.5A CN102389440B (zh) | 2011-12-09 | 2011-12-09 | 环烯醚萜类化合物在制备抗骨质疏松药物中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110408564.5A CN102389440B (zh) | 2011-12-09 | 2011-12-09 | 环烯醚萜类化合物在制备抗骨质疏松药物中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102389440A true CN102389440A (zh) | 2012-03-28 |
CN102389440B CN102389440B (zh) | 2014-08-20 |
Family
ID=45856905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201110408564.5A Expired - Fee Related CN102389440B (zh) | 2011-12-09 | 2011-12-09 | 环烯醚萜类化合物在制备抗骨质疏松药物中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102389440B (zh) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105330710A (zh) * | 2015-10-23 | 2016-02-17 | 大连医科大学 | 一种从女贞子中同时提取三种环烯醚萜苷类化学对照品的方法 |
CN106466325A (zh) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | 一种预防或治疗糖尿病的药物、组合物及其制剂 |
CN106632544A (zh) * | 2016-12-21 | 2017-05-10 | 上海诗丹德标准技术服务有限公司 | 一种特女贞苷对照品的制备方法 |
CN106728679A (zh) * | 2016-12-30 | 2017-05-31 | 福建中医药大学 | 一种用于抗骨量丢失的分子中药缓释片及其制备方法 |
CN108823158A (zh) * | 2018-07-05 | 2018-11-16 | 浙江大学 | 女贞苷和特女贞苷在促进体外培养骨髓间充质干细胞增殖和抑制复制性衰老中的应用 |
CN109265467A (zh) * | 2018-11-07 | 2019-01-25 | 扬州工业职业技术学院 | 一种中药女贞子来源的七环内酯化合物及其作为抗老年痴呆药物的应用 |
CN109608510A (zh) * | 2018-12-18 | 2019-04-12 | 五邑大学 | 油酸苷-7-乙基-11-甲基酯的制备方法 |
CN109620839A (zh) * | 2019-01-10 | 2019-04-16 | 高亮亮 | 特女贞苷作为细胞自噬诱导剂的应用 |
CN110483598A (zh) * | 2019-08-12 | 2019-11-22 | 湖北省农业科学院中药材研究所 | 具有抗氧化活性的环烯醚萜苷类化合物及其制备方法和应用 |
CN111380978A (zh) * | 2020-03-16 | 2020-07-07 | 重庆市食品药品检验检测研究院 | 一种同时测定药物中辅酶nadp和fad含量的方法 |
CN113860999A (zh) * | 2021-10-12 | 2021-12-31 | 东莞职业技术学院 | 一种利用油橄榄叶制备羟基酪醇的方法 |
CN115778965A (zh) * | 2022-10-24 | 2023-03-14 | 长沙学院 | 女贞苷g13在制备抗心肌纤维化药物中的新应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1290559A (zh) * | 1999-10-01 | 2001-04-11 | 森弗莱克斯国际有限公司 | 乒乓球拍 |
CN1304732A (zh) * | 2000-05-15 | 2001-07-25 | 陈纬 | 治疗骨质增生的中成药 |
CN1709290A (zh) * | 2004-06-18 | 2005-12-21 | 刘国仁 | 骨松停胶囊及其制作方法 |
-
2011
- 2011-12-09 CN CN201110408564.5A patent/CN102389440B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1290559A (zh) * | 1999-10-01 | 2001-04-11 | 森弗莱克斯国际有限公司 | 乒乓球拍 |
CN1304732A (zh) * | 2000-05-15 | 2001-07-25 | 陈纬 | 治疗骨质增生的中成药 |
CN1709290A (zh) * | 2004-06-18 | 2005-12-21 | 刘国仁 | 骨松停胶囊及其制作方法 |
Non-Patent Citations (1)
Title |
---|
邱蓉丽: "中药女贞子化学与药理研究进展", 《中药材》, vol. 30, no. 7, 31 July 2007 (2007-07-31), pages 892 * |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105330710B (zh) * | 2015-10-23 | 2018-03-16 | 大连医科大学 | 一种从女贞子中同时提取三种环烯醚萜苷类化学对照品的方法 |
CN105330710A (zh) * | 2015-10-23 | 2016-02-17 | 大连医科大学 | 一种从女贞子中同时提取三种环烯醚萜苷类化学对照品的方法 |
CN106466325A (zh) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | 一种预防或治疗糖尿病的药物、组合物及其制剂 |
CN106466325B (zh) * | 2016-09-30 | 2019-02-22 | 郑州大学第一附属医院 | 一种预防或治疗糖尿病的药物、组合物及其制剂 |
CN106632544B (zh) * | 2016-12-21 | 2019-12-20 | 上海诗丹德标准技术服务有限公司 | 一种特女贞苷对照品的制备方法 |
CN106632544A (zh) * | 2016-12-21 | 2017-05-10 | 上海诗丹德标准技术服务有限公司 | 一种特女贞苷对照品的制备方法 |
CN106728679A (zh) * | 2016-12-30 | 2017-05-31 | 福建中医药大学 | 一种用于抗骨量丢失的分子中药缓释片及其制备方法 |
CN108823158A (zh) * | 2018-07-05 | 2018-11-16 | 浙江大学 | 女贞苷和特女贞苷在促进体外培养骨髓间充质干细胞增殖和抑制复制性衰老中的应用 |
CN108823158B (zh) * | 2018-07-05 | 2020-08-11 | 浙江大学 | 女贞苷和特女贞苷在促进体外培养骨髓间充质干细胞增殖和抑制复制性衰老中的应用 |
CN109265467A (zh) * | 2018-11-07 | 2019-01-25 | 扬州工业职业技术学院 | 一种中药女贞子来源的七环内酯化合物及其作为抗老年痴呆药物的应用 |
CN109608510A (zh) * | 2018-12-18 | 2019-04-12 | 五邑大学 | 油酸苷-7-乙基-11-甲基酯的制备方法 |
CN109608510B (zh) * | 2018-12-18 | 2021-09-03 | 五邑大学 | 油酸苷-7-乙基-11-甲基酯的制备方法 |
CN109620839A (zh) * | 2019-01-10 | 2019-04-16 | 高亮亮 | 特女贞苷作为细胞自噬诱导剂的应用 |
CN110483598A (zh) * | 2019-08-12 | 2019-11-22 | 湖北省农业科学院中药材研究所 | 具有抗氧化活性的环烯醚萜苷类化合物及其制备方法和应用 |
CN111380978A (zh) * | 2020-03-16 | 2020-07-07 | 重庆市食品药品检验检测研究院 | 一种同时测定药物中辅酶nadp和fad含量的方法 |
CN111380978B (zh) * | 2020-03-16 | 2022-06-07 | 重庆市食品药品检验检测研究院 | 一种同时测定药物中辅酶nadp和fad含量的方法 |
CN113860999A (zh) * | 2021-10-12 | 2021-12-31 | 东莞职业技术学院 | 一种利用油橄榄叶制备羟基酪醇的方法 |
CN115778965A (zh) * | 2022-10-24 | 2023-03-14 | 长沙学院 | 女贞苷g13在制备抗心肌纤维化药物中的新应用 |
CN115778965B (zh) * | 2022-10-24 | 2024-02-23 | 长沙学院 | 女贞苷g13在制备抗心肌纤维化药物中的新应用 |
Also Published As
Publication number | Publication date |
---|---|
CN102389440B (zh) | 2014-08-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102389440B (zh) | 环烯醚萜类化合物在制备抗骨质疏松药物中的应用 | |
Lee et al. | Stimulation of osteoblastic differentiation and mineralization in MC3T3-E1 cells by antler and fermented antler using Cordyceps militaris | |
CN102652792A (zh) | 包含大蒜油、大蒜总多糖和大蒜总皂苷的组合物的抗癌用途 | |
CN105566317A (zh) | 一种化合物及其制备方法 | |
CN105566353A (zh) | 一种化合物及其制备方法 | |
CN103304635B (zh) | 一种环肽类化合物抗肿瘤的应用及其制备方法 | |
CN103222988A (zh) | 一种美洲大蠊提取物及其制备方法和应用 | |
CN102552644A (zh) | 大蒜总多糖的抗癌用途、制备方法及组合物 | |
CN101654485B (zh) | 一种用于治疗恶性肿瘤的白花蛇舌草多糖及其制备方法 | |
CN102824400B (zh) | 包含杜仲和续断的组合物及其治疗骨质疏松症的用途 | |
CN106008446A (zh) | 呫吨酮衍生物及呫吨酮和其衍生物的制备方法与用途 | |
CN100475762C (zh) | 一种贯叶金丝桃中金丝桃素提取物的提取方法 | |
CN106565444B (zh) | 山药地上部分菲类化合物的提取方法及应用 | |
CN105837592B (zh) | 间苯三酚骈松香烷二萜类化合物及其制备方法和药物用途 | |
CN102311442B (zh) | 具有抗肿瘤活性的螺内酰胺生物碱化合物及其制备方法与应用 | |
CN111544440A (zh) | 地奥司明及组合物在制备抗肥胖的产品方面中的应用 | |
CN104231019B (zh) | 单萜苷类化合物在制备抗补体药物中的用途 | |
CN106177035B (zh) | 具有降血糖、抗癌的月季花有效提取物的制备方法及应用 | |
CN109288902A (zh) | 一种具有强抗氧化活性的酸枣叶总黄酮发酵产物的制备方法及其应用 | |
CN106565811B (zh) | 山药地上部分降血糖有效成分的提取方法及应用 | |
CN103880678A (zh) | 苯甲酸衍生物及其制备与降糖应用 | |
CN106692125A (zh) | 一种含野菊花提取物的抗糖尿病药物 | |
CN107840814B (zh) | 单环二萜化合物cassipourol及其制备方法和在制药中的用途 | |
CN109081842A (zh) | 一种深海真菌来源蒽醌类化合物及其在制备抗过敏药物中的应用 | |
CN103739657B (zh) | 一种油茶皂苷化合物、其制备方法、应用及其制备的抗肿瘤药物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: WEI YUAN Free format text: FORMER OWNER: SICHUAN HAOYUAN BIO-TECHNOLOGY CO., LTD. Effective date: 20150506 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20150506 Address after: 610000, No. 15, No. two, 48 neighborhood, Cao family lane, Chengdu, Sichuan, Jinniu District Patentee after: Wei Yuan Address before: 3, 610000 building, 9 pear flower street, Chengdu, Sichuan, Jinjiang District Patentee before: Sichuan Haoyuan Bio-technology Co.,Ltd. |
|
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140820 Termination date: 20171209 |