CN108530500A - A kind of preparation method and applications of cortex albiziae lignan glycosides monomer - Google Patents
A kind of preparation method and applications of cortex albiziae lignan glycosides monomer Download PDFInfo
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- CN108530500A CN108530500A CN201810349951.8A CN201810349951A CN108530500A CN 108530500 A CN108530500 A CN 108530500A CN 201810349951 A CN201810349951 A CN 201810349951A CN 108530500 A CN108530500 A CN 108530500A
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- Prior art keywords
- cortex albiziae
- preparation
- lignan glycosides
- glycosides monomer
- monomer
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- 239000000178 monomer Substances 0.000 title claims abstract description 31
- 229930182470 glycoside Natural products 0.000 title claims abstract description 27
- 229930013686 lignan Natural products 0.000 title claims abstract description 27
- -1 lignan glycosides Chemical class 0.000 title claims abstract description 27
- 235000009408 lignans Nutrition 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 3
- 235000019441 ethanol Nutrition 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 238000004262 preparative liquid chromatography Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 235000013402 health food Nutrition 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 108010039731 Fatty Acid Synthases Proteins 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 7
- 239000000284 extract Substances 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 230000002829 reductive effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 238000002329 infrared spectrum Methods 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 238000005191 phase separation Methods 0.000 abstract description 2
- 229940126680 traditional chinese medicines Drugs 0.000 abstract description 2
- FFDULTAFAQRACT-MWBGVTEFSA-N Eleutheroside E Natural products COc1cc(cc(OC)c1O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]3OC[C@H]4[C@H]3CO[C@@H]4c5cc(OC)c(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)c(OC)c5 FFDULTAFAQRACT-MWBGVTEFSA-N 0.000 abstract 1
- FFDULTAFAQRACT-JSGUJALWSA-N Eleutheroside E Chemical compound COC1=CC([C@@H]2[C@@H]3[C@H]([C@@H](OC3)C=3C=C(OC)C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=C(OC)C=3)CO2)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FFDULTAFAQRACT-JSGUJALWSA-N 0.000 abstract 1
- 102000015303 Fatty Acid Synthases Human genes 0.000 abstract 1
- 239000002021 butanolic extract Substances 0.000 abstract 1
- 238000001819 mass spectrum Methods 0.000 abstract 1
- 102100022089 Acyl-[acyl-carrier-protein] hydrolase Human genes 0.000 description 20
- 230000000694 effects Effects 0.000 description 18
- 239000012071 phase Substances 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- WEKCEGQSIIQPAQ-IRBNZIFYSA-N (+)-syringaresinol beta-D-glucoside Chemical compound COC1=C(O)C(OC)=CC([C@@H]2[C@@H]3[C@@H]([C@H](OC3)C=3C=C(OC)C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=C(OC)C=3)CO2)=C1 WEKCEGQSIIQPAQ-IRBNZIFYSA-N 0.000 description 7
- 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 7
- 238000006243 chemical reaction Methods 0.000 description 5
- MKRWWSNBWNFVDX-UHFFFAOYSA-N eleutheroside E1 Natural products COC1=CC(C(C)=O)=CC=C1OC1C(O)C(O)C(O)C(COC2C(C(O)(CO)CO2)O)O1 MKRWWSNBWNFVDX-UHFFFAOYSA-N 0.000 description 5
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical compound C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 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 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 244000235603 Acacia catechu Species 0.000 description 1
- 240000007185 Albizia julibrissin Species 0.000 description 1
- 235000011468 Albizia julibrissin Nutrition 0.000 description 1
- 235000006226 Areca catechu Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- 241000206601 Carnobacterium mobile 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
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000118681 Iresine herbstii Species 0.000 description 1
- LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- PXKVPZNSQPPOGU-LFCYPEIASA-N acanthoside B Natural products COc1cc(cc(O)c1O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]4OC[C@H]5[C@@H]4CO[C@@H]5c6cc(OC)c(O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)c(OC)c6 PXKVPZNSQPPOGU-LFCYPEIASA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229950005984 cerulenin Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- WEKCEGQSIIQPAQ-UHFFFAOYSA-N eleutheroside E2 Natural products COC1=C(O)C(OC)=CC(C2C3C(C(OC3)C=3C=C(OC)C(OC4C(C(O)C(O)C(CO)O4)O)=C(OC)C=3)CO2)=C1 WEKCEGQSIIQPAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000000703 high-speed centrifugation Methods 0.000 description 1
- 239000004047 hole gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ILVUABTVETXVMV-UHFFFAOYSA-N hydron;bromide;iodide Chemical compound Br.I ILVUABTVETXVMV-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Food Science & Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Botany (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention belongs to technical field of traditional Chinese medicines, more particularly to a kind of preparation method and applications of cortex albiziae lignan glycosides monomer, the present invention extracts separation from Chinese medicine cortex albiziae has fatty acid synthase 1 monomer of eleutheroside E of inhibiting effect, its preparation process is that cortex albiziae is broken into powder, alcohol reflux extraction；Ethyl acetate, water-saturated n-butanol extract successively；Macroreticular resin elutes；Silica gel column chromatography detaches；Half prepares efficient liquid phase separation, is concentrated under reduced pressure, is drying to obtain, its chemical constitution is determined using infrared spectrum, nuclear magnetic resonance technique, mass spectrum, and the method for the present invention is simple and quick, and required solvent is few, and yield is higher, has higher economic value and learning value.
Description
Technical field
The invention belongs to the preparation method of technical field of traditional Chinese medicines more particularly to a kind of cortex albiziae lignan glycosides monomer and its answer
With.
Background technology
Animal tallow acid synthase (Fatty acid synthase, FAS) is that long chain fatty acids way is catalyzed and synthesized in animal body
Key enzyme in diameter is a multi-functional complex enzyme of energetic supersession.Studies have shown that discovered in recent years FAS becomes new weight-reducing
With the dual potential target spot of anticancer.The aliphatic acid synthase inhibitor with high activity, hypotoxicity is developed, for the anti-jig of cancer
There is great meaning.Up to the present the FAS inhibitor monomers reported are also seldom, and the natural products only found earliest is light blue
Rhzomorph (cerulenin) and using cerulenin structure as the ester type catechu in the C75 and green tea that masterplate is chemically synthesized
Plain EGCG and ECG.It is significant that the higher FAS inhibitor of inhibitory activity is found from natural Chinese medicinal herb.
Cortex albiziae is the dry bark of legume silk tree Albizia julibrissin Durazz., and pharmacopeia records it
Have the function of resolving stagnation for tranquilization, activating blood circulation and reducing swelling, can be used for treating confused and worried, melancholy insomnia, lung carbuncle sore swells, the pain of injury caused by falling and tumbling, grind
Study carefully and shows in cortex albiziae containing a variety of chemical compositions such as triterpene, flavones, lignanoid, alkaloid, tannin and polysaccharide.Do not have also at present
The research that the extraction from cortex albiziae inhibits the active monomers of FAS is documented.
Invention content
In order to solve the above technical problems, the object of the present invention is to provide a kind of preparation sides of cortex albiziae lignan glycosides monomer
Method, the present invention carry out activity to cortex albiziae using fatty acid synthase restraining activity method and are oriented to separation, finally carried from 75% ethyl alcohol
Take the monomer for being separated in the n-butanol phase of object and playing inhibiting effect to fatty acid synthase：Lignan compound Eleutheroside
E1, Chinese name eleutheroside E 1 also known as acanthoside B, this method is simple and quick, and required solvent is few, and yield is higher, obtains
Lignan glycosides monomer has significant inhibiting effect to fatty acid synthase activity.
A kind of preparation method of cortex albiziae lignan glycosides monomer, includes the following steps：
Step 1：Cortex albiziae is broken into powder, is extracted, is concentrated to dryness using 75% alcohol reflux, it is multiple with distilled water
It is molten, it then uses ethyl acetate, water-saturated n-butanol fractional extraction, extract liquor to be concentrated under reduced pressure respectively, obtains ethyl acetate phase, positive fourth
Alcohol phase, mother liquor water phase；
Step 2：Cortex albiziae n-butanol phase dry powder is spent into ion water dissolution, is eluted using D101 macroreticular resins, eluent
For ethyl alcohol；
Step 3：Elution fraction separation, purification are obtained into lignan glycosides monomer.
Further, in step 1, the solid-liquid ratio of refluxing extraction is 1g：10mL, reflux temperature are 75 DEG C, and return time is
2~3h.
Further, in step 2, a concentration of the 30%~95% of ethyl alcohol.
Further, in step 2, a concentration of the 30% of ethyl alcohol.
Further, it in step 3, is detached using silica gel column chromatography, eluant, eluent is dichloromethane：Methanol=18：1, silica gel
Grain size is 200-300 mesh.
Further, it in step 3, is purified using semi-preparative liquid chromatography, using C18 chromatographic columns, mobile phase is
0.3% phosphate aqueous solution and methanol, Detection wavelength 254nm.
The present invention proposes a kind of aliphatic acid synthase inhibitor, including the cortex albiziae lignanoid that above-mentioned preparation method obtains
Glycosides monomer.
The present invention proposes the cortex albiziae lignan glycosides monomer that above-mentioned preparation method obtains and prevents and/or treat preparing
Application in the drug of tumour.
The present invention proposes the cortex albiziae lignan glycosides monomer that above-mentioned preparation method obtains and is preparing slimming medicine and guarantor
Application in health food.
The present invention proposes cortex albiziae lignan glycosides monomer that above-mentioned preparation method obtains in preparing function cosmetics
Application.
According to the above aspect of the present invention, the present invention has at least the following advantages：The extraction purification means of traditional lignan glycosides monomer,
Such as solvent extraction, fractional precipitation, recrystallization are always difficult to obtain sterling, compared with conventional method, extraction efficiency of the invention
Height, runic object yield is higher (250g, yield 10.0%), this is just to isolate and purify to provide more sample below；Macroreticular resin
Lignanoid in cortex albiziae and saponins can be separated, play the role of being enriched with lignanoids；Chromatography combines half to prepare
Liquid phase separation purifying lignanoid can obtain preferable separating effect；The extracting method of the present invention is simple and quick, and required solvent is few,
Efficiency of pcr product is higher, is 0.01368 ‰, and obtained lignan glycosides monomer there is significant inhibition to make fatty acid synthase activity
With.
Description of the drawings
Fig. 1 is the semi-preparative liquid chromatography figure of component Fr4 in embodiment 1.
Fig. 2 is the H2 analytic type liquid chromatograms of active component in embodiment 1.
Fig. 3 is the infrared spectrogram of active component H2 in embodiment 1.
Fig. 4 is the mass spectrogram of active component H2 in embodiment 1.
Fig. 5 is the hydrogen spectrogram of active component H2 in embodiment 1.
Fig. 6 is the carbon spectrogram of active component H2 in embodiment 1.
Fig. 7 is that component AJ-B-1, AJ-B-2, AJ-B-3, AJ-B-4, Fr1, Fr2, Fr3, Fr4, Fr5, Fr6 inhibit fat
The analysis chart of acid synthase activity.
Fig. 8 is the analysis chart that active component H1, H2, H3, H4 inhibit fatty acid synthase activity.
Specific implementation mode
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and should not be taken as limiting the scope of the invention.
The person that is not specified actual conditions in embodiment, carries out according to conventional conditions or manufacturer's recommended conditions.Agents useful for same
Or production firm person is not specified in instrument, being can be with conventional products that are commercially available.
Embodiment 1
Lignan glycosides monomer (eleutheroside E 1) isolates and purifies in cortex albiziae
Cortex albiziae medicinal material 2.5kg is broken into powder, at 75% ethyl alcohol, 75 DEG C refluxing extraction twice, solid-liquid ratio 1:10(g/
ML), reflux extracting time 2h.Merge extracting solution twice, be concentrated under reduced pressure, vacuum drying obtains cortex albiziae total extract 250g
(AJ-T), crude product yield is 10%.Total extract distillation water dissolution, then uses ethyl acetate, water-saturated n-butanol respectively
Fractional extraction.Extract liquor is concentrated under reduced pressure, and respectively obtains ethyl acetate phase (124.7g), n-butanol phase AJ-B (52.4g), mother liquid coming
Phase (23.5g).
Cortex albiziae n-butanol phase dry powder 20g is taken, with deionized water dissolving, aqueous solution is eluted by D101 macroporous resin columns,
Successively with the water of 3 times of column volumes, 30% ethyl alcohol, 50% ethyl alcohol, 70% ethyl alcohol, 95% ethanol gradient elution, four components are obtained：
30% ethanol elution component (AJ-B-1), 50% ethanol elution component (AJ-B-2), 70% ethanol elution component (AJ-B-3),
95% ethanol elution component (AJ-B-4).Four components are lived by fatty acid synthase and measure (assay method is shown in embodiment 3), screening
Go out the highest component AJ-B-1 of activity.
By thin-layered chromatography, determine that eluant, eluent is dichloromethane：Methanol=18：1.Selection grain size is 200-300 mesh silicon
Glue detaches, and silica gel dry method loading component AJ-B-1, thin-layered chromatography detects and collects merging component in real time.It is dense with Rotary Evaporators
Contracting, is obtained 6 components：Fr1、Fr2、Fr3、Fr4、Fr5、Fr6.6 components are lived by fatty acid synthase, and measurement (be shown in by assay method
Embodiment 3), filter out the highest component Fr4 of activity.
Fr4 is isolated and purified using semi-preparative liquid chromatography, using C18 chromatographic columns, flow velocity 5mL/min, temperature
It is 23 DEG C.Mobile phase is 0.3% phosphate aqueous solution (A)-methanol (B), Detection wavelength 254nm, eluent gradient elution journey
Sequence：0~15min, 10%-20%B 15~30min, 20%-38%B 65~66min of 30~65min, 38%-80%B,
80-100%B 66~76min, 100%B 76~80min 100-20%B 80~85min, 20%B.It is enriched to 4 changes altogether
Object is closed, is denoted as H1 (32.4min), H2 (34.0), H3 (38.9min), H4 (45.72min) respectively.The quality of collection H2 is altogether
13mg, yield are 0.01368 ‰ (yield is calculated relative to cortex albiziae quality of medicinal material), semi-preparative liquid chromatography collection of illustrative plates such as Fig. 1
Shown, for the analytic type liquid chromatogram of active component H2 as shown in Fig. 2, being calculated according to peak area ratio, purity is up to 97.4%.
Embodiment 2
The Structural Identification of lignan glycosides monomer (eleutheroside E 1) in cortex albiziae
Sample H2 is used Iodide Bromide direct tablet compressing, is detected using Fourier infrared spectrograph through drying after grinding, red in analysis
Outskirt (4000~400cm of wave number-1) variation, record infrared spectrogram (Fig. 3, the infrared spectrum of sample), IR compose result prompt
Contain phenyl ring, carbon-oxygen bond or hydroxyl in compound.
Mass Spectrometry Conditions：Ionic means：ESI+；Capillary voltage：3.5kVolts；Orifice potential：20Volts；Ion source temperature
Degree： 100℃；Desolvation temperature：400℃；Desolvention gas velocity：500lit/hr；Taper hole gas velocity 50lit/hr；Impact energy
Amount：6Volts；Mass range 100-1000m/z；Voltage：1800Volts.Using MassLynx software collections and data are handled,
Know that the relative molecular mass of compound is 580.Generate multiple fragment ion peaks simultaneously.(Fig. 4, the mass spectrogram of sample)
Sample H2 is dissolved in deuterated methanol in nuclear magnetic tube, using totally digitilized nuclear magnetic resonance chemical analyser measure H-NMR,
C-NMR.Its result figure is Fig. 5,6.
In summary pop data determine that sample H2 is (+)-syringaresinol β-D-glucoside, and Chinese is entitled
Eleutheroside E 1, chemical structural formula are：
Embodiment 3
Ultraviolet-visible spectrophotometry detects fatty acid synthase activity
Fatty acid synthase supernatant extraction purification from chicken gizzard obtains, and NADPH has an absorption at 340nm, and its product
NADP is not absorbed at 340nm.So measuring fatty acid synthase activity by microplate reader to measure the changing value of NADPH
Variation.In containing 1mmol/L EDTA, 7 pH, a concentration of 0.1mmol/L kaliumphosphate buffer in carry out, concentration of substrate
For 6 μm of ol/L of acetyl-CoA, malonyl CoA 12 μm of ol/L, NADPH 37.5 μm of ol/L, a concentration of 50ug/mL of sample to be tested,
Total reaction volume is 2mL, and after 37 DEG C of 4~5min of constant temperature water bath, the high speed centrifugation fatty acid synthase supernatant after 50 μ L dilutions is added
Liquid starts enzyme reaction, continuously monitors absorbance from 340nm wavelength from absorption 200uL reaction systems solution in reaction system every time
Variation.
The active unit (U) of animal FAS is defined as the enzyme amount of oxidation 14nmol NADPH per minute, therefore, every milliliter of height
The enzyme activity of speed centrifugation fatty acid synthase supernatant is calculated with following formula：
In formula：V is the volume number 0.0002L for measuring enzyme activity；C is extension rate；106Nmol coefficients are converted to for mmol；
△A340nmFor the absorbance change value under 340nm wavelength；ε is that NADPH is oxidized to NADP+When mM at 340nm wavelength
Extinction coefficient is herein 6.022L/mmol.
Reaction system is added in sample, and FAS is added and starts reaction, and it is A to measure enzyme activity, and blank control enzyme activity is A0, A/A0
For residual activity (R.A).R.A is smaller, and enzyme reaction inhibition level is higher, shows that the inhibition enzyme activity ability of sample is strong.Separation process
Middle each component inhibits enzyme activity ability as shown in Figure 7,8.
Although the present invention has been described by way of example and in terms of the preferred embodiments, it is not limited to the present invention, any to be familiar with this skill
The people of art can do various change and modification, therefore the protection model of the present invention without departing from the spirit and scope of the present invention
Enclosing be subject to what claims were defined.
Claims (10)
1. a kind of preparation method of cortex albiziae lignan glycosides monomer, it is characterised in that：Include the following steps：
Step 1：Cortex albiziae is broken into powder, is extracted using 75% alcohol reflux, is concentrated to dryness, is redissolved with distilled water, so
It uses ethyl acetate, water-saturated n-butanol fractional extraction respectively afterwards, obtains ethyl acetate phase, n-butanol phase, mother liquor water phase；
Step 2：Cortex albiziae n-butanol phase dry powder is spent into ion water dissolution, is eluted using D101 macroreticular resins, eluent is second
Alcohol；
Step 3：Elution fraction separation, purification are obtained into lignan glycosides monomer.
2. the preparation method of cortex albiziae lignan glycosides monomer according to claim 1, it is characterised in that：In step 1, reflux
The solid-liquid ratio of extraction is 1g：10mL, reflux temperature are 75 DEG C, and return time is 2~3h.
3. the preparation method of cortex albiziae lignan glycosides monomer according to claim 1, it is characterised in that：In step 2, ethyl alcohol
A concentration of 30%~95%.
4. the preparation method of cortex albiziae lignan glycosides monomer according to claim 3, it is characterised in that：In step 2, ethyl alcohol
A concentration of 30%.
5. the preparation method of cortex albiziae lignan glycosides monomer according to claim 1, it is characterised in that：In step 3, use
Silica gel column chromatography detaches, and eluant, eluent is dichloromethane：Methanol=18：1, silica gel grain size is 200-300 mesh.
6. the preparation method of cortex albiziae lignan glycosides monomer according to claim 1, it is characterised in that：In step 3, use
Semi-preparative liquid chromatography is purified, and using C18 chromatographic columns, mobile phase is 0.3% phosphate aqueous solution and methanol, and Detection wavelength is
254nm。
7. a kind of aliphatic acid synthase inhibitor, it is characterised in that：It is obtained including claim 1-6 any one of them preparation methods
Cortex albiziae lignan glycosides monomer.
8. the cortex albiziae lignan glycosides monomer that claim 1-6 any one of them preparation methods obtain prepare prevent and/or
Treat the application in the drug of tumour.
9. the cortex albiziae lignan glycosides monomer that claim 1-6 any one of them preparation methods obtain prepare slimming medicine and
Application in health food.
10. the cortex albiziae lignan glycosides monomer that claim 1-6 any one of them preparation methods obtain is preparing function makeup
Application in product.
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