CN110343038B - Borojo monomer, Borojo extract, and preparation method and application thereof - Google Patents
Borojo monomer, Borojo extract, and preparation method and application thereof Download PDFInfo
- Publication number
- CN110343038B CN110343038B CN201810842071.4A CN201810842071A CN110343038B CN 110343038 B CN110343038 B CN 110343038B CN 201810842071 A CN201810842071 A CN 201810842071A CN 110343038 B CN110343038 B CN 110343038B
- Authority
- CN
- China
- Prior art keywords
- acid
- extract
- bordeaux
- bordea
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000284 extract Substances 0.000 title claims description 40
- 238000000605 extraction Methods 0.000 title claims description 5
- 244000166075 Borojoa patinoi Species 0.000 title abstract description 8
- 235000003558 Borojoa patinoi Nutrition 0.000 title abstract description 8
- 239000000178 monomer Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 18
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 14
- 239000005643 Pelargonic acid Substances 0.000 claims abstract description 13
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 12
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 238000002156 mixing Methods 0.000 claims description 14
- -1 pelargonic acid compound Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 235000006708 antioxidants Nutrition 0.000 claims description 11
- 238000004440 column chromatography Methods 0.000 claims description 11
- 238000010828 elution Methods 0.000 claims description 11
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 9
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 9
- 241000198058 Borojoa Species 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 6
- 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 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 239000005739 Bordeaux mixture Substances 0.000 claims description 4
- 241001107098 Rubiaceae Species 0.000 claims description 3
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- XMEGXHDYCSUOJC-KXOLBLKYSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-16-ethyl-4,6-dihydroxy-15-(hydroxymethyl)-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[C@@H](O)[C@@H](CC=O)C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@@H]1CO XMEGXHDYCSUOJC-KXOLBLKYSA-N 0.000 claims 6
- XMEGXHDYCSUOJC-UHFFFAOYSA-N Tylonolide Natural products CCC1OC(=O)CC(O)C(C)C(O)C(CC=O)CC(C)C(=O)C=CC(=CC1CO)C XMEGXHDYCSUOJC-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 240000003553 Leptospermum scoparium Species 0.000 claims 1
- 235000016887 Leptospermum scoparium Nutrition 0.000 claims 1
- 230000003712 anti-aging effect Effects 0.000 claims 1
- 235000013305 food Nutrition 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002474 experimental method Methods 0.000 abstract description 9
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 52
- 238000001228 spectrum Methods 0.000 description 27
- 230000003595 spectral effect Effects 0.000 description 26
- 239000000126 substance Substances 0.000 description 19
- 239000000523 sample Substances 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 241000511967 Tylophora Species 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000002835 absorbance Methods 0.000 description 9
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 8
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 7
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 239000002158 endotoxin Substances 0.000 description 6
- 229920006008 lipopolysaccharide Polymers 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
- 229940079877 pyrogallol Drugs 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RFVOCVQXVCOBCE-MHTLYPKNSA-N (1R,5S)-5-(carboxymethyl)cyclopent-2-ene-1,2-dicarboxylic acid Chemical compound C(=O)(O)C[C@@H]1CC=C([C@@H]1C(=O)O)C(=O)O RFVOCVQXVCOBCE-MHTLYPKNSA-N 0.000 description 2
- AYRQUPRKTDTPEN-SQQPMCIGSA-N (1s,4as,7as)-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4,7-dicarboxylic acid Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2C(C(O)=O)=CC[C@@H]2C(C(O)=O)=CO1 AYRQUPRKTDTPEN-SQQPMCIGSA-N 0.000 description 2
- 241001072256 Boraginaceae Species 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000007839 Kleinhovia hospita Species 0.000 description 2
- 229930194936 Tylosin Natural products 0.000 description 2
- 239000004182 Tylosin Substances 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- RMMZNKFBCZUBKP-UHFFFAOYSA-N bicyclo[3.1.0]hex-3-ene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC2CC2(C1)C(O)=O RMMZNKFBCZUBKP-UHFFFAOYSA-N 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000020828 fasting Nutrition 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- AYRQUPRKTDTPEN-UXUPSOTBSA-N ixoside Natural products O=C(O)C=1[C@@H]2[C@H]([C@H](O[C@H]3[C@@H](O)[C@H](O)[C@H](O)[C@@H](CO)O3)OC=1)C(C(=O)O)=CC2 AYRQUPRKTDTPEN-UXUPSOTBSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000012353 t test Methods 0.000 description 2
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 2
- 229960004059 tylosin Drugs 0.000 description 2
- 235000019375 tylosin Nutrition 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- 239000012224 working solution Substances 0.000 description 2
- 235000020927 12-h fasting Nutrition 0.000 description 1
- 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
- 241000588807 Bordetella Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- RFVOCVQXVCOBCE-CLZZGJSISA-N C(=O)(O)C[C@H]1CC=C([C@@H]1C(=O)O)C(=O)O Chemical compound C(=O)(O)C[C@H]1CC=C([C@@H]1C(=O)O)C(=O)O RFVOCVQXVCOBCE-CLZZGJSISA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- VLCHQFXSBHIBRV-KNNWKXJLSA-N Mussaenosidic acid Natural products O=C(O)C=1[C@@H]2[C@H]([C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@H](O)[C@@H](CO)O3)OC=1)[C@](O)(C)CC2 VLCHQFXSBHIBRV-KNNWKXJLSA-N 0.000 description 1
- YBZUGUWOQLUNKD-PMPSAXMXSA-N Palustrine Chemical compound C1C(=O)NCCCCNCCCN2[C@H]([C@@H](O)CC)CC=C[C@@H]21 YBZUGUWOQLUNKD-PMPSAXMXSA-N 0.000 description 1
- YMALJVLSPODBKM-UHFFFAOYSA-N Palustrine Natural products C1C(=O)NCCCCNCCCN2C(C(O)CC)C=CCC21 YMALJVLSPODBKM-UHFFFAOYSA-N 0.000 description 1
- 241000845082 Panama Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- YSIFYNVXJOGADM-KDYWOABDSA-N Shanzhiside Chemical compound O([C@H]1[C@H]2[C@@H](C(=CO1)C(O)=O)[C@H](O)C[C@@]2(O)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YSIFYNVXJOGADM-KDYWOABDSA-N 0.000 description 1
- PVPIPGMAEAJMTH-UHFFFAOYSA-N Shanzhiside Natural products OCC1OC(OC2OC=C(C3C(O)CC(O)C23)C(=O)O)C(O)C(O)C1O PVPIPGMAEAJMTH-UHFFFAOYSA-N 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 238000002792 antioxidant assay Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- QKUSRAKPUWQSJS-UHFFFAOYSA-N diazanium 3-ethyl-2H-1,3-benzothiazole-6-sulfonate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)C1=CC=C2N(CC)CSC2=C1.[O-]S(=O)(=O)C1=CC=C2N(CC)CSC2=C1 QKUSRAKPUWQSJS-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229930182489 iridoid glycoside Natural products 0.000 description 1
- 150000008145 iridoid glycosides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 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 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical group [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
Images
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/20—Unsaturated compounds having a carboxyl group bound to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/26—Unsaturated compounds having a carboxyl group bound to a seven-to-twelve-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Botany (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of natural medicinal chemistry, and relates to pelargonic acid 1-pelargonic acid 13 separated from Nanmei fruit pelargonic acid (Borojo) and a preparation method and application thereof. Experiments prove that the compound prepared by the invention has antioxidant, anti-inflammatory and hypoglycemic activities.
Description
Technical Field
The invention belongs to the field of natural medicinal chemistry, and particularly relates to a monomeric compound and an extract in Borax fruit, and a preparation method and application thereof.
Background
Borojoa is the mature fruit of Borojoa patitinous Cuatrec and Borojoa sorbilis Cuatrec, plants of the genus Linguus of the family Rubiaceae. Distributed in the iridescent rainforest of the amazon river basin, native to Columbia, iridescent and Panama. The Bordeaux mixture is rich in fructose and glucose, water-soluble B vitamins, amino acids and proteins, and has great development and utilization values. Local native residents believe that the consumption of the bola fruits can eliminate fatigue, enhance immunity, strengthen yang, improve respiratory inflammation symptoms and resist inflammation. The tylophora has antioxidant (International pharmaceutical research journal, 2013:817-821) and hypoglycemic activities, and the polysaccharide component in the tylophora can enhance immunity, but the anti-inflammatory, antioxidant and hypoglycemic effects of the monomer compound in the tylophora are not reported in the literature at present.
Disclosure of Invention
The invention aims to provide a preparation method and application of a Borojo extract and a monomeric compound thereof.
The purpose of the invention is realized by the following technical scheme:
the Borojo extract and the monomer compound thereof are prepared by the following steps:
(1) suspending Bordeaux powder with water, filtering, and adsorbing the filtrate with macroporous resin, such as AB-8, D101, D102, ZTC-1 or 1300-I type macroporous resin;
(2) eluting with water or ethanol of below 10% to remove impurities, eluting with 20% -80% ethanol water, collecting eluate, and concentrating to dry; the Bordeaux extract is obtained
(3) The Bordetella extract was subjected to silica gel column chromatography (petroleum ether-ethyl acetate gradient elution, 100:0 → 0:100), analyzed by TLC and fractions of similar composition were combined to give 10 major fractions (Fr.1-Fr.10). Fr.4 is subjected to medium-low pressure ODS column chromatography and methanol-water gradient elution (90:10 → 100:0), so as to obtain 7 sub-fractions (Fr.4a-Fr.4g). Wherein Fr.4c, Fr.4d and Fr.4e are respectively subjected to Sephadex LH-20 gel column chromatography, preparative HPLC and recrystallization to obtain compounds of the jewelleric acid-1, the jewelleric acid-2, the jewelleric acid-7 and the jewelleric acid-10. Fr.6 is subjected to medium-low pressure ODS column chromatography, and methanol-water gradient elution (95:5 → 100:0) to obtain 6 sub-fractions (Fr.6a-Fr.6f). The compounds of the musical instrument-8 and the musical instrument-9 are respectively obtained from Fr.6c and Fr.6d through Sephadex LH-20 gel column chromatography and preparative HPLC. Performing medium and low pressure ODS column chromatography on Fr.7, and performing methanol-water gradient elution (95:5 → 100:0) to obtain 8 subflows (Fr.7a-7J). Fr.7d, Fr.7e and Fr.7f are respectively passed through Sephadex LH-20 gel column
The invention discloses a method for analyzing the components of a Borojo extract: the main components of the Boraginaceae extract are identified by structure, and the main components are determined to be 11 new compounds and 2 known iridoid glycosides, and the chemical formula of the Boraginaceae extract is as follows:
the invention also provides the application of the tylophora fruit extract or the monomer in preparing anti-inflammatory or hypoglycemic drugs.
The invention also provides the application of the tylophora fruit extract or the tylophora fruit monomer in preparing the functional food for resisting oxidation/aging or reducing blood sugar.
The invention also provides a pelargonic acid extract of pelargonic, which comprises the following compounds:
the extract further comprises the following compounds:
the invention also provides a tylophora acid extract of tylophora, which comprises the following preparation steps:
taking fresh Bordeaux mixture as raw material, adding water, mixing, pulping or adding water, mixing, filtering, extracting the filtrate with ethyl acetate, mixing ethyl acetate layers, and concentrating under reduced pressure to obtain Bordeaux acid extract.
The Borojoa palustrine is a mature fruit derived from Borojoa patitinoi Cuatrec and Borojoa sorbilis Cuatrec which belong to the genus Rubiaceae.
Drawings
FIG. 1 shows high resolution mass spectrum of Bordeaux acid-1
FIG. 2 NMR spectrum of pelargonic acid-1
FIG. 3 nuclear magnetic resonance carbon spectrum of pelluconic acid-1
FIG. 4 high resolution mass spectrum of Bordeaux acid-2
FIG. 5 nuclear magnetic resonance hydrogen spectrum of pelargonic acid-2
FIG. 6 nuclear magnetic resonance carbon spectrum of pelargonic acid-2
FIG. 7 high resolution mass spectrum of Bordeaux acid-3
FIG. 8 NMR spectrum of pelluconic acid-3
FIG. 9 nuclear magnetic resonance carbon spectrum of pelargonic acid-3
FIG. 10 high resolution mass spectrum of pelluconic acid-4
FIG. 11 NMR spectrum of pelargonic acid-4
FIG. 12 nuclear magnetic resonance carbon spectrum of pelluconic acid-4
FIG. 13 high resolution mass spectrum of pelycolic acid-5
FIG. 14 NMR spectrum of pelargonic acid-5
FIG. 15 nuclear magnetic resonance carbon spectrum of pelargonic acid-5
FIG. 16 high resolution mass spectrum of pelycolic acid-6
FIG. 17 NMR spectrum of pelluconic acid-6
FIG. 18 NMR carbon spectra of pelluconic acid-6
FIG. 19 high resolution mass spectrum of Bordeaux acid-7
FIG. 20 NMR spectrum of pelargonic acid-7
FIG. 21 nuclear magnetic resonance carbon spectrum of pelargonic acid-7
FIG. 22 high resolution mass spectrum of Bordeaux acid-8
FIG. 23 NMR spectrum of pelargonic acid-8
FIG. 24 nuclear magnetic resonance carbon spectrum of pelargonic acid-8
FIG. 25 high resolution mass spectrum of Bordeaux acid-9
FIG. 26 nuclear magnetic resonance hydrogen spectrum of pelargonic acid-9
FIG. 27 NMR carbon spectra of pelargonic acid-9
FIG. 28 high resolution mass spectrum of Bordeaux acid-10
FIG. 29 nuclear magnetic resonance hydrogen spectrum of pelluconic acid-10
FIG. 30 nuclear magnetic resonance carbon spectrum of pelluconic acid-10
FIG. 31 high resolution mass spectrum of Bordeaux acid-11
FIG. 32 NMR spectrum of pelargonic acid-11
FIG. 33 NMR carbon spectra of pelluconic acid-11
FIG. 34 Single Crystal X-ray diffraction Structure of Bordeac acid-1
FIG. 35 Single Crystal X-ray diffraction Structure of Bordeac acid-12
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
EXAMPLE 1 preparation of Bordeaux extract
Taking 50kg of fresh Bordeaux mixture, peeling and mixing seeds, adding 200L of water into pulp, stirring, grinding into pulp, mixing uniformly, and filtering. Adding 100L water into the fruit residue, stirring, grinding into slurry, mixing, and filtering.
The two filtrates were combined, 300L of ethyl acetate was added for extraction, and the ethyl acetate layer was separated. 300L of ethyl acetate was added to the aqueous layer, and the ethyl acetate layer was separated. The aqueous layer was extracted with 300L of ethyl acetate, and the ethyl acetate layer was separated.
And combining the ethyl acetate layers for 3 times, and concentrating under reduced pressure to dryness to obtain 650g of the Bordeaux extract.
EXAMPLE 2 preparation of Bordeaux extract
Adding 50L water into 5kg Bordeaux powder, stirring, mixing, and filtering. Adding 50L water into the filter residue, stirring, mixing, and filtering.
The two filtrates were combined, 100L of ethyl acetate was added for extraction, and the ethyl acetate layer was separated. The aqueous layer was extracted 3 more times with 100L ethyl acetate each time, and the ethyl acetate layer was separated each time.
And combining the ethyl acetate layers for 4 times, and concentrating under reduced pressure to dryness to obtain 480g of the Bordeaux extract.
EXAMPLE 3 Compound preparation and Structure identification
Dissolving 500g of Bordeaux extract in methanol, stirring the mixture with 80-100 meshes of silica gel, performing 200-300-mesh silica gel column chromatography, performing gradient elution with petroleum ether-ethyl acetate at a ratio of 95:5, 90:10, 85:115, 80:20, 75:25, 70:30, 60:40, 50:50 and 0:100 in sequence, detecting by TLC, and combining fractions with similar thin-layer spots to obtain 9 components Fr.1-Fr.9.
Fr.4 is subjected to medium-low pressure ODS column chromatography and methanol-water gradient elution (90:10 → 100:0), so as to obtain 7 sub-fractions (Fr.4a-Fr.4g). Wherein Fr.4c, Fr.4d and Fr.4e are respectively subjected to Sephadex LH-20, Pre-HPLC and recrystallization to obtain compounds of tylophoric acid 1(171mg), tylophoric acid 2(163mg), tylophoric acid 7(201mg) and tylophoric acid 10(167 mg).
Fr.6 is subjected to middle and low pressure ODS column chromatography, and methanol-water gradient elution (95:5 → 100:0) to obtain 6 sub-fractions (Fr.6a-Fr.6f). The compounds of Bordeaux 8(195mg) and Bordeaux 9(218mg) were obtained from Fr.6c and Fr.6d by Sephadex LH-20 and Pre-HPLC, respectively.
Fr.7(2.5g) was subjected to medium-low pressure ODS column chromatography, and eluted with methanol-water gradient (95:5 → 100:0) to give 8 subflows (Fr.7 a-7J). Fr.7d, Fr.7e and Fr.7f were subjected to Sephadex LH-20 and Pre-HPLC respectively to give compounds (146 mg), pelargonic acid 4(160mg), pelargonic acid 5(185mg), pelargonic acid 6(260mg), pelargonic acid 11(136mg), pelargonic acid 12(564mg) and pelargonic acid 13(428 mg).
1((1R,5S) -5-methycylilopent-2-ene-1, 2-dicarboxylic acid) colorless fine needle crystal, and the chemical structure formula is as follows:
the spectral data are as follows: HR-ESI-MS M/z 193.0479[ M + Na ]]+ESI-MS is shown in FIG. 1.1H NMR(CD3OD,400MHz) δ: 1.19(3H, d, J ═ 6.5Hz, H-8), 2.16(1H, ddt, J ═ 18.5,5.5,2.5Hz, H-4a), 2.81(1H, ddt, J ═ 18.5,8.0,2.5Hz, H-4b), 2.57(1H, m, H-1), 3.26(1H, qd, J ═ 5.7,2.0Hz, H-5), 6.83(1H, dd, J ═ 4.5,2.4Hz, H-3), and the nmr hydrogen spectrum is shown in fig. 2.13C NMR(CD3OD,100MHz) δ: 21.4(C-8), 40.1(C-5), 41.7(C-4), 58.8(C-1), 136.4(C-2), 146.4(C-3), 167.9(C-7), 178.2(C-6), and the NMR spectrum is shown in FIG. 3. The absolute configuration of the tylophorbide-1 was determined by single crystal X-ray diffraction method, see fig. 34.
According to the spectral data, the pelycolepent-1 is identified as a new cyclopentene compound and named as (1R,5S) -5-methycyliopennt-2-ene-1, 2-dicarboxylic acid.
Boragic acid-2 ((1S,5S) -5-methycylilopent-2-ene-1, 2-dicarboxylic acid) white amorphous powder, the chemical structural formula is as follows:
the spectral data are as follows: HR-ESI-MS: m/z 193.0479[ M + Na ]]+ESI-MS is shown in FIG. 4.1H NMR(CD3OD,500MHz) δ: 1.10(3H, d, J ═ 7.1Hz, H-8), 2.25(1H, ddt, J ═ 18.0,8.2,2.4Hz, H-4a), 2.65(1H, ddd, J ═ 18.0,8.1,2.8Hz, H-4b), 2.78(1H, dq, J ═ 16.1,7.1Hz, H-5), 3.64(1H, d, J ═ 9.3Hz, H-1), 6.92 (1H, br, H-3), and the nmr hydrogen spectrum is shown in fig. 5.13C NMR(CD3OD,125MHz) δ: 16.6(C-8), 37.1 (C-5), 41.6(C-4), 54.7(C-1), 136.9(C-2), 148.1(C-3), 167.8(C-7), 176.3(C-6), and the NMR spectrum is shown in FIG. 6.
According to the spectral data, the pelycolepent-2 is identified as a new cyclopentene compound and named as (1S,5S) -5-methycyliopennt-2-ene-1, 2-dicarboxylic acid.
The pure-yellow oil of the tylosin-3 ((1R,5R) -5- (carboxymethyl) cyclopent-2-ene-1,2-dicarboxylic acid) has the chemical structural formula:
the spectral data are as follows: HR-ESI-MS: m/z 237.0377[ M + Na ]]+ESI-MS is shown in FIG. 7.1H NMR (CD3OD,400MHz) δ: 2.31(1H, dt, J ═ 13.1,2.3Hz, H-4b), 2.48(1H, dd, J ═ 16.0,8.3Hz, H-8b), 2.61(1H, dd, J ═ 16.0,5.6Hz, H-8a), 2.86(1H, m, H-5), 2.93(1H, dt, J ═ 8.3,2.5Hz, H-4a), 3.44(1H, m, H-1), 6.85(1H, m, H-3), and the nuclear magnetic resonance hydrogen spectrum is shown in fig. 8.13C NMR(CD3OD,100MHz) δ: 39.7(C-4), 40.3(C-8), 41.2(C-5), 56.5(C-1), 136.1(C-2), 146.2(C-3), 167.5(C-7), 175.6(C-9), 177.6(C-6), and the NMR spectrum is shown in FIG. 9.
According to the spectral data, the pelavonic acid-3 is identified as a new cyclopentene compound and named as (3R,4R) -4- (carboxymethyl) cyclopent-1-ene-1,3-dicarboxylic acid.
Bordeaux acid-4 ((1R,5S) -5- (carboxymethyl) cyclopent-2-ene-1,2-dicarboxylic acid) brown amorphous powder with the chemical structural formula:
the spectral data are as follows: HR-ESI-MS: m/z 237.0377[ M + Na ]]+ESI-MS is shown in FIG. 10.1H NMR (CD3OD,400MHz) δ: 2.33(1H, dd, J ═ 18.0,9.4Hz, H-4b), 2.42(1H, dd, J ═ 16.6,8.6Hz, H-8b), 2.57(1H, dd, J ═ 16.6,6.9Hz, H-8a), 2.74(1H, ddd, J ═ 18.0,8.1,2.8Hz, H-4a), 3.05(1H, m, H-5), 3.75(1H, d, J ═ 9.0Hz, H-1), 6.95(1H, br s, H-3), and the nmr hydrogen spectrum is shown in fig. 11.13C NMR(CD3OD,100MHz) δ: 36.7(C-8), 39.0(C-5), 39.5(C-4), 53.5(C-1), 137.5(C-2), 147.5 (C-3), 167.5(C-7), 175.7(C-9), 175.8(C-6), the NMR spectrum is shown in FIG. 12.
According to the spectral data, the pelavonic acid-4 is identified as a new cyclopentene compound and named as (1R,5S) -5- (carboxymethyl) cyclopent-2-ene-1,2-dicarboxylic acid.
5((1R,5R) -5- (2-methoxy-2-oxoethyl) cyclopent-2-ene-1,2-dicarboxylic acid) of tylosin, the chemical structural formula is:
the spectral data are as follows: HR-ESI-MS: m/z 251.0520[ M + Na ]]+ESI-MS is shown in FIG. 13.1H NMR (CD3OD,400MHz)δ:2.31(1H,m,H-4b), 2.50(1H, dd, J ═ 16.0,7.7Hz, H-8b), 2.57(1H, dd, J ═ 16.0,6.0Hz, H-8a), 2.84(1H, m, H-5), 2.86(1H, m, H-4a), 3.48(1H, m, H-1), 3.68(3H, s, H-10), 6.86(1H, br s, H-3), and the nmr spectrum is shown in fig. 14.13C NMR(CD3OD,100MHz) δ: 39.7(C-4), 40.1(C-8), 41.4(C-5), 52.6(C-10), 56.5(C-1), 136.1(C-2), 146.4(C-3), 167.2(C-7), 175.5(C-6), 176.3(C-9), and the NMR spectrum is shown in FIG. 15.
According to the spectral data, the Calycolic acid-5 is identified as a new cyclopentene compound and named as (1R,5R) -5- (2-methoxy-2-oxoethyl) cyclopent-2-ene-1,2-dicarboxylic acid.
1, 6((1S,5R) -5- (2-methoxy-2-oxoethyl) cyclopent-2-ene-1,2-dicarboxylic acid) of tylosin acid, wherein the chemical structural formula is as follows:
the spectral data are as follows: HR-ESI-MS: m/z 251.0520[ M + Na ]]+ESI-MS is shown in FIG. 16.1H NMR (CD3OD,300MHz) δ 2.32(1H, ddt, J ═ 18.0,9.4,2.4Hz, H-4b), 2.54(2H, qd, J ═ 16.6,7.8Hz, H-8), 2.73(1H, ddd, J ═ 18.0,8.1,3.0Hz, H-4a), 3.07(1H, m, H-5), 3.68(3H, s, H-10), 3.74(1H, dd, J ═ 9.3,1.5Hz, H-1), 6.94(1H, br s, H-3), and the nmr hydrogen spectrum is shown in fig. 17.13C NMR(CD3OD,75MHz) δ: 36.6(C-8), 39.0(C-5), 39.3(C-4), 52.1(C-10), 53.5(C-1), 137.3(C-2), 147.1(C-3), 167.5(C-7), 174.2(C-9), 175.7(C-6), the NMR spectrum is shown in FIG. 18.
According to the spectral data, the Calycolic acid-6 is identified as a novel cyclopentene compound and is named as (1S,5R) -5- (2-methoxy-2-oxoethyl) cyclopent-2-ene-1,2-dicarboxylic acid.
Boragic acid-7 ((1R,5S) -1-methoxybutyryl-5-methoxylocent-2-enecarboxylic acid) yellow oil, the chemical structural formula is as follows:
the spectral data are as follows: HR-ESI-MS: m/z 207.0635[ M + Na ]]+ESI-MS is shown in FIG. 19.1H NMR (CD3OD,500MHz) δ 1.18(3H, d, J ═ 6.0Hz, H-8), 2.16(1H, ddt, J ═ 18.4,5.8,2.3Hz, H-4b), 2.53 (1H, m, H-5), 2.81(1H, ddt, J ═ 18.4,8.2,2.5Hz, H-4), 3.30(1H, m, H-1), 3.68(3H, s, H-9), 6.83(1H, dd, J ═ 4.2,2.4Hz, H-3), and the nmr hydrogen spectrum is shown in fig. 20.13C NMR(CD3OD,125MHz) delta 21.3 (C-8), 40.2(C-5), 41.8(C-4), 52.5(C-9), 53.8(C-1), 136.7(C-2), 146.4(C-3), 168.4(C-7), 176.8(C-6), and NMR C spectra are shown in FIG. 21.
According to the above spectral data, the pelycolic acid-7 is identified as a new cyclopentene compound and named as (1R,5S) -1-methoxycarboxyl-5-methoxycarboxyl-2-enecarboxylic acid.
1, 8(tans-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta [ b ] furan-5-carboxylic acid) light yellow amorphous powder with the chemical structural formula:
the spectral data are as follows: HR-ESI-MS: m/z 191.0316[ M + Na ]]+ESI-MS is shown in FIG. 22.1H NMR(CD3OD,500MHz) δ:2.56(1H, ddt, J ═ 19.0,4.0,2.5Hz, H-4 '), 2.95(1H, dddd, J ═ 19.0,9.0,2.5,1.5Hz, H-4 "), 3.47 (1H, m, H-3a), 3.95(1H, ddd, J ═ 9.0,4.2,1.8Hz, H-6a), 4.05(1H, dd, J ═ 9.5,5.0Hz, H-3'), 4.56(1H, dd, J ═ 9.5,8.0Hz, H-3"), 6.83(1H, dd, J ═ 4.5,2.4Hz, H-6), and the nmr spectrum is shown in fig. 23.13C NMR(CD3OD,125MHz) delta 39.8(C-4), 40.2(C-3a), 51.4(C-6a), 74.7(C-3), 134.6(C-5), 146.2(C-6), 166.7(C-7), 178.1(C-1), and NMR C spectra are shown in FIG. 24.
According to the above spectral data, the bolaconic acid-8 is identified as a novel fused ring compound and named as tan-2-oxo-3, 3a,4,6a-tetrahydro-2H-cyclopenta [ b ] furan-5-carboxylic acid.
Boragic acid-9 (cis-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta [ b ] furan-5-carboxylic acid) yellow oil with the chemical structural formula:
the spectral data are as follows: HR-ESI-MS: m/z 191.0318[ M + Na ]]+ESI-MS is shown in FIG. 25.1H NMR(CD3OD,500MHz) δ: 2.43(1H, dd, J ═ 18.5,4.2Hz, H-3'), 2.49(1H, m, H-4), 2.96(1H, dd, J ═ 18.5,10.5Hz, H-3 ″), 3.31(1H, m, H-3a), 2.97(1H, ddd, J ═ 19.6,8.8,2.4Hz, H-4), 5.69(1H, dd, J ═ 7.5,2.1Hz, H-6a), 7.10(1H, t, J ═ 2.4Hz, H-5), and the nmr hydrogen spectrum is shown in fig. 26.13C NMR(CD3OD,125MHz) δ: 36.3(C-3), 37.1(C-3a), 40.5(C-4), 89.2(C-6a), 136.3(C-6), 151.0(C-5), 166.6(C-7), 179.6(C-2), NMR spectrum is shown in FIG. 27.
According to the above spectral data, pelycolic acid-9 was identified as a novel fused ring compound and named as cis-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta [ b ] furan-5-carboxylic acid.
Pellitorin-10 (cis-3,3a,4,6a-tetrahydro-2H-cyclopenta [ b ] furan-6-carboxylic acid) yellow amorphous powder with the chemical structural formula:
the spectral data are as follows: HR-ESI-MS with M/z 177.0529[ M + Na ]]+ESI-MS is shown in FIG. 28.1H NMR(CD3OD,500MHz) δ:1.68(1H, m, H-3 '), 2.07(1H, m, H-3 "), 2.81(1H, ddd, J ═ 19.6,8.8,2.2Hz, H-4 '), 2.32(1H, m, H-4), 3.05(1H, m, H-3a), 3.56(1H, m, H-2 '), 3.81(1H, m, H-2"), 5.22(1H, d, J ═ 6.0Hz, H-6a), 6.87(1H, t, J ═ 2.4Hz, H-5), and the nmr hydrogen spectrum is shown in fig. 29.13C NMR(CD3OD,125MHz)δ:35.7(C-3),40.1(C-4), 41.3(C-3a),67.1(C-2),88.0(C-6a),1372(C-6), 148.1(C-5), 168.3(C-7), NMR spectrum is shown in FIG. 30.
According to the spectral data, the pelavonic acid-10 is identified as a novel fused ring compound and is named as cis-3,3a,4,6 a-tetrahydroo-2H-cyclopenta [ b ] furan-6-carboxylic acid.
Boragic acid-11 (bicyclo [3.1.0] hex-3-ene-1,3-dicarboxylic acid) yellow oil with the chemical structural formula:
the spectral data are as follows: m/z 191.0316[ M + Na ]]+ESI-MS is shown in FIG. 31.1H NMR(CD3OD,500MHz) δ 0.67(1H, t, J ═ 5.0Hz, H-6 '), 1.84(1H, dd, J ═ 8.5,4.2Hz, H-6 "), 2.19(1H, m, H-5), 2.50(1H, dd, J ═ 19.7, 2.0Hz, H-2'), 2.84(1H, ddd, J ═ 19.7,7.0,2.0Hz, H-2"), 6.43(1H, m, H-4), and the nmr hydrogen spectrum is shown in fig. 32.13C NMR(CD3OD,125MHz) delta 24.1(C-6), 29.7(C-5), 35.9(C-2), 37.4(C-1), 140.1(C-3), 143.1(C-4), 167.4(C-8), 175.7(C-7), and the NMR spectrum is shown in FIG. 33.
The above spectral data are consistent with those reported in the literature (Prinzbach H, et al. Chemische Berichte,1965,98(7):2201-2220), and thus, Bordeac acid-11 was identified as a bicyclo [3.1.0] hex-3-ene-1,3-dicarboxylic acid.
Boracoic acid-12 (ixoside) light yellow needle crystal, the chemical structural formula is:
the spectral data are as follows: HR-ESI-MSm/z 411.0903[ M + Na ]]+。1H NMR(CD3OD,300MHz)δ:2.45 (1H,br d,J=18.6Hz,H-6b),2.95(1H,dd,J=18.6,8.1Hz,H-6a),3.22(2H,m,H-5,H-9),5.67(1H,d, J=5.1Hz,H-1),6.93(1H,m,H-7),7.51(1H,s,H-3),3.22(1H,m,H-2′),3.34(1H,m,H-4′),3.36 (1H,m,H-5′),3.37(1H,m,H-3′),3.71(1H,m,H-6′),3.87(1H, d, J ═ 11.4Hz, H-6 ') and 4.65 (1H, d, J ═ 7.8Hz, H-1').13C NMR(CD3OD,75MHz) δ 35.0(C-5), 40.1(C-6), 47.2(C-9), 96.3(C-1), 112.4(C-4), 136.1(C-8), 147.8(C-7), 153.6(C-3), 168.1(C-10), 170.5(C-11), 62.5(C-6 '), 71.2 (C-4'), 74.4(C-2 '), 77.6 (C-5'), 78.0(C-3 '), and 100.2 (C-1'). The absolute configuration of pelluconic acid-12 was determined by single crystal X-ray diffraction and is shown in figure 35.
The above spectral data are consistent with those reported in the literature (Yoshio T, et al, chemical Pharmaceutical Bulletin,1976,24(6): 1216-1218), and thus, Bordetemic acid-12 was identified as ixoside.
Bordeaux acid-13 yellow oily substance, the chemical structural formula is:
the spectral data are as follows: HR-ESI-MS: m/z 415.1218[ M + Na ]]+。1H NMR(CD3OD,400MHz) δ:1.28 (1H, s, H-10), 1.85(1H, dd, J ═ 13.2,6.0Hz, H-7a), 2.05(1H, dd, J ═ 13.2,6.8Hz, H-7b), 2.62(1H, dd, J ═ 10.0,2.4Hz, H-9), 2.97(1H, dd, J ═ 10.0,3.2Hz, H-5), 5.57(1H, d, J ═ 2.4Hz, H-1), 7.42(1H, s, H-3), 3.19(1H, m, H-2 '), 3.27(1H, m, H-4 '), 3.33(1H, m, H-5 '), 3.38(1H, m, H-3.65 (1H, 3.65, H-2 '), 3.6H-6H ', 6, d, 6H-6, d, J ═ 2,6, H-1, 6, d, j ═ 8.0Hz, H-1').13C NMR(CD3OD,100MHz) Δ 24.8(C-10), 41.4(C-5), 49.1(C-7), 51.4(C-9), 77.7(C-6), 79.0(C-8), 94.8(C-1), 111.6(C-4), 152.6(C-3), 171.3(C-11), 62.9(C-6 '), 71.7 (C-4'), 74.5(C-2 '), 78.0 (C-3'), 78.3(C-5 '), and 99.8 (C-1').
The above spectral data are consistent with those reported in the literature (Masateru O, et al, chemical Pharmaceutical Bulletin,2007,55(4):632-634), so that tylophorbide-13 was identified as shanzhiside.
Example 4 in vitro antioxidant assay
1. Materials and methods
1.1 materials:
a sample to be tested: the extract of tylophora fruits prepared in example 1 was mixed with 13 monomeric compounds, standard antioxidant vitamin C.
Reagent: ABTS (2, 2-diaza-bis (3-ethyl-benzothiazole-6-sulfonic acid) diammonium salt), DPPH (diphenylpicrylhydrazyl) were purchased from Sigma company. Other reagents are domestic analytical purifiers.
1.2 scavenging of free radicals in DPPH
DPPH, a stable nitrogen-centered radical, with strong absorption at 517 nm. When an antioxidant is present in the reaction system, it can be paired with DPPH.single electron to gradually decrease the absorption peak at 517nm, and the absorbance value decreases. Moreover, the degree of this decrease is quantitatively related to the degree of radical scavenging.
Dissolving DPPH0.0246g in about 100mL solvent methanol, ultrasonic treating for 5min, and shaking to make upper and lower parts uniform. Preparing a series of concentrations of sample with methanol, adding 0.1ml sample solution into 2ml DPPH methanol solution, mixing well, and measuring the absorbance at 515nm after 30 min; the absorbance value of the blank was determined by the same method using methanol instead of the sample. Each sample was run in parallel 3 times and the mean was calculated.
DPPH clearance (%) - (a)Blank space-ASample (I))/ABlank space]×100%
IC50: the semi-inhibitory amount, which represents the concentration of the sample required to scavenge 50% of the free radicals or inhibit 50% of the oxidation, is often used to represent the magnitude of antioxidant activity.
1.3 pairs of ABTS+Determination of scavenging Capacity
ABTS generates stable blue-green cationic free radical ABTS after being oxidized by active oxygen+When an antioxidant is added to it, the substance will react with ABTS+The reaction takes place to fade the color of the reaction system, i.e. the absorbance value is reduced, and the degree of the reduction can reflect the antioxidant capacity of the antioxidant.
Mixing 0.4ml of 7.4mmol/L ABTS and 1.43ml of 2.6mmol/L potassium persulfate, reacting at room temperature in the absence of light, and standing overnight to obtain ABTS+Free radical reserveAnd (4) liquid. Preparing the sample with methanol to a series of concentrations, adding 0.8ml ABTS into 0.2ml sample solution+Uniformly oscillating the free radical working solution for 10s, carrying out water bath reaction at 30 ℃ for 10min, and measuring the absorbance value of the free radical working solution at 734 nm; the absorbance value of the blank was determined by the same method using methanol instead of the sample. Each sample was run in parallel 3 times and the mean was calculated.
ABTS clearance (%) - (a)Blank space-ASample (I))/ABlank space]×100%
IC50: the semi-inhibitory amount, which represents the concentration of the sample required to scavenge 50% of the free radicals or inhibit 50% of the oxidation, is often used to represent the magnitude of antioxidant activity.
1.4 scavenging effect on superoxide radical
Utilizes pyrogallol to generate autoxidation chain reaction in alkaline environment and release a large amount of O2-,·O2-Further accelerate the oxidation of pyrogallol to generate a series of intermediate products with characteristic absorption in the visible light region. If the anti-oxidation substance is added into the reaction system, the autoxidation rate of the pyrogallol can be reduced, and the generated O can be removed2-And the generation of intermediate products is inhibited, so that the absorbance of the reaction solution at 320nm is reduced, and the reduction degree can reflect the antioxidant capacity of the antioxidant.
Preparing a sample into a series of concentrations by using methanol, adding 0.2ml of sample solution into 4ml of sample solution with a certain concentration and 4.5ml of 0.1mol/L Tris-HCl buffer solution (pH 8.2), adding 0.2ml of 3mmol/L pyrogallol solution after 20min of water bath at 25 ℃, uniformly mixing, reacting for 5min in the water bath at 25 ℃, adding 1mol/LHCl to terminate the reaction, and measuring the absorbance at 325 nm; the absorbance value of the blank was determined by the same method using distilled water instead of the sample.
Clearance (%) [ (a blank-a sample)/a blank ] × 100%
IC50: the semi-inhibitory amount, which represents the concentration of the sample required to scavenge 50% of the free radicals or inhibit 50% of the oxidation, is often used to represent the magnitude of antioxidant activity.
2. Statistical treatment
3. Results
Using IC50The antioxidant activity of the tylophora extract and the 13 monomeric compounds was evaluated. The antioxidant results are shown in the table below.
TABLE 1 antioxidant Activity of Bordeaux extracts and monomeric Compounds thereof
As can be seen from the above table, compared with vitamin C, the monomeric compounds all showed good antioxidant activity, and the activity was better than that of the bola extract.
Example 5 anti-inflammatory assay
Sample preparation: bordeaux extract and 13 monomeric compounds prepared in examples 1 and 3
1. Experimental methods
Lipopolysaccharide (LPS) is utilized to stimulate RAW264.7 cells, an in vitro inflammation model is established, the influence of the Bordeaux extract and 14 monomer compounds on the production of an inflammatory factor TNF-alpha is discussed, and the specific operation is as follows:
(1) cell culture: RAW264.7 cells were cultured in DMEM medium containing 10% fetal calf serum, penicillin 100U/mL and streptomycin 100U/mL at 37 ℃ with 5% CO2Subculturing under the condition. And (4) carrying out passage after the cells grow to 70-80% of fusion, wherein the liquid is changed once in 1-2 days, and the passage is carried out once in 4-6 days.
(2) 1X 10 of RAW264.7 cell suspension5Inoculating 100 μ L/well of the suspension in a 96-well plate at 37 deg.C under 5% CO2Culturing for 12h in an incubator, adding samples to be detected with different concentrations, inoculating 4 holes of each concentration sample in parallel, placing at 37 ℃ for continuous culture for 24h, adding 100ng/mL LPS, continuing to culture for 9h, taking 200 mu l of supernatant from each hole, and detecting the content of TNF-alpha according to the operation method of the TNF-alpha ELISA kit. Meanwhile, an LPS control group was established.
2. Statistical treatment
Results of the experiment toThe comparison among groups adopts t test, and the difference represented by P < 0.05 has statistical significance.
3. Results
The results are shown in the following table.
TABLE 2 inhibition of TNF-alpha inflammatory factor production in RAW264.7 cells by LPS using Bordeaux extract and monomeric compounds thereof
Compared with the group in which LPS alone acted,**P<0.01;***P<0.001。
as can be seen from the above table, the monomeric compounds all showed good anti-inflammatory activity compared to the tylophora extract.
Example 6 hypoglycemic experiments
Sample preparation: bordeaux extract and 13 monomeric compounds prepared in examples 1 and 3
1. Experimental methods
170 ICR male mice (6 weeks old, 30-35 g in weight) were randomly divided into 10 normal control groups and 160 diabetes model groups, the normal groups were given basal diet, and the model groups were given high-fat diet. Feeding for 4 weeks, fasting for 12h, injecting streptozotocin into abdominal cavity at a dose of 100mg/kg (solvent is citric acid-sodium citrate buffer solution, pH is 4.5), measuring glucose tolerance of mice for 2h after 3 days, and screening mice with blood sugar value of more than 11.1mmol/mL as mice successfully modeled. The mice that were modelled were randomly divided into 1 model group and 14 experimental groups. The experimental group was orally administered at 2mg/kg by gavage 1 time daily for 2 weeks. After the experiment is finished, fasting blood glucose value and fasting body weight of the mice fasted overnight are detected.
2. Statistical treatment
Results of the experiment toThe comparison among groups adopts t test, and the difference represented by P < 0.05 has statistical significance.
3. Results
The results of the experiment are shown in the following table:
TABLE 3 hypoglycemic action of Bordeaux extract and monomeric compound
In comparison with the normal group,##P<0.01;###P<0.001; in comparison to the set of models,*P<0.05;**P<0.01;**P<0.001。
as can be seen from the above table, the monomeric compounds all showed good hypoglycemic activity compared to the tylophora extract.
The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments, and any other changes, modifications, substitutions and simplifications which do not depart from the spirit and principle of the present invention should be regarded as equivalent replacements within the protection scope of the present invention.
Claims (8)
4. the method for preparing a pelargonic acid compound according to claim 1, wherein: the preparation method comprises the following preparation steps:
taking fresh Bora edulis as a raw material, adding water, uniformly mixing, grinding into slurry or adding water, uniformly mixing Bora edulis freeze-dried powder, filtering, adding ethyl acetate into filtrate for extraction, combining ethyl acetate layers, and concentrating under reduced pressure to obtain Bora edulis extract;
adding methanol into the Leptospermum scoparium extract for redissolving, mixing the sample with silica gel, performing silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate of 95:5, 90:10, 85:115, 80:20, 75:25, 70:30, 60:40, 50:50 and 0:100 in sequence to obtain 9 components Fr.1-Fr.9;
fr.4 is subjected to medium and low pressure ODS column chromatography and methanol-water gradient elution to obtain 7 sub-fractions Fr.4a-Fr.4g, wherein Fr.4c, Fr.4d and Fr.4e are subjected to Sephadex LH-20, Pre-HPLC and recrystallization respectively to obtain compounds of tylonolide 1, tylonolide 2, tylonolide 7 and tylonolide 10;
fr.6 is subjected to middle and low pressure ODS column chromatography and methanol-water gradient elution to obtain 6 sub-fractions Fr.6a-Fr.6f, Fr.6c and Fr.6d which are respectively subjected to Sephadex LH-20 and Pre-HPLC to obtain compounds of tylophoric acid 8 and tylophoric acid 9;
performing medium-low pressure ODS column chromatography on Fr.7, performing methanol-water gradient elution to obtain 10 sub-fractions Fr.7a-7 j, and performing Sephadex LH-20 and Pre-HPLC on Fr.7d, Fr.7e and Fr.7f to obtain compounds (including Bordea acid 3, Bordea acid 4, Bordea acid 5, Bordea acid 6, Bordea acid 11, Bordea acid 12 and Bordea acid 13); wherein: the structure of the fruit acid is Baoleguo acid 11
5. The method for producing the pelargonic acid extract as claimed in claim 4, wherein the pelargonic acid is a mature fruit derived from Borojoa patitinous Cuatrec and Borojoa sorbilis Cuatrec, plants belonging to the genus Lingo of the family Rubiaceae.
6. Use of the tylophoronic acid compound according to claim 1 or the tylophoronic acid extract according to any one of claims 2 to 3 for the preparation of a food or health product for anti-oxidant/anti-ageing treatment.
7. Use of the tylophoronic acid compound according to claim 1 or the tylophoronic acid extract according to any one of claims 2 to 3 for the preparation of a therapeutic anti-inflammatory medicament.
8. Use of the tylonolide acid compound according to claim 1 or the tylonolide acid extract according to any one of claims 2 to 3 in the preparation of a medicament for lowering blood glucose or a health product for assisting in lowering blood glucose.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2018102873513 | 2018-04-02 | ||
CN201810287351 | 2018-04-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110343038A CN110343038A (en) | 2019-10-18 |
CN110343038B true CN110343038B (en) | 2022-03-15 |
Family
ID=68173348
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810842071.4A Active CN110343038B (en) | 2018-04-02 | 2018-07-26 | Borojo monomer, Borojo extract, and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110343038B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112316013A (en) * | 2020-10-21 | 2021-02-05 | 暨南大学 | Composition containing guava and tylophora fruits and application thereof |
CN112316028A (en) * | 2020-10-21 | 2021-02-05 | 暨南大学 | Composition containing Bordeaux mixture and mulberry leaves and application thereof |
CN112362777A (en) * | 2020-11-03 | 2021-02-12 | 广州博罗霍生物科技有限公司 | Microanalysis method of symbolic component Borojo-8, 9-iridoid glycoside in Borojo and products thereof |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1073161A (en) * | 1991-11-05 | 1993-06-16 | 史密丝克莱恩比彻姆公司 | ET (ENDOTHELIN) receptor antagonist |
WO2002087322A3 (en) * | 2001-04-27 | 2002-12-19 | Syngenta Participations Ag | Herbicidal composition |
CN102151282A (en) * | 2011-03-01 | 2011-08-17 | 贾正平 | Application of iridoid glycoside and derivatives thereof as plasmin inhibitor and medicine composites of plasmin inhibitor |
CN102351927A (en) * | 2011-08-17 | 2012-02-15 | 梁公壁 | Borojo active extract and preparation method and antibacterial and anti-oxidation application thereof |
CN104721180A (en) * | 2015-02-07 | 2015-06-24 | 中国科学院昆明植物研究所 | Application of valeriana jatamansi Jones part in preparation of N-type calcium channel inhibitor |
CN105125573A (en) * | 2015-07-29 | 2015-12-09 | 刘博� | Application of Borojo polysaccharides to enhancement of immunity of human bodies and animal bodies |
CN105747224A (en) * | 2016-03-23 | 2016-07-13 | 焦红 | Application of Borojoa sorbilis Cuatrec to assistance in blood glucose reduction |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8303995B1 (en) * | 2008-06-13 | 2012-11-06 | Board Of Regents, The University Of Texas System | Nitrite formulations and their use as nitric oxide prodrugs |
-
2018
- 2018-07-26 CN CN201810842071.4A patent/CN110343038B/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1073161A (en) * | 1991-11-05 | 1993-06-16 | 史密丝克莱恩比彻姆公司 | ET (ENDOTHELIN) receptor antagonist |
WO2002087322A3 (en) * | 2001-04-27 | 2002-12-19 | Syngenta Participations Ag | Herbicidal composition |
CN102151282A (en) * | 2011-03-01 | 2011-08-17 | 贾正平 | Application of iridoid glycoside and derivatives thereof as plasmin inhibitor and medicine composites of plasmin inhibitor |
CN102351927A (en) * | 2011-08-17 | 2012-02-15 | 梁公壁 | Borojo active extract and preparation method and antibacterial and anti-oxidation application thereof |
CN104721180A (en) * | 2015-02-07 | 2015-06-24 | 中国科学院昆明植物研究所 | Application of valeriana jatamansi Jones part in preparation of N-type calcium channel inhibitor |
CN105125573A (en) * | 2015-07-29 | 2015-12-09 | 刘博� | Application of Borojo polysaccharides to enhancement of immunity of human bodies and animal bodies |
CN105747224A (en) * | 2016-03-23 | 2016-07-13 | 焦红 | Application of Borojoa sorbilis Cuatrec to assistance in blood glucose reduction |
Non-Patent Citations (4)
Title |
---|
Ohio,《REGISTRY》;Columbus;《REGISTRY》;20010913;1331836-11-3 * |
Photoisomerisierung des Cyclohexadien-(l.3)-dicarbonsaure-( 1.4)-dimethylesters zu Bicyclo[3.1 .O]hexen-Derivaten;Prinzbach H et al.;《Chemische Berichte》;19650131;第98卷(第7期);第2201-2220 * |
响应面法优化宝乐果中Ixoside的工艺研究;徐方方等;《中华中医药杂志》;20161231;第31卷(第12期);第5209-5214页 * |
宝乐果体外抗氧化作用;鲁亦乐等;《国际药学研究杂志》;20131231;第40卷(第6期);第817-821页 * |
Also Published As
Publication number | Publication date |
---|---|
CN110343038A (en) | 2019-10-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110343038B (en) | Borojo monomer, Borojo extract, and preparation method and application thereof | |
CN101007017B (en) | Extract of traditional Chinese medicine having alpha-glucosidase inhibitor activity and its application | |
CN106588947B (en) | Isoamylene radical chromocor class compound in jackfruit and its anti-osteoporosis new application | |
CN110498785A (en) | A kind of lycium ruthenicum anthocyanidin and preparation method thereof | |
KR100878331B1 (en) | Composition for anti-obesity effect comprising a vitis vinifera extract or active compound isolated therefrom | |
JP2013010782A (en) | Preparation of fagopyritol and uses therefor | |
Hunyadi et al. | Volatile glycosides from the leaves of Morus alba with a potential contribution to the complex anti-diabetic activity | |
CN106109515A (en) | A kind of extracting method of total Flavonoids from Suaeda salsa | |
JP2000044472A (en) | Medicine for preventing or treating diabetic complication | |
CN115073295A (en) | Unsaturated fatty acid in purslane, and extraction and separation method and application thereof | |
CN104544456B (en) | Sea-buckthorn type solid dietary fiber beverage and preparation method thereof | |
Baek et al. | Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes of Selliguea feei | |
CN111096983A (en) | Phellinus igniarius phenolic extract with hypoglycemic activity and preparation and application thereof | |
AU772384B2 (en) | Vitex agnus castus extract | |
Karadag et al. | α-Glucosidase inhibitory activities, functional properties, and safety of green tea polysaccharides as a potential source of dietary supplement | |
CN112391436A (en) | NMN-rich green soy peptide and preparation method and application thereof | |
CN104490894A (en) | Preparation method of spermacoce latifolia triterpenoids and application of spermacoce latifolia triterpenoid in preparation of glycosidase inhibitor medicine | |
CN113214233A (en) | Method for extracting and purifying mangiferin from mango seeds | |
CN103239462A (en) | Application of jasmine effective components in alpha-glucosidase inhibitor | |
CN101565419A (en) | 7 and 20 dehydro-silybin dialky ether and preparation method and medicine use thereof | |
CN100509803C (en) | Extractive of total benzofuran of benzoin plants, prepn. method and use thereof | |
Reis et al. | Sesquiterpene lactones from Cynara humilis | |
CN104083348A (en) | Applications of four kaurane diterpene compounds in preparation of glycosidase inhibitor medicines | |
CN104083347A (en) | Applications of compound ent-kaur-16-en-19-oic acid in preparation of glycosidase inhibitor medicines | |
CN101627983B (en) | Medicinal composition for inhibiting angiogenesis and application thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |