CN108503523A - Compounds isolated from Antrodia camphorata and uses thereof - Google Patents
Compounds isolated from Antrodia camphorata and uses thereof Download PDFInfo
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- CN108503523A CN108503523A CN201710156444.8A CN201710156444A CN108503523A CN 108503523 A CN108503523 A CN 108503523A CN 201710156444 A CN201710156444 A CN 201710156444A CN 108503523 A CN108503523 A CN 108503523A
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- Prior art keywords
- compound
- cancer
- ubiquinone
- antrodia camphorata
- cell
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- 241001486992 Taiwanofungus camphoratus Species 0.000 title abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 6
- 201000007270 liver cancer Diseases 0.000 claims abstract description 5
- 208000014018 liver neoplasm Diseases 0.000 claims abstract description 5
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims abstract description 4
- 230000004614 tumor growth Effects 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract 2
- 241000123370 Antrodia Species 0.000 claims description 9
- 241000207961 Sesamum Species 0.000 claims description 6
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 abstract description 21
- 201000005249 lung adenocarcinoma Diseases 0.000 abstract description 2
- 210000002307 prostate Anatomy 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 201000011510 cancer Diseases 0.000 description 21
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 150000003669 ubiquinones Chemical class 0.000 description 16
- 231100000135 cytotoxicity Toxicity 0.000 description 14
- 230000003013 cytotoxicity Effects 0.000 description 14
- 229940125782 compound 2 Drugs 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- LUSZELLFBWUVBI-IWBJKXSYSA-N (4r,5r,6r)-4-hydroxy-5-[(2e,6e,9e)-11-hydroxy-3,7,11-trimethyldodeca-2,6,9-trienyl]-2,3-dimethoxy-6-methylcyclohex-2-en-1-one Chemical compound COC1=C(OC)C(=O)[C@H](C)[C@@H](C\C=C(/C)CC\C=C(/C)C\C=C\C(C)(C)O)[C@H]1O LUSZELLFBWUVBI-IWBJKXSYSA-N 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 10
- RJXJHEYXZURDJH-UHFFFAOYSA-N 4,7-dimethoxy-5-methyl-1,3-benzodioxole Chemical compound COC1=CC(C)=C(OC)C2=C1OCO2 RJXJHEYXZURDJH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- STXRLTSAXAWSTB-UHFFFAOYSA-N 2,4-dimethoxy-6-methylbenzene-1,3-diol Chemical compound COC1=CC(C)=C(O)C(OC)=C1O STXRLTSAXAWSTB-UHFFFAOYSA-N 0.000 description 6
- ZXIUCXGVUOQMSH-UHFFFAOYSA-N 3-[4-(3-methylbut-2-enoxy)phenyl]-4-(2-methylpropyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(CC(C)C)=C1C1=CC=C(OCC=C(C)C)C=C1 ZXIUCXGVUOQMSH-UHFFFAOYSA-N 0.000 description 6
- LJTSIMVOOOLKOL-KCZVDYSFSA-N antroquinonol Natural products COC1=C(OC)C(=O)[C@H](C)[C@@H](CC=C(/C)CCC=C(/C)CCC=C(C)C)[C@H]1O LJTSIMVOOOLKOL-KCZVDYSFSA-N 0.000 description 6
- LJTSIMVOOOLKOL-FNRDIUJOSA-N antroquinonol Chemical compound COC1=C(OC)C(=O)[C@H](C)[C@@H](C\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H]1O LJTSIMVOOOLKOL-FNRDIUJOSA-N 0.000 description 6
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XXAVUEUAHANHQA-ZXOJLNOSSA-N [(1R,5R,6R)-6-[(2E,6E)-3,7-dimethyl-8-[(2R,4S)-4-methyl-5-oxooxolan-2-yl]octa-2,6-dienyl]-2,3-dimethoxy-5-methyl-4-oxocyclohex-2-en-1-yl] acetate Chemical compound COC1=C(OC)C(=O)[C@H](C)[C@@H](C\C=C(/C)CC\C=C(/C)C[C@H]2C[C@H](C)C(=O)O2)[C@H]1OC(C)=O XXAVUEUAHANHQA-ZXOJLNOSSA-N 0.000 description 5
- YQYBUJYBXOVWQW-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 YQYBUJYBXOVWQW-UHFFFAOYSA-N 0.000 description 5
- 230000001093 anti-cancer Effects 0.000 description 5
- 235000017471 coenzyme Q10 Nutrition 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 5
- 238000011160 research Methods 0.000 description 5
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- 229940035936 ubiquinone Drugs 0.000 description 5
- AMFCFGFZMSQOIU-UHFFFAOYSA-N 4-hydroxycyclohex-2-en-1-one Chemical group OC1CCC(=O)C=C1 AMFCFGFZMSQOIU-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical class COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- LUSZELLFBWUVBI-SFHLNBCPSA-N Antroquinonol B Natural products COC1=C(OC)C(=O)[C@H](C)[C@@H](CC=C(C)CCC=C(C)CC=CC(C)(C)O)[C@H]1O LUSZELLFBWUVBI-SFHLNBCPSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
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- 235000019441 ethanol Nutrition 0.000 description 3
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 2
- 241000282465 Canis Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000001258 Cinchona calisaya Nutrition 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000005387 correlation spectroscopy with 45 degree mixing pulse Methods 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 231100000263 cytotoxicity test Toxicity 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 methoxyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229960000948 quinine Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 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
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- 231100000167 toxic agent Toxicity 0.000 description 2
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- 238000002211 ultraviolet spectrum Methods 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 1
- RGYFLKMPUITCGP-UHFFFAOYSA-N 3-methyl-3h-furan-2-one Chemical compound CC1C=COC1=O RGYFLKMPUITCGP-UHFFFAOYSA-N 0.000 description 1
- LTVNTOIFRCIZBT-UHFFFAOYSA-N 4-hydroxy-2,3-dimethoxy-6-methylcyclohex-2-en-1-one Chemical group OC1C(=C(C(C(C1)C)=O)OC)OC LTVNTOIFRCIZBT-UHFFFAOYSA-N 0.000 description 1
- KJYPJQDAWLIIJG-UHFFFAOYSA-N 5-methoxy-3-methyl-2-(3,7,11-trimethyldodeca-2,6,10-trienyl)cyclohexa-2,5-diene-1,4-dione Chemical compound COC=1C(C(=C(C(C=1)=O)CC=C(CCC=C(CCC=C(C)C)C)C)C)=O KJYPJQDAWLIIJG-UHFFFAOYSA-N 0.000 description 1
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- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 206010021929 Infertility male Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000007466 Male Infertility Diseases 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 208000018737 Parkinson disease Diseases 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
- 241000222341 Polyporaceae Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010609 cell counting kit-8 assay Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
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- 229940125773 compound 10 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 230000002538 fungal effect Effects 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- 238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 201000006727 periodontosis Diseases 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/06—Fungi, e.g. yeasts
- A61K36/07—Basidiomycota, e.g. Cryptococcus
Abstract
The invention discloses a compound separated from antrodia camphorata, which is represented by a formula I: the compound has the application of preparing the medicine for inhibiting the growth of tumors, wherein the tumors are lung adenocarcinoma, liver cancer and prostate cancerOne of them.
Description
Technical field
This creation is about a kind of compound and application thereof of separated from Antrodia sesame, especially with regard to a kind of by the compound
It is used to prepare the purposes for the treatment of cancer drug.
Background technology
Cancer has become now the main cause of death in the world, causes about 82,000,000 people dead altogether in 2012 through counting
It dies.There are many cytotoxic medicaments of tool to be used to treating cancer now, but advanced cancer or cancer cell have been shifted
Patient, survival rate only have the improvement of fraction.Therefore, research natural goods to develop the drug for the treatment of cancer may is that it is another
The feasible road of kind.(the syn.Antrodia in Chang＆Chou is for the previous research of Antrodia camphorata active constituent
camphoratus；Taiwanofungus camphoratus, Polyporaceae), reported ubiquinone analog derivative
(Ubiquinone derivatives) includes：Antrocamol LT1, antrocamol LT2 and antrocamol LT3,
It shows has cytotoxicity (Yen, et for 5 kinds of human cancer cell's strains such as CT26, A549, HepG2, PC3 and DU-145
al.,Fitoterapia,2015).Based on those results of study, show that its cytotoxicity is needed general
There is cyclonene group (cyclohex-2-enone) in the ring structure of quinone.However, only a small number of have cyclonene group
Studies on Ubiquinone Derivatives example, can be used for differentiating the relevance of the structure and cytotoxicity.These results promote this case to invent
People further explores ubiquinone class homologue, and more different groups of ingredients are for the cytotoxic effect of human cancer cell's strain.
Android tonquinol (Antroquinonol) is a kind of ubiquinone analog derivative, is found from antrodia mycelia.Closely
Come researches show that go out its potentiality with treating cancer, male sterility, periodontosis, Parkinson's disease and angiocardiopathy.Peace
Tall and erect tonquinol show for MCF-7 and MDA-MB-231 human breast cancer cells strain, Hep3B and HepG2 Human Lung Cancers cell strain,
DU-145 and LNCaP human prostate cancer cells' strains etc. have cytotoxicity.In certain anticancer drugs for coming from Chinese herbal medicine
In research, the thick extract of alcohol of antrodia mycelia is found, and is had for lung cancer, liver cancer, Prostatic cancer cell lines aobvious
The cytotoxicity of work.
Invention content
Based on above-mentioned prior art and known basis, the thick extract of alcohol is re-started into research, therefrom detaches and identifies
Go out two new ubiquinone analog derivatives, is antrocinnamone and 4-acetylantrocamol LT3 respectively；And other 9
A known compound, including 6 ubiquinone derivatives, 2 phenyl ring derivatives and 1 maleic acid derivatives.
Disclosed herein a kind of novel ubiquinone analog derivatives separated from Antrodia camphorata, and utilize high pressure liquid
The fingerprint characteristic and those ubiquinone that analyzer (HPLC/high performance liquid chromatography) obtains
Cell toxicant of the individual chemical structure of derivative (compound 1~8) for 3 kinds of human cancer cell's strains (A549, HepG2 and PC3)
The relevance of property.
Accordingly, one of present invention purpose is providing a kind of compound of separated from Antrodia sesame, is indicated with Formulas I：
Another object of the present invention is used to prepare in a kind of compound of separated from Antrodia sesame of offer inhibits tumour growth medicine
The purposes of object, the compound are indicated with Formula XII：
Wherein R is H or OMe, which is one of adenocarcinoma of lung, liver cancer and prostate cancer.
Preferably, the R wherein in the compound is H, it is to be indicated with Formulas I：
Preferably, the R wherein in the compound is OMe, it is to be indicated with formula III：
Inhibit the purposes of tumour growth drug via disclosing above compound and its can be used for preparing, thereby future can should
Etc. compounds and application thereof gradually develop into the potential anticancer drug of tool and related medical applications.
Description of the drawings
Fig. 1 shows that Antrodia camphorata extract carries out the fingerprint of HPLC analysis gained and the residence time of compound 1-11.
Specific implementation mode
Materials and methods
1D and 2D NMR, including COSY, HMQC, HMBC and NOESY frequency spectrum, are recorded in Agilent spectrometers, with
400MHz 1H and 100MHz13C is operated.Chemical shift is with every million times (ppm) and coupling constant (J) unit for Hz
It is reported out and.Proton and carbon atom chemical shift are relative to solvent peak (CDCl3,δH 7.24,δC77.0) to as interior
Standard.ESI-MS systems are with measured by JEOL-JMS-700 mass spectrographs, rotation brightness system revolves luminance meter with JASCO DIP 370 and surveyed
.IR spectral series use Perkin-Elmer 983G Shimadzu sub-ray spectrometers with measured by potassium bromide (KBr) disk method,
UV spectral series are with measured by Shimadzu UV-160 spectrometers.The col-umn chromatography genealogy of law uses purification on normal-phase silica gel (Merck；230–
400mesh).HPLC systems are carried out with Shimadzu system (Kyoto, Japan), including two to be coupled with Rheodyne manual
LC-8A preparative solvent deliveries pump, a system controller (SCL-6A), a UV-VIS sensors (SPD- for syringe
10A) and a fraction collector (FCV-100B), computer system (C-R7A) and analysis software are all connected to
(Shimadzu’s LC solution software).System is installed in Cosmosil 5C18-MS-II packed HPLC pipes
Column (A) 250mm × 4.6mm I.D. (5 μm) and tubing string (B) 250mm × 20mm I.D. (5 μm).Analysis mode HPLC systems utilize
(A) tubing string moves phase linear gradient in gradient condition and is carried out 15 minutes from 60%MeOH/40% water to 80%MeOH/20% water, with
And the gradient from 80%MeOH/20% water to 100%MeOH carries out 15-30 minutes under flow velocity 1.0mL/min.UV detects wavelength
For 254nm.Chromatography HPLC systems utilize tubing string (B), and preparative HPLC condition system is identical as analytic type HPLC, in addition to flow velocity
It is set as except 10mL/min.
Fungal material
The drying mycelia of Antrodia camphorata provides for The Orchid Pavilion biotech inc in December, 2012.The fungi be through
National Defense Medical Center professor H.C.Lin confirmation is crossed, deposit number is (NDMCP No.1011201).
Prepare the thick extract of fungi
Dry Antrodia camphorata mycelia 6.0kg is extracted 2 times at room temperature with 95% ethyl alcohol (60L).It is dense that gained merges extract
Contracting obtains brown syrup (LT-E；1305.3g).This extract is soluble in water and with methylene chloride/water (1:1) it is allocated
Extraction obtains the extract (LT-E-D for being dissolved in dichloromethane；553.3g) and it is dissolved in the extract (LT-E-W of water；
773.6g).Extract after drying is stored under 4 DEG C of dark places.
The separation of compound
Extract (the LT-E-D of dichloromethane will be dissolved in；60g) with column chromatography (silica gel is 230-400 sieve pore) and profit
Use CH2Cl2-MeOH(100:0,95:5,90:10,0:100) stage gradient purges with, and merges to obtain four according to TLC sidelights on groups
Main extract.First extract (LT-E-D-1 that column chromatography obtains；23g) in silica gel (20x 4cm) with CH2Cl2And
CH2Cl2-MeOH(80:20) linear gradient purges with six extractions point of generation.Those extractions point are obtained after purification with preparative HPLC
To antrocinnamone (compounds 1；25.3mg), quinone Q3 (compounds 3；118.4mg)、4-
Acetylantroquinonol (compounds 6；10.6mg)、4,7-dimethoxy-5-methyl-1,3-benzodioxole
(compound 9；117.6mg), 2,4-dimethoxy-6-methylbenzene-1,3-diol (compounds 10；9.4mg) and
Antrodin A (compounds 11；21.3mg).Third extraction point (LT-E-D-3；15g) in silica gel (20x 4cm) with CH2Cl2-
MeOH(95:5) seven extractions of generation that purge with divide.Gained extraction point is further purified to obtain 4- using preparative HPLC
Acetylantrocamol LT3 (compounds 2；224.9mg), antrocamol LT3 (compounds 4；153.0mg)、
Antroquinonol (compounds 5；50.9mg), antroquinonol B (compounds 7；65.3mg) and 4-
Acetylantroquinonol B (compounds 8；10.6mg).
Purifying and confirmation
By 95% alcoholic extract (1305.3g, dry) of Antrodia camphorata with dichloromethane (CH2Cl2) and water progress liquid-liquid
Distribution.The extraction point (60g, dry) for dissolving in dichloromethane is chromatographed with silica gel, UV detections is recycled to carry out HPLC points
From.This step can be used for 11 kinds of compounds (compound 1-11).As a result, 2 novel Studies on Ubiquinone Derivatives：
Antrocinnamone (compound 1) and 4-acetylantrocamol LT3 (compound 2), together with other 9 known chemical combination
Object, including 6 known Studies on Ubiquinone Derivatives：Quinone Q3 (compound 3), antrocamol LT3 (compound 4),
Antroquinonol (compound 5), 4-acetylantroquinonol (compound 6), antroquinonol B (compounds
And 4-acetylantroquinonol B (compound 8) 7)；2 benzene ring type compounds：4,7-dimethoxy-5-
Methyl-1,3-benzodioxole (compound 9) and 2,4-dimethoxy-6-methylbenzene-1,3-diol (change
Close object 10)；And 1 maleic acid derivatives：Antrodin A (compound 11), all by its spectrogram and known references and credible
Sample compares and confirms.Its structure has all been disclosed as preceding contained.
HPLC is analyzed and fingerprint
Antrodia camphorata extract (ACE, 5.0mg) is dissolved in methanol (1mL), and with 0.45 μm of membrane filtration to carry out HPLC points
Analysis.By the confirmation of residence time and UV absorption spectrums (254nm), it is determined that compound 1-11.From Antrodia camphorata extract (ACE)
Obtained compound 1-11, residence time are as shown in Figure 1.
The structural formula of compound 1~11 is as follows：
Compound 1：antrocinnamone
Antrocinnamone is yellow oil, molecular formula C23H32O3(HR-ESI-MS).Its atomic mass is
30amu, than quinine Q3 smallers, be shown as quinine Q3 compound 1 de-methoxy.UV and IR spectrum with
Quinone Q3 are similar, show it with ubiquinone methyl.Compound 11H NMR spectras (CDCl3, table 1) and display
With 5 main methyl, 4 methylene, 1 methoxyl group and 4 olefinic protons, it is similar to compound 2, in addition to being short of H-24
(δ 3.96, s, 3H) signal is except quinone Q3.These results show the de-methoxy of the positions C-3, are associated with according to HMBC
Property：H-3 (δ 5.85, s) to C-1 (δ 182.80), C-2 (δ 158.31) and C-5 (δ 138.75)；With H-7 [δ 3.19 (2H, d, J=
6.8Hz)] to C-4 (δ 186.95), C-5 (δ 138.75), C-6 (δ 144.09), C-8 (δ 118.98) and C-9 (δ 137.51).On
It states data and shows that compound 1 should be 5-methoxy-3-methyl-2- (3,7,11-trimethyldodeca-2,6,10-
trienyl)cyclohexa-2,5-diene-1,4-dione。
Antrocinnamone (compound 1), yellow oil [α]D 23+36.7°(c 0.3,MeOH)；UV(MeOH)λ
max(logε):267.2(2.0)nm；ESIMS(positive)m/z 356.5[M+H]+；IR(KBr)νmax:3455,2065,
1644,1441,1224,554cm-1；1H and 13356.2408 (calcd.for of C NMR, (ginseng table 1 and 2) HRESIMS m/z
C23H32O3[M+H]+356.2408)。
Compound 2：4-Acetylantrocamol LT3
4-Acetylantrocamol LT3 (compound 2), [α]D 23+ 114.7 ° (in MeOH), yellow oil.Its point
Minor is C26H40O6, it is to determine from molecular ion peak in m/z 448.3 [M+H]+It is measured by ESI-MS.The UV spectrum of compound 2,
It, which shows, absorbs maximum value in 264.4nm, IR spectrum ((3448,2974,1744,1632,1454,1364,1236,1142,
1012,944,596cm-1) antrocamol LT3 (compound 4) are similar to, show it with ubiquinone base.Compound 21H
NMR spectra shows that 1 aoxidizes methine with 5 main methyl, 4 methylene, 2 methine protons, 2 methoxyl groups,
4 olefinic protons and 1 acetyl group, are similar to compound 2, in addition to H-4 (δ 5.74, d, 1H) signal further in change
Close object 4 low field area outside and an other acetyl group (δ 2.08, s, 3H).This result shows that the acetyl group is connected to
The positions C-4 of antrocamol LT3.This is partially proved through COSY-45 spectrum, shows oxidation methene proton
(δ 5.74, d, J=3.2Hz, H-4) and oxidation methylene are based on the couple graphics of δ 1.88 (1H, m, H-5).Aforesaid data implies
Compound 2 is 4-acetylantrocamol LT3.The configuration of C-8 and C-12 is E form, such as the δ of C-20 and C-21CPoint
Not in δCShown in 16.02 and 16.08, and relative to those Z configurations about in δC=25.0.The opposite group of the ring of compound 2
State is consistent with antroquinonol and is confirmed via NOESY spectrum.
4-acetylantrocamol LT3 (compound 2)：Yellow oil [α]D 23+114.7°(c 0.3,MeOH)；UV
(MeOH)λmax(logε):264.4(0.7)nm；ESIMS(positive)m/z 448.3[M+H]+；IR(KBr)νmax:
3448,2974,1744,1632,1454,1364,1236,1142,1012,944,596cm-1；1H and 13C NMR, (ginseng table 1
And 2) (calcd.for C of HRESIMS m/z 48.280323H32O3[M+H]+448.2803)。
Compound 3：quinone Q3
Compound 4：antrocamol LT3
Compound 5：antroquinonol
Compound 6：4-acetylantroquinonol
Compound 7：antroquinonol B
Compound 8：4-acetylantroquinonol B
Compound 9：4,7-dimethoxy-5-methyl-1,3-benzodioxole
Compound 10：2,4-dimethoxy-6-methylbenzene-1,3-diol
Compound 11：antrodin A
Table 11H NMR spectra data (CDCl3) compound 1-4
A acetate bases：δ 2.08 (s, OC=OCH3)
Table 213C NMR spectra data (CDCl3) compound 1-4
A) repeatability system derives from DEPT and tests.
B) the signal system without repeatability is to overlap；A small number of chemical shift systems are dispensed from COSY-45 or HMQC spectrum.
C) acetate base：δ 169.77 (s, C=O), 20.94 (q, CH3)
Cell strain and culture
Three human cancer cell's strain (A549 human lung adenocarcinoma cell's strains；HepG2 human hepatocarcinoma cells' strains；PC3 mankind forefront
Adenocarcinoma cell strain) and MDCK (Madin-Darby canine kidney normal cell line) canine kidney cells strain take
From U.S. ATCC.Cancer cell line is to contain 10%FBS, 100IU/mL penicillin, 100 μ g/mL streptomycin
F12 culture mediums are cultivated.Cell culture is under 37 DEG C, the humidity of 5% carbon dioxide.It can be with before each experiment starts
Mycoplasma is infected and is tested with PCR screening methods.
Cytotoxicity test
Three-type-person's quasi-cancer cell strain (A549, HepG2 and PC3) and mdck cell, with Antrodia camphorata extract, secondary extract with
And single compound treated under various concentration survival rate, it is tested and is assessed with cell counting kit-8.Letter
Yan Zhi, with total 5x 103Cells/well (A549, HepG2, PC3 and mdck cell) culture in 96 porose disc 12 hours, by cell with
(0.01-100 μm, double dilutive method) of the compound of various concentration is handled 24 hours.Former culture medium is removed, 10% cell
Each hole is added in counting kit-8, and culture plate is stood 2 hours.Instrument is read using ELISA to carry out with the absorbing wavelength of 540nm
It measures.
Cytotoxicity detects
Compound 1-8 detects display, IC for the cytotoxicity of 3 kinds of human cancer cell's strains (A549, HepG2 and PC3)50
Range from 0.001~100 μM, and be then for mdck cell>100 μM (tables 3).Using Vepsid and taxol as positive control
Group.
Notably, for three kinds of cancer cell line (A549, HepG2 and PC3), Antrocamol LT3 (compound 4)
It is most potential.For A549, HepG2 and PC3 cancer cell line, IC50Respectively 0.080,0.1060 and 0.001 μM.
Antrocamols is ubiquinone derivative, with 4-hydroxy-2,3-dimethoxy-6-methyl-cyclohex-2-
Enone ring structures, it appears that show for the selective cytotoxicity of cancer cell, but the acetylation of the positions C-4 such as 4-
Acetylantrocamol LT3 (compound 2), reduce the activity of antrocamols.Compound 1-8 comes under ubiquinone class,
And relatively low cytotoxicity is all shown for non-cancerous cells strain (MDCK) cell.Compound 9-11 is then shown for normal
Or cancer cell line all no cytotoxicities.
The discussion of cytotoxicity test result and structure
Compare ubiquinone analog derivative (compound 1-8), it is found that different cytotoxicity degree is related to its chemical constitution.It is first
First, the Studies on Ubiquinone Derivatives with 4-hydroxy-cyclohex-2-enone ring structures, it may be possible to have active anticancer must
The group needed.Second, the ubiquinone with 4-hydroxy-cyclohex-2-enone ring structures and 4-acetate groups
Class compound is compared with its corresponding parent compound has lower activity, such as compound 2,6 and 8.Third, there are one tools
In the Studies on Ubiquinone Derivatives of the 4-hydroxy-cyclohex-2-enone ring structures of the arbitrary hydroxyl of side chain, anticancer can be increased
Activity, such as compound 2,4 has 17-hydroxyl groups and there are one 15-hydroxyl groups for antrocamol LT1 tools.
4th, the Studies on Ubiquinone Derivatives with 1,4-benzoquinone (paraquinone) may be more selective for PC3 and A549 cells, but
It is then no for HepG2 cell strains.Meanwhile being compared with compound 5, compound 3 has normal cell strain (mdck cell strain)
Lower cytotoxicity.And compared with compound 3, the compound 7 with 3-methylfuran-2-one is for cancer cell line table
Reveal lower activity.However, being compared with compound 5, compound 7 has normal cell strain (mdck cell strain) lower
Cytotoxicity.
According to the above results, there are one the Studies on Ubiquinone Derivatives pair of 4-hydroxy-cyclohex-2-enone ring structures for tool
It is contributive in active anticancer.It is interesting that being compared with antroquinonol and 4-acetate, in side chain tool, there are one appoint
The hydroxyl of meaning significantly increases active anticancer.Compound 1-8 is for cancer cell line, it appears that shows selective cell toxicant
Property.
Further, two benzenoids (compound 9 and 10) and a maleic compound (compound
11) lower activity, is shown for cancer cell line, but only compound 9 shows a little activity for PC3 cell strains,
IC50For 13.2590 μM (tables 3).
Compound 1-4 and 7-11 also show relatively low toxicity, for non-cancerous cells strain (MDCK), IC50For>
100μM。
Table 3 extracts the cytotoxicity from the compound 1-11 of Antrodia camphorata
A) here it is shown that result is average value (n=6)
For this case, although the result in cytotoxicity detection of chemical combination 1,3 is not most ideal, the two is for lung gland
The cell strain of cancer, liver cancer and prostate cancer still has anticancer effect, and the effect and is not disclosed for.Compound 1 belongs to new
Compound, and compound 1,3 has common general formula (following Formula XII depicted).
Wherein R is H or OMe.
When R is H, as this case compound 1 (antrocinnamone).
When R is OMe, as this case compound 3 (quinone Q3).
As seen from the above embodiment, the exploitation value in the true tool industry of Antrodia camphorata compound provided by the present invention and application thereof
Value, the only above narration is only the preferred embodiments of the invention explanation, all to be skillful in this those skilled in the art when be according to above-mentioned explanation
And make other various improvement, only these changes are still fallen in spirit and the scope of the claims bounded by of the present invention.
Claims (4)
1. a kind of compound of separated from Antrodia sesame, is indicated with Formulas I：
2. a kind of compound of separated from Antrodia sesame is used to prepare the purposes for inhibiting tumour growth drug, the compound is with Formula XII
It indicates：
Wherein R is H or OMe, which is one of adenocarcinoma of lung, liver cancer and prostate cancer.
3. purposes according to claim 2, the wherein R in the compound are H, indicated with Formulas I：
4. purposes according to claim 2, the wherein R of the compound are OMe, indicated with formula III：
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| TW106106555A TW201831436A (en) | 2017-02-24 | 2017-02-24 | Compound isolated from Antrodia camphorata and applications therefor capable of being used as a pharmaceutical product to inhibit the growth of cancerous cells |
| TW106106555 | 2017-02-24 |
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| CN113402371A (en) * | 2021-06-23 | 2021-09-17 | 上海理工大学 | 2, 3-dimethoxy-5-methyl-1-hydroxy-4 benzoquinone compound, preparation method and application |
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| CN114487252B (en) * | 2021-12-28 | 2024-03-26 | 陕西嘉禾生物科技股份有限公司 | Thin-layer chromatography identification method for distinguishing Antrodia camphorata from Antrodia camphorata |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5527789A (en) * | 1992-02-24 | 1996-06-18 | East Carolina University | Method of inhibiting carcinogenesis by treatment with dehydroepiandrosterone and analogs thereof |
| CN105263893A (en) * | 2013-02-20 | 2016-01-20 | 国鼎生物科技股份有限公司 | Cyclohexenone compositions and process for making thereof |
-
2017
- 2017-02-24 TW TW106106555A patent/TW201831436A/en unknown
- 2017-03-16 CN CN201710156444.8A patent/CN108503523A/en active Pending
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2018
- 2018-02-12 DE DE102018103030.4A patent/DE102018103030A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5527789A (en) * | 1992-02-24 | 1996-06-18 | East Carolina University | Method of inhibiting carcinogenesis by treatment with dehydroepiandrosterone and analogs thereof |
| CN105263893A (en) * | 2013-02-20 | 2016-01-20 | 国鼎生物科技股份有限公司 | Cyclohexenone compositions and process for making thereof |
Non-Patent Citations (2)
| Title |
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| KEVIN CHI-CHUNG CHOU,SHANG-HAN YANG,HSIANG-LIN WU等: "Biosynthesis of Antroquinonol and 4‑Acetylantroquinonol B via a Polyketide Pathway Using Orsellinic Acid as a Ring Precursor in Antrodia cinnamomea", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
| MADAMANCHI GEETHANGILI AND YEW-MIN TZENG: "Review of Pharmacological Effects of Antrodia camphorata and Its Bioactive Compounds", 《EVIDENCE-BASED COMPLEMENTARY AND ALTERNATIVE MEDICINE》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113402371A (en) * | 2021-06-23 | 2021-09-17 | 上海理工大学 | 2, 3-dimethoxy-5-methyl-1-hydroxy-4 benzoquinone compound, preparation method and application |
| CN113402371B (en) * | 2021-06-23 | 2022-09-06 | 上海理工大学 | 2, 3-dimethoxy-5-methyl-1-hydroxy-4 benzoquinone compound, preparation method and application |
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| TW201831436A (en) | 2018-09-01 |
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