JPH0291024A - Physiologically active lipid - Google Patents
Physiologically active lipidInfo
- Publication number
- JPH0291024A JPH0291024A JP24095788A JP24095788A JPH0291024A JP H0291024 A JPH0291024 A JP H0291024A JP 24095788 A JP24095788 A JP 24095788A JP 24095788 A JP24095788 A JP 24095788A JP H0291024 A JPH0291024 A JP H0291024A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- lipid
- antiviral
- physiologically active
- glucose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002632 lipids Chemical class 0.000 title claims abstract description 12
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 15
- 229930186217 Glycolipid Natural products 0.000 claims abstract description 13
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 12
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000004676 glycans Chemical class 0.000 claims abstract description 8
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 8
- 239000005017 polysaccharide Substances 0.000 claims abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 7
- 229930195729 fatty acid Natural products 0.000 claims abstract description 7
- 239000000194 fatty acid Substances 0.000 claims abstract description 7
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 6
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 6
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 4
- 239000000470 constituent Substances 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 18
- 239000008103 glucose Substances 0.000 abstract description 18
- 239000005720 sucrose Substances 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 13
- 229930006000 Sucrose Natural products 0.000 abstract description 11
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003612 virological effect Effects 0.000 abstract description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract description 2
- 208000030507 AIDS Diseases 0.000 abstract description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 2
- 239000005642 Oleic acid Substances 0.000 abstract description 2
- 235000021314 Palmitic acid Nutrition 0.000 abstract description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract description 2
- 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 abstract description 2
- 159000000007 calcium salts Chemical class 0.000 abstract description 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract description 2
- 159000000003 magnesium salts Chemical class 0.000 abstract description 2
- 150000004702 methyl esters Chemical class 0.000 abstract description 2
- 150000004671 saturated fatty acids Chemical class 0.000 abstract description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract description 2
- 230000002411 adverse Effects 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- -1 isolobose Chemical compound 0.000 description 31
- 235000000346 sugar Nutrition 0.000 description 14
- 239000003814 drug Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 10
- 241000700605 Viruses Species 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 150000008163 sugars Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 241000712461 unidentified influenza virus Species 0.000 description 6
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000003443 antiviral agent Substances 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 229930182830 galactose Natural products 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- SHZGCJCMOBCMKK-UHFFFAOYSA-N 6-methyloxane-2,3,4,5-tetrol Chemical compound CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- YPZMPEPLWKRVLD-UHFFFAOYSA-N 2,3,4,5,6,7-hexahydroxyheptanal Chemical compound OCC(O)C(O)C(O)C(O)C(O)C=O YPZMPEPLWKRVLD-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 150000008266 deoxy sugars Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 229940097043 glucuronic acid Drugs 0.000 description 2
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 150000005217 methyl ethers Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- RGTIBVZDHOMOKC-UHFFFAOYSA-N stearolic acid Chemical compound CCCCCCCCC#CCCCCCCCC(O)=O RGTIBVZDHOMOKC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 229940126585 therapeutic drug Drugs 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- XJFIPJXYYUYQIC-VZFHVOOUSA-N (2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-6-methylheptanal Chemical compound CC([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)(O)C XJFIPJXYYUYQIC-VZFHVOOUSA-N 0.000 description 1
- YPZMPEPLWKRVLD-CJZRUXIPSA-N (2r,3s,4r,5r,6r)-2,3,4,5,6,7-hexahydroxyheptanal Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O YPZMPEPLWKRVLD-CJZRUXIPSA-N 0.000 description 1
- FDWRIIDFYSUTDP-KVTDHHQDSA-N (2r,4r,5s,6r)-6-methyloxane-2,4,5-triol Chemical compound C[C@H]1O[C@@H](O)C[C@@H](O)[C@@H]1O FDWRIIDFYSUTDP-KVTDHHQDSA-N 0.000 description 1
- YPZMPEPLWKRVLD-BIVRFLNRSA-N (2s,3s,4r,5r,6s)-2,3,4,5,6,7-hexahydroxyheptanal Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O YPZMPEPLWKRVLD-BIVRFLNRSA-N 0.000 description 1
- KSHYQYHHIKNYAY-NDBSEGGWSA-N (3R,4S,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(=O)CO KSHYQYHHIKNYAY-NDBSEGGWSA-N 0.000 description 1
- KSHYQYHHIKNYAY-PNAXYBNRSA-N (3S,4S,5R,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO KSHYQYHHIKNYAY-PNAXYBNRSA-N 0.000 description 1
- OUSKVHOYPHDTIA-JRTVQGFMSA-N (3r,4s,5s,6r)-3,4,5,6,7-pentahydroxyheptan-2-one Chemical compound CC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO OUSKVHOYPHDTIA-JRTVQGFMSA-N 0.000 description 1
- ILKPSYMQOVSEEU-QYNIQEEDSA-N (4R,5S,6R)-4,5,6,7-tetrahydroxyheptan-2-one Chemical compound CC(=O)C[C@@H](O)[C@H](O)[C@H](O)CO ILKPSYMQOVSEEU-QYNIQEEDSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
- FDWRIIDFYSUTDP-UHFFFAOYSA-N 102850-49-7 Natural products CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 1
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JWFRNGYBHLBCMB-UHFFFAOYSA-N D-Canaytose Natural products CC(O)C(O)C(O)CC=O JWFRNGYBHLBCMB-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-BZINKQHNSA-N D-Guluronic Acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-BZINKQHNSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- HSNZZMHEPUFJNZ-QMTIVRBISA-N D-keto-manno-heptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-QMTIVRBISA-N 0.000 description 1
- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 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
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- YQLFLCVNXSPEKQ-UHFFFAOYSA-N Mycarose Natural products CC1OC(O)CC(C)(O)C1O YQLFLCVNXSPEKQ-UHFFFAOYSA-N 0.000 description 1
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 150000001363 alloheptuloses Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- IAJILQKETJEXLJ-LECHCGJUSA-N iduronic acid Chemical compound O=C[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-LECHCGJUSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- JYAQWANEOPJVEY-LYFYHCNISA-N mycarose Chemical compound C[C@H](O)[C@H](O)[C@](C)(O)CC=O JYAQWANEOPJVEY-LYFYHCNISA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- HSNZZMHEPUFJNZ-SHUUEZRQSA-N sedoheptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-SHUUEZRQSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- NMHIUKCEPXGTRP-HCWXCVPCSA-N streptose Chemical compound C[C@H](O)[C@](O)(C=O)[C@@H](O)C=O NMHIUKCEPXGTRP-HCWXCVPCSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 150000003478 taloheptuloses Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、抗ウィルス性生理活性脂質に関し、特に二塩
基酸結合の有機酸結合型糖脂質を有効成分とする抗ウィ
ルス性生理活性脂質に関するものである。Detailed Description of the Invention (Industrial Application Field) The present invention relates to an antiviral physiologically active lipid, and more particularly to an antiviral physiologically active lipid containing a dibasic acid-bonded organic acid-bound glycolipid as an active ingredient. It is something.
（従来の技術）
従来ウィルス病に対する治療薬としては、ワクチンがそ
の主なものであった。しかし、変異し易いウィルスに対
してワクチンは最良とは言い難い。(Prior Art) Vaccines have traditionally been the main therapeutic agents for viral diseases. However, it is difficult to say that vaccines are the best for viruses that mutate easily.
現在ヘルペス、エイズ等のウィルス性疾患に対する直接
的な治療薬は少なく、対症療法が主として行われている
。Currently, there are few direct therapeutic drugs for viral diseases such as herpes and AIDS, and symptomatic treatment is mainly performed.
従来、直接的な治療薬として、抗ウィルス活性の高い合
成された化学物質からなる抗ウィルス剤が提案されてい
る。Conventionally, antiviral agents consisting of synthetic chemical substances with high antiviral activity have been proposed as direct therapeutic agents.
（発明が解決しようとする課題）
しかしながら、このような従来の直接的治療薬として化
学的に合成された物質の中には、抗ウィルス活性が高い
ものもあるが、副作用が大きいため実用化し難いものが
多く、副作用の少ない抗ウィルス剤の開発が望まれてい
る。(Problem to be solved by the invention) However, although some of these chemically synthesized substances used as conventional direct therapeutic drugs have high antiviral activity, they have large side effects and are difficult to put into practical use. There are many antiviral agents, and the development of antiviral agents with fewer side effects is desired.
本発明はこのような課題を解決するためのもので、高い
抗ウィルス活性を有し、かつ副作用の少ない抗ウィルス
性生理活性脂質を提供することを目的としている。The present invention is intended to solve these problems, and aims to provide an antiviral physiologically active lipid that has high antiviral activity and fewer side effects.
（課題を解決するための手段）
本発明は、単糖またはオリゴ糖、多糖に、構成単ｉｔ！
１．モル当たり、炭素数３〜７の二塩基酸１〜４モル
、および炭素数６〜２４の脂肪酸１〜４モルを有する有
機酸結合型糖脂質またはその誘導体からなる抗ウィルス
性生理活性脂質である。(Means for Solving the Problems) The present invention provides monosaccharides, oligosaccharides, and polysaccharides with constituent units!
1. It is an antiviral physiologically active lipid consisting of an organic acid-binding glycolipid or a derivative thereof having 1 to 4 moles of a dibasic acid having 3 to 7 carbon atoms and 1 to 4 moles of a fatty acid having 6 to 24 carbon atoms per mole. .
上記糖脂質を合成する際に使用するものとして、糖はＯ
Ｈ基を有する天然糖、合成糖が使用でき、単糖、オリゴ
糖、多糖のいずれも使用できる。単糖としては５単糖、
６単糖、多糖、デオキシ糖、糖アルコール、酸性糖、糖
メチルエーテル、分技糖などが挙げられる。Sugar is used when synthesizing the above glycolipids.
Natural sugars and synthetic sugars having an H group can be used, and any of monosaccharides, oligosaccharides, and polysaccharides can be used. As a monosaccharide, there are 5 monosaccharides,
Examples include hexamonosaccharides, polysaccharides, deoxy sugars, sugar alcohols, acid sugars, sugar methyl ethers, and fractionated sugars.
例えば５単糖のアラビノース、キシロース、リキソース
、リボース、キシルロース、リブロース等が例示できる
。また、６単糖はガラクトース、グルコース、クロース
、マンノース、ソルボース、タガトース、プシコース、
フルクトース等が例示できる。多糖はグリセロガラクト
へプトース、グリセログルコへプトース、グリセログ口
へプトース、グリセロマンノへプトース、アルトロヘプ
ツロース、マンノヘプツロース、タロヘプツロース、ア
ロヘプツロース、グリセロマンノオクツロース、グリセ
ロガラクトオクツロース、エリスログルコイヌロース、
エリスロガラクトイヌロース等が例示できる。Examples include five monosaccharides such as arabinose, xylose, lyxose, ribose, xylulose, and ribulose. In addition, the six monosaccharides are galactose, glucose, sucrose, mannose, sorbose, tagatose, psicose,
Examples include fructose. Polysaccharides are glycerogalactoheptose, glyceroglucoheptose, glycerogalactoheptose, glyceromannoheptose, altroheptulose, mannoheptulose, taloheptulose, alloheptulose, glyceromannooctulose, glycerogalactooctulose, erythroglucoinulose ,
Examples include erythrogalactinulose.
デオキシ糖はモノデオキシ糖のデオキシリボース、イソ
ロブオース、デオキシヘキソース、デオキシアルドース
、デオキシクロース、デオキシグロース、デオキシクロ
ース、フコース、ラムノース、デオキシアラビノヘキソ
ース、デオキシキシロヘキソース、ジデオキシ糖のジギ
トキソース、ジデオキシリキソヘキソース、ボイビノー
ス、アラビノ−ス、アベコース、コリドース、チベロー
ス、パラドース等が例示できる。Deoxy sugars include monodeoxy sugars deoxyribose, isolobose, deoxyhexose, deoxyaldose, deoxyclose, deoxygulose, deoxyclose, fucose, rhamnose, deoxyarabinohexose, deoxyxylohexose, dideoxy sugars digitoxose, dideoxylyxohexose, Examples include voivinose, arabinose, abecose, collidose, tiberose, and paradose.
糖アルコールはエリトリトール、アラビトール、キシリ
トール、リビトール、ガラクチトール、グルシトール、
マンニトール、セドヘプチトール、ベルセイトール、ボ
レミトール、ステアロ−ル、ボロエリトール等が例示で
きる。Sugar alcohols include erythritol, arabitol, xylitol, ribitol, galactitol, glucitol,
Examples include mannitol, sedoheptitol, verceitol, boremitol, stearol, and boroerytol.
酸性糖はイズロン酸、ガラクツロン酸、グルクロン酸、
グルロン酸、マンヌロン酸、アラビノへキスロン酸等が
例示できる。Acidic sugars are iduronic acid, galacturonic acid, glucuronic acid,
Examples include guluronic acid, mannuronic acid, and arabinohexuronic acid.
糖メチルエーテルはメチルガラクトース、メチクグルク
ロン酸、メチルグルコース、ジメチルグルコース、デオ
キシメチルマンノース、デオキシメチルクロース、デオ
キシメチルガラクトース、デオキシジメチルガラクトー
ス、デオキシメチルアルドロース、デオキシメチルガラ
クトース、デオキシメチルグルコース、ジデオキシメチ
ルグルコース、ジデオキシメチルキシロヘキソース、ジ
デオキシメチルリキソヘキソース、ヂデオキシメチルリ
ボヘキソース、ジデオキシメチルグリセロヘキソース等
が例示できる。Sugar methyl ethers include methyl galactose, methic glucuronic acid, methyl glucose, dimethyl glucose, deoxymethyl mannose, deoxymethyl crose, deoxymethyl galactose, deoxydimethyl galactose, deoxymethyl aldrose, deoxymethyl galactose, deoxymethyl glucose, dideoxymethyl glucose , dideoxymethyl xylohexose, dideoxymethyl lyxohexose, dideoxymethyl ribohexose, dideoxymethylglycerohexose, and the like.
分枝糖はアビオース、アルカツース、フラジノース、ク
ロモースＢ１コルグセポース、ストレプトース、ノビオ
ース、ハマメロース、ミカロース等が例示できる。Examples of branched sugars include aviose, alkatose, furazinose, chromose B1 korgsepose, streptose, nobiose, hamamellose, mycarose, and the like.
オリゴ糖、多糖は上記単糖が２つ以上結合したものであ
る。Oligosaccharides and polysaccharides are two or more of the above monosaccharides linked together.
二塩基酸は、炭素数３〜７のマロン酸、コハク酸、グル
タル酸、アジピン酸、ピメリン酸および、モノアルコー
ルとのハーフエステル、アルカリとのモノ塩が例示でき
る。炭素数が７を超えると、ウィルスに対する親和性が
弱くなるので好ましくない。Examples of dibasic acids include malonic acid, succinic acid, glutaric acid, adipic acid, and pimelic acid having 3 to 7 carbon atoms, half esters with monoalcohols, and monosalts with alkali. If the number of carbon atoms exceeds 7, the affinity for viruses will be weakened, which is not preferable.
脂肪酸は長鎖飽和脂肪酸、長鎖不飽和脂肪酸のうち炭素
数６〜２４のものを使用でき、カプロン酸、エナント酸
、カプリル酸、ウンデカン酸、ラウリン酸二 トリデカ
ン酸、ミリスチン酸、ペンタデカン酸、パルミチン酸、
パルミトオレイン酸、ヘプタデカン酸、ステアリン酸、
オレイン酸、エライジン酸、リノール酸、リシルイン酸
、ステアロール酸、リシルイン酸、アラキン酸、゛アラ
キドン酸、ヘヘン酸、エイコサペンタエン酸、ドコサヘ
キサエン酸、エルシン酸、ブラシジン酸、リグノセリン
酸等が例示できる。As fatty acids, long-chain saturated fatty acids and long-chain unsaturated fatty acids with 6 to 24 carbon atoms can be used, including caproic acid, enanthic acid, caprylic acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, and palmitic acid. acid,
palmitooleic acid, heptadecanoic acid, stearic acid,
Examples include oleic acid, elaidic acid, linoleic acid, lysyllic acid, stearolic acid, lysyllic acid, arachidic acid, arachidonic acid, hehenic acid, eicosapentaenoic acid, docosahexaenoic acid, erucic acid, brassic acid, and lignoceric acid.
有機酸結合型糖脂質を合成する場合、例として、まず、
糖と脂肪酸酸ハロゲン化物をピリジン中で反応させる。When synthesizing organic acid-bound glycolipids, for example, first,
Sugar and fatty acid halide are reacted in pyridine.
ピリジン除去後、無水二塩基酸とジメチルアミノピリジ
ンを加えクロロホルム中で反応させる。反応後クロロホ
ルムを除去し、反応物をシリカゲルカラムにかけ精製す
る。反応物は、ペーパークロマトグラフィー、薄層クロ
マトグラフィー、ガスクロマトグラフィー、質量分析等
によって同定することができる。After removing pyridine, dibasic anhydride and dimethylaminopyridine are added and reacted in chloroform. After the reaction, chloroform is removed and the reaction product is purified by applying it to a silica gel column. Reactants can be identified by paper chromatography, thin layer chromatography, gas chromatography, mass spectrometry, and the like.
本発明において有機酸結合型糖脂質の誘導体の例として
は、メチルエステル、エチルエステル、ナトリウム塩、
カリウム塩、カルシウム塩、マグネシウム塩等の誘導体
をいう。In the present invention, examples of organic acid-bound glycolipid derivatives include methyl ester, ethyl ester, sodium salt,
Refers to derivatives of potassium salts, calcium salts, magnesium salts, etc.
本発明の抗ウィルス性生理活性脂質は、このような二塩
基酸結合糖脂質からなるものであり、これを有効成分と
し、必要により他の成分をさらに含有して、抗ウィルス
剤として使用される。本発明の抗ウィルス性生理活性脂
質は一般のウィルスに対して高い抗ウィルス活性を有し
、特にヘルペスウィルス、インフルエンザウィルス等の
エンベロープを有するウィルス科に属するウィルスに有
効である。The antiviral physiologically active lipid of the present invention is composed of such a dibasic acid-bonded glycolipid, and is used as an antiviral agent by containing this as an active ingredient and further containing other ingredients if necessary. . The antiviral physiologically active lipid of the present invention has high antiviral activity against general viruses, and is particularly effective against viruses belonging to the enveloped virus family, such as herpes virus and influenza virus.
本発明に用いる有機酸結合型糖脂質の有効薬物濃度（１
０，。）は、１０〜１００羅／−で詳しい値は実施例に
示す、ここで有効薬物濃度は、ＨｅＬａ細胞またはＭＤ
ＣＫ細胞にウィルスを感染させ、さらに有機酸結合型糖
脂質を細胞に対し毒性を示さない程度のエタノールに溶
かして加え、６〜１２時間ごとに感染の程度を観察し、
４８時間後に全細胞のうち５０％が細胞変性を起こした
薬物濃度をＴＤＳ。Effective drug concentration (1
0,. ) is 10 to 100 Ra/-, detailed values are shown in the examples. Here, the effective drug concentration is HeLa cells or MD
Infect CK cells with the virus, add an organic acid-bound glycolipid dissolved in ethanol that is not toxic to the cells, and observe the degree of infection every 6 to 12 hours.
After 48 hours, the drug concentration at which 50% of all cells underwent cell degeneration was determined by TDS.
とじた値である。This is the closed value.
本発明において有機酸結合型糖脂質の人体への投与量は
１〜１０００■／ｋｇ／日である。In the present invention, the amount of organic acid-bound glycolipid administered to the human body is 1 to 1000 μg/kg/day.
本発明の抗ウィルス性生理活性脂質は、経口投与製剤、
注射用薬剤、まては外用剤として軟膏剤、ローション剤
、リニメン・ト剤などの形で用いることができるが、投
与方法はこれらに限定されるものではない。The antiviral physiologically active lipid of the present invention can be used in oral administration formulations,
It can be used as an injectable drug or as an external preparation in the form of an ointment, lotion, liniment, etc., but the administration method is not limited to these.
（発明の効果）
本発明の有機酸結合型糖脂質は、高い抗ウィルス活性を
有し、副作用が少ない抗ウィルス性生理活性脂質である
。(Effects of the Invention) The organic acid-bound glycolipid of the present invention is an antiviral physiologically active lipid that has high antiviral activity and has few side effects.
（実施例） 以下実施例により、本発明をさらに詳細に説明する。(Example) The present invention will be explained in more detail with reference to Examples below.
実施例１ 有機酸結合型糖脂質の合成
グルタリル・グルコース脂質の合成
糖として、グルコース１ｇをピリジン１０艷に溶解し、
脂肪酸酸ハロゲン化物として、２倍モルのバルミチン醗
酵クロライド（３ｇ）を氷水に滴下しながら加える。滴
下後室温で約２時間反応させる。反応後蒸留してピリジ
ンを除去する。Example 1 Synthesis of organic acid-bound glycolipids As a synthetic sugar for glutaryl-glucose lipids, 1 g of glucose was dissolved in 10 g of pyridine,
As a fatty acid halide, 2 times the mole of valmitine fermentation chloride (3 g) is added dropwise to ice water. After dropping, the mixture is allowed to react at room temperature for about 2 hours. After the reaction, pyridine is removed by distillation.
反応物のグルコース脂質（約２ｇ）に二塩基酸とし・て
、４倍モルの無水グルタル酸（１，５ｇ）と２倍モルの
ジメチルアミノピリジン（１−）を加え、クロロホルム
中、室温で約２時間反応させる。反応後、減圧濃縮して
、クロロホルムを除去する。Add 4 times the mole of glutaric anhydride (1.5 g) and 2 times the mole of dimethylaminopyridine (1-) as dibasic acids to glucose lipid (approximately 2 g) as a reactant, and add about 2 times the mole of dimethylaminopyridine (1-) in chloroform at room temperature. Let react for 2 hours. After the reaction, concentrate under reduced pressure to remove chloroform.
濃縮物をシリカゲルを充填したカラムにかけ、クロロホ
ルム：メタノール（９： １）の溶出溶媒で溶出させ、
目的のグルタリル・グルコース脂質を精製する。The concentrate was applied to a column packed with silica gel and eluted with an elution solvent of chloroform:methanol (9:1).
Purify the desired glutaryl/glucose lipid.
この化合物は、ＩＲ、ガスクロ、質量分析の結果、分子
量８８４であり、バルミトイル基２個とグルタリル基を
２個結合したグルコースであることを確認した。As a result of IR, gas chromatography, and mass spectrometry, this compound had a molecular weight of 884, and was confirmed to be glucose with two valmitoyl groups and two glutaryl groups bonded.
実施例２ 有機酸結合型糖脂質の合成
グルタリル・スクロース脂質の合成
実施例１において糖としてスクロースを使用し、２倍モ
ルの無水グルタル酸を用いた以外は、実施例１と同様に
した。Example 2 Synthesis of organic acid-bound glycolipid Synthesis of glutaryl-sucrose lipid The procedure of Example 1 was repeated except that sucrose was used as the sugar and 2 times the molar amount of glutaric anhydride was used.
この化合物は、ＩＲ、ガスクロ、質量分析の結果、分子
量９３２であり、バルミトイル基２個とグルタリル基１
個を結合したスクロースであることを確認した。As a result of IR, gas chromatography, and mass spectrometry, this compound has a molecular weight of 932, with two valmitoyl groups and one glutaryl group.
It was confirmed that the sucrose was made by combining two parts.
実施例３ グルタリル・グルコース脂質の単純ヘルペス
ウィルス１型（ｈｅｒｐｅｓ ｓｉｍｐｌｅｘｖｉｒｕ
ｓ ｔｙｐｅ １ ）に対する効果抗ウィルス試験の
開始２４時間前に、２４穴マルチウエルプレートにＨｅ
Ｌａ細胞の単一層を形成しておき、試験を開始する際に
甚大から培地を取り去り、リン酸緩衝食塩水で一度洗浄
する。洗浄したリン酸緩衝食塩水を取り除き、ウシ胎児
血清を３％含むリン酸緩衝食塩水で希釈した単純ヘルペ
スウィルス１型を０．１ｍｌずつ、１２穴に接種する。Example 3 Glutaryl glucose lipid herpes simplex virus type 1
s type 1) 24 hours before the start of the antiviral test, He was injected into a 24-well multi-well plate.
A monolayer of La cells is formed and the medium is removed from the cells at the start of the study and washed once with phosphate buffered saline. The washed phosphate buffered saline was removed, and 0.1 ml of herpes simplex virus type 1 diluted with phosphate buffered saline containing 3% fetal bovine serum was inoculated into 12 wells.
残りの１２穴は対照としてウィルスを含まないリン酸緩
衝食塩水を、０．１ｒｎｉずつ接種する。接種後、約１
時間吸着を行う。１時間後、未吸着のウィルスを取り除
き、ウシ血清を１％含むイーグルＭＥＭ培地を甚大に１
−ずつ加える。培地添加後、エタノールに溶解させた各
濃度のグルタリル・グルコース脂質を加える。プレート
を含湿、５％ＣＯｔ含有卿卵器中、３６．５℃で培養す
る。６〜１２時間おきに倒立顕微鏡下に各プレートの細
胞の様子を観察し、ウィルスによる細胞変性の程度を各
人ごとに判定する。The remaining 12 wells are inoculated with virus-free phosphate buffered saline at 0.1 rni each as a control. After vaccination, approximately 1
Perform time adsorption. After 1 hour, remove unadsorbed virus and add 1 ml of Eagle's MEM medium containing 1% bovine serum.
- Add each. After adding the medium, each concentration of glutaryl glucose lipid dissolved in ethanol is added. The plates are incubated at 36.5° C. in a humidified, 5% COt containing chamber. The state of the cells on each plate is observed under an inverted microscope every 6 to 12 hours, and the degree of cell degeneration caused by the virus is determined for each person.
その結果、グルタリル・グルコース脂質の単純ヘルペス
ウィルス１型のＨｅＬａ細胞への感染を５０％抑制する
濃度（ＴＤｓ。）は８０ｘ／−であった。As a result, the concentration (TDs.) of glutaryl glucose lipid that inhibited the infection of herpes simplex virus type 1 to HeLa cells by 50% was 80x/-.
実施例４ グルタリル・グルコース脂質のインフルエン
ザウィルス（ｉｎｆｌｕｅｎｚａ ｖｉｒｕｓ）に対す
る効果
抗ウィルス試験に使用する細胞としてＭＤＣＫ（イヌ腎
由来）細胞を用い、ウィルスとしてインフルエンザウィ
ルスを感染させ、感染後の培地としてウシ血清アルブミ
ンを０．１ ％、トリプシンを。Example 4 Effect of glutaryl/glucose lipids on influenza virus MDCK (canine kidney derived) cells were used as the cells used in the antiviral test, infected with influenza virus as the virus, and bovine serum albumin was used as the medium after infection. 0.1% trypsin.
２１）Ｉ）１１１％ファンギゾンを０．５ｐｐｍ含むイ
ーグル強化ＭＥＭ培地を使用する以外は実施例３と同じ
方法を用いる。21) I) Use the same method as in Example 3, except using Eagle's enriched MEM medium containing 0.5 ppm of 111% Fungizon.
その結果、グルタリル・グルコース脂質のインフルエン
ザウィルスのＭＤＣＫ細胞へのＳ 染ヲ５０％抑制する
濃度（ＩＤｓ。）は３３■／−であった。As a result, the concentration (IDs) of glutaryl glucose lipid that inhibited S staining of MDCK cells by influenza virus by 50% was 33/-.
実施例５ グルタリル・スクロース脂質の単純ヘルペス
ウィルス１型に対する効果
添加する薬物としてグルタリル・スクロース脂質を使用
する以外は実施例３と同じ方法を用いる。Example 5 Effect of glutaryl-sucrose lipid on herpes simplex virus type 1 The same method as in Example 3 is used except that glutaryl-sucrose lipid is used as the additive drug.
その結果、グルタリル・スクロース脂質の単純ヘルペス
ウィルス１型のＨｅＬａ細胞への感染を５０％抑制する
濃度（１０％。）は５０ｎ／−であった。As a result, the concentration (10%) of glutaryl sucrose lipid that inhibited the infection of herpes simplex virus type 1 to HeLa cells by 50% was 50n/-.
実施例６ グルタリル・スクロース脂質のインフルエン
ザウィルスに対する効果
添加する薬物としてグルタリル・スクロース脂質を使用
する以外は実施例４と同じ方法を用いる。Example 6 Effect of glutaryl/sucrose lipid on influenza virus The same method as in Example 4 is used except that glutaryl/sucrose lipid is used as the added drug.
その結果、グルタリル・スクロース脂質のインフルエン
ザウィルスのＭＤＣＫ細胞への感染を５０％抑制する濃
度（ＩＤｓｏ）は２０ｎ／ｒｄであった。As a result, the concentration (IDso) of glutaryl sucrose lipid that inhibited influenza virus infection of MDCK cells by 50% was 20n/rd.
実施例７ グルタリル・グルコース脂質のハーフエチル
エステルの単純ヘルペスウィル
スｌ型（ｈｅｒｐｅｓ ｓｉｍｐｌｅｘ ｖｉｒｕｓ
ｔｙｐｅｌ）に対する効果
添加する薬物としてグルタリル・グルコース脂質のハー
フエステルを使用する以外は実施例３と同じ方法を用い
る。Example 7 Herpes simplex virus type I half-ethyl ester of glutaryl glucose lipid
The same method as in Example 3 is used except that a half ester of glutaryl glucose lipid is used as the added drug.
その結果、グルタリル・グルコース脂質のハーフエステ
ルの単純ヘルペスウィルス１型のＩＩｅＬａＨｅＬａ細
胞を５０％抑制する濃度（ＩＤｓ。）は１００賄／−で
あった。As a result, the concentration (IDs.) of glutaryl glucose lipid half ester that inhibited herpes simplex virus type 1 IIeLaHeLa cells by 50% was 100/-.
実施例８ グルタリル・スクロース脂質のＣａ塩のの単
純ヘルペスウィルス１型に対する
効果
添加する薬物としてグルタリル・スクロース脂質のＣａ
塩を使用する以外は実施例３と同じ方法を用いる。Example 8 Effect of Ca salt of glutaryl/sucrose lipid on herpes simplex virus type 1. Ca salt of glutaryl/sucrose lipid as an added drug.
The same method as in Example 3 is used except that salt is used.
その結果、グルタリル・スクロース脂質のＣａ塩の単純
ヘルペスウィルス１型のＨｅＬａ細胞への感染を５０％
抑制する濃度（ＩＤｓ。）は６０ｎ／−であっ。As a result, the Ca salt of glutaryl sucrose lipid reduced the infection of herpes simplex virus type 1 HeLa cells by 50%.
The inhibitory concentration (IDs.) was 60n/-.
た。Ta.
実施例９ 有機酸結合型糖脂質の合成
サクシニル・グルコース脂質の合成
実施例１において脂肪酸酸ハロゲン化物として、オレイ
ン酸クロライド、二塩基酸として無水コハク酸を用いた
以外は、実施例１と同様にした。Example 9 Synthesis of organic acid-bound glycolipids Synthesis of succinyl-glucose lipids Same as Example 1 except that oleic acid chloride was used as the fatty acid halide and succinic anhydride was used as the dibasic acid. did.
この化合物は、ＩＲ、ガスクロ、質量分析の結果、分子
量８０８であり、オレイル基２個とサクシニル基を２個
結合したグルコースであることを確認した。As a result of IR, gas chromatography, and mass spectrometry, this compound had a molecular weight of 808, and was confirmed to be glucose with two oleyl groups and two succinyl groups bonded.
実施例１０ サクシニル・グルコース脂質の単純ヘル
ペスウィルス１型に対する効果
添加する薬物としてサクシニル・グルコース脂質を使用
する以外は実施例３と同じ方法を用いる。Example 10 Effect of Succinyl Glucose Lipid on Herpes Simplex Virus Type 1 The same method as in Example 3 is used except that succinyl glucose lipid is used as the added drug.
その結果、サクシニル・グルコース脂質の単純ヘルペス
ウィルスｌ型の１ｌｅＬａ細胞への感染を５０％抑制す
る濃度（ＩＤＳ。）は６０ｎ／−であった。As a result, the concentration (IDS) of succinyl glucose lipid that inhibited the infection of herpes simplex virus type 1 to 1leLa cells by 50% was 60n/-.
Claims (1)
炭素数３〜７の二塩基酸１〜４モル、および炭素数６〜
２４の脂肪酸１〜４モルを有する有機酸結合型糖脂質ま
たはその誘導体からなる抗ウィルス性生理活性脂質。For monosaccharides, oligosaccharides, and polysaccharides, per mole of constituent monosaccharides,
1 to 4 mol of dibasic acid having 3 to 7 carbon atoms, and 6 to 4 mol of carbon atoms
An antiviral physiologically active lipid comprising an organic acid-bound glycolipid or a derivative thereof having 1 to 4 moles of 24 fatty acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24095788A JPH0291024A (en) | 1988-09-28 | 1988-09-28 | Physiologically active lipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24095788A JPH0291024A (en) | 1988-09-28 | 1988-09-28 | Physiologically active lipid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0291024A true JPH0291024A (en) | 1990-03-30 |
Family
ID=17067166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24095788A Pending JPH0291024A (en) | 1988-09-28 | 1988-09-28 | Physiologically active lipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0291024A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007535523A (en) * | 2004-04-30 | 2007-12-06 | ラボラトワール エクスパンシアンス | Use of a compound comprising D-mannoheptulose and / or perseitol for the treatment and prevention of innate immune modulatory diseases |
| US8109355B2 (en) | 2004-09-02 | 2012-02-07 | Kanzaki Kokyukoki Mfg. Co., Ltd. | Hydrostatic transaxle and hydraulically driven vehicle |
-
1988
- 1988-09-28 JP JP24095788A patent/JPH0291024A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007535523A (en) * | 2004-04-30 | 2007-12-06 | ラボラトワール エクスパンシアンス | Use of a compound comprising D-mannoheptulose and / or perseitol for the treatment and prevention of innate immune modulatory diseases |
| JP4903131B2 (en) * | 2004-04-30 | 2012-03-28 | ラボラトワール エクスパンシアンス | Use of a compound comprising D-mannoheptulose and / or perseitol for the treatment and prevention of innate immune modulatory diseases |
| US8109355B2 (en) | 2004-09-02 | 2012-02-07 | Kanzaki Kokyukoki Mfg. Co., Ltd. | Hydrostatic transaxle and hydraulically driven vehicle |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU783142B2 (en) | Nucleoside analogs with carboxamidine modified monocyclic base | |
| JP3865411B2 (en) | Anti-endotoxin compounds | |
| JP2952505B2 (en) | Antiviral drugs | |
| JP3458900B2 (en) | Antiviral lipid-nucleoside conjugate, drug and liposome using the same | |
| WO2003105769A2 (en) | Synthetic c-glycolipid and its use for treating cancer infectious diseases and autoimmune diseases | |
| US10722574B2 (en) | Use and preparation of glycolipids as adjuvants in vaccines | |
| TW202110459A (en) | Saponin conjugate and vaccine or pharmaceutical composition comprising the same | |
| EP0374888A2 (en) | Sulfated tannins and theirs salts | |
| NO300014B1 (en) | Chemical connections | |
| USRE32268E (en) | Therapeutic composition and method of therapeutically treating warm blooded animals therewith | |
| JP2967998B2 (en) | New neplanosin derivatives | |
| JPH0291024A (en) | Physiologically active lipid | |
| CA2110495A1 (en) | Immunosuppressive and tolerogenic oligosaccharide derivatives | |
| JP5574432B2 (en) | Esterified α-galactosylceramides | |
| JPH05247078A (en) | Sugar compound, sialic acid-containing sugar chain biosyhnthesis inhibitor, its production, and new intermediate | |
| JP4879398B2 (en) | Glyceryl nucleotides, their production and use | |
| PT88568B (en) | PROCESS FOR THE PREPARATION OF SUCROSE DERIVATIVES | |
| AU777920B2 (en) | Beta-D-5-thioxylose derivatives, preparation method and therapeutic use | |
| WO1990003172A2 (en) | Bile acids for treatment of viral infections | |
| JP2005533881A (en) | Gamma interferon binding compounds, methods for their preparation, and drugs containing them | |
| WO1995034296A1 (en) | Use of rooperol and hypoxoside and their derivatives in the treatment of inflammatory | |
| CN114773417B (en) | Cordycepin phosphate and preparation method and application thereof | |
| JPH0278622A (en) | Treatment use of isopropyl ester derivative of mocyaloganglioside | |
| JPH01224396A (en) | Novel steroid saponin and production and novel use of these derivative | |
| US5508390A (en) | Diterpenes having immunomodulatory action |