JPWO2020061457A5 - - Google Patents

Info

Publication number

JPWO2020061457A5

JPWO2020061457A5 JP2021515466A JP2021515466A JPWO2020061457A5 JP WO2020061457 A5 JPWO2020061457 A5 JP WO2020061457A5 JP 2021515466 A JP2021515466 A JP 2021515466A JP 2021515466 A JP2021515466 A JP 2021515466A JP WO2020061457 A5 JPWO2020061457 A5 JP WO2020061457A5

Authority

JP

Japan

Prior art keywords

alkyl

group

alkenyl

optionally substituted

independently selected

Prior art date

2022-09-29

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

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• 125000000217 alkyl group Chemical group 0.000 claims 38
• 229910052799 carbon Inorganic materials 0.000 claims 31
• 125000003342 alkenyl group Chemical group 0.000 claims 19
• 229910052739 hydrogen Inorganic materials 0.000 claims 18
• 229910052760 oxygen Inorganic materials 0.000 claims 16
• 239000003960 organic solvent Substances 0.000 claims 14
• 150000002632 lipids Chemical class 0.000 claims 13
• 150000003839 salts Chemical class 0.000 claims 11
• 239000011780 sodium chloride Substances 0.000 claims 11
• 150000007523 nucleic acids Chemical class 0.000 claims 8
• 108020004707 nucleic acids Proteins 0.000 claims 8
• -1 tertiary amine cation Chemical class 0.000 claims 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
• 239000001257 hydrogen Substances 0.000 claims 6
• 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 6
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 6
• 239000000243 solution Substances 0.000 claims 6
• 125000000623 heterocyclic group Chemical group 0.000 claims 5
• 239000000203 mixture Substances 0.000 claims 5
• 239000002105 nanoparticle Substances 0.000 claims 5
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
• 125000001072 heteroaryl group Chemical group 0.000 claims 4
• 229910052757 nitrogen Inorganic materials 0.000 claims 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims 4
• 229910052717 sulfur Inorganic materials 0.000 claims 4
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 4
• 125000003158 alcohol group Chemical group 0.000 claims 3
• 125000003118 aryl group Chemical group 0.000 claims 3
• 125000000732 arylene group Chemical group 0.000 claims 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
• 150000001768 cations Chemical class 0.000 claims 3
• 125000005549 heteroarylene group Chemical group 0.000 claims 3
• 150000002892 organic cations Chemical class 0.000 claims 3
• 229920001223 polyethylene glycol Chemical class 0.000 claims 3
• 239000000080 wetting agent Substances 0.000 claims 3
• HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
• KILNVBDSWZSGLL-KXQOOQHDSA-O 1,2-di-O-palmitoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-O 0.000 claims 2
• FVXDQWZBHIXIEJ-LNDKUQBDSA-N 1,2-dilinoleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC FVXDQWZBHIXIEJ-LNDKUQBDSA-N 0.000 claims 2
• SNKAWJBJQDLSFF-NVKMUCNASA-O 1,2-dioleoyl-sn-glycero-3-phosphocholine(1+) Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-O 0.000 claims 2
• NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims 2
• RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 2
• JJWKPURADFRFRB-UHFFFAOYSA-N Carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 2
• IMFACGCPASFAPR-UHFFFAOYSA-N Tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 2
• WCGUUGGRBIKTOS-RRHGHHQTSA-N Ursolic acid Natural products O=C(O)[C@@]12[C@@H]([C@@H](C)[C@@H](C)CC1)C=1[C@](C)([C@@]3(C)[C@@H]([C@]4(C)[C@H](C(C)(C)[C@@H](O)CC4)CC3)CC=1)CC2 WCGUUGGRBIKTOS-RRHGHHQTSA-N 0.000 claims 2
• 125000002947 alkylene group Chemical group 0.000 claims 2
• 125000000304 alkynyl group Chemical group 0.000 claims 2
• 238000004440 column chromatography Methods 0.000 claims 2
• 238000009295 crossflow filtration Methods 0.000 claims 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
• 239000008393 encapsulating agent Substances 0.000 claims 2
• 238000009472 formulation Methods 0.000 claims 2
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
• WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims 2
• 150000003904 phospholipids Chemical class 0.000 claims 2
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 2
• GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 2
• KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims 1
• JTERLNYVBOZRHI-PPBJBQABSA-N (2-aminoethoxy)[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC JTERLNYVBOZRHI-PPBJBQABSA-N 0.000 claims 1
• WIHSZOXPODIZSW-KJIWEYRQSA-N (2-aminoethoxy)[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC WIHSZOXPODIZSW-KJIWEYRQSA-N 0.000 claims 1
• XLKQWAMTMYIQMG-SVUPRYTISA-N (2-{[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC XLKQWAMTMYIQMG-SVUPRYTISA-N 0.000 claims 1
• LVNGJLRDBYCPGB-LDLOPFEMSA-N (R)-1,2-distearoylphosphatidylethanolamine zwitterion Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-LDLOPFEMSA-N 0.000 claims 1
• SSCDRSKJTAQNNB-DWEQTYCFSA-N 1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC SSCDRSKJTAQNNB-DWEQTYCFSA-N 0.000 claims 1
• LZLVZIFMYXDKCN-QJWFYWCHSA-N 1,2-di-O-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC LZLVZIFMYXDKCN-QJWFYWCHSA-N 0.000 claims 1
• NJFCSWSRXWCWHV-USYZEHPZSA-O 2-[[(2R)-2,3-bis(octadec-1-enoxy)propoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CCCCCCCCCCCCCCCCC=COC[C@H](COP(O)(=O)OCC[N+](C)(C)C)OC=CCCCCCCCCCCCCCCCC NJFCSWSRXWCWHV-USYZEHPZSA-O 0.000 claims 1
• XXKFQTJOJZELMD-JICBSJGISA-O 2-[[(2R)-2,3-bis[[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy]propoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC XXKFQTJOJZELMD-JICBSJGISA-O 0.000 claims 1
• XLPHMKQBBCKEFO-DHYROEPTSA-N 2-azaniumylethyl [(2R)-2,3-bis(3,7,11,15-tetramethylhexadecanoyloxy)propyl] phosphate Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CC(C)CCCC(C)CCCC(C)CCCC(C)C XLPHMKQBBCKEFO-DHYROEPTSA-N 0.000 claims 1
• SLQKYSPHBZMASJ-QKPORZECSA-N 24-methylene-cholest-8-en-3β-ol Chemical compound C([C@@]12C)C[C@H](O)C[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCC(=C)C(C)C)CC[C@H]21 SLQKYSPHBZMASJ-QKPORZECSA-N 0.000 claims 1
• OILXMJHPFNGGTO-ZAUYPBDWSA-N Brassicasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 claims 1
• OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 claims 1
• SGNBVLSWZMBQTH-PODYLUTMSA-N Campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims 1
• SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims 1
• 229940107161 Cholesterol Drugs 0.000 claims 1
• GZDFHIJNHHMENY-UHFFFAOYSA-N DMPC Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 claims 1
• DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 claims 1
• DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 claims 1
• LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 claims 1
• LKQLRGMMMAHREN-YJFXYUILSA-N N-stearoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC LKQLRGMMMAHREN-YJFXYUILSA-N 0.000 claims 1
• 101700035813 PHI3 Proteins 0.000 claims 1
• 229940067631 Phospholipids Drugs 0.000 claims 1
• 101710008815 Prl3b1 Proteins 0.000 claims 1
• 101710008673 Prl3d4 Proteins 0.000 claims 1
• 101700041438 SWI2 Proteins 0.000 claims 1
• 229940032091 Stigmasterol Drugs 0.000 claims 1
• HCXVJBMSMIARIN-MFBJGPNFSA-N Stigmasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 HCXVJBMSMIARIN-MFBJGPNFSA-N 0.000 claims 1
• XYNPYHXGMWJBLV-VXPJTDKGSA-N Tomatidine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@@]11CC[C@H](C)CN1 XYNPYHXGMWJBLV-VXPJTDKGSA-N 0.000 claims 1
• XYNPYHXGMWJBLV-OFMODGJOSA-N Tomatidine Natural products O[C@@H]1C[C@H]2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]5[C@@H](C)[C@]6(O[C@H]5C4)NC[C@@H](C)CC6)CC3)CC2)CC1 XYNPYHXGMWJBLV-OFMODGJOSA-N 0.000 claims 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
• 239000007983 Tris buffer Substances 0.000 claims 1
• JBBYCBXVYZDRPE-PSXMRANNSA-N [(2R)-2-[12-(2-azido-4-nitroanilino)dodecanoyloxy]-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCNC1=CC=C([N+]([O-])=O)C=C1N=[N+]=[N-] JBBYCBXVYZDRPE-PSXMRANNSA-N 0.000 claims 1
• SUTHKQVOHCMCCF-QZNUWAOFSA-N [(2R)-3-[2-aminoethoxy(hydroxy)phosphoryl]oxy-2-docosa-2,4,6,8,10,12-hexaenoyloxypropyl] docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC SUTHKQVOHCMCCF-QZNUWAOFSA-N 0.000 claims 1
• VLBPIWYTPAXCFJ-XMMPIXPASA-N [(2R)-3-hexadecoxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C VLBPIWYTPAXCFJ-XMMPIXPASA-N 0.000 claims 1
• 239000008351 acetate buffer Substances 0.000 claims 1
• 229940087168 alpha Tocopherol Drugs 0.000 claims 1
• 239000012062 aqueous buffer Substances 0.000 claims 1
• 239000007864 aqueous solution Substances 0.000 claims 1
• 125000004429 atoms Chemical group 0.000 claims 1
• 235000019445 benzyl alcohol Nutrition 0.000 claims 1
• 235000004420 brassicasterol Nutrition 0.000 claims 1
• 235000000431 campesterol Nutrition 0.000 claims 1
• 125000002837 carbocyclic group Chemical group 0.000 claims 1
• 125000004452 carbocyclyl group Chemical group 0.000 claims 1
• 150000001783 ceramides Chemical class 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 claims 1
• 235000012000 cholesterol Nutrition 0.000 claims 1
• 239000007979 citrate buffer Substances 0.000 claims 1
• 150000001982 diacylglycerols Chemical class 0.000 claims 1
• 125000005265 dialkylamine group Chemical class 0.000 claims 1
• 150000001985 dialkylglycerols Chemical class 0.000 claims 1
• 238000000502 dialysis Methods 0.000 claims 1
• DSNRWDQKZIEDDB-CLFAGFIQSA-N dioleoyl phosphatidylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC DSNRWDQKZIEDDB-CLFAGFIQSA-N 0.000 claims 1
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
• 230000002209 hydrophobic Effects 0.000 claims 1
• 238000004255 ion exchange chromatography Methods 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000008363 phosphate buffer Substances 0.000 claims 1
• 150000008103 phosphatidic acids Chemical class 0.000 claims 1
• 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 1
• 230000004962 physiological condition Effects 0.000 claims 1
• 235000015500 sitosterol Nutrition 0.000 claims 1
• 229950005143 sitosterol Drugs 0.000 claims 1
• 159000000000 sodium salts Chemical class 0.000 claims 1
• IUVFCFQZFCOKRC-PDSLQGCUSA-M sodium;[(2R)-2,3-bis[[(E)-octadec-9-enoyl]oxy]propyl] 2,3-dihydroxypropyl phosphate Chemical compound [Na+].CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\CCCCCCCC IUVFCFQZFCOKRC-PDSLQGCUSA-M 0.000 claims 1
• 235000016831 stigmasterol Nutrition 0.000 claims 1
• HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims 1
• 125000003107 substituted aryl group Chemical group 0.000 claims 1
• 229960000984 tocofersolan Drugs 0.000 claims 1
• 230000001131 transforming Effects 0.000 claims 1
• 229940096998 ursolic acid Drugs 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
• 239000002076 α-tocopherol Substances 0.000 claims 1
• 235000004835 α-tocopherol Nutrition 0.000 claims 1
• KZJWDPNRJALLNS-VJSFXXLFSA-N β-Sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims 1