CH671674A5 - - Google Patents
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- Publication number
- CH671674A5 CH671674A5 CH5400/85A CH540085A CH671674A5 CH 671674 A5 CH671674 A5 CH 671674A5 CH 5400/85 A CH5400/85 A CH 5400/85A CH 540085 A CH540085 A CH 540085A CH 671674 A5 CH671674 A5 CH 671674A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chamomile
- flowers
- bisabolol
- chamazulen
- bisaboloids
- Prior art date
Links
- 244000042664 Matricaria chamomilla Species 0.000 claims description 122
- 235000007232 Matricaria chamomilla Nutrition 0.000 claims description 112
- 235000007866 Chamaemelum nobile Nutrition 0.000 claims description 103
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical compound CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 97
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 claims description 93
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 claims description 93
- 241000196324 Embryophyta Species 0.000 claims description 92
- DBZHHRPNWDNKNX-UHFFFAOYSA-N Chamazulen Natural products CC1=CC=C2C=C(C=CC(=C12)C(C)C)C DBZHHRPNWDNKNX-UHFFFAOYSA-N 0.000 claims description 82
- 229940079593 drug Drugs 0.000 claims description 59
- 239000003814 drug Substances 0.000 claims description 59
- 239000000341 volatile oil Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 34
- 208000035199 Tetraploidy Diseases 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 25
- 229940036350 bisabolol Drugs 0.000 claims description 24
- 229910001868 water Inorganic materials 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 18
- PMRJYBALQVLLSJ-UHFFFAOYSA-N chamazulene Natural products CCC1=CC2=C(C)CCC2=CC=C1 PMRJYBALQVLLSJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 15
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 claims description 14
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 claims description 14
- 239000012675 alcoholic extract Substances 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 11
- 230000001476 alcoholic effect Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 235000020221 chamomile extract Nutrition 0.000 claims description 7
- 238000010367 cloning Methods 0.000 claims description 7
- 206010020649 Hyperkeratosis Diseases 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 229940119217 chamomile extract Drugs 0.000 claims description 2
- 241000208838 Asteraceae Species 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000001035 drying Methods 0.000 description 41
- 238000003306 harvesting Methods 0.000 description 22
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 238000005520 cutting process Methods 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 229940070641 chamomile flowers Drugs 0.000 description 10
- 210000000349 chromosome Anatomy 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- 229960001338 colchicine Drugs 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000009331 sowing Methods 0.000 description 9
- 229930189957 Bisabolol oxide Natural products 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000010628 chamomile oil Substances 0.000 description 6
- 235000019480 chamomile oil Nutrition 0.000 description 6
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- SYTRJRUSWMMZLV-UHFFFAOYSA-N 4-epimatricin Natural products C1=CC(O)(C)C2C1=C(C)CC(OC(C)=O)C1C2OC(=O)C1C SYTRJRUSWMMZLV-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SYTRJRUSWMMZLV-VQGWEXQJSA-N Matricin Chemical compound [C@@H]1([C@H](CC(C)=C2[C@@H]3[C@](C=C2)(C)O)OC(C)=O)[C@@H]3OC(=O)[C@H]1C SYTRJRUSWMMZLV-VQGWEXQJSA-N 0.000 description 4
- SYTRJRUSWMMZLV-AHWDLOTJSA-N Matricin Natural products O=C(O[C@@H]1[C@H]2[C@H](C)C(=O)O[C@@H]2[C@H]2[C@](O)(C)C=CC2=C(C)C1)C SYTRJRUSWMMZLV-AHWDLOTJSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000010154 cross-pollination Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000000644 propagated effect Effects 0.000 description 4
- 210000001082 somatic cell Anatomy 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WJHRAVIQWFQMKF-UHFFFAOYSA-N Bisabolol oxide A Natural products C1CC(C)=CCC1C1(C)OC(C)(C)C(O)CC1 WJHRAVIQWFQMKF-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KMJLGCYDCCCRHH-UHFFFAOYSA-N Spathulenol Natural products CC1(O)CCC2(C)C1C3C(CCC2=C)C3(C)C KMJLGCYDCCCRHH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FRMCCTDTYSRUBE-HYFYGGESSA-N ent-spathulenol Chemical compound C1CC(=C)[C@H]2CC[C@@](C)(O)[C@@H]2[C@H]2C(C)(C)[C@H]21 FRMCCTDTYSRUBE-HYFYGGESSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- -1 spiro ethers Chemical class 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- XZRVRYFILCSYSP-OAHLLOKOSA-N (-)-beta-bisabolene Chemical compound CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1 XZRVRYFILCSYSP-OAHLLOKOSA-N 0.000 description 2
- KNOUERLLBMJGLF-UHFFFAOYSA-N 1-bisabolone Natural products CC(C)=CCCC(C)C1CCC(C)=CC1=O KNOUERLLBMJGLF-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- RKBAYVATPNYHLW-NFAWXSAZSA-N Bisabolol oxide B Natural products OC(C)(C)[C@@H]1O[C@](C)([C@@H]2CC=C(C)CC2)CC1 RKBAYVATPNYHLW-NFAWXSAZSA-N 0.000 description 2
- RKBAYVATPNYHLW-UHFFFAOYSA-N Bisabolol oxide B Chemical compound C1CC(C)=CCC1C1(C)OC(C(C)(C)O)CC1 RKBAYVATPNYHLW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 239000007836 KH2PO4 Substances 0.000 description 2
- HYVABZIGRDEKCD-UHFFFAOYSA-N N(6)-dimethylallyladenine Chemical compound CC(C)=CCNC1=NC=NC2=C1N=CN2 HYVABZIGRDEKCD-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- YSNRTFFURISHOU-UHFFFAOYSA-N beta-farnesene Natural products C=CC(C)CCC=C(C)CCC=C(C)C YSNRTFFURISHOU-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009402 cross-breeding Methods 0.000 description 2
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 2
- 239000004062 cytokinin Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000008124 floral development Effects 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000003864 humus Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- WQJFIWXYPKYBTO-UHFFFAOYSA-N indole-1-acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1 WQJFIWXYPKYBTO-UHFFFAOYSA-N 0.000 description 2
- 239000003617 indole-3-acetic acid Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 229960000367 inositol Drugs 0.000 description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 2
- 230000011278 mitosis Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
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- 239000011664 nicotinic acid Substances 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
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- 239000004945 silicone rubber Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 2
- 229960003495 thiamine Drugs 0.000 description 2
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- 230000004580 weight loss Effects 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- NGIPHSLFEODPTK-UHFFFAOYSA-N 1,1,1,2,2,3-hexachlorohexane Chemical compound CCCC(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl NGIPHSLFEODPTK-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- KBQRJRIGUDBCTM-UHFFFAOYSA-N 2-(furan-2-ylmethyl)-7h-purin-6-amine Chemical compound N=1C=2N=CNC=2C(N)=NC=1CC1=CC=CO1 KBQRJRIGUDBCTM-UHFFFAOYSA-N 0.000 description 1
- VTDOEFXTVHCAAM-UHFFFAOYSA-N 4-methylpent-3-ene-1,2,3-triol Chemical compound CC(C)=C(O)C(O)CO VTDOEFXTVHCAAM-UHFFFAOYSA-N 0.000 description 1
- QFIIYGZAUXVPSZ-UHFFFAOYSA-N 8-(2,4-dihydroxy-6-methylanilino)-2-(2,4-dihydroxy-6-methylphenyl)imino-7-hydroxy-1,9-dimethyldibenzofuran-3-one Chemical compound CC1=CC(=CC(=C1NC2=C(C3=C(C=C2O)OC4=CC(=O)C(=NC5=C(C=C(C=C5C)O)O)C(=C43)C)C)O)O QFIIYGZAUXVPSZ-UHFFFAOYSA-N 0.000 description 1
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- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
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- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- FCEXWTOTHXCQCQ-UHFFFAOYSA-N Ethoxydihydrosanguinarine Natural products C12=CC=C3OCOC3=C2C(OCC)N(C)C(C2=C3)=C1C=CC2=CC1=C3OCO1 FCEXWTOTHXCQCQ-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 235000004429 Matricaria chamomilla var recutita Nutrition 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004218 Orcein Substances 0.000 description 1
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- 239000006004 Quartz sand Substances 0.000 description 1
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- UWGBIKPRXRSRNM-UHFFFAOYSA-N cevadine Natural products CC=C(C)/C(=O)OC1CCC2(C)C3CCC4C5(O)CC(O)C6(O)C(CN7CC(C)CCC7C6(C)O)C5(O)CC24OCC13O UWGBIKPRXRSRNM-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- HULMNSIAKWANQO-JQKSAQOKSA-N convallatoxin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(C=O)CC1 HULMNSIAKWANQO-JQKSAQOKSA-N 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000012297 crystallization seed Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 1
- ZHCJUZJGMJDUKJ-UHFFFAOYSA-M ethyl(phosphonatooxy)mercury;hydron Chemical compound CC[Hg+].OP(O)([O-])=O ZHCJUZJGMJDUKJ-UHFFFAOYSA-M 0.000 description 1
- QWUGXIXRFGEYBD-UHFFFAOYSA-M ethylmercuric chloride Chemical compound CC[Hg]Cl QWUGXIXRFGEYBD-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 230000000442 meristematic effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- MSYUMXXVCSLXMR-UHFFFAOYSA-N phenylmercury;hydrate Chemical compound O.[Hg]C1=CC=CC=C1 MSYUMXXVCSLXMR-UHFFFAOYSA-N 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 238000001303 quality assessment method Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940084560 sanguinarine Drugs 0.000 description 1
- YZRQUTZNTDAYPJ-UHFFFAOYSA-N sanguinarine pseudobase Natural products C1=C2OCOC2=CC2=C3N(C)C(O)C4=C(OCO5)C5=CC=C4C3=CC=C21 YZRQUTZNTDAYPJ-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930009674 sesquiterpene lactone Natural products 0.000 description 1
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/02—Flowers
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
- A01H6/14—Asteraceae or Compositae, e.g. safflower, sunflower, artichoke or lettuce
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physiology (AREA)
- Botany (AREA)
- Developmental Biology & Embryology (AREA)
- Environmental Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Medicines Containing Plant Substances (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3446216 | 1984-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH671674A5 true CH671674A5 (enrdf_load_stackoverflow) | 1989-09-29 |
Family
ID=6253137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5400/85A CH671674A5 (enrdf_load_stackoverflow) | 1984-12-19 | 1985-12-18 |
Country Status (16)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3446217C2 (de) | 1984-12-19 | 1994-05-19 | Degussa | Verfahren zur Herstellung eines neuen Mittels mit antiphlogistischer Wirkung |
| US6300370B1 (en) | 1987-02-13 | 2001-10-09 | Asta Medica Aktiengesellschaft | Camomile oils having a high content of natural poly-ynes and process for their preparation |
| DE3885137D1 (de) * | 1987-02-13 | 1993-12-02 | Asta Medica Ag | Kamillenöle mit hohem Gehalt an natürlichen Polyinen und Verfahren zu deren Herstellung. |
| DE3806210A1 (de) * | 1988-02-26 | 1989-09-07 | Robugen Gmbh | Kamille |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH489990A (fr) * | 1967-12-15 | 1970-05-15 | Sparano Ottorino | Procédé de traitement par irradiation des graines de plantes terrestres |
| DE2402802C3 (de) * | 1974-01-22 | 1979-06-13 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Gewinnung einer Kamillendroge mit hohem Chamazulen- und Bisabololgehalt |
| DE2434338A1 (de) * | 1974-07-17 | 1976-01-29 | Degussa | Verfahren zur gewinnung einer kamillendroge mit hohem chamazulen- und bisabololgehalt |
| GB1560371A (en) * | 1978-03-17 | 1980-02-06 | Degussa | Process for obtaining a camomile drug |
| DE3105557A1 (de) * | 1981-02-16 | 1982-09-09 | Henkel Kgaa | "verfahren zur gewinnung von inhaltsstoffen der kamille durch extraktion mit kohlendioxid" |
| IT1157945B (it) * | 1982-06-02 | 1987-02-18 | Bonomelli Spa | Composizione terapeutica ad attivita' antibatterica a base di una frazione estratta da fiori di camomilla e processo per la preparazione di detta frazione |
| IT1177840B (it) * | 1983-06-29 | 1987-08-26 | Degussa | Procedimento per la produzione di una camomilla |
| DE3423207C3 (de) * | 1983-06-29 | 1996-09-26 | Asta Medica Ag | Verfahren zur Herstellung einer neuen Kamillensorte (Bezeichnung Manzana) |
| IN163594B (enrdf_load_stackoverflow) * | 1984-03-16 | 1988-10-15 | Degussa |
-
1985
- 1985-12-04 DE DE3542756A patent/DE3542756C3/de not_active Expired - Lifetime
- 1985-12-12 FR FR858518396A patent/FR2574621B1/fr not_active Expired
- 1985-12-13 NZ NZ214552A patent/NZ214552A/xx unknown
- 1985-12-16 JP JP60281269A patent/JPS61146132A/ja active Pending
- 1985-12-16 EG EG79685A patent/EG17654A/xx active
- 1985-12-17 IT IT8548943A patent/IT1208724B/it active
- 1985-12-18 CH CH5400/85A patent/CH671674A5/de not_active IP Right Cessation
- 1985-12-18 SK SK9445-85A patent/SK280689B6/sk unknown
- 1985-12-18 ES ES550093A patent/ES8702113A1/es not_active Expired
- 1985-12-18 ZA ZA859667A patent/ZA859667B/xx unknown
- 1985-12-18 CZ CS859445A patent/CZ280274B6/cs not_active IP Right Cessation
- 1985-12-18 PL PL85256902A patent/PL164481B1/pl not_active IP Right Cessation
- 1985-12-18 NL NL8503481A patent/NL8503481A/nl active Search and Examination
- 1985-12-18 HU HU854853A patent/HU202034B/hu unknown
- 1985-12-18 ES ES550090A patent/ES8702112A1/es not_active Expired
- 1985-12-18 GR GR853074A patent/GR853074B/el not_active IP Right Cessation
- 1985-12-19 GB GB8531273A patent/GB2170404B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CZ280274B6 (cs) | 1995-12-13 |
| GR853074B (enrdf_load_stackoverflow) | 1986-04-21 |
| EG17654A (en) | 1994-09-29 |
| HUT42671A (en) | 1987-08-28 |
| IT1208724B (it) | 1989-07-10 |
| NL8503481A (nl) | 1986-07-16 |
| CZ944585A3 (en) | 1995-08-16 |
| GB2170404A (en) | 1986-08-06 |
| SK944585A3 (en) | 2000-06-12 |
| ES8702112A1 (es) | 1987-01-01 |
| ES8702113A1 (es) | 1986-12-16 |
| GB2170404B (en) | 1989-09-06 |
| PL256902A1 (en) | 1987-03-09 |
| GB8531273D0 (en) | 1986-01-29 |
| SK280689B6 (sk) | 2000-06-12 |
| NZ214552A (en) | 1989-10-27 |
| IT8548943A0 (it) | 1985-12-17 |
| DE3542756C2 (enrdf_load_stackoverflow) | 1988-02-11 |
| DE3542756A1 (de) | 1986-06-26 |
| ES550093A0 (es) | 1986-12-16 |
| ZA859667B (en) | 1986-08-27 |
| ES550090A0 (es) | 1987-01-01 |
| PL164481B1 (en) | 1994-08-31 |
| HU202034B (en) | 1991-02-28 |
| JPS61146132A (ja) | 1986-07-03 |
| FR2574621A1 (fr) | 1986-06-20 |
| FR2574621B1 (fr) | 1989-08-04 |
| DE3542756C3 (de) | 1997-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: ASTA PHARMA AKTIENGESELLSCHAFT TRANSFER- VIATRIS G |
|
| PL | Patent ceased |