JPS61170396A

JPS61170396A - 新規な制癌性抗生物質８３−１６−ａおよびその製造法

新規な制癌性抗生物質８３−１６−ａおよびその製造法

Info

Publication number: JPS61170396A
Authority: JP; Japan
Prior art keywords: antibiotic; reaction; methanol; culture; substance
Prior art date: 1985-01-25
Legal status : Granted

Application number

JP60011101A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0425950B2 (enrdf_load_stackoverflow

Inventor

Hiroki Komiyama

寛機小宮山

Shinji Funayama

信次船山

Iwao Umezawa

梅沢　巖

Current Assignee

Kitasato Institute

Original Assignee

Kitasato Institute

Priority date

1985-01-25

Filing date

1985-01-25

Publication date

1986-08-01

1985-01-25 Application filed by Kitasato Institute filed Critical Kitasato Institute

1985-01-25 Priority to JP60011101A priority Critical patent/JPS61170396A/ja

1986-01-24 Priority to EP86300498A priority patent/EP0189330B1/en

1986-01-24 Priority to DE8686300498T priority patent/DE3687170T2/de

1986-01-27 Priority to US06/822,820 priority patent/US5109133A/en

1986-08-01 Publication of JPS61170396A publication Critical patent/JPS61170396A/ja

1992-05-06 Publication of JPH0425950B2 publication Critical patent/JPH0425950B2/ja

Status Granted legal-status Critical Current

Links

239000000126 substance Substances 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title abstract 2
239000003972 antineoplastic antibiotic Substances 0.000 title description 3
230000003115 biocidal effect Effects 0.000 claims abstract description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 12
241000187747 Streptomyces Species 0.000 claims abstract description 9
230000002378 acidificating effect Effects 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 6
238000001819 mass spectrum Methods 0.000 claims abstract description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 3
239000011630 iodine Substances 0.000 claims abstract description 3
229910052740 iodine Inorganic materials 0.000 claims abstract description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 3
238000002844 melting Methods 0.000 claims abstract description 3
230000008018 melting Effects 0.000 claims abstract description 3
230000007935 neutral effect Effects 0.000 claims abstract description 3
239000000843 powder Substances 0.000 claims abstract description 3
241000187180 Streptomyces sp. Species 0.000 claims abstract 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims abstract 2
239000003242 anti bacterial agent Substances 0.000 claims description 15
229940088710 antibiotic agent Drugs 0.000 claims description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
241000894006 Bacteria Species 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
238000000862 absorption spectrum Methods 0.000 claims description 6
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
238000003795 desorption Methods 0.000 claims 1
238000012258 culturing Methods 0.000 abstract description 5
238000005273 aeration Methods 0.000 abstract description 4
238000013019 agitation Methods 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
230000000813 microbial effect Effects 0.000 abstract description 2
230000003327 cancerostatic effect Effects 0.000 abstract 1
238000002845 discoloration Methods 0.000 abstract 1
238000000434 field desorption mass spectrometry Methods 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
239000002609 medium Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
230000002829 reductive effect Effects 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
239000000706 filtrate Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 7
229920001817 Agar Polymers 0.000 description 6
239000001888 Peptone Substances 0.000 description 6
108010080698 Peptones Proteins 0.000 description 6
239000008272 agar Substances 0.000 description 6
235000019319 peptone Nutrition 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
241000233866 Fungi Species 0.000 description 5
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
230000000843 anti-fungal effect Effects 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012046 mixed solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000012010 growth Effects 0.000 description 4
WWUVMHRJRCRFSL-UOZMSBJPSA-N Ansatrienin A Chemical compound N([C@H](C)C(=O)O[C@@H]1[C@H](C)[C@@H](O)\C(C)=C/CCC2=CC(=O)C=C(C2=O)NC(=O)C[C@H](/C=C/C=C/C=C/C1)OC)C(=O)C1CCCCC1 WWUVMHRJRCRFSL-UOZMSBJPSA-N 0.000 description 3
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 description 3
206010028980 Neoplasm Diseases 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
230000015271 coagulation Effects 0.000 description 3
238000005345 coagulation Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000035772 mutation Effects 0.000 description 3
WWUVMHRJRCRFSL-UHFFFAOYSA-N mycotrienin I Natural products C1C=CC=CC=CC(OC)CC(=O)NC(C2=O)=CC(=O)C=C2CCC=C(C)C(O)C(C)C1OC(=O)C(C)NC(=O)C1CCCCC1 WWUVMHRJRCRFSL-UHFFFAOYSA-N 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
235000020183 skimmed milk Nutrition 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
241000186361 Actinobacteria <class> Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000192125 Firmicutes Species 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
VVJDHJZQBGWPEQ-NXBJUTJHSA-N [(4e,6r,7s,8s,10e,12e,14e,16r)-6,22,24-trihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(23),4,10,12,14,20(24),21-heptaen-8-yl] (2r)-2-(cyclohexanecarbonylamino)propanoate Chemical compound N([C@H](C)C(=O)O[C@@H]1[C@@H](C)[C@@H](O)/C(C)=C/CCC=2C=C(O)C=C(C=2O)NC(=O)C[C@H](/C=C/C=C/C=C/C1)OC)C(=O)C1CCCCC1 VVJDHJZQBGWPEQ-NXBJUTJHSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
230000001028 anti-proliverative effect Effects 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
230000022534 cell killing Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000012043 crude product Substances 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000009630 liquid culture Methods 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000049 pigment Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-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
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241000544912 Melanoides Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000192041 Micrococcus Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101100327796 Penaeus monodon CHH4 gene Proteins 0.000 description 1
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
241000235527 Rhizopus Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
208000006268 Sarcoma 180 Diseases 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
108010073771 Soybean Proteins Proteins 0.000 description 1
MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
-1 ansatrienin 12 Chemical compound 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
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
230000010261 cell growth Effects 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
230000000445 cytocidal effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052588 hydroxylapatite Inorganic materials 0.000 description 1
239000000411 inducer Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
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 1
229960000367 inositol Drugs 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
239000005453 ketone based solvent Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
239000011785 micronutrient Substances 0.000 description 1
235000013369 micronutrients Nutrition 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
229930190950 mycotrienin Natural products 0.000 description 1
VVJDHJZQBGWPEQ-UHFFFAOYSA-N mycotrienin II Natural products C1C=CC=CC=CC(OC)CC(=O)NC(C=2O)=CC(O)=CC=2CCC=C(C)C(O)C(C)C1OC(=O)C(C)NC(=O)C1CCCCC1 VVJDHJZQBGWPEQ-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
229940001941 soy protein Drugs 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
230000035924 thermogenesis Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1