JPS6217599B2 - - Google Patents
Info
- Publication number
- JPS6217599B2 JPS6217599B2 JP54056587A JP5658779A JPS6217599B2 JP S6217599 B2 JPS6217599 B2 JP S6217599B2 JP 54056587 A JP54056587 A JP 54056587A JP 5658779 A JP5658779 A JP 5658779A JP S6217599 B2 JPS6217599 B2 JP S6217599B2
- Authority
- JP
- Japan
- Prior art keywords
- herbicidin
- substance
- methanol
- substances
- culture
- 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.)
- Expired
Links
- 239000000126 substance Substances 0.000 claims description 50
- XESRQBQRNHDVKD-UHFFFAOYSA-N Herbicidin C Natural products COC1C(O)C(OC2CC3OC(C(O)C3OC12O)n4cnc5c(N)ncnc45)C(=O)O XESRQBQRNHDVKD-UHFFFAOYSA-N 0.000 claims description 37
- DIGRAKJXHSMXBZ-UHFFFAOYSA-N Herbicidin E Natural products C1=NC2=C(N)N=CN=C2N1C1OC2CC(OC(C(O)C3OC(=O)C(C)C)C(=O)OC)C3(O)OC2C1OC DIGRAKJXHSMXBZ-UHFFFAOYSA-N 0.000 claims description 30
- PXURTMJWRXVZEJ-UHFFFAOYSA-N Herbicidin F Natural products C1=NC2=C(N)N=CN=C2N1C1OC2CC(OC(C(O)C3OC(=O)C(C)=CC)C(=O)OC)C3(O)OC2C1OC PXURTMJWRXVZEJ-UHFFFAOYSA-N 0.000 claims description 30
- ODEIJYDLVZTHFG-UHFFFAOYSA-N Herbicidin G Natural products C1=NC2=C(N)N=CN=C2N1C1OC2CC3OC(C(O)=O)C(O)C(OC(=O)C(C)=CC)C3(O)OC2C1O ODEIJYDLVZTHFG-UHFFFAOYSA-N 0.000 claims description 27
- 241000187747 Streptomyces Species 0.000 claims description 10
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- -1 1- Methyl-1-propenylcarbonyl Chemical group 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 125000004677 1-methylethylcarbonyl group Chemical group CC(C)C(=O)* 0.000 claims description 2
- 229930186457 Herbicidin Natural products 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 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 7
- 239000008103 glucose Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- PXURTMJWRXVZEJ-SYDSVXEMSA-N herbicidin f Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]1O[C@@H]2C[C@@H](O[C@@H]([C@@H](O)[C@@H]3OC(=O)C(\C)=C\C)C(=O)OC)[C@@]3(O)O[C@@H]2[C@H]1OC PXURTMJWRXVZEJ-SYDSVXEMSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LOWKANMKNQBRPJ-BMKNLYQISA-N Herbicidin A Natural products CO[C@@H]1[C@H]2O[C@]3(O)[C@@H](C[C@H]2O[C@H]1n4cnc5c(N)ncnc45)O[C@@H]([C@@H](O)[C@@H]3OC(=O)C(=CC)CO)C(=O)OC LOWKANMKNQBRPJ-BMKNLYQISA-N 0.000 description 3
- GZBSICLBZYSADI-UHFFFAOYSA-N Herbicidin B Natural products C1=NC2=C(N)N=CN=C2N1C1OC2CC(OC(C(O)C3O)C(=O)OC)C3(O)OC2C1OC GZBSICLBZYSADI-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- GZBSICLBZYSADI-DHNWSQMASA-N herbicidin b Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]1O[C@@H]2C[C@@H](O[C@@H]([C@@H](O)[C@@H]3O)C(=O)OC)[C@@]3(O)O[C@@H]2[C@H]1OC GZBSICLBZYSADI-DHNWSQMASA-N 0.000 description 3
- LOWKANMKNQBRPJ-MRAUHCMASA-N herbicidin-a Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]1O[C@@H]2C[C@@H](O[C@@H]([C@@H](O)[C@@H]3OC(=O)C(\CO)=C\C)C(=O)OC)[C@@]3(O)O[C@@H]2[C@H]1OC LOWKANMKNQBRPJ-MRAUHCMASA-N 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000002353 algacidal effect Effects 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N deuterated acetone Substances [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 239000003269 fluorescent indicator Substances 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 241000223602 Alternaria alternata Species 0.000 description 1
- 241000532370 Atla Species 0.000 description 1
- 239000004130 Ferrous hexacyanomanganate Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241001279361 Stachybotrys Species 0.000 description 1
- 241001279364 Stachybotrys chartarum Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 description 1
- 241000192589 Synechococcus elongatus PCC 7942 Species 0.000 description 1
- 241000042002 Trametes sanguinea Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003619 algicide Substances 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
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000004407 iron oxides and hydroxides Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compounds Of Unknown Constitution (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5658779A JPS55149297A (en) | 1979-05-09 | 1979-05-09 | Antibiotic herbicidin c, e, f, and g and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5658779A JPS55149297A (en) | 1979-05-09 | 1979-05-09 | Antibiotic herbicidin c, e, f, and g and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55149297A JPS55149297A (en) | 1980-11-20 |
| JPS6217599B2 true JPS6217599B2 (no) | 1987-04-18 |
Family
ID=13031304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5658779A Granted JPS55149297A (en) | 1979-05-09 | 1979-05-09 | Antibiotic herbicidin c, e, f, and g and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55149297A (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108048490A (zh) * | 2017-12-20 | 2018-05-18 | 无锡市拜沃特环保科技有限公司 | 一种链霉菌溶藻活性物质提取方法 |
| CN113337553B (zh) * | 2019-05-31 | 2022-10-21 | 中国医学科学院医药生物技术研究所 | Herbicidin生物合成基因簇及其应用 |
-
1979
- 1979-05-09 JP JP5658779A patent/JPS55149297A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55149297A (en) | 1980-11-20 |
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