JPH037360B2 - - Google Patents
Info
- Publication number
- JPH037360B2 JPH037360B2 JP2381381A JP2381381A JPH037360B2 JP H037360 B2 JPH037360 B2 JP H037360B2 JP 2381381 A JP2381381 A JP 2381381A JP 2381381 A JP2381381 A JP 2381381A JP H037360 B2 JPH037360 B2 JP H037360B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrogallol
- gallic acid
- citrobacter
- medium
- acid
- 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
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 50
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 28
- 229940079877 pyrogallol Drugs 0.000 claims description 25
- 229940074391 gallic acid Drugs 0.000 claims description 14
- 235000004515 gallic acid Nutrition 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 229920001864 tannin Polymers 0.000 claims description 11
- 235000018553 tannin Nutrition 0.000 claims description 11
- 239000001648 tannin Substances 0.000 claims description 11
- 241000588923 Citrobacter Species 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 description 14
- 244000005700 microbiome Species 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 235000013372 meat Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Chinese gallotannin Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 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
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 229920002824 gallotannin Polymers 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- NGFMICBWJRZIBI-JZRPKSSGSA-N Salicin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O1)c1c(CO)cccc1 NGFMICBWJRZIBI-JZRPKSSGSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- NGFMICBWJRZIBI-UHFFFAOYSA-N alpha-salicin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000007789 gas Substances 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
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229920001461 hydrolysable tannin Polymers 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000004816 paper chromatography Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- YNCMLFHHXWETLD-UHFFFAOYSA-N pyocyanin Chemical compound CN1C2=CC=CC=C2N=C2C1=CC=CC2=O YNCMLFHHXWETLD-UHFFFAOYSA-N 0.000 description 2
- 229940120668 salicin Drugs 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- ABUKTBFSGLUCCG-YGKCYCOQSA-N (3r)-4-[3-[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy-4,5-dihydroxybenzoyl]oxy-1-hydroxy-3,5-bis[(3,4,5-trihydroxybenzoyl)oxy]cyclohexane-1-carboxylic acid Chemical compound C([C@H](C1OC(=O)C=2C=C(OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)C(O)=C(O)C=2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(C(=O)O)(O)CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 ABUKTBFSGLUCCG-YGKCYCOQSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 102000000634 Cytochrome c oxidase subunit IV Human genes 0.000 description 1
- 108050008072 Cytochrome c oxidase subunit IV Proteins 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 238000003794 Gram staining Methods 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-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
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 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
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 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
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 108091000100 Tyrosine Phenol-Lyase 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
- 108010046334 Urease Proteins 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
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229940075427 peptone,dried Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 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
- NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 108010038851 tannase Proteins 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
本発明は、シトロバクター属に属するピロガロー
ル生産菌又はその菌体処理物を加水分解型タンニ
ン又は没食子酸に作用せしめてピロガロールに変
換せしめ、これを採取するこによりなるピロガロ
ールの製法に関する。
ピロガロールは、抗酸化剤としてよく知られて
おり、工業薬品、医薬品、分析用試薬等に広く使
用され、安価に供給されるならば工業薬品の中間
体としても期待される化合物である。
微生物によるピロガロールの生産については、
従来、ペニシリウム属(Penicillium)のカビを
使用して、タネンバウムらが糖からの生成
(Biochem.Biophys.Acta.28 21(1958))を、西羅
寛がガロタンニンからの生成(科学26 42(1959))
を報告しているが、いずれもピロガロールを確認
しているのみであり、収量は記載されていない。
本発明者等は、ピロガロールを工業的に容易か
つ安価に製造する方法について鋭意研究を行つて
いたところ、京都市の土壞から分離した菌株がタ
ンニン等からピロガロールを生産することを見出
し、さらに研究を進めて本発明を完成した。
本菌株は工業技術院微生物工業技術研究所に微
生物受託番号微工研菌寄第5874号として寄託して
おりその菌学的性質は次のとおりである。
(a) 形態
細胞の形及び大きさ:0.5〜2.0×1.5〜6.0μ
m
細胞の多形性の有無:なし
運動性の有無:20℃で活発に運動する。周
鞭毛
胞子の有無:なし
グラム染色性:陰性
抗酸性:なし
(b) 各培地における生育状態
肉汁寒天平板培養:速やかに生育しコロニ
ーはうすいクリーム色で粘稠性がある。
肉汁寒天斜面培養:生育普通。直線状に生
育し表面平滑である。培地は変化しない。
肉汁液体培養:混濁状によく生育する。表
面の発育大
肉汁ゼラチン穿刺培養:ゼラチンの液化を
認めない。菌は表面に固まつてリング状に生
育する。
リトマス・ミルク:表面から5mmを除きリ
トマスは還元され、ミルクは凝固する(48時
間後)。1週間後全体が白く凝固する。
ブリリアントグリーン培地での生育:よく
発育し4日目に黄変する。
(c) 生理学的性質
硝酸塩還元:+
脱窒反応:−
MRテスト:+
VPテスト:−
インドールの生成:−
硫化水素の生成:−
デンプンの加水分解:−
クエン酸の利用:+
無機窒素源の利用:+
色素の生成:−
ウレアーゼ:−
オキシダーゼ:−
カタラーゼ:+
生育の範囲:PH6〜7、至適温度28℃
酸素に対する態度:通性嫌気性
O−Fテスト:ダルシトール、フラクトー
ス、ガラクトース、グルコース、マルトー
ス、マンニトール、メリビオース、サリシ
ン、シユークロース、キシロースを発酵的に
分解する。
糖類から酸及びガスの生成:
酸の生成 ガスの生
成
アドニール − −
L−アラビノース − −
ダルシトール + −
D−フラクトース + +
D−ガラクトース + +
D−グルコース + +
グリコーゲン − −
イノシツト − −
イヌリン − −
ラクトース − −
マルトース + +
D−マンニトール + +
メリビオース ± −
サリシン + +
D−ソルビトース − −
L−ソルボース − −
シユークロース + +
ラフイノース − −
D−キシロース + +
デンプン − −
(d) その他
チトクロムオキシダーゼ:−
DNase:−
β−チロシナーゼ:−
リジン脱炭酸反応:±
フエニルアラニンアミナーゼ:−
シアン化カリ耐性:+
塩化ナトリウム耐性:7.5%NaCl中でよく生育
する。
King A培地でピオシアニンを生産しない:
シユードモナス属(Pseudomonas)でない。
King B培地で螢光色素を生産しない:
シユードモナス属(Pseudomonas)でない。
上記の菌学的性質をBergey's Mannual of
Determinative Bacteriology 8th ed,(1974)
と対比検討した結果、本菌株はシトロバクター・
フロインデイに属するものと判定されたが、硫化
水素の生成及びインドールの生成が陰性である点
が標準とは異なるので新菌株と認め、シトロバク
ター・フロインデイ26−19と命名した。シトロバ
クター属に属する微生物がピロガロールを生成す
ることは従来報告されていない。
本発明によるピロガロールの製法においては、
土壞から分離した微生物をそのまま使用してもよ
いし、変異により誘導された高力価ピガロール生
産菌を用いてもよい。変異手段は紫外線、放射線
等の照射やN−メチル−N′−ニトロ−N−ニト
ロアニジン処理などの通常の方法による。
加水分解型タンニン又は没食子酸に本微生物又
はその菌体処理物を作用せしめるには(1)本微生物
を加水分解型タンニン又は没食子酸を含む培地で
培養するか、又は(2)予め培養した本微生物の菌体
をそのまま又はその菌体を処理した後、適当な液
体中で加水分解型タンニン又は没食子酸と接触せ
しめる。なお、加水分解型タンニンは、例えばガ
ロタンニン、五倍子タンニン、没食子タンニン、
タラタンニンである。
前記の方法(1)を用いる場合、倍地は通常の炭素
源、窒素源、無機塩以外に加水分解型タンニン又
は没食子酸を含むものを用いる。炭素源として
は、グルコース、ガラクトース、マルトース、マ
ンニトール、シユークロース、キシロース、グリ
セリン、キナ酸などが適宜用いられる。窒素源と
して、肉エキス、ペプトン、乾燥酵母、酵母エキ
ス、コーンスチープリカーや無機窒素(例えば硫
酸アンモニウム、塩化アンモニウム、硝酸ナトリ
ウム、硝酸アンモニウム)などが用いられる。無
機塩としては、リン酸カリウム、塩化カリウム、
塩化ナトリウム、炭酸カルシウム、硫酸マグネシ
ウム、硫酸鉄などが用いられる。更に微量栄養源
としてビタミン類、核酸塩基類、アミノ酸類を適
宜添加してもよい。
培養は、振とう、静置のいずれでもよいが、好
気的条件下に温度15〜30℃、PH約5〜10で、約10
〜240時間行うのが好ましい。
一方、前記の方法(2)を用いるときは、加水分解
型タンニン又は没食子酸と菌体又は菌体処理物を
水又は緩衝液に溶解又は懸濁して10〜70℃で静置
するか又は撹拌しながら反応させる。菌体又は菌
体処理物は培養液から単離して用いても、単離せ
ずに用いてもよい。
菌体を得る方法は前記(1)の倍地及び培養方法が
そのまま採用できる。本微生物はタンニン類を含
まない培地でも十分生育するが、該物質を小量添
加すると、これらの物質をピロガロールに変換す
る活性のより高い菌体が得られる場合がある。
菌体処理物としては、機械的摩砕菌体、超音波
処理菌体、凍結乾燥菌体、アセトン乾燥菌体、界
面活性剤若しくは有機溶媒処理菌体又はこれらの
処理通常の酸素分離法を用いて分取したタンナー
ゼ及び没食子酸脱炭酸酵素等が適宜用いられる。
更に、菌体又は酵素を固定化して連続的にピロガ
ロールを生産させることもできる。
ピロガロールの生成はペーパークロマトグラフ
イー、薄層クロマトグラフイー、高速液体クロマ
トグラフイーで確認でき、硫酸バニリン法
(Swani T;J.Sci.Food Agr.10,63(1959))に
より定量し得るので、ピロガロール蓄積量がほと
んど増加しなくなつた時点で生産を終了すればよ
い。
蓄積したピロガロールは、ジエチルエーテル抽
出し、活性炭などで脱色し、濃縮し、昇華する方
法等により単離することができる。
次に、実施例をあげて本発明を更に詳細に説明
する。
実施例 1
ガロタンヒン又はタラタンニン1%、硝酸ナト
リウム0.2%、リン酸二水素カリウム0.1%、硫酸
マグネシウム0.05%、塩化カリウム0.05%よりな
る液体培地(PH6.0)5mlを入れた綿栓付試験管
2本にシトロバクター・フロインデイ26−19株を
1白金耳接種し、28℃、24時間振とう培養した。
全体を上記と同一組成のタンニン液体培地500ml
に接種し、28℃で静置培養した。ピロガロールの
生成量は以下の通りであつた。
The present invention relates to a method for producing pyrogallol, which comprises converting a pyrogallol-producing bacterium belonging to the genus Citrobacter or a processed product thereof into pyrogallol by reacting it with hydrolyzed tannin or gallic acid, and collecting the resulting product. Pyrogallol is well known as an antioxidant and is widely used in industrial chemicals, pharmaceuticals, analytical reagents, etc., and is a compound that is expected to be used as an intermediate for industrial chemicals if it can be supplied at low cost. Regarding the production of pyrogallol by microorganisms,
Conventionally, using molds of the genus Penicillium, Tannenbaum et al. reported the production from sugar (Biochem. ))
However, they only confirm the presence of pyrogallol and do not state the yield. The inventors of the present invention were conducting intensive research on a method for industrially producing pyrogallol easily and inexpensively, and discovered that a strain isolated from a clay pot in Kyoto City produced pyrogallol from tannins, etc. The present invention was completed through further research. This strain has been deposited with the Institute of Microbial Technology, Agency of Industrial Science and Technology under microbial accession number 5874, and its mycological properties are as follows. (a) Morphology Cell shape and size: 0.5-2.0×1.5-6.0μ
m Presence or absence of cell pleomorphism: None Motility: Actively motile at 20°C. Periflagellates Presence of spores: None Gram staining: Negative Acid-fastness: None (b) Growth status in each medium Juicy agar plate culture: Grows quickly, and colonies are pale cream colored and viscous. Meat juice agar slant culture: Normal growth. It grows in a straight line and has a smooth surface. The medium remains unchanged. Meat juice liquid culture: Grows well in a cloudy state. Large surface growth Meat juice gelatin puncture culture: No liquefaction of gelatin observed. Bacteria harden on the surface and grow in a ring shape. Litmus milk: Remove 5 mm from the surface and the litmus will be reduced and the milk will coagulate (after 48 hours). After one week, the whole body becomes white and solidified. Growth on brilliant green medium: It grows well and turns yellow on the 4th day. (c) Physiological properties Nitrate reduction: + Denitrification reaction: - MR test: + VP test: - Indole formation: - Hydrogen sulfide formation: - Starch hydrolysis: - Citric acid utilization: + Inorganic nitrogen source Utilization: + Pigment production: - Urease: - Oxidase: - Catalase: + Growth range: PH6-7, optimum temperature 28°C Attitude towards oxygen: Facultative anaerobic O-F test: Dulcitol, fructose, galactose, glucose Fermentatively degrades maltose, mannitol, melibiose, salicin, sucrose, and xylose. Production of acid and gas from sugars: Production of acid Production of gas Adonyl - - L-arabinose - - Dulcitol + - D-Fructose + + D-Galactose + + D-Glucose + + Glycogen - - Inosit - - Inulin - - Lactose − − Maltose + + D-mannitol + + Melibiose ± − Salicin + + D-sorbitose − − L-sorbose − − Seuculose + + Raffinose − − D-xylose + + Starch − − (d) Other cytochrome oxidase: − DNase: - β-tyrosinase: - Lysine decarboxylation: ± Phenylalanine aminase: - Potassium cyanide tolerance: + Sodium chloride tolerance: Grows well in 7.5% NaCl. Does not produce pyocyanin in King A medium: Not Pseudomonas. Does not produce fluorescent pigment in King B medium: Not Pseudomonas. Bergey's Manual of the above mycological properties
Determinative Bacteriology 8th ed, (1974)
As a result of comparison with Citrobacter
The strain was determined to belong to Citrobacter freundei, but since it differed from the standard in that hydrogen sulfide production and indole production were negative, it was recognized as a new strain and named Citrobacter freundei 26-19. It has not been previously reported that microorganisms belonging to the genus Citrobacter produce pyrogallol. In the method for producing pyrogallol according to the present invention,
The microorganism isolated from the clay pot may be used as it is, or a high-titer pigallol-producing microorganism induced by mutation may be used. The mutation means is carried out by conventional methods such as irradiation with ultraviolet rays, radiation, etc., and treatment with N-methyl-N'-nitro-N-nitroanidine. To cause the present microorganism or its bacterial cell-treated product to act on hydrolyzed tannin or gallic acid, (1) culture the present microorganism in a medium containing hydrolyzed tannin or gallic acid, or (2) use pre-cultured microorganisms. The microorganism cells are brought into contact with hydrolyzed tannin or gallic acid in an appropriate liquid, either as they are or after the cells have been treated. In addition, hydrolyzable tannins include, for example, gallotannins, pentagram tannins, gallic tannins,
It is tartannin. When using the above method (1), the base medium contains hydrolyzable tannin or gallic acid in addition to the usual carbon source, nitrogen source, and inorganic salt. As the carbon source, glucose, galactose, maltose, mannitol, sucrose, xylose, glycerin, quinic acid, etc. are used as appropriate. As a nitrogen source, meat extract, peptone, dried yeast, yeast extract, corn steep liquor, inorganic nitrogen (for example, ammonium sulfate, ammonium chloride, sodium nitrate, ammonium nitrate), etc. are used. Inorganic salts include potassium phosphate, potassium chloride,
Sodium chloride, calcium carbonate, magnesium sulfate, iron sulfate, etc. are used. Furthermore, vitamins, nucleobases, and amino acids may be appropriately added as micronutrient sources. Culture may be carried out by shaking or standing still, but under aerobic conditions at a temperature of 15 to 30°C and a pH of approximately 5 to 10,
It is preferred to carry out for ~240 hours. On the other hand, when using method (2) above, the hydrolyzed tannin or gallic acid and the bacterial cells or the bacterial cell treated product are dissolved or suspended in water or a buffer solution and left standing at 10 to 70°C or stirred. While reacting. The bacterial cells or treated bacterial cells may be used after being isolated from the culture solution, or may be used without being isolated. As a method for obtaining bacterial cells, the medium and culture method described in (1) above can be used as is. Although this microorganism can grow well in a medium that does not contain tannins, adding small amounts of these substances may result in bacterial cells that have a higher activity of converting these substances into pyrogallol. The bacterial cell treatment product includes mechanically ground bacterial cells, ultrasonicated bacterial cells, freeze-dried bacterial cells, acetone-dried bacterial cells, surfactant- or organic solvent-treated bacterial cells, or these treatments using ordinary oxygen separation methods. Tannase, gallic acid decarboxylase, etc., which have been isolated using a method, are used as appropriate.
Furthermore, pyrogallol can be produced continuously by immobilizing bacterial cells or enzymes. The production of pyrogallol can be confirmed by paper chromatography, thin layer chromatography, and high performance liquid chromatography, and can be quantified by the vanillin sulfate method (Swani T; J.Sci.Food Agr. 10, 63 (1959)). Production may be terminated when the accumulated amount of pyrogallol hardly increases. The accumulated pyrogallol can be isolated by extraction with diethyl ether, decolorization with activated carbon, etc., concentration, and sublimation. Next, the present invention will be explained in more detail by giving examples. Example 1 A test tube with a cotton stopper containing 5 ml of a liquid medium (PH6.0) consisting of 1% gallotanhin or taratannin, 0.2% sodium nitrate, 0.1% potassium dihydrogen phosphate, 0.05% magnesium sulfate, and 0.05% potassium chloride. One platinum loop of Citrobacter freundei strain 26-19 was inoculated into two plants, and cultured with shaking at 28°C for 24 hours.
500ml of tannin liquid medium with the same composition as above
The cells were inoculated and cultured statically at 28°C. The amount of pyrogallol produced was as follows.
【表】
実施例 2
実施例1の方法でガロタンニン又はタラタンニ
ン1%の代りに没食子酸0.2%に置き換えた培地
で96時間培養を行つた。その結果、ピロガロール
の生成量は5.67μmol/mlで没食子酸からの転換
率は53.3%であつた。
実施例 3
5mlブイヨン液体培地を入れた5本の綿栓付試
験管にシトロバクター・フロインデイ26−19株を
1白金耳接種し、28℃、24時間振とう培養後、ペ
プトン0.5%、肉エキス0.5%、塩化ナトリウム0.2
%、酵母エキス0.05%、没食子酸0.2%を含む液
体培地500mlに接種し、28℃、24時間静置培養し
た。全体を9000rpmで30分間遠心分離し、沈殿物
を0.05M酢酸緩衝液(PH5.5)に懸濁し、20KCで
3分間超音波破砕した。次いで12000rpmで30分
間遠心分離し、上澄液を粗酵素液とした。別に、
0.4M酢酸ナトリウム−酢酸緩衝液(PH5.5)100
mlに没食子酸2gを溶解した溶液を用意し、上記
粗酵素液10mlを加え、30℃、60分間放置した。30
%硫酸2mlを加えて反応を停止させると、溶液中
のピロガロールは0.94gで没食子酸からの転換率
は63.4%であつた。
実施例 4
実施例1の方法で得た500ml培地のガロタンニ
ン培養液を9000rpmで20分間遠心分離して上清液
500mlを得た。1N塩酸でPH2.0とした後、2回、
500mlのジエチルエーテルで抽出し、エーテル層
を蒸発乾固する。次いで小量の熱水を加えて溶解
し、5℃で2晩放置すると没食子酸の結晶が析出
した。これを過して除き、液を蒸発乾固しデ
シケータ中で乾燥した。乾燥粉末を減圧下昇華管
中に入れ、75℃にて昇華を行い、結晶752mgを得
た。
本結晶の融点は131℃、元素分析値はC:57.14
%、H:4.80%、O:38.06%、ペーパークロマ
トグラフイーのRf値(展開溶媒n−ブタノー
ル:酢酸:水=4:1:1)は0.66であり、IRス
ペクトルはピロガロールのそれと完全に一致し
た。よつて本結晶はピロガロールと同定した。[Table] Example 2 Culture was carried out for 96 hours using the method of Example 1 in a medium in which 1% of gallotannin or taradannin was replaced with 0.2% gallic acid. As a result, the amount of pyrogallol produced was 5.67 μmol/ml, and the conversion rate from gallic acid was 53.3%. Example 3 One platinum loop of Citrobacter freundei strain 26-19 was inoculated into five test tubes with cotton plugs containing 5 ml of bouillon liquid medium, and after cultured with shaking at 28°C for 24 hours, peptone 0.5% and meat extract were added. 0.5%, sodium chloride 0.2
%, yeast extract 0.05%, and gallic acid 0.2%. The whole was centrifuged at 9000 rpm for 30 minutes, and the precipitate was suspended in 0.05M acetate buffer (PH5.5) and sonicated at 20KC for 3 minutes. The mixture was then centrifuged at 12,000 rpm for 30 minutes, and the supernatant was used as a crude enzyme solution. Separately,
0.4M sodium acetate-acetate buffer (PH5.5) 100
A solution in which 2 g of gallic acid was dissolved in 1 ml was prepared, 10 ml of the above crude enzyme solution was added, and the solution was left at 30° C. for 60 minutes. 30
When the reaction was stopped by adding 2 ml of % sulfuric acid, the amount of pyrogallol in the solution was 0.94 g, and the conversion rate from gallic acid was 63.4%. Example 4 500 ml of the gallotannin culture solution obtained by the method of Example 1 was centrifuged at 9000 rpm for 20 minutes to obtain a supernatant liquid.
Obtained 500ml. After adjusting the pH to 2.0 with 1N hydrochloric acid, twice.
Extract with 500 ml of diethyl ether and evaporate the ether layer to dryness. Next, a small amount of hot water was added to dissolve the mixture, and when it was left to stand at 5°C for 2 nights, gallic acid crystals were precipitated. This was removed by filtration and the liquid was evaporated to dryness and dried in a desiccator. The dry powder was placed in a sublimation tube under reduced pressure and sublimated at 75°C to obtain 752 mg of crystals. The melting point of this crystal is 131℃, and the elemental analysis value is C: 57.14
%, H: 4.80%, O: 38.06%, Rf value of paper chromatography (developing solvent n-butanol: acetic acid: water = 4:1:1) is 0.66, and the IR spectrum completely matches that of pyrogallol. did. Therefore, this crystal was identified as pyrogallol.
Claims (1)
菌又はその菌体処理物を加水分解型タンニン又は
没食子酸に作用せしめてピロガロールに変換せし
め、これを採取することを特徴とするピロガロー
ルの製法。 2 シトロバクター属に属するピロガロール生産
菌がシトロバクター・フロインデイ26−19株であ
る特許請求の範囲第1項記載のピロガロールの製
法。[Scope of Claims] 1. A method for producing pyrogallol, which comprises converting a pyrogallol-producing bacterium belonging to the genus Citrobacter or a processed product thereof into pyrogallol by reacting it with hydrolyzed tannin or gallic acid, and collecting the same. . 2. The method for producing pyrogallol according to claim 1, wherein the pyrogallol-producing bacterium belonging to the genus Citrobacter is Citrobacter freundei strain 26-19.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2381381A JPS57138393A (en) | 1981-02-19 | 1981-02-19 | Production of pyrogallol utilizing microorganism |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2381381A JPS57138393A (en) | 1981-02-19 | 1981-02-19 | Production of pyrogallol utilizing microorganism |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57138393A JPS57138393A (en) | 1982-08-26 |
JPH037360B2 true JPH037360B2 (en) | 1991-02-01 |
Family
ID=12120774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2381381A Granted JPS57138393A (en) | 1981-02-19 | 1981-02-19 | Production of pyrogallol utilizing microorganism |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57138393A (en) |
-
1981
- 1981-02-19 JP JP2381381A patent/JPS57138393A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57138393A (en) | 1982-08-26 |
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