BE511759A

BE511759A -

Info

Publication number: BE511759A
Authority: BE; Belgium
Prior art keywords: sep; erythromycin; broth; antibiotic; growth
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE511759A publication Critical patent/BE511759A/fr

Links

ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 73
230000003115 biocidal Effects 0.000 claims description 65
229960003276 erythromycin Drugs 0.000 claims description 64
230000012010 growth Effects 0.000 claims description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 25
239000011780 sodium chloride Substances 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
239000001963 growth media Substances 0.000 claims description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
238000007792 addition Methods 0.000 claims description 17
241000187747 Streptomyces Species 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 12
BXBSPTIDIMGJNO-PBGWIFDRSA-N (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;hydro Chemical compound Cl.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 BXBSPTIDIMGJNO-PBGWIFDRSA-N 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
239000003208 petroleum Substances 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
150000001720 carbohydrates Chemical class 0.000 claims description 5
238000000862 absorption spectrum Methods 0.000 claims description 4
238000002329 infrared spectrum Methods 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 481
235000010633 broth Nutrition 0.000 description 72
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000243 solution Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 25
229920001817 Agar Polymers 0.000 description 22
235000010419 agar Nutrition 0.000 description 22
239000000049 pigment Substances 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
239000002609 media Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 13
229940072049 amyl acetate Drugs 0.000 description 13
239000000463 material Substances 0.000 description 13
210000004215 spores Anatomy 0.000 description 13
241000206672 Gelidium Species 0.000 description 12
239000002585 base Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000002904 solvent Substances 0.000 description 11
229920002472 Starch Polymers 0.000 description 10
239000008272 agar Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
239000008107 starch Substances 0.000 description 10
238000000605 extraction Methods 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
235000019698 starch Nutrition 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
239000011575 calcium Substances 0.000 description 8
229910052791 calcium Inorganic materials 0.000 description 8
230000018109 developmental process Effects 0.000 description 8
239000002054 inoculum Substances 0.000 description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
235000010469 Glycine max Nutrition 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
235000013339 cereals Nutrition 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000000855 fermentation Methods 0.000 description 7
230000004151 fermentation Effects 0.000 description 7
244000005700 microbiome Species 0.000 description 7
239000000047 product Substances 0.000 description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000008103 glucose Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
238000002791 soaking Methods 0.000 description 6
WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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 6
239000003610 charcoal Substances 0.000 description 5
235000013312 flour Nutrition 0.000 description 5
239000006916 nutrient agar Substances 0.000 description 5
229940064005 Antibiotic throat preparations Drugs 0.000 description 4
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 4
229940042052 Antibiotics for systemic use Drugs 0.000 description 4
229940042786 Antitubercular Antibiotics Drugs 0.000 description 4
229940093922 Gynecological Antibiotics Drugs 0.000 description 4
229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
-1 ammonium ions Chemical class 0.000 description 4
235000014633 carbohydrates Nutrition 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
229940079866 intestinal antibiotics Drugs 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
235000015097 nutrients Nutrition 0.000 description 4
229940005935 ophthalmologic Antibiotics Drugs 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000028070 sporulation Effects 0.000 description 4
239000000758 substrate Substances 0.000 description 4
229940016114 Calcium Malate Drugs 0.000 description 3
OLOZVPHKXALCRI-UHFFFAOYSA-L Calcium malate Chemical compound [Ca+2].[O-]C(=O)C(O)CC([O-])=O OLOZVPHKXALCRI-UHFFFAOYSA-L 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
238000009632 agar plate Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006286 aqueous extract Substances 0.000 description 3
239000001362 calcium malate Substances 0.000 description 3
235000013962 calcium malate Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
230000000875 corresponding Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
230000001747 exhibiting Effects 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
239000002689 soil Substances 0.000 description 3
235000020275 sunflower milk Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
241001446247 uncultured actinomycete Species 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
229960001230 Asparagine Drugs 0.000 description 2
241000972773 Aulopiformes Species 0.000 description 2
241000589562 Brucella Species 0.000 description 2
244000223760 Cinnamomum zeylanicum Species 0.000 description 2
235000004310 Cinnamomum zeylanicum Nutrition 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N D-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
229920001353 Dextrin Polymers 0.000 description 2
239000004375 Dextrin Substances 0.000 description 2
BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 2
240000007842 Glycine max Species 0.000 description 2
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
241000192041 Micrococcus Species 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
241000194017 Streptococcus Species 0.000 description 2
CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 2
241000607598 Vibrio Species 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
230000000844 anti-bacterial Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
235000009582 asparagine Nutrition 0.000 description 2
235000020127 ayran Nutrition 0.000 description 2
238000004166 bioassay Methods 0.000 description 2
238000002815 broth microdilution Methods 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
239000005018 casein Substances 0.000 description 2
235000021240 caseins Nutrition 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
235000017803 cinnamon Nutrition 0.000 description 2
239000006071 cream Substances 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
238000007654 immersion Methods 0.000 description 2
150000002576 ketones Chemical class 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
238000001556 precipitation Methods 0.000 description 2
235000019515 salmon Nutrition 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N 2-Heptanone Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000237519 Bivalvia Species 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N Chlormethine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
206010008631 Cholera Diseases 0.000 description 1
240000009226 Corylus americana Species 0.000 description 1
235000001543 Corylus americana Nutrition 0.000 description 1
235000007466 Corylus avellana Nutrition 0.000 description 1
GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N D-Maltose Chemical compound 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 1
FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 1
WQZGKKKJIJFFOK-SVZMEOIVSA-N D-galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
206010014979 Epidemic typhus Diseases 0.000 description 1
229960002737 Fructose Drugs 0.000 description 1
241000233866 Fungi Species 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
229940093912 Gynecological Sulfonamides Drugs 0.000 description 1
240000006669 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
229940029339 Inulin Drugs 0.000 description 1
229920001202 Inulin Polymers 0.000 description 1
JYJIGFIDKWBXDU-MNNPPOADSA-N Inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
229940045505 Klebsiella pneumoniae Drugs 0.000 description 1
241000588747 Klebsiella pneumoniae Species 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
241000186781 Listeria Species 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229960004961 Mechlorethamine Drugs 0.000 description 1
210000004080 Milk Anatomy 0.000 description 1
241000186367 Mycobacterium avium Species 0.000 description 1
229940010383 Mycobacterium tuberculosis Drugs 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
229940105132 Myristate Drugs 0.000 description 1
241000588653 Neisseria Species 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
229940049964 Oleate Drugs 0.000 description 1
229940049954 Penicillin Drugs 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
229940066779 Peptones Drugs 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
PNNNRSAQSRJVSB-BXKVDMCESA-N 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
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
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 1
210000002966 Serum Anatomy 0.000 description 1
210000003491 Skin Anatomy 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M Sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
WPUMTJGUQUYPIV-UHFFFAOYSA-L Sodium malate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)CC([O-])=O WPUMTJGUQUYPIV-UHFFFAOYSA-L 0.000 description 1
229940074404 Sodium succinate Drugs 0.000 description 1
HELHAJAZNSDZJO-UHFFFAOYSA-L Sodium tartrate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C(O)C([O-])=O HELHAJAZNSDZJO-UHFFFAOYSA-L 0.000 description 1
229960002167 Sodium tartrate Drugs 0.000 description 1
240000001016 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229940076185 Staphylococcus aureus Drugs 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229960005322 Streptomycin Drugs 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K Trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
241000700605 Viruses Species 0.000 description 1
208000001877 Whooping Cough Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N aldehydo-D-arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229940009868 aluminum magnesium silicate Drugs 0.000 description 1
WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
229960000626 benzylpenicillin Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001058 brown pigment Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000020639 clam Nutrition 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052803 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000005824 corn Nutrition 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000005712 crystallization Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L disodium butanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000002223 garnet Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052500 inorganic mineral Chemical class 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 1
230000006799 invasive growth in response to glucose limitation Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001788 irregular Effects 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000035800 maturation Effects 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006011 modification reaction Methods 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
230000000877 morphologic Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-M myristate Chemical compound CCCCCCCCCCCCCC([O-])=O TUNFSRHWOTWDNC-UHFFFAOYSA-M 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000003000 nontoxic Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
201000005702 pertussis Diseases 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000001376 precipitating Effects 0.000 description 1
230000002035 prolonged Effects 0.000 description 1
230000001737 promoting Effects 0.000 description 1
238000007665 sagging Methods 0.000 description 1
229940120668 salicin Drugs 0.000 description 1
238000007790 scraping Methods 0.000 description 1
235000019265 sodium DL-malate Nutrition 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000001394 sodium malate Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic Effects 0.000 description 1
229940026752 topical Sulfonamides Drugs 0.000 description 1
KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical compound Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
239000011778 trisodium citrate Substances 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
238000007817 turbidimetric assay Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
WQZGKKKJIJFFOK-DVKNGEFBSA-N α-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1