GB1064300A - A new antibiotic coumermycin - Google Patents
A new antibiotic coumermycinInfo
- Publication number
- GB1064300A GB1064300A GB4962263A GB4962263A GB1064300A GB 1064300 A GB1064300 A GB 1064300A GB 4962263 A GB4962263 A GB 4962263A GB 4962263 A GB4962263 A GB 4962263A GB 1064300 A GB1064300 A GB 1064300A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coumermycin
- water
- acetone
- aqueous
- methanol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/075—Benzo[b]pyran-2-ones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/605—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin to a 1-benzopyran-2-on (or the chalcones and hydrogenated chalcones thereof, e.g. coumermycin, novobiocin, novenamin)
Abstract
The invention relates to the antibiotic coumermycin (Notomycin, Registered Trade Mark) which is an acidic substance, effective in inhibiting the growth of Gram positive bacteria, which is readily soluble in acetone, <PICT:1064300/C2/1> <PICT:1064300/C2/2> dioxane and alkaline water, moderately soluble in benzene, methanol and chloroform and insoluble in carbon tetrachloride, petroleum ether and acidic water, which gives positive Fehling and Molisch reactions, decolorizes bromine, and gives negative ninhydrin, Tollens and anthrone reactions, and which in a purified form melts at 222-224 DEG C., exhibits <FORM:1064300/C2/1> of - 134 DEG (C = 1.0% acetone), exhibits an ultraviolet absorption spectrum (Fig. 2) in ethanol having maxima at 275 mm <FORM:1064300/C2/2> , 335 mm <FORM:1064300/C2/3> , in N/10 HCl having maxima at 275 mm <FORM:1064300/C2/4> and 345 mm <FORM:1064300/C2/5> , has a neutral equivalent of 548, an elementary analysis C = 59.1%, H = 5.35%, N = 5.90% and O = 29.65%; and exhibits absorption in the infra-red as shown in Fig. 1. Coumermycin forms salts with (a) aqueous solutions of alkali metal and alkaline earth metal hydroxides, e.g. sodium and calcium coumermycin, (b) organic bases, e.g. procaine, N - benzyl - b - phenethylamine, N,N1 - bis(dehydroabiety) ethylene diamine, ephenamine, N,N1 - dibenzylethylene diamine, dehydroabietylamine, dicyclohexylamine, streptomycin and dihydrostreptomycin. Coumermycin may be extracted from the whole or clarified broth at acid pH, e.g. pH 6.0 by means of a waterimmiscible solvent, e.g. methyl isobutyl ketone, the extract treated with water of pH 10.0 and the aqueous extract so-formed treated with a water - immiscible solvent. After concentration, coumermycin is precipitated from the organic concentrate by addition of a nonsolvent such as petroleum ether. Further purification may be by (a) chromatography on acid treated alumina followed by elution with methanol; (b) countercurrent distribution using carbon tetrachloride/chloroform/methanol/water 5 : 1 : 5 : 1 ; and (c) recrystallization from aqueous acetone and methanol. The antibiotic may be obtained from separated mycelium by extraction with acetone, removal of acetone and reextraction of aqueous residue with methyl isobutyl ketone. Coumermycin is produced by cultivating a coumermycin-producing strain of Streptomyces rishiriensis nov. spec., e.g. ATCC 14812 in an aqueous nutrient medium under submerged aerobic conditions. A suitable medium contains cottonseed endosperm flour, soluble starch, yeast extract, dibasic potassium phosphate, sodium chloride, calcium chloride, magnesium sulphate, zinc sulphate and water.ALSO:A pharmaceutical composition comprises an antibiotic coumermycin (Notomycin, registered Trade Mark) and a carrier. Mastitis in cattle and scours in calves may be treated by a vegetable oil suspension of the antibiotic or capsules. Optional ingredients are (a) antihistamines, (b) sulpha drugs e.g. sulphadiazine, (c) lipotropic agents e.g. methionine, choline, inositol and betasitosterol, (d) central nervous system stimulants e.g. caffeine and ampheta -mines, (e) local anaesthetics, (f) analgesics e.g. aspirin, salicylamide, sodium gentisate, codiene, p-acetylaminophenol and phenacetin, (g) sedatives e.g. barbiturates and bromides, (h) antibiotics e.g. penicillin, streptomycin, bactiracin, polymyxin, tyrothricia, erythromycin, tetracyclines, oleandomycin, neomycin, chloramphenicol, novobiocin, cycloserine, kanamycin and carbomycin, (i) vitamins, (j) hormones e.g. cortisone, 9-a -fluorocortisone, prednisone and prednisolone, (k) anabolic agents e.g. 11,17-dihydroxy-9-a -fluoro-17-a mehyl-4-androsten-3-one, and antifungal agents e.g. mycostatin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24743562A | 1962-12-17 | 1962-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1064300A true GB1064300A (en) | 1967-04-05 |
Family
ID=22934929
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4962263A Expired GB1064300A (en) | 1962-12-17 | 1962-12-17 | A new antibiotic coumermycin |
Country Status (5)
Country | Link |
---|---|
BR (1) | BR6355476D0 (en) |
CH (1) | CH467858A (en) |
DK (1) | DK107542C (en) |
FI (1) | FI40452B (en) |
GB (1) | GB1064300A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004108933A1 (en) * | 2003-06-10 | 2004-12-16 | National Research Council Of Canada | A coumermycin/novobiocin-regulated gene expression system |
US7951913B2 (en) | 2006-06-02 | 2011-05-31 | Biotika A.S. | Method of polymyxin B recovery from fermentation broth |
US8119371B2 (en) | 2006-06-15 | 2012-02-21 | Biotika A.S. | Process for the preparation of polymyxin B employing (PAENI) Bacillus polymyxa |
-
1962
- 1962-12-17 GB GB4962263A patent/GB1064300A/en not_active Expired
-
1963
- 1963-12-13 CH CH1527663A patent/CH467858A/en unknown
- 1963-12-17 FI FI250263A patent/FI40452B/fi active
- 1963-12-17 BR BR15547663A patent/BR6355476D0/en unknown
- 1963-12-17 DK DK586263A patent/DK107542C/en active
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004108933A1 (en) * | 2003-06-10 | 2004-12-16 | National Research Council Of Canada | A coumermycin/novobiocin-regulated gene expression system |
US8377900B2 (en) | 2003-06-10 | 2013-02-19 | National Research Council Of Canada | Coumermycin/novobicin-regulated gene expression system |
US7951913B2 (en) | 2006-06-02 | 2011-05-31 | Biotika A.S. | Method of polymyxin B recovery from fermentation broth |
US8119371B2 (en) | 2006-06-15 | 2012-02-21 | Biotika A.S. | Process for the preparation of polymyxin B employing (PAENI) Bacillus polymyxa |
Also Published As
Publication number | Publication date |
---|---|
FI40452B (en) | 1968-10-31 |
CH467858A (en) | 1969-01-31 |
BR6355476D0 (en) | 1973-07-17 |
DK107542C (en) | 1967-06-12 |
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