# US 4,396,603 A · Novel antibiotic SF-2107 series substance and process for preparing the same

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- Number: US 4,396,603 A
- Document ID: US4396603A
- Status: Granted
- Kind: A
- Application number: 06/313,370
- Filed: 1981-10-21
- Granted: 1983-08-02
- Earliest claimed: 1980-04-01
- Assignees: Meiji Seika Kaisha, Ltd.
- Inventors: Norio Ezaki; Takashi Shomura; Shoichi Amano; Tomizo Niwa; Michio Kojima; Tatsuo Ito
- Web page: https://patentgrep.com/patent/US4396603A

## CPC

- C12N 1/205: Bacterial isolates
- C12P 1/06: by using actinomycetales
- C12R 2001/01: Bacteria or Actinomycetales {; using bacteria or Actinomycetales}
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS

## Abstract

Disclosed is a novel antibiotic SF-2107 series substance consisting essentially of Substance SF-2107 A-1, Substance SF-2107 B and/or Substance SF-2107 C, each having the phisico-chemical properties as described in the specification, which substance exhibits an antibacterial activity against both gram-positive and gram-negative bacteria and is useful for pharmaceuticals, bactericides, disinfectants, etc. Also disclosed is a process for preparing the substance.

## Claims

### Claim 1

An antibiotic Substance SF-2107 A-1 having the following physico-chemical properties:
Elementary analysis:
C, 58.39 wt %; H, 7.88 wt %; O, 33.73 wt % (balance) which does not contain any nitrogen, halogen, sulfur, phosphorus
Molecular weight:
900-1100 (gel filtration method)
Melting point:
170 .degree.-184.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.25 +20.degree. (c=0.2, Methanol)
Ultraviolet absorption spectrum:
Absorption maxima at 250 nm (E.sub.1 cm.sup.1% =72), 342 nm (206), (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3460, 2950, 1730, 1630, 1610, 1460, 1380, 1300, 1280, 1130, 1100, 1040, 910, 860, 820, 790, 750, 740, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Pale yellow powder Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography:
Rf=0.67 (chloroform:methanol=5:1)=0.56 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water

### Claim 2

An antibiotic Substance SF-2107 B having the following physico-chemical properties:
Elementary analysis:
C, 53.66 wt %; H, 6.75 wt %; O, 39.59 wt % (balance) which does not contain any nitrogen, sulfur, phosphorus, or halogen
Molecular weight:
900-1100 (gel filtration method)
Melting point:
170.degree.-175.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.23 =-5.degree. (c=1, Methanol)
Ultraviolet absorption spectrum:
Absorption maxima at 242 nm (E.sub.1 cm.sup.1% =52), 343 (206), (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3450, 2970, 2930, 1720, 1600, 1440, 1370, 1270, 1170, 1130, 1040, 980, 790, 750, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Slightly yellowish powder
Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography:
Rf=0.34 (chloroform:methanol=5:1)=0.51 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water

### Claim 3

An antibiotic Substance SF-2107 C having the following physico-chemical properties:
Elementary analysis:
C, 57.50 wt %; H, 7.04 wt %; O, 34.46 wt % (balance) which does not contain any nitrogen, sulfur, phosphorus, or halogen
Molecular weight:
900-1100 (gel filtration method)
Melting point:
155.degree.-168.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.23 =+29.8.degree. (c=1, methanol)
Ultraviolet absorption spectrum:
Absorption maximum at 345 nm (E.sub.1 cm.sup.1% =258) (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3430, 2930, 1720, 1620, 1600, 1440, 1370, 1300, 1270, 1130, 1100, 1050, 900, 790, 750, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Slightly yellowish powder
Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography:
Rf=0.27 (chloroform:methanol=5:1)=0.07 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water

### Claim 4 (depends on 1)

A process for preparing the antibiotic SF-2107 series substances consisting of SF-2107 A-1, SF-2107B and Sf-2107C as defined in claim 1, or 2 or 3 which comprises cultivating antibiotic SF-2107 series substance-producing microorganism Dactylosporangium sp. SF-2107 in a culture broth containing a carbon source and a nitrogen source under aerobic conditions until substantial antibiotic activity is imparted to said broth and at a temperature of between 25.degree. and 37.degree. C. to produce said antibiotic SF-2107 series substance, and isolating from the culture broth said antibiotic SF-2107 series substance.

### Claim 5

An antibacterial composition which comprises as an active ingredient, an antibacterially effective amount of Substance SF-2107 A-1 having the following physico-chemical properties:
Elementary analysis:
C, 58.39 wt %, H, 7.88 wt %; O, 33.73 wt % (balance) which does not contain any nitrogen, sulfur, phosphorus, or halogen
Molecular weight:
900-1100 (gel filtration method)
Melting point:
170.degree.-184.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.25 =+20.degree. (c=0.2, Methanol)
Ultraviolet absorption spectrum:
Absorption maxima at 250 nm (E.sub.1 cm.sup.1% =72), 342 nm (206), (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3460, 2950, 1730, 1630, 1610, 1460, 1380, 1300, 1280, 1130, 1100, 1040, 910, 860, 820, 790, 750, 740, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Pale yellow powder
Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography: Rf=0.67 (chloroform:methanol=5:1)=0.56 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water, and a pharmaceutically acceptable carrier.

### Claim 6

An antibacterial composition which comprises as an active ingredient, an antibacterially effective amount of Substance SF-2107 B having the following physico-chemical properties:
Elementary analysis:
C, 53.66 wt %; H, 6.75 wt %; O, 39.59 wt % (balance) which does not contain any nitrogen, sulfur, phosphorus, or halogen
Molecular weight:
900-1100 (gel filtration method) PG,29
Melting point:
170.degree.-175.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.23 =-5.degree. (c=1, Methanol)
Ultraviolet absorption spectrum:
Absorption maxima at 242 nm (E.sub.1 cm.sup.1% =52), 343 (206), (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3450, 2970, 2930, 1720, 1600, 1440, 1370, 1270, 1170, 1130, 1040, 980, 790, 750, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Slightly yellowish powder
Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography:
Rf=0.34 (chloroform:methanol=5:1)=0.51 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water, and a pharmaceutically acceptable carrier.

### Claim 7

An antibacterial composition which comprises as an active ingredient, an antibacterially effective amount of Substance SF-2107 C having the following physico-chemical properties:
Elementary analysis:
C, 57.50 wt %; H, 7.04 wt %; O, 35.46 wt % (ballance) which does not contain any nitrogen, sulfur, phosphorus, or halogen
Molecular weight:
900-1100 (gel filtration method)
Melting point:
155.degree.-168.degree. C. (slowly molten)
Specific rotation:
[.alpha]sub.D.sup.23 =+29.8.degree. (c=1, methanol)
Ultraviolet absorption spectrum:
Absorption maximum at 345 nm (E.sub.1 cm.sup.1% =258) (in methanol)
Infrared absorption spectrum:
Characteristic absorption bands at 3430, 2930, 1720, 1620, 1600, 1440, 1370, 1300, 1270, 1130, 1100, 1050, 900, 790, 750, 690 cm.sup.-1 (KBr tablet method)
Color reaction:
Iodine reaction, Lemieux reaction, positive Ninhydrin reaction, ferric chloride reaction, negative
State:
Slightly yellowish powder
Neutrality, acidity or basicity:
Acting as a neutral or weakly acidic substance (electrophoresis)
Silica gel thin-layer chromatography:
Rf=0.27 (chloroform:methanol=5:1)=0.07 (acetone:benzene=5:1)
Solubility:
Soluble in methanol, acetone. Sparingly soluble in benzene, chloroform, n-hexane, water, and a pharmaceutically acceptable carrier.