# US 5,346,919 A · Anti-bacterial substances and microorganisms which produce them

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- Number: US 5,346,919 A
- Document ID: US5346919A
- Status: Granted
- Kind: A
- Application number: 08/100,171
- Filed: 1993-08-02
- Granted: 1994-09-13
- Earliest claimed: 1992-08-03
- Assignees: Nissan Chemical Industries, Ltd.
- Inventors: Tsuneo Watanabe; Takeshi Yasumoto; Michio Murata; Michito Tagawa; Hiroyuki Narushima; Takashi Furusato; Masao Kuwahara; Masami Hanaue; Tatsuya Seki
- Web page: https://patentgrep.com/patent/US5346919A

## CPC

- C07D 493/04: Ortho-condensed systems
- C12N 1/145: Fungi isolates
- C12P 17/181: {Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin}
- C12R 2001/645: Fungi {; Processes using fungi}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

The present invention relates to the compound A of the formula (A), the related compound B, carboxylic acid derived from acid anhydride group of these compounds and esters and salts thereof, microorganisms for producing the compounds, methods for producing the compounds A and/or B by using the microorganisms, and a treated or untreated fermentation broth obtained by culturing strains belonging to genus Zopfiella or Zopfiella curvata No. 37-3 strain. ##STR1## The present invention provides the compounds A and B, derivatives thereof, and treated or untreated fermentation broth obtained by culturing the strains belonging to genus Zopfiella or Zopfiella curvata No. 37-3 strain, which show an excellent activities as antifungal agent and anti-thrombotic agent.

## Claims

### Claim 1

A compound represented by the structural formula (A): ##STR5## or a free acid formed by hydrolyzing one or two acid anhydride groups of compound A, or an ester, or salt thereof.

### Claim 2

Compound A having the following physicochemical properties:
(1) Molecular weight: 390;
(2) Molecular formula: C.sub.21 H.sub.26 O.sub.7 ;
(3) Specific optical rotation: [.alpha]sub.D.sup.23 =-76.8.degree. (C=0.42, methanol);
(4) Color and form of substance: White powder;
(5) Ultraviolet absorption spectrum: .lambda..sub.max MeOH=250 nm(.epsilon.6300);
(6) Infrared absorption spectrum: .nu..sub.max KBr=3300-3500, 2960, 2935, 1850, 1770, 1260, 915, 750 cm.sup.-1 ;
(7) Solubility in solvents: readily soluble in chloroform, ethyl acetate, methanol; sparingly soluble in water;
(8) .sup.13 C nuclear magnetic resonance spectrum (CDCl.sub.3) .delta.(ppm): 13.8, 13.9, 18.5, 22.4, 22.4, 24.9, 28.1, 28.4, 34.1, 34.8, 36.5, 41.7, 71.6, 141.0, 143.3, 145.0, 147.3, 165.0, 165.1, 165.4, 165.5; and
(9) Rf value: Silica gel thin-layer chromatography (Keisel gel 60F.sub.254, Merck Co.) 0.35 in a solvent system of benzene:ethyl acetate:acetic acid (80:1:2 v/v %).

### Claim 3

Compound B having the following physicochemical properties:
(1) Molecular weight: 404;
(2) Molecular formula: C.sub.22 H.sub.28 O.sub.7 ;
(3) Color and form of substance: White powder;
(4) Ultraviolet absorption spectrum: .lambda..sub.max MeOH=246 nm (.epsilon.6200);
(5) Infrared absorption spectrum: .nu..sub.max KBr=2960, 2930, 2860, 1850, 1830, 1770, 1470, 1255, 930, 750, 735 cm.sup.-1 ;
(6) Solubility in solvents: readily soluble in chloroform, ethyl acetate and methanol; sparingly soluble in water; and
(7) .sup.13 C-Nuclear magnetic resonance spectrum (CDCl.sub.3): .delta.(ppm): 13.9, 14.0, 22.4, 22.5, 22.6, 26.7, 27.4, 29.2, 31.5, 34.7, 35.0, 35.9, 41.9, 66.5, 143.9, 144.0, 144.4, 144.7, 164.1, 164.4, 165.2, 165.8.

### Claim 4 (depends on 1)

An antifungal agent comprising compound A as claimed in claim 1 as an effective ingredient.

### Claim 5 (depends on 1)

An agent for control of plant diseases comprising the compound A as claimed in claim 1 as an effective ingredient.

### Claim 6 (depends on 1)

An anti-thrombotic agent comprising compound A as claimed in claim 1 as an effective ingredient.

### Claim 7 (depends on 3)

A method for the production of compound B according to claim 3, comprising the steps of:
culturing a microorganism belonging to the genus Zopfiella in a culture medium; and
harvesting the microorganism and the compound from the culture.

### Claim 8 (depends on 3)

An antifungal agent comprising compound B as claimed in claim 3 as an effective ingredient.

### Claim 9 (depends on 3)

An agent for control of plant diseases comprising compound B as claimed in claim 3 as an effective ingredient.

### Claim 10 (depends on 3)

An anti-thrombotic agent comprising compound B as claimed in claim 3 as an effective ingredient.

### Claim 11 (depends on 1)

A method for the production of compound A as claimed in claim 1, comprising the steps of:
culturing a microorganism belonging to the genus Zopfiella in a culture medium; and
harvesting the microorganism and the compound from the culture.

### Claim 12 (depends on 2)

A method for the production of compound A as claimed in claim 2, comprising the steps of:
culturing a microorganism belonging to the genus Zopfiella in a culture medium; and
harvesting the microorganism and the compound from the culture.