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WO2003045982A1 - Antibiotiques fki-9739 et leur procede de fabrication - Google Patents

Antibiotiques fki-9739 et leur procede de fabrication Download PDF

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Publication number
WO2003045982A1
WO2003045982A1 PCT/JP2001/010432 JP0110432W WO03045982A1 WO 2003045982 A1 WO2003045982 A1 WO 2003045982A1 JP 0110432 W JP0110432 W JP 0110432W WO 03045982 A1 WO03045982 A1 WO 03045982A1
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WO
WIPO (PCT)
Prior art keywords
antibiotic
fki
antibiotics
formula
compound represented
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.)
Ceased
Application number
PCT/JP2001/010432
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English (en)
Japanese (ja)
Inventor
Satoshi Omura
Kazuro Shiomi
Rokuro Masuma
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kitasato Institute
Original Assignee
Kitasato Institute
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kitasato Institute filed Critical Kitasato Institute
Priority to AU2002222561A priority Critical patent/AU2002222561A1/en
Priority to PCT/JP2001/010432 priority patent/WO2003045982A1/fr
Publication of WO2003045982A1 publication Critical patent/WO2003045982A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Definitions

  • the present invention relates to a substance having the growth inhibitory activity against, for example, microorganisms and arthropods, which is effective as a pharmaceutical, veterinary drug, or agricultural chemical by the following formula [I]
  • the present invention relates to an antibiotic F K 1 -0739 and a process for producing the same.
  • antibiotics produced by microorganisms have been discovered so far, and some of them have been identified, for example, penicillin, streptomycin, amphotericin B, evening irosine, monensin, ivermectin, and blasticidin S. It is well known that polyoxins, etc. have been converted to ffl in the fields of pharmaceuticals, veterinary drugs, and agricultural chemicals (Yoshio Ueno, Satoshi Omura, “Microbial Pharmaceutical Chemistry, 3rd revised edition”, 179-2) 27, Nankodo, 199 5).
  • the present invention solves such problems as toxicity, side effects, and resistance, and has a growth inhibitory activity against microorganisms and arthropods.
  • Another object of the present invention is to provide an antibiotic FK1-0739, which is effective as a pesticide, and a method for producing the same.
  • the antibiotics FK 1-0739 are antibiotics FKI-0739 AK antibiotics FKI-0739A2 and antibiotics FKI-0739B1 and It is a generic term for antibiotics FK 1-0739 ⁇ ⁇ 2, and these antibiotics FK 1-0739 are collected from cultures of microorganisms capable of producing the antibiotics. DISCLOSURE OF THE INVENTION ...
  • the present inventors have continued to search for antibiotics from cultures of microorganisms.
  • the antibiotics FK 1-0739 produced by the filamentous fungi F ⁇ I-0739 The present inventors have found that they have a growth inhibitory activity against arthropods and arthropods, and based on this finding, have completed the present invention, which is a substance that can be effective as a pharmaceutical, animal drug, or agricultural chemical.
  • the antibiotic FKI-0739A1 of the present invention has the following formula [] 1]
  • the compound provides an antibiotic FKI-0739A1 having growth inhibitory activity against microorganisms and arthropods.
  • antibiotic FKI-0739A2 of the present invention has the following formula [ ⁇
  • the compound provides an antibiotic FK1-0739A2 having a growth inhibitory activity against microorganisms and arthropods.
  • antibiotic FKI-0739B1 of the present invention has the following formula [IV]
  • the antibiotic FKI-0. 739 B2 of the present invention has the following formula [V] which provides an antibiotic FKI-0739B2 having growth inhibitory activity against microorganisms and arthropods.
  • the present invention belongs to a filamentous fungus, and has the following formula [I]
  • a microorganism having the ability to produce FK 1 -0739 is represented by the following formula:
  • Another object of the present invention is to provide a method for accumulating 1-0739 and collecting FK1-0739 from the culture. Further, the present invention relates to a method of dissolving the antibiotics FK I-0 739 A1 and FK I-0 739 B1 in methanol and leaving them in a glass container at room temperature under room light to obtain the antibiotics FK 1-079 -It provides a production method for converting to 0 739 A2 and 0 739 B2.
  • the present invention provides a microorganism itself belonging to a filamentous fungus and having the ability to produce antibiotics FKI-07339. Furthermore, the present invention provides a microorganism, Pergilus SP (A spergi 11 uss p.) FKI-07339 (FERM BP-77786).
  • a microorganism capable of producing the antibiotic FK 1-0739 represented by the above formula [I] (hereinafter referred to as “FK 1-0739 substance producing bacterium”) is a filamentous fungus.
  • FK 1-0739 substance producing bacterium is a filamentous fungus.
  • a preferred example of the strain used for producing the antibiotic FK 1-0 739 of the present invention is, for example, a filamentous fungus FK 1-0 newly isolated from the soil of Oki Prefecture by the present inventors. 739 strains.
  • the bacteriological properties of this strain are as follows.
  • This strain is relatively stable on ⁇ apecker's yeast extract agar medium, 20% sucrose buckwheat extract extract agar medium, wort agar medium, potato vinegar agar medium, Miura agar medium, etc. It grew well and the conidium was well established o
  • Conidia (6.0-11.0 X 3.0-5.0 urn) are formed one after another from the tip of the phialide, resulting in a radial conidia head by a nucleophilic chain. Conidia are spherical to subspherical in diameter, 3.5 to 5.5 m in diameter, with irregular irregular projections and rough surfaces.
  • Table 1 below shows the macroscopic observation results when this strain was cultured on various agar media at 25 for 7 days.
  • Table 1 Medium Growth state on medium Colony-front surface ⁇ knee back surface soluble dye
  • Optimal growth conditions for this strain are pH 4-8, temperature 19-32 ° C.
  • the growth range of this strain is pH 3 to 10 and temperature is 12 to 41 ° C.
  • the strain belongs to the genus Aspergillus (A spergi 11 1s). Aspergillus sp. FK I-0
  • This strain is independent as Aspergillus' SP FK I-0739 (As pergilluss p. FK I-0739), located at 1-1, Higashi, 1-chome, Tsukuba, Ibaraki, Japan (Postal code 305-8566). It has been deposited with the National Institute of Advanced Industrial Science and Technology (AIST). The date of deposit was October 29, 2001, and the deposit number is FERM BP-7786.
  • a fungus producing an antibiotic FK 1 -0739 belonging to filamentous fungi may be cultured in a medium, and then separated and purified from the culture.
  • the strains that can be used in the present invention all of the above-mentioned strains, mutant strains thereof, and fungi-producing bacteria belonging to the class of filamentous fungi, FK1-0739, can be used.
  • Any suitable nutrient source for the production of the above antibiotics FK 1 -0739 may be used as long as it can be used as a nutrient source for filamentous fungi.
  • nitrogen sources such as commercially available peptone, meat extract, corn steep liquor, cottonseed flour, peanut flour, soy flour, yeast extract, NZamine, casein hydrate, sodium nitrate, ammonium nitrate, ammonium sulfate, etc.
  • Glycerin starch, glucose, galactose, mannose, etc.
  • Carbon sources such as carbohydrates or fats and inorganic salts such as salt, phosphate, calcium carbonate and magnesium sulfate can be used alone or in combination.
  • trace amounts of metal salts and animal / vegetable / mineral oils can be added as antifoaming agents. Any of these can be used as long as they are useful for the production of the antibiotics FK 1 -0739s using the production bacteria, and any known culture materials of filamentous fungi can be used. Liquid culture is preferred for large-scale cultivation of antibiotics FK1-0739s, and the culture temperature can be applied within a range in which the producing bacteria can grow and produce antibiotics FK1-0739s. The cultivation can be performed by appropriately selecting according to the properties of the bacteria producing the antibiotic FK 1 -0739 using the conditions described above.
  • the antibiotics FK 1 -0739 can be extracted from the culture using a water-immiscible organic solvent such as black-mouthed form and ethyl acetate.
  • a water-immiscible organic solvent such as black-mouthed form and ethyl acetate.
  • known methods used for collecting fat-soluble substances for example, adsorption chromatography, gel filtration orifice chromatography, scraping from thin layer chromatography, centrifugal countercurrent distribution chromatography, and high speed Pure collection can be achieved by appropriately combining or repeating liquid chromatography and the like.
  • the antibiotics FKI-0739A1 and FKI-0739B1 should be dissolved in methanol and left at room temperature, in a glass container, and under room light. Can be converted into the antibiotics FK1-0739A2 and FKI-0739B2, respectively.
  • the physicochemical properties of the antibiotics FK 1 -0739s according to the present invention are as follows.
  • Infrared absorption spectrum measured by bromide lithium tablet method is 330, 2927, 1633, 1538, 1449. 6, having 1 4 5 6 1 2 3 0 1 1 0 3, 74 8, 7 0 0 absorption maximum in cm 1,
  • Solubility in solvents Soluble in chloroform, ethyl acetate, acetone, methanol, and acetonitrile, poorly soluble in water, n-hexane,
  • the antibiotic FKI-0379A1 has a chemical structure represented by the following formula [IT]. It was decided.
  • the infrared absorption spectrum measured by the bromide power pill tablet method is 341 9, 2962, 2926, 2854, 1628, 1549, 1454, 126 1, has a maximum absorption at 1, 097, 1029, 800, 743, 700 cnT 1 ,
  • Solubility in solvents Soluble in chloroform, ethyl acetate, acetone, methanol, and acetonitrile, poorly soluble in water, n-hexane,
  • the antibiotic FK 1-0379 A2 has a chemical structure represented by the following formula [M]. It was decided.
  • Table 4 shows the chemical shift (PP m) and spin coupling constant (Hz) in heavy acetone.
  • the antibiotic FKI-0379B1 has a chemical structure represented by the following formula [W]. It was decided.
  • Table 5 shows the chemical shift (ppm) and spin coupling constant (Hz) in deuterated acetone.
  • Solubility in solvents Soluble in chloroform, ethyl acetate, acetone, methanol, and acetonitrile, poorly soluble in water and n-hexane,
  • the antibiotic FKI-0379B2 has a chemical structure represented by the following formula [V].
  • the antibiotic FKI - 0739 A 1 and antibiotic FK I- 0739 B 1 is the proton nuclear magnetic resonance scan Bae spectrum and 13 C nuclear magnetic resonance scan Bae spectrum, each molecular formula 2
  • the signal was almost doubled, which is considered to be due to the presence of two conformers at a ratio of about 54.
  • the antibiotic FK I -0739 AK antibiotic FK 1 -0739 A2 FK I -0739 B 1 and FK I -0739 B 2 of the present invention (note that in the table below ⁇ , only AIA 2 B 1 and B Table 6 shows the minimum growth inhibitory concentrations (based on the agar plate dilution method) of various microorganisms on a nutrient agar medium (denoted as 2).
  • the antibiotics of the present invention FKI-0739A1, FKI-0739A2, FKI-0 73 9 B 1 and FK I—07 7 9 B 2 are Next, the anti-arthropod activity of the antibiotics FKI-0739 AK FKI-0739 A2, FKI-0739 BK FKI-0739 B2 of the present invention was shown below. It is described in.
  • an assay medium lecithin 0.01%, carbonate (Sodium hydrogen 7.5mM, potassium chloride 7.5mM, calcium chloride dihydrate 7.5mM, magnesium sulfate heptahydrate 7.5mM) 250 were added and shaken for 15 minutes.
  • the antibiotics FKI-0739A1, FKI-0739A2, FKI-0739BK FKI-0739B2 of the present invention are arthropods. It shows growth inhibitory activity against and can be used as a drug such as an insecticide.
  • Aspergillus sp. (A speri 11 1 ss p.) FK I-0739 strain (FERM BP-7786) cultured on an agar slant medium, glucose 2.0%, polypeptone (Nippon Pharmaceutical Co., Japan ) 0.5%, yeast extract (Oriental Yeast Co., Ltd., Japan) 0.2%, agar 0.1%, potassium dihydrogen phosphate 0.1%, magnesium sulfate heptahydrate 0.
  • One platinum loop was inoculated into a large test tube containing 1 Om1 of a liquid medium (pH 5.7) consisting of 05%, and cultured with shaking at 27 ° C for 3 days.
  • the culture solution was separated into a supernatant and cells by centrifugation, and the supernatant was extracted with ethyl acetate.
  • the cells were extracted with methanol, concentrated under reduced pressure to remove the methanol, and further extracted with ethyl acetate.
  • the extract was concentrated under reduced pressure together with the supernatant ethyl acetate extract to obtain 388 mg of crude substance I. I got This was placed on a silica gel column (Merck Art. 7734, Merck, USA) packed with black-mouthed form and washed with black-mouthed form. Chloroform-methanol (100: 1) and (50: 1) ), And the fractions were concentrated under reduced pressure to obtain 258 mg of FKI-0739A and 18.8 m of FKI-0739B.
  • FK I-0739 Class A substance was subjected to high performance liquid chromatography [Pegasi 1 ODS, 020 X 250 mm, Senshu Ichikagaku Co., Ltd., Japan]. By concentrating them under reduced pressure, 22 Omg of the antibiotic FKI-0739A1 and 10.2 mg of the antibiotic FKI-0739A2 could be isolated.
  • For FKI-0739B substances perform high performance liquid chromatography (Pe gasi 1 ⁇ DS, 0200 x 25 Omm), collect peaks using 50% acetonitrile as the mobile phase, and concentrate them under reduced pressure. As a result, 11.01 mg of the antibiotic FKI-0739B1 and 2.1 mg of the antibiotic FKI-0739B2 could be isolated.
  • Example 2 Example 2
  • the antibiotics FKI-0739AK FKI-0739A2, FKI-0739B1 and FKI-0739B2 are useful as antibacterial or insecticides.
  • a microorganism having the ability to produce the antibiotic FK-0739A1, FKI-0739A2, FKI-0739B1 and FKI-0739B2 belonging to the filamentous fungus is cultured in a medium, and cultured.
  • the antibiotic FK 1 -073 9 AK FKI -0739A2, FKI -0739 B1 and FKI -0739 B2 were accumulated in the product, and the present antibiotic was isolated and produced from the culture to obtain Antibiotics ,
  • Quality FKI-0739 is expected to be an effective substance as a pharmaceutical, veterinary drug, and agrochemical because it has growth inhibitory activity against microorganisms and arthropods.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Wood Science & Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention porte sur les antibiotiques FKI-9739 de formule générale (I) obtenus par mise en culture dans un milieu approprié de micro-organismes de la classe des Hyphomycetes capables de produire lesdits antibiotiques et de les accumuler dans le milieu dont on les extrait. Dans ladite formule, R représente H ou hydroxy. En raison de leur capacité d'inhibition de la croissance des micro-organismes et des arthropodes, les antibiotiques FKI-9739 ainsi obtenus sont utiles comme agents antibactériens et insecticides.
PCT/JP2001/010432 2001-11-29 2001-11-29 Antibiotiques fki-9739 et leur procede de fabrication Ceased WO2003045982A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002222561A AU2002222561A1 (en) 2001-11-29 2001-11-29 Antibiotics fki-9739 and process for producing the same
PCT/JP2001/010432 WO2003045982A1 (fr) 2001-11-29 2001-11-29 Antibiotiques fki-9739 et leur procede de fabrication

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2001/010432 WO2003045982A1 (fr) 2001-11-29 2001-11-29 Antibiotiques fki-9739 et leur procede de fabrication

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63307875A (ja) * 1987-01-31 1988-12-15 Takeda Chem Ind Ltd ハロサイアミンおよびその製造法
JPH01149766A (ja) * 1987-12-04 1989-06-12 Otsuka Pharmaceut Co Ltd インドール誘導体
JPH1017593A (ja) * 1996-06-27 1998-01-20 Rikagaku Kenkyusho 新規ペプチド、その製法、それを含有する細胞周期阻害剤
WO2001019791A2 (fr) * 1999-09-10 2001-03-22 Morphochem Ag Derives de 3-vinylpyrrole, leur procede de production et leur utilisation en tant que medicament

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63307875A (ja) * 1987-01-31 1988-12-15 Takeda Chem Ind Ltd ハロサイアミンおよびその製造法
JPH01149766A (ja) * 1987-12-04 1989-06-12 Otsuka Pharmaceut Co Ltd インドール誘導体
JPH1017593A (ja) * 1996-06-27 1998-01-20 Rikagaku Kenkyusho 新規ペプチド、その製法、それを含有する細胞周期阻害剤
WO2001019791A2 (fr) * 1999-09-10 2001-03-22 Morphochem Ag Derives de 3-vinylpyrrole, leur procede de production et leur utilisation en tant que medicament

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BECK B. ET AL.: "One-pot synthesis and biological evaluation of aspergillamides and analogues", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 10, no. 15, 2000, pages 1701 - 1705, XP004213227 *
TOSKE S.G. ET AL.: "Aspergillamides A and B: modified cytotoxic tripeptides produced by a marine fungus of the genus aspergillus", TETRAHEDRON, vol. 54, no. 44, 1998, pages 13459 - 13466, XP004139351 *

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