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EP2379731A1 - Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae - Google Patents

Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae

Info

Publication number
EP2379731A1
EP2379731A1 EP09767982A EP09767982A EP2379731A1 EP 2379731 A1 EP2379731 A1 EP 2379731A1 EP 09767982 A EP09767982 A EP 09767982A EP 09767982 A EP09767982 A EP 09767982A EP 2379731 A1 EP2379731 A1 EP 2379731A1
Authority
EP
European Patent Office
Prior art keywords
rosellinia
lactic acid
xylariaceae
pf1022a
ring atoms
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.)
Withdrawn
Application number
EP09767982A
Other languages
German (de)
English (en)
Inventor
Achim Harder
Thi Lam Huong Pham
Rene Jarling
Irmtraut Zaspel
Dietrich Ewald
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.)
Bayer Animal Health GmbH
Original Assignee
Bayer Animal Health GmbH
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 Bayer Animal Health GmbH filed Critical Bayer Animal Health GmbH
Priority to EP09767982A priority Critical patent/EP2379731A1/fr
Publication of EP2379731A1 publication Critical patent/EP2379731A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C12P17/14—Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture

Definitions

  • the present invention relates to a process for producing optically active cyclic depsipeptides containing 24-ring atoms (for example PF1022A) by means of the fungal strains of the genus Rosellinia and other genera of the family Xylariaceae or by means of the enzymatic preparations isolated from these fungal strains.
  • PF1022A of general formula (I) is excellently suited for the control of endoparasites, especially in the field of human and veterinary medicine.
  • the present invention relates to a novel process for the preparation of known lactic acid and phenyl lactic acid-containing cyclodepsipeptides having 24 ring atoms.
  • Such cyclic depsipeptides with 24 ring atoms (Octadepsipeptide) and their use as Endoparasitizide are already the subject of a prior patent application (US005571793A).
  • There are a number of chemical and microbial processes for the preparation of 24-ring atomic ds-2-hydroxyisovaleric acid depsipeptides eg by synthesis, see: Ohyama M. et al., Biosci Biotechnol., Biochem (1994) pp.
  • Strain PF1022A was obtained from plant leaves of Camellia japonica, which are found in the Ibaraki
  • the present invention relates to the discovery of novel fungal strains isolated from fruiting bodies of species of the genera Rosellinia and Coniolariella and other xylariacees growing on deadwood of deciduous and coniferous trees, for the production of PF1022A.
  • the ubiquitous genus Rosellinia is classified in the family Xylariaceae, which belongs to the extensive order Xylariales (Phylum Ascomycota). Representatives of this order have characteristic spherical fruiting bodies (perithecia) with defined ostioles, in which the asci are formed with spores.
  • the genera of the family Xylariaceae have very hard brittle perithecia, in which the asci are each with 8 dark brown to black spores.
  • the genus Rosellinia includes a number of species that live saprophytic or endophytic, but also appear as pathogens. Pathogenic species parasitize living wood and root systems of deciduous and coniferous trees. Saprophytic members of this genus live mainly on dead wood, which is already in the decomposition process.
  • the genus Coniolariella was recently separated from the genus Rosellinia as a distinct genus (Checa, J .; Arenal, F. Blanco, N.
  • the fungal strains of the genus Rosellinia of interest here have all been isolated from deadwood samples (e.g., mountain maple, robinia). However, an exact assignment of the tree species to the respective dead wood sample is not always possible due to the different degree of decomposition.
  • the microscopic control it could be estimated in which density and with which maturity the spores appeared.
  • the spore suspension was decadic further diluted and plated from the respective dilution step 100 .mu.l on malt extract agar (MEA).
  • MEA malt extract agar
  • the plates were kept at 18 to 20 0 C, bonitiert daily under the microscope and transmitted germinating spores on fresh potato dextrose agar (PDA).
  • PDA potato dextrose agar
  • the formed mycelium on this medium grows whitish flat and tender without aerial mycelia.
  • the mycelium was extracted by default with methanol.
  • the identification of the ingredients of the mycelial extracts and the quantification of the PF1022A levels are carried out by LC-PDA-ESI-Q-TOF-MS and - MS / MS.
  • Several lines of Rosellinia and of the new genus Coniolariella were found to be positive for the formation of PF1022A.
  • PF1022A producers are assigned to the following species according to morphological features as well as molecular data after sequencing of the ITS1 / 4 portion of the 5.8S rDNA as well as partial 18S and 28S regions:
  • XR-9 Rosellinia corticum or Rosetlinia sp. (Unspecified Rosellinia species) of hardwood
  • XR-19 Rosellinia sp. or R. corticum, either from robinia or from mountain maple
  • XR-21 Rosellinia sp. or R. corticum of hardwood
  • XR-26 Rosellinia sp. or R. corticum of hardwood
  • XR-55 Rosellinia sp. or R. corticum of hardwood
  • XR-56 Rosellinia sp. or R. corticum of hardwood Cultivation experiments were carried out. Compared to Mycelia sterilia T38-18 "wild-type" and the strains Rosellinia abscondita CBS 448.89 and CBS 450.89, the media MEA, mPDA, CMA and seed agar showed significantly faster growth in the new isolated fungal strains.
  • composition of the media used is composition of the media used:
  • CMA Corn flour 50 g / l, agar-agar 15 g / l
  • M1 malt extract 10 g / l, yeast extract 4 g / l, glucose 4 g / l, agar-agar 15 g / l
  • Seed agar Pharmamedia 20 g / l, soy peptone 2 g / l, maltose 40 g / l, MgSO 4 JH 2 O 2 g / l, NaCl 2 g / l, CaCO 3 3 g / l, agar-agar 15 g / l
  • MEA malt extract 17 g / l, agar-agar 15 g / l
  • mPDA glucose 5 g / l, potato starch 20 g / l, yeast extract 1, 5 g / l, agar-agar 15 g / l
  • the mycelial methanol extracts of Mycelia sterilia T38-18 WT: wild type
  • the new isolates XR-9, XFM 5, XR-16, XR-19, XR-21, XR-26, XR-55 and XR-56 were analyzed by high-performance liquid chromatography (HPLC) using two photodiode array (PDA) and mass spectrometer (MS) detectors.
  • HPLC high-performance liquid chromatography
  • Mycelia sterilia produces a series of PF1022 compounds: PF1022-A (C 52 H 76 N 4 O 12) PF1022 B (C 64 H 84 N 4 O 12), PF1022 C (C 58 H 80 N 4 O 12 ), PF1022-D (C 46 H 72 N 4 O 12 ), PF1022-E (C 52 H 76 N 4 O 13 ) and PF1022-F (C 40 H 68 N 4 O 12 ).
  • PF1022-A retention time R t : 25.1 to 25.6 min in the chromatograms when detected with PDA and MS detectors
  • PF1022-D R, 19.5 to 20 min

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Biophysics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

La présente invention porte sur un procédé de fabrication de depsipeptides cycliques contenant de l'acide lactique et de l'acide phényllactique, optiquement actifs, avec 24 atomes de cycle au moyen non seulement des représentants des espèces Rosellinia et Coniolariella (Xylariaceae) issus de corps de fruits se développant sur du bois mort et du bois vivant d'arbres feuillus et résineux, mais encore des souches de champignon du genre Rosellinia isolées directement à partir de bois et de racines d'arbres feuillus et résineux ainsi que d'autres Xylariaceae ou au moyen de préparations enzymatiques isolées à partir de ces souches de champignon. PF1022A avec la formule générale (I) se prête de manière excellente à la lutte contre les endoparasites, en particulier dans le domaine de la médecine humaine et vétérinaire.
EP09767982A 2008-12-16 2009-12-08 Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae Withdrawn EP2379731A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09767982A EP2379731A1 (fr) 2008-12-16 2009-12-08 Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08021792 2008-12-16
PCT/EP2009/008740 WO2010072323A1 (fr) 2008-12-16 2009-12-08 Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae
EP09767982A EP2379731A1 (fr) 2008-12-16 2009-12-08 Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae

Publications (1)

Publication Number Publication Date
EP2379731A1 true EP2379731A1 (fr) 2011-10-26

Family

ID=41510713

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09767982A Withdrawn EP2379731A1 (fr) 2008-12-16 2009-12-08 Procédé de fabrication de depsipeptides cycliques optiquement actifs contenant de l'acide lactique et de l'acide phényllactique avec 24 atomes de cycle avec l'aide de souches de champignon du type rosellinia ainsi que d'autres espèces de xylariaceae

Country Status (20)

Country Link
US (1) US20110262969A1 (fr)
EP (1) EP2379731A1 (fr)
KR (1) KR20110095350A (fr)
CN (1) CN102257154A (fr)
AR (1) AR074673A1 (fr)
AU (1) AU2009331930A1 (fr)
BR (1) BRPI0922388A2 (fr)
CA (1) CA2746733A1 (fr)
CO (1) CO6362018A2 (fr)
CR (1) CR20110325A (fr)
DO (1) DOP2011000182A (fr)
EC (1) ECSP11011117A (fr)
IL (1) IL213006A0 (fr)
MX (1) MX2011006140A (fr)
RU (1) RU2011129395A (fr)
SV (1) SV2011003943A (fr)
TW (1) TW201034681A (fr)
UY (1) UY32322A (fr)
WO (1) WO2010072323A1 (fr)
ZA (1) ZA201104410B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2010329998B2 (en) * 2009-12-11 2015-05-21 Bayer Intellectual Property Gmbh Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides
KR20220003663A (ko) 2015-12-28 2022-01-10 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 구충성 뎁시펩티드 화합물
CN108570016B (zh) * 2017-03-10 2021-11-26 上海医药工业研究院 一种pf1022a分离纯化的方法
WO2018166899A1 (fr) 2017-03-14 2018-09-20 Acidophil Ltd Procédés de production de dérivés de pf1022a
CN109880746B (zh) * 2017-12-06 2023-10-20 海正药业(杭州)有限公司 一种座坚壳属真菌菌株及其应用
WO2020018888A1 (fr) 2018-07-20 2020-01-23 The Board Of Regents Of The University Of Oklahoma Peptides antimicrobiens et méthodes d'utilisation
CN110964646B (zh) * 2019-11-15 2021-07-27 成都大学 一种座坚壳菌、应用、发酵培养基及pf1022a的制备方法
CN115247132B (zh) * 2021-04-26 2024-04-16 中国科学院微生物研究所 一种组合型人工生物结皮治理荒漠的方法
CN114084497B (zh) * 2021-10-25 2023-05-05 中国热带农业科学院海口实验站 一种果蔬保鲜袋及其制备方法与应用
CN114875093B (zh) * 2022-05-20 2024-07-19 浙江海正药业股份有限公司 一种提高pf1022a发酵产量的方法

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
CN1082052C (zh) * 1996-08-07 2002-04-03 明治制果株式会社 制备环状缩肽化合物的方法和新的环状缩肽

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010072323A1 *

Also Published As

Publication number Publication date
UY32322A (es) 2010-07-30
KR20110095350A (ko) 2011-08-24
ZA201104410B (en) 2012-09-26
SV2011003943A (es) 2011-11-08
AU2009331930A1 (en) 2011-06-30
DOP2011000182A (es) 2011-07-15
WO2010072323A1 (fr) 2010-07-01
IL213006A0 (en) 2011-07-31
TW201034681A (en) 2010-10-01
MX2011006140A (es) 2011-08-03
RU2011129395A (ru) 2013-01-27
BRPI0922388A2 (pt) 2019-09-24
CA2746733A1 (fr) 2010-07-01
AR074673A1 (es) 2011-02-02
CN102257154A (zh) 2011-11-23
CO6362018A2 (es) 2012-01-20
US20110262969A1 (en) 2011-10-27
CR20110325A (es) 2011-09-29
ECSP11011117A (es) 2011-07-29

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