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 xylariaceaeInfo
- 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- Withdrawn
Links
- 241001299709 Rosellinia Species 0.000 title claims abstract description 22
- 241001523964 Xylariaceae Species 0.000 title claims abstract description 9
- 125000006413 ring segment Chemical group 0.000 title claims abstract description 6
- 108010002156 Depsipeptides Proteins 0.000 title abstract description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 title abstract description 3
- 235000014655 lactic acid Nutrition 0.000 title abstract description 3
- 239000004310 lactic acid Substances 0.000 title abstract description 3
- 241000233866 Fungi Species 0.000 title abstract 3
- 241000894007 species Species 0.000 title description 7
- 108010004210 PF 1022A Proteins 0.000 claims abstract description 22
- YJNUXGPXJFAUQJ-LYWANRAQSA-N PF1022A Chemical compound C([C@@H]1C(=O)N(C)[C@H](C(O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](CC=2C=CC=CC=2)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O1)=O)CC(C)C)C1=CC=CC=C1 YJNUXGPXJFAUQJ-LYWANRAQSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 3
- 230000002538 fungal effect Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- 241001606010 Rosellinia aquila Species 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000002023 wood Substances 0.000 abstract description 7
- 241001183555 Coniolariella Species 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 3
- 244000079386 endoparasite Species 0.000 abstract description 2
- 229920001817 Agar Polymers 0.000 description 10
- 235000010419 agar Nutrition 0.000 description 10
- 241000088443 Rosellinia sp. Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000011121 hardwood Substances 0.000 description 6
- 241000836835 Coniolariella hispanica Species 0.000 description 5
- 241000206672 Gelidium Species 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000001965 potato dextrose agar Substances 0.000 description 5
- -1 PF1022A compound Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 244000033014 Acer spicatum Species 0.000 description 3
- 235000015801 Acer spicatum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 244000100205 Robinia Species 0.000 description 2
- 241001214596 Rosellinia abscondita Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- VOXXWSYKYCBWHO-QMMMGPOBSA-N (S)-3-phenyllactic acid Chemical compound OC(=O)[C@@H](O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-QMMMGPOBSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- XPMDWESLXQSFAQ-UHFFFAOYSA-N 2-hydroxy-2-phenylpropanoic acid;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.OC(=O)C(O)(C)C1=CC=CC=C1 XPMDWESLXQSFAQ-UHFFFAOYSA-N 0.000 description 1
- 241001430339 Abscondita Species 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 240000001548 Camellia japonica Species 0.000 description 1
- 235000006467 Camellia japonica Nutrition 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- 241000143442 Daldinia Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000143682 Hypoxylon Species 0.000 description 1
- 108091023242 Internal transcribed spacer Proteins 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241001459643 Poronia Species 0.000 description 1
- 241001299714 Rosellinia necatrix Species 0.000 description 1
- 241001523965 Xylaria Species 0.000 description 1
- 241000647402 Xylaria obovata Species 0.000 description 1
- 241001523973 Xylariales Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229940022769 d- lactic acid Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical compound CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001781 electrospray-ionisation quadrupole time-of-flight tandem mass spectrometry Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 230000007483 microbial process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (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.
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5779787B2 (ja) * | 2009-12-11 | 2015-09-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 真菌株から由来の新規な２４員のシクロオクタデプシペプチドおよびその駆虫剤または内部寄生虫駆除剤としての使用 |
| KR102427124B1 (ko) | 2015-12-28 | 2022-07-28 | 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 |
| CN114875093A (zh) * | 2022-05-20 | 2022-08-09 | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0930304A4 (fr) * | 1996-08-07 | 2000-03-01 | Meiji Seika Co | Procede de production de composes a base de cyclodepsipeptide et nouveau cyclodepsipeptide |
-
2009
- 2009-12-08 RU RU2011129395/10A patent/RU2011129395A/ru not_active Application Discontinuation
- 2009-12-08 WO PCT/EP2009/008740 patent/WO2010072323A1/fr active Application Filing
- 2009-12-08 KR KR1020117013683A patent/KR20110095350A/ko not_active Application Discontinuation
- 2009-12-08 CA CA2746733A patent/CA2746733A1/fr not_active Abandoned
- 2009-12-08 EP EP09767982A patent/EP2379731A1/fr not_active Withdrawn
- 2009-12-08 BR BRPI0922388A patent/BRPI0922388A2/pt not_active IP Right Cessation
- 2009-12-08 MX MX2011006140A patent/MX2011006140A/es unknown
- 2009-12-08 US US13/133,611 patent/US20110262969A1/en not_active Abandoned
- 2009-12-08 CN CN2009801509552A patent/CN102257154A/zh active Pending
- 2009-12-08 AU AU2009331930A patent/AU2009331930A1/en not_active Abandoned
- 2009-12-14 UY UY0001032322A patent/UY32322A/es not_active Application Discontinuation
- 2009-12-15 AR ARP090104885A patent/AR074673A1/es not_active Application Discontinuation
- 2009-12-16 TW TW098143185A patent/TW201034681A/zh unknown
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2011
- 2011-05-19 IL IL213006A patent/IL213006A0/en unknown
- 2011-06-08 CO CO11071014A patent/CO6362018A2/es not_active Application Discontinuation
- 2011-06-09 EC EC2011011117A patent/ECSP11011117A/es unknown
- 2011-06-10 DO DO2011000182A patent/DOP2011000182A/es unknown
- 2011-06-10 SV SV2011003943A patent/SV2011003943A/es unknown
- 2011-06-13 CR CR20110325A patent/CR20110325A/es unknown
- 2011-06-14 ZA ZA2011/04410A patent/ZA201104410B/en unknown
Non-Patent Citations (1)
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| See references of WO2010072323A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0922388A2 (pt) | 2019-09-24 |
| AU2009331930A1 (en) | 2011-06-30 |
| IL213006A0 (en) | 2011-07-31 |
| CO6362018A2 (es) | 2012-01-20 |
| CA2746733A1 (fr) | 2010-07-01 |
| RU2011129395A (ru) | 2013-01-27 |
| CR20110325A (es) | 2011-09-29 |
| ECSP11011117A (es) | 2011-07-29 |
| MX2011006140A (es) | 2011-08-03 |
| SV2011003943A (es) | 2011-11-08 |
| WO2010072323A1 (fr) | 2010-07-01 |
| CN102257154A (zh) | 2011-11-23 |
| KR20110095350A (ko) | 2011-08-24 |
| AR074673A1 (es) | 2011-02-02 |
| ZA201104410B (en) | 2012-09-26 |
| UY32322A (es) | 2010-07-30 |
| TW201034681A (en) | 2010-10-01 |
| US20110262969A1 (en) | 2011-10-27 |
| DOP2011000182A (es) | 2011-07-15 |
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