JP5779787B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP5779787B2 JP5779787B2 JP2012542507A JP2012542507A JP5779787B2 JP 5779787 B2 JP5779787 B2 JP 5779787B2 JP 2012542507 A JP2012542507 A JP 2012542507A JP 2012542507 A JP2012542507 A JP 2012542507A JP 5779787 B2 JP5779787 B2 JP 5779787B2
- Authority
- JP
- Japan
- Prior art keywords
- xrb
- fraction
- esi
- novel
- fungal strains
- 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.)
- Expired - Fee Related
Links
- 230000002538 fungal effect Effects 0.000 title description 28
- 244000079386 endoparasite Species 0.000 title description 5
- 230000000507 anthelmentic effect Effects 0.000 title description 3
- 108010002156 Depsipeptides Proteins 0.000 claims description 10
- 239000004377 Alitame Substances 0.000 claims description 7
- 239000004159 Potassium persulphate Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims description 6
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 230000000590 parasiticidal effect Effects 0.000 claims 1
- 239000002297 parasiticide Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 23
- 238000004364 calculation method Methods 0.000 description 17
- 238000005259 measurement Methods 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 229920001817 Agar Polymers 0.000 description 13
- 239000008272 agar Substances 0.000 description 13
- 239000003480 eluent Substances 0.000 description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- 230000012010 growth Effects 0.000 description 11
- 241001523964 Xylariaceae Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241001299709 Rosellinia Species 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 6
- 241000223679 Beauveria Species 0.000 description 6
- 241001183555 Coniolariella Species 0.000 description 6
- 241000223218 Fusarium Species 0.000 description 6
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 0 CC(C)CC(C(OC(*)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC1C=CC=CC1)C(OC1C(C)C)=O)=O)=O)=O)=O)=O)=O)N(C)C1=O Chemical compound CC(C)CC(C(OC(*)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC1C=CC=CC1)C(OC1C(C)C)=O)=O)=O)=O)=O)=O)=O)N(C)C1=O 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000011121 hardwood Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 241000221775 Hypocreales Species 0.000 description 3
- 241001214596 Rosellinia abscondita Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006783 corn meal agar Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- WICJNWLMJRLFKQ-NHODMIADSA-N (3s,6r,9s,12r,15s,18r)-4,10,16-trimethyl-3,9,15-tris(2-methylpropyl)-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone Chemical compound CC(C)C[C@@H]1N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC1=O WICJNWLMJRLFKQ-NHODMIADSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- WICJNWLMJRLFKQ-UHFFFAOYSA-N Enniatin-C Natural products CC(C)CC1N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC1=O WICJNWLMJRLFKQ-UHFFFAOYSA-N 0.000 description 2
- 241000221919 Phyllachorales Species 0.000 description 2
- 241001214595 Rosellinia britannica Species 0.000 description 2
- 241001214593 Rosellinia nectrioides Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 108010081513 enniatins Proteins 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-PFUFQJKNSA-N formic acid-d2 Chemical compound [2H]OC([2H])=O BDAGIHXWWSANSR-PFUFQJKNSA-N 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- NGEWQZIDQIYUNV-SCSAIBSYSA-N (R)-2-hydroxy-3-methylbutyric acid Chemical compound CC(C)[C@@H](O)C(O)=O NGEWQZIDQIYUNV-SCSAIBSYSA-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
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- QVZZPLDJERFENQ-UHFFFAOYSA-N Bassianolide Natural products CC(C)CC1N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC1=O QVZZPLDJERFENQ-UHFFFAOYSA-N 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- XCHWVJIIOCMESS-UHFFFAOYSA-N CC(C)CC(C(O)OC(C)C(N(C)C(Cc1ccccc1)C(O)OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC1C=CC=CC1)C(OC1C(C)C)=O)=O)=O)=O)=O)N(C)C1O Chemical compound CC(C)CC(C(O)OC(C)C(N(C)C(Cc1ccccc1)C(O)OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(CC1C=CC=CC1)C(OC1C(C)C)=O)=O)=O)=O)=O)N(C)C1O XCHWVJIIOCMESS-UHFFFAOYSA-N 0.000 description 1
- YENHINQGQJFJRP-UHFFFAOYSA-N CC(C)CC(C(OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(Cc1ccccc1)C(OC(C)C(N(C)C(CC1C=CC=CC1)C(O)OC1C(C)C)O)=O)=O)=O)=O)=O)N(C)C1=O Chemical compound CC(C)CC(C(OC(C(C)C)C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(Cc1ccccc1)C(OC(C)C(N(C)C(CC1C=CC=CC1)C(O)OC1C(C)C)O)=O)=O)=O)=O)=O)N(C)C1=O YENHINQGQJFJRP-UHFFFAOYSA-N 0.000 description 1
- PDWITFQQVAVTGR-LZESCLSUSA-N CC(C)CC(C(OC(C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(Cc1ccccc1)C(O)OC(C(C)C)C(C(C)C1C(OC2C(C)C)=[O]C3=CC=CC[C@]3(C)C1)=O)=O)=O)=O)C#C)=O)N(C)C2O Chemical compound CC(C)CC(C(OC(C(N(C)C(CC(C)C)C(OC(C(C)C)C(N(C)C(Cc1ccccc1)C(O)OC(C(C)C)C(C(C)C1C(OC2C(C)C)=[O]C3=CC=CC[C@]3(C)C1)=O)=O)=O)=O)C#C)=O)N(C)C2O PDWITFQQVAVTGR-LZESCLSUSA-N 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 241001266001 Cordyceps confragosa Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 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 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 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
- 241001465754 Metazoa Species 0.000 description 1
- 241001126260 Nippostrongylus Species 0.000 description 1
- 108010004210 PF 1022A Proteins 0.000 description 1
- 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 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241001299714 Rosellinia necatrix Species 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 241001523963 Xylaria hypoxylon Species 0.000 description 1
- 241001523973 Xylariales Species 0.000 description 1
- 241001340108 Zopfiella ebriosa Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVZZPLDJERFENQ-NKTUOASPSA-N bassianolide Chemical compound CC(C)C[C@@H]1N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC1=O QVZZPLDJERFENQ-NKTUOASPSA-N 0.000 description 1
- 108010076663 bassianolide Proteins 0.000 description 1
- 108010034937 benzyloxycarbonyl-isoleucyl-glutamyl(O-tert-butyl)-alanyl-leucinal Proteins 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001781 electrospray-ionisation quadrupole time-of-flight tandem mass spectrometry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09178799 | 2009-12-11 | ||
| EP09178799.4 | 2009-12-11 | ||
| PCT/EP2010/069040 WO2011069995A1 (en) | 2009-12-11 | 2010-12-07 | Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013513567A JP2013513567A (ja) | 2013-04-22 |
| JP2013513567A5 JP2013513567A5 (enExample) | 2014-02-27 |
| JP5779787B2 true JP5779787B2 (ja) | 2015-09-16 |
Family
ID=43480707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012542507A Expired - Fee Related JP5779787B2 (ja) | 2009-12-11 | 2010-12-07 | 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 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120302496A1 (enExample) |
| EP (1) | EP2509967B1 (enExample) |
| JP (1) | JP5779787B2 (enExample) |
| AR (1) | AR079341A1 (enExample) |
| AU (1) | AU2010329998B2 (enExample) |
| TW (1) | TW201138799A (enExample) |
| UY (1) | UY33095A (enExample) |
| WO (1) | WO2011069995A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104540845B (zh) * | 2012-06-13 | 2018-01-26 | 明治制果药业株式会社 | 新的环缩酚酸肽衍生物以及含有它的有害生物防除剂 |
| WO2015093558A1 (ja) * | 2013-12-18 | 2015-06-25 | Meiji Seikaファルマ株式会社 | 環状デプシペプチド誘導体およびそれを含んでなる有害生物防除剤 |
| CN107835818B (zh) | 2015-05-20 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| KR20220003663A (ko) | 2015-12-28 | 2022-01-10 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 뎁시펩티드 화합물 |
| EP3541789A1 (en) | 2016-11-16 | 2019-09-25 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| CN106749569B (zh) * | 2017-03-03 | 2021-10-15 | 重庆乾泰生物医药有限公司 | 一种pf1022a的分离纯化方法 |
| 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 |
| CN106978353B (zh) * | 2017-03-10 | 2019-10-18 | 广东省微生物研究所 | 特氏炭角菌及其栽培方法 |
| CN113943350B (zh) * | 2021-11-02 | 2023-08-15 | 海南大学三亚南繁研究院 | 一种环肽化合物或其药学上可接受的盐及其制备方法和应用、药物及其应用 |
| 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 |
| WO2025149943A1 (en) * | 2024-01-09 | 2025-07-17 | Animol Discovery, Inc. | Antiparasitic cyclic depsipeptides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO176766C (no) | 1989-02-07 | 1995-05-24 | Meiji Seika Kaisha | Fremgangsmåte for fremstilling av en forbindelse med anthelmintaktivitet |
| JP3207870B2 (ja) * | 1991-04-15 | 2001-09-10 | 明治製菓株式会社 | 環状デプシペプチドおよびその製造法 |
| JP2873894B2 (ja) * | 1992-10-19 | 1999-03-24 | 明治製菓株式会社 | 環状デプシペプチドおよびその製造法 |
| DE4317432A1 (de) * | 1993-05-26 | 1994-12-01 | Bayer Ag | Octacyclodepsipeptide mit endoparasitizider Wirkung |
| DE4341992A1 (de) | 1993-12-09 | 1995-06-14 | Bayer Ag | Endoparasitizide Mittel auf Basis von offenkettigen Tetradepsipeptiden |
| WO1998005655A1 (en) | 1996-08-07 | 1998-02-12 | Meiji Seika Kaisha, Ltd. | Process for producing cyclodepsipeptide compounds and novel cyclodepsipeptide |
| AU2009331930A1 (en) * | 2008-12-16 | 2011-06-30 | Bayer Animal Health Gmbh | Method for producing optically active, cyclic depsipeptides comprising lactic acid and phenyl lactic acid and having 24 ring atoms, using fungus strains of Rosellinia type, and further species of Xylariaceae |
| US9209940B2 (en) | 2009-03-16 | 2015-12-08 | Lg Electronics Inc. | Method of retransmission for supporting MIMO in synchronous HARQ |
-
2010
- 2010-12-07 EP EP10790400.5A patent/EP2509967B1/en not_active Not-in-force
- 2010-12-07 US US13/514,538 patent/US20120302496A1/en not_active Abandoned
- 2010-12-07 WO PCT/EP2010/069040 patent/WO2011069995A1/en not_active Ceased
- 2010-12-07 JP JP2012542507A patent/JP5779787B2/ja not_active Expired - Fee Related
- 2010-12-07 AU AU2010329998A patent/AU2010329998B2/en not_active Ceased
- 2010-12-08 UY UY33095A patent/UY33095A/es not_active Application Discontinuation
- 2010-12-09 AR ARP100104550A patent/AR079341A1/es unknown
- 2010-12-10 TW TW099143150A patent/TW201138799A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2010329998A1 (en) | 2012-07-05 |
| JP2013513567A (ja) | 2013-04-22 |
| AR079341A1 (es) | 2012-01-18 |
| EP2509967B1 (en) | 2016-02-17 |
| US20120302496A1 (en) | 2012-11-29 |
| EP2509967A1 (en) | 2012-10-17 |
| TW201138799A (en) | 2011-11-16 |
| AU2010329998B2 (en) | 2015-05-21 |
| WO2011069995A1 (en) | 2011-06-16 |
| UY33095A (es) | 2011-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013513567A (ja) | 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 | |
| Shimizu et al. | Studies on endophytic actinomycetes (I) Streptomyces sp. isolated from rhododendron and its antifungal activity | |
| García-Pajón et al. | Secondary metabolites isolated from Colletotrichum species | |
| Sumarah et al. | Characterization of polyketide metabolites from foliar endophytes of Picea glauca | |
| Nicoletti et al. | Production and fungitoxic activity of Sch 642305, a secondary metabolite of Penicillium canescens | |
| RU2112807C1 (ru) | Способ получения иммунодепрессанта циклоспорина а и штамм tolypocladium species свs630.92, продуцирующий циклоспорин а | |
| Lumsden et al. | Characterization of major secondary metabolites produced in soilless mix by a formulated strain of the biocontrol fungus Gliocladium virens | |
| Wang et al. | Aflavinines and other antiinsectan metabolites from the ascostromata of Eupenicillium crustaceum and related species | |
| US20110262969A1 (en) | Method for producing optically active, cyclic depsipeptides comprising lactic acid and phenyl lactic and having 24 ring atoms, using fungus strains of rosellinia type, and further species of xylariaceae | |
| JPH02231071A (ja) | 新種トリポクラディウム・バリウム、及びそれを利用するサイクロスポリン系抗生物質の生産方法 | |
| Stadler et al. | Changes in secondary metabolism during stromatal ontogeny of Hypoxylon fragiforme | |
| Gaspari et al. | Myxobacteria isolated in Israel as potential source of new anti‐infectives | |
| Vallet et al. | An integrative approach to decipher the chemical antagonism between the competing endophytes Paraconiothyrium variabile and Bacillus subtilis | |
| Mongkolsamrit et al. | Ophiocordyceps flavida sp. nov.(Ophiocordycipitaceae), a new species from Thailand associated with Pseudogibellula formicarum (Cordycipitaceae), and their bioactive secondary metabolites | |
| Yenn et al. | Enhancement of anti-candidal activity of endophytic fungus Phomopsis sp. ED2, isolated from Orthosiphon stamineus Benth, by incorporation of host plant extract in culture medium | |
| Ramírez-Gil et al. | Polyphasic identification of preharvest pathologies and disorders in avocado cv. Hass | |
| Shew et al. | Qualitative and quantitative soil assays for Phytophthora cinnamomi. | |
| Ali et al. | The endophytic fungus Epicoccum nigrum: Isolation, molecular identification and study its antifungal activity against phytopathogenic fungus Fusarium solani | |
| CN116903463B (zh) | 一种倍半萜类化合物及其制备方法和在抗农业病害中的应用 | |
| Strobel et al. | Phytotoxins from fungi attacking weedy plants | |
| Sun et al. | The efficacy of nematicidal strain Syncephalastrum racemosum | |
| KR100574348B1 (ko) | 그리세오풀빈을 생산하는 자일라리아 속 ah001 균주,이를 포함하는 식물병 방제용 제제 및 이를 이용하여식물병을 방제하는 방법 | |
| Nagia et al. | Secondary metabolites and bioactivity of two fungal strains | |
| ES2920198B2 (es) | Cepa de aspergillus tubingensis y su uso para el aislamiento de compuestos nematicidas | |
| US7335495B2 (en) | Process for the isolation of pharmaceutical compound cyclosporin a from fungus fusarium nivale |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131206 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140110 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20141215 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141216 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150313 |
|
| TRDD | Decision of grant or rejection written | ||
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20150527 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150602 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20150602 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150618 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5779787 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |