CA1041446A - Antibiotique du groupe de l'aculeacin - Google Patents

Antibiotique du groupe de l'aculeacin

Info

Publication number: CA1041446A
Authority: CA; Canada
Prior art keywords: aculeacin; methanol; powder; aculeacins; antibiotics
Prior art date: 1975-03-21
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

Application number

CA222,766A

Other languages

English (en)

Other versions

CA222766S (en

Inventor

Kimio Mizuno

Katsumi Asano

Akira Yagi

Minoru Toriya

Tetsu Saito

Tetsuo Matsuda

Masaki Takada

Kazuo Matsuura

Shuzo Satoi

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.)

Toyo Jozo KK

Original Assignee

Toyo Jozo KK

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.)

1975-03-21

Filing date

1975-03-21

Publication date

1978-10-31

1975-03-21 Application filed by Toyo Jozo KK filed Critical Toyo Jozo KK

1975-03-21 Priority to CA222,766A priority Critical patent/CA1041446A/fr

1978-10-31 Application granted granted Critical

1978-10-31 Publication of CA1041446A publication Critical patent/CA1041446A/fr

Status Expired legal-status Critical Current

Links

108010049047 Echinocandins Proteins 0.000 title claims abstract description 55
239000003242 anti bacterial agent Substances 0.000 title claims abstract description 15
229940088710 antibiotic agent Drugs 0.000 title abstract description 14
238000000034 method Methods 0.000 claims description 23
108010081349 aculeacin A Proteins 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 6
241000228215 Aspergillus aculeatus Species 0.000 claims description 5
230000003115 biocidal effect Effects 0.000 claims description 5
235000015097 nutrients Nutrition 0.000 claims description 3
YKPHLXGEPNYRPY-ZIUFDZNVSA-N 58814-86-1 Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCCCCCCCCC)[C@@H](C)O)=CC=C(O)C=C1 YKPHLXGEPNYRPY-ZIUFDZNVSA-N 0.000 claims 4
230000000843 anti-fungal effect Effects 0.000 claims 2
229940121375 antifungal agent Drugs 0.000 claims 2
150000001875 compounds Chemical class 0.000 claims 2
241000233866 Fungi Species 0.000 abstract description 7
240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 4
230000001717 pathogenic effect Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 104
FBCLKBXYZRAXNA-PDIPHZEPSA-N aculeacin A Chemical class C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCCCCCCCCC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 FBCLKBXYZRAXNA-PDIPHZEPSA-N 0.000 description 41
239000000843 powder Substances 0.000 description 37
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
238000000862 absorption spectrum Methods 0.000 description 12
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000001228 spectrum Methods 0.000 description 10
239000002609 medium Substances 0.000 description 9
229920001817 Agar Polymers 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
239000008272 agar Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
229960001866 silicon dioxide Drugs 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000007912 intraperitoneal administration Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000004473 Threonine Substances 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
229960002898 threonine Drugs 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000001768 carboxy methyl cellulose Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
239000008112 carboxymethyl-cellulose Substances 0.000 description 4
229940105329 carboxymethylcellulose Drugs 0.000 description 4
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000008103 glucose Substances 0.000 description 4
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 4
241000228212 Aspergillus Species 0.000 description 3
241000222122 Candida albicans Species 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 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
238000005273 aeration Methods 0.000 description 3
238000004166 bioassay Methods 0.000 description 3
229940095731 candida albicans Drugs 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
238000001962 electrophoresis Methods 0.000 description 3
GIGAVEHCPDOYLJ-UHFFFAOYSA-N ethyl acetate;propan-2-ol;hydrate Chemical compound O.CC(C)O.CCOC(C)=O GIGAVEHCPDOYLJ-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000000413 hydrolysate Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
241000223238 Trichophyton Species 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
210000000576 arachnoid Anatomy 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000012911 assay medium Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000012258 culturing Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000401 methanolic extract Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
239000000049 pigment Substances 0.000 description 2
108010018247 saramycetin Proteins 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241001480052 Aspergillus japonicus Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000499489 Castor canadensis Species 0.000 description 1
241000237074 Centris Species 0.000 description 1
241001658057 Cercospora kikuchii Species 0.000 description 1
241001133184 Colletotrichum agaves Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
241000609455 Corynespora cassiicola Species 0.000 description 1
241000501458 Cultus Species 0.000 description 1
241001508801 Diaporthe phaseolorum Species 0.000 description 1
241000223221 Fusarium oxysporum Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
241001495426 Macrophomina phaseolina Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000011779 Menyanthes trifoliata Nutrition 0.000 description 1
241001164593 Merica Species 0.000 description 1
241000191938 Micrococcus luteus Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
241000183024 Populus tremula Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000220317 Rosa Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
VXJPCEOTZNHHOA-UHFFFAOYSA-N [K].OC Chemical compound [K].OC VXJPCEOTZNHHOA-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
229960005261 aspartic acid Drugs 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
YLKUQAFDYMLBCK-UHFFFAOYSA-N butan-1-ol;ethyl acetate Chemical compound CCCCO.CCOC(C)=O YLKUQAFDYMLBCK-UHFFFAOYSA-N 0.000 description 1
DOAOYJIOTYDTNV-UHFFFAOYSA-N butan-1-ol;ethyl acetate;hydrate Chemical compound O.CCCCO.CCOC(C)=O DOAOYJIOTYDTNV-UHFFFAOYSA-N 0.000 description 1
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
-1 chlo~oform Chemical compound 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
229960003964 deoxycholic acid Drugs 0.000 description 1
230000008021 deposition Effects 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
INCWELKXTZCRSA-UHFFFAOYSA-N ethyl acetate;methanol;hydrate Chemical compound O.OC.CCOC(C)=O INCWELKXTZCRSA-UHFFFAOYSA-N 0.000 description 1
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000010200 folin Substances 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
108010005685 myroridin Proteins 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
KSSNXJHPEFVKHY-UHFFFAOYSA-N phenol;hydrate Chemical compound O.OC1=CC=CC=C1 KSSNXJHPEFVKHY-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA222,766A 1975-03-21 1975-03-21 Antibiotique du groupe de l'aculeacin Expired CA1041446A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA222,766A CA1041446A (fr)	1975-03-21	1975-03-21	Antibiotique du groupe de l'aculeacin

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA222,766A CA1041446A (fr)	1975-03-21	1975-03-21	Antibiotique du groupe de l'aculeacin

Publications (1)

Publication Number	Publication Date
CA1041446A true CA1041446A (fr)	1978-10-31

Family

ID=4102609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA222,766A Expired CA1041446A (fr)	1975-03-21	1975-03-21	Antibiotique du groupe de l'aculeacin

Country Status (1)

Country	Link
CA (1)	CA1041446A (fr)

1975
- 1975-03-21 CA CA222,766A patent/CA1041446A/fr not_active Expired

Publication	Publication Date	Title
US3978210A (en)	1976-08-31	Antibiotic aculeacins
CA1072470A (fr)	1980-02-26	Teichomycine, antibiotique produit par l'actinoplanes teichomyceticus
UMEHARA et al.	1983	Studies on WF-3161, a new antitumor antibiotic
CA1129795A (fr)	1982-08-17	Preparation de monacolin k
CA2006144C (fr)	1995-02-21	Procede microbiologique pour la production d'antibiotiques immunosuppresseurs
US4212858A (en)	1980-07-15	Antibiotic aculeacin-Aα, -Aγ, -Dα and -Dγ and methods for their production
EP0274873B1 (fr)	1992-09-23	Antibiotique A10255 complexe et facteurs, procédé, micro-organismes pour sa fabrication
NL8001982A (nl)	1980-10-09	Antibiotisch werkzame stof en werkwijze ter bereiding en toepassing van deze stof en farmaceutisch preparaat, dat deze stof bevat.
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US4902781A (en)	1990-02-20	Novel tripetide derivatives
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US5378611A (en)	1995-01-03	Process for producing 6β,14α-dihydroxy-4-androstene-3, 17-dione amid 14α-hydroxy-4-androstene-3,6,17-trione from 4-androstene-3, 17-dione using myrothecium sp. ferm bp-4432
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KR830000617B1 (ko)	1983-03-10	신 항생물질 sf-2050 물질의 제조법
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US4276382A (en)	1981-06-30	Antibiotic substances