SK285923B6 - Spôsob prípravy 3-O-glykozylkolchicónových zlúčenín - Google Patents

Spôsob prípravy 3-O-glykozylkolchicónových zlúčenín Download PDF

Info

Publication number: SK285923B6
Authority: SK; Slovakia
Prior art keywords: culture; compounds; biotransformation; range; cultures
Prior art date: 1997-10-03

Application number

SK483-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK4832000A3 (en

Inventor

Ezio Bombardelli

Cesare Ponzone

Original Assignee

Indena S.P.A.

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.)

1997-10-03

Filing date

1998-09-30

Publication date

2007-11-02

1998-09-30 Application filed by Indena S.P.A. filed Critical Indena S.P.A.

2000-09-12 Publication of SK4832000A3 publication Critical patent/SK4832000A3/sk

2007-11-02 Publication of SK285923B6 publication Critical patent/SK285923B6/sk

Links

230000036983 biotransformation Effects 0.000 title claims abstract description 23
150000001875 compounds Chemical class 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims description 31
230000008569 process Effects 0.000 title claims description 9
241000194107 Bacillus megaterium Species 0.000 claims abstract description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
239000000758 substrate Substances 0.000 claims description 22
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 19
239000000284 extract Substances 0.000 claims description 10
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 claims description 9
239000008103 glucose Substances 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000001477 organic nitrogen group Chemical group 0.000 claims description 7
239000001888 Peptone Substances 0.000 claims description 6
108010080698 Peptones Proteins 0.000 claims description 6
238000005273 aeration Methods 0.000 claims description 6
235000019319 peptone Nutrition 0.000 claims description 6
235000013372 meat Nutrition 0.000 claims description 5
229930091371 Fructose Natural products 0.000 claims description 4
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
239000005715 Fructose Substances 0.000 claims description 4
AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical class CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 claims description 4
229940066779 peptones Drugs 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
108010009736 Protein Hydrolysates Proteins 0.000 claims description 3
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235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
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239000005018 casein Substances 0.000 claims description 3
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 3
235000021240 caseins Nutrition 0.000 claims description 3
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239000007788 liquid Substances 0.000 claims description 3
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150000002338 glycosides Chemical group 0.000 claims 1
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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LMBIHYWAZRMYEM-UHFFFAOYSA-N 1,2,3-trimethoxy-10-methylsulfanyl-5,6-dihydrobenzo[a]heptalene-7,9-dione Chemical compound C1CC(=O)C2=CC(=O)C(SC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC LMBIHYWAZRMYEM-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000006142 Luria-Bertani Agar Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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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 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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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 2
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GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
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238000005457 optimization Methods 0.000 description 2
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239000011734 sodium Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
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238000011282 treatment Methods 0.000 description 2
239000012137 tryptone Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VVPWAFWXRZAOAI-UHFFFAOYSA-N 1-chloroprop-1-en-2-ol Chemical compound CC(O)=CCl VVPWAFWXRZAOAI-UHFFFAOYSA-N 0.000 description 1
239000004382 Amylase Substances 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
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239000002028 Biomass Substances 0.000 description 1
238000009631 Broth culture Methods 0.000 description 1
102000016938 Catalase Human genes 0.000 description 1
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241000579120 Coliiformes Species 0.000 description 1
108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
108010055629 Glucosyltransferases Proteins 0.000 description 1
102000000340 Glucosyltransferases Human genes 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QSIDJGUAAUSPMG-CULFPKEHSA-N Steviolmonoside Natural products O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QSIDJGUAAUSPMG-CULFPKEHSA-N 0.000 description 1
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230000002745 absorbent Effects 0.000 description 1
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239000013543 active substance Substances 0.000 description 1
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WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
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238000013459 approach Methods 0.000 description 1
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229960001230 asparagine Drugs 0.000 description 1
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230000015556 catabolic process Effects 0.000 description 1
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238000001311 chemical methods and process Methods 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
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238000006731 degradation reaction Methods 0.000 description 1
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238000011143 downstream manufacturing Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000002031 ethanolic fraction Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229930182478 glucoside Natural products 0.000 description 1
150000008131 glucosides Chemical class 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
230000036512 infertility Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000011206 morphological examination Methods 0.000 description 1
CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
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239000012466 permeate Substances 0.000 description 1
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239000011347 resin Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
YWPVROCHNBYFTP-OSHKXICASA-N rubusoside Chemical compound O([C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YWPVROCHNBYFTP-OSHKXICASA-N 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
WTGQALLALWYDJH-AKTDCHNFSA-N scopolamine hydrobromide Chemical compound Br.C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@@H](C2)[C@H]2[C@@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-AKTDCHNFSA-N 0.000 description 1
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235000000346 sugar Nutrition 0.000 description 1
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MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical group OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 1
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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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Microbiology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Peptides Or Proteins (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

SK483-2000A 1997-10-03 1998-09-30 Spôsob prípravy 3-O-glykozylkolchicónových zlúčenín SK285923B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT97MI002255A IT1295272B1 (it)	1997-10-03	1997-10-03	Biotrasformazione di composti colchiconici nei corrispondenti 3- glicosilderivati
PCT/EP1998/006226 WO1999018229A1 (fr)	1997-10-03	1998-09-30	Procede de bio-transformation de composes de colchicone en derives correspondants 3-glycosyl

Publications (2)

Publication Number	Publication Date
SK4832000A3 SK4832000A3 (en)	2000-09-12
SK285923B6 true SK285923B6 (sk)	2007-11-02

Family

ID=11377985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK483-2000A SK285923B6 (sk)	1997-10-03	1998-09-30	Spôsob prípravy 3-O-glykozylkolchicónových zlúčenín

Country Status (20)

Country	Link
US (1)	US6372458B1 (fr)
EP (1)	EP1019521B1 (fr)
KR (1)	KR100536676B1 (fr)
CN (1)	CN1188527C (fr)
AT (1)	ATE328106T1 (fr)
AU (1)	AU745222B2 (fr)
CA (1)	CA2305046C (fr)
CZ (1)	CZ295749B6 (fr)
DE (1)	DE69834736T2 (fr)
DK (1)	DK1019521T3 (fr)
ES (1)	ES2264214T3 (fr)
HU (1)	HU225686B1 (fr)
IL (1)	IL134566A (fr)
IT (1)	IT1295272B1 (fr)
NO (1)	NO320096B1 (fr)
PL (1)	PL190865B1 (fr)
PT (1)	PT1019521E (fr)
RU (1)	RU2218409C2 (fr)
SK (1)	SK285923B6 (fr)
WO (1)	WO1999018229A1 (fr)

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US20040175782A1 (en) *	2003-03-06	2004-09-09	Tethys Research Llc	Biotransformation of compounds using non-prokaryotic microalgae
PL1745140T3 (pl) *	2004-05-12	2010-01-29	Indena Spa	Biotransformacja związków kolchicynoidowych
EP2619315A2 (fr) *	2010-09-22	2013-07-31	Elysian Life Sciences Private Limited	Procédé microbien de biotransformation des composés colchicinoïdes
WO2015097567A1 (fr)	2013-12-23	2015-07-02	Alkaloids Corporation	Procédé pour la conversion de colchicinoïdes en leurs dérivés 3-glycosylés par leur analogues 3-déméthyl correspondants
CN105861601B (zh) *	2016-04-29	2019-05-24	中国药科大学	一种生物转化制备二氢去氢双松柏醇葡萄糖单糖苷(hmzg)的方法

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FR1344157A (fr) *	1959-05-22	1963-11-29	Roussel Uclaf	Nouvelles colchicines et leur procédé d'obtention
US3442953A (en) *	1963-06-19	1969-05-06	Roussel Uclaf	Novel 7-oxo-7-desacetylaminocolchicine compounds
JPS5233195B2 (fr) *	1971-09-30	1977-08-26
IT1285777B1 (it) *	1996-10-07	1998-06-18	Indena Spa	Processo di biotrasformazione di composti colchicinoidi nei corrispondenti 3-glicosilderivati

1997
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1998
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- 1998-09-30 EP EP98952675A patent/EP1019521B1/fr not_active Expired - Lifetime
- 1998-09-30 DK DK98952675T patent/DK1019521T3/da active
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- 1998-09-30 KR KR10-2000-7003216A patent/KR100536676B1/ko not_active Expired - Fee Related
2000
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Also Published As

Publication number	Publication date
AU1028399A (en)	1999-04-27
US6372458B1 (en)	2002-04-16
IL134566A (en)	2004-06-20
IL134566A0 (en)	2001-04-30
HUP0004840A3 (en)	2002-10-28
RU2218409C2 (ru)	2003-12-10
DE69834736T2 (de)	2007-05-10
PL190865B1 (pl)	2006-02-28
CZ20001196A3 (cs)	2000-10-11
EP1019521B1 (fr)	2006-05-31
KR20010030710A (ko)	2001-04-16
NO20001706L (no)	2000-06-05
ES2264214T3 (es)	2006-12-16
NO320096B1 (no)	2005-10-24
PL339620A1 (en)	2001-01-02
CN1273607A (zh)	2000-11-15
CN1188527C (zh)	2005-02-09
HK1031896A1 (en)	2001-06-29
HU225686B1 (en)	2007-06-28
ITMI972255A1 (it)	1999-04-03
NO20001706D0 (no)	2000-04-03
DE69834736D1 (de)	2006-07-06
PT1019521E (pt)	2006-09-29
HUP0004840A2 (hu)	2001-04-28
CA2305046A1 (fr)	1999-04-15
IT1295272B1 (it)	1999-05-04
WO1999018229A1 (fr)	1999-04-15
AU745222B2 (en)	2002-03-14
CA2305046C (fr)	2008-12-09
EP1019521A1 (fr)	2000-07-19
DK1019521T3 (da)	2006-10-02
ATE328106T1 (de)	2006-06-15
KR100536676B1 (ko)	2005-12-14
CZ295749B6 (cs)	2005-10-12
SK4832000A3 (en)	2000-09-12

Legal Events

Date	Code	Title	Description
2017-06-02	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20160930

Publication	Publication Date	Title
CA2252725C (fr)	2008-03-18	Procede de biotransformation de composes colchicinoides afin d'obtenir des derives 3-glycosyle correspondants
Yoshimoto et al.	1981	New anthracycline metabolites from mutant strains of Streptomyces galilaeus MA144-M1 I. Isolation and characterization of various blocked mutants
RU2218409C2 (ru)	2003-12-10	Способ биотрансформации колхиконового соединения в соответствующее 3-0-гликозильное производное
JP4198883B2 (ja)	2008-12-17	コルヒコン化合物を対応する３−グリコシル誘導体に生物学的に転換する方法
HK1019620B (en)	2003-07-11	A process for the biotransformation of colchicinoid compounds into the corresponding 3-glycosyl derivatives
HK1031896B (en)	2005-09-02	A process for the biotransformation of colchicone compounds into the corresponding 3-glycosyl derivatives