PL243850B1 - Method for obtaining 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-on - Google Patents
Method for obtaining 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-on Download PDFInfo
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- -1 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-on Chemical compound 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 12
- 241000235390 Absidia glauca Species 0.000 claims abstract description 8
- 230000009466 transformation Effects 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims 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 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000002906 microbiologic effect Effects 0.000 abstract description 2
- 238000000844 transformation Methods 0.000 abstract description 2
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- GBKJRHFKEPQHMC-UHFFFAOYSA-N ClC(C)C12CCCCC2CC(O1)=O Chemical compound ClC(C)C12CCCCC2CC(O1)=O GBKJRHFKEPQHMC-UHFFFAOYSA-N 0.000 description 3
- 230000001028 anti-proliverative effect Effects 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000004989 O-glycosylation Effects 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000036983 biotransformation Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- YKGCBLWILMDSAV-SFHVURJKSA-N isoxanthohumol Chemical compound C1([C@H]2OC=3C(CC=C(C)C)=C(O)C=C(C=3C(=O)C2)OC)=CC=C(O)C=C1 YKGCBLWILMDSAV-SFHVURJKSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000293029 Absidia caerulea Species 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000009141 biological interaction Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007398 colorimetric assay Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane group Chemical group C1(CCC(CC1)C(C)C)C CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 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
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/65—Absidia
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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Abstract
Przedmiotem zgłoszenia jest sposób otrzymywania optycznie czynnego 1-(1'-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-onu polega na tym, że 1-(1'-chloroetylo)-9-oksabicyklo[4.3.0]nonan-8-on o wzorze 1 poddaje się mikrobiologicznym przekształceniom w kulturze szczepu Absidia glauca AM177 otrzymując 1-(1'-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-on o wzorze 2, który następnie oczyszcza się metodą chromatografii kolumnowej. 1-(1'-Hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-on o wzorze 2 może znaleźć zastosowanie w farmacji jako związek o działaniu antynowotworowym.The subject of the application is a method for obtaining optically active 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one. ]nonan-8-one of formula 1 is subjected to microbiological transformations in the culture of the Absidia glauca AM177 strain to obtain 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 2, which is then purified by column chromatography. 1-(1'-Hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 2 may be used in pharmacy as a compound with anticancer activity.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób otrzymywania 1-(1’-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-onu o wzorze 2 na drodze biotransformacji.The subject of the invention is a method for obtaining 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 2 by biotransformation.
1-(1’-Hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-on wykazuje aktywność antyproliferacyjną in vitro wobec linii nowotworowej (CL-1) oraz nie jest cytotoksyczny względem linii komórek prawidłowych RAW 264.7 i 3T3. Wynalazek może znaleźć zastosowanie w farmacji jako składniki leków antynowotworowych.1-(1'-Hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one has in vitro antiproliferative activity against the cancer line (CL-1) and is not cytotoxic against the normal cell lines RAW 264.7 and 3T3. The invention may be used in pharmacy as ingredients of anticancer drugs.
1-(1’-Chloroetylo)-9-oksabicyklo[4.3.0]nonan-8-on znany jest w literaturze (M. Mazur, A. Włoch, F. Bahri, H. Pruchnik, A. Pawlak, B. Obmińska-Mrukowicz, G. Maciejewska, W. Gładkowski, Chemoenzymatic Synthesis of Enantiomeric, Bicyclic δ-Halo-y-lactones with a Cyclohexane Ring, Their Biological Activity and Interaction with Biological Membranes, Biomolecules, 2020, 10(1), 95, doi:10.3390/biom10010095.).1-(1'-Chloroethyl)-9-oxabicyclo[4.3.0]nonan-8-one is known in the literature (M. Mazur, A. Włoch, F. Bahri, H. Pruchnik, A. Pawlak, B. Obmińska -Mrukowicz, G. Maciejewska, W. Gładkowski, Chemoenzymatic Synthesis of Enantiomeric, Bicyclic δ-Halo-y-lactones with a Cyclohexane Ring, Their Biological Activity and Interaction with Biological Membranes, Biomolecules, 2020, 10(1), 95, doi :10.3390/biom10010095.).
Znany jest szczep Absidia glauca AM177, zdeponowany w kolekcji Katedry Chemii Uniwersytetu Przyrodniczego we Wrocławiu. Z publikacji Bartmańskiej i innych (Transformation of isoxanthohumol by fungi, Journal of Molecular Catalysis B: Enzymatic 61 (2009) 221-224) znana jest biotransformacja izoksantohumolu do glukozydu, przy udziale systemu enzymatycznego Absidia glauca AM177. Podobnie Sordon i inni (Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca, Bioorganic Chemistry 93 (2019) 1027502) ujawniają właściwości tego szczepu w procesie O-glikozylacji flawonoidów. Także hydroksylacja laktonów przy udziale Absidia glauca AM177 znana jest z publikacji Grudniewskiej i innych (Lactones 41. synthesis and microbial hydroxylation of unsaturated terpenoid lactones with p-menthane ring systems, Molecules 2013, 18, 2778-2787; doi:10.3390/molecules18032778).There is a known strain of Absidia glauca AM177, deposited in the collection of the Department of Chemistry of the University of Environmental and Life Sciences in Wrocław. From the publication by Bartmańska et al. (Transformation of isoxanthohumol by fungi, Journal of Molecular Catalysis B: Enzymatic 61 (2009) 221-224) the biotransformation of isoxanthohumol to a glucoside is known with the participation of the Absidia glauca AM177 enzyme system. Similarly, Sordon et al. (Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca, Bioorganic Chemistry 93 (2019) 1027502) reveal the properties of this strain in the process of O-glycosylation of flavonoids. Hydroxylation of lactones with the participation of Absidia glauca AM177 is also known from the publications of Grudniewska and others (Lactones 41. synthesis and microbial hydroxylation of unsaturated terpenoid lactones with p-menthane ring systems, Molecules 2013, 18, 2778-2787; doi:10.3390/molecules18032778).
Nie jest znany sposób wytwarzania 1-(1’-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-onu o wzorze 2, na drodze mikrobiologicznych przekształceń 1-(1’-chloroetylo)-9-oksabicyklo[4.3.0]nonan-8-onu o wzorze 1.There is no known method of producing 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 2 by microbiological transformations of 1-(1'-chloroethyl)-9-oxabicyclo[4.3. 0]nonan-8-one of formula 1.
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Absidia glauca AM177. Po upływie co najmniej 48 h wprowadza się substrat, którym jest 1-(1’-chloroetylo)-9-oksabicyklo[4.3.0]nonan-8-on, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 37°C, przy ciągłym mieszaniu, przynajmniej przez 48 h. Kolejno produkt ekstrahuje się rozpuszczalnikami organicznymi nie mieszającymi się z wodą i oczyszcza znanymi metodami chromatograficznymi.The essence of the invention is that the Absidia glauca AM177 strain is introduced into a medium suitable for filamentous fungi. After at least 48 hours, the substrate is introduced, which is 1-(1'-chloroethyl)-9-oxabicyclo[4.3.0]nonan-8-one, dissolved in an organic solvent miscible with water. The transformation is carried out at temperatures from 20 to 37°C, with constant stirring, for at least 48 h. The product is then extracted with organic solvents immiscible with water and purified using known chromatographic methods.
Korzystne jest, gdy reakcję prowadzi się w podłożu w skład którego wchodzi 1% aminobaku i 3% glukozy.It is preferable when the reaction is carried out in a medium containing 1% aminobac and 3% glucose.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferable when the process is carried out at a temperature of 25 degrees Celsius.
Korzystne jest również, gdy reakcję prowadzi się przez 9 dni.It is also preferred that the reaction is carried out for 9 days.
Zasadniczą zaletą wynalazku jest otrzymanie 1-(1’-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-on, z wydajnością izolowaną 12% wykazującego aktywność antyproliferacyjną in vitro.The main advantage of the invention is the preparation of 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one, with an isolated yield of 12%, showing antiproliferative activity in vitro.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an embodiment.
Do kolb Erlenmayer’a o pojemności 300 ml, zawierającej 50 ml płynnego podłoża w skład którego wchodzi aminobak 1% i glukoza 3% wprowadza się szczep Absidia glauca AM177. Po 72 h jego wzrostu dodaje się 10 mg 1-(1’-chloroetylo)-9-oksabicyklo[4.3.0]nonan-8-onu o wzorze 1 rozpuszczonego w 1 ml acetonu. Transformację prowadzi się przez okres 9 dni. Następnie mieszaninę reakcyjną ekstrahuje się trzykrotnie chloroformem, osusza bezwodnym siarczanem magnezu oraz odparowuje rozpuszczalnik. Otrzymane ekstrakty oczyszcza się chromatograficznie stosując jako eluentu mieszaniny heksan i aceton 20:1.The Absidia glauca AM177 strain is introduced into 300 ml Erlenmayer flasks containing 50 ml of liquid medium consisting of aminobac 1% and glucose 3%. After 72 h of growth, 10 mg of 1-(1'-chloroethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 1 dissolved in 1 ml of acetone are added. The transformation is carried out for a period of 9 days. The reaction mixture is then extracted three times with chloroform, dried over anhydrous magnesium sulfate and the solvent is evaporated. The obtained extracts are purified chromatographically using hexane and acetone 20:1 mixtures as the eluent.
Dane fizyczne i spektroskopowe otrzymanego 1-(1’-hydroksyetylo)-9-oksabicyklo[4.3.0]nonan-8-onu o wzorze 2 są następujące: tt = 76-77°C; 1H NMR (600MHz, CDCI3) δ: 1.30 (d, 3H, J = 6.5 Hz, CH3-11), 1.31 (m, 1H, jeden z CH2-5), 1.39 (m, 1H, jeden z CH2-4), 1.48 (ddd, 1H, J = 13.6, 4.9, 1.2 Hz, jeden z CH2-2), 1,52-1,69 (m, 4H, jeden z CH2-4, jeden z CH2-2, CH2-3), 1.8 (s, 1H, OH), 1,93 (tt, 1H, J = 13.8, 4.4 Hz, jeden z CH2-5), 2.08 (m, 1H, H-6), 2.63 (dd, 1H, J = 19.7, 10.5 Hz, jeden z CH2-7), 2.67 (dd, 1H, J = 19.7, 9.0 Hz, jeden z CH2-7), 4.21 (q, J = 6.6 Hz, 1H, H-10). 13C NMR (600MHz, CDCI3) δ: 13.9 (C-11), 19.1 (C-4), 20.1 (C-3), 24.3 (C-2), 25.1 (C-5), 32.4 (C-7), 37.6 (C-6), 69.2 (C-1), 82.2 (C-10), 171.2 (C-8). IR (KBr, cm-1): 3420 (s), 2936 (m), 1147 (m), 1717 (s), 1246 (m).The physical and spectroscopic data of the obtained 1-(1'-hydroxyethyl)-9-oxabicyclo[4.3.0]nonan-8-one of formula 2 are as follows: mp = 76-77°C; 1H NMR (600MHz, CDCl3) δ: 1.30 (d, 3H, J = 6.5 Hz, CH3-11), 1.31 (m, 1H, one of CH2-5), 1.39 (m, 1H, one of CH2-4 ), 1.48 (ddd, 1H, J = 13.6, 4.9, 1.2 Hz, one of CH2-2), 1.52-1.69 (m, 4H, one of CH2-4, one of CH2-2, CH2- 3), 1.8 (s, 1H, OH), 1.93 (tt, 1H, J = 13.8, 4.4 Hz, one of CH2-5), 2.08 (m, 1H, H-6), 2.63 (dd, 1H , J = 19.7, 10.5 Hz, one of CH2-7), 2.67 (dd, 1H, J = 19.7, 9.0 Hz, one of CH2-7), 4.21 (q, J = 6.6 Hz, 1H, H-10) . 13 C NMR (600MHz, CDCI3) δ: 13.9 (C-11), 19.1 (C-4), 20.1 (C-3), 24.3 (C-2), 25.1 (C-5), 32.4 (C-7) ), 37.6 (C-6), 69.2 (C-1), 82.2 (C-10), 171.2 (C-8). IR (KBr, cm-1): 3420 (s), 2936 (m), 1147 (m), 1717 (s), 1246 (m).
W celu określenia aktywności związku będącego przedmiotem wynalazku, zbadano jego aktywność antyproliferacyjną in vitro wobec linii nowotworowej CL-1 oraz linii komórek prawidłowych RAWIn order to determine the activity of the compound subject to the invention, its in vitro antiproliferative activity was tested against the CL-1 cancer line and the RAW normal cell line.
PL 243850 Β1PL 243850 Β1
264.7 i 3T3. Tabela 1 przedstawia wyniki testów biologicznych in vitro dla otrzymanego laktonu w stosunku do wybranych linii komórkowych. Testy przeprowadzono według metody opisanej w literaturze (Ferrari M., Fornasiero M.C., Isetta A.M. MTT colorimetric assay for testing macrophage cytotoxic activity in vitro. Journal of Immunological Methods, 1990, 131, 165-172).264.7 and 3T3. Table 1 shows the results of in vitro biological tests for the obtained lactone in relation to selected cell lines. The tests were performed according to the method described in the literature (Ferrari M., Fornasiero M.C., Isetta A.M. MTT colorimetric assay for testing macrophage cytotoxic activity in vitro. Journal of Immunological Methods, 1990, 131, 165-172).
Tabela 1Table 1
IC50 - stężenie związku, które hamuje aktywność metaboliczną 50% komórekIC50 - concentration of a compound that inhibits the metabolic activity of 50% of cells
SD - odchylenie standardoweSD - standard deviation
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