PL234088B1 - 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone - Google Patents
7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone Download PDFInfo
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- PL234088B1 PL234088B1 PL418560A PL41856016A PL234088B1 PL 234088 B1 PL234088 B1 PL 234088B1 PL 418560 A PL418560 A PL 418560A PL 41856016 A PL41856016 A PL 41856016A PL 234088 B1 PL234088 B1 PL 234088B1
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- Prior art keywords
- methylbutyl
- hydroxy
- glucopyranosyl
- methyl
- methoxyflavanone
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- 238000000034 method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 241000751139 Beauveria bassiana Species 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241001302652 Bassiana Species 0.000 description 1
- 241000223679 Beauveria Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 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
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002208 flavanones Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 7-O-3-D-4”'-O-metylo-glukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanon, o wzorze 2 przedstawionym na rysunku oraz sposób otrzymywania 7-O-p-D-4'”-O-metylo-glukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanonu.The subject of the invention is 7-O-3-D-4 "- O-methyl-glucopyranosyl-4'-hydroxy-8- [3" -methylbutyl] -5-methoxyflavanone, as shown in the figure, and the preparation of 7- OpD-4 "- O-methyl-glucopyranosyl-4'-hydroxy-8- [3" -methylbutyl] -5-methoxy flavanone.
Związek ten jest biologicznie czynny i może mieć zastosowanie w przemyśle spożywczym i farmaceutycznym.This compound is biologically active and can be used in the food and pharmaceutical industries.
W dostępnej literaturze nie znaleziono doniesień o przedmiotowym związku ani o sposobach jego otrzymywania.In the available literature, no reports of the compound in question or of the methods of its preparation were found.
Glukozylacja flawonoidów zwiększa ich hydrofilowość, co można wykorzystać podczas produkcji rozpuszczalnych w wodzie nutraceutyków. Związek według wynalazku jest potencjalnym materiałem wyjściowym dla dalszych strukturalnych modyfikacji, które mogą okazać się użyteczne w produkcji aktywniejszych związków.Glucosylation of flavonoids increases their hydrophilicity, which can be used in the production of water-soluble nutraceuticals. The compound of the invention is a potential starting material for further structural modifications that may prove useful in the production of more active compounds.
Istotą wynalazku jest 7-O-3-D-4'”-O-metylo-glukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanon.The essence of the invention is 7-O-3-D-4 "- O-methyl-glucopyranosyl-4'-hydroxy-8- [3" -methylbutyl] -5-methoxy flavanone.
Istotą wynalazku jest także sposób otrzymywania tego związku, polegający na tym, że substrat, którym jest 7,4'-dihydroksy-5-metoksy-8-[3”-metylobutylo]-flawanon, poddaje się transformacji mikrobiologicznej, w wyniku czego otrzymuje się 7-O-3-D-4'”-O-metylo-glukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanon. Grzyby strzępkowe z gatunku Beauveria bassiana namnaża się w płynnym podłożu mikrobiologicznym, przy ciągłym mieszaniu reagentów, w temperaturze 12-40°C. Następnie do narośniętej hodowli dodaje się substrat i dalej prowadzi proces, aż do całkowitego zużycia substratu. Po zakończeniu transformacji roztwór transformacyjny ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą, oddziela frakcję organiczną, osusza bezwodnym siarczanem magnezu, odparowuje rozpuszczalnik - i tak otrzymany surowy produkt oczyszcza się za pomocą technik chromatograficznych.The essence of the invention is also the method of obtaining this compound, which consists in that the substrate, which is 7,4'-dihydroxy-5-methoxy-8- [3 "-methylbutyl] -flavanone, is subjected to microbiological transformation, as a result of which 7-O-3-D-4 "- O-methyl-glucopyranosyl-4'-hydroxy-8- [3" -methylbutyl] -5-methoxy flavanone. Filamentous fungi of the species Beauveria bassiana are multiplied in a liquid microbial medium under constant stirring of the reagents at a temperature of 12-40 ° C. Subsequently, a substrate is added to the grown culture and the process is continued until the substrate is completely consumed. After completion of the transformation, the transformation solution is extracted with a water-immiscible organic solvent, the organic fraction is separated, dried over anhydrous magnesium sulfate, the solvent is evaporated - and the crude product thus obtained is purified by chromatographic techniques.
Korzystnie jest, gdy grzybem jest Beauveria bassiana AM278.Preferably the fungus is Beauveria bassiana AM278.
Korzystnie także jest, gdy reakcję prowadzi się w temperaturze 26°C przy ciągłym wstrząsaniu reagentów.It is also preferred that the reaction is carried out at 26 ° C with continuous agitation of the reactants.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Beauveria bassiana następuje reakcja glikozylacji w substracie.In accordance with the invention, the glycosylation reaction in the substrate takes place as a result of the enzyme system contained in the living cells of the Beauveria bassiana culture.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach 7-O-3-D-4'”-O-metyloglukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanonu, jako głównego produktu reakcji w kulturze Beauveria bassiana. Wydajność reakcji osiąga poziom 12%.The main advantage of the invention is obtaining, under mild conditions, 7-O-3-D-4 "- O-methylglucopyranosyl-4'-hydroxy-8- [3" -methylbutyl] -5-methoxy flavanone as the main reaction product in the Beauveria culture bassiana. The reaction yield is 12%.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an embodiment.
P r z y k ł a d 1. Do kolby o pojemności 300 cm3 w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku na 1 dm3 wody destylowanej, wprowadza się grzyby strzępkowe Beauveria bassiana AM278. Po 6 dniach wzrostu drobnoustrojów w temperaturze 26°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 7,4'-dihydroksy-5-metoksy-8-[3”-metylobutylo]-flawanonu, o wzorze 1, rozpuszczonego w 1,5 cm3 dimetylosulfotlenku. Transformację prowadzi się przy ciągłym wstrząsaniu przez 10 dób. Po tym czasie hodowlę zakwasza się 1-molowym kwasem chlorowodorowym do pH 4,5. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Uzyskuje się 3,84 mg surowego ekstraktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform : metanol w stosunku objętościowym 1:1. Po oczyszczeniu otrzymuje się 2,7 mg 7-O-3-D-4”'-O-metylo-glukopiranozylo-4'-hydroksy-8-[3”-metylobutylo]-5-metoksyflawanonu, o wzorze 2 z wydajnością 12%.EXAMPLE 1 To a flask of 300 cm 3 which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku per 1 dm 3 of distilled water is introduced into filamentous fungi, Beauveria bassiana AM278. After 6 days of microbial growth at 26 ° C and with continuous shaking, 15 mg of 7,4'-dihydroxy-5-methoxy-8- [3 "-methylbutyl] flavanone, formula 1, dissolved in 1.5 cm 3 dimethylsulfoxide. The transformation is carried out under continuous shaking for 10 days. After this time, the culture is acidified with 1 M hydrochloric acid to a pH of 4.5. Then, the resulting transformation solution was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 3.84 mg of crude extract is obtained, which is purified by chromatography using 1: 1 by volume chloroform: methanol as eluent. After purification, 2.7 mg of 7-O-3-D-4 "" - O-methyl-glucopyranosyl-4'-hydroxy-8- [3 "-methylbutyl] -5-methoxy flavanone are obtained with a yield of 12 %.
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (600 MHz, DMSO-d6) δ: 0,84 (6H, m, H-4'', H-5''), 1,24 (1H, m, H-2''a),1,34 (1H, m, H-2''b), 1,47 (1H, m, H-3''), 2,44 (1H, m, H-1 ''a), 2,59 (1H, m, H-1 ”b), 2,65 (1H, m, H-3a, eq), 2,93 (1H, m, H-3b, ax), 2,98 (1H, m, H-4'''), 3,24-3,32 (1H, m, H-2''') 3,38-3,49 (2H, m, H-3''', H-5'''), 3,45 (3H, m, C4'''-OCHs), 3,48 (1H, m, H-6'''a), 3,66 (1H, m, H-6'''b), 3,76 (3H, s,C5-OCH), 4,96 (1H, m, H-1'''), 5,35 (1H, m, H-2), 6,45 (1H, s, H-6), 6,78 (2H, m, J = 8,4 Hz, H-3'', H-5'), 7,29 (2H, m, J = 8,4 Hz, H-2', H-6'). 1 H NMR (600 MHz, DMSO-d6) δ: 0.84 (6H, m, H-4 ", H-5"), 1.24 (1H, m, H-2 "), 1.34 (1H, m, H-2 "b), 1.47 (1H, m, H-3"), 2.44 (1H, m, H-1 "a), 2.59 (1H, m, H-1 "b), 2.65 (1H, m, H-3a, eq), 2.93 (1H, m, H-3b, ax), 2.98 (1H, m, H-4 "), 3.24-3.32 (1H, m, H-2") 3.38-3.49 (2H, m, H-3 ", H-5""), 3.45 (3H, m, C4" - OCHs), 3.48 (1H, m, H-6 "" a), 3.66 (1H, m, H-6 "'b), 3.76 (3H, s, C5-OCH), 4.96 (1H, m, H-1 ""), 5.35 (1H, m, H-2), 6.45 ( 1H, s, H-6), 6.78 (2H, m, J = 8.4 Hz, H-3 ", H-5"), 7.29 (2H, m, J = 8.4 Hz , H-2 ', H-6').
13C NMR (150 MHz, DMSO-d6) δ: 20,13/20,19 (C-1''), 22,41/22,50 (C-4''), 22,53/22,64 (C-5''), 27,47/27,49 (C-3''), 38,12 (C-2”), 44,65/44,86 (C-3), 55,55 (C5-OCH), 59,71 (C4'”-OCH), 60,45 (C-6'”), 73,52/73,53 (C-2'''), 76,02 (C-5'”), 76,65 (C-3'''), 77,84 (C-2), 79,45 (C-4'''), 92,54/92,63 (C-6), 100,01 (C-1'''), 106,08/106,20 (C-10), 111,14/111,18 (C-8), 115,08/115,10 (C-3', C-5'), 127,64 (C-2', C-6'), 129,46/129,52 (C-1'), 157,40 (C-4'), 159,44/159,48 (C-5), 160,67/160,75 (C-9), 160,78/160,82 (C-7), 188,82/188,85 (C=0). 13 C NMR (150 MHz, DMSO-d6) δ: 20.13 / 20.19 (C-1 "), 22.41 / 22.50 (C-4"), 22.53 / 22.64 (C-5 "), 27.47 / 27.49 (C-3"), 38.12 (C-2 "), 44.65 / 44.86 (C-3), 55.55 ( C5-OCH), 59.71 (C4 "- OCH), 60.45 (C-6""), 73.52 / 73.53 (C-2""), 76.02 (C-5 '"), 76.65 (C-3""), 77.84 (C-2), 79.45 (C-4""), 92.54 / 92.63 (C-6), 100.01 (C-1 "), 106.08 / 106.20 (C-10), 111.14 / 111.18 (C-8), 115.08 / 115.10 (C-3 ' , C-5 '), 127.64 (C-2', C-6 '), 129.46 / 129.52 (C-1'), 157.40 (C-4 '), 159.44 / 159.48 (C-5), 160.67 / 160.75 (C-9), 160.78 / 160.82 (C-7), 188.82 / 188.85 (C = O).
PL 234 088 B1PL 234 088 B1
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| Application Number | Priority Date | Filing Date | Title |
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| PL418560A PL234088B1 (en) | 2016-09-05 | 2016-09-05 | 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone |
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| PL418560A PL234088B1 (en) | 2016-09-05 | 2016-09-05 | 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone and method for obtaining 7-O-β-D-4'''-O-methyl-glucopyranosyl-4'-hydroxy-8'-[3"-methylbutyl]-5'-methoxyflavanone |
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| Publication Number | Publication Date |
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| PL234088B1 true PL234088B1 (en) | 2020-01-31 |
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