PL220507B1 - 3'-[3"-hydroxy-3"-methylbutyl]-4,4',2'-trihydroxy-6'-methoxy-α,β-dihydrochalcone and a method for its preparation - Google Patents
3'-[3"-hydroxy-3"-methylbutyl]-4,4',2'-trihydroxy-6'-methoxy-α,β-dihydrochalcone and a method for its preparationInfo
- Publication number
- PL220507B1 PL220507B1 PL405454A PL40545413A PL220507B1 PL 220507 B1 PL220507 B1 PL 220507B1 PL 405454 A PL405454 A PL 405454A PL 40545413 A PL40545413 A PL 40545413A PL 220507 B1 PL220507 B1 PL 220507B1
- Authority
- PL
- Poland
- Prior art keywords
- trihydroxy
- methoxy
- methylbutyl
- hydroxy
- substrate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 230000009466 transformation Effects 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 241000228143 Penicillium Species 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000002906 microbiologic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 3'-[3”-hydroksy-3”-metylobutylo]-4,4',2'-trihydroksy-6'-metoksy-a^-dihydrochalkon, o wzorze 2, przedstawionym na rysunku oraz sposób jego wytwarzania.The present invention relates to 3 '- [3 "-hydroxy-3" -methylbutyl] -4,4', 2'-trihydroxy-6'-methoxy-α 1 -dihydro chalcone of the formula 2 shown in the drawing and a method of its preparation.
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.
Dotychczas, w literaturze nie jest znany 3'-[3”-hydroksy-3”-metylobutylo]-4,4',2'-trihydroksy-6'-metoksy-a,3-dihydrochalkon ani sposób jego wytwarzania.Until now, there is no known in the literature 3 '- [3 "-hydroxy-3" -methylbutyl] -4,4', 2'-trihydroxy-6'-methoxy-a, 3-dihydrohalcone or the method of its preparation.
Istotą wynalazku jest 3'-[3”-hydroksy-3”-metylobutylo]-4,4',2'-trihydroksy-6'-metoksy-a,3-dihydrochalkon.The essence of the invention is 3 '- [3 "-hydroxy-3" -methylbutyl] -4,4', 2'-trihydroxy-6'-methoxy-a, 3-dihydroochalcone.
Natomiast istotą sposobu wytwarzania tego związku jest to, że otrzymuje się go na drodze reakcji mikrobiologicznej transformacji substratu, którym jest jakim jest 4,4',2'-trihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkon. Grzyby z gatunku Penicillium albidum, namnaża się w płynnym podłożu mikrobiologicznym, charakterystycznym dla grzybów, przy ciągłym mieszaniu reagentów, w temperaturze 12-40°C. Następnie do narośniętej hodowli dodaje się substrat i dalej prowadzi się proces, aż do całkowitego zużycia substratu. Po zakończeniu transformacji roztwór transformacyjny ekstrahuje się rozpuszczalnikami organicznymi niemieszającymi się z wodą, oddziela frakcję organiczną, osusza bezwodnym siarczanem magnezu, odparowuje rozpuszczalnik i tak otrzymany surowy produkt oczyszcza się pomocą technik chromatograficznych.However, the essence of the method of producing this compound is that it is obtained by microbial transformation of the substrate, which is 4,4 ', 2'-trihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone. Penicillium albidum fungi are multiplied in a liquid microbiological medium, characteristic for fungi, with constant mixing 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 was extracted with water-immiscible organic solvents, the organic fraction was separated, dried over anhydrous magnesium sulfate, the solvent was evaporated, and the crude product thus obtained was purified by chromatographic techniques.
Korzystnie jest, gdy proces namnażania drobnoustroju prowadzi się w temperaturze 30°C.Preferably, the multiplication process of the microorganism is carried out at a temperature of 30 ° C.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Penicillium albidum, następuje reakcja hydratacji w substracie.By following the invention, as a result of the action of the enzyme system contained in the living cells of Penicillium albidum culture, a hydration reaction takes place in the substrate.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach, 3'-[3”-hydroksy-3”-metylobutylo]-4,4',2'-trihydroksy-6'-metoksy-a,3-dihydrochalkon, o wzorze 2, jako głównego produktu reakcji w kulturze Penicillium albidum z wydajnością 30,1%.The main advantage of the invention is to obtain, under mild conditions, 3 '- [3 "-hydroxy-3" -methylbutyl] -4,4', 2'-trihydroxy-6'-methoxy-a, 3-dihydroochalcone of formula 2, as the main reaction product in the Penicillium albidum culture with a yield of 30.1%.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an exemplary embodiment.
P r z y k ł a d 1. Do kolby o pojemności 300 cm3, w której znajduje się 100 cm3 sterylnej pożyw3 ki zawierającej 3 g glukozy i 1 g aminobaku na 1 dm wody destylowanej, wprowadza się grzyby Penicillium albidum. Po 4 dniach wzrostu drobnoustrojów w temperaturze 30°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 4,4',2'-trihydroksy-6'-metoksy-3'-prenylo-a,3-dihydrochalkon, o wzorze 1, rozpuszczonego w 1 cm3 metanolu. Transformację prowadzi się przy ciągłym wstrząsaniu przez 8 dób. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 21,0 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform:metanol w stosunku objętościowym 9:1.EXAMPLE 1 To a flask of 300 cm 3, which is a 100 cm 3 three sterile sued path containing 3 g of glucose and 1 g aminobaku per 1 liter of distilled water is introduced fungus Penicillium albidum. After 4 days of microbial growth at 30 ° C and with continuous shaking, 15 mg of 4,4 ', 2'-trihydroxy-6'-methoxy-3'-prenyl-a, 3-dihydroochalcone, formula 1, dissolved in 1 cm 3 of methanol. The transformation is carried out under continuous shaking for 8 days. Then, the resulting transformation solution was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 21.0 mg of crude product is obtained, which product is purified by chromatography using a 9: 1 by volume mixture of chloroform: methanol as eluent.
Po oczyszczeniu otrzymuje się 4,75 mg 3'-[3”-hydroksy-3”-metylobutylo]-4,4',2'-trihydroksy-6'-metoksy-a,3-dihydrochalkonu, o wzorze 2, z wydajnością 30,1%.After purification, 4.75 mg of 3 '- [3 "-hydroxy-3" -methylbutyl] -4,4', 2'-trihydroxy-6'-methoxy-a, 3-dihydroquinone of formula II are obtained with the yield 30.1%.
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (600 MHz, aceton-d6) δ: 1,23 (6H, s, H-4”, H-5”), 1,65 (2H, m, H-2”), 2,66 (2H, m, H-1”), 2,86 (2H, m, H-β), 3,24 (2H, m, H-a), 3,85 (3H, s, C6'-OCH3), 6,08 (1H, s, H-5'), 6,75 (2H, pd, J= 8,4 Hz, H-3, H-5), 7,09 (2H, pd, J= 8,4 Hz, H-2, H-6), 14,32 (C2'-OH).1H NMR (600 MHz, acetone-d6) δ: 1.23 (6H, s, H-4 ", H-5"), 1.65 (2H, m, H-2 "), 2.66 (2H , m, H-1 "), 2.86 (2H, m, H-β), 3.24 (2H, m, Ha), 3.85 (3H, s, C6'-OCH3), 6.08 (1H, s, H-5 '), 6.75 (2H, pd, J = 8.4 Hz, H-3, H-5), 7.09 (2H, pd, J = 8.4 Hz, H-2, H-6), 14.32 (C2'-OH).
13C NMR (150 MHz, aceton-d6) δ: 17,81 (C-1”), 29,66 (C-4”, C-5”), 30,83 (C-β), 43,21 (C-2”), 46,98 (C-a), 55,94 (C6'-OCH3), 70,79 (C-3”), 91,65 (C-5'), 105,61 (C-1'), 109,92 (C-3'), 116,01 (C-3, C-5), 130,17 (C-2, C-6), 133,38 (C-1), 156,45 (C-4), 162,14 (C-6'), 163,15 (C-4'), 165,69 (C-2'), 205,47 (C=O).13C NMR (150 MHz, acetone-d6) δ: 17.81 (C-1 "), 29.66 (C-4", C-5 "), 30.83 (C-β), 43.21 ( C-2 "), 46.98 (Ca), 55.94 (C6'-OCH3), 70.79 (C-3"), 91.65 (C-5 '), 105.61 (C-1 '), 109.92 (C-3'), 116.01 (C-3, C-5), 130.17 (C-2, C-6), 133.38 (C-1), 156, 45 (C-4), 162.14 (C-6 '), 163.15 (C-4'), 165.69 (C-2 '), 205.47 (C = O).
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL405454A PL220507B1 (en) | 2013-09-27 | 2013-09-27 | 3'-[3"-hydroxy-3"-methylbutyl]-4,4',2'-trihydroxy-6'-methoxy-α,β-dihydrochalcone and a method for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| PL405454A PL220507B1 (en) | 2013-09-27 | 2013-09-27 | 3'-[3"-hydroxy-3"-methylbutyl]-4,4',2'-trihydroxy-6'-methoxy-α,β-dihydrochalcone and a method for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL405454A1 PL405454A1 (en) | 2014-04-14 |
| PL220507B1 true PL220507B1 (en) | 2015-11-30 |
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| PL405454A PL220507B1 (en) | 2013-09-27 | 2013-09-27 | 3'-[3"-hydroxy-3"-methylbutyl]-4,4',2'-trihydroxy-6'-methoxy-α,β-dihydrochalcone and a method for its preparation |
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| PL405454A1 (en) | 2014-04-14 |
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