PL234085B1 - 4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone and method for obtaining 4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone - Google Patents

4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone and method for obtaining 4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone Download PDF

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PL234085B1
PL234085B1 PL418557A PL41855716A PL234085B1 PL 234085 B1 PL234085 B1 PL 234085B1 PL 418557 A PL418557 A PL 418557A PL 41855716 A PL41855716 A PL 41855716A PL 234085 B1 PL234085 B1 PL 234085B1
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methylbutyl
methoxy
glucopyranosyl
dihydroxy
dihydroochalcone
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PL418557A
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PL418557A1 (en
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Jarosław Popłoński
Sandra Sordon
Tomasz Tronina
Ewa Huszcza
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Wrocław University Of Environmental And Life Sciences
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Description

Opis wynalazkuDescription of the invention

Przedmiotem wynalazku jest 4'-O^-D-glukopiranozylo-4,2’-dihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochaIkon, o wzorze 2 przedstawionym na rysunku oraz sposób otrzymywania 4-O-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6-metoksy-a,3-dihydrochalkonu.The subject of the invention is 4'-O, -D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-a, 3-dihydroochonium, of the formula 2 shown in the figure and the preparation of 4 -O-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6-methoxy-α, 3-dihydroochalcone.

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 4’-O-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6'-metoksy-α,β-dihydrochalkon.The essence of the invention is 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-α, β-dihydroochalcone.

Istotą wynalazku jest także sposób otrzymywania tego związku, polegający na tym, że substrat, którym jest 4,2',4,-trihydroksy-3'-[3-2-metylobutylo]-6'-metoksy-a^-dihydrochalkon, poddaje się transformacji mikrobiologicznej, w wyniku czego otrzymuje się 4'-O-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkon. Grzyby strzępkowe z gatunku Absidia coerulea 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 starting material, which is 4,2 ', 4, -trihydroxy-3' - [3-2-methylbutyl] -6'-methoxy-α1-dihydro chalcone, is subjected to microbial transformation is performed to give 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-α, 3-dihydroochalcone. Filamentous fungi of the species Absidia coerulea 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 was extracted with a water-immiscible organic solvent, 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 grzybem jest Absidia coerulea AM93.Preferably the fungus is Absidia coerulea AM93.

Korzystnie również jest, gdy reakcję prowadzi się w temperaturze 26°C.It is also preferred that the reaction is carried out at a temperature of 26 ° C.

Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Absidia coerulea następuje reakcja glukozylacji w substracie.By following the invention, a glucosylation reaction in the substrate takes place as a result of the enzyme system contained in the living cells of Absidia coerulea.

Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach 4’-O-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6’-metoksy-a,3-dihydrochalkonu, jako głównego produktu reakcji w kulturze Absidia coerulea. Wydajność reakcji osiąga poziom ponad 80%.The main advantage of the invention is the preparation, under mild conditions, of 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-α, 3-dihydroochalcone as the main product reaction in the Absidia coerulea culture. The reaction efficiency reaches over 80%.

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 Absidia coerulea AM93. Po 6 dniach wzrostu drobnoustrojów w temperaturze 26°C i przy ciągłym wstrząsaniu, dodaje się 15 mg 4,2’,4'-trihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkonu, 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 24,16 mg surowego ekstraktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chloroform : metanol w stosunku objętościowym 1:1. Po oczyszczeniu otrzymuje się 18,30 mg 4'-O-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3''-metylobutylo]-6'-metoksy-a,3-dihydrochalkonu, o wzorze 2 z wydajnością 84%.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 fungus Absidia coerulea AM93. After 6 days of microbial growth at 26 ° C and with continuous shaking, 15 mg of 4,2 ', 4'-trihydroxy-3' - [3-methylbutyl] -6'-methoxy-a, 3-dihydroochalcone are added, formula 1, dissolved in 1.5 cm 3 of dimethyl sulfoxide. The transformation is carried out under continuous shaking for 10 days. After this time, the culture is acidified with 1-molar hydrochloric acid to pH 4.5. Then, the resulting transformation solution was extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 24.16 mg of crude extract is obtained which is purified by chromatography using 1: 1 by volume chloroform: methanol as the eluent. After purification, 18.30 mg of 4'-O-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3' -methylbutyl] -6'-methoxy-a, 3-dihydroochalcone of the formula 2 at 84% efficiency.

Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:

1H NMR (600 MHz, aceton-d6) δ: 0,92 (3H, d, J = 6,6 Hz, H-4''), 0,93 (3H, d, J = 5,4 Hz, H-5''), 1,35-1,42 (2H, m, H-2''), 1,57 (1H, m, H-3), 2,58 (1H, m, H-1''a), 2,68 (1H, m, H-1''b), 2,86 (2H, m, H-β), 3,28 (2H, m, H-a), 3,39 (1H, m, H-4'), 3,54 (2H, m, H-2''', H-3'''), 3,60 (1H, m, H-5'''), 3,66 (1H, m, H-6'''a), 3,92 (3H, s, C6'-OCH3), 3,94 (1H, m, H-6'''b), 5,09 (1H, d, J = 7,2 Hz, H-1'''), 6,47 (1H, s, H-5'), 6,75 (2H, m, J = 8,3 Hz, H-3, H-5), 7,08 (2H, m, J = 8,3 Hz, H-2, H-6), 14,03 (C2'-OH). 1 H NMR (600 MHz, acetone-d6) δ: 0.92 (3H, d, J = 6.6 Hz, H-4 "), 0.93 (3H, d, J = 5.4 Hz, H-5 "), 1.35-1.42 (2H, m, H-2"), 1.57 (1H, m, H-3), 2.58 (1H, m, H-1 'a), 2.68 (1H, m, H-1''b), 2.86 (2H, m, H-β), 3.28 (2H, m, Ha), 3.39 (1H , m, H-4 '), 3.54 (2H, m, H-2 "", H-3 ""), 3.60 (1H, m, H-5 ""), 3, 66 (1H, m, H-6 "a), 3.92 (3H, s, C6'-OCH3), 3.94 (1H, m, H-6""b), 5.09 ( 1H, d, J = 7.2Hz, H-1 ""), 6.47 (1H, s, H-5 '), 6.75 (2H, m, J = 8.3Hz, H- 3, H-5), 7.08 (2H, m, J = 8.3 Hz, H-2, H-6), 14.03 (C2'-OH).

13C NMR (150 MHz, aceton-d6) δ: 20,89 (C-1''), 22,94 (C-5), 23,04 (C-4), 28,90 (C-3), 30,36 (C-β), 38,94 (C-2), 47,21 (C-a), 56,15 (C6'-OCH3), 62,77 (C-6'''), 71,54 (C-4'''), 74,60 (C-2'''), 78,32 (3'''), 78,38 (C-5'''), 91,09 (C-5'), 101,43 (C-1'''), 106,86 (C-1'), 112,30 (C-3'), 115,99 (C-3, C-5), 130,15 (C-2, C-6), 133,24 (C-1), 156,41 (C-4), 162,02 (C-6'), 162,58 (C-4'), 164.55 (C-2'), 206,50 (C=O). 13 C NMR (150 MHz, acetone-d6) δ: 20.89 (C-1 "), 22.94 (C-5), 23.04 (C-4), 28.90 (C-3) , 30.36 (C-β), 38.94 (C-2), 47.21 (Ca), 56.15 (C6'-OCH3), 62.77 (C-6 ""), 71, 54 (C-4 ""), 74.60 (C-2 ""), 78.32 (3 ""), 78.38 (C-5 ""), 91.09 (C- 5 '), 101.43 (C-1''), 106.86 (C-1'), 112.30 (C-3 '), 115.99 (C-3, C-5), 130 , 15 (C-2, C-6), 133.24 (C-1), 156.41 (C-4), 162.02 (C-6 '), 162.58 (C-4'), 164.55 (C-2 '), 206.50 (C = O).

PL 234 085 Β1PL 234 085 Β1

Claims (4)

Zastrzeżenia patentowePatent claims 1. 4'-0-3-D-glukopiranozylo-4,2'-dihydroksy-3’-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkon, o wzorze 2.1. 4'-0-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-a, 3-dihydroochalcone of formula 2. 2. Sposób otrzymywania 4'-0-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkonu, znamienny tym, że na drodze reakcji mikrobiologicznej transformacji substratu, którym jest 4,2',4'-trihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkon o wzorze 1, otrzymuje się w 4'-0-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6'-metoksy-a,3-dihydrochalkon o wzorze 2, w taki sposób, że grzyby z gatunku Absidia coerulea, namnaża się w płynnym podłożu mikrobiologicznym, charakterystycznym dla grzybów strzępkowych, przy ciągłym mieszaniu reagentów, w temperaturze 12-40°C, po czym po upływie od 3 do 7 dni, do narośniętej hodowli dodaje się substrat i dalej prowadzi proces, aż do całkowitego zużycia substratu, po czym po zakończeniu transformacji roztwór transformacyjny ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą, oddziela frakcję organiczną, odwadnia, odparowuje rozpuszczalnik i tak otrzymany surowy produkt oczyszcza się za pomocą technik chromatograficznych, w wyniku czego otrzymuje się czysty produkt, którym jest 4'-0-3-D-glukopiranozylo-4,2'-dihydroksy-3'-[3-metylobutylo]-6-metoksy-α,β-dihydrochalkon.2. The method of obtaining 4'-0-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-a, 3-dihydroochalcone, characterized by the fact that by means of a microbiological reaction transformation of substrate 4,2 ', 4'-trihydroxy-3' - [3-methylbutyl] -6'-methoxy-a, 3-dihydroochalcone of formula 1, is obtained in 4'-0-3-D- glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6'-methoxy-a, 3-dihydrochalcone of the formula II, such that the fungi of the genus Absidia coerulea are multiplied in a liquid microbial medium, characteristic for filamentous fungi, with constant stirring of the reagents at a temperature of 12-40 ° C, then after 3 to 7 days, the substrate is added to the grown culture and the process is continued until the substrate is completely consumed, and then after the transformation is completed the transformation solution is extracted with a water-immiscible organic solvent, the organic fraction is separated, dehydrated, the solvent is evaporated off and the crude product thus obtained is purified by chromatographic techniques to give pure product which is 4'-0-3-D-glucopyranosyl-4,2'-dihydroxy-3 '- [3-methylbutyl] -6-methoxy-α, β-dihydroochalcone . 3. Sposób według zastrz. 2, znamienny tym, że grzybem jest Absidia coerulea AM93.3. The method according to p. The mushroom of claim 2, wherein the fungus is Absidia coerulea AM93. 4. Sposób według zastrz. 2, znamienny tym, że proces prowadzi się w temperaturze 26°C.4. The method according to p. The process of claim 2, wherein the process is carried out at a temperature of 26 ° C.
PL418557A 2016-09-05 2016-09-05 4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone and method for obtaining 4'-O-β-D-glucopyranosyl-4,2'-dihydroxy-3'-[3"-methylbutyl]-6'-methoxy-α,β-dihydrochalcone PL234085B1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL440842A1 (en) * 2022-04-01 2023-10-02 Uniwersytet Przyrodniczy we Wrocławiu 2'-Hydroxy-4-methyl-5'-O-β-D-(4''-O-methylglucopyranosyl)-dihydrochalcone and method for preparing 2'-hydroxy-4-methyl-5'-O-β-D- (4''-O-methylglucopyranosyl)-dihydrochalcone
PL440843A1 (en) * 2022-04-01 2023-10-02 Uniwersytet Przyrodniczy we Wrocławiu 4-Hydroxymethyl-2'-O-β-D-(4''-O-methylglucopyranosyl)-dihydrochalcone and method of preparing 4-hydroxymethyl-2'-O-β-D-(4''-O-methylglucopyranosyl)- dihydrochalcone

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL440842A1 (en) * 2022-04-01 2023-10-02 Uniwersytet Przyrodniczy we Wrocławiu 2'-Hydroxy-4-methyl-5'-O-β-D-(4''-O-methylglucopyranosyl)-dihydrochalcone and method for preparing 2'-hydroxy-4-methyl-5'-O-β-D- (4''-O-methylglucopyranosyl)-dihydrochalcone
PL440843A1 (en) * 2022-04-01 2023-10-02 Uniwersytet Przyrodniczy we Wrocławiu 4-Hydroxymethyl-2'-O-β-D-(4''-O-methylglucopyranosyl)-dihydrochalcone and method of preparing 4-hydroxymethyl-2'-O-β-D-(4''-O-methylglucopyranosyl)- dihydrochalcone

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