PL210085B1 - The manner of production of 3'-(3''-methylo-3''-hydroxybuthylo)-2',4,4'-trihydroxy-6'-methoxychalcone - Google Patents
The manner of production of 3'-(3''-methylo-3''-hydroxybuthylo)-2',4,4'-trihydroxy-6'-methoxychalconeInfo
- Publication number
- PL210085B1 PL210085B1 PL385441A PL38544108A PL210085B1 PL 210085 B1 PL210085 B1 PL 210085B1 PL 385441 A PL385441 A PL 385441A PL 38544108 A PL38544108 A PL 38544108A PL 210085 B1 PL210085 B1 PL 210085B1
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- Poland
- Prior art keywords
- methoxychalcone
- trihydroxy
- hydroxybuthylo
- methylo
- production
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania 3'-(3-metylo-3-hydroksybutylo)-2',4,4'-trihydroksy-6'-metoksychalkonu, o wzorze 2 przedstawionym na rysunku.The present invention relates to a process for the preparation of 3 '- (3-methyl-3-hydroxybutyl) -2', 4,4'-trihydroxy-6'-methoxychalcone of the formula 2 shown in the drawing.
Związek ten jest biologicznie czynny i może znaleźć zastosowanie w przemyśle spożywczym i farmaceutycznym.This compound is biologically active and can be used in the food and pharmaceutical industries.
Związek ten izolowano wcześniej z odchodów szczurów karmionych ksantohumolem (Nookandeh, A., Frank, N., Steiner, F., Ellinger, R., Schneider, B., Gerhauser, C, Becker, H., 2004. Xanthohumol metabolites in faeces of rats. Phytochemistry 65. ss. 561-570).This compound was previously isolated from the feces of rats fed with xanthohumol (Nookandeh, A., Frank, N., Steiner, F., Ellinger, R., Schneider, B., Gerhauser, C, Becker, H., 2004. Xanthohumol metabolites in faeces of rats. Phytochemistry 65. pp. 561-570).
Wynalazek dotyczy sposobu wytwarzania 3'-(3-metylo-3-hydroksybutylo)-2',4,4'-trihydroksy-6'-metoksychalkonu, o wzorze 2, z substratu, którym jest ksantohumol.The invention relates to a process for the preparation of 3 '- (3-methyl-3-hydroxybutyl) -2', 4,4'-trihydroxy-6'-methoxychalcone of formula 2 from the substrate xanthohumol.
Istota wynalazku polega na tym, że substrat, którym jest ksantohumol, poddaje się biotransformacji kulturą grzybów z gatunku Pezicula cinnamomea.The essence of the invention consists in that the substrate, which is xanthohumol, is biotransformed with a culture of fungi of the species Pezicula cinnamomea.
Korzystnie jest, gdy reakcję prowadzi się wodną kulturą, przy ciągłym mieszaniu reagentów, w temperaturze 285-313 K.It is advantageous if the reaction is carried out in an aqueous culture with continuous mixing of the reactants, at a temperature of 285-313 K.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultury Pezicula cinnamomea, następuje reakcja addycji cząsteczki wody do wiązania olefmowego grupy prenylowej. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję octanem etylu.By following the invention, as a result of the action of the enzyme system contained in the living cells of the Pezicula cinnamomea culture, there is an addition reaction of a water molecule to the olefin bond of the prenyl group. The product thus obtained is isolated in a known manner from the aqueous culture of the microorganism by extraction with ethyl acetate.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach, 3'-(3-metylo-3-hydroksybutylo)-2',4,4'-trihydroksy-6'-metoksychalkonu, jako głównego produktu reakcji, z wydajnością 53,3%.The main advantage of the invention is to obtain, under mild conditions, 3 '- (3-methyl-3-hydroxybutyl) -2', 4,4'-trihydroxy-6'-methoxychalcone as the main reaction product with a yield of 53.3%.
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 które znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku, wprowadza się grzyby Pezicula cinnamomea. Po 2 dniach wzrostu drobnoustrojów w temperaturze około 300 K i przy ciągłym wstrząsaniu, dodaje się 30 mg ksantoliumolu, o wzorze 1, rozpuszczonego w 1,5 cm3 acetonu. Transformację prowadzi się przy ciągłym wstrząsaniu przez około 9 dób. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 34 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaniny chloroform - metanol w stosunku 9:1.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 introduced fungi Pezicula cinnamomea. After 2 days of microbial growth at a temperature of about 300 K and with continuous shaking, 30 mg of xantoliumol, formula I, dissolved in 1.5 cm 3 of acetone, are added. The transformation is carried out under continuous shaking for approximately 9 days. Thereafter, the resulting transformation solution was extracted three times with ethyl acetate, dried with magnesium sulfate and the solvent was evaporated. 34 mg of crude product are obtained, which product is purified by chromatography using a 9: 1 mixture of chloroform-methanol as eluent.
Na tej drodze otrzymuje się 15,98 mg 3'-(3-metylo-3-hydroksybutylo)-2',4,4'-trihydroksy-6'-metoksychalkonu (wydajność 53,3%).In this way, 15.98 mg of 3 '- (3-methyl-3-hydroxybutyl) -2', 4,4'-trihydroxy-6'-methoxychalcone are obtained (53.3% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi: 1H NMR: δ = 14,61 (1H, s, 2'-0H); 10,47 (1H, s, 4-OH); 10,07 (1H, s, 4'-0H); 7,78 (1H, d, J = 15,5 Hz, Ha C=O); 7,68 (1H, d, J= 15,5 Hz, He C=O); 7,58 (2H, d, J = 8,6 Hz, H-2, H-6); 6,85 (2H, d, J = 8,6 Hz, H-3, H-5); 6,10 (1H, s, H-5'); 4,14 (1H, 5, 3-OH); 3,94 (3H, 5, C6'-O-Me); 2,49 (2H, m, H-1); 1,48 (2H, m, H-2); 1,14 (6H, 5, H-4, H-5).The resulting product is characterized by the following spectral data: 1 H NMR: δ = 14.61 (1H, s, 2'-0H); 10.47 (1H, s, 4-OH); 10.07 (1H, s, 4'-OH); 7.78 (1H, d, J = 15.5Hz, Ha C = O); 7.68 (1H, d, J = 15.5 Hz, He C = O); 7.58 (2H, d, J = 8.6Hz, H -2, H-6); 6.85 (2H, d, J = 8.6 Hz, H-3, H-5); 6.10 (1H, s, H-5 '); 4.14 (1H, 5,3-OH); 3.94 (3H, 5, C6'-O-Me); 2.49 (2H, m, H -1); 1.48 (2H, m, H -2); 1.14 (6H, 5, H-4, H-5).
13C NMR: 6 = 192,2 (C=O); 165,2 (C-2'); 163,0 (C-4'); 160,8 (C-6'); 160,4 (C-4); 142,9 (C-β); 131,0 (C-2, C-6); 126,6 (C-1); 124,4 (C-α); 116,5 (C-3, C-5); 109,0 (C-3'); 105,0 (C-1'); 91,4 (C-5'); 69,5 (C-3); 56,2 (C6'-O-Me); 43,1 (C-2); 29,6 (C-4, C-5); 17,7 (C-1). 13 C NMR:? = 192.2 (C = O); 165.2 (C-2 '); 163.0 (C-4 '); 160.8 (C-6 '); 160.4 (C-4); 142.9 (C-β); 131.0 (C-2. C-6); 126.6 (C-1); 124.4 (C-α); 116.5 (C-3, C-5); 109.0 (C-3 '); 105.0 (C-1 '); 91.4 (C-5 '); 69.5 (C-3); 56.2 (C6'-O-Me); 43.1 (C-2); 29.6 (C-4, C-5); 17.7 (C-1).
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL385441A PL210085B1 (en) | 2008-06-16 | 2008-06-16 | The manner of production of 3'-(3''-methylo-3''-hydroxybuthylo)-2',4,4'-trihydroxy-6'-methoxychalcone |
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| Application Number | Priority Date | Filing Date | Title |
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| PL385441A PL210085B1 (en) | 2008-06-16 | 2008-06-16 | The manner of production of 3'-(3''-methylo-3''-hydroxybuthylo)-2',4,4'-trihydroxy-6'-methoxychalcone |
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| PL385441A1 PL385441A1 (en) | 2008-12-08 |
| PL210085B1 true PL210085B1 (en) | 2011-12-30 |
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