PL195346B1 - Method of receiving testolactone - Google Patents
Method of receiving testolactoneInfo
- Publication number
- PL195346B1 PL195346B1 PL356041A PL35604102A PL195346B1 PL 195346 B1 PL195346 B1 PL 195346B1 PL 356041 A PL356041 A PL 356041A PL 35604102 A PL35604102 A PL 35604102A PL 195346 B1 PL195346 B1 PL 195346B1
- Authority
- PL
- Poland
- Prior art keywords
- testolactone
- formula
- substrate
- lactone
- carried out
- Prior art date
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
1. Sposób wytwarzania testolaktonu, o wzorze 2, na drodze transformacji mikrobiologicznej, znamienny tym, że substrat, którym jest testosteron, o wzorze 1, utleniania się do laktonu przy pomocy systemu enzymatycznego szczepu grzyba z gatunku Penicillium lilacinum.1. A method for producing testolactone of formula 2, by microbial transformation, characterized in that the substrate is testosterone of formula I oxidizes to lactone with the help of an enzyme system a strain of the fungus Penicillium lilacinum.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób wytwarzania testolaktonu, o wzorze 2, na drodze mikrobiologicznej.The subject of the invention is a microbiological preparation of testolactone of formula II.
Związek ten jako inhibitor aromatazy, może być wykorzystany w blokowaniu konwersji androgenów do estrogenów. (E. A. Cummings, S. R. Salisbury, R. S. Rittmaster, J. Clin. Endocrinol. Metab., 1998, 83, vol. 3, ss. 784-787).As an aromatase inhibitor, this compound can be used to block the conversion of androgens to estrogens. (E. A. Cummings, S. R. Salisbury, R. S. Rittmaster, J. Clin. Endocrinol. Metab., 1998, 83, vol. 3, pp. 784-787).
Znany jest proces biotransformacji progesteronu do testolaktonu przy pomocy kultury grzyba Aspergillus oryzae, z wydajnością 37% (Mostafa, M. Eman; A. Zohri, Folia Microbiol., 2000, vol. 45 (3), ss. 243-247).It is known to biotransform progesterone into testolactone with the help of the Aspergillus oryzae mushroom culture, with an efficiency of 37% (Mostafa, M. Eman; A. Zohri, Folia Microbiol., 2000, vol. 45 (3), pp. 243-247).
Wynalazek dotyczy sposobu wytwarzania testolaktonu, o wzorze 2, przy użyciu systemu enzymatycznego mikroorganizmu.The invention relates to a process for the production of testolactone of formula 2 using the enzyme system of the microorganism.
Istota wynalazku polega na tym, że utlenianie substratu, którym jest testosteron o wzorze 1, do laktonu, o wzorze 2, prowadzi się przy pomocy kultury szczepu grzyba z gatunku Penicillium lilacinum.The essence of the invention lies in the fact that the oxidation of the testosterone substrate of the formula I to the lactone of the formula II is carried out with the aid of a culture of a fungus strain of the genus Penicillium lilacinum.
Korzystne jest, gdy proces utleniania substratu prowadzi się wodną kulturą szczepu, przy ciągłym mieszaniu reagentów, w temperaturze 291-297 K.It is advantageous if the substrate oxidation process is carried out in an aqueous strain culture, with continuous mixing of the reagents, at a temperature of 291-297 K.
W wyniku postępowania zgodnie z wynalazkiem, wskutek działania układu enzymatycznego zawartego w komórkach grzyba strzępkowego Penicillium lilacinum, następuje utlenienie substratu do laktonu. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję chloroformem.As a result of the procedure according to the invention, the substrate is oxidized to a lactone due to the action of the enzyme system contained in the cells of the filamentous fungus Penicillium lilacinum. The product obtained in this way is separated from the aqueous culture of the microorganism by a known method by extraction with chloroform.
Zasadniczą zaletą wynalazku jest otrzymanie testolaktonu, jako głównego produktu reakcji, z95% wydajnością.The main advantage of the invention is that testolactone is obtained as the main reaction product in 95% yield.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an exemplary embodiment.
Przykład. Do kolby Erlenmajera o pojemności 250 cm3, w której znajduje się 50 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1g peptobaku E, wprowadza się szczep Penicillium lilacinum. Po trzech dniach jego wzrostu dodaje się 20 mg testosteronu, o wzorze 1, rozpuszczonego w 1 cm3 acetonu. Transformację prowadzi się w temperaturze 295 K, przy ciągłym wstrząsaniu przez 96 godzin. Następnie uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie chloroformem, osusza się bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 21 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaniny chlorku metylenu-acetonu w stosunku 8:2. Na tej drodze otrzymuje się 19 mg testolaktonu (wydajność 95%).Example. Penicillium lilacinum strain is introduced into an Erlenmajer flask with a capacity of 250 cm 3 , containing 50 cm 3 of a sterile medium containing 3 g of glucose and 1 g of peptobac E. After three days of its growth, 20 mg of testosterone, formula I, dissolved in 1 cm 3 of acetone, is added. The transformation is carried out at 295 K with continuous shaking for 96 hours. The resulting transformation solution was then extracted three times with chloroform, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 21 mg of crude product are obtained which are purified by chromatography using an 8: 2 mixture of methylene chloride-acetone as eluent. In this way 19 mg of testolactone are obtained (95% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi: 1HNMR (CDCl3) d (ppm): 1,34 s (3H, H-19); 1,15 s (3H,H-18); 1,34 s (3H, H-19); 5,74 s (1H,H-4).The obtained product is characterized by the following spectral data: 1 H NMR (CDCl 3) d (ppm): 1.34 s (3H, H-19); 1.15 s (3H, H-18); 1.34 s (3H, H-19); 5.74 s (1H, H-4).
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL356041A PL195346B1 (en) | 2002-09-13 | 2002-09-13 | Method of receiving testolactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL356041A PL195346B1 (en) | 2002-09-13 | 2002-09-13 | Method of receiving testolactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL356041A1 PL356041A1 (en) | 2004-03-22 |
| PL195346B1 true PL195346B1 (en) | 2007-09-28 |
Family
ID=32090032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL356041A PL195346B1 (en) | 2002-09-13 | 2002-09-13 | Method of receiving testolactone |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL195346B1 (en) |
-
2002
- 2002-09-13 PL PL356041A patent/PL195346B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL356041A1 (en) | 2004-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LICE | Declarations of willingness to grant licence |
Effective date: 20070410 |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20050913 |