PL221630B1 - Process for preparing 4-hydroxydihydrojasmone of antifidant activity - Google Patents
Process for preparing 4-hydroxydihydrojasmone of antifidant activityInfo
- Publication number
- PL221630B1 PL221630B1 PL407371A PL40737114A PL221630B1 PL 221630 B1 PL221630 B1 PL 221630B1 PL 407371 A PL407371 A PL 407371A PL 40737114 A PL40737114 A PL 40737114A PL 221630 B1 PL221630 B1 PL 221630B1
- Authority
- PL
- Poland
- Prior art keywords
- hydroxydihydrojasmone
- preparing
- formula
- activity
- carried out
- Prior art date
Links
- 230000000694 effects Effects 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 10
- 230000009466 transformation Effects 0.000 claims description 5
- 241000235555 Cunninghamella Species 0.000 claims description 3
- 244000184734 Pyrus japonica Species 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- YCIXWYOBMVNGTB-UHFFFAOYSA-N 3-methyl-2-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1=C(C)CCC1=O YCIXWYOBMVNGTB-UHFFFAOYSA-N 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 241000721621 Myzus persicae Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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
- 241000238631 Hexapoda Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000012451 post-reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób otrzymywania 4-hydroksydihydrojasmonu o aktywności antyfidantnej.The subject of the invention is a method for the preparation of 4-hydroxydihydrojasmone with antifungal activity.
Wynalazek może znaleźć zastosowanie w przemyśle chemicznym i rolnictwie, do wytwarzania środków ochrony roślin, deterentów pokarmowych w stosunku do szkodliwych gatunków owadów.The invention may find application in the chemical industry and agriculture, for the production of plant protection products, food retailers in relation to harmful insect species.
Dotychczas znany jest sposób otrzymywania 4-hydroksydihydrojasmonu na drodze syntezy chemicznej (Wenkert E. et al, Journal of Organic Chemistry, 50 (24), 4681-5; 1985).A method for the preparation of 4-hydroxydihydrojasmon by chemical synthesis is known to date (Wenkert E. et al, Journal of Organic Chemistry, 50 (24), 4681-5; 1985).
Istotą sposobu otrzymywania 4-hydroksydihydrojasmonu jest to, że otrzymuje się go w wyniku mikrobiologicznej transformacji dihydrojasmonu, prowadzonej za pomocą kultury szczepu grzyba Cunninghamella japonica AM472, w wyniku działania układu enzymatycznego zawartego w komórkach tego grzyba, przy ciągłym mieszaniu reagentów. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu przez ekstrakcję rozpuszczalnikiem organicznym.The essence of the method of obtaining 4-hydroxydihydrojasmonium is that it is obtained as a result of microbial transformation of dihydrojasmon, carried out with the culture of the fungus Cunninghamella japonica AM472, as a result of the enzymatic system contained in the cells of this fungus, with constant mixing of the reagents. The product obtained in this way is separated from the aqueous culture of the microorganism by extraction with an organic solvent.
Korzystne jest, gdy proces prowadzi się w temperaturze od 18°C do 30°C.It is advantageous if the temperature is between 18 ° C and 30 ° C.
Zasadniczą zaletą metody otrzymywania wspomnianego 4-hydroksydihydrojasmonu jest to, że otrzymuje się go w łagodnych warunkach, jako jedyny produkt mikrobiologicznej transformacji dihydrojasmonu z 20%-ową wydajnością i nadmiarem enancjomerycznym ee = 58% jako izomer (+).The main advantage of the method of obtaining said 4-hydroxydihydrojasmone is that it is obtained under mild conditions as the only product of microbial transformation of dihydrojasmone with 20% yield and ee = 58% ee as the (+) isomer.
4-hydroksydihydrojasmon, o wzorze 2, posiada aktywność antyfidantną w stosunku do mszycy brzoskwiniowo-ziemniaczanej (Myzus persicae SuIz).4-hydroxydihydrojasmon, of formula 2, has antifidus activity against the peach potato aphid (Myzus persicae SuIz).
Wyniki testów biologicznych w stosunku do mszycy brzoskwiniowo ziemniaczanej (Myzus persicae Sulz), przeprowadzonych według metody opisanej przez K. Dancewicz i współpracowników (Journal of Chemical Ecology, 2008, 34, 530-538), przedstawiono w tabeli 1.The results of biological tests against the peach potato aphid (Myzus persicae Sulz), carried out according to the method described by K. Dancewicz et al. (Journal of Chemical Ecology, 2008, 34, 530-538), are presented in Table 1.
T a b e l a 1T a b e l a 1
Wyniki aktywności deterentnej 4-hydroksydihydrojasmonu, o wzorze 2, w stosunku do mszycy brzoskwiniowo-ziemniaczanej (Myzus persicae Sulz)Results of the deterential activity of 4-hydroxydihydrojasmonu, of formula 2, in relation to the peach-potato aphid (Myzus persicae Sulz)
K - średnia liczba mszyc znajdująca się na połowie liścia zwilżonej 70% roztworem etanolu,K - the average number of aphids on a half of the leaf moistened with a 70% ethanol solution,
T - średnia liczba mszyc znajdująca się na połowie liścia zwilżonej 0,1% etanolowym roztworem badanego związku, P - poziom istotności różnicy statystycznej.T - the average number of aphids on a half of the leaf moistened with 0.1% ethanol solution of the tested compound, P - the level of statistical difference.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d 1 3 Example 1 3
Do 3 kolb o pojemności 2 L, w których znajduje się po 500 cm3 sterylnego podłoża, zawierającego: 15 g glukozy i 5 g aminobaku wprowadza się szczep Cunninghamella japonica AM472. Po czte3 rech dniach wzrostu dodaje się 150 mg dihydrojasmonu, o wzorze 1 (50 mg/500 cm3 pożywki) roz3 puszczonego w 15 cm3 acetonu. Transformację prowadzi się w temperaturze około 295K, przy ciągłym wstrząsaniu, przez 2 dni. Następnie, roztwór potransformacyjny ekstrahuje się trzykrotnie chlorkiem metylenu, ekstrakt suszy bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymaną mieszaninę poreakcyjną produktu 4-hydroksydihydrojasmonu, o wzorze 2, wraz z metabolitami własnymi szczepu grzyba oczyszcza się chromatograficznie na żelu krzemionkowym, używając jako eluent mieszaniny heksan:aceton, w stosunku objętościowym 2:1. Na tej drodze otrzymuje się 32 mg znanego 4-hydroksydihydrojasmonu o wzorze 2, z wydajnością 20% z nadmiarem enancjomerycznym 58% jako izomer (+).The Cunninghamella japonica AM472 strain is introduced into 3 2 L flasks , each containing 500 cm 3 of sterile medium containing: 15 g of glucose and 5 g of aminobac. After czte rech 3 days growth, 150 mg dihydrojasmonu of formula 1 (50 mg / 500 cm 3 of medium) was spread puszczonego 3 in 15 cm 3 of acetone. The transformation is carried out at about 295K with continuous shaking for 2 days. Then, the post-transformation solution was extracted three times with methylene chloride, the extract was dried with anhydrous magnesium sulfate and the solvent was evaporated. The obtained post-reaction mixture of the 4-hydroxydihydrojasmone product of formula 2 together with the own metabolites of the fungus strain is purified by chromatography on silica gel using a 2: 1 v / v hexane: acetone mixture as eluent. In this way, 32 mg of the known 4-hydroxydihydrojasmone of the formula II are obtained in a yield of 20% with an ee of 58% as the (+) isomer.
Uzyskany 4-hydroksydihydrojasmon o wzorze 2 charakteryzuje się następującymi danymi spektroskopowymi:The obtained 4-hydroxydihydrojasmon of formula 2 is characterized by the following spectroscopic data:
1H NMR (CDCI3), δ: 0,86 (t, J = 7,1 Hz, 3H, CH3-10), 1,16-1,43 (m, 6H, CH2-7, CH2-8, CH2-9), 2,07 (s, 3H, CH3-11), 2,14-2,19 (m, 2H, CH2-6), 2,26 (dd, J = 18,4 i 1,9 Hz, jeden z CH2-5), 2,75 (dd, J = 18,4 i 6,2 Hz, jeden z CH2-5), 4,71 (d, J = 6,2 Hz, 1H, H-4); 1 H NMR (CDCl3), δ: 0.86 (t, J = 7.1 Hz, 3H, CH3-10), 1,16-1,43 (m, 6H, CH2 -7, CH2 -8 , CH 2 -9), 2.07 (s, 3H, CH3-11), 2.14-2.19 (m, 2H, CH2-6), 2.26 (dd, J = 18.4 and 1 , 9 Hz, one with CH2-5), 2.75 (dd, J = 18.4 and 6.2 Hz, one with CH 2 -5), 4.71 (d, J = 6.2 Hz, 1H , H-4);
13C NMR (CDCI3), δ: 13,66 (C-11), 14,03 (C-10), 22,50 (C-6), 22,97 (C-9), 27,87 (C-8), 31,81 (C-7), 44,42 (C-5), 71,64 (C-4), 142,47 (C-2), 168,36 (C-3), 205,53 (C-1); 13 C NMR (CDCl3), δ: 13.66 (C-11), 14.03 (C-10), 22.50 (C-6), 22.97 (C-9), 27.87 (C -8), 31.81 (C-7), 44.42 (C-5), 71.64 (C-4), 142.47 (C-2), 168.36 (C-3), 205 . 53 (C-1);
IR (film, cm-1): 3403 (s), 1690 (s).IR (movie, cm -1 ): 3403 (s), 1690 (s).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL407371A PL221630B1 (en) | 2014-03-03 | 2014-03-03 | Process for preparing 4-hydroxydihydrojasmone of antifidant activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL407371A PL221630B1 (en) | 2014-03-03 | 2014-03-03 | Process for preparing 4-hydroxydihydrojasmone of antifidant activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL407371A1 PL407371A1 (en) | 2014-11-24 |
| PL221630B1 true PL221630B1 (en) | 2016-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL407371A PL221630B1 (en) | 2014-03-03 | 2014-03-03 | Process for preparing 4-hydroxydihydrojasmone of antifidant activity |
Country Status (1)
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- 2014-03-03 PL PL407371A patent/PL221630B1/en unknown
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| Publication number | Publication date |
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| PL407371A1 (en) | 2014-11-24 |
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