Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer
Hydrolysis of (±)-β-aryl-γ-ethylidene-γ-lactones by fungal strain Aspergillus ochraceus AM370 afforded (−)-(S)-γ-ethylidene-γ-lactones 2a–d and (+)-(R)-γ-ketoacids 3a–d. Enantiomeric purity of the unr...
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| Format: | Article |
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MDPI AG
2018-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/7/1516 |
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| author | Andrzej Skrobiszewski Witold Gładkowski Marcelina Mazur Maryla Szczepanik Gabriela Maciejewska Czesław Wawrzeńczyk |
| author_facet | Andrzej Skrobiszewski Witold Gładkowski Marcelina Mazur Maryla Szczepanik Gabriela Maciejewska Czesław Wawrzeńczyk |
| author_sort | Andrzej Skrobiszewski |
| collection | DOAJ |
| description | Hydrolysis of (±)-β-aryl-γ-ethylidene-γ-lactones by fungal strain Aspergillus ochraceus AM370 afforded (−)-(S)-γ-ethylidene-γ-lactones 2a–d and (+)-(R)-γ-ketoacids 3a–d. Enantiomeric purity of the unreacted lactones was strictly related to a size of an aryl substituent at C-4 of γ-lactone ring, with the highest ee (77%) obtained for the (−)-(S)-γ-ethylidene-γ-lactone possessing unsubstituted benzene ring (2a) and the lowest one (15%) determined for the (−)-(S)-γ-ethylidene-γ-lactone with bulky 1,3-benzodioxole system (2d). Lactones 2a–d, both racemic and enantiomerically enriched, as well as products of their hydrolysis showed varying degrees of feeding deterrent activity against lesser mealworm, Alphitobius diaperinus Panzer, which depended on the structure of the compound and the developmental stage of the lesser mealworm. In the case of adults, more active were γ-lactones 2a–d, compared with ketoacids 3a–d. Only in the case of lactone 2a was the effect of configuration of stereogenic center on the activity found. Particularly strong deterrents against this stage (T > 180) were racemic and (−)-(S)-γ-ethylidene-γ-lactone with p-methoxysubstituted phenyl ring (2c). |
| first_indexed | 2024-04-13T17:20:58Z |
| format | Article |
| id | doaj.art-f6c9765920a3469caa345ad136e7357c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T17:20:58Z |
| publishDate | 2018-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f6c9765920a3469caa345ad136e7357c2022-12-22T02:38:00ZengMDPI AGMolecules1420-30492018-06-01237151610.3390/molecules23071516molecules23071516Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus PanzerAndrzej Skrobiszewski0Witold Gładkowski1Marcelina Mazur2Maryla Szczepanik3Gabriela Maciejewska4Czesław Wawrzeńczyk5Department of Chemistry, Wroclaw University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Invertebrate Zoology, Nicolaus Copernicus University, 87-100 Toruń, PolandCentral Laboratory of the Instrumental Analysis, Wroclaw University of Technology, 50-370 Wroclaw, PolandDepartment of Chemistry, Wroclaw University of Environmental and Life Sciences, 50-375 Wrocław, PolandHydrolysis of (±)-β-aryl-γ-ethylidene-γ-lactones by fungal strain Aspergillus ochraceus AM370 afforded (−)-(S)-γ-ethylidene-γ-lactones 2a–d and (+)-(R)-γ-ketoacids 3a–d. Enantiomeric purity of the unreacted lactones was strictly related to a size of an aryl substituent at C-4 of γ-lactone ring, with the highest ee (77%) obtained for the (−)-(S)-γ-ethylidene-γ-lactone possessing unsubstituted benzene ring (2a) and the lowest one (15%) determined for the (−)-(S)-γ-ethylidene-γ-lactone with bulky 1,3-benzodioxole system (2d). Lactones 2a–d, both racemic and enantiomerically enriched, as well as products of their hydrolysis showed varying degrees of feeding deterrent activity against lesser mealworm, Alphitobius diaperinus Panzer, which depended on the structure of the compound and the developmental stage of the lesser mealworm. In the case of adults, more active were γ-lactones 2a–d, compared with ketoacids 3a–d. Only in the case of lactone 2a was the effect of configuration of stereogenic center on the activity found. Particularly strong deterrents against this stage (T > 180) were racemic and (−)-(S)-γ-ethylidene-γ-lactone with p-methoxysubstituted phenyl ring (2c).http://www.mdpi.com/1420-3049/23/7/1516unsaturated lactoneskinetic resolutionmicrobial hydrolysisantifeedant activity |
| spellingShingle | Andrzej Skrobiszewski Witold Gładkowski Marcelina Mazur Maryla Szczepanik Gabriela Maciejewska Czesław Wawrzeńczyk Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer Molecules unsaturated lactones kinetic resolution microbial hydrolysis antifeedant activity |
| title | Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer |
| title_full | Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer |
| title_fullStr | Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer |
| title_full_unstemmed | Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer |
| title_short | Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer |
| title_sort | microbial hydrolysis of racemic β aryl γ ethylidene γ lactones and antifeedant activity of the products against alphitobius diaperinus panzer |
| topic | unsaturated lactones kinetic resolution microbial hydrolysis antifeedant activity |
| url | http://www.mdpi.com/1420-3049/23/7/1516 |
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