Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer
Abstract
:1. Introduction
2. Results and Discussion
2.1. Hydrolysis of Lactones 2a–d
2.2. Antifeedant Activity
3. Materials and Methods
3.1. Analysis
3.2. Chemicals
3.3. Synthesis of (−)-(S,E)-5-Ethylidene-4-(4′methylphenyl)dihydrofuran-2-one [(−)-2b]
3.4. Microorganism and Growing Medium
3.5. Screening Procedure
3.6. General Procedure for Multiplied Scale Biotransformation of Racemic γ-Lactones 2a–d and Isolation of the Products
3.7. Biotransformation of (±)-(E)-5-Ethylidene-4-phenyldihydrofuran-2-one (2a)
3.8. Biotransformation of (±)-(E)-5-Ethylidene-4-(4′-methylphenyl)dihydrofuran-2-one (2b)
3.9. Biotransformation of (±)-(E)-5-Ethylidene-4-(4′-methoxyphenyl)dihydrofuran-2-one (2c)
3.10. Biotransformation of (±)-(E)-4-(benzo[d][1,′3′]dioxol-5′-yl)-5-ethylidenedihydrofuran-2 one (2d)
3.11. Antifeedant Activity Assays
3.12. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 2a–d, (−)-2a–d and (+)-3a–d are available from the authors. |
Substrate | ||||
---|---|---|---|---|
2a | 2b | 2c | 2d | |
Conversion a [%] | 48 | 55 | 52 | 48 |
ee [%] | 77 | 56 | 22 | 15 |
Entry | Compound | Deterrence Coefficients 1 | |||||
---|---|---|---|---|---|---|---|
Larvae | Adults | ||||||
A | R | T | A | R | T | ||
1 | (±)-2a | 8.59 ± 5.63a | 64.01 ± 6.21ab | 72.60 ± 12.43a | 64.13 ± 11.44bc | 83.07 ± 3.60cd | 147.19 ± 14.07def |
2 | (±)-2b | 84.4 ± 4.49d | 78.96 ± 2.25bc | 163.36 ± 4.66b | 81.16 ± 10.67de | 72.54 ± 5.25abcd | 153.7 ± 6.68def |
3 | (±)-2c | 53.87 ± 6.71d | 90.48 ± 4.61bc | 144.35 ± 5.82ab | 91.88 ± 1.97e | 93.64 ± 0.73d | 185.52 ± 2.09ef |
4 | (±)-2d | 67.92 ± 13.34d | 96.19 ± 0.58c | 164.11 ± 11.88b | 71.12 ± 9.97de | 85.56 ± 6.81bcd | 156.67 ± 8.73def |
5 | (−)-(S)-2a | 9.33 ± 1.34a | 94.87 ± 1.52bc | 104.20 ± 3.04a | 22.47 ± 8.98a | 90.83 ± 3.58cd | 113.31 ± 12.53abc |
6 | (−)-(S)-2b | 30.15 ± 4.16ab | 70.62 ± 12.86ab | 100.76 ± 12.76a | 47.19 ± 3.48ab | 90.23 ± 2.86cd | 137.41 ± 6.85bcd |
7 | (−)-(S)-2c | 55.11 ± 12.11bcd | 85.84 ± 2.21bc | 140.95 ± 10.88b | 94.69 ± 1.64e | 94.06 ± 1.22d | 188.75 ± 1.87f |
8 | (−)-(S)-2d | 44.10 ± 2.07bc | 91.49 ± 2.19bc | 135.59 ± 1.33ab | 76.07 ± 9.66de | 94.29 ± 1.39d | 170.36 ± 9.85def |
9 | (+)-(R)-3a | 43.61 ± 3.38bc | 86.87 ± 3.78bc | 130.48 ± 5.33a | 33.12 ± 3.65ab | 75.59 ± 4.38bcd | 108.71 ± 7.34abc |
10 | (+)-(R)-3b | 82.60 ± 0.39d | 66.45 ± 7.29ab | 149.05 ± 6.32b | 29.18 ± 2.19a | 65.17 ± 5.62ab | 94.35 ± 5.92ab |
11 | (+)-(R)-3c | 59.08 ± 1.43d | 50.08 ± 5.99ab | 109.16 ± 2.14a | 30.67 ± 4.48ab | 53.16 ± 2.93a | 83.83 ± 5.61a |
12 | (+)-(R)-3d | 60.16 ± 6.23bcd | 39.59 ± 9.08a | 99.75 ± 7.51a | 31.36 ± 5.99ab | 50.22 ± 11.46a | 81.58 ± 9.25a |
13 | Azadirachtin [42] | 97.00 | 82.62 | 179.62 | 99.14 | 98.44 | 197.58 |
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Skrobiszewski, A.; Gładkowski, W.; Mazur, M.; Szczepanik, M.; Maciejewska, G.; Wawrzeńczyk, C. Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer. Molecules 2018, 23, 1516. https://doi.org/10.3390/molecules23071516
Skrobiszewski A, Gładkowski W, Mazur M, Szczepanik M, Maciejewska G, Wawrzeńczyk C. Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer. Molecules. 2018; 23(7):1516. https://doi.org/10.3390/molecules23071516
Chicago/Turabian StyleSkrobiszewski, Andrzej, Witold Gładkowski, Marcelina Mazur, Maryla Szczepanik, Gabriela Maciejewska, and Czesław Wawrzeńczyk. 2018. "Microbial Hydrolysis of Racemic β-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer" Molecules 23, no. 7: 1516. https://doi.org/10.3390/molecules23071516