tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion
Abstract
:1. Introduction
2. Results
2.1. Process of Purification
2.2. Structural Elucidation
2.3. Supplementation Assays
2.4. Cytotoxic Activity
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Collection and Phylogenetic Analysis of PC-GYM-TO Strain
3.3. Cultivation and Extraction
3.4. Purification and Isolation
3.5. Molecular Models and Dynamic Simulations
3.6. Cytotoxicity Assays
3.7. DNA Damage Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the Compounds 1, 2 are available from the authors. |
Compound 1 | Standard Santonox | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Position | δC, ppm | δH, (ppm) mult. (J in Hz) | HMBC (H → C) | COSY | NOESY | Position | δC, ppm | δH, (ppm) mult. (J in Hz) | HMBC (H → C) | COSY | NOESY |
1/1′ | 153.4 | - | - | - | 1/1′ | 153.2 | - | - | - | - | |
2/2′ | 134.6 | - | - | - | 2/2′ | 134.5 | - | - | - | - | |
3/3′ | 130.8 | 7.00, s | 1, 4, 5, 8 | 7, 9/10/11 | 9/10/11 | 3/3′ | 130.6 | 7.00, s | 1, 4, 5, 6, 7, 8 | 7, 9/10/11 | 9/10/11 |
4/4′ | 125.5 | - | - | - | 4/4′ | 137.7 | - | - | - | - | |
5/5′ | 137.8 | - | - | - | 5/5′ | 125.4 | - | - | - | - | |
6/6′ | 118.8 | 6.56, s | 1, 2, 4, 7 | 7 | 6/6′ | 118.7 | 6.54, s | 1, 4, 5, 7, 8 | 7 | 7 | |
7/7′ | 19.8 | 2.28, s | 4, 5, 6 | 3, 6 | 7/7′ | 19.7 | 2.27, s | 4, 5, 6 | 3, 6 | 6 | |
8/8′ | 34.4 | - | - | 8/8′ | 34.3 | - | - | - | |||
9, 10, 11 /9′,10, 11′ | 29.7 | 1.28, s | 9/10/11, 2, 8 | 3 | 3 | 9, 10, 11/9′,10, 11′ | 29.5 | 1.28, s | 9/10/11, 2, 8 | 3 | 3 |
OH | 4.72, br | - | OH |
Compound 2 | |||||
---|---|---|---|---|---|
Position | δC | Type | δH, mult. (J in Hz) | COSY | HMBC (H → C) |
1′ | 152.1 | C | - | - | |
2′ | 135.8 | C | - | - | |
3′ | 124.8 | CH | 6.99, s | 1′, 5′, 12′ | |
4′ | 131.1 | C | - | ||
5′ | 124.8 | CH | 6.99, s | 1′, 3′, 1, 8′ | |
6′ | 135.8 | C | - | ||
1 | 31.0 | CH2 | 2.85, dd (9.1, 6.9) | 2 | 3′/5′, 4′, 2, 3 |
2 | 36.5 | CH2 | 2.60, dd (9.1, 6.9) | 1 | 5′, 1, 3 |
3 | 173.4 | C | - | ||
1″ | 64.6 | CH2 | 4.07, t (6.8) | 2″ | 3, 2″, 3″ |
2″ | 29.7 | CH2 | 1.56–1.61, m | 1″, 3″ | 1″, 3″ |
3″ | 29.7 | CH2 | 1.56–1.61,m | 2″ | 2″ |
4″–17″ | 22.7–32.0 | CH2 | 1.24, m | 18″ | 5″–17″, 2″, 3″, 18″ |
18″ | 14.1 | CH3 | 0.88, t (6.7) | 17″ | 17″ |
7′/11′c | 34.3 | C | - | ||
8′,9′,10′/12′,13′,14′ a | 30.3 | CH3 | 1.43, s | 8′,9′,10′/12′,13′,14′, 7′/11′, 2′, 6′, 3′/5′ | |
OH | 5.07, bs | 1′, 2′, 6′ |
Compound | IC50 (µM) | |
---|---|---|
HaCaT | B16 | |
1 | 8.38 | 4.75 |
2 | >377.4 | 169.8 ± 1 |
Doxorubicin | 0.096 ± 0.009 | 0.034 ± 0.001 |
Concentration (µM) | γH2AX Foci/Nuclei |
---|---|
0 | 12.9 ± 0.4 |
0.1 | 12.8 ± 0.2 |
1 | 3.6 ± 0.3 |
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Nguyen, T.-B.-L.; Delalande, O.; Rouaud, I.; Ferron, S.; Chaillot, L.; Pedeux, R.; Tomasi, S. tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion. Molecules 2018, 23, 1951. https://doi.org/10.3390/molecules23081951
Nguyen T-B-L, Delalande O, Rouaud I, Ferron S, Chaillot L, Pedeux R, Tomasi S. tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion. Molecules. 2018; 23(8):1951. https://doi.org/10.3390/molecules23081951
Chicago/Turabian StyleNguyen, Thi-Bach-Le, Olivier Delalande, Isabelle Rouaud, Solenn Ferron, Laura Chaillot, Rémy Pedeux, and Sophie Tomasi. 2018. "tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion" Molecules 23, no. 8: 1951. https://doi.org/10.3390/molecules23081951