Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus †
Abstract
:1. Introduction
2. Results and Discussion
2.1. Screening Biotransformations of Oleic Acid (1)
2.2. Micrococcus Luteus PCM525 Transformations of Linoleic and α-Linolenic Acids
2.3. Micrococcus Luteus PCM525 Transformations Depending on the Growth Phase and Concentration of Oleic Acid (1)
2.4. Selection of Optimal Conditions for Biotransformations of Oleic Acid (1)
2.4.1. The Effect of Surfactants
2.4.2. The Effect of Media Aeration and Agitation
2.4.3. The Effect of Redox Potential
2.4.4. The Effect of Carbon Source and Technique of Biotransformation
3. Materials and Methods
3.1. Materials
3.2. Microorganisms
3.3. Media Composition
3.4. Biotransformation Process
3.4.1. Screening Procedure in Microtiter Plate
3.4.2. Screening Procedure in Erlenmeyer Flask
3.5. Process Optimization for Micrococcus luteus PCM525 Transformation
3.6. Preparation of Resting Cells of Micrococcus luteus PCM525
3.7. Pre-Growing of Micrococcus Luteus PCM525 in the Presence of a High Concentration of Oleic Acid (1)
3.8. Analysis
3.9. Characterization of Substrates and Products from Biotransformation Experiments
GC–MS Analysis
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the tested compounds (1,2,6) are available from the authors. |
Strain | Time (Days) | Conversion (%) | Products | |||
---|---|---|---|---|---|---|
10-HSA (2) (%) | 10-KSA (3) (%) | 4-KLA (4) (%) | GDDL (6) (%) | |||
B.benzoevorans DSM5391 | 3 | 13 | 13 | 0 | 0 | 0 |
Dietzia sp. DSM44016 | 1 | 100 | 0 | 100 | 0 | 0 |
2 | 100 | 0 | 0 * | 0 | 0 | |
M. luteus PCM525 | 1 | 100 | 0 | 83 | 12 | 5 |
5 | 100 | 0 | 0 | 50 | 50 | |
R. erythropolis DSM44534 | 1 | 100 | 0 | 100 | 0 | 0 |
6 | 100 | 0 | 0 * | 0 | 0 | |
R. ruber PCM2166 | 1 | 100 | 5 | 95 | 0 | 0 |
6 | 100 | 4 | 96 | 0 | 0 |
Surfactant | Time (Days) | Conversion (%) | Substrate | Products | ||
---|---|---|---|---|---|---|
OA (1) (%) | 10-KSA (3) (%) | 4-KLA (4) (%) | GDDL (6) (%) | |||
Glycerol | 5 | 100 | 0 | 65 (±3) * | 25 (±1) | 10 (±2) |
Triton X-100 | 5 | 100 | 0 | 62 (±4) | 30 (±2) | 8 (±2) |
Tween-80 | 5 | 98 (±2) | 2 | 93 | 3 | 2 (±2) |
No. | Additive | Time (Days) | Conversion (%) | Substrate | Products | |||
---|---|---|---|---|---|---|---|---|
OA (1) (%) | 10-KSA (3) (%) | 4-KLA (4) (%) | GDDL (6) (%) | |||||
1 | With addition of OA (1) | HCl * | 5 | 100 | 0 | 59 (±2) ** | 25 (±1) | 16 (±1) |
11 | 100 | 0 | 44 (±4) | 36 (±2) | 20 (±2) | |||
2 | Glucose | 5 | 100 | 0 | 100 | 0 | 0 | |
11 | 100 | 0 | 100 | 0 | 0 | |||
3 | HCl + Glucose | 5 | 100 | 0 | 100 | 0 | 0 | |
11 | 100 | 0 | 100 | 0 | 0 | |||
4 | When 4-KDDA (4) was formed | HCl | 5 | 100 | 0 | 48 (±3) | 33 (±2) | 19 (±1) |
11 | 100 | 0 | 19 (±2) | 54 (±1) | 27 (±3) | |||
5 | HCl + Glucose | 5 | 100 | 0 | 54 | 28 (±4) | 18 (±4) | |
11 | 100 | 0 | 25 (±1) | 47 (±2) | 28 (±3) |
No. | Substrate | Media | Time (Days) | Conversion (%) | Products | |||
---|---|---|---|---|---|---|---|---|
10-HSA (2) (%) | 10-KSA (3) (%) | 4-KLA (4) (%) | GDDL (6) (%) | |||||
1 | OA (1) | PCM | 2 | 100 | 0 | 0 | 69 (±4) * | 31 (±4) |
5 | 100 | 0 | 0 | 63 (±1) | 37 (±1) | |||
2 | PCM (no glucose) | 2 | 0 | 0 | 0 | 0 | 0 | |
6 | 0 | 0 | 0 | 0 | 0 | |||
3 | buffer | 2 | 100 | 15 (±5) | 85 (±5) | 0 | 0 | |
5 | 100 | 12 (±1) | 88 (±1) | 0 | 0 | |||
4 | 10-HSA (2) | PCM | 2 | 93 (±4) | 7 (±4) | 90 (±2) | 3 (±2) | 0 |
5 | 100 | 0 | 96 (±4) | 4 (±4) | 0 | |||
5 | PCM (no glucose) | 2 | 100 | 0 | 100 | 0 | 0 | |
6 | 100 | 0 | 100 | 0 | 0 | |||
6 | buffer | 2 | 25 (±2) | 75 (±2) | 25 (±2) | 0 | 0 | |
5 | 28 (±1) | 72 (±1) | 28 (±1) | 0 | 0 |
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Boratyński, F.; Szczepańska, E.; De Simeis, D.; Serra, S.; Brenna, E. Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus. Molecules 2020, 25, 3024. https://doi.org/10.3390/molecules25133024
Boratyński F, Szczepańska E, De Simeis D, Serra S, Brenna E. Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus. Molecules. 2020; 25(13):3024. https://doi.org/10.3390/molecules25133024
Chicago/Turabian StyleBoratyński, Filip, Ewa Szczepańska, Davide De Simeis, Stefano Serra, and Elisabetta Brenna. 2020. "Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus" Molecules 25, no. 13: 3024. https://doi.org/10.3390/molecules25133024