Stress-Induced Production of Bioactive Oxylipins in Marine Microalgae
Abstract
:1. Introduction
2. Results
2.1. Profiles of Enzymatic and Nonenzymatic Oxygenated Metabolites in Stressed Mi124
2.1.1. Profiles of Nonenzymatic Oxygenated Metabolites
Derivatives from ARA (C20:4n−6) and DPA (C22:5n−6)
Derivatives from ALA (C18:3n−3)
Derivatives from EPA (C20:5n−3)
Derivatives from DHA (C22:6n−3)
2.1.2. Profiles of Enzymatic Oxygenated Metabolites
Derivatives of LA (C18:2n−6)
Derivatives of ARA (C20:4n−6)
Derivatives from ALA, EPA, and DHA
- (i)
- The addition of H2O2 to the culture medium seemed to induce a slight increase in the concentration of the 9(R),16(RS)-linotrin while EtOAc or NaCl would have the opposite effect;
- (ii)
- The addition of H2O2 (4 mM) would also slightly increase the concentration of 18-HEPE, a derivative of EPA;
- (iii)
- None of them appear to be produced in greater quantities when abiotic stresses are applied, since the highest concentrations for each of the metabolites appeared to be obtained with the control culture medium.
2.2. Profiles of Enzymatic and Nonenzymatic Oxygenated Metabolites in Stressed Mi136
2.2.1. Profiles of Nonenzymatic Oxygenated Metabolites
Derivatives from ARA
Derivatives from ALA
Derivatives from EPA
2.2.2. Profiles of the Enzymatic Oxygenated Metabolites
Derivatives from LA
Derivatives from ARA
Derivatives from EPA
Derivatives from DHA
2.3. Profiles of Enzymatic and Nonenzymatic Oxygenated Metabolites in Stressed Mi168
2.3.1. Nonenzymatic Oxygenated Metabolite Profiles
Derivatives from ARA
Derivatives from DPA
Derivatives from ALA
Derivatives from EPA
Derivatives from DHA
2.3.2. Enzymatic Oxygenated Metabolites Profiles
Derivatives from LA
Derivatives from ARA
Derivatives from EPA
Derivatives from DHA
3. Discussion
4. Materials and Methods
4.1. Chemicals and Reagents
4.2. Microalgal Species and Nonstressful Conditions
4.3. Viability Cell Tests
4.4. Stress Induction
4.5. Nonenzymatic Oxylipins Extraction and Analysis
4.6. Enzymatic Oxylipins Extraction and Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Conflicts of Interest
References
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Mi124 | ||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Oxylipins | Control | 1 mM of H2O2 | 4 mM of H2O2 | 0.5 mM of EtOAc | 1 mΜ of EtOAc | 45 g/L of NaCl | ||||||||||||
Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | |
9-HODE | 4.58 × 103 | ± | 3.12 × 102 | 9.14 × 103 | ± | 5.95 × 102 | 9.33 × 103 | ± | 1.87 × 103 | 3.87 × 103 | ± | 6.53 × 102 | 3.15 × 103 | ± | 8.08 × 102 | 3.09 × 103 | ± | 3.53 × 102 |
13-HODΕ | 1.38 × 104 | ± | 3.00 × 103 | 1.40 × 104 | ± | 1.76 × 103 | 1.88 × 104 | ± | 6.97 × 103 | 1.11 × 104 | ± | 5.13 × 103 | 9.71 × 103 | ± | 5.71 × 103 | 7.50 × 103 | ± | 2.08 × 103 |
5oxoETE | 3.12 × 10 | ± | 9.24 | 3.04 × 10 | ± | 2.60 × 10 | 9.28 × 10 | ± | 2.05 × 10 | 1.97 × 10 | ± | 1.47 × 10 | 1.78 × 10 | ± | 1.50 × 10 | 2.07 × 10 | ± | 8.41 |
5-HΕΤΕ | 3.95 × 10 | ± | 2.02 | 5.55 × 10 | ± | 2.54 | 1.52 × 102 | ± | 4.34 × 10 | 3.18 × 10 | ± | 1.27 × 10 | 2.11 × 10 | ± | 1.10 × 10 | 2.40 × 10 | ± | 8.37 |
8-HΕΤΕ | 2.19 × 10 | ± | 8.33 | 2.72 × 10 | ± | 2.10 | 6.46 × 10 | ± | 1.62 × 10 | 1.79 × 10 | ± | 9.25 | 1.43 × 10 | ± | 1.10 × 10 | 1.22 × 10 | ± | 2.55 |
12-HΕΤΕ | 3.18 × 10 | ± | 1.19 × 10 | 4.83 × 10 | ± | 1.14 × 10 | 1.21 × 102 | ± | 2.24 × 10 | 3.13 × 10 | ± | 2.35 × 10 | 1.88 × 10 | ± | 1.55 × 10 | 1.12 × 10 | ± | 8.60 |
15-HΕΤΕ | 4.49 × 102 | ± | 1.23 × 102 | 3.57 × 102 | ± | 1.01 × 102 | 7.76 × 102 | ± | 3.42 × 102 | 3.31 × 102 | ± | 2.03 × 102 | 2.79 × 102 | ± | 1.96 × 102 | 2.10 × 102 | ± | 8.19 × 10 |
14.15-ΕΕΤ | 2.51 × 10 | ± | 1.79 × 10 | 1.71 × 10 | ± | 1.23 × 10 | 3.66 × 10 | ± | 1.55 × 10 | 2.73 × 10 | ± | 2.10 × 10 | 1.57 × 10 | ± | 2.12 × 10 | 4.85 | ± | 6.85 |
9(R).16(R.S)-Linotrines | 4.30 × 102 | ± | 4.96 × 10 | 4.04 × 102 | ± | 9.40 × 10 | 4.24 × 102 | ± | 1.42 × 102 | 2.89 × 102 | ± | 2.19 × 10 | 1.91 × 102 | ± | 6.39 × 10 | 2.7 × 102 | ± | 6.59 × 10 |
18-HEPE | 8.55 × 102 | ± | 2.34 × 102 | 7.53 × 102 | ± | 8.60 | 1.01 × 103 | ± | 2.36 × 102 | 6.81 × 102 | ± | 2.53 × 102 | 5.87 × 102 | ± | 4.02 × 102 | 5.43 × 102 | ± | 2.08 × 102 |
ΡDx | 1.04 × 102 | ± | 5.17 × 10 | 3.83 × 10 | ± | 1.03 × 10 | 4.85 × 10 | ± | 2.48 × 10 | 8.87 × 10 | ± | 5.57 × 10 | 8.42 × 10 | ± | 9.81 × 10 | 3.15 × 10 | ± | 1.94 × 10 |
14-HDoHE | 1.07 × 104 | ± | 1.23 × 103 | 1.15 × 104 | ± | 1.39 × 103 | 1.33 × 104 | ± | 4.03 × 103 | 8.65 × 103 | ± | 3.06 × 103 | 6.27 × 103 | ± | 3.08 × 103 | 6.20 × 103 | ± | 2.22 × 103 |
17-HDoHE | 1.22 × 105 | ± | 3.81 × 104 | 9.10 × 104 | ± | 2.11 × 104 | 9.06 × 104 | ± | 3.05 × 104 | 9.31 × 104 | ± | 5.57 × 104 | 8.07 × 104 | ± | 5.98 × 104 | 6.28 × 104 | ± | 3.68 × 104 |
9-L1t-PhytoP | 65.31 | ± | 11.53 | 90.89 | ± | 7.24 | 89.25 | ± | 1.89 | 50.80 | ± | 6.89 | 66.48 | ± | 12.64 | 59.95 | ± | 8.57 |
9-F1t-PhytoP | 32.88 | ± | 2.31 | 64.26 | ± | 17.70 | 54.69 | ± | 4.54 | 28.53 | ± | 5.43 | 30.30 | ± | 1.57 | 49.25 | ± | 12.30 |
16-B1t-PhytoP | 64.90 | ± | 9.96 | 94.93 | ± | 8.60 | 92.14 | ± | 2.15 | 52.04 | ± | 6.88 | 66.24 | ± | 11.28 | 70.40 | ± | 11.31 |
16-epi-16-F1t-PhytoP | 136.68 | ± | 35.56 | 154.10 | ± | 29.85 | 166.69 | ± | 43.22 | 162.60 | ± | 12.12 | 158.19 | ± | 68.11 | 97.43 | ± | 17.70 |
16-F1t-PhytoP | 191.01 | ± | 51.00 | 202.69 | ± | 32.71 | 234.50 | ± | 66.10 | 232.24 | ± | 15.52 | 228.76 | ± | 102.82 | 132.98 | ± | 23.32 |
ent-9A-12-epi-ST-Δ10-13-PhytoF | 44.25 | ± | 13.08 | 62.05 | ± | 3.04 | 55.00 | ± | 4.73 | 33.29 | ± | 7.76 | 54.11 | ± | 14.81 | 40.92 | ± | 4.58 |
ent-9B-12-epi-ST-Δ10-13-PhytoF | 14.75 | ± | 4.45 | 20.95 | ± | 2.77 | 16.44 | ± | 1.54 | 11.42 | ± | 2.67 | 16.54 | ± | 4.35 | 19.95 | ± | 3.44 |
ent-16A-9-epi-ST-Δ14-10-PhytoF | 95.51 | ± | 31.37 | 105.70 | ± | 11.86 | 94.80 | ± | 18.53 | 66.76 | ± | 14.37 | 122.56 | ± | 47.00 | 49.93 | ± | 6.80 |
ent-16B-9-epi-ST-Δ14-10-PhytoF | 122.81 | ± | 42.73 | 131.16 | ± | 15.43 | 115.29 | ± | 22.14 | 83.16 | ± | 9.69 | 146.41 | ± | 51.37 | 58.83 | ± | 10.08 |
ent-16A-13-epi-ST-Δ14-9-PhytoF | 15.75 | ± | 1.21 | 21.30 | ± | 2.10 | 20.83 | ± | 0.90 | 13.70 | ± | 3.21 | 14.77 | ± | 2.42 | 16.24 | ± | 1.21 |
ent-16B-13-epi-ST-Δ14-9-PhytoF | 23.87 | ± | 7.07 | 26.67 | ± | 3.92 | 24.34 | ± | 4.66 | 16.14 | ± | 4.32 | 28.32 | ± | 11.17 | 12.93 | ± | 1.48 |
5(R)-5-F3t-lsoP | 40.49 | ± | 28.74 | 110.61 | ± | 92.55 | 31.46 | ± | 22.71 | 116.24 | ± | 103.04 | 27.35 | ± | 19.60 | 57.62 | ± | 19.22 |
8(R)-8-F3t-lsoP | 10.31 | ± | 3.35 | 16.28 | ± | 0.67 | 12.64 | ± | 2.30 | 10.68 | ± | 2.36 | 16.43 | ± | 10.83 | 6.45 | ± | 1.89 |
18(R)-8-F3t-IsoP | 56.50 | ± | 9.99 | 111.57 | ± | 83.51 | 75.67 | ± | 16.67 | 144.45 | ± | 122.63 | 54.16 | ± | 38.59 | 54.00 | ± | 5.26 |
4(RS)-4-F4t-NeuroP | 15.47 | ± | 1.78 | 37.48 | ± | 13.54 | 25.77 | ± | 0.72 | 14.51 | ± | 2.30 | 15.61 | ± | 3.68 | 20.32 | ± | 3.23 |
10(R)-10-F4t-NeuroP | 27.06 | ± | 18.53 | 12.61 | ± | 3.63 | 15.96 | ± | 3.46 | 18.54 | ± | 4.06 | 20.37 | ± | 9.16 | 14.45 | ± | 0.90 |
10(S)-10-F4t-NeuroP | 23.49 | ± | 6.60 | 16.37 | ± | 6.44 | 19.77 | ± | 2.76 | 20.81 | ± | 5.48 | 18.09 | ± | 6.77 | 11.81 | ± | 1.67 |
13A(RS)-13-F4t-NeuroP | 16.55 | ± | 3.76 | 28.61 | ± | 6.14 | 24.18 | ± | 2.19 | 16.01 | ± | 4.49 | 20.80 | ± | 2.72 | 19.71 | ± | 2.50 |
13B(RS)-13-F4t-NeuroP | 13.57 | ± | 4.57 | 23.01 | ± | 6.00 | 17.27 | ± | 2.32 | 11.80 | ± | 3.52 | 11.60 | ± | 1.90 | 17.22 | ± | 5.37 |
Mi136 | ||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Oxylipins | Control | 1 mM of H2O2 | 5 mM of H2O2 | 4 mM of EtOAc | 10 mΜ of EtOAc | 45 g/L of NaCl | ||||||||||||
Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | |
9-HODE | 9.26 × 102 | ± | 1.54 × 102 | 5.44 × 102 | ± | 1.24 × 102 | 1.17 × 103 | ± | 1.46 × 102 | 1.16 × 103 | ± | 2.54 × 10 | 1.31 × 103 | ± | 2.06 × 102 | 8.48 × 102 | ± | 1.42 × 102 |
13-HODΕ | 1.59 × 103 | ± | 2.89 × 102 | 1.01 × 103 | ± | 1.91 × 102 | 1.96 × 103 | ± | 2.40 × 102 | 2.02 × 103 | ± | 8.21 × 10 | 2.40 × 103 | ± | 2.86 × 102 | 1.35 × 103 | ± | 2.66 × 102 |
5-HΕΤΕ | 2.49 × 102 | ± | 2.71 × 10 | 1.95 × 102 | ± | 7.63 | 3.11 × 102 | ± | 8.77 | 2.53 × 102 | ± | 8.86 | 2.20 × 102 | ± | 4.75 × 10 | 1.96 × 102 | ± | 4.23 × 10 |
8-HΕΤΕ | 1.60 × 102 | ± | 1.23 × 10 | 1.17 × 102 | ± | 1.25 × 10 | 1.93 × 102 | ± | 1.11 × 10 | 1.79 × 102 | ± | 1.45 × 10 | 1.63 × 102 | ± | 3.34 × 10 | 1.31 × 102 | ± | 1.49 × 10 |
12-HΕΤΕ | 2.82 × 102 | ± | 7.18 | 1.82 × 102 | ± | 2.46 × 10 | 2.84 × 102 | ± | 1.47 × 10 | 2.93 × 102 | ± | 2.03 × 10 | 2.77 × 102 | ± | 4.63 × 10 | 1.75 × 102 | ± | 2.93 × 10 |
15-HΕΤΕ | 3.49 × 102 | ± | 3.70 × 10 | 2.85 × 102 | ± | 2.79 × 10 | 3.59 × 102 | ± | 1.42 × 10 | 3.83 × 102 | ± | 1.57 | 3.58 × 102 | ± | 4.86 × 10 | 1.98 × 102 | ± | 1.26 × 10 |
5oxoETE | 1.19 × 102 | ± | 1.98 × 10 | 9.26 × 10 | ± | 5.77 | 8.74 × 10 | ± | 1.53 × 10 | 1.05 × 102 | ± | 1.07 × 10 | 1.07 × 102 | ± | 1.85 × 10 | 8.19 × 10 | ± | 2.23 × 10 |
8.9-EET | 1.35 × 102 | ± | 2.82 × 10 | 1.23 × 102 | ± | 2.32 × 10 | 1.38 × 102 | ± | 2.14 × 10 | 1.47 × 102 | ± | 1.85 | 1.42 × 102 | ± | 1.65 × 10 | 8.80 × 10 | ± | 3.45 × 10 |
11.12-EET | 1.50 × 102 | ± | 2.27 × 10 | 1.23 × 102 | ± | 2.48 × 10 | 1.30 × 102 | ± | 2.79 × 10 | 1.46 × 102 | ± | 1.74 × 10 | 1.13 × 102 | ± | 7.94 | 7.00 × 10 | ± | 1.94 × 10 |
14.15-ΕΕΤ | 1.43 × 102 | ± | 3.70 × 10 | 1.24 × 102 | ± | 3.57 × 10 | 1.10 × 102 | ± | 3.85 × 10 | 1.59 × 102 | ± | 9.89 | 1.16 × 102 | ± | 2.00 × 10 | 6.08 × 10 | ± | 2.25 × 10 |
PGE2 | 1.80 × 102 | ± | 2.70 × 102 | 3.64 × 102 | ± | 4.82 × 102 | 9.01 × 10 | ± | 8.28 × 10 | 1.04 × 103 | ± | 1.05 × 103 | 6.87 × 102 | ± | 8.42 × 102 | 3.42 × 102 | ± | 2.19 × 102 |
PGE3 | 1.51 × 103 | ± | 1.54 × 103 | 7.43 × 103 | ± | 4.02 × 103 | 2.23 × 103 | ± | 2.07 × 103 | 2.04 × 104 | ± | 8.99 × 103 | 1.81 × 104 | ± | 1.64 × 104 | 4.22 × 103 | ± | 5.71 × 103 |
15-d-PGJ2 | 3.59 × 10 | ± | 6.16 × 10 | 2.97 × 102 | ± | 1.69 × 103 | 6.66 × 10 | ± | 1.50 × 10 | 5.81 × 102 | ± | 1.08 × 103 | 2.19 × 102 | ± | 3.44 × 10 | 4.21 × 10 | ± | 1.12 × 102 |
18-HEPE | 4.73 × 104 | ± | 1.05 × 105 | 2.36 × 105 | ± | 1.27 × 106 | 6.69 × 104 | ± | 1.78 × 104 | 6.82 × 105 | ± | 1.09 × 106 | 2.62 × 105 | ± | 2.47 × 104 | 1.26 × 105 | ± | 1.17 × 105 |
14-HDoHE | 3.73 × 102 | ± | 7.66 × 10 | 2.25 × 102 | ± | 5.08 × 10 | 3.61 × 102 | ± | 4.39 × 10 | 4.20 × 102 | ± | 2.67 × 10 | 4.66 × 102 | ± | 8.73 × 10 | 3.85 × 102 | ± | 5.08 × 10 |
17-HDoHE | 4.83 × 102 | ± | 9.38 × 10 | 2.90 × 102 | ± | 8.94 × 10 | 4.40 × 102 | ± | 4.88 × 10 | 4.64 × 102 | ± | 5.74 × 10 | 5.56 × 102 | ± | 1.13 × 102 | 4.38 × 102 | ± | 7.32 × 10 |
5(RS)-5-F2t-lsoP | 167.17 | ± | 89.06 | 115.41 | ± | 40.19 | 109.59 | ± | 10.60 | 97.28 | ± | 20.92 | 116.45 | ± | 49.26 | 55.15 | ± | 8.06 |
15-A2-IsoP | 130.51 | ± | 46.56 | 101.89 | ± | 21.26 | 94.74 | ± | 7.68 | 105.64 | ± | 19.85 | 138.11 | ± | 55.59 | 34.07 | ± | 7.63 |
9-L1t-PhytoP | 6.55 | ± | 4.64 | 3.50 | ± | 0.94 | 3.05 | ± | 1.10 | 2.98 | ± | 0.73 | 4.64 | ± | 1.12 | 9.00 | ± | 10.73 |
9-F1t-PhytoP | 8.97 | ± | 12.69 | 3.19 | ± | 4.51 | 2.23 | ± | 3.15 | 0.00 | ± | 0.00 | 0.00 | ± | 0.00 | 4.69 | ± | 6.63 |
16-B1t-PhytoP | 8.43 | ± | 7.14 | 4.35 | ± | 1.43 | 3.57 | ± | 1.35 | 3.54 | ± | 0.66 | 4.70 | ± | 1.23 | 11.24 | ± | 13.06 |
16-epi-16-F1t-PhytoP | 57.05 | ± | 3.84 | 49.25 | ± | 8.16 | 56.88 | ± | 9.46 | 45.42 | ± | 11.67 | 50.85 | ± | 3.25 | 52.50 | ± | 6.67 |
16-F1t-PhytoP | 68.99 | ± | 5.64 | 62.36 | ± | 11.22 | 71.36 | ± | 12.47 | 62.42 | ± | 11.31 | 64.17 | ± | 6.92 | 68.13 | ± | 6.81 |
ent-9A-12-epi-ST-Δ10-13-PhytoF | 5.75 | ± | 2.69 | 5.80 | ± | 2.06 | 3.64 | ± | 0.35 | 3.96 | ± | 0.82 | 4.60 | ± | 1.13 | 4.07 | ± | 2.64 |
ent-16A-9-epi-ST-Δ14-10-PhytoF | 6.95 | ± | 0.75 | 5.83 | ± | 1.47 | 6.60 | ± | 0.59 | 6.81 | ± | 1.53 | 8.42 | ± | 1.76 | 5.48 | ± | 3.50 |
ent-16B-9-epi-ST-Δ14-10-PhytoF | 10.05 | ± | 1.16 | 8.70 | ± | 1.88 | 9.34 | ± | 1.25 | 8.46 | ± | 1.81 | 11.17 | ± | 2.40 | 6.88 | ± | 6.56 |
ent-16A-13-epi-ST-Δ14-9-PhytoF | 9.09 | ± | 11.95 | 4.95 | ± | 5.86 | 1.03 | ± | 0.27 | 0.68 | ± | 0.11 | 0.83 | ± | 0.16 | 1.50 | ± | 1.15 |
ent-16B-13-epi-ST-Δ14-9-PhytoF | 5.49 | ± | 4.58 | 4.55 | ± | 4.42 | 1.73 | ± | 0.48 | 2.04 | ± | 0.60 | 3.16 | ± | 1.35 | 1.41 | ± | 1.02 |
5(R)-5-F3t-lsoP | 165.29 | ± | 27.74 | 112.96 | ± | 7.80 | 139.18 | ± | 16.00 | 112.42 | ± | 11.47 | 142.33 | ± | 26.24 | 242.00 | ± | 54.01 |
5(S)-5-F3t-lsoP | 76.83 | ± | 23.15 | 43.78 | ± | 3.55 | 53.92 | ± | 10.80 | 45.54 | ± | 10.36 | 50.77 | ± | 11.22 | 88.03 | ± | 24.68 |
8(R)-8-F3t-lsoP | 16.41 | ± | 6.10 | 21.36 | ± | 3.24 | 15.82 | ± | 2.62 | 20.11 | ± | 2.20 | 14.45 | ± | 2.47 | 17.88 | ± | 2.20 |
18(R)-8-F3t-IsoP | 163.16 | ± | 172.45 | 77.53 | ± | 55.02 | 42.79 | ± | 8.53 | 39.20 | ± | 10.63 | 44.79 | ± | 17.65 | 52.50 | ± | 11.36 |
18(S)-8-F3t-IsoP | 7.84 | ± | 6.18 | 10.72 | ± | 1.73 | 10.93 | ± | 2.26 | 13.68 | ± | 0.69 | 16.72 | ± | 2.68 | 29.24 | ± | 8.78 |
Mi168 | |||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Oxylipins | Control | 0.25 mM of H2O2 | 1 mM of H2O2 | 2 mM of EtOAc | 10 mΜ of EtOAc | 29 g/L of NaCl | 45 g/L of NaCl | ||||||||||||||
Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | Concentration (pg/mg) | ± | SD | |
9-HODE | 3.70 × 102 | ± | 3.27 × 10 | 4.39 × 102 | ± | 1.72 × 102 | 2.49 × 102 | ± | 6.53 × 10 | 2.62 × 102 | ± | 4.07 × 10 | 4.22 × 102 | ± | 6.45 × 10 | 3.47 × 102 | ± | 7.87 × 10 | 2.70 × 102 | ± | 3.28 |
13-HODΕ | 4.65 × 102 | ± | 4.61 × 10 | 5.21 × 102 | ± | 1.91 × 102 | 3.22 × 102 | ± | 9.20 × 10 | 3.31 × 102 | ± | 6.70 × 10 | 5.20 × 102 | ± | 7.22 × 10 | 4.12 × 102 | ± | 7.05 × 10 | 3.58 × 102 | ± | 2.02 × 10 |
5-HΕΤΕ | 3.66 × 103 | ± | 6.23 × 10 | 4.28 × 103 | ± | 1.70 × 103 | 2.57 × 103 | ± | 5.18 × 102 | 3.76 × 103 | ± | 3.71 × 102 | 5.94 × 103 | ± | 2.41 × 103 | 2.75 × 103 | ± | 5.15 × 102 | 1.80 × 103 | ± | 1.67 × 102 |
8-HΕΤΕ | 2.23 × 103 | ± | 1.10 × 102 | 2.73 × 103 | ± | 1.02 × 103 | 1.57 × 103 | ± | 4.92 × 102 | 2.19 × 103 | ± | 1.44 × 102 | 3.26 × 103 | ± | 1.34 × 103 | 1.67 × 103 | ± | 2.91 × 102 | 8.63 × 102 | ± | 8.31 × 10 |
12-HΕΤΕ | 3.07 × 103 | ± | 2.18 × 102 | 3.67 × 103 | ± | 1.38 × 103 | 2.18 × 103 | ± | 7.48 × 102 | 2.80 × 103 | ± | 1.95 × 102 | 4.42 × 103 | ± | 1.90 × 103 | 2.27 × 103 | ± | 3.95 × 102 | 1.29 × 103 | ± | 7.59 × 10 |
15-HΕΤΕ | 4.22 × 103 | ± | 2.09 × 102 | 5.06 × 103 | ± | 1.91 × 103 | 2.95 × 103 | ± | 1.10 × 103 | 3.88 × 103 | ± | 5.55 × 102 | 6.04 × 103 | ± | 1.88 × 103 | 3.33 × 103 | ± | 5.33 × 102 | 2.48 × 103 | ± | 2.33 × 102 |
5oxoETE | 9.41 × 102 | ± | 6.88 × 10 | 1.19 × 103 | ± | 4.76 × 102 | 6.73 × 102 | ± | 1.82 × 102 | 9.59 × 102 | ± | 7.00 × 10 | 1.64 × 103 | ± | 6.79 × 102 | 7.73 × 102 | ± | 1.20 × 102 | 5.77 × 102 | ± | 7.91 |
8.9-EET | 5.79 × 102 | ± | 3.04 × 10 | 6.05 × 102 | ± | 2.40 × 102 | 3.92 × 102 | ± | 2.96 × 10 | 7.82 × 102 | ± | 2.11 × 102 | 1.22 × 103 | ± | 5.95 × 102 | 4.40 × 102 | ± | 5.47 × 10 | 3.12 × 102 | ± | 2.64 × 10 |
11.12-EET | 4.37 × 102 | ± | 3.33 × 10 | 4.52 × 102 | ± | 1.36 × 102 | 3.29 × 102 | ± | 4.50 × 10 | 6.02 × 102 | ± | 1.75 × 102 | 9.73 × 102 | ± | 5.31 × 102 | 3.52 × 102 | ± | 5.29 × 10 | 2.47 × 102 | ± | 2.58 × 10 |
14.15-ΕΕΤ | 4.61 × 102 | ± | 5.58 × 10 | 4.98 × 1022 | ± | 1.75 × 102 | 3.24 × 102 | ± | 4.31 × 10 | 6.45 × 102 | ± | 1.52 × 102 | 9.77 × 102 | ± | 5.55 × 102 | 3.57 × 102 | ± | 5.98 × 10 | 2.11 × 102 | ± | 1.29 × 10 |
TXB2 | 3.86 × 10 | ± | 1.14 × 10 | 4.47 × 10 | ± | 3.08 × 10 | 2.65 × 10 | ± | 6.16 | 2.92 × 10 | ± | 8.55 | 7.86 × 10 | ± | 2.82 × 10 | 2.88 × 10 | ± | 4.45 | 1.31 × 10 | ± | 4.00 × 10−1 |
PGD2 | 1.87 × 10 | ± | 6.70 | 3.26 × 10 | ± | 1.46 × 10 | 2.16 × 10 | ± | 6.85 | 2.59 × 10 | ± | 1.47 | 7.95 × 10 | ± | 5.34 × 10 | 1.84 × 10 | ± | 4.27 | 2.08 × 10 | ± | 4.49 |
PGE2 | 1.57 × 102 | ± | 1.07 × 102 | 8.41 × 10 | ± | 6.39 × 10 | 1.05 × 102 | ± | 9.99 × 10 | 1.25 × 102 | ± | 7.83 × 10 | 1.17 × 102 | ± | 8.36 × 10 | 1.78 × 102 | ± | 1.24 × 102 | 4.81 × 10 | ± | 2.48 × 10 |
PGE3 | 6.59 × 102 | ± | 1.84 × 102 | 8.48 × 102 | ± | 6.07 × 102 | 3.80 × 102 | ± | 5.86 × 10 | 5.75 × 102 | ± | 1.24 × 102 | 1.15 × 103 | ± | 5.73 × 102 | 3.50 × 102 | ± | 5.02 × 10 | 2.10 × 102 | ± | 7.89 |
15-d-PGJ2 | 1.27 × 10 | ± | 3.49 × 10−1 | 1.51 × 10 | ± | 1.53 × 10 | 9.64 | ± | 1.82 | 1.93 × 10 | ± | 7.63 | 4.16 × 10 | ± | 2.05 × 10 | 1.13 × 10 | ± | 2.83 | 3.28 | ± | 1.36 |
18-HEPE | 4.71 × 104 | ± | 3.23 × 103 | 5.87 × 104 | ± | 2.64 × 104 | 3.41 × 104 | ± | 8.83 × 103 | 4.24 × 104 | ± | 4.61 × 103 | 7.26 × 104 | ± | 2.00 × 104 | 4.70 × 104 | ± | 7.55 × 103 | 3.37 × 104 | ± | 3.39 × 103 |
RvD5 | 1.15 × 10 | ± | 2.58 | 1.32 × 10 | ± | 5.78 | 1.30 × 10 | ± | 5.23 | 8.23 | ± | 1.19 | 1.37 × 10 | ± | 1.23 × 10 | 1.04 × 10 | ± | 5.50 | 4.23 | ± | 7.07 × 10−2 |
PDX | 1.24 × 10 | ± | 2.80 | 1.75 × 10 | ± | 6.97 | 1.26 × 10 | ± | 5.36 | 1.30 × 10 | ± | 2.49 | 1.81 × 10 | ± | 9.13 | 1.46 × 10 | ± | 2.60 | 1.05 × 10 | ± | 3.18 |
14-HDoHE | 1.02 × 104 | ± | 1.15 × 103 | 1.39 × 104 | ± | 5.14 × 103 | 8.90 × 103 | ± | 2.15 × 103 | 1.13 × 104 | ± | 1.19 × 103 | 1.60 × 104 | ± | 6.11 × 103 | 9.80 × 103 | ± | 2.28 × 103 | 5.52 × 103 | ± | 8.59 × 102 |
17-HDoHE | 3.21 × 104 | ± | 4.23 × 103 | 4.09 × 104 | ± | 1.37 × 104 | 2.59 × 104 | ± | 1.09 × 104 | 3.23 × 104 | ± | 4.76 × 103 | 5.07 × 104 | ± | 1.20 × 104 | 3.08 × 104 | ± | 5.16 × 103 | 2.24 × 104 | ± | 3.87 × 103 |
5(RS)-5-F2c-lsoP | 111.13 | ± | 3.01 | 115.61 | ± | 4.08 | 90.74 | ± | 20.99 | 90.61 | ± | 2.74 | 129.47 | ± | 15.19 | 100.71 | ± | 33.99 | 133.33 | ± | 21.74 |
5(RS)-5-F2t-lsoP | 14.10 | ± | 0.83 | 16.19 | ± | 0.94 | 12.01 | ± | 1.28 | 13.60 | ± | 2.74 | 17.55 | ± | 5.87 | 13.26 | ± | 2.56 | 21.60 | ± | 3.92 |
15-A2-IsoP | 57.46 | ± | 13.60 | 65.81 | ± | 14.22 | 49.11 | ± | 16.03 | 43.12 | ± | 0.59 | 68.26 | ± | 11.57 | 58.43 | ± | 18.03 | 56.91 | ± | 13.79 |
15-epi-15-F2t-IsoP | 6.70 | ± | 1.37 | 9.11 | ± | 1.65 | 6.63 | ± | 0.74 | 6.74 | ± | 1.88 | 9.29 | ± | 1.08 | 7.97 | ± | 1.82 | 10.89 | ± | 1.69 |
15(RS)-15-F2t-lsoP | 3.33 | ± | 0.26 | 4.42 | ± | 1.79 | 3.64 | ± | 0.42 | 3.38 | ± | 0.56 | 5.07 | ± | 1.87 | 3.32 | ± | 0.41 | 5.13 | ± | 0.55 |
4(RS)-14-F3t-NeuroP | 18.59 | ± | 2.37 | 23.44 | ± | 4.62 | 19.18 | ± | 3.00 | 17.33 | ± | 1.10 | 22.13 | ± | 5.16 | 19.76 | ± | 4.11 | 33.50 | ± | 4.55 |
9-L1t-PhytoP | 3.09 | ± | 0.74 | 6.22 | ± | 3.77 | 1.22 | ± | 0.25 | 4.29 | ± | 2.57 | 2.95 | ± | 0.87 | 2.24 | ± | 0.56 | 3.56 | ± | 0.99 |
16-B1t-PhytoP | 3.71 | ± | 0.55 | 6.98 | ± | 4.56 | 1.34 | ± | 0.33 | 4.51 | ± | 2.98 | 3.82 | ± | 1.04 | 2.99 | ± | 0.20 | 4.69 | ± | 1.08 |
16-epi-16-F1t-PhytoP | 71.71 | ± | 11.99 | 113.39 | ± | 55.66 | 83.34 | ± | 39.74 | 84.27 | ± | 17.68 | 103.26 | ± | 27.17 | 82.56 | ± | 26.79 | 77.59 | ± | 13.51 |
16-F1t-PhytoP | 196.36 | ± | 23.86 | 267.43 | ± | 75.80 | 203.33 | ± | 81.34 | 213.81 | ± | 28.03 | 297.12 | ± | 77.60 | 205.93 | ± | 60.06 | 161.55 | ± | 41.06 |
ent-16A-9-epi-ST-Δ14-10-PhytoF | 1.60 | ± | 0.37 | 3.17 | ± | 1.55 | 1.02 | ± | 0.18 | 1.52 | ± | 1.08 | 2.09 | ± | 0.39 | 1.49 | ± | 0.18 | 2.00 | ± | 0.05 |
ent-16B-9-epi-ST-Δ14-10-PhytoF | 2.15 | ± | 0.62 | 4.60 | ± | 2.79 | 1.38 | ± | 0.28 | 2.47 | ± | 0.68 | 2.20 | ± | 0.39 | 1.70 | ± | 0.47 | 3.19 | ± | 0.76 |
ent-16A-13-epi-ST-Δ14-9-PhytoF | 1.77 | ± | 1.16 | 2.24 | ± | 2.14 | 0.67 | ± | 0.15 | 0.57 | ± | 0.41 | 1.22 | ± | 0.56 | 0.98 | ± | 0.11 | 1.02 | ± | 0.73 |
5(R)-5-F3t-lsoP | 247.40 | ± | 45.11 | 283.17 | ± | 43.02 | 209.98 | ± | 31.07 | 204.07 | ± | 37.03 | 319.24 | ± | 64.80 | 279.09 | ± | 64.13 | 495.36 | ± | 9.54 |
5(S)-5-F3t-lsoP | 87.74 | ± | 12.50 | 96.90 | ± | 21.94 | 74.47 | ± | 6.85 | 76.78 | ± | 18.69 | 109.24 | ± | 31.62 | 99.86 | ± | 26.60 | 171.49 | ± | 5.36 |
8(R)-8-F3t-lsoP | 13.05 | ± | 3.25 | 18.33 | ± | 5.29 | 12.24 | ± | 2.03 | 13.59 | ± | 1.22 | 25.82 | ± | 6.01 | 15.82 | ± | 2.63 | 25.63 | ± | 4.18 |
8(S)-8-F3t-lsoP | 12.07 | ± | 3.39 | 11.00 | ± | 3.69 | 8.44 | ± | 1.99 | 8.65 | ± | 2.56 | 12.66 | ± | 2.99 | 10.87 | ± | 2.76 | 11.96 | ± | 2.89 |
18(R)-8-F3t-IsoP | 392.01 | ± | 375.37 | 659.01 | ± | 738.83 | 83.54 | ± | 19.69 | 89.87 | ± | 42.52 | 167.32 | ± | 43.50 | 159.82 | ± | 34.50 | 199.22 | ± | 27.56 |
18(S)-8-F3t-IsoP | 23.03 | ± | 5.23 | 27.85 | ± | 1.37 | 20.46 | ± | 3.16 | 20.45 | ± | 10.01 | 27.20 | ± | 6.80 | 28.07 | ± | 4.57 | 51.69 | ± | 5.57 |
4(RS)-4-F4t-NeuroP | 8.23 | ± | 0.49 | 10.72 | ± | 2.18 | 8.12 | ± | 1.46 | 7.84 | ± | 0.24 | 10.36 | ± | 2.27 | 8.44 | ± | 2.00 | 13.65 | ± | 1.38 |
10(R)-10-F4t-NeuroP | 3.98 | ± | 0.46 | 4.39 | ± | 0.88 | 3.05 | ± | 0.82 | 4.26 | ± | 0.97 | 5.40 | ± | 2.59 | 4.03 | ± | 0.90 | 6.16 | ± | 0.47 |
10(S)-10-F4t-NeuroP | 3.17 | ± | 0.59 | 4.22 | ± | 2.26 | 3.52 | ± | 0.84 | 2.87 | ± | 0.29 | 4.57 | ± | 1.39 | 4.71 | ± | 0.86 | 5.06 | ± | 0.32 |
13A(RS)-13-F4t-NeuroP | 5.22 | ± | 0.95 | 5.81 | ± | 1.54 | 4.53 | ± | 0.66 | 5.19 | ± | 0.88 | 6.34 | ± | 1.87 | 6.36 | ± | 1.75 | 8.39 | ± | 0.91 |
13B(RS)-13-F4t-NeuroP | 4.28 | ± | 0.61 | 5.92 | ± | 0.34 | 4.39 | ± | 0.58 | 2.68 | ± | 1.99 | 3.82 | ± | 0.36 | 3.95 | ± | 0.63 | 5.46 | ± | 1.94 |
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Linares-Maurizi, A.; Awad, R.; Durbec, A.; Reversat, G.; Gros, V.; Galano, J.-M.; Bertrand-Michel, J.; Durand, T.; Pradelles, R.; Oger, C.; et al. Stress-Induced Production of Bioactive Oxylipins in Marine Microalgae. Mar. Drugs 2024, 22, 406. https://doi.org/10.3390/md22090406
Linares-Maurizi A, Awad R, Durbec A, Reversat G, Gros V, Galano J-M, Bertrand-Michel J, Durand T, Pradelles R, Oger C, et al. Stress-Induced Production of Bioactive Oxylipins in Marine Microalgae. Marine Drugs. 2024; 22(9):406. https://doi.org/10.3390/md22090406
Chicago/Turabian StyleLinares-Maurizi, Amandyne, Rana Awad, Anaelle Durbec, Guillaume Reversat, Valérie Gros, Jean-Marie Galano, Justine Bertrand-Michel, Thierry Durand, Rémi Pradelles, Camille Oger, and et al. 2024. "Stress-Induced Production of Bioactive Oxylipins in Marine Microalgae" Marine Drugs 22, no. 9: 406. https://doi.org/10.3390/md22090406