Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida
Abstract
:1. Introduction
2. Results and Discussion
2.1. GC Elution Profiles
2.2. Structural Elucidation of cis-11,12-Methylene-Hexadecanoic Acid (Peak 5)
2.3. Structural Elucidation of 11-Cyclopentylundecanoic Acid (Peak 6), 13-Cyclopentyltridecanoic Acid (Peak 12), and cis-11-Hexadecenoic Acid (Peak 4)
2.4. Fatty Acid Composition
3. Materials and Methods
3.1. Samples, Lipid Extraction, and Analysis of Fatty Acids
3.2. Silver Ion-TLC (Ag+-TLC)
3.3. Hydrogenation
3.4. Preparation of Picolinyl Ester Derivatives
3.5. Preparation of 4,4-Dimethyloxazoline Derivatives
3.6. H-NMR
3.7. FT-IR
3.8. GC-MS
3.9. Mass Spectrum Data of Picolinyl Ester Derivatives
3.9.1. cis-11,12-Methylene-Hexadecanoic Acid Picolinyl Ester
3.9.2. 11-Cyclopenylundecanoic Acid Picolinyl Ester
3.9.3. 13-Cyclopenyltridecanoic Acid Picolinyl Ester
3.9.4. cis-11-Hexadecenoic Acid Picolinyl Ester
3.10. Mass Spectrum Data of DMOX Derivatives
3.10.1. cis-11,12-Methylene-Hexadecanoic Acid DMOX
3.10.2. 11-Cyclopenylundecanoic Acid DMOX
3.10.3. 13-Cyclopenyltridecanoic Acid DMOX
3.11. NMR Spectrum Data of Saturated FAME Fraction
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Fatty Acid | ECL a | wt % |
---|---|---|
12:0 | 12.00 | 0.05 ± 0.0 |
14:0 | 14.00 | 1.18 ± 0.2 |
Iso 15:0 | 14.60 | 0.27 ± 0.0 |
15:0 | 15.00 | 0.29 ± 0.0 |
Iso 16:0 | 15.37 | 0.17 ± 0.0 |
Anteiso 16:0 | 15.67 | 0.36 ± 0.0 |
16:0 | 16.00 | 28.36 ± 1.4 |
Iso 17:0 | 16.53 | 0.19 ± 0.0 |
17:0 | 17.00 | 0.54 ± 0.1 |
cy17:0 b | 17.39 | 7.89 ± 0.8 |
cy16:0 c | 17.44 | 7.04 ± 0.7 |
18:0 | 18.00 | 0.56 ± 0.1 |
cy18:0 d | 19.45 | 4.85 ± 0.5 |
ΣSaturates | 51.75 ± 1.6 | |
14:1n-5 | 14.27 | 0.24 ± 0.0 |
16:1n-9 | 16.20 | 0.23 ± 0.0 |
16:1n-7 | 16.26 | 1.02 ± 0.1 |
16:1n-5 | 16.40 | 8.96 ± 0.7 |
18:1n-9 | 18.28 | 0.80 ± 0.1 |
18:1n-7 | 18.35 | 0.39 ± 0.0 |
18:1n-5 | 18.49 | 1.64 ± 0.3 |
20:1n-9 | 20.26 | 0.11 ± 0.0 |
20:1n-7 | 20.32 | 0.20 ± 0.0 |
ΣMonoenes | 13.59 ± 0.9 | |
16:2n-6 | 16.65 | 0.14 ± 0.0 |
16:3n-3 | 17.30 | 0.03 ± 0.0 |
16:4n-3 | 17.74 | 0.04 ± 0.0 |
18:2n-6 | 18.77 | 0.27 ± 0.0 |
18:3n-6 | 19.02 | 0.20 ± 0.0 |
20:3n-6 | 20.91 | 0.39 ± 0.0 |
20:4n-6 | 21.12 | 23.69 ± 1.3 |
20:4n-3 | 21.29 | 0.05 ± 0.0 |
20:5n-3 | 21.68 | 9.14 ± 0.9 |
ΣPolyenes | 33.95 ± 1.3 | |
Others | 0.71 ± 0.2 |
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Kim, G.-W.; Sim, J.-M.; Itabashi, Y.; Jung, M.-J.; Jun, J.-Y. Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida. Molecules 2021, 26, 2286. https://doi.org/10.3390/molecules26082286
Kim G-W, Sim J-M, Itabashi Y, Jung M-J, Jun J-Y. Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida. Molecules. 2021; 26(8):2286. https://doi.org/10.3390/molecules26082286
Chicago/Turabian StyleKim, Gwang-Woo, Jae-Man Sim, Yutaka Itabashi, Min-Jeong Jung, and Joon-Young Jun. 2021. "Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida" Molecules 26, no. 8: 2286. https://doi.org/10.3390/molecules26082286