Seasonal Changes in Essential Oil Constituents of Cystoseira compressa: First Report
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Algal Material
3.2. Extraction of Essential Oils
3.3. GC–MS Analysis of Volatiles
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
- El Hattab, M. Algae Essential Oils: Chemistry, Ecology, and Biological Activities. In Essential Oils—Bioactive Compounds, New Perspectives and Applications; IntechOpen Limited: London, UK, 2020; pp. 1–25. [Google Scholar] [CrossRef]
- Garicano Vilar, E.; O’Sullivan, M.G.; Kerry, J.P.; Kilcawley, K.N. Volatile Compounds of Six Species of Edible Seaweed: A Review. Algal Res. 2020, 45, 101740. [Google Scholar] [CrossRef]
- Vizetto-Duarte, C.; Pereira, H.; De Sousa, C.B.; Rauter, A.P.; Albericio, F.; Custódio, L.; Barreira, L.; Varela, J. Fatty Acid Profile of Different Species of Algae of the Cystoseira Genus: A Nutraceutical Perspective. Nat. Prod. Res. 2015, 29, 1264–1270. [Google Scholar] [CrossRef]
- Oucif, H.; Benaissa, M.; Ali Mehidi, S.; Prego, R.; Aubourg, S.P.; Abi-Ayad, S.M.E.A. Chemical Composition and Nutritional Value of Different Seaweeds from the West Algerian Coast. J. Aquat. Food Prod. Technol. 2020, 29, 90–104. [Google Scholar] [CrossRef]
- Maggio, A.; Alduina, R.; Oddo, E.; Piccionello, A.P.; Mannino, A.M. Antibacterial Activity and HPLC Analysis of Extracts from Mediterranean Brown Algae. Plant Biosyst. 2020, 1–17. [Google Scholar] [CrossRef]
- Generalić Mekinić, I.; Skroza, D.; Šimat, V.; Hamed, I.; Čagalj, M.; Perković, Z.P. Phenolic Content of Brown Algae (Pheophyceae) Species: Extraction, Identification, and Quantification. Biomolecules. 2019, 9, 244. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Mekinić, I.G.; Šimat, V.; Botić, V.; Crnjac, A.; Smoljo, M.; Soldo, B.; Ljubenkov, I.; Čagalj, M.; Skroza, D. Bioactive Phenolic Metabolites from Adriatic Brown Algae Dictyota Dichotoma and Padina Pavonica (Dictyotaceae). Foods 2021, 10, 1187. [Google Scholar] [CrossRef] [PubMed]
- Cvitković, D.; Dragović-Uzelac, V.; Dobrinčić, A.; Čož-Rakovac, R.; Balbino, S. The Effect of Solvent and Extraction Method on the Recovery of Lipid Fraction from Adriatic Sea Macroalgae. Algal Res. 2021, 56, 102291. [Google Scholar] [CrossRef]
- Čagalj, M.; Skroza, D.; Tabanelli, G.; Özogul, F.; Šimat, V. Maximizing the Antioxidant Capacity of Padina Pavonica by Choosing the Right Drying and Extraction Methods. Processes 2021, 9, 587. [Google Scholar] [CrossRef]
- Akakabe, Y.; Kajiwara, T. Bioactive Volatile Compounds from Marine Algae: Feeding Attractants. J. Appl. Phycol. 2008, 20, 661–664. [Google Scholar] [CrossRef]
- Gressler, V.; Colepicolo, P.; Pinto, E. Useful Strategies for Algal Volatile Analysis. Curr. Anal. Chem. 2010, 5, 271–292. [Google Scholar] [CrossRef]
- Zuo, Z. Why Algae Release Volatile Organic Compounds—The Emission and Roles. Front. Microbiol. 2019, 10, 491. [Google Scholar] [CrossRef] [Green Version]
- Bouzidi, N.; Seridi, H.; Daghbouche, Y.; Piovetti, L.; El Hattab, M. Comparison of the Chemical Composition of “Cystoseira Sedoides (Desfontaines) C. Agardh” Volatile Compounds Obtained by Different Extraction Techniques. Rec. Nat. Prod. 2015, 10, 58–67. [Google Scholar]
- Bruno de Sousa, C.; Gangadhar, K.N.; Macridachis, J.; Pavão, M.; Morais, T.R.; Campino, L.; Varela, J.; Lago, J.H.G. Cystoseira Algae (Fucaceae): Update on Their Chemical Entities and Biological Activities. Tetrahedron Asymmetry 2017, 28, 1486–1505. [Google Scholar] [CrossRef]
- Falace, A.; Zanelli, E.; Bressan, G. Morphological and Reproductive Phenology of Cystoseira Compressa (Esper) Gerloff & Nizamuddin (Fucales, Fucophyceae) in the Gulf of Trieste (North Adriatic). Ann. Ser. Hist. Nat. 2005, 5, 5–12. [Google Scholar]
- Hentati, F.; Delattre, C.; Ursu, A.V.; Desbrières, J.; Le Cerf, D.; Gardarin, C.; Abdelkafi, S.; Michaud, P.; Pierre, G. Structural Characterization and Antioxidant Activity of Water-Soluble Polysaccharides from the Tunisian Brown Seaweed Cystoseira Compressa. Carbohydr. Polym. 2018, 198, 589–600. [Google Scholar] [CrossRef]
- Gheda, S.; Naby, M.A.; Mohamed, T.; Pereira, L.; Khamis, A. Antidiabetic and Antioxidant Activity of Phlorotannins Extracted from the Brown Seaweed Cystoseira Compressa in Streptozotocin-Induced Diabetic Rats. Environ. Sci. Pollut. Res. 2021, 28, 22886–22901. [Google Scholar] [CrossRef]
- Mancuso, F.P.; Messina, C.M.; Santulli, A.; Laudicella, V.A.; Giommi, C.; Sarà, G.; Airoldi, L. Influence of Ambient Temperature on the Photosynthetic Activity and Phenolic Content of the Intertidal Cystoseira Compressa along the Italian Coastline. J. Appl. Phycol. 2019, 31, 3069–3076. [Google Scholar] [CrossRef]
- Milkova, T.; Talev, G.; Christov, R.; Dimitrova-Konaklieva, S.; Popov, S. Sterols and Volatiles in Cystoseira Barbata and Cystoseira Crinita from the Black Sea. Phytochemistry 1997, 45, 93–95. [Google Scholar] [CrossRef]
- Ozdemir, G.; Horzum, Z.; Sukatar, A.; Karabay-Yavasoglu, N. Antimicrobial Activities of Volatile Components and Various Extracts of Dictyopteris Membranaceae and Cystoseira Barbata from the Coast of Izmir, Turkey. Pharm. Biol. 2006, 44, 183–188. [Google Scholar] [CrossRef] [Green Version]
- Amrani Zerrifi, S.E.; El Khalloufi, F.; Mugani, R.; El Mahdi, R.; Kasrati, A.; Soulaimani, B.; Barros, L.; Ferreira, I.C.F.R.; Amaral, J.S.; Finimundy, T.C.; et al. Seaweed Essential Oils as a New Source of Bioactive Compounds for Cyanobacteria Growth Control: Innovative Ecological Biocontrol Approach. Toxins 2020, 12, 527. [Google Scholar] [CrossRef]
- Kord, A.; Cherif, Y.F.; Amiali, M.; Mustapha, M.A.; Benfares, R.; Soumia, B.; Belfadel, O. Fatty Acids Composition of Cystoseira Sauvageauana and Laurencia Pinnatifida Collected from the Algerian Coast. Acta Period. Technol. 2019, 50, 113–122. [Google Scholar] [CrossRef] [Green Version]
- FAO. 2,6,10-Trimethyl-2,6,10-pentadecatrien-14-one. Available online: http://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/1055/ (accessed on 27 September 2021).
- Abu-Khudir, R.; Ismail, G.A.; Diab, T. Antimicrobial, Antioxidant, and Anti-Tumor Activities of Sargassum Linearifolium and Cystoseira Crinita from Egyptian Mediterranean Coast. Nutr. Cancer 2021, 73, 829–844. [Google Scholar] [CrossRef]
- Ahmed, S.A.; Rahman, A.A.; Elsayed, K.N.M.; Abd El-Mageed, H.R.; Mohamed, H.S.; Ahmed, S.A. Cytotoxic Activity, Molecular Docking, Pharmacokinetic Properties and Quantum Mechanics Calculations of the Brown Macroalga Cystoseira Trinodis Compounds. J. Biomol. Struct. Dyn. 2021, 39, 3855–3873. [Google Scholar] [CrossRef]
- Mastelić, J.; Jerković, I.; Blažević, I.; Radonić, A.; Krstulović, L. Hydrodistillation-Adsorption Method for the Isolation of Water-Soluble, Non-Soluble and High Volatile Compounds from Plant Materials. Talanta 2008, 76, 885–891. [Google Scholar] [CrossRef]
- Blažević, I.; Đulović, A.; Čikeš Čulić, V.; Burčul, F.; Ljubenkov, I.; Ruščić, M.; Generalić Mekinić, I. Bunias Erucago L.: Glucosinolate Profile and in Vitro Biological Potential. Molecules 2019, 24, 741. [Google Scholar] [CrossRef] [Green Version]
Compound | C. compressa Samples | |||||||||
---|---|---|---|---|---|---|---|---|---|---|
No. | Rt (min) | Name | Similarity (%) | MW | Formula | CAS | May | June | July | August |
1 | 7.10 | Pent-1-en-3-one | 95 | 84.12 | C5H8O | 1629-58-9 | 0.07 | n.d. | n.d. | n.d. |
2 | 7.55 | Tetrahydro-2,5-dimethyl-furan | 97 | 100.15 | C6H12O | 1003-38-9 | 0.88 | 0.06 | 0.35 | 0.16 |
3 | 10.24 | Tetrahydro-2-furanmethanol | 92 | 102.13 | C5H10O2 | 97-99-4 | 0.06 | n.d. | 0.02 | 0.01 |
4 | 10.85 | Hex-5-enal | 93 | 98.14 | C6H10O | 764-59-0 | n.d. | 0.01 | 0.01 | 0.01 |
5 | 11.07 | Hexan-2-one | 93 | 100.16 | C6H12O | 591-78-6 | 0.05 | n.d. | 0.03 | 0.01 |
6 | 11.33 | Hexan-3-ol | 90 | 102.17 | C6H14O | 623-37-0 | 0.07 | n.d. | 0.03 | 0.03 |
7 | 11.48 | Hexanal | 95 | 100.16 | C6H12O | 66-25-1 | 0.10 | 0.04 | 0.07 | 0.07 |
8 | 14.16 | (E)-Hex-2-enal | 91 | 98.14 | C6H10O | 6728-26-3 | 0.04 | 0.01 | 0.04 | 0.04 |
9 | 16.75 | Heptanal | 92 | 114.19 | C7H14O | 111-71-7 | 0.04 | 0.01 | 0.01 | 0.01 |
10 | 19.81 | 1-methyl-pentyl hydroperoxide | 88 | 118.17 | C6H14O2 | 24254-55-5 | 0.11 | 0.01 | 0.05 | 0.02 |
11 | 20.97 | Oct-1-en-3-one | 90 | 126.19 | C8H14O | 4312-99-6 | 0.03 | 0.02 | 0.05 | 0.01 |
12 | 24.17 | Propylcyclohexane | 82 | 126.24 | C9H18 | 696-29-7 | 0.01 | n.d. | 0.02 | n.d. |
13 | 25.31 | (E)-Oct-2-enal | 90 | 126.20 | C8H14O | 2548-87-0 | n.d. | 0.01 | n.d. | n.d. |
14 | 25.79 | 1-Phenylethanone | 95 | 120.15 | C8H8O | 98-86-2 | n.d. | 0.01 | n.d. | n.d. |
15 | 26.05 | Octan-1-ol | 94 | 130.23 | C8H18O | 111-87-5 | n.d. | n.d. | n.d. | 0.03 |
16 | 27.30 | Non-1-en-4-ol | 85 | 142.24 | C9H18O | 35192-73-5 | n.d. | n.d. | 0.03 | 0.01 |
17 | 27.58 | Linalool | 90 | 154.25 | C10H18O | 78-70-6 | n.d. | n.d. | n.d. | 0.01 |
18 | 27.78 | Nonanal | 92 | 142.24 | C9H18O | 124-19-6 | 0.03 | n.d. | 0.02 | 0.02 |
19 | 29.85 | 2,6,6-trimethyl-2-cyclohexene-1,4-dione | 92 | 152.19 | C9H12O2 | 1125-21-9 | n.d. | n.d. | 0.03 | 0.02 |
20 | 32.95 | Decanal | 91 | 156.26 | C10H20O | 112-31-2 | n.d. | n.d. | 0.02 | 0.01 |
21 | 33.64 | 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde | 83 | 152.23 | C10H16O | 4884-24-6 | 0.02 | n.d. | n.d. | n.d. |
22 | 35.67 | 2-(2,6,6-trimethylcyclohexen-1-yl) acetaldehyde | 89 | 166.26 | C11H18O | 472-66-2 | n.d. | n.d. | 0.02 | n.d. |
23 | 35.80 | Ethyl 5-methyl-3,4-dihydro-2H-pyran-4-carboxylate | 83 | 170.21 | C9H14O3 | 38858-64-9 | n.d. | n.d. | 0.05 | n.d. |
24 | 35.92 | 3,5,5-trimethyl-hex-1-ene | 86 | 126.24 | C9H18 | 4316-65-8 | n.d. | 0.02 | 0.29 | 0.03 |
25 | 36.18 | Decan-1-ol | 93 | 158.28 | C10H22O | 112-30-1 | n.d. | 0.01 | 0.09 | 0.36 |
26 | 36.58 | Dec-1-en-3-one | 92 | 154.22 | C10H18O | 56606-79-2 | 0.42 | 0.02 | 0.10 | 0.17 |
27 | 37.17 | Undecan-2-one | 95 | 170.29 | C11H22O | 112-12-9 | n.d. | n.d. | 0.14 | 0.02 |
28 | 37.80 | Undecanal | 96 | 170.29 | C11H22O | 112-44-7 | n.d. | n.d. | n.d. | 0.09 |
29 | 38.26 | (2E,4E)-deca-2,4-dienal | 94 | 152.23 | C10H16O | 25152-84-5 | n.d. | n.d. | 0.05 | 0.02 |
30 | 38.37 | Ethyl cyclohexanecarboxylate | 87 | 156.22 | C9H16O2 | 3289-28-9 | 0.25 | n.d. | 0.54 | 0.07 |
31 | 38.76 | Bicyclo(3.3.1)nonane-2,6-dione | 83 | 152.19 | C9H12O2 | 16473-11-3 | 0.17 | n.d. | 0.35 | 0.08 |
32 | 39.00 | (R)-5,7-dimethyl-1,6-octadiene (Isocitronellene) | 87 | 138.25 | C10H18 | 85006-04-8 | 0.88 | n.d. | 0.04 | 0.03 |
33 | 39.42 | Hexacosan-1-ol | 81 | 382.7 | C26H54O | 506-52-5 | n.d. | n.d. | 0.30 | n.d. |
34 | 40.20 | Eugenol | 95 | 164.20 | C10H12O2 | 97-53-0 | 0.19 | n.d. | n.d. | n.d. |
35 | 41.98 | Nona-3,5-dien-2-one | 84 | 138.21 | C9H14O | 80387-31-1 | 0.11 | n.d. | 0.45 | 0.16 |
36 | 42.18 | 6,10-dimethylundecan-2-one | 95 | 198.34 | C12H26O | 1604-34-8 | 0.05 | n.d. | 0.32 | 0.09 |
37 | 44.29 | Geranylacetone | 84 | 194.31 | C13H22O | 689-67-8 | 0.14 | n.d. | 0.70 | n.d. |
38 | 42.37 | Dodecanal | 92 | 184.32 | C12H24O | 112-54-9 | n.d. | n.d. | n.d. | 0.05 |
39 | 43.40 | (E)-4-[(1R,5S)-2,5,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one | 85 | 206.32 | C14H22O | 79-69-6 | n.d. | n.d. | n.d. | 0.15 |
40 | 44.08 | 3,7,11-trimethyldodecan-1-ol (hexahydrofarnesol) | 92 | 228.41 | C15H32O | 6750-34-1 | n.d. | 0.14 | n.d. | 0.24 |
41 | 44.29 | (Z)-6,10-dimethyl-5,9-undecadien-2-one | 93 | 194.31 | C13H22O | 3879-26-3 | n.d. | n.d. | n.d. | 0.17 |
42 | 44.73 | 3,7,11-trimethyl-dodecan-1-ol | 83 | 228.31 | C15H32O | 6750-34-1 | 0.32 | 0.07 | 0.18 | 0.29 |
43 | 45.08 | (Z)-dec-3-enyl acetate | 89 | 198.30 | C12H22O2 | 81634-99-3 | n.d. | n.d. | 0.18 | n.d. |
44 | 45.17 | Dodecan-1-ol | 94 | 186.33 | C12H26O | 112-53-8 | 1.06 | 1.02 | 1.03 | 3.65 |
45 | 45.91 | (E)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one | 85 | 192.30 | C13H20O | 14901-07-6 | 2.76 | 0.53 | 5.41 | 4.34 |
46 | 46.07 | Tridecan-2-one | 88 | 198.34 | C13H26O | 593-08-8 | 0.12 | 0.36 | 0.67 | 0.31 |
47 | 46.22 | Hexadecane | 96 | 226.44 | C16H34 | 544-76-3 | 0.58 | 0.08 | 0.84 | 1.30 |
48 | 46.34 | Dimethyl 1,4-benzenedicarboxylate | 88 | 194.18 | C10H10O4 | 120-61-6 | n.d. | 0.06 | 0.19 | 1.17 |
49 | 46.89 | n-pentadecan-1-ol | 94 | 228.41 | C15H32O | 629-76-5 | n.d. | n.d. | 0.02 | 0.23 |
50 | 47.33 | (E)-Octadec-5-ene | 91 | 252.47 | C18H36 | 7206-21-5 | n.d. | 0.09 | n.d. | n.d. |
51 | 47.86 | 5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone | 90 | 180.24 | C11H16O2 | 15356-74-8 | 0.27 | n.d. | 0.45 | 0.28 |
52 | 48.31 | (Z)-dodec-5-enoic acid | 95 | 198.30 | C11H22O2 | 2430-94-6 | n.d. | 2.79 | n.d. | n.d. |
53 | 48.92 | (E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | 89 | 222.36 | C15H26O | 40716-66-3 | n.d. | n.d. | 0.08 | n.d. |
54 | 49.12 | Dodecanoic acid (lauric acid) | 97 | 200.31 | C12H24O2 | 143-07-7 | n.d. | 3.78 | 0.22 | 0.08 |
55 | 49.31 | Tetradecan-1-ol | 84 | 214.38 | C14H30O | 112-72-1 | n.d. | 0.26 | 0.37 | 0.31 |
56 | 49.90 | 2-O-(4-methylpentyl) 1-O-octadecyl oxalate | 84 | 426.70 | C26H50O4 | 29590-28-1 | 0.04 | n.d. | 0.11 | 0.05 |
57 | 50.16 | Heptadecane | 92 | 240.46 | C17H36 | 629-78-7 | 0.08 | n.d. | 0.05 | 0.05 |
58 | 50.62 | Tetradecanal | 94 | 212.37 | C14H28O | 124-25-4 | 0.14 | n.d. | 0.08 | 0.20 |
59 | 51.26 | 2-methylhexadecan-1-ol | 90 | 256.46 | C17H36O | 2490-48-4 | n.d. | 0.35 | 0.18 | 0.39 |
60 | 51.42 | Diphenylmethanone | 95 | 182.21 | C13H10O | 119-61-9 | 0.34 | 0.29 | 0.39 | n.d. |
61 | 52.16 | 2-ethyldodecan-1-ol | 88 | 214.38 | C14H30O | 19780-33-7 | 0.24 | n.d. | 0.23 | 0.18 |
62 | 52.30 | alpha-Cadinol | 87 | 222.36 | C15H26O | 481-34-5 | 1.24 | 0.12 | n.d. | n.d. |
63 | 52.65 | Hexadecan-1-ol | 92 | 242.44 | C16H34O | 36653-82-4 | 1.56 | 2.60 | 7.20 | 7.99 |
64 | 52.91 | (E)-heptadec-8-ene | 77 | 238.45 | C17H34 | 54290-12-9 | n.d. | n.d. | 0.11 | 0.09 |
65 | 53.03 | Pentadec-1-ene | 92 | 210.40 | C15H30 | 13360-61-7 | n.d. | n.d. | 0.14 | 2.62 |
66 | 53.22 | 11-pentan-3-ylhenicosane | 89 | 366.70 | C26H54 | 55282-11-6 | 0.65 | 0.43 | 1.11 | 1.41 |
67 | 53.38 | 2-tetradecoxyethanol | 81 | 258.44 | C16H34O2 | 2136-70-1 | 0.24 | 0.32 | 0.44 | 0.37 |
68 | 53.64 | Tridecanal | 93 | 198.34 | C13H26O | 10486-19-8 | 0.60 | 0.37 | 0.81 | 0.43 |
69 | 53.72 | 2-hexadecoxyethanol | 87 | 286.49 | C18H38O2 | 2136-71-2 | 0.25 | n.d. | n.d. | n.d. |
70 | 54.12 | 2-octadecoxyethanol | 90 | 314.54 | C20H42O2 | 2136-72-3 | n.d. | 0.42 | 0.41 | 0.50 |
71 | 54.30 | n-Nonadecan-1-ol | 88 | 284.52 | C19H40O | 1454-84-8 | n.d. | 0.11 | n.d. | n.d. |
72 | 54.52 | (E)-icos-3-ene | 86 | 280.53 | C20H40 | 74685-33-9 | n.d. | 0.14 | n.d. | n.d. |
73 | 54.99 | Myristic acid | 97 | 228.37 | C14H28O2 | 544-63-8 | n.d. | 7.60 | 0.31 | 0.18 |
74 | 55.22 | n-Pentadecanol | 93 | 228.41 | C15H32O | 629-76-5 | 0.46 | 0.85 | 0.72 | 1.19 |
75 | 55.63 | Eicosanoic acid | 87 | 312.53 | C20H40O2 | 506-30-9 | 2.58 | 0.51 | 1.14 | n.d. |
76 | 55.69 | (Z)-Undec-4-enal | 87 | 168.27 | C11H20O | 68820-32-6 | 0.36 | n.d. | n.d. | n.d. |
77 | 56.17 | Isopropyl myristate | 93 | 270.45 | C17H34O2 | 110-27-0 | 0.30 | n.d. | n.d. | n.d. |
78 | 56.63 | 6,10,14-Trimethyl-2-pentadecanone | 96 | 268.5 | C18H36O | 502-69-2 | 2.99 | 0.75 | 5.98 | 5.72 |
79 | 56.89 | 2,3-diisopropyl-naphthalene | 77 | 212.33 | C16H20 | 94133-81-0 | 1.47 | 0.36 | 0.55 | 0.42 |
80 | 56.98 | Oleyl alcohol | 93 | 268.5 | C18H36O | 143-28-2 | n.d. | 0.68 | 4.41 | 5.96 |
81 | 57.18 | bis(2-methylpropyl) benzene-1,2-dicarboxylate | 97 | 278.34 | C16H22O4 | 84-69-5 | 2.11 | 0.51 | 1.11 | n.d. |
82 | 57.52 | Nonadec-1-ene | 93 | 266.50 | C19H38 | 18435-45-5 | n.d. | n.d. | 0.20 | 1.30 |
83 | 58.11 | Farnesyl acetone | 90 | 266.43 | C18H30O | 1117-52-8 | 0.93 | 0.57 | 1.28 | 1.05 |
84 | 58.62 | Palmitoleic acid | 95 | 254.40 | C16H30O2 | 373-49-9 | 2.79 | 11.94 | n.d. | n.d. |
85 | 58.90 | Palmitic acid | 93 | 256.42 | C16H32O2 | 57-10-3 | 40.15 | 31.92 | 26.81 | 18.62 |
86 | 60.14 | Arachidonic acid | 90 | 304.46 | C20H32O2 | 506-32-1 | 0.96 | 1.45 | 0.14 | 0.27 |
87 | 60.30 | Methyl Arachidonate | 83 | 318.49 | C21H34O2 | 2566-89-4 | 4.00 | 2.49 | 1.55 | 1.74 |
88 | 60.81 | n-Nonadecan-1-ol | 89 | 284.52 | C19H40O | 1454-84-8 | 1.67 | 3.13 | 4.13 | 4.34 |
89 | 60.84 | (Z,Z)-2,13-Octadecadien-1-ol | 85 | 266.46 | C18H34 | 123551-47-3 | 0.21 | n.d. | 1.67 | n.d. |
90 | 61.21 | 5-dodecyloxolan-2-one | 90 | 254.41 | C16H30O2 | 730-46-1 | 1.44 | 0.21 | 1.94 | 0.88 |
91 | 61.29 | Phytol | 96 | 296.53 | C20H40O | 150-86-7 | 3.97 | 2.90 | 5.76 | 14.20 |
92 | 61.69 | Oleic acid | 91 | 282.46 | C18H34O2 | 112-80-1 | 0.23 | 1.63 | 0.12 | 0.29 |
93 | 61.81 | Heptadecyl heptadecanoate | 81 | 508.92 | C34H68O2 | n.a. | 0.22 | n.d. | 0.12 | 0.40 |
94 | 61.99 | Ascorbyl palmitate | 70 | 414.53 | C22H38O7 | 137-66-6 | 0.32 | n.d. | n.d. | 0.12 |
95 | 62.39 | Octadecyl propan-2-yl sulphite | 82 | 376.60 | C21H44O3S | n.a. | 0.22 | n.d. | n.d. | 0.19 |
96 | 62.58 | Tetradecyl benzoate | 78 | 318.50 | C21H34O2 | 70682-72-3 | 1.10 | 4.37 | 0.53 | 0.09 |
97 | 63.04 | Pentadecyl benzoate | 80 | 332.50 | C22H36O2 | n.a. | 0.07 | 0.50 | 0.10 | 0.04 |
98 | 63.98 | Tridecyl benzoate | 88 | 304.50 | C20H32O2 | 29376-83-8 | 0.16 | 1.28 | 0.40 | 0.05 |
99 | 64.22 | 2-(Octadecyloxy)ethanol | 91 | 314.55 | C20H42O2 | 9005-00-9 | 0.28 | 1.04 | 0.76 | 1.46 |
100 | 64.39 | Stearic acid | 80 | 284.48 | C18H36O2 | 57-11-4 | 0.36 | 0.09 | n.d. | n.d. |
101 | 64.96 | 1-Decylsulfonyldecane | 79 | 346.61 | C20H42O2S | 111530-37-1 | 0.13 | n.d. | n.d. | 0.14 |
102 | 66.14 | Icosane | 94 | 282.55 | C20H42 | 112-95-8 | 0.16 | n.d. | 0.30 | 0.11 |
103 | 67.28 | Nonacosane | 93 | 408.79 | C29H60 | 630-03-5 | 0.34 | 0.05 | 0.09 | 0.14 |
104 | 70.37 | Squalene | 90 | 410.73 | C30H50 | 111-02-4 | 0.18 | 0.04 | 0.20 | 0.07 |
TOTAL IDENTIFIED COMPOUNDS (from peak total area) | 84.37 | 89.43 | 85.44 | 87.41 |
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Generalić Mekinić, I.; Čagalj, M.; Tabanelli, G.; Montanari, C.; Barbieri, F.; Skroza, D.; Šimat, V. Seasonal Changes in Essential Oil Constituents of Cystoseira compressa: First Report. Molecules 2021, 26, 6649. https://doi.org/10.3390/molecules26216649
Generalić Mekinić I, Čagalj M, Tabanelli G, Montanari C, Barbieri F, Skroza D, Šimat V. Seasonal Changes in Essential Oil Constituents of Cystoseira compressa: First Report. Molecules. 2021; 26(21):6649. https://doi.org/10.3390/molecules26216649
Chicago/Turabian StyleGeneralić Mekinić, Ivana, Martina Čagalj, Giulia Tabanelli, Chiara Montanari, Federica Barbieri, Danijela Skroza, and Vida Šimat. 2021. "Seasonal Changes in Essential Oil Constituents of Cystoseira compressa: First Report" Molecules 26, no. 21: 6649. https://doi.org/10.3390/molecules26216649
APA StyleGeneralić Mekinić, I., Čagalj, M., Tabanelli, G., Montanari, C., Barbieri, F., Skroza, D., & Šimat, V. (2021). Seasonal Changes in Essential Oil Constituents of Cystoseira compressa: First Report. Molecules, 26(21), 6649. https://doi.org/10.3390/molecules26216649