A Year in the Life of Sea Fennel: Annual Phytochemical Variations of Major Bioactive Secondary Metabolites
Abstract
:1. Introduction
2. Materials and Methods
2.1. Reagents
2.2. Plant Material
2.3. Extractions of Essential Oils, Phenolics and Carotenoids
2.4. Gas Chromatography–Mass Spectrometry
2.5. Ultra High-Performance Liquid Chromatography
2.5.1. Phenolics
2.5.2. Carotenoids
2.6. Statistical Analyses
2.6.1. Analysis of Variance
2.6.2. Pearson Correlation Coefficient
2.6.3. Principal Component Analysis
2.6.4. Hierarchical Cluster Analysis
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | RI | RIL | January | February | March | April | May | June | July | August | September | October | November | December |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
α-Pinene | 927 | 932 | 8.14 ± 0.16 a | 3.8 ± 0.10 b | 7.68 ± 0.00 a | 3.15 ± 0.02 b,c | 2.89 ± 0.17 c | 1.57 ± 0.00 d | 0.48 ± 0.03 e | 0.61 ± 0.00 f | 0.56 ± 0.01 e,f | 1.34 ± 0.10 d | 1.07 ± 0.01 g | 0.82 ± 0.04 h |
Sabinene | 966 | 969 | 6.81 ± 0.15 a | 0.28 ± 0.00 b | 0.30 ± 0.01 b | 0.15 ± 0.00 c | 0.59 ± 0.05 d | 0.97 ± 0.00 e | 1.75 ± 0.03 f | 4.19 ± 0.04 g | 11.38 ± 0.24 h | 8.83 ± 0.58 i | 2.24 ± 0.04 j | 1.82 ± 0.11 f,j |
β-Myrcene | 985 | 988 | 1.33 ± 0.03 a | 0.56 ± 0.02 b,c | 0.56 ± 0.01 b,c | 0.41 ± 0.01 d | 0.26 ± 0.01 e | 0.47 ± 0.01 b,d | 0.43 ± 0.02 d | 0.66 ± 0.01 c,e | 1.01 ± 0.05 f | 1.55 ± 0.15 a | 0.72 ± 0.02 e | 0.91 ± 0.04 f |
α-Terpinene | 1011 | 1014 | 1.06 ± 0.03 a | 0.05 ± 0.02 b,c | 0.04 ± 0.00 b,d | 0.04 ± 0.02 b | 0.11 ± 0.00 b,e,f | 0.23 ± 0.01 e,g | 0.19 ± 0.04 e,g | 0.50 ± 0.02 a,g | 0.51 ± 0.00 a,g | 0.35 ± 0.04 a,f,g | 0.14 ± 0.01 c,d,f,g | 0.16 ± 0.02 c,d,f,g |
Limonene | 1023 | 1024 | 58.74 ± 0.85 a | 71.00 ± 1.53 b | 74.19 ± 0.06 b | 73.72 ± 0.09 b | 81.79 ± 0.72 c,d | 83.52 ± 0.23 c,d | 82.13 ± 0.59 c,d | 84.53 ± 0.50 c,d | 76.31 ± 0.49 b,c | 72.72 ± 2.62 b | 82.98 ± 0.87 d | 72.46 ± 1.33 b |
(Z)-β-Ocimene | 1032 | 1032 | 11.65 ± 0.06 a | 4.86 ± 0.16 b | 6.48 ± 0.07 c | 6.44 ± 0.04 c | 3.17 ± 0.15 d | 4.70 ± 0.06 b | 3.83 ± 0.03 d,e | 4.10 ± 0.10 b,e | 4.72 ± 0.16 b | 7.39 ± 0.62 c | 6.40 ± 0.16 c | 4.84 ± 0.23 b |
γ-Terpinene | 1052 | 1054 | 2.28 ± 0.05 a | 0.18 ± 0.01 b,c | 0.17 ± 0.01 b,c | tr. | 0.87 ± 0.03 d,e | 0.89 ± 0.02 d,e | 0.48 ± 0.02 f | 0.98 ± 0.04 d,g | 1.04 ± 0.03 d | 0.83 ± 0.09 e,g | 0.33 ± 0.01 c,f | 0.42 ± 0.03 f |
(Z)-p-Mentha-2,8-dien-1-ol | 1115 | 1133 | 0.33 ± 0.01 a | 1.45 ± 0.06 b | 0.90 ± 0.03 c | 1.30 ± 0.01 b | 0.75 ± 0.00 c,d | 0.37 ± 0.02 a,e | 0.56 ± 0.11 d,e | tr. | tr. | 0.31 ± 0.03 a | 0.24 ± 0.04 a | 0.84 ± 0.04 c |
Terpinen-4-ol | 1171 | 1174 | 0.90 ± 0.05 a,h | 0.38 ± 0.01 b,c | 0.24 ± 0.02 b | tr. | 0.68 ± 0.01 a,c,d | 0.47 ± 0.05 b,d,e | 1.47 ± 0.03 f,g | 1.25 ± 0.08 f,h | 1.72 ± 0.05 g | 0.59 ± 0.09 a,b | 0.64 ± 0.18 a,c,e | 0.68 ± 0.04 a,c,e |
α-Terpineol | 1184 | 1186 | 0.30 ± 0.02 a | 0.93 ± 0.09 b | tr. | n.d. | n.d. | 0.19 ± 0.01 a | 0.66 ± 0.06 b,c | 0.29 ± 0.02 a | 0.21 ± 0.02 a | 0.25 ± 0.04 a | 0.43 ± 0.05 a,c | 2.23 ± 0.012 d |
(E)-Carveol | 1213 | 1215 | 0.29 ± 0.01 a | 1.18 ± 0.04 b | 0.58 ± 0.00 c | 0.58 ± 0.06 c | 1.07 ± 0.02 b,d,f | 0.99 ± 0.04 b,e,f | 0.91 ± 0.09 d,e,f | tr. | 0.19 ± 0.01 a | 0.25 ± 0.04 a | 0.29 ± 0.02 a | 0.85 ± 0.03 f |
Limonene-1,2-diol | 1322 | 1343 | 0.17 ± 0.01 a | 0.63 ± 0.04 b | 0.31 ± 0.01 c | 0.25 ± 0.03 a,c | 1.01 ± 0.05 d | 0.33 ± 0.00 c | 0.49 ± 0.02 e | tr. | tr. | tr. | n.d. | tr. |
Tetradecane | 1400 | 1400 | 0.68 ± 0.1 a,b | 3.19 ± 0.02 c | 1.57 ± 0.04 d | 4.22 ± 0.24 e | 0.87 ± 0.06 a,e | tr. | 1.19 ± 0.10 a,d | 0.39 ± 0.04 b,e | 0.23 ± 0.02 b,e | 0.96 ± 0.15 a | 0.37 ± 0.09 b,e | 3.38 ± 0.03 c |
Germacrene B | 1548 | 1559 | 1.51 ± 0.06 a | 1.28 ± 0.10 a | 1.34 ± 0.06 a | 0.62 ± 0.02 b | tr. | tr. | n.d. | n.d. | n.d. | tr. | 0.29 ± 0.13 b,c | 0.12 ± 0.12 c |
Hexadecane | 1600 | 1600 | 0.72 ± 0.00 a | 3.10 ± 0.34 b | 1.47 ± 0.1 c | 4.04 ± 0.09 d | 0.50 ± 0.1 a | tr. | 0.69 ± 0.07 a | 0.28 ± 0.01 a | tr. | 0.68 ± 0.13 a | 0.17 ± 0.03 a | 3.00 ± 0.16 b |
Octadecane | 1800 | 1800 | 0.33 ± 0.03 a,b,c | 1.57 ± 0.25 d | 0.72 ± 0.01 a,e | 2.06 ± 0.04 f | tr. | n.d. | 0.13 ± 0.01 b,g | tr. | tr. | 0.38 ± 0.07 c,h | n.d. | 1.75 ± 0.37 i |
Monoterpenes | 92.70 | 81.20 | 89.92 | 84.31 | 90.43 | 93.24 | 89.66 | 96.26 | 96.55 | 94.59 | 94.42 | 82.67 | ||
Monoterpenoides | 2.47 | 6.10 | 3.12 | 3.68 | 5.52 | 2.94 | 5.11 | 1.72 | 2.33 | 1.56 | 1.91 | 5.20 | ||
Sesquiterpenes | 1.51 | 1.28 | 1.34 | 0.62 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 2.03 | 0.55 | 8.13 | ||
Aldehydes | 0.52 | 0.91 | 0.56 | 0.48 | 0.45 | 0.58 | 0.28 | 0.15 | 0.19 | 0.38 | 0.17 | 0.48 | ||
Cyclic ketones | 0.00 | 0.63 | 0.00 | 0.08 | 1.23 | 1.55 | 0.87 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | ||
Saturated hydrocarbons | 1.73 | 7.86 | 3.76 | 10.33 | 1.37 | 0.19 | 2.02 | 0.67 | 0.23 | 2.03 | 0.55 | 8.13 | ||
Total chromatogram identified (%) | 98.93 | 97.98 | 98.70 | 99.49 | 98.99 | 98.50 | 97.94 | 98.80 | 99.30 | 98.57 | 97.35 | 96.60 |
Climatic Parameter | Average Temperature (°C) | Relative Humidity (%) | Average Wind Strength | Relative Cloud Cover (1/10) | |
---|---|---|---|---|---|
Compound | Essential oils | ||||
α-Pinene | r = −0.641 | r = 0.097 | r = 0.508 | r = 0.255 | |
p= 0.025 | p = 0.765 | p = 0.092 | p = 0.425 | ||
Limonene | r = 0.694 | r = −0.318 | r = −0.299 | r = −0.242 | |
p = 0.012 | p = 0.314 | p = 0.346 | p = 0.448 | ||
Terpinen-4-ol | r = 0.647 | r = −0.300 | r = −0.150 | r = −0.390 | |
p = 0.023 | p = 0.344 | p = 0.642 | p = 0.210 | ||
α-Terpineol | r = −0.277 | r = 0.623 | r = −0.135 | r = 0.191 | |
p = 0.384 | p = 0.030 | p = 0.677 | p = 0.553 | ||
Germacrene B | r = −0.770 | r = 0.060 | r = 0.593 | r = 0.097 | |
p = 0.004 | p = 0.854 | p = 0.042 | p = 0.765 | ||
Hexadecane | r = −0.602 | r = 0.240 | r = 0.195 | r = 0.199 | |
p = 0.038 | p = 0.453 | p = 0.543 | p = 0.536 | ||
Octadecane | r = −0.627 | r = 0.312 | r = 0.179 | r = 0.240 | |
p = 0.029 | p = 0.323 | p = 0.578 | p = 0.453 | ||
Phenolics | |||||
Chlorogenic acid | r = 0.794 | r = −0.497 | r = −0.523 | r = −0.330 | |
p = 0.002 | p = 0.101 | p = 0.081 | p = 0.296 | ||
Criptochlorogenic | r = 0.887 | r = −0.623 | r = −0.388 | r = −0.617 | |
p = 0.0001 | p = 0.030 | p = 0.212 | p = 0.032 | ||
Carotenoids | |||||
Lutein | r = 0.249 | r = 0.588 | r = −0.306 | r = 0.375 | |
p = 0.436 | p = 0.044 | p = 0.333 | p = 0.229 |
Compound | January | February | March | April | May | June | July | August | September | October | November | December |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Phenolics (mg/g) | ||||||||||||
Neochlorogenic acid | 0.5 ± 0.00 a | 0.05 ± 0.00 b | 0.23 ± 0.00 c | 0.05 ± 0.04 b | 0.25 ± 0.00 c | 0.98 ± 0.00 d | 2.84 ± 0.00 e | 3.52 ± 0.01 f | 5.05 ± 0.00 g | 1.33 ± 0.01 h | 0.05 ± 0.00 a | 0.23 ± 0.00 c |
Chlorogenic acid | 0.51 ± 0.01 a | 1.8 ± 0.02 b | 28.89 ± 0.02 c | 16.68 ± 0.03 d | 52.13 ± 0.04 e | 60.59 ± 0.09 f | 49.66 ± 0.02 e | 33.84 ± 0.06 f | 30.43 ± 0.05 c | 20.94 ± 0.00 g | 0.46 ± 0.02 h | 3.74 ± 0.01 i |
Criptochlorogenic acid | 0.06 ± 0.00 a | 0.10 ± 0.00 b | 0.72 ± 0.00 c | 0.22 ± 0.01 d | 0.67 ± 0.06 c | 2.52 ± 0.04 e | 5.14 ± 0.00 f,g | 4.74 ± 0.07 f | 5.90 ± 0.00 g | 1.86 ± 0.06 h | 0.09 ± 0.00 b | 0.37 ± 0.00 i |
Carotenoids (mg/kg) | ||||||||||||
Neoxantin | 8.72 ± 0.14 a | n.d. | n.d. | n.d. | 4.15 ± 0.18 b | 1.95 ± 0.14 c,d | 1.88 ± 0.02 c,e | 2.18 ± 0.09 d,e | 7.63 ± 0.05 a | 5.64 ± 0.05 f | 8.27 ± 0.01 a | n.d. |
Violaxanthin | 4.22 ± 0.06 a | 13.64 ± 0.05 b | 14.30 ± 0.82 b | n.d. | n.d. | 4.85 ± 0.03 a | n.d. | n.d. | n.d. | 15.07 ± 0.04 b | 5.44 ± 0.88 a | 5.17 ± 0.16 a |
Lutein | 90.77 ± 2.00 a,b,c | n.d. | 3.13 ± 0.12 d | 5.65 ± 0.35 e | 125.63 ± 0.01 f | 85.90 ± 0.07 a | 55.60 ± 1.12 g | 108.54 ± 0.54 h | 98.45 ± 0.56 b,h | 99.52 ± 1.23 c,h | 74.58 ± 0.20 i | 182.48 ± 0.13 j |
β-Carotene | 52.89 ± 1.33 a | 24.76 ± 1.29 b | 72.51 ± 0.62 c | 103.03 ± 0.29 d | 111.01 ± 0.41 d,e | 88.62 ± 2.395 f | 34.87 ± 0.53 g | 173.79 ± 1.99 h | 118.00 ± 2.41 e | 67.17 ± 0.21 c | 76.94 ± 2.02 c,i | 85.59 ± 1.21 f,i |
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Popović, M.; Radman, S.; Generalić Mekinić, I.; Ninčević Runjić, T.; Urlić, B.; Veršić Bratinčević, M. A Year in the Life of Sea Fennel: Annual Phytochemical Variations of Major Bioactive Secondary Metabolites. Appl. Sci. 2024, 14, 3440. https://doi.org/10.3390/app14083440
Popović M, Radman S, Generalić Mekinić I, Ninčević Runjić T, Urlić B, Veršić Bratinčević M. A Year in the Life of Sea Fennel: Annual Phytochemical Variations of Major Bioactive Secondary Metabolites. Applied Sciences. 2024; 14(8):3440. https://doi.org/10.3390/app14083440
Chicago/Turabian StylePopović, Marijana, Sanja Radman, Ivana Generalić Mekinić, Tonka Ninčević Runjić, Branimir Urlić, and Maja Veršić Bratinčević. 2024. "A Year in the Life of Sea Fennel: Annual Phytochemical Variations of Major Bioactive Secondary Metabolites" Applied Sciences 14, no. 8: 3440. https://doi.org/10.3390/app14083440