NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters
Abstract
:1. Introduction
2. Results and Discussion
2.1. Sample Collection
2.2. Acquisition, Data Processing and Multivariate Analysis
Geographical Origin, Olive Cultivar, Processing Procedure
2.3. Statistical Total Correlation Spectroscopy (STOCSY) and Biomarker Identification
2.4. Quality and Authentication Assessment
3. Materials and Methods
3.1. Collection of Samples
3.2. Sample Preparation
3.2.1. Lyophilization
3.2.2. Extraction Protocol
3.3. NMR Analysis
3.3.1. Preparation of NMR Samples
3.3.2. NMR Experimental Parameters
3.4. Computational Processing and Multivariate Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: All analyzed samples are available for further evaluation in the Division of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, National and Kapodistrian University of Athens. |
Region | Subregion | Variety | Processing Type | Sample Number | |
---|---|---|---|---|---|
1 | Makedonia | Chalkidiki | Chalkidikis | Spanish (green) | 9 |
2 | Kavala | Chalkidikis | 6 | ||
3 | Sterea Ellada | Magnesia | Konservolia | Greek (black) | 6 |
4 | Fthiotida | Konservolia | 9 | ||
5 | Fthiotida | Kalamon | 1 | ||
6 | Aitoloakarnania | Kalamon | 14 | ||
7 | Peloponnese | Messinia | Kalamon | 10 | |
8 | Lakonia | Kalamon | 5 |
No | Compound | δ1H (Multiplicity, J in Hz, Assignment) | Ref. |
---|---|---|---|
1 | Tyr | 6.96 (d, J = 8.5 Hz, H-2, H-6), 6.64 (d, J = 8.5 Hz, H-3, H-5), 3.62 (t, J = 7.2 Hz, H-8), 2.65 (t, J = 7.2 Hz, H-7) | [56] |
2 | HT | 6.62 (d, J = 8.0 Hz, H-5), 6.59 (d, J = 1.9 Hz, H-2), 6.46 (dd, J = 1.9/8.0 Hz, H-6), 3.61 (t, J = 7.2 Hz, H-8), 2.60 (t, J = 7.2 Hz, H-7) | [57] |
3 | Ver | 7.53 (d, J = 15.9 Hz, H-7′’’), 7.00 (d, J = 2.0 Hz, H-2′’’), 6.89 (dd, J = 2.0/8.2 Hz, H6′’’), 6.72 (d, J = 8.2 Hz, H-5′’’), 6.63 (m, H-2), 6.61 (m, H-5), 6.50 (dd, J = 2.0/8.0 Hz, H-6), 6.21 (d, J = 15.9 Hz, H-8′’’), 5.13 (d, J = 1.7 Hz, H-1′’), 4.85 (m, H-4′), 4.32 (d, J = 8.0 Hz, H-1′), 3.98-2.73(m, H-7, H-8, H-2′, H-3′, H-5′, H-6′, H-2′’, H-3′’, H-4′’, H-5′’), 1.03 (d, J = 6.2 Hz, H-6′’) | [58] |
4 | Lut | 7.32 (dd, J = 2.2/9.0 Hz, H-6′), 7.32 (d, J = 2.2 Hz, H-2′), 6.85 (d, J = 9.0 Hz, H-5′), 6.48 (s, H-3), 6.39 (d, J = 2.1 Hz, H-8), 6.15 (d, J = 2.1 Hz, H-6) | [59] |
5 | Quer | 7.67 (d, J = 2.2 Hz, H-2′), 7.57 (dd, J = 2.2/8.5 Hz, H-6′), 6.83 (d, J = 8.5 Hz, H-5′), 6.34 (d, J = 2.0 Hz, H-8), 6.13 (d, J = 2.0 Hz, H-6) | [60] |
6 | MA | 5.19 (brt, J = 3.6 Hz, H-12), 3.55 (m, H-2), 2.85 (d, J = 9.6 Hz, H-3), 2.80 (dd, J = 4.1/14.1 Hz, H-18), 1.10 (s, H-27), 0.95 (s, H-24), 0.94 (s, H-23), 0.88 (s, H-30), 0.85 (s, H-29), 0.76 (s, H-26), 0.75 (s, H-25) | [61] |
7 | OA | 5.18 (brt, J = 3.5 Hz, H-12), 3.08 (dd, J = 4.9/11.7 Hz, H-3), 2.79 (dd, J = 4.1/14.3 Hz, H-18), 1.09 (s, H-27), 0,91 (s, H-23), 0.88 (s, H-25, H-30), 0.85 (s, H-29), 0.76 (s, H-26), 0.71 (s, H-24) | [61] |
8 | SA | 2.46 (s, H-2, H-3) | [62] |
9 | LA | 4.04 (q, J = 6.9 Hz, H-2), 1.29 (d, J = 6.9 Hz, H-3) | [62] |
10 | PA | 2.13 (q, J = 7.6 Hz, H-2), 1.03 (t, J = 7.6 Hz, H-3) | [63] |
11 | AA | 1.85 (s, H-2) | [64] |
12 | FA | 8.45 (s) | [64] |
13 | TAGs | 5.28 (m, olefinic protons), 5,25 (m, glyceryl group, H-2), 4.08 (dd, J = 4.4/11.4 Hz, glyceryl group, H-1a, H-3a), 4.01 (dd, 6.2/11.4 Hz, glyceryl group, H-1b, H-3b), 2.20 (t, J = 7.5 Hz, acyl groups, -OCO-CH2-), 2.02-1.95 (m, acyl groups, allylic protons), 1.54 (m, acyl groups, -OCO-CH2-CH2-), 1.34-1.18 (m, acyl groups, -(CH2)n-), 0.83 (t, 7.0, saturated/ monosaturated methyl group) | [65] |
14 | Lin* | 5.28 (m, olefinic protons), 5,25 (m, glyceryl group, H-2), 4.08 (dd, J = 4.4/11.4 Hz, glyceryl group, H-1a, H-3a), 4.01 (dd, 6.2/11.4 Hz, glyceryl group, H-1b, H-3b), 2.71 (t, J = 6.7 Hz, H-11, bis-allylic proton), 2.20 (t, J = 7.5 Hz, acyl groups, -OCO-CH2-), 2.02-1.95 (m, acyl groups, allylic protons), 1.54 (m, acyl groups, -OCO-CH2-CH2-), 1.34-1.18 (m, acyl groups, -(CH2)n-), 0.84 (t, J = 7.0 Hz, H-18) | [65] |
15 | G** | 3.59 (m, H-2), 3.53 (dd, J = 4.8/11.2 Hz, H-1a, H-3a), 3.46 (dd, J = 6.0/11.1 Hz, H-1b, H-3b) | [66] |
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Beteinakis, S.; Papachristodoulou, A.; Gogou, G.; Katsikis, S.; Mikros, E.; Halabalaki, M. NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters. Molecules 2020, 25, 3339. https://doi.org/10.3390/molecules25153339
Beteinakis S, Papachristodoulou A, Gogou G, Katsikis S, Mikros E, Halabalaki M. NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters. Molecules. 2020; 25(15):3339. https://doi.org/10.3390/molecules25153339
Chicago/Turabian StyleBeteinakis, Stavros, Anastasia Papachristodoulou, Georgia Gogou, Sotirios Katsikis, Emmanuel Mikros, and Maria Halabalaki. 2020. "NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters" Molecules 25, no. 15: 3339. https://doi.org/10.3390/molecules25153339