Table 3.
Phytochemical identification and quantification of the OL extracts from Spain, Italy, Greece, and Portugal.
| Compound | Formula | m/z | Error (ppm) | Spain | Italy | Greece | Portugal |
|---|---|---|---|---|---|---|---|
| Sugars | |||||||
| Sorbitol | C6H14O6 | 181.0723 | −2.61 | 9.76 ± 5.82 b | 3.47 ± 3.4 a | 10.16 ± 5.57 b | 8.39 ± 2.35 ab |
| D-Sedoheptulose | C7H14O7 | 209.0671 | −1.91 | 0.53 ± 0.2 | 0.35 ± 0.21 | 0.69 ± 0.31 | 0.58 ± 0.11 |
| D-glucose/D-fructose/D-galactose | C6H12O6 | 179.0563 | −0.73 | 0.76 ± 0.21 b | 0.36 ± 0.14 a | 0.74 ± 0.27 b | 0.77 ± 0.22 b |
| D-xylose/L-arabinose | C5H10O5 | 149.0456 | −0.35 | 0.31 ± 0.09 | 0.19 ± 0.07 | 0.25 ± 0.14 | 0.27 ± 0.05 |
| Disccharide | C12H20O10 | 323.0982 | 0.6 | 0.28 ± 0.07 ab | 0.33 ± 0.1 b | 0.23 ± 0.11 a | 0.27 ± 0.06 ab |
| Methyl disaccharide | C11H20O9 | 295.1036 | −0.3 | 0.5 ± 0.15 a | 0.27 ± 0.21 b | 0.39 ± 0.18 ab | 0.41 ± 0.07 ab |
| Organic acids | |||||||
| Gluconic acid | C6H12O7 | 195.0517 | −3.43 | 8.02 ± 4.38 | 5.4 ± 6.53 | 10.23 ± 8.1 | 5.14 ± 3.29 |
| Ribonic acid | C5H10O6 | 165.041 | −3.22 | 3.89 ± 1.34 b | 1.46 ± 0.98 a | 3.55 ± 1.76 b | 3.6 ± 0.77 b |
| Quinic acid | C7H12O6 | 191.0567 | −2.85 | 8.4 ± 4.92 a | 6.61 ± 6.39 a | 13.87 ± 7.06 b | 8.84 ± 3.87 a |
| Malic acid | C4H6O5 | 133.0148 | −4.03 | 0.97 ± 0.75 | 3.51 ± 1.42 | 2.93 ± 1.33 | 0.97 ± 0.33 |
| Citric acid/Isocitric acid | C6H8O7 | 191.0201 | −1.63 | 1.03 ± 0.75 | 0.78 ± 0.19 | 1.7 ± 1.07 | 0.39 ± 0.19 |
| Secoiridoids | |||||||
| Oleuropein | C25H32O13 | 539.177 | 0.2 | 10.27 ± 18.69 | 4.72 ± 9.04 | 0.11 ± 0.06 | 2.69 ± 6.61 |
| 1-β-D-Glucopyranosyl acyclodihydroelenolic acid isomer 1 | C17H28O11 | 407.1562 | −0.42 | 0.37 ± 0.17 | 0.32 ± 0.13 | 0.4 ± 0.22 | 0.33 ± 0.19 |
| Decarboxymethyl elenolic acid dialdehyde form isomer 1 (Hydroxylated) | C10H14O5 | 213.0769 | 0.09 | 0.19 ± 0.1 a | - | 0.18 ± 0.03 b | 0.16 ± 0.09 a |
| Oleoside/secologanoside | C16H22O11 | 389.109 | −0.05 | 1.61 ± 1.13 | - | - | 0.93 ± 1.03 |
| 1-β-D-Glucopyranosyl acyclodihydroelenolic acid isomer 2 | C17H28O11 | 407.1561 | −0.23 | 0.67 ± 0.37 a | 0.18 ± 0.07 a | 0.67 ± 0.45 ab | 1.21 ± 0.76 b |
| Decarboxymethyl elenolic acid dialdehyde form (Hydrated) | C9H14O5 | 201.0772 | −1.63 | 0.15 ± 0.17 | 0.11 ± 0.07 | 0.32 ± 0.14 | - |
| Decarboxymethyl elenolic acid dialdehyde form isomer 2 (Hydroxylated) | C9H12O5 | 199.0615 | −1.21 | 0.28 ± 0.14 | 0.33 ± 0.17 | 0.67 ± 0.8 | 0.42 ± 0.33 |
| Decarboxylated form of hydroxy elenolic acid isomer 2 | C10H14O5 | 213.0768 | 0.11 | - | - | 0.5 ± 0.12 | - |
| Oleoside methyl ester | C17H24O11 | 403.1243 | 0.94 | 1.03 ± 1.18 | 0.46 ± 0.6 | - | 0.7 ± 0.72 |
| Aldehydic form of decarboxymethyl elenolic acid | C10H16O5 | 215.0929 | −1.69 | 0.24 ± 0.19 | 0.13 ± 0.12 | 0.51 ± 0.52 | 0.07 ± 0.01 |
| Hydroxyoleuropein | C25H32O14 | 555.1712 | 1.45 | 0.48 ± 0.58 | 0.52 ± 0.26 | - | 0.54 ± 0.56 |
| Oleuropein diglucoside | C31H42O18 | 701.2288 | 1.85 | 0.31 ± 0.12 | - | - | - |
| Oleuropein isomer | C25H32O13 | 539.1767 | 0.78 | 3.15 ± 2.27 | 1.19 ± 1.67 | - | - |
| Ligstroside | C25H32O12 | 523.1815 | 1.36 | 0.86 ± 0.12 | - | - | - |
| Flavonoids | |||||||
| Luteolin-7,4-O-diglucoside/Rutin | C27H30O16 | 609.1451 | 1.84 | 0.15 ± 0.05 | - | - | 0.07 ± 0.05 |
| Luteolin rutinoside isomer 2 | C27H30O15 | 593.1505 | 1.39 | 0.1 ± 0.05 | - | 0.07 ± 0.05 | - |
| Luteolin-7-O-glucoside | C21H20O11 | 447.0934 | 0.12 | 1.14 ± 0.67 | 1.74 ± 2.37 | 0.62 ± 0.53 | 1.1 ± 1.22 |
| Apigenin-7-O-rutinoside | C27H30O14 | 577.1559 | 0.7 | 0.52 ± 0.22 b | 0.18 ± 0.05 a | 0.32 ± 0.11 a | 0.34 ± 0.08 ab |
| Taxifolin | C15H12O7 | 303.0509 | 0.52 | 0.04 ± 0.04 | - | - | - |
| Apigenin-7-O-glucoside | C21H20O10 | 431.0981 | 0.87 | 0.29 ± 0.16 | 0.5 ± 0.36 | 0.09 ± 0.04 | 0.38 ± 0.13 |
| Luteolin glucoside | C21H20O11 | 447.0934 | 0.06 | 4.96 ± 2.06 b | 2.9 ± 2.06 ab | 1.28 ± 0.93 a | 3.43 ± 1.19 ab |
| Chrysoeriol-7-O-glucoside/Diosmetin-7-O-glucoside | C22H22O11 | 461.1086 | 0.86 | 0.62 ± 0.16 b | 0.53 ± 0.35 ab | 0.27 ± 0.15 a | 0.67 ± 0.16 ab |
| Azelaic acid | C9H16O4 | 187.0979 | −1.55 | 0.5 ± 0.36 a | 2.02 ± 1.47 b | 0.13 ± 0.05 a | 0.27 ± 0.1 a |
| Luteolin glucoside | C21H20O11 | 447.0932 | 0.46 | 0.45 ± 0.12 b | 0.23 ± 0.07 a | 0.45 ± 0.24 ab | 0.4 ± 0.11 ab |
| (+)-Eriodictyol | C15H12O6 | 287.0565 | −1.05 | 0.19 ± 0.09 b | - | - | 0.08 ± 0.08 a |
| Isorhamnetin-3-O-β-D-(6-p-coumaroyl) glucoside | C31H28O14 | 623.1395 | 1.94 | 0.03 ± 0.02 | 0.1 ± 0.12 | 0.04 ± 0.05 | 0.08 ± 0.08 |
| Luteolin | C15H10O6 | 285.0412 | −2.43 | 0.27 ± 0.19 | 0.38 ± 0.18 | 0.43 ± 0.3 | 0.19 ± 0.08 |
| Apigenin | C15H10O5 | 269.046 | −1.49 | 0.14 ± 0.08 a | 0.73 ± 0.27 b | 0.18 ± 0.16 a | 0.12 ± 0.08 a |
| Diosmetin | C16H12O6 | 299.0562 | −0.32 | 0.19 ± 0.09 a | 0.51 ± 0.13 c | 0.32 ± 0.16 b | 0.16 ± 0.07 a |
| Luteolin rutinoside isomer 1 | C27H30O15 | 593.1502 | 1.79 | - | 0.03 ± 0.02 | - | - |
| Phenolic alcohols | |||||||
| Hydroxytyrosol | C8H10O3 | 153.0556 | −0.84 | 0.12 ± 0.09 a | 0.35 ± 0.13 b | 0.05 ± 0.01 a | 0.12 ± 0.13 a |
| Hydroxytyrosol glucoside | C14H20O8 | 315.1086 | −0.08 | 0.36 ± 0.46 | 0.50 ± 1 | 0.36 ± 0.38 | 0.33 ± 0.45 |
| 4-Ethylguaiacol | C9H12O2 | 151.0764 | 0.36 | 0.1 ± 0.06 | 0.09 ± 0.02 | 0.15 ± 0.11 | 0.08 ± 0.03 |
| Iridoids | |||||||
| Loganic acid | C16H24O10 | 375.1297 | 0.15 | 0.26 ± 0.06 b | 0.11 ± 0.11 a | 0.13 ± 0.09 a | 0.26 ± 0.1 b |
| 7-Epiloganin | C17H26O10 | 389.1457 | −0.58 | 0.7 ± 0.21 ab | 0.98 ± 0.35 b | 0.54 ± 0.43 a | 0.51 ± 0.22 a |
| Lamiol | C16H26O10 | 377.146 | −1.34 | 0.93 ± 0.34 b | 0.1 ± 0.06 a | 0.74 ± 0.66 b | 0.79 ± 0.29 b |
| Hydroxycoumarins | |||||||
| Esculetin | C9H6O4 | 177.0198 | −2.32 | 0.14 ± 0.06 b | 0.68 ± 0.19 c | 0.05 ± 0.02 a | 0.1 ± 0.04 ab |
| Esculin | C15H16O9 | 339.0721 | 0.23 | 0.08 ± 0.05 | 0.04 ± 0.03 | - | 0.04 ± 0.02 |
| Hydroxycinnamic acid | |||||||
| Verbascoside | C29H36O15 | 623.1974 | 1.41 | 0.41 ± 0.52 | 0.38 ± 0.25 | 0.08 ± 0.04 | 0.18 ± 0.14 |
| Decaffeoylverbascoside | C20H30O12 | 461.1665 | 0.19 | 1.33 ± 0.86 | 0.6 ± 0.64 | 0.96 ± 0.93 | 1.04 ± 0.36 |
| Phenolic acids | |||||||
| p-Hydroxybenzoic acid | C7H6O3 | 137.0247 | −1.67 | - | 0.05 ± 0.04 | - | 0.09 ± 0.14 |
| Other compounds | |||||||
| Lauroside B/Euphorbioside A | C19H32O9 | 403.1972 | 0.48 | 0.28 ± 0.16 a | 0.3 ± 0.29 ab | 0.37 ± 0.29 ab | 0.71 ± 0.39 b |
Results are expressed as milligrams of compound (mean ± SD) per gram of dry weight. For each compound, different letters between countries indicate statistically significant differences (p < 0.05). The symbol (-) was added when the specific compound was not detected. m/z: mass-to-charge ratio. OL: olive leaves. ppm: parts per million.