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. 2021 Mar 17;2021:6659415. doi: 10.1155/2021/6659415

Table 1.

Secondary metabolites detected in the different Olea europaea meski stone and seed extracts.

No. Rt (min) Proposed EC [M − H]−m/z Δ in ppm RDBeq m/z MS2 (Relative intensity %) Tentative identification Olea meski stone extracts Olea meski seed extracts
MeOH MeOH/H2O MeOH MeOH/H2O
1 2.54 C14H19O8 315.10764 −2.87 5.5 153.0506 (100), 287.1157, 196.7752 Hydroxytyrosol hexoside − − + +
2 2.77 C8H9O3 153.05582 0.64 4.5 123.0452 (100) Hydroxytyrosol − − ++ +
3 3.27 C14H19O7 299.11270 0.57 5.5 Nd Salidroside + + + +
4 3.45 C10H13O5 213.07648 −1.73 4.5 151.0763 (100), 196.8127, 183.0658 Hydroxylated products of the decarboxylated form of hydroxy elenolic acid(isomer I) + + + +
5 3.55 C10H13O5 213.0765 −1.52 4.5 151.0763 (100), 196.8127, 183.0658 Hydroxylated products of the decarboxyl elenolic acid (isomer ΙI) + + + +
6 3.63 C11H13O6 241.07126 −2.08 5.5 Nd Elenolic acid + − − −
7 3.78 C16H21O11 389.10782 −2.86 6.5 345.1174 (100), 287.1134, 196.8236 Oleoside − − + +
8 4.50 C17H23O11 403.12350 −2.67 6.5 223.0603 (100), 359.1330, 333.0810, 179.0557. Oleoside 11-methyl ester + + ++ ++
9 5.82 C25H31O14 555.17032 −0.482 10.5 537.1587 (100), 456.8495, 403.1225, 393.1173, 287.0841 Hydroxyoleuropein + + + +
10 5.90 C31H41O18 701.22791 −1.40 11.5 539.1738 (100), 377.1226, 307.0786, 175.0913 Neo-nuzhenide + + + +
11 5.98 C21H19O11 447.09225 −2.30 12.5 Nd Luteolin hexosides − − + +
12 6.12 C29H35O15 623.19629 −2.97 12.5 461.1638 (100) Verbascoside + + + +
13 6.17 C29H35O15 623.19672 −2.29 12.5 461.1639 (100) Isoacteoside + + + +
14 6.47 C25H35O13 543.20715 −2.13 8.5 525.1948 (100), 513.1946 Dihydro oleuropein − − + +
15 6.51 C31H41O17 685.23309 −1.06 11.5 523.1719 (100), 453.1376, 421.1480, 299.1130 Nuzhenide ++ ++ +++ +++
16 7.14 C10H11O4 195.06624 −0.22 5.5 Nd Hydroxytyrosol acetate + − − −
17 7.52 C25H31O13 539.17572 −2.39 10.5 377.1223 (100), 307.0809, 275.0913 Oleuropein +++ +++ + +
18 7.63 C25H27O13 535.14655 1.55 12.5 Nd Comselogoside (p-Coumaroyl-6 oleoside) − − + +
19 8.35 C25H27O13 523.18054 −2.97 10.5 361.1273 (100), 291.0858, 259.0962 Ligstroside ++ + + +
20 8.43 C19H21O7 361.12854 −2.03 9.5 291.0861 (100), 259.0966 Monoaldehydic form of ligstroside aglycon + + + +
21 8.81 C15H9O6 285.03976 −2.44 11.5 Nd Luteolin − − + +
22 8.87 C17H19O6 319.11795 −2.38 8.5 Nd Oleacein + − + +
23 8.99 C25H35O13 381.15448 −2.65 7.5 363.1430 (100), 349.1275, 331.1170, 287.121 Hydroxytyrosol acyclodihydroelenolate − − + +
24 10.64 C18H33O5 329.23254 0.289 2.5 229.1438 (100), 311.2214, 293.2111, 211.1334 9,12,13-trihydroxy octadeca-7-enoic acid ++ − − −
25 15.61 C19H25O8 377.12372 −1.25 9.5 345.0978 (100), 307.0822, 275.0924 Oleuropein aglycon + − − −
26 17.50 C30H47O4 471.34674 −1.47 7.5 423.3267 (100), 405.3052, 393.3250 Maslinic acid ++ + − −
27 18.11 C18H31O3 295.2378 0.39 3.5 251.2372 (100), 277.2162, 155.1440 Hydroxyoctadecadienoic acid ++ − − −
28 21.01 C30H47O3 455.35178 −2.83 7.5 196.7925 (100), 287.0947, 407.3293 Oleanolic acid ++ + − −
29 21.19 C20H37O2 309.1732 −0.41 2.5 287.1234 (100), 196.7988 Eicosanoic acid ++ − − −
30 22.21 C21H37O4 353.2667 −1.35 4.5 287.0779 (100), 196.8279 Dihydroxyheneicosanoic acid ++ − − −
31 25.61 C27H29O15 593.15009 −1.86 13.5 Nd Luteolin-7-O-rutinoside − − + +

Rt: retention time; EC: elemental composition; RDBeq: ring double bond equivalent; [M–H]−: m/z of the pseudomolecular ion; +,++,+++relative abondance; −not detected.